How Do You Pivot Your Life for Success - Jason Shen is RightOffTrack | Anya Smith

MY MESSAGE IS OFTEN LIKE
FACE PLANTING HURTS LESS THAN YOU THINK
AND BELIEVE ME
I FACE PLANTED A LOT AS
AS AN ATHLETE
AS A PROFESSIONAL
I HAVE BEEN LAID OFF RIGHT
I'VE BEEN SUED
RIGHT MY COMPANIES ARE SHUT DOWN
RIGHT I'VE BEEN
I'VE FALLEN ON MY FACE
I'VE BEEN HIT IN THE FACE
AND IT IS PAINFUL
THERE'S NO QUESTION
BUT THIS YOU KNOW
WE TALKED ABOUT STRUGGLE
STRUGGLE IS SO IMPORTANT FOR EDUCATION RIGHT
IT'S THE STRUGGLE THAT YOU HAVE IN YOUR CAREERS
AND THE PROFESSIONAL MOVES THAT YOU MAKE THAT TEACH YOU
WITHOUT THAT STRUGGLE
YOU'RE ACTUALLY NOT GONNA GET BETTER
SO YOU KIND OF HAVE TO DO IT
going off track is taking a chance in yourself
following your poles of curiosity
it's making your own decisions
the most wonderful adventure
hey friends
welcome to another adventure with Right Off Track
your favourite entrepreneur podcast
but we dive deep into transformative minds
of purposeful entrepreneurs
I'm your host Anya Smith
Today's episode is all about the art of pivot
whether you're running a startup or simply
trying to steer your own career in a new direction
we'll also get some insights into how ADHD
can influence such a journey
it's real talk that you don't want to miss so
who's adventure walking us through this high wire act
meet Jason Shen
a serial founder
author of The Path to pivot
and executive coach of over 14 years of experience
Jason's also a Ted speaker and NCAA gymnastics champion
and even a presidential innovation fell under Obama
he's redefining what it means to be resilient
all while breaking world records
and being one of the fittest people in tech
from his venture back startups
to navigating his career of ADHD
Jason is here to empower you to adapt
we invent and
of course pivot
so let's get this adventure started
welcome to the podcast Jason
so excited to have you here
it's so wonderful
uh we got to connect
through some of our connections through
through meta
and I'm so happy to be here
my pleasure is and Jason
there are so many incredible things in your background
and I want to talk about the book that you written
and the focus on pivot
but can you share a little bit about
how you navigated this journey prior to all of that
prior to Meda
the lead you to now
this coaching journey that you're on
so yeah I mean it
it was definitely a whole journey
and I'll kind of hit
give you some of the highlights
and then we can dig in
in different places
but you know
I am a first generation immigrant
I moved to the United States with my family from Suzo
China to the New England area
those cold uh
New England winters is sort of how I got raised
um I started doing gymnastics at a young age
which was really good for a high energy
hyperactive ADHD
kid like myself really love science
so I went out and I got the opportunity to be a student
athlete and study at Stanford and do gymnastics there
study biology
that's why I discovered startups
I'd always enjoy technology
but I took a few software engineering classes
realized that wasn't for me and
this helped me see that there are other pathways into
this industry
so I went and worked at a startup out of college
started my own company
we went we went the y comedy program
raised you know
a million bucks and then hit a wall and
and you know
tried to pivot and failed to pivot actually
and so that was kind of an interesting uh
wind down experience
move back to the East Coast
was a little bit
kind of ashamed and
kind of wanted to run away a little bit
worked at a couple companies
including another startup and then at Etsy
and in a product management role
so I switch from marketing into product management
in that role
then found an engineer at that company
and we started another business on hiring
and hiring place on their abilities
and not just the resumes
which you know
I think we all have so much um
desire to see more of in the world
realize the business wasn't going the right direction
tried to pivot
this time the pivot was more successful
I Learned a lot of um
I I kind of operating on instinct
at that point
but a lot of those lessons
I've come to understand and document more
that pivot went into
gaming and esports
and that companies acquired during the pandemic by um
then Facebook now meta
and I got to spend three years as a product
manager at meta
leading across um
internal tools teams
as well as consumer facing product teams
and I had always been
interested in
human development and leadership development
I worked with an executive coach during my second
a batch of startups
that was super helpful to me
I started coaching on the side while at meta
and I just came to like
love that more than being a PM
even being a founder
or just that it was
the kind of the right thing at this point in my life to
to enter that
and so I left after three years at meta
I took a bit of a sabbatical
and now I'm coaching full time
you know getting
getting the
the the bear
and real blast
so that's a little bit of
of my journey
wow so much
so the pack there
is incredible
I'm curious
a lot of times we hear that we should be following
you know one direction
stay on course
don't try be very focused
how do you feel about that
advice in your life
look it's funny
because I'll
I'll speak for the perspective of being an immigrant
but also the
the child immigrants right
my parents lives
are interrupted by the cultural revolution
they had to
had shot to kind of get back on track
which is to
kill it in the standardized testing of the era
and then they had the opportunity to come to
the United States
which is was a boon
it was it was grand adventure
definitely not
unknown thing
but once they made that leap
they almost wanted to conserve and protect
and secure and say
let's do the safe thing
now we did we
we on black we
we hit the Jackpot
so you know
don't go and gamble it all away
that was kind of their perspective
so there was a lot of like hey
you should take a safe route
stem fields always
tend to do better
their safety
and hard technical skill
my dad studied education
but he was always obsessed with
making sure that I got
hard technical skills
because that
that would make me playable right
meanwhile you know
I kept switching you know
it was a sign that I had a new idea
for what I wanted to
major in or
do as my career
every couple of
you know weeks
in my first couple of years of school
and biology
was just like the thing that
that kind of um
covered enough of my interest that I could like
draw a circle around it and
and major in that
right and my
my career has
been changing jobs
between one and three years right
I've never done more than three years at a company and
so for me personally
doing the straight and arrow was never gonna work
it was just not going to work for me
and for some time
I was kind of ashamed of that
and there are some days where I am like
man if I just stuck to something five years ago
10 years ago
how far along would I be with that
and there's
there's still so much ice out there about that
and that's not to say that that can't work
for some people
but it doesn't work for me
you know what I
what I believe yes
everybody has their own journey
and that's what we should honor
but when you describe all these different experiences
I can imagine that you Learned something about yourself
through each one of them
they can take away into a different experience
often times
we think that if you start something new
that you're literally starting from ground zero
but you're not you
