TRANSFORM Your Life At Any Moment: Alcoholic Lawyer That Became "Fittest Man On The Planet"Rich Roll
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Rich Roll, a globally recognized ultra-endurance athlete and New York Times bestseller, shares his profound journey of transformation from an alcoholic lawyer to one of the fittest men on the planet. His story begins in high school where he felt inadequate due to bullying and a lack of social skills, leading him to find solace in swimming before turning to drugs and alcohol as a "miracle salve" that masked his anxiety and made him feel comfortable for the first time. Despite graduating top of his class at Stanford with world-class athletic potential, Roll's life slowly declined into functional addiction; he became isolated from family and friends, worked toward getting fired in law school, and experienced a marriage that ended on their honeymoon after two DUIs. He describes this period as hitting rock bottom around 1996, realizing his soul was starving while the outside world saw success, prompting him to eventually enter rehab where he learned that addiction exists on a broad spectrum ranging from severe substance abuse to milder distractions like workaholism or phone usage. The core of Roll's philosophy centers on the idea that discomfort is not something to be avoided but rather a privilege and a pathway to growth; however, society often prioritizes comfort over potential because people underestimate what they can achieve in a decade versus overestimating it in a year. He argues that we are all conditioned by early environments—such as achievement-oriented households or social pressures—to live reactively rather than intentionally, creating blinders that hide our true capabilities and desires. Roll introduces his "discipline equation," suggesting that sustainable behavior change occurs when the desire for a goal is high enough to offset its cost, provided the pursuit brings genuine psychological engagement and joy. He illustrates this with his own shift from eating fast food to rigorous fitness training after realizing health was fragile during the pandemic, proving that small, incremental changes made over ten years can completely alter one's life trajectory without needing immediate perfection or suffering. A critical theme in their conversation is the distinction between being driven by insecurity versus truly driving oneself; Roll admits he often feels like a control freak who justifies obsessive attention to detail as necessary for quality but acknowledges it sometimes damages his relationships and causes him burnout. He challenges listeners to ask themselves how they truly feel rather than what others expect, noting that if one is "being dragged" by fear or shame instead of choosing their path with joy, the results may not be sustainable long-term. Roll emphasizes that while pain can force a course correction—like staging a crisis in business or life—it should ideally come from within through an internal examination rather than waiting for external disasters like health scares to wake people up. He advocates for protecting one's boredom and quiet time as essential fuel for creativity, warning against the illusion of connection provided by social media which often replaces real-world interaction with mere digital transactions. Looking toward his future chapters, Roll aims to let go of striving and step into a state of allowing, moving away from the belief that success must be earned through self-inflicted pain or exhaustion. He reflects on how his partner serves as his "North Star," holding a vision for him even when he cannot see it himself, which underscores the power of external validation in manifesting potential. His ultimate goal is to design systems—such as managing his podcast—that are sustainable over decades rather than sprints that sacrifice relationships and health, ensuring he can continue serving others while maintaining balance with family responsibilities like raising seven children. In a poignant closing moment, Roll imagines speaking to his 18-year-old self to tell him it is okay to be who he is without earning love or meeting external expectations, urging the younger version of himself to explore experiences freely and nurture his authentic animating force rather than chasing societal dictates that lead to misery disguised as ambition.
Read the full video transcript
how much pain are you willing to
tolerate before you're willing to course
correct a California lawyer turned
himself into one of the fittest men on
the planet a rich role globally
recognized Ultra endurance athlete New
York Times bestseller and host of one of
the biggest podcasts on the planet he
sat down with a hundred of the world's
smartest people is there one overall
takeaway this theme of transformation so
my story I graduated top of my class the
world ranked swimmer and then I was
working as a lawyer so on the outside it
looked like I was doing pretty well
inside I was dying my first Escape was
through drugs and alcohol my family
didn't want anything to do with me in
the marriage that ended on the honeymoon
went to jail could barely make it up a
simple flight of stairs without being
winded and that was a harsh dose of
reality I needed to overhaul my life I
needed to do something that was going to
be hard and uncomfortable
you can't be a phoenix if you don't burn
in the Flames first
we all want to be this idealized version
of ourself and yet we still don't do it
we are in a culture that prioritizes
comfort and luxury and the impatience
that we all have we overestimate what we
can accomplish in a year and completely
underestimate what we could do in a
decade we don't have to suffer we don't
have to be in pain it's our emotional
lives that hold us back from accessing
that potential so how do people in that
situation take that first step in
transformation what worked for me after
trying many different things was
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why should you listen to this episode
all in all this conversation is
fundamentally about transformation how
you transform yourself from where you
are now to where you want to be in
Rich's life is the personification of
human transformation this guy has been
down and out he suffered with addiction
failure and turmoil that most of us will
thankfully never have to endure but he
says in this episode and he'll prove to
you that pressure that discomfort can be
and should be your privilege and if you
lean into that if you understand that
pressure is your privilege and
discomfort is the pathway to all the
good things that you want in your life
then and only then can you reach your
potential and one of the things I really
got from this conversation is this idea
that all of us are much more capable
than we believe we are we have more
potential than we allow ourselves to
believe
and also one of the big things Rich will
leave you with in this conversation
which blew my mind if I'm honest is this
idea that addiction is on a spectrum we
tend to think of addiction as as he says
junkies or people that are ingesting or
taking drugs
but if you think about it we're all
addicted we're addicted to distraction
whether that's our phones whether it's
pornography whether it's food whether
it's alcohol as is the case in Rich's
case whether it's our work
how do we alleviate ourselves of that
addiction to distraction that's what
you'll find out in this conversation and
most importantly of all riches sat down
with 800 of the world's smartest wisest
and most successful people and from
doing that he has learned a lot this is
one of the episodes that you honestly
should not miss enjoy
[Music]
rich
[Music]
this is a a broad question but it's
intentionally Broad
who are you and what mission are you on
coming out of the gay at heart
that's a very difficult question to
answer I would say that I am
a spiritual being
having a human experience
endeavoring attempting to learn and grow
in a number of ways I had an experience
uh
in my early to mid 40s where I was able
to tap into
potential that I didn't know existed and
I expressed that athletically and that
experience taught me
that we're all capable of so much more
than we allow ourselves to believe and
it motivated me to go on this journey to
grow and expand in other areas of my
life because I realized if I had been
sitting on this late and potential
athletically for so long there must be
other blind spots and I wanted to
explore those and so my mission has been
to grow in the public sphere learn in
the public sphere by having these
conversations on my show and then share
that wisdom with other people for the
purpose of elevating Consciousness and
activating positive change in others
you know you've got millions and
millions of people listening to your
show all over the world you've
interviewed I think almost 800 people
right um
which is staggering um on an individual
level what is it that you hope to impart
or what impact is it you hope to have on
the individuals that listen to your show
I want everybody listening or tuning
into the show to believe to their core
that they are capable of of more than
they may realize that that there is
um a greater possibility for every
single person regardless of
circumstances and there are tools
available for accessing that I think
that's super important because I think
it's so easy to passively or reactively
live our lives we're all on some level
in a routine in a rut and we have
blinders on because we're in a certain
social environment where there's
unstated dictates about what's okay and
what's not and we're all creatures who
want to feel a sense of belonging and
identity with whatever group that you
know we're aligned with and I think that
that comes with very good things of
feeling you know wanted and needed but
also negative aspects which create
blinders to the greater possibilities
that that are available to us everybody
is conditioned in sure some way or
another
um and that conditioning starts fairly
early what you're talking about there at
least in how I heard it is to try and
undo some of that conditioning so we can
live more aligned to whatever worthy
causes
um right for us when was the when did
you start being conditioned and what was
that condition what was the first sort
of con what's the first context or
moment where you're conditioning
began the conditioning that led you on
the journey that you lived
I went to a high school that was very
um
achievement oriented grades were very
important uh academic achievement in my
household was Paramount
and it was a situation in which no
matter what I did it you didn't quite
get the validation that you were seeking
so you're always chasing it a little bit
more a little bit more
um to the point where unbeknownst to me
or on an unconscious level like I needed
to escape that Paradigm and my first
Escape was was through drugs and alcohol
and bullying bullying yeah what take me
into the mind of that young guy that's
being bullied what is he thinking what