you devolve as a human being through each experience
so I'm curious
as this journey unveils
you go through these competitive schools
you physically challenge them
what motivated you to
constantly rise to that next challenge
whether it be in different areas
I think curiosity has
is really been motivating factor
curiosity and camaraderie right
gymnastics is a very individual sport
when you're doing it in the club environment
which I was in
sort of you know
middle school
high school
I was competing in the junior nationals
as an individual
like I had a team
but they were really just other competitors who
trained with me right
it was only when I got to college
I got to NCAA
where we really had
that we won our loss as a team
we had the same name on the back
or on the front right
we have the name on the back
but same name on the front
and we won our loss as a team
and I remember one of the
the sort of
athletes who had had great individual success
but the team at the time was not very strong
and he told all of us
he said I would give up all my individual accolades
for a chance to win as a team
which you know
my my class did
the first class to win a
national title for Stanford in 14 years
we had a great run in the 90s
and then there were kind of nowhere
for a number of years
and then we kind of started building up in
in my last year yeah
we we we won the championship
and we've won it
you know three or four times since
so I'd like to think that we kind of started a thing um
and build some momentum but
but so that's
karate was that I
I wasn't just it to win for myself
I was in it to win with
um my teammates
and then curiosity is really around um
what what's possible
what's out there
what could happen
you know the
the Guinness World right
like it's such a funny story how that happened
I had decided to start um
doing 30 day fitness challenges
so every month I would pick a challenge
pull UPS you know
one mile run
and I would
do at the very beginning of the month
and then I would train over the course of the month
and then I would like um
try it again at the end of the month
and if you go on YouTube
you can type like Jason chant fitness challenges
you'll see these like little videos that I make
I'm like alright day one
let's see how I do
and then like
and it's like okay
it's like all wrapped up three days later huh
yeah you know
and you would see these incredible improvements
and you're like oh wow
when you like
really try to do something you better
you get better
and then around that time
one of the I was like
let's let's do something related
let's look up for like a push up variation
something fun
something interesting
I found these like Aztec push UPS
which never heard of um
didn't know what they were
I don't know why they're called that still but they
they were push up
or you would push off your hands
and you would touch
your toes in the air
and then kind of land back in the push up position
oh touch your toes oh
very like an explosive
movement yeah
and someone has set the record for it
and I was like
you know what
let's let's give it a shot
and like part way through the
month I was like
you know what
you know it turns out there was like a record for it
I was like what is this
and I'm like
already kind of close to the record I was like
you know what
you could beat this right
so I started
you know looking into
the whole process of getting validated as a record um
setter for Guinness
and the pro you know
you have to get it taped
different angles
judges witnesses
all that stuff
and went through that whole process
and I went back to Stanford actually
and it was at gymnastics meet
and there was like an intermission
I would became like a sideshow
entertainment
they're like okay
everybody's taking a break here
and we got alumni Jason
Sharon you know
this is just me
like living up my old glory days
yeah yeah yeah
yeah um and
and I ended 31
as I push UPS in one minute
and I ended up doing 50
so what wow
that was quite a
quite a jump
and it's still
it's still held
so 2014 set the record
still going almost
almost 10 years
next year will be 10 years
so that's neat
and I have the humility to recognize that look
I was doing this as a
retired gymnast
I know that
in my you know
prime as a gymnast
I could have done
way more than 50
and I know plenty of other
athletes in my level
who could do more than 50
but they've got
better things
to do with it
than go after a silly record like this right
but you know what
a record's a record
and I'll take it
and so now we talked about
the things that got you through
these physical achievements
what about the aspirations
that you had
outside of the physical realm
how did you
how did yeah
so you know
starting our first company um
it was a matter of so many things
coming together
circumstance
I had started
I had you know
started a nonprofit while I
was in school
and that kind of
happened while I
was injured
during my gymnastics career
and I had a year where I wasn't
training as much
and I got involved in a student group
dinner starting
a nonprofit organization
and then one of the
students from that group
we moved in together
as roommates
I made a third roommate who
who we sort of found
who was also
all three of us
it was like a sitcom
you know it's a
apartment in San Francisco
three you know
Asian guys living in apartment together
all working
at startups
two engineers
one like a business guy
and then we start
talking about oh
what we started company together
so it was really
fortuitous at first
go around and I
don't think I would have been able to do it if we
hadn't got into
that y Conray
program that gave that initial funding
because I had
almost no money to my name you know
and I was like
I could not quit my
job and like
work for six
months without pay
there's just
like no way
even if we weren't spending a lot of money
I just didn't have that um
so we were lucky
enough to get in
and kind of go on this whirlwind
adventure and again
curiosity right
what could we do
what would be possible
what would be interesting
what would be um
and and and to explore
other boundaries of technology
because there were so many new
ideas that were merging
at that time
Airbnb was becoming
you know it's
it's it's still an organization
but even in 2,011
2,012 is already like a
this is gonna be big
and what else is out there
that's kinda like
this thing um
we got to really
be a part of something special
it definitely sounds like it
and hearing
all of this
you make it sound so like
oh yes naturally
this happened
and they got to you know
challenge myself
I was curious
but the question I've
had to myself asked is
how do you help
people think big
because you
can do something again
to your point
if you don't think it's even possible
so if you don't think that
you can start a
start a business
that you can
start a startup
that you can
go for this challenge
you don't even bother starting
so what advice would
you give to
people about thinking big
and finding
the confidence
or resilience to
even go for it
yeah you know
I think there's a
couple things
one is you do you know
this podcast
and other kinds of
um media that
you have to
you have time
immersing in stories of
people who have
gonna undone big things
you know like
I was a good student
but going to Stanford
expose me to people
who had done a lot of
um incredible
things and started
companies while leaving
in college and
and all that
and you know
going through why
combinations similarly
you have these
people coming in
you have the
guy from Paypal
telling us about
all the ways that they
like narrowly avoided
like totally imploding
the company
and like having to like
get everybody together
to wake up at 6 a
m to like reset
the servers because
all the money
and everything
was locked up in this whole thing
and you're like
oh my God I
can't believe this is um
what happened
but but it helps
humanize that
these heroes
these people that
you know that
are sort of
larger than life
they really
you know aren't
so different from Uri um
their results may be different and uh
that's a matter of both
you know the
application
and they developed
the application of that skill in
the right sort of
direction and
of course locked
uh but when
you see that
you realize hey
you know this
this could happen to you
no guarantees
it'll happen to
you but your
life is gonna
go by anyway
time is gonna go by
anyway right
and we do live in a world
that has a lot more
safety nets
and more Protection than
maybe you know
the US versus
other countries so
and uh such
and so but but
so anyone listen to this podcast
I think has
a sort of social
safety network outside of
the government
but it's more
based on their community
and based on their
kind of professional
uh networks
that they're part of
and so the risk is a lot lower than they might
and of course
as I've gotten older and I have more responsibilities
it's not the same as it was when I was right
24 years old and could kind of just eat Costco ravioli
three cheese ravioli all day so good
so good but
but life life isn't go out either way
you know and none of us get out of here alive
um and I know that that's a little morbid
but I do think in my in my book actually
not to plug the book so early on
but I have a chapter called shoot the zombie
and it's from this phrase zombie startups
and so there's this idea that like
there's some companies that are like they
they're chugging along
kinda figured something out
it's going okay
it takes a lot of effort
kinda keep it running
but it's making some money
or it's getting some users and all that
but it's not really on the trajectory
to become that sort of breakout success
and that's when a lot of things start to hit right
cognitive biases
some cost already put so much into this
if I change now
I'm gonna lose everything that I had lost a version I
the endowment effect
what I created
what I have is more valuable than something else
even if it was like
if I wouldn't pay you know
$100 for this thing that I won't sell to you for $100
right like that
that whole bias
all these biases in place
and the whole point of the chapter to say
you have to believe in yourself
you have to bet on yourself
and you can recognize that like you know
significant outcomes are absolutely possible again
no guarantees that they
they they'll happen for you
but if you do this
you're for sure locked into a mediocre uh
circumstance
and you know
I I believe that everything to this deserves
better than a mediocre circumstance
whatever definition of mediocre is for them uh
and that the
the act and the pursuit of chasing that
that goal or direction or path is worth it
even if you don't ultimately reach it
yeah and then you said you had a lot of experience that
you know start UPS
and now you're coaching out
what advice would you give to somebody
who is maybe thinking about like
they're in the startup
maybe they're struggling
or maybe they wanna give some
what advice would you give them through your experience
like the hard work
the hard one
lessons that you might wanna share about
running a startup or getting through space
yeah you know
one lesson that I'm reminded of
and I was connecting with an old colleague who has
who would pivot and
you know um
made it through
but kind of like very
under very difficult circumstances is that
um there are times where you have to
get sort of an unreasonable
kind of delusional self confidence
and that there are moments when
if you're fundraising
if you're you know
interviewing for a job
or if you're um
kind of in a high pressure
sort of high potential reward situation
where you really have to develop
the skill of being like I am
I am that person
like I'm absolutely the best
possible person for this opportunity
and you have to like
feel it in your body
and you know
my gymnastics training
my physical training helps me kind of like
get into that
state listening to music helps
moving your body a little bit you know
just like um
saying these things yourself that even you're like
is this you know
you what I like 100% sign
off on this with my logical brain
be like for the
when you're go at meeting
you know for the
the 30 minutes going up into that meeting
when you're walking in the
thing or you're you know
you're getting
you're at home
you're getting ready for the call
just pacing
listen to your favorite jam
be that rock star
embody that
it sounds silly
but so many
knowledge workers kind of like
feel like they're just a brain
housed inside of a you know
of chemicals
but where our body
first and foremost
so get that body pumping
get that body moving
get excited
and then channel that in those moments
so I think that's an important lesson
that it's gonna feel weird
it's gonna be abnormal
and you aren't gonna be like this
hopefully most of the time
that would be
there are that's how sometimes you get through
people because they
feel that of intensity and confidence like
we wanna go with this person 100%
I realizing that to me
what you're describing sounds like living of conviction
and I'm realizing that's something I've struggled with
because I had this preconceived
notion that doing so is pompous
maybe it's a little bit arrogant
but I'm realizing that
living conviction
serves the world better see
if you realize that
by living conviction
you can have a bigger impact
and it's not that you don't deserve it
or that you are not the right person
or you're not good enough
it's that those are all the delusions that I had
the real thing is that
the world needs more people to show up
and live with conviction
and I don't mean
conviction let's say
I'm the best in the world
like ah but
because I believe in what I'm doing
I'm trying my best
and this is important
and the world has so many causes that
can be improved by
we don't have like I say
an overwhelming
you know um
organs of happiness
there's not a pandemic
of overwhelming happiness happening
so we need people to show up
a conviction
on things that matter
and no that's not about
you know even
thinking that I'm the best one
but being like hey
I really believe in this
and I can make a difference
to me that we
challenging of it
and seeing it through a different lens
while still
seeing the points of being convicted
what I do has
really helped me live up to that
and feel more
closer to that concept of
that feeling
that's alien
or foreign or
negative absolutely
absolutely and
and your point about
you have to
this only works
or this works best
when you really
are pursuing something
you believe in
right if I were to go
and apply for a job as
you know chief
financial officer or something
you know I would
not be able to generate
the level of
convictionist sir
because frankly
this is not right for me
I'm not qualified
and I'm not interested
so uh there's
really not a
not the right fit
right and if
you find yourself
really struggling to generate that
level of conviction
a question you can ask
yourself is
is this the right
actual direction
for me you know
when I decided to
you know do
the acquisition into Facebook
it was partly because I was like