is he is he scared going to school is he
trying to escape who he is is he trying
to fit in in certain ways what is he
doing and what is the experience of
bullying like for him
in detail yeah to take myself back I
think I just I just wanted to feel like
I belonged
and I always felt
different than other than the sense of
not being comfortable in my own skin
like other people had a rule book for
life that I lacked
um and just not having the social skills
or the confidence to be able to make
friends or feel like I was part of
anything
and then eventually you you sign alcohol
in drugs as being the
the thing that made you feel other than
yourself in a good way
well initially it made me feel
like myself it was like this miracle
salve
where suddenly all of the unconscious
anxiety and sense of difference between
myself and others seemed to vanish
and that discomfort in my own skin
turned into Comfort like I suddenly felt
like oh
maybe this is how everyone else feels
all the time I've discovered this thing
where now I feel like okay like I can
exhale and I can be around other people
without feeling anxious about it and I
can look somebody in the eye and have a
conversation or like flirt with a girl
or do all these things that seem to come
naturally to other people that seemed
alien to myself and I just remember
feeling so at home with that and just
wanting to feel like that all the time
and it got its claws in me and that's
how that kind of Journey Begins for many
people who've had their version of my
experience with alcohol addiction
addiction comes in many forms and the
the role that addiction was playing the
role that alcohol was playing in your
life
at that stage
can also be substituted for other things
right so some people have it with food
or with
um or with work from sitting there and
interviewing hundreds and hundreds and
hundreds of people what have you learned
about the nature of
really like the role that alcohol was
playing for you but also like the role
that maybe for me like being a
workaholic or for some people eating is
playing what is it doing for us is it
like an escape is it
um in your case it was like the Salve
that made you feel
as you said yourself but what is that
thing yeah I think that uh this is
something I've spent a lot of time
thinking about as somebody who's been in
recovery since 1998 I've been to
thousands of AAA meetings I know so many
people in recovery and over the course
of 10 years of Hosting my podcast I've
had so many experts in the realm of
addictions variety and recovery and
I've come to believe that this notion of
addiction lives on a much broader
Spectrum than we may realize when we
think of addiction we think of uh the
junkie or you know the gutter drunk but
in between you know that polarity
there's a whole spectrum of addictive
and I would even weave in obsessive
compulsive behavior that ranges from
continuing to get into the same bad
relationship to being unable to put the
phone down uh where we are seizing
moments and opportunities through
Behavior or substance to distract
ourselves from ourselves because we are
experiencing discomfort with whatever
emotion is coming up and it's easier to
divert to something that will give us a
sense of ease and comfort or distraction
than to sit with that sense of dis ease
and I think that any kind of recurring
repeated Behavior pattern that mimics
that could be characterized as an
addiction it may be mild but I think
nonetheless it's not you know it's
qualitatively the same thing as the
person who can't stop drinking and it
all goes back to this inside job of
trying to understand what makes us tick
the nature and origin of those
discomforts what triggers those and
trying to find a way to not only sit
with those but confront them and work
through them so you can ultimately
transcend them and liberate yourself
from the behavior or the substance or
whatever it may be that is the kind of
go-to default thing that you do when you
start to feel like out of control or
nervous or anxious or insecure or
perhaps you know triggered or or any
number of kind of emotional impulses
that might arise what is the cost of not
learning to be with myself so I'm
looking at all these things for an
addiction I'm definitely addicted to my
phone all of these addictions I've got
some of them in you know very varying
degrees
um so what
what's the cost well
time will tell right right maybe there
isn't a cost that is so significant that
it mandates that you Rectify that
behavior again it's a spectrum right so
for you you might be able to engage in a
certain Behavior without having negative
ramifications in your life that are
significant enough for you to redress
that for somebody else it might destroy
their life but I think developing an
awareness around those behaviors and
paying attention enough such that if you
start to find yourself experiencing
negative life ramifications as a result
of those behaviors you're not
um in denial over that and you can make
a course correction and what's the
upside then of just learning to sit with
yourself as opposed to reaching for the
phone or for the the cake or for the the
beer what is the what is the upside of
that you know I say this because I think
I live in a generation that have become
so used to distracting ourselves
um and the thought of like meditating or
not having our phone on us is actually I
mean it's like a it's like a phobia
um we haven't learned to sit with
ourselves in Silence with our thoughts
if you can't sit silently with yourself
with your thoughts then you are not
living an intentional examined life and
I think to be addicted to your phone or
to be living in that reactive mode where
you're constantly distracting yourself
robs you of something that we need as
human beings which is rumination and
boredom that is the juice of creativity
and as a creative person somebody who
does this show and talks to amazing
people and is writing a book and is very
much in a space where your creativity is
really uh the driver of everything that
you do I would say to you it is of
Paramount importance to protect your
boredom to protect your quiet time to
put boundaries around those distractions
otherwise you are not going to be doing
your best work and you are going to be
depriving your audience of the best
version of yourself
the other thing is connection it's
definitely it's definitely robbed me of
connection
well it's it's pernicious in that way
because at least with social media it
gives you the illusion of connection and
you know we're sitting here together
because of social media like you reached
out to me I reached out to you so it's
not a binary there are amazing things
about it and my entire career has been
built on these
digital tools and they're very important
to you know how I kind of navigate the
world but at what point does that meter
kind of toggle over into you know the
the red zone where I'm being used by it
and it's robbing me of my humanity and
it's deluding me into this idea that I'm
connecting with other people but in the
analog world I'm just at home all the
time and I'm not actually interacting in
the real world and you know I think one
thing we share Stephen is our show is
all about the in-person experience like
I tried to do the zoom thing I can't do
it it's like this is not why I'm doing
this yeah I'm not getting it feels
transactional and weird and yeah and you
know as as as much as these these tools
which are phenomenal
um have given us the ability to connect
in a certain way it's not true
connection and I think you know in order
to really feel like we're part of the
human race we're hardwired to be with
people in real world World settings when
I look at your story I see multiple
chapters and there's transformation in
every chapter sometimes for better
sometimes for worse but it's always
forward so it seems like it was the path
that you had to to go on you talk there
about the first chapter of your life
which is your young there's bullying
there's this feeling of sort of
inadequacy and there's isolation
what's the next chapter
yeah so
um awkward insecure kid difficulty
making friends
um but I found Solas in the swimming
pool and that was really my safe haven
perhaps my first addiction
um and in lockstep with my Improvement
in that space came uh came better grades
I started to perform better athletically
so by the time I was 18 and graduating
high school I had my pick of going to
any college I wanted to got into Harvard
Princeton ended up going to Stanford
which in addition to just being a
premier University I also happened to
have the number one Collegiate swimming
program in the country so basically
anything I wanted to do was like laid
out in front of me I arrive in
California for college I grew up in
Washington DC so traveled 3000 miles
away to go to school enter alcohol and
that began the sort of slow
decline of my ability to express my
potential not only as an athlete and as
a student but as a human being because
it just gradually denigrated
um all of my values and and sort of
dented my aspirations to the point where
I know really I no longer really cared
about my trajectory or where I was
headed with my life and was solely
concerned with rooting out where my next
good time would be and those were the
good times and I would say that
initially alcohol really saved me it
taught me how to be a social person like
I enjoyed going to parties and I enjoyed
figuring out how to talk to people and
it was really this fuel that transformed
me from this Naval gazing insecure kid
into somebody who felt like I could
comport myself in a social situation as
long as I was using alcohol I've taken
some of those skills and I'm now able to
apply them without alcohol but very
slowly over time you know my life the
quality of my life just sort of declined
and declined and declined so I was a
functional alcoholic for many years
but I knew very early on
that my relationship with alcohol was
different from that of my peers because
I would be the last person to leave
I was immediately sneaking drinks I was
the one who was throwing up and blacking
out when everyone else knew what time it
was to go home I started going out like
more and more nights every single week
and then fast forwarding through later
years
hiding my drinks sneaking my drinks
hiding the empties and doing kind of all
the dark stuff that one does when they
fall prey to this condition
and it it there was nothing really sexy
or romantic or rock and roll about it
was just really kind of sad and pathetic
to the point where at the end I was
alone alienated from my friends my
family didn't want anything to do with
me until I sorted this out I was on the
precipice of you know somehow I got
through law school but I was working as
a lawyer I was on the precipice of
getting fired was living in a shitty
apartment with barely any furniture
sleeping on a mattress on the floor and
it was it was it was very dark for a
very long period of time
when did you get married the first your
first marriage in
1995 20 must been told that was so it
would have been
90.
96 I think yeah
they ill-fated marriage that ended on
the honeymoon that's a sordid story that
would take a very long time to untangle
and explain
um a marriage that ended in the
honeymoon it ended on the honeymoon yeah
uh
incredibly
um painful embarrassing chapter of My
Life
um that that marriage took place after
I'd gotten the the two DUIs but I was
endeavoring to get sober and I think my
fiance not quite my wife because
we didn't sign the marriage certificate
which is a whole other aspect of the
story
um
I think that she realized that
I would be problematic as a partner
but didn't have the courage to call the
whole thing off and allowed the wedding
ceremony to take place even though she
didn't want to be married to me and it
all kind of came to head on the
honeymoon
um
which is the last time that I saw her
and that was really my bottom uh as an
alcoholic even though I drank for a
period of time after that because it was
so emotionally devastating and painful
that was really the nadir where I
realized that my life had hit the skids
in in in just a you know a way that I
could have never imagined for myself
post that
um that I was gonna call it I guess it
was a wedding post that wedding and
everything that happened you returned to
drinking again you relapse because of
the pain of that experience absolutely
how long does that last
night it was a long time ago I think it
was about six more months
of
my life kind of circling the drain
um before I finally decided that I
needed to really take responsibility for
my behavior
at that point what are the people around
you that love you
doing and saying
uh friends slowly stepping backwards
from me
um
distancing themselves from me my parents
were terribly worried
and concerned
and they had sought out counsel of their
own and started attending Al-Anon and I
believe they had seen a therapist as
well and and through the advice that
they got was like you need to cut ties
with this guy like you can't will him
into doing what you know is in his best
interest you have to detach and I recall
very vividly a conversation that I had
with my dad where he's like I know what
you're doing
it's very clear uh this path that you're
on and we just can't be part of it
anymore and if and when you're ready to
make a change or to really entertain
sobriety in a real way we're here for
you we're your parents and and we love
you but until that point like we really
don't want to hear from you anymore
so that was
a brutal
pill to swallow incredibly painful
but also catalytic because it snapped me
out of whatever denial I was harboring
about getting over on people or them not
really knowing how I was actually
behaving and I think it was an important
step in helping me realize just how dire
the circumstances were for me at that
time when your father said that what did
you hear
I heard you're a failure
and you are unlovable
do you think that was the right thing
for him to say
I think in my case and I'm only speaking
from you know my perspective in this
particular set of circumstances
it was the right thing to do because it
effectively moved me in the direction
that I needed to be moved in
and they had tried the other way which
is loving me and being supportive and
and kind of
offering up a soft landing pad and that
was not working
and I think they needed to do that
for themselves to protect themselves as
well
and and I respect that choice you know
I've been in many situations trying to
help
people get sober and it's a very
delicate difficult thing to do it's just
really challenging because if somebody's
not ready and they don't want to get
sober there's very little that you can
do to try to you know create that
Epiphany in them willingness is a
self-generated
um response that you can't instill in
somebody externally and until somebody's
really willing to confront their demons
you can't compel them to do so so
uh that's why I think sobriety or
addiction is so baffling and so painful
for
the loved ones of people that suffer who
can so clearly see you're killing
yourself you need to do this and yet
that person won't make that choice
just addiction and
um sobriety in that sense that
I was thinking about when I asked that
question because I've got people in my
life that I've tried to help in various
ways and I've got a one one friend who
has struggled with um pretty severe
addiction and your natural inclination
is to try and jump in there and give
them advice and help them and pay for
this and sort sort this out et cetera
Etc
but after you know years and years of it
never working
what do you do then and I'm thinking of
one particular example of a friend of
mine who struggled with addiction and
slowly everybody has just Fallen away
the person's management has fallen away
their friends have fallen away
um
and I wonder sometimes I wonder to
myself is that what you have to do is
that do you have to basically give them
a void enough space and stop holding
them up in like sort of artificially
suspending them
uh and let them go to the bottom let
them go to that Rock Bottom there is a
logic in that you know you don't want to
coddle that person you certainly don't
want to be codependent in their behavior
in other words making excuses for them
that makes it easier for them to
continue down that destructive path
um and there is wisdom in just saying
hey man I love you I'm available when
you're ready to get help uh but you know
you're you're on your own thing man and
I just I can't be part of it so call me
when you're ready but until then good
luck to you because the addiction
elevator is always going down it's a
progressive disease it only Moves In One
Direction the best case scenario is that
person's life stays the same but in
almost every case it continues to
decline and it will decline to the point
where the pain experienced by the person
who is the addict or the alcoholic
becomes more unbearable than the fear of
the change and that is where their
willingness is born and again it's not
something that you can instill in that
person you could you could like hijack
your friend and throw them in the back
of a car and drop them off in a rehab
but he might escape from the rehab or
he'll sit in the back and just bite his
time until he or she gets out and they
can go back to whatever they're doing
that's why this is such a difficult
um
problem to solve it is an internally
generated thing the people that I know
that have been able to get sober and
stay sober are the people that shoulder
responsibility for their own sobriety
you can't get sober for somebody else
I'm getting sober for my spouse or my
kids or you know I'm getting sober
because if I don't my boss is going to
fire me those are those you might be
able to do that for a short period of
time but for the true addict unless
you're doing it for yourself and you're
making it your number one priority
chances are you're not gonna you're not
gonna last over the Long Haul and it's
confusing and when you love that person
it puts you in a very treacherous
position because if you do create that
boundary and that person goes off and
something terrible happens will you feel
responsible or will you feel like you
didn't do enough or if you had just done
this or that that wouldn't have happened
and that's a very real predicament to
put yourself in
there's something quite
counterproductive in the sense that
when you're trying to help that person
what often happens is your relationship
with them becomes strained and then when
your relationship becomes strained and
you you become frustrated with the lack
of sort of effectiveness of your support
then arguments start you might say some
things that you regret further
tarnishing that person's self-esteem
self-worth or whatever's triggering them
to try and Escape themselves through
whatever addiction they might have and
it it actually can make make their
situation significantly worse sure
destroy the relationship right which is
why it's important to to interface with
that from a place of neutrality right to
not get emotionally agitated or
activated by it and a good way of of
kind of recalling that or reinforcing
that is to understand that there is the
person your friend and there is this
disease this addiction right and if this
person is acting in their disease that's
not the person they're not a bad person
they're afflicted by something so
powerful that they're unable to override
it and and you know be that friend that
you remember and I think when you when
you kind of approach it through that
lens you can have a little bit more
compassion for that person rather than
take it personally because they're not
they're not acting out of animus towards
you they're suffering from something
that's so powerful that they're unable
to to control it
quick one before we get back to this
episode just give me 30 seconds of your
time
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thank you thank you so much back to the
episode okay so this was a quote I I
found about your opinion of balance he
finds balance extremely difficult and
believes that if something is good then
the more the better he believes balance
is for ordinary people and he wants to
be extraordinary he says this can be a
blessing and a curse yeah definitely a
blessing and a curse
um I am hardwired for extremes uh this
has been both a superpower and an
Achilles heel it's the thing that has
fueled me and allowed me to you know
achieve uh some pretty cool things but
it's also been the thing that um has
almost killed me so it's that love hate
thing but I think behind it this notion
of living a balanced life that we get
served up like you need to be balanced
and you know the best way to kind of
pursue your life is in a balanced way
everything in balance and the social
conditioning around that idea is so
powerful that for years I just felt like
a terrible person or
um like less than because I just could
never figure out that equation to make
everything feel like it was even
adequately balanced because I feel most
alive in those extremes and that's part
of what addiction is like you're just
searching for those Peak experiences in
unhealthy ways and also in healthy ways
through Athletics and and you know
and through uh creativity and and other
avenues
um but I always felt guilty about that
like
other people seem to be telling me that
I shouldn't be doing this and yet
this is where I feel like myself and
finally I got to the place where I was
like this whole balance thing like
this is who I am
and I decided to embrace it now that
doesn't mean that
um you just blindly pursue these
obsessions to the point of
self-destruction what it means is for me
again not giving advice uh in my
experience when when I allow myself to
uh
immerse myself in something that
um fascinates me whether it's
an ultra distance race or writing a book
or whatever it is giving myself
permission to really focus on that and
take it all the way to the wall is where
I do my best work but that is only
acceptable as long as that pendulum
that's swinging all the way up over here
swings back
goes this way and comes to the center
because we all have
buckets in our life
of values that we you know need to
nourish so a creative project for
example I'm going to go I'm going to do
that and that's fine as long as I come
back and my family is nourished my
relationship is nourished my friendships
are nourished all these other areas that
are important to me don't fall by the
wayside for too long so balance in the
macro but not balancing the micro so on
a day-to-day basis or a week-to-week
basis my life is wildly out of balance
but if you look at it over the course of
a year you telescope out I think I think
it's much more imbalanced than
then one might suspect
super interesting I've I think
using that example of the Swing is it
called the pendulum
in society we started by glorifying
hassle culture I guess and being out of
balance and then there was kind of a
movement towards that's toxic right and
now I feel like the new pride is like I
don't set my alarm clock yeah yeah
and I feel like a little bit is coming
back the other way where people are
going work-life balance like that's
it's such balance is such a subjective
thing and work is completely different
for everybody like this is my work this
is not I'm not you know for someone else
their relationship with that work might
be tedium it might be depressing they
might be doing something that really
doesn't fill them up but
I think there's needs to be Nuance in
the fact that all work is different
every individual is clearly different
and it is wired to find the Fulfillment
in different ways so work-life balance
in and of itself is a pretty ridiculous
concept to think that there is a balance
there really must be as you kind of
describe a subjective balance where
there's a balance for Steve
and as long as I don't fall in sacrifice
social connection isolation and all the
other things then I'm balanced my
balance could you know look much
different from yours for whom and when
right if you're 22 years old and you've
got this idea for a startup and you're a
coder and you want to code like a maniac
like knock yourself out you have no
other responsibilities you have the time
you have the freedom to do that in that
moment but that 22 year old 20 years
later with kids at a mortgage and
whatever it's a different time that
person's in a different place these
things you know can't be they have to be
contextualized right and yes if you want
to achieve something great you are going
to have to work very hard and you're
going to have to get out of your comfort
zone you may even need to be obsessed if
you're living an entirely Balanced Life
where you're home at five o'clock and
you're always at dinner and all it's
like you're making it very difficult to
achieve something extraordinary
that extraordinary thing is going to
require an extraordinary commitment
which means in the social construct of
balance you are going to be out of
balance if you're going to feel
uncomfortable with that because you have
other priorities in your life then maybe
that's not for you and being out of
balance to pursue something great in my
opinion is perfectly fine again as long
as you allow that pendulum to swing back
and those other things in your life that
are important are nourished and attended
to so it's a very specific thing it
depends on who you are what stage of
life you're in what you're seeking and
having the self-awareness to understand
that you can't be everywhere all the
time and you can't be a hundred percent
for all of the things that are important
to you in your life in every single day
so it's about conscious awareness and
intentionality about where you're rowing
that boat you can only row your boat in
One Direction are you rowing the Steven
boat towards Stephen today are you going
to row it towards your girlfriend well
you gotta you're gonna have to do a lot
of rowing in a lot of different
directions it's just knowing that you're
making a conscious choice and doing that
with that understanding and appreciation
I think is really important but all of
this
is to put the lie to the idea that
anybody is living a balanced life on a
minute to minute hour to hour day-to-day
basis it's like a it's a construct that
I think makes people feel guilty and bad
about themselves because none of us are
adhering to that
idealized version of a balanced life
that we have a mental picture of
you kind of have it all you left rehab
in September 1998.