you know what
I don't know if I have another fund raise in me
right and so
as much as my journey
you can say
is like a lot of success there
there you know
the first company
we just shut it down even
didn't even spend
all the money
you know and we shut down
that's kind of like
you really gave up um
and and there are some
investors who judged us
for that right
and I you know
I kind of clear through
the shame of that
but there's still a little bit there
the second time around
I felt like
we had pulled the rabbit
out of the hat
we had had our bank account hit
like below zero
and then got
you know a little
bit of refresh
and I was like
you know what
it's I don't have it on in me
but I know I
and this is what I mean right
when you swing big
even if it doesn't work
out for you
you're gonna feel
satisfied with yourself
and you're gonna be
proud of yourself
when we folded
that other company
I kind of was like
we didn't even
like get to
the end of our rope
we just sort of like
fizzled out
where is this
when I was like you know
we gave it everything
and you know
the acquisition is
not like some
life changing
some money that I can just
go home and
not have to
to work right
so gotta go and
and make money
to support um
my family um
but I'm still so proud of what we
were able to accomplish
thank you for touching on that subject
I think it's so important
you the point
you meet early
is that people
that we see
doing something amazing
are all real people
and we have this
fake sense that
if we're struggling
then we're on
the wrong path
if we're trying something new
we're trying to start something
and we have self doubt
we're not like
we don't look
this is not a great Instagram story
and why bother
right when when
really the people
who do make it big
they all struggle
they all had to go through some challenge
there's not a straight line
and on that point
can you share some of
your biggest struggles
you mentioned
some of them
right now but
what would be some of
the biggest
mental challenges
or again the
circumstantial challenges that you
had to go through
yeah so you know
one of the ones that I think a lot about is um
we talked a little
bit about ADHD
you know as a kid
it kind of manifested in
not being able to pay
attention in class
gymnastics help with that again
sports is so
important to me
because it kind of like
clears some of that
body energy
so I can use my
my brain energy
I'll tell you about
two sort of like
more mental
and professional work
struggles that I've had
one when I was at
at at meta right
is just a delusion
of information
coming at you from
all directions
every direction
workplace post chats
calendar invites
you know there's
there's so many
someone somebody's
going live now oh
there's a Q&A poll
like you know
should I attend this
me it's like a
it's optional
or whatever
but like if
you wanna join this
you know circle
of whatever
there's just so
many things
you could just sit there
all day and look
at that and not do
anything um
and and then
there were these meetings
so it is incredibly
for someone
who is like
it was both
because there's always something going on
so there's always something stimulating
but then you know
it was hard
to prioritize
the work I needed to do
and get the work done
and do it high
enough quality
and you know
is this the right
with you know
sometimes we didn't have
I had managers
who were new to
the company
so they didn't have
the contacts
to give me about like
this is is this
good enough
is this what
we're looking for
and so I was
resourceful
enough to kind of
put something out there
and just be like
all right let's
try this right
but it is still
unnerving because
the organization
tries to push
you to kind of
do things in a certain way
and do things in
the right way
so you know
I don't think I
I had a perfect answer to that
I was on a lot of different projects
that kind of
kept me engaged
I I feel like I start
strong with projects
and then like as
time goes on
and some more of
the same old stuff
and the problems
just come out of my
I'm over it
I don't wanna deal
with this anymore um
and you know
what worked was
ultimate fan
I think I had a
manager that really
had been at
the company
for four years
really in an
IC role before becoming a
manager herself
so she kind of
was able to actually
and I had to
swallow my pride
pride right
she was younger than me
which happens
everyone intact
some point another
you're gonna
have managers
younger than you
starts on the
top you know
Mark was younger than
pretty much
all of his executive teams
for for all
all these years
and but sitting down mean like
tell me how I'm supposed to do this
which felt like I was doing my homework
you know I was like sitting with a tutor
and having my homework done with me
and I it like
there was a weird ego thing where I was like
I can't believe I'm just sitting here at 7 p
m at night having my manager like
talk me through this dock that
I'm supposed to have been able to fill out right
I've been in this role for so many years already
but that helps me understand what was
they were looking for
and she could correct my thoughts and real time
and it got better right
so I had to sort of
you know um
accept that
and that was
important lesson is that you're never too old
to learn right
I'm certainly
I'm certainly never gonna be too old to learn
so that's one lesson
and then you know
another one is I've been you know
with this book
right it was
I've been wanting to write a book for a long time
I I love books you know
I have all these books at home
my dad loves to read
he's written a book about you know
like childhood development is kind of like raising me
just like a little embarrassing
it's published in Chinese
so like thankfully
you know it's not like you just go by and read it
but it is a little bit like I raised this great son
you know like
here's how I did it
and I've always wanted to write books but
but I've never gone all the way through right
I've done like half big things
collections of essays really
really short things for like
and I did a
full book proposal that I put in front of an agent
and then when they said
oh you know
it's good but not quite for us
I got demoralized
and then I kind of like shelved it
so it's been a journey for me to
get to this point where I finally have something
we have like 35,000 words and it's
it's really significant right
it's really substantial
and I think it really addresses a problem
and there are a couple lessons there
right one is
there's a a tough
direct personal experience that I have
having started you know
it's not like it just took me a year to write this book
it actually took me all the times that I had to
do the first company
having not work out
do the second company
have it work better you know
try different pivots on the way
research pivots along the way
so I follow my curiosity on that
2 to set small goals
like I remember
saying to my
my writing uh
uh RIA I was like okay
let's let's keep it simple
10 chapters
thousand words super
super easy right
and and I'd like
and then that kind of like started to grow
but like that felt achievable right um
getting feedback I
I use this twit
like that's beta readers are needed
highlight in
like edit and
okay motivation
working with this assistant as well you know
she kind of contacted me
but she was contacting a lot of people
and I was like okay
you know what let's
let's try collaborating and make such a difference
especially as an independent operator now
to have these
people who are like