um and earlier on when you're talking
about transformation you describe
someone who goes from being a fairly
ordinary person to running a marathon
that was one of the sort of examples you
gave of something that intrigues you
like how did they do that that's pretty
much in many respects what you went on
to do upon leaving rehab as you your
life
slowly move towards Ultra athletic
sports
yes and no I mean I think that uh the
the shorthand kind of Google version of
my story makes it look like all this
stuff happened in a very compressed
period of time but actually when I left
rehab which is where I live for 100 days
and
resumed my life in Los Angeles I spent
the next 10 years trying to solve the
Dilemma of my life that I had
self-created I had to repair my
relationships I had to become
trustworthy to other people again I had
to
um you know be somebody who was reliable
and would show up on time when they said
they would all those sort of like normal
things that normal people do I had to
rebuild for myself so for 10 years I
immersed myself in the recovery
community in Los Angeles and I tried to
become that corporate lawyer that I
thought that I wanted to be to be kind
of approved of by my parents and by
Society Without Really grappling with
who I wanted to be because I was so
caught up
and so ashamed of my past and
embarrassed of how I had screwed my life
up that I wanted to prove to myself and
to everyone else that I could be that
person that I was at 18 when I had all
of these opportunities and choices and I
was blind to kind of the inner Journey
despite sobriety the blind to like
really trying to figure out like what
made me tick and what I might
want to do for myself that felt like an
Indulgence and so the ultra stuff came
much later that came like so I got out
of rehab at 31. it wasn't until I was
turning 40 that I had another bottom
where I had to reckon with my lifestyle
choices with diet and movement Etc
because I'd put on 50 pounds and was
just pursuing this corporate life to the
point of of of of of illness honestly
like I was although I'd been this
athlete I just could barely make it up a
simple flight of stairs without being
winded tightness in my chest heart
disease runs in my family and just had a
second situation in which I realized I
needed to overhaul my life so there was
a whole 10-year period in between those
those kind of moments of Awakening that
10-year period is a 10-year period that
a lot of people listening to this right
now can relate to where you found
yourself in a professional context or
professional endeavor without asking
yourself the question of like who am I
and what am I actually interested in and
you might be doing it because your mum
wants you to be a doctor sure you have
the Indian parents and they came over
here and they want you to be a lawyer
whatever it might be I hear that story a
lot what is the question it people in
that situation should be asking
themselves and how do they take that
first step in transformation from
becoming the banker that's in the city
with a suit in town right now listening
to this
to the person that like would make make
them whole and full and
and love themselves in their life like
what is the first step is it a question
is it a retreat they need to go on
yeah it's a great question I think that
question is probably different for
everybody but how about just asking
yourself
who are you and I mean that in the
broadest sense perhaps the most
unanswerable spiritual sense but I also
mean it in the very tangible sense of
like what are you doing
are you really on the path
that you want to be on did you choose
this path are you here because of
external pressures or expectations that
you didn't ask for and I think when you
turn inward and start exploring your
interior to try to Grapple with what is
making you tick what is impulsing the
decisions that you're making the big
decisions and the small decisions and
developing a lattice work or an
understanding of what those mechanics
are sets you on a trajectory to making
better decisions for yourself so it's
not like maybe that Banker is supposed
to be a banker maybe super happy that's
fine I'm not here to tell people they
should quit their jobs I'm just saying
that an examined life meaning that
inward glance into
understanding why you're making the
decisions that you're making
um
historically uh you know the way in
which you were raised that might have
set you up to make decisions you think
you're making for yourself but are
actually in reaction to unconscious uh
uh you know kind of triggers that are
built into you I think developing an
awareness of that is really important in
trying to understand that question and
it took me a very long time to untangle
that knot I don't think it's a simple
process I think it's different for
everybody it can come in the form of
talking to a therapist or meditation
there is no one modality for that but I
think simply the commitment to try to
understand that I think is the process
of
gaining that understanding to help you
make more intentional decisions for
yourself and maybe it starts with an
easy prompt like what did you enjoy
doing when you were eight years old that
you don't do anymore and why don't you
do it anymore
re-engaging with you know the childlike
nature uh that is perhaps lost as we
grow older and kind of
get into the flow of our professional
lives one of the most important
questions I think I would add as well as
how do you feel
we very rarely ask ourselves that and I
think we all have this sort of internal
Compass which we've been given by life
which is like how do you feel in this
situation how do you truly feel not like
how do you feel in the context of is
your mother happy or is your father
happy or a society impressed by you but
like how do you actually feel you know
and I think that sometimes for me has
sat apart from the accomplishment so I
could be achieving something great and
know that people are impressed and happy
but really I'm going through a
time internally right and um tuning
into that voice of like how do I feel
and tuning out of the like how do people
feel about me right um has has really
helped me in those moments where I've
got to make a big decision to quit and I
don't think people ask themselves that
question enough
well they may ask themselves that
question but the answer is flip it right
it's like I'm good cool I feel good you
know I feel I slept good last night no
like how do you really feel
and then continuing to peel back the
layers until it gets really
uncomfortable and then you know you're
in the you're in the sweet spot right
that's where the juice is I've peeled
them back I've re and I've done you know
raised my awareness I realize I'm in the
wrong place but I'm 39 years old
and I've got kids I've got a house we
live in this part of London so I can get
to work quickly we've built our lives
around this
you know person I thought I wanted to be
and I'm held in place by the my
friendship group and my Monday's done
people have that fear they think how do
I how do I break out of that how do I
shed yeah
yeah well first I would say to that
person congratulations like you created
a life for yourself like on some level
even if you want to leave that career
path or you're unfulfilled in that you
still are somebody who is deserving of
acknowledgment for building something
and you know that's an amazing thing so
it's not about casting that aside or
disrespecting it for me I would say to
that person
what is it that gets you excited like
what is it that you feel is unnourished
in your life do you have a creative itch
is there something calling you or
something again that you used to do as a
kid that you really enjoyed and for some
reason unbeknownst to you you don't do
it anymore maybe it's music like yeah me
it could be music or or stand up or you
play football right like being on a
football team or doing something you
know just having coffee with your friend
or what have you uh finding a way to
build that back into your life in a way
that isn't going to derail your current
life but I think just breathing on that
like giving space to the things that
bring you Joy in the most Primal sense
like the simplest things that just you
remember made you happy that you've
forgotten and recapturing that and
finding a way to respect that protect it
nourish it
um and and inject it into your life and
I think the more that you you kind of
tend to that Garden suddenly oh a little
opportunity over here pops up or
something is telling me I should move
this way these are very subtle energies
that you have to be present for in order
to notice them when they appear but I
think those are the subtle energies
that's the like those are the waves you
want to be surfing and you can do that
while you're working at the bank
they don't have to be mutually exclusive
and over time maybe you start moving a
little over this way five years later
your life is unrecognizable and I think
this goes to
the impatience that we all have we all
want to be this idealized version of
ourself happier fitter thinner richer
whatever it is overnight and we
overestimate what we can accomplish in a
year or maybe in a couple years and
completely underestimate what we could
do in a decade we're not wired to think
in decades it seems too intangible but
if all you do is make tiny little
changes to build in
habits into your life that bring you Joy
or fulfillment or happiness or purpose
in incremental micro allotments that
don't disrupt the rest of your life
you do that for 10 years straight
your life is going to be different and I
can promise you that
10 years off to rehab you have what you
describe as your second rock bottom
you're a workaholic you're trying to
sort of appease the perception of people
in your life to make them proud I guess
um just before your 40th birthday
this is when that sort of Reckoning in
your life takes place what is that
Reckoning in your life what did you
realize and and what did you see as the
solution to that
confrontation yeah so I had spent the
better part of 10 years uh people
pleasing and doing my best to be
successful living somebody else's life
unbeknownst to me doing all the right
things checking all the boxes becoming
successful so if you were on the outside
looking in it looked like I was doing
pretty well inside I was dying because
my soul my spirit was unheard and under
nourished like I didn't know how to pay
attention to myself or the signals of my
soul who were telling me I don't think
you're that happy doing this and we're
pressing that year after year after year
to the point where uh
I couldn't do it anymore so I was
harboring a bit of an existential crisis
about how I was living my life being
this lawyer and kind of showing up in
the world in a certain way that always
felt like a costume that didn't fit me
meanwhile uh although sober from drugs
and alcohol I'd sort of transferred a
lot of that addiction energy into into
food and was eating you know a terrible
fast food diet gained a lot of weight
was inactive even though I'd been a
swimmer in college wasn't really moving
my body in any meaningful way for a
number of years this existential crisis
that I was having collided with this
health scare shortly before I turned 40
where I was going up a flight of stairs
after a long day at work and couldn't
even make it all the way up had to stop
halfway up the flight winded out of
breath tightness in my chest like
wheezing you know thinking I swam at
Stanford like I was a world ranked
swimmer I can't I'm I'm like 39 about to
turn 40. I feel like
I'm fat and it just broke that
spell of denial about how I was living
where it became intolerable to continue
along that path and it was very much
like the day that I decided to go to
rehab like this moment back to
willingness like suddenly out of the
blue
I was blessed with this realization not
only that I needed to change my
lifestyle habits but that I had the
willingness to actually take action on
that and because the decision that I had
made 10 years prior when I went to rehab
had been so transformational like I
could have woken up that day and made a
different decision what would my life
look like and I had this palpable sense
that once again
this was
just such a moment where if I could make
a decision like I had 10 years ago maybe
I could change the trajectory of my life
and I know that these moments are
fleeting and and they require kind of
immediate action or they pass right you
could say
maybe I should eat better or go to the
gym once in a while like I'm tired of
feeling like that's so vague I knew
that that wasn't going to work for me
and I needed to do something immediate
that was also difficult that would mimic
the experience of going into a treatment
center for drugs and alcohol like I
needed to have a structured situation
that would snap me out of my comfort
zone and kind of create a new trajectory
upon which I could build something
different
I think I think about this a lot in like
businesses and organizations they almost
need to Stage a crisis I call it to make
change happen because when you when
you're in an organization and there's
maybe thousands of people and let's say
it's AI or an innovation comes along
people will go yeah it's a problem but
you know I'm fine and then they'll kind
of carry on keep on keeping on the
organization almost needs to Stage a
crisis like everyone in a room and say
we're changing today and really sort of
terrifying terrify their team about the
the prospect of not changing it's almost
like staging a rock bottom because it
will be the frog in the frying pan it
will slowly creep upon you if you don't
right at some point as I call it like
stage of crisis
which is to really get clear on where
this is heading
and where we're sleepwalking ourselves
into whether it's with our health our
relationships I actually had this
conversation with a friend of mine in
his relationship because he's now in a
sexless relationship and he's really
unhappy
but he's not saying anything about it
he's kind of bringing bringing it up
sort of quietly once in a while and his
unhappiness in the relationship and
resentment is coming out in other ways
in the relationship like arguments and
fighting where he needs to stop and like
stage a crisis like not allow it to be
brushed under the carpet anymore and sit
down and say listen if we can't solve
this I have to leave this relationship
and like I want to solve it with you but
it's a deal breaker for me see what I
mean yeah I get what you're saying
basically short of of like sleepwalking
yourself towards the Cliff's Edge yeah
do staging an intervention on your life
by you know like concocting a crisis
sounding they're gonna compel you to
confront the elephant in the room that
is the thing that is holding you back
it's obvious to everyone else and yet
you're refusing to look at it yeah
because we as you said earlier we want
to avoid discomfort so if we can't just
sweep just Comfort under the carpet and
procrastinate it into tomorrow we do we
do that in businesses we do it in our
own lives so how do we maximize the
discomfort today by presenting what the
future will look like if we don't take
action right now right and there is
often a point of no return in
relationships and in business for sure
for sure
so yeah I think that's a very kind of
pragmatic uh you know three-dimensional
uh actionable way to look at it perhaps
a more
mystical way to approach this is to say
that when you are living your life out
of alignment with your best self
the universe comes knocking and it
knocks gently like you're maybe you're
out telling lies or whatever it is like
you're just not you're not you're not
living your life in
Integrity like
in alignment with your own values and we
all do this right we're not all living
perfect lives so and and and so when you
do that like there'll be nudges and
those nudges will be very graceful at
first and if you ignore them a little a
little bit louder right yeah
yeah that's fine I can I can you know I
can deal with that the knocks start to
get more intense more intense more
intense more intense and then you get
two DUIs in six months and you're in
jail or your partner leaves you or
whatever it is right like how much pain
are you willing to tolerate how loud
does the knock have to be before you're
willing to course correct change is very
difficult we don't want to make change
or look if if if uh
if change were easy or it was a logical
thing like here's the answer do this and
if everybody just did it there would be
no self-help industry there wouldn't
need to be any books you just tell
somebody what to do and they do it so
why don't they do it right we don't like
to be out of our comfort zone we have a
certain way that we live our life and
until that is so disruptive disrupted
we're going to continue on that path
right so
the question becomes how much pain do
you have to be in before
you're willing to
walk through the fear of the unknown
that the change presents
how loud is the knock have to be how low
does the elevator have to to drop and I
think that that answer is different for
everybody but the amazing and confusing
thing about it is that the possibility
of change exists in all moments we can
make that choice at any time we don't
have to suffer we don't have to be in
pain and yet
we still don't do it
so unlocking that mystery yeah I mean
well there's your book you can answer
that question well I've been playing
around with this idea in my book there
was a chapter I was going to write about
time
right so I wanted to write something
about time and time management so I
thought the best place to start is
talking about death because that kind of
puts time and context it's finite
um so I started writing about that you
know if you're 35 years old you've got
17 000 days left I'm trying to you know
find all these ways where people can
visualize the con because because of
what you said people can't think of
decades we can't think of finality we
can't think of infinity we can't think
of long periods of time I'd also at some
level don't believe we know we're going
to die we don't live our lives
accordingly yeah we think it happens to
other people yeah exactly yeah deep down
we're like somehow I'm gonna sidestep
this thing it's not actually gonna
happen yeah and you see that in our
decisions like the things we pour our
attention into clearly we don't think
we're on a clock here right um a clock
we can't see so that's how I started the
chapter then I went into time and I was
like okay time management techniques I
looked I was thinking about my own time
management techniques I then was like
I'll Google it chat GTP went on chatty
speed talk to me about time management
techniques there's so many of them and I
thought to myself the reason why there's
so many is the same reason there are so
many fad diets because none of them work
unless you have discipline
so that people just keep making new ones
and they keep selling because none of
them work without this thing called
discipline so what causes discipline
and then I arrived at this sort of
discipline equation in my head where I
kind of believe when you want I was
going to say this in a super vague Way
Broadway
when your perception of how meaningful
the goal is
Plus
the enjoyment and psychological
engagement you get from the pursuit
towards the goal so for me I really want
to be a DJ
I've played around with the idea for a
long time I finally made the decision I
wanted to do it why do I want to do it
absolutely love music Love The Thrill
and how energized I am from from
Performance Plus the psychological
engagement enjoyment I get from the
pursuit it's like meditation DJing and
the practice of it right so you go
upstairs into my kitchen I spend hours
listening to my favorite music and
merging it with other songs I love for
hours forgetting about the whole world
minus
the perceived psychological cost of the
pursuit
so what does it cost me to pursue DJing
and I think that is roughly my
discipline equation so if you think
about these three elements how bad you
want it how enjoyable it is what does it
cost
you can kind of think of why people
might or might not change and if someone
fits into what you said about when the
pain of staying the same becomes greater
than the pain of making a change then
people make the change
um when they really really want it and
it's
more enjoyable than it is painful
to go in that direction Behavior changes
right well I would
take it one step further but first let
me let me say this I would say that
you're already a DJ you're making uh an
assumption around what it means to be a
DJ or to pursue DJing that comes with a
lot of baggage it means success maybe
you're envisioning a big crowd of people
who are listening to your music but the
fact that it brings you Joy and you've
found a way to carve time out to nourish
that it doesn't matter how far it goes
or doesn't go as long as you are kind of
cultivating that out of that
purity of spirit because it nourishes
your life so that's what I mean when I
was talking about the banker right like
just DJ or kitchen table like it doesn't
have to be any more than that if it if
if you're finding so much joy in it then
you can recalibrate that equation about
how much energy resources and time
you're going to invest in it but right
now if it fits into your life and it's
it's making your life better than
the question would be does it need to be
more than that do you need
it to be attached to some external
validation or monetary reward or
recognition in order for you to believe
that you actually are a DJ
and that's not saying there's an answer
to that question but it's something to
think about this the reason I gave the
DJing example is because it was
something I was able to stick out I was
able to quite essentially change and
there's some and my health was the same
thing it fits into that discipline
equation of at some point in my life I
saw this pandemic happen I saw the
fragility of this thing called Health in
my young 25 years I'd never even knew
was there I never even knew I had health
because mine had fortunately always been
well and then upon seeing the pandemic
play out and hearing the doctors and
scientists say that your current health
you know obesity is linked to your
chances of
um suffering having sort of worse
effects of this disease that was enough
for me to put me in the gym for the next
three years and I haven't missed uh more
than two days since pretty much in a
week for the last three years that was
my behavior change before then I was the
guy with the fast food
right so that was the moment that was
the Line in the Sand moment that piece
of information created willingness in
you which is the first part of that
equation which is the why like why do I
care about my health right it added so
much weight to me caring about my health
but discipline is easy when you have
that why yeah answered right so
if it was just that easy I think that
more people would be able to make
positive changes in their life but I
think where it gets more complicated is
when we understand
beneath the surface
that it's our emotional lives that are
truly the things that hold us back from
accessing that potential you can be
incredibly disciplined but if you think
you're a piece of or you don't
deserve good things in your life or
you're being impulsed by some trauma
that happened to you you were abused as
a young person that's going to show up