kind of on my team
right and we have
you know this back and forth
and we talked through
and she does some research now
like you know
through her notes
and we sort of work on together
so all of those
I had to like
you know ADHD is a lot about combining tactics
there's no one tactic
you have to like
you know timebox
you have to set milestones
you have to get collaborators
you have to get feedback
you have to find
find little games
play with it
you know sometimes you work on a cover
cause that's like
exciting to you right now
you know yeah
and but here I am at this point where um
I'm about to put it in front of a new set of readers
the white commentator alumni community
which is like a pretty
you know they're
they're they're friendly
but also not gonna
sort of accept anything that's
that's like very loud
so it is a meaningful moment for me and it's
it's taken all the different strategies
to get there
to even this point
so quick question
what is the app they're using for the Vader readers
cause I'm very curious
it's called help this book
and so you can
import a Google DOC
and then you send them a link
and then they can highlight it
and then you can kind of see it
almost like
a software tool
like retention
it makes sense
the guy was
software developer
he wrote The Mom Test
which is a really
really great book of
customer development
and he basically ran this process
but now he has his tool that lets you see like
oh people basically drop off after Chapter 4
you know like
you have all these highlights
highlights highlights
and you're like okay
so what's happening between Chapter 4 to 5
that's losing people right
and then you like
try to fix it
you do a new version
and then you
and then you compare version
3 with version 4
be like oh look
we you know
address that now
the gap is right
so so that's um
for that kind of thing
help this book
oh I'm excited
and then let's go
unwind a little bit
so the path to pivot
you mentioned that previously
you started
you know thinking about books you tried
but it didn't come
and culminate to something
now what made this
journey different
what made the intention behind a different um
so many things had to come together right
you know it's fun
I started a
ego in August
writing something
I did something called ship 30 with Tiki
Bush and Nicholas Cole
and it's like tweet
it's like tweet every day
for 30 days right um
but I decided I
was gonna tweet about pivots
because I you know
I was interested in this topic
and I haven't seen a lot of
people really
like covering this in a
comprehensive way
besides sorry
if I writing tweets
some of them
are about my
own experience
some of them
are about you know
other pivots that
are famous and well known
and and that
you know isn't like
a huge breakout from that
but that kind of like
sparked my interest
and I saw some feedback
and I was like
this is interesting
then I wrote a series of longer
essays about it in the fall
then I got bored
and you know
was also like
preparing to like
oh I you know
probably layoffs up and
and then you're like
okay you know
I gotta focus on my
actual day job here um
and so that kind of distracted me
and then I was like
getting ready to leave
and then you know
after I left
I kind of was like
but in my sabbatical right
the sabbatic will give you
more free time
and it kind of reinstilled
the interest in me
it's like yeah
I wrote some of these essays
I started getting bored with it
I trailed off
but having that risk
having that
way to come back to it
so that's the other thing
it's like if you get
don't feel like
like you said
at the beginning right
these experiences that
you have aren't wasted
it took me such time to get to
the point where I could talk about periods
because I've done them
and that's not something
you just like
do overnight
you can't just like
you know go and
and go to the store and
get a pivot
and be like
I've eaten a pivot
you know thank
you you gotta
you gotta return
it to be able to say
you've gone through them
and I've gone through too
so so I think similarly
these tweets that I wrote
these essays that I wrote
research that we did
that we never even published
you know it
all kind of comes back um
and so robs
the the the guy who uh
who created
help this book
and who has
like a whole
theory around
writing books that are useful
he has a book called Right
Useful Books
is like right
for the yeah
yeah you know
very straightforward
right for the
back catalogue
right for something that's gonna still
matter in 10 years right
and even if
the examples that I
provide may feel updated
in 10 years
are there gonna be
startups yes
are there gonna be startups that
are kind of
like going okay
but not great yeah
is there gonna be a
a difficult
that founder needs to make
about what to do
in that situation yeah
and is this
process of like
thinking it through you know
aligning that
decision with
your stakeholders
exploring it
before you make
the final leap
is that still gonna make sense
or is there gonna be like
a new technique
where you just
jump into it right
like you know
human psychology is
not gonna change
like it's still gonna make sense to
do this process
so like that gives me confidence that
even though this is
taking so long
and longer than I'd like
and it's okay
it's not this window
of like some crypto coin
launch that I have to like
catch the wave of
or else it's
all over hey
yeah you know
it's gonna there's
like this um
for a long time
and could you
divulge some of the
key things that maybe
you found or discovered
or that you wanted to share
it sounds like
the audience would be for
entrepreneurs
or is there also a broader audience for this
I think this the
the book itself is
very much written
for venture
back to start
of founders
but a lot of
the principles apply
outside of that
but you know
I you have to
from the lens of
this is explicit advice
for that audience
so the the key points are
um most founders
um let their sort of
mediocre success
lead them on
for too long
and then they
have this sort of
rapid flurry
of activity
towards the end
when they go
oh shoot this isn't
working and we
don't have a lot of time left
and then they kind of
throw Hail Mary
you know deep pass
and just hope
something happens
and that's the
that's the most
founders get into
the other alternative is that
you kind of like
like we did it
right you like
decide you're gonna change
but then you never
commit anything
you just kind of
like wander
off into the woods
and never come back um
and so what I
recommend is that you
start thinking about
pivoting sooner
but you actually pivot
slower um so
by pivoting
by starting that
decision sooner
you give yourself more time
which allows
you to be more about it
being more deliberate about it
you can make sure that
you're making
the right choice
you can bring everyone along
your other co founders
your investors
your team so
it doesn't feel so abrupt
and then it feels more
like logical
and coherent um
and you have
you built it
takes time to build
conviction right
you're not gonna
marry someone
the next day
after the first date right
most people don't
it's not the
recommended
strategy um
and and similar with their
your startup
ideal things
can seem good one day
and then not good
the other day
but if you give
yourself a little
bit more time
um so I explicitly say
you define a
like a 48 week period
where you put
your existing business
on maintenance mode
you don't like
completely shut it down right
um you just
kind of like
keep the lights on
or you know
service existing customers