in your life as a barrier or an
impediment from you doing the thing that
you know you need to do to become the
person that you could potentially become
so the head discipline can drive us so
far but if we don't sort out the heart
and what is making the heart beat what
is making us move in One Direction
versus another and untangling or
detaching or transcending
the emotional baggage that is the true
impediment to our growth discipline is
only going to take you so far
so you
um became an ultra Endurance Sports
athlete
from that point of where you can walk up
the stairs without losing your breath
what was that transformation
so after that moment I decided to take
responsibility for my well-being
and thus began a pretty long and
inelegant and non-linear process of
first trying to figure out how to eat in
a way that would allow me to feel good
in my body that began with a seven day
juice detox cleanse that I did not
because I felt like I needed to detox
anything but I needed to
recreate the experience of detoxing off
alcohol that I had in rehab like I
needed to do something that was going to
be hard and uncomfortable and not eating
and just drinking juice seemed like a
good way to accomplish that I'd never
gone a day without eating food before
and that was an experience where I was
incredibly uncomfortable and I felt
horrible for a couple days but on the
seventh day I felt amazing and I
couldn't believe that only drinking
juices for seven days could result on
day seven in this boost of Vitality and
mental acuity that I hadn't experienced
in a long time as somebody who was
eating cheeseburgers every day and and
that made me want to figure out a way to
feel like that all the time and so I
ended up trying a bunch of different
diets and what worked for me ultimately
after trying many different things was
going entirely plant-based I'm not here
to tell everyone that that's what they
should do but that's what agreed with me
and that's the way I've eaten for the
last 16 years and you know this
um
this approach to nutrition restored my
vitality and gave me a renewed sense of
energy so much so that I had difficulty
sitting still and finally wanted to like
move again and pulled out an old pair of
running shoes from the closet and just
started moving my feet again and I went
back to the pool for the first time in a
very long time and was just connecting
frankly with these things that brought
me joy as a young person like I was a
swimmer and I hadn't done it in a long
time and I'd forgotten what it feels
like to jump into a swimming pool on a
sunny day and feel the water and connect
with my breath and you know
move my legs on a trail at dawn and I
really loved it and I felt like that was
a journey towards
answering these questions that I was
having on the existential front about
what I was going to do with my life
because I had a lot of confusion at that
time and just the mental space of like
being alone with my breath in the pool
or on a trail running was very healing
for me and I had no aspirations of of
becoming a competitive athlete with it I
just wanted to feel good I wanted to
like lose this gut you know frankly for
vanity reasons I didn't like how I
looked in the mirror and the weight came
off really quickly and I felt like I was
making incredible progress athletically
week after week after week
um
and then one day I went out like maybe
six months into this experience and I
was just gonna run for like an hour and
I had one of those days you're an
athlete you know those days where you
just feel like you just are bulletproof
and you can go go go and I just kept
running
and ended up running the better part of
a marathon that day like 24 miles and
I'd never done anything like that before
despite having been a swimmer I'd never
been a runner and that was a real
watershed moment where I thought wow
like I feel really good I didn't know
that you could feel this good certainly
not at age 40 and that got me thinking
about potential and I'd never really
realized my potential as an athlete in
college because alcohol really destroyed
my swimming career and so there was a
sense of Unfinished Business there but I
just wanted to see what I was capable of
and so that
um that set me on this journey to find
experiences where I could tap into that
and that's where I discovered this whole
world of ultra endurance and these crazy
races and I became fascinated with that
and ended up competing in this race
called Ultraman which is a three-day
double Iron Man race and that's the race
that I ended up distinguishing myself in
and and really the instigating point in
that was reading an article where David
Goggins had done that race back in
2006 I think and it was the story of how
he got through that race that really
inspired me and because he wasn't the
traditional endurance athlete triathlete
I was able to convince myself that if he
could do it that maybe I could and that
set in motion me uh training for this
race and and and uh and competing in it
a couple times I've had two guests come
here and tell me that we're in a comfort
crisis
and what they mean by that is they say
that we're kind of optimizing our way
um away from comfort in every sense of
the word we're like you know we live in
these sort of room temperature rooms
where we can go on a piece of glass and
get someone to bring us our food in a
metal car right to our doorstep and wet
where and in fact discomfort
pressure is where our growth our health
and all of these things I'm fulfillment
in many cases comes from
doing an ultra endurance race is for me
you know the one of the epitomies of of
pressure and discomfort and sitting with
that and accepting it
do you believe that
more of us should be making ourselves
uncomfortable in that context more often
and that there's tremendous value in
that I think about it when I hear like a
Steve when I get on my bike and
and just ride and just see and push
myself see what I see where I can take
it 100 percent
you don't grow unless you go out of your
comfort zone and that's in every facet
of your life if you want to become
smarter you have to read books or go to
school like that's not always
comfortable there's a million different
varieties of this but yes we are in a
culture that prioritizes comfort and
luxury and it's all about making our
lives easier
ironically what makes us happy is
putting ourselves in difficult
situations not so difficult that they
capsize our lives but difficult enough
that we're testing ourselves and we're
grappling with obstacles and we're
overcoming them and on the other side we
feel a boost in self-esteem we feel more
ourselves we feel more alive and we
experience growth and connection with
self and connection with other people
this is the stuff of life and yet it is
not
the way that Society is constructed to
we have to go out of our way now we have
to seek the it used to be this was
everyday life just to survive right and
now we actually have to pay money and
travel to places to have these
experiences what's so amazing is is that
you know when I started doing these
Ultra races they're they're all very
kind of like low-key under the radar
there's not a lot of media attention on
them
um you know it's a subculture that has
been around for a while but in the last
decade we've seen an explosion in
interest uh in in like doing 100 mile
races like there's lotteries now to get
into a race where you have to run 100
miles like if you told somebody in 1800
that this was going to be the case they
would think you were insane right so
what does that say
it tells us that we feel nourished by
doing hard things that they're that we
are extracting value from those
experiences that we don't get in the
mundanity of our everyday lives and yes
we have to consciously
extract ourselves from the Comforts of
our environments and put ourselves in
those positions but the good news is
there's lots of those things right now
it's insane how many marathons the
London Marathon was the other way like
how many thousands of people ran it and
then there's a Spartan Race and there's
just a million of these things now that
didn't used to exist because the human
Spirit needs it it demands it and we
have too long deprived ourselves of
these types of scenarios that doesn't
mean that you want to be unsafe or put
yourself in Peril but
um
I just don't see any other way or any
other path
towards becoming the better version of
yourself without placing yourself in
scenarios in which you're tested because
succeed or fail you have an experience
that's going to teach you more about who
you are what your limitations are and
what your capabilities are
the popularity of these um endurance
races and even things like
ice plunge pools and stuff sure all
these things that make us feel really
uncomfortable again it reminds me of
what I said earlier about the um because
the there's been a real rise in sort of
social media and the digital screens and
all of these things now people are
looking for places for community so
bowling alleys and in real life events
have increased and in the same way
because we've optimized Our Lives to be
more comfortable and easy now there's a
booming industry around things that make
us feel uncomfortable you said I didn't
get into Ultra Endurance Sports to win
races beat others or stand Atop A Podium
I got into it because it's the perfect
template for self-discovery what did you
discover about yourself
and also I think it's probably important
to say to people you're really really
good at this Ultra endurance stuff like
we haven't quite gone through your CV
yet but I mean I've got a list of
accolades that you've achieved and
you're you're one of the the best at
this so
I think that's worth saying before we
proceed yeah thank you for that I mean I
I've learned
so much
the amazing thing about
endurance Athletics is
you have to spend a lot of time
with an elevated heart rate that's not
so uncomfortable that you can't
perpetuate it for hours and hours and
hours but it's just uncomfortable enough
where you're sitting
in that discomfort and you have to
develop a tolerance for that so what it
does is it teaches you how to suffer how
to manage pain
but also how to be with yourself like
when I was training for these races I
would go out like all day alone and it's
just you your breath and your mind
and at that time I really was trying to
figure out like
I can't be this lawyer anymore like what
am I going to do like all I know is I
really like doing this this is not a
career path this is not I'm not going to
support four kids doing this thing that
I love
but
it is bringing so much value to me that
I just know I want to keep doing it and
I'm going to
pay attention and pull whatever threads
show up and what I learned
through this journey of training most
importantly the training the races are
just you know a demonstration of what
you put into getting to that point
um
was on a surface level
as an athlete
I had a lot more to say than I than I
ever believed that I could I was able to
do things I never would have thought
possible
um
and do it
in my 40s which is an age where people
think you're way past your Prime so
that was huge and like I said earlier
that opened up the possibility of
tapping into potential on other areas of
my life but I also learned that when
you cultivate and nourish that thing
that is bringing you Joy
and you pay attention to the subtle
voices that are telling you this feels
right
when you commit to that
completely
that will set you on a journey that will
lead you to a place you can't possibly
imagine
when I put on the running shoes for the
first time and just thought I love doing
this
could I have imagined that I'd be
sitting across from you right now having
a conversation it's ridiculous it's