fix any major bugs
and then you spend
70% of your
time on this
new area right
and you really
like investigate
and you explore
and you do research
and you you know
bring it all together
and then you have this
set date that
you put on the calendar
ahead of time
or you bring it
all back together
and you look
at everything together
and you say
how's the original business
going how about
all these new
ideas that we have
do we feel more
compelled by this
do we feel like
this gives us
a better shot
at that big
outcome if so
then you can
now double down
with a lot of confidence
or maybe you go
back to your original
idea with some
new insight that
you Learned or
new technique
or strategy
that you developed in this
like period of
exploration
and you can imagine
how this approach
would also make sense
for a career change
for other kinds of
changes that
you might want
to make in your life
don't kind of like
in an impulsive moment
just you know
throw it all out to
to start over right
give yourself a real
chance to like
sit with that
new direction
that new location
that new you know
position or group
or whatever
it is that you
are doing and then
and then to make a
thoughtful comparison
between those
having had some
distance uh
to to consider
it makes me think that
often times
we're so busy
doing and we
don't create
enough space
energy time
for reflection on
is this working
and could there
to be better way
so we get caught in
the cycle of
oh this seems
to be working
I'm doing doing
if I do more
it's probably
gonna get better
to become busier
we're doing more
but if we don't
question is
this working
is there a better way
on so many levels
whether you're
entrepreneur
a mom parent
grandparent
whatever you
wherever you live life
then we don't have
the capacity to make
decisions that
are best for us
without that reflection
and with this
book in mind
you mentioned
having that
time for reflection
and stepping away
and kinda refocusing
do you do that
continuously
on your cycle
or do you do that as
you feel like
you need to pivot
well you know
you you kind
of you know
opening here to
to to talk about
coaching yes
this go I have
I mentioned one
executive coach with my um
previous startups
I'd worked with
a life coach
in my early 20s
and I worked with
another coach today
who is you know
former money
manager turned um
coach Mariko
Gordon and all
of those um
individuals
are create an
opportunity
to reflect right
and and for me
we're so important
you know you see
some people talk about
journaling exercises
being really
amazing for them
if that's working for you
that's awesome
personally I've done
some journaling
it can be great
but it the the sort of
really sink in
until I have a
conversation
with someone
it's ideally
someone who's been
seeing me for a long
period of time
who I feel like really
knows me and
understands
what my goals
are what my
interests are and
and what I'm
trying to do
and that's what
I do as a coach
for my clients
right we it
is dedicated
for reflection
for problem solving
for you know
checking getting
more clarity
and being like
hey you know
couple couple
weeks ago you
did this is
really important
now you're saying
something is
really important
you know if if
if no one call
you out on that
then you just
kind of go from
one thing the other
and this just gives
you gently a chance
for someone to
say like well
which one is it
you know that this
from before
or this now
if it's this
now and you
thought about
it great but
having that
sort of space
that dedicated
can regular
space to do it
because otherwise
it's a spy right
there's so many things on
the counter
so many to do
so many things
that need your
attention that
when you don't
dedicate that space
it's hard for
us to create
for ourselves
that's why some
people hire
personal trainers
you show up
it's not like
you couldn't find
the workouts
online uh but
that's not the
the only reason
why you weren't with
the trainer
for them to tell you
how to do it
right absolutely
there's an element of
accountability
and I love that
you got into
coaching because
through the story
I'm sure all
listeners are
amazed for what
you've accomplished
and you've been
you've been
named pivot
and the mindset that
you've adapted
through it so
what's really
curious is that
you took all
this background
and you said that
your favorite
parts right
now is focused
on coaching
that that's what
you can bring
you to life
I'm curious
why has coaching
really resonated with
you and can
you highlight
some of the things
you do that
maybe feel unique
for your process
well you know
coaching is in my
in is in my
it runs in the
family runs in
the blood my
I told you my
dad's in education
so he's been
involved in
kind of like
students teacher
assessment student
certification
all that kind
of stuff in
the state of
Massachusetts
my mom was a
gymnastics coach
for many years
she coached
we were in the same gym
she coached me
she's coached
generations
of of um of
gymnasts so
that sort of
like seeing
the effect of
of you know
clean my own life
and of course
I worked with
some incredible
coaches as a
athlete myself
right was is
really meaningful
I think and
I think that
you know the last
two coaches
I've had are
have Asian American
heritage in them
as well and
one of the things
you see in the um
current landscape
of coaches is
that there are
a lot of white men
which you know
there are a lot
of you know
fields were true
older white
men and and
there are other
other groups
but I've heard
people say that right
and I work with
clients today
who have said
things like
you know what I
I feel seen
by you in a
way that I haven't
from other people that I
worked with
um I found about
ADHD you know
I started working with
a client recently
who's kind of
like a friend
you know and I
was reaching
out to her saying
like hey do
you know anyone
who you think
might be a good fit
for me and she's
like I don't
know anyone
but I could
be you know
and I didn't
really know that
you were so
Asian is something
that you can
see on my face
right you can
see my name
like that's
my background
um ADHD is not
something that's
obvious that's
out there right
some people
don't even necessarily
know and so
many kind of
like exhibit
many of the
I'm not you know
qualified to
diagnose but
so many exhibit
a lot of those
qualities um
and it can be
very isolating
to feel like
well my brain
works differently than
other people are
like you you
like that you
you can't do
that or why
can't I do that
that seems easy
for you I mean
I can do other
things that are
easy for me
that are hard
for you but
it's always
frustrating
when people
expect that
you should be able to
do this thing
so I think those
are two areas
that are very
natural for
me to kind of
engage with the
the client on
uh the the other
one is really
this idea of
courage and
conviction right
we've talked
a lot about
swinging big
we've talked
a lot about um
going for it
and you know
my message is
often like face
planning hurts
less than you think
and believe me
I face planted a lot as
as an athlete
professional
you know I've been
laid off right
I've been sued
you know right
my companies
are shut down
right I've I've
been you know
I found my face
I've been hit in
the face and
it is painful
there's no question
but this you know
we talked about struggle
struggle is so
important for
education right
you you you
can't like the
when you take a
test and you
the testing
effect is that
when you take a test
and you have to
think about
the answers
and like fill
in the answer