Preposterous so
what I learned was
the power of connecting with the heart
as somebody like yourself who lives in
their mind and Prides themselves on
their intellect and their analytic
abilities understanding the limitations
of that and finding a way to really pay
attention to those kind of more
ephemeral ethereal uh
messages that one will receive when
you're really quiet
you're really honest with yourself and
you're committed to taking actions that
are in alignment with that in a way that
maybe you never prioritized before and
that has been a path that I've blazed
for many years at this point that has
caused suffering and hardship but also
beautiful creative offerings and you
know a life that I could have never
imagined for myself
metaphorically it sounds like you you
almost ran away from your little career
in law
yeah I guess so yeah I guess so I guess
so uh you know the law in me like how
did that I don't like conflict I don't
know how I became a lawyer in the first
place like I just you know I I I could
will myself to
be be the lawyer that I was but it never
felt right to me and I knew that I
wasn't in the right situation for myself
and it took me a really long time to
walk away like I probably walked away
from it over a very extended period of
time it wasn't a very dramatic split I
was trying to figure out from the point
of when you start doing the ultra
endurance racing
to the point where you get into sort of
financial hardship 45 years old you
launch your retro podcast you've got
this law job you start Ultra racing
there's financial hardship
is that because you you quit the law job
or is that yeah
because I was a bad lawyer oh okay no no
what happened was so I I did exit like
the big Law Firm thing but I continued
to practice law as a solar practitioner
and then in a couple different
um incarnations of Partnerships with a
couple people but as I got more and more
immersed in the ultra world my
enthusiasm and interest in my law
practice continued to dwindle and I was
my own boss at that point practicing law
so not a lot of new clients coming in
right
um
I was still doing it making just enough
money to get by but wasn't doing great
because I just wasn't into it but I held
on to it for a very long time and when
you're holding on to it it's hard to get
into the new thing until you're really
willing to let go of the other thing but
making that transition was very
challenging even you know after Finding
Ultra came out uh I I completely severed
my ties with the law at that point but
there were the phone wasn't really
ringing that much and there wasn't a lot
of opportunities coming my way and it
took a lot of patience and faith and I
did the podcast for years before we were
able to monetize it or do any kind of
ads or anything like that I just did it
as like a fun hobby or project what was
it like for Julie during that period
between sort of 2008 and 2015
things are really tough financially
um
you almost lost your house couldn't pay
a lot of your bills had your cars
repossessed yeah it was very difficult
um she was really the strength in that
equation because there were
multiple occasions where
I couldn't take it anymore and I thought
this is ridiculous I need to go back and
get a law job
what kind of head of household or you
know man of the house am I if I can't
even pay the bills and I'm chasing this
Fool's errand in this direction of
trying to do these creative projects or
be this athlete like who who the hell do
you think you are and Julie was the one
who was like no
we've come too far for you to move
backwards and the answer is that you are
seeking and the solutions to the
problems we Face are only going to be
found by continuing to blaze the path
that you've established for yourself and
she had a conviction and a belief and an
ability to see the more kind of
developed actualized version of myself
that I couldn't at that time and without
her strength her faith her conviction I
definitely would have abandoned the path
but she was in all the way and she would
say these things are just things
you're definitely on a path
that you should be on I can I can see
that and I want that for you and if we
lose the house we lose the house cars
are cars this stuff comes and goes but
we're together and we're we're gonna
we're gonna walk this path this is what
we're here to do which is a
amazing thing for a partner
to say to you to have that kind of
belief in you
is such a gift
so I just can't
emphasize enough
how powerful
um
she has been like in this whole thing
of all the things you've accomplished in
your life of all the things you've done
what does she mean to you
I mean she's she is my you know partner
in all things she's my North Star
she's my spiritual counsel
um she's my mirror yeah
um
and you know we're normal people with
kids who you know
bicker and argue and have the same kind
of issues everyone else does
um
but she's a really special person
really special
it's really it's really something when
someone can see the potential in you in
a way that maybe you can't see it
at that moment in time or maybe you
don't quite believe it it is such a gift
you know they say
um the greatest gift you can give
somebody is your attention
but if you have somebody in your life
who believes in you so thoroughly that
they can see past whatever situation
you're in or whatever
faults you have or things that trip you
up and holds a vision
for that better version of you and not
only holds it for you says I believe in
you they're not telling you what to do
or how to do it
they're saying I believe in you and I
trust you to find your way towards that
person and I am holding that for you in
my
daily Consciousness in my sleep and my
thoughts and my prayers that manifest a
very powerful energy yeah
so it's a curious idea that someone else
can manifest your life for you in a kind
of in an inadvertent way I've
experienced that as well there's been
moments in my life where my partner has
said something to me I've heard what she
said I didn't believe it necessarily
myself but because she believed it that
I could do that
maybe it did change
something in me maybe it did make me go
I trust her and she's smart and she's
usually right and she's telling me that
I can do this thing so maybe it is
possible hmm I can remember so many
conversations over 15 years where
someone said something to me about what
my future will look like and because I
trusted them
um I think it helped that future become
a reality sure I mean just imagine the
young person
who uh you know has the opportunity to
be with a certain teacher and that
teacher says you know you can do this
like you're good at the like there's
countless stories of people who win
Oscars and get up and thank their
whoever who said you know you should
keep doing that thing and you know those
are those are really powerful
um
you know gifts that we can give to other
people
he believes that if you follow your true
path the universe will support you
quote I read about you as well yeah I do
I do believe that
um that's been my life experience I've
seen that manifest in in many people
um that I know over the years a lot of
people in recovery and that doesn't mean
that it's easier convenient or on your
timetable
um I I would say that the the path that
I've pursued has been the hardest path I
could have imagined it's the most
meaningful and fulfilling but it didn't
happen overnight it happened over the
course of more than a decade and
it required a lot of conviction and
faith and patience and pain
we have to you know we had to lose a lot
but there's that adage like you can't
you know that you can't be a phoenix if
you don't burn in the Flames first right
and I feel like we had to burn in the
Flames or burn off you know the residue
of
whatever in order to be reborn to do
something different and I think when you
have run that type of Gauntlet and you
emerge on the other side of it what you
have to share with other people is all
the more kind of poignant because it's
your own lived experience and it's
authentic and real
I'm a big Manchester United fan and I
know that's slightly contentious thing
to say because not everybody here is a
Manchester United fan but right now
we're not doing great so we shouldn't
threaten you too much but in June I will
be playing at Old Trafford which is
Manchester United's home ground for a
charity match called soccer Aid honestly
if I'm being completely 100 with you it
is an absolute dream come true
regardless of my performance on the day
just getting to run out on that pitch as
a childhood lifelong fan of that club is
a huge honor so I've been playing
football about four times a week in
preparation to get my fitness up and one
of the most important things when you
are training is to be nutritionally
sound that is where heels rtds have
played a role in my life over the last
couple of weeks every time I train I
have my heels that day to make sure that
I'm getting all of the essential
vitamins and minerals into my body so
that my body can convert it into what I
need to be successful on and off the
football pitch if you're getting in
shape if you're trying to be healthy and
you've not tried Hills RTD ready to
drink give it a shot my health is always
going to be my first priority so when my
life becomes
ready to drink is my companion
so many chapters in your life rich
so many of them we've been through
pretty much all of them so far and we
arrive now at today
now if I was to ask Julie what the next
chapter looks like or or you
I know you know it's funny because when
people ask me this I my instinctive
answer is I don't know but I'm gonna you
know do my best at what I'm doing now
but if you were to try and if you think
back to your mission the mission you
described at the start of this
conversation what do you think the next
chapter is for you
that's a great question I think for me
the challenge and the opportunity comes
from
learning how to let go of striving and
step into a place of allowing
rather than
being this animal of self-will who's
pursuing and achieving and pushing and
um
and and and really kind of in their
ambition
to manifest something for
Financial Security for legacy whatever
it is to ease off that gas pedal
and just be in a place of ease with
everything where
it doesn't have to be hard and what
would it feel like if you if you didn't
push
but you still did the thing would you
still be you would you feel like you
left something on the table because you
didn't suffer to create the thing that
you share with the world
and I think that is
so hard for me and I imagine might be a
difficult thing for you to digest for
yourself right because
we both know if I go out and I push
really hard I can do something and I can
make it great and I and and I'm pretty
sure what the result of that is going to
be
but what if you created out of a sense
of joy
and you didn't have to exhaust yourself
in doing it and you could enjoy your
friends and your family and live a rich
life without the stress that you place
upon yourself or the pressure or the
people pleasing or the need for any kind
of external validation so that's the
mountain that I'm trying to climb right
now and I would say that I'm not doing
it very well why'd you want to climb
that mountain there because I think that
there's a lot of of wisdom
um
in being
more in flow as opposed to
willfulness
and I think that
um
there's a peace and a happiness
to be found there that
I'm probably missing in my life right
now
uh
and because
it's new territory to be explored I know
what it's like to do this other thing
and it's exhausting and it's not
sustainable
and I believe that there is a better way
over here
so am I in enough pain with this where
I'm willing to entertain the possibility
of trying something different or am I
holding on too hard to this
old modality
and unwilling
to embrace the possibility that the
results and the the
the fullness of life
could be better
by
this different way of approaching things
has there been personal symptoms that
have encouraged you to
seek out another way of being
sure yeah uh
I have tiptoed up to burn out a couple
times with the podcast and that's been
ameliorated by now having a staff of
really talented people to help me
because
I was a control freak perfectionist who
tried to do everything myself for too
long to the point of it just being
completely unsustainable
to now having
people that I Empower to do a lot of the
work that I used to do and who now do it
very well which has freed up my time
and I still find myself with this
sense that
success has to be earned and the only
way to earn it is to inflict pain on
yourself
and if you're not in pain you didn't try
hard enough
and it would have been better if you
suffered more and I think that's a lie
and I want to find out if it's a lie or
if it's true
thinking back to endurance racing it
seems to be that it might be true you
know you achieve that through pain sure
discomfort seems to be the the first
hurdle to
all the good places but actually that's
very comfortable for me
the real discomfort is to
see what it would be like
without the suffering
that's harder to do yeah it's harder to
do for me aren't you
I often ask my guests are you driven or
are you being dragged because saying
you're driven is a nice way to frame
yourself that's like an intentional
person but so often we're actually being
dragged by the insecurity the shame that
desire to be enough we're like we're
strapped to the end of the Lorry and
it's flying down the highway but we
think we're in the driving seat you know
and I think in so many facets of my life
right now I know I'm well I suspect I'm
being dragged but I think I'm being
driven and I'm portraying it so what
would an example of that be even the
podcast you know do I do I have to be so
like neurotic and obsessed with
everything and every detail you said it
before we started you're very obsessed
about the detail the fact that when we
do the podcast in La we have every book
is the same in the same world you know
that's insane I mean it's a great story
it's very entertaining but it's
bananas but for me it's I mean I'm
probably gonna try and justify it here
but for me it's about I know that the
small stuff is the stuff that most
people don't think about so it's my
place it's where we find the opportunity
but generally of course I think about
all the things I do all the businesses
all the details to the point of some
level of suffering there's definitely a
cost to my personal relationships when
at Sunday when I'm on a date with my
partner and I get a message and
something's not quite right and then I
lose 30 minutes in despair like silent
despair to myself in my head I just kind
of I leave the the dinner table
that's not a great way to live right I
relate to that deeply
um so I'm right with you and locked up
with that
um but what if you were to say okay
but then okay okay so let me try and
justify then everything the whole house
of cards caves on top of itself and all
the good things in your life disappear
yeah that's what I think right yeah
I know and I'll say well all our
ancestors they built these skyscrapers
and this AI stuff and these cameras that
we're using so we're innately meant to
struggle forward that's hardwired into
us it's why I'm here my ancestors
struggled forward they built buildings
and civilizations and they left that in
my genetic code there's a little message
saying you too shall struggle forward
Stephen you two shall be wired to climb
upwards
do you feel that
uh
to enjoy your life
is
an Indulgence that's fine for other
people but you're on a mission so you
can uh
you can like have a different
relationship with those aspects of life
that other people find important I think
so yeah yeah yeah
no I'm like I'm just I'm just seeing if
you see the world the way that I do you
know what I mean but uh what are you 30
how old are you I just turned 30 years
yeah so I'm 56 dude you know so check in
with me and and what advice did you give
me
we've got the same mindset look I think
it's great that I'm all about the
details
and I just want to say for the record I
shared it with your team earlier I think
that what you have built here is
extraordinary I have so much respect for
uh not only the show the way you comport
yourself uh the way that you are curious
about the people that you talk to
um and the fact that you've built this
incredible uh audience in such a short
period of time and the integrity and the
you know the the the the quality is is
fantastic you know so I've been a fan
um
and a lot of that is because you are
attuned to the details and I see that in
you and I think there's something
beautiful and wonderful about that the
trick is to not allow it to become toxic
to the point where it starts to
denigrate the quality of your life so
can you
you know toggle it such that you're
still pursuing what's important to you
in a way that's sustainable because
you want to be doing this for a long
period of time right so after five or
six years or ten years like what is your
relationship to this thing going to be
and if it's not sustainable now where
you feel drained at the end of the week
rather than energized then maybe you
look you're a brilliant business person
look at the model and figure out how you
can
tweak it so that you can stay in love
with the process and I think
for me uh it's all about
enjoying it for what it is and detaching
from all the externalities like if I
start looking on
Spotify or apple where the ranking all
that kind of stuff like I know that I'm
in a dark place right I shouldn't be
comparing myself to other people I
should just be present for the
experience of having these conversations
and trying to deliver value to the
people who are taking time out of their
day to listen and
that's it
doesn't have to be any more than that
when I get caught up in that other stuff
is when I uh start to
make
decisions that begin to become out of
alignment with the mission
thank you
thank you for that advice
um and thank you for such a rich
wonderful conversation
um I think especially that that closing
piece of advice is something that will
resonate with everybody and I thought a
lot actually starting up my career as an
insecure young man that wanted to make
millions and thinking that life was this
kind of
Sprint where you can Sacro everything
else can wait including relationships
social you know relationships romantic
relationships family
will I get this thing getting the thing
and realizing that the kind of the thing
just moves forward off into the distance
like a mirage and then I've read Simon's
book about infinite games and thinking
okay how would I design every system in
my life so that I could run those
systems for 40 or 50 years in a
sustainable way and this is one of them
this is one of the ones this is one of
the systems this podcast is one of the
ones where I need to continue to remind
myself that
I need to design it in a way that is
sustainable for 40 years of my life
including the period where I have seven
kids and a mortgage and a wife that
needs me to be there and and also not
just for me but for all the people that
work here as well
um
and everyone can relate to that
especially people that are being dragged
sure in some way
beautiful we have a closing tradition on
this podcast where the last guest leaves
a question for the next guest not
knowing who they are leaving the
question for
you get a 60-second phone call
with a previous version of yourself
what do you say
you then get to pass the phone to
someone who is in your life at that
moment and you get 60 seconds to speak
to them too
what do you say
what'd you say hmm
I think I would call up
the 18 year old version of myself
and tell him
that it's okay to be who you are
that you don't have to live up to
anybody's expectations
that you don't need to earn love
and the best gift that you could give to
yourself would be
to find out
what you love to discover the animating
Force within you
and above all to nurture that
to mute out all the noise of the
external world the social and familial
pressures
and to just find a way to be comfortable
with who you are because Who You Are
is a hundred percent fine and you don't
need to be anyone else in order to be
accepted or loved
and the corollary of that would be to
not get caught up in
trying to make decisions about the rest
of your life or your career path at such
a young age but to instead
explore and invest in as many
experiences as you possibly can to Live
Lean
and to be adventurous
and then I would say put your mother on
the phone
and I would tell her
I know you love your son
but you gotta leave them alone
and let him be him
why would you say that
how many hours do you have
[Laughter]
I understand
rich thank you so much for an incredibly
very life-changing conversation in many
ways but for your honesty and your
vulnerability and for all the work you
do because it's people like you that
pave the way for what I do here and
we're big fans of yours I mean that's
why I reached out to you and wanted to
have you on the show so I'm so
privileged and honored that you said yes
um I freaked out a little bit when you
responded because I've spent a lot of
time watching a lot of your episodes I I
love um the way you do what you do the
Integrity in which you do it shines
through and everything you've said to me
today about authenticity and being more
aligned with yourself now makes perfect
sense it makes sense as to why what I've
seen from your content and the way
you've lived
um and the man that I've met today I see
the alignment so thank you for the
inspiration and thank you for the
kindness and generosity today I really
appreciate that Steve and that means a
lot I have crazy respect for your
mission and what you guys are doing here
and I've loved watching your trajectory
and it was a real honor to come and talk
to you today and man you're good yeah
you were like I was like wow what do we
talk about
[Music]
quick one some of you will know that
this podcast is now sponsored by the
incredible Airbnb I'm a huge user lover
and customer of Airbnb every time I go
away on a trip whether that's work
related or it's a holiday Airbnb is
always my go-to but have you ever
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me explain further perhaps people are
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you have a spare room why not Airbnb it
or your home office is free right now
you're working away from home during the
week you can Airbnb it honestly the
possibilities are endless I've Airbnb
one of my Apartments before and it's a
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recommend you all to at least check it
out that extra space you have that extra
room it might be worth more than you
think so to find out just how much it's
worth search airbnb.co.uk host that's
airbnb.co.uk host
check it out quick one as you guys know
we're lucky enough to have blue jeans by
Verizon as a sponsor of this podcast and
for anyone that doesn't know blue jeans
is an online video conferencing tool
that allows you to have slick fast high
quality online meetings without all the
glitches you might normally find with
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jeans basic is essentially a free
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changing the game for myself and my team
without compromising on quality to find
out more all you have to do is search
bluejeans.com and let me know how you
get on
[Music]
oh
[Music]