you learn many
times better
than when you
like review
the notes when
you like look
through the
the recap and
you're oh yeah
I know that um
versus sitting
down for five
minutes and
answer like
10 questions
and you're like
oh was it NH3
or is it NH4
you know like
that's your
brain actually
working and
same in the
gym you know
it's like it's
those last sets that
really give you
the strength
and it's the
struggle that
you have in
your careers
and the professional
moves that you
make that teach
you you know
when I finally
sat down with
my managers like
okay tell me
how to complete
this document
right and after
struggling with it
and being like
okay you wrote this
but I would
say this do
you know why
I'm like I don't
know because of
this is like
well sort of
you know okay
you know now
I'm learning
so it's it's
like without
struggle you're
actually not
gonna get better
so you kind
of have to do
it though so
that courage
and conviction
is something
that I I I love
bringing to
to my work as a coach
can I share
something that
just happened
the other day
yesterday I
was posting an
episode it's
10:00 cause
I'm doing it
too late and
part of me was
like why am
I doing this
you know that
moment of like
everything is
going well and
you have this
conviction then
there's days
when you're
tired where
things are not
going quite like
you want to be
and just why
even bothering
to do this and it is
really hard
especially when
you're working
really hard
to do something right
but you have
those moments
and I had this morning
reflection on
it because it
was disturbing
to me and I
realized the
reason I had
that feeling
wasn't because
I really think
that that's
the best reason
is to pivot for myself
it's because
I have this fear
financial fear
um you know
being not good
enough but mostly
financial fear
right that if
this isn't paying out
there certain
responsibilities
I have and that's
okay you know
it took me to
action like
yes I can have
those fears
and I can still
act I can have
those fears
and those are
okay but I can
still choose
to not act just
based on fear
I can still
choose to see that this
this journey
that cons the
benefits I'm having
but learning
about myself
about feeling more alive
having this
opportunity
to discover my own
limits having
opportunity
network of you and me
incredibly like
that is worth it
to me and yes
there's like
risks but we
have to be very
mindful about
what we're stopping
ourselves from
by just focusing on
the negatives
of the costs
and the fears
and driving
our decisions
that way so
I just wanna
be transparent
that I had the mode
this morning
where I was
really feeling like
this it shook
me a little
bit because
I haven't had that
serious doubt
but I think it
was because
I've been recently
really focused
on energy and
focusing my
energy on like
the positives
on intentional
conviction and
in some of those
like for that
like are you
sure are you
sure Anya they
can show up
that way so
Chris have you
had moments
of self doubt
and how have
you dealt with
them if you
don't mind me
asking yes Anya
first of all
I I wanna say
you doing amazing
with this podcast
it is you you
kind of kind of
nowhere with this
right and it
you're running
in a really
professional
way and I can
say that with
genuine experience
because I hired
a firm to put
me on like 12
different podcasts
I have been
on a bunch of
podcasts lately
different hosts
different processes
you know and
you're running it
at as good as
any of these
like posts with
like hundreds
of episodes
have been doing
it for many
years seriously
even better
in a lot of
ways of the
the the the
sort of how
you cut it all up
and put it together
thank you and
so I think you got
a lot in a short
amount of time
and the self
doubt is normal
it's natural
it's gonna happen and it's
it's a 2 coin
because when
you experience
those moments
of doubt and fear
and struggle
um when you
make it you
feel that much
better about it
right what's
so good about
winning something
that you didn't
have to try
that hard at
it's not even
that cool right
it's like the
participation
award nobody
cares about
the participation
award it doesn't
really help
boost anybody's
self esteem
cause they they know
that about it
you didn't have
to do anything
you could have
done nothing
and you still
get it right
and not to say
that we should
only celebrate
winning and
being the No.
1 or whatever
but like uh
the the personal
achievements that
you will value
the most are
the ones that you
had to fight
the hardest for
and maybe have
the most doubt
about I have
of course my
own moments
of self doubt
I you know I
into this uh
this new role
and in when I
was at I don't
wanna switch
to a new team
right and the
first thing
that happened
was that I gone from
sorry you know
several exceeds
expectations
as a you know
in my position
in my title
I didn't get
a promotion
and I was like
you know what
I've been trying
so hard I'm
getting all
these exceeds
like I should
go to a new
place they'll
appreciate me more
and maybe I
can finally
get that promotion
yeah and then I
I like really
struggle right
in the and it
was like a new
as I mentioned
new role new
sort of word
new expectations
new responsibilities
and you know
I I had a lockdown
about like can I
even do this
right and and
like was it
was this a mistake
like did they
let me in and it
was a mistake
like you know
this is that
other org was
like an easy
greater and
now here I am
like really
trying to do
and I can't do it
you know um
and I think
what helped
was just one
when you're
focusing too much
on self doubt
it's often because
you're looking
at outcomes
right you're
looking at other
people's judgment
evaluations
external metrics
you know how
many you like
what's my rating
compared to
all these other people
what's my uh
follower count
or whatever
and what you
should really be
focusing on
is like your
own development
am I learning
things yes uh
am I you know
supporting the
people that
I actually work
directly with
on the things
they need yes
am you know
am I trying
new things you
know and am I
am I do ways
that I hadn't
been exposed
to the fact
that it is hard
is telling you that your
brain is gonna
learn something
from this if
you don't like
try to like
block everything
out right so
so I think that's
that's how you
can work through
self doubt and
and you know what
back pocket
back pocket
screenshot all those
nice things
people say about you
other than that
you're proud
you know your
peer reviews
or like if people
write your reviews
your podcast
or like send
you emails or
you know even pays
you a compliment on
the street you know
write that down
put that in
a folder and
when you're
feeling down
about yourself
go back and
and and look at
you you you're
allowed to you're
allowed to to
kinda swim it
out a little bit
you know Scrooge
Mcduck style
but in your
in your confidence
right um it's
there's no shame
it's absolutely
part of the
game of keeping
your psychology
on the level
when you're
like too low
you gotta pull
yourself up
that's billion
because our
brains are wired
to think to
focus on the
negative so
whatever heck
you gotta do
to be positive
that's all fair game
I love it and
isn't we've
covered so many
incredible things
I think we talked
for seven more
hours which
you should come
back and we
don't do that
but is there anything
you want us
to focus on
before we wrap up
any subject
that is on your
heart that we
can zone in on
yeah you know
I think it comes
back to this
feels like such
goofy thing to
say but I'll
say it because
um you know
that's that's
kind of like my
part of my journey
is just like
connecting with
your body right
I'm not saying
everybody has to
go and be an
athlete and
try to win roll
records and
all these things
I'm a little
crazy and that's
what I like
to do for fun
okay um but
I think that every
person everybody
um needs and
can appreciate
their body more
right stretching
mobility right
I think stretching
is actually
a big thing
that my wife
and I have like
sort of recognize
I'm sort of
flexible which is
obviously helps
as a gymnast um
but for her
she gets stiff
right she just
like doesn't
feel good in
her body and like
we've often
throughout this
nighttime routine
of like doing
some stretching
before doing
the pad and that
that mobility
that was kind
of coming up
now more right
mobility is
is so important
for your quality
of life and
when your body
feels better
your brain works
better when
your cardio is better
you can work
harder and longer
right it's it's
literally means that
your body is
more efficient
at bringing
oxygen into
your brain right
take it from
the biology major
that I never
otherwise use
right like this is
the biology
you know yeah
you're putting
you gotta put
oxygen in your
brain and an
exercise develops
you know I'll
say this one
other thing
it's it's it
worked better
because it develops
you know uh
this develops
your brain but
it also makes
you happier
you've all heard
of endorphins
but do you know
do you know Anya
what endorphins stands for
endorphins right
it's kind of
like a what
is this word
it's a it's a
or whatever
it's like a smash
together word
it stands for
endogenous morphine
you know like
morphine like
the thing they
give you when
you're like
you know after
surgery right
like even digest
morphine it's
self released drugs
you know it's
it's literally our
free supply
of happy feelings
right in the
healthy sort
of cultivated
version so like
this is this
is the sort
of you know
magic thing
I I I don't
need your new
exercise movement
height person
but like just
if you listen
to this and
you and you
think you know
what you know
like I it's
not a killing
it's literally
like a it's
just gonna make
your life a
better thing
I'm gonna I'm gonna
time and so
that's that's
my my feel do
do you mind
if they dive
into that and
just a little
bit can I add
to that yeah
one thing that
I find really
important and
I come back
come keep is
this trifect of
body mind soul
and I don't
mean soul in
terms of you
know religious
I mean it like
a spiritual
just like having
that reflection
of what matters to you
and I think
it's so true
and important
especially when
you aspire to
do something
difficult in
your life whatever
that is you
need and you
will be relying
on all three
whether you
recognize or not
that foundation
is gonna be
there and if
you're lacking
in one area
again whether
you want prayers
it's gonna affect
how you show up
in other areas
it's gonna affect
how you handle
stress it's
gonna affect
the energy level
you have it's gonna
how you feel
not presentation
Forden conversation
whatever that is
so 100% agree
I think we have
this overwhelming
sense of this
negative body
element where's it
oh it's about
being sexy or
about looking
a certain way
I don't think
that's what
you're talking
about or what
I'm talking
about it's about
having this
feeling of a
liveness in
your body that
your body is
performing optimally
for what everything
you wanna do
but it's hard
right that's
why I'm like
oh well I'm busy
I'm busy all
those things
guys we hear
you Jason on
you but we're
so busy what
I've Learned
that's been
really important
for me recently
is to make small
habits like
those things
that make it
easy to do things
that are best
for you like
I eat I'm really
optimizing how we
very very much
the same thing
but it's just
healthy and
quick right
it's not magic
or a secret
diet it's just
healthy and
quick things
that I can put
into my day
feel good and
doesn't take
that much time
has there been
something similar
that's worked
for you or the
advice you'd
give people on
making it real
so instead of like
oh yes that's
all sounds great
but you guys
make it so easy
but what works
for you you
suggest well
you know I think
walking is a
huge one right
like turning
some of your
um meetings
into walking
meetings is a
is one that love
especially if
it's like a
little bit more
of a casual
call you know
we're obviously
sitting here
on a podcast
before we were
just catching
up as friends
be like hey
you know what
I'm gonna pop
in my air my
AirPods and
for walks that
sound good right
like so easy
for those who
are working
at home I've
definitely seen
people getting
those indoor
treadmills I
I wanna get
one I have one
I have one I
love it yes
if you were casual
you could do a
work treadmill
talk right so
you know that's
a huge one it's
like 300 bucks
a little bit
of investment
but you know
when it's not
doing anything
you can just
stand on it
right you know
you have to
you you you
you stand on it
and then you
walk and it
can really um
get you extra steps
and we were
designed to
move in our
brains were
better when
we move and
you walk slowly
and it's gonna
be a little
awkward at first
but I follow
this Tik Toker
who like has
made her whole
channel about
walking walking
treadmills and it's
like it's like
a skill like
anything else
and you learn
how to do it and
you you know
and don't feel
supernatural
so uh that's my
you know one
one that I have
and one that
I wanna get to
yo I love it
isn't well is
this has been
incredible I so
appreciate this
conversation
I honestly am
inspired by
everything you
have done about
everything that
you're doing
and I know that
with your passion
for coaching
people who work
if you're gonna
change their life
but also I'm so
grateful that
you're working
on this book
to help bring
inspiration to
your broader
level thank you
for hitting on
all the points
about pivoting
about being
real about how
to go through
this journey
through ADHD
and other challenges
maybe other
people will
find themselves in
so they can
have a sense
that you know
whatever they're
going through
they can get
through it they
can go through
the doubt and
through the
challenges and
still come out
stronger than
because that's
a worthwhile
pursuit and
before we wrap
up we have uh
three rapid
fire questions
so whenever
you're ready
let me know okay
uh first uh
off which opport
excuse me which
entrepreneur do
you admire the most
Woo Seth Godin
Seth Godin has
written a number
best selling
marketing books
but he's also
started several um
technology companies
and runs in
the marketing
workshop in
the alt NBA
so he is truly a
mensch a gift to
the world and I
I respect him
such absolutely um
best advice
you ever received oh
you know uh
give it your
absolute best
and you'll never be uh
disappointed
with where things go
of it last but
not least in
the positive
context going
off track is
chance to discover some
new possibility
beautiful beautiful
concise confident
limitation great
to all of our
guests I hope
that you found
something that
resonates with
you there's
so many things
to unpack and
so many great
insights to
get so thank
you so much
for investing
in yourself
one last thing
I wanna mention
as we wrap up
is that we are
a podcast with
purpose and
I'm so grateful
to be supporting
the amazing
nonprofit ready to
empower which has
been around
for 10 years
and they are
empowering women
worldwide they
are raising $50,000
right now by
December 8th
100% of those
go to operation cost
so if you're
feeling inspired
to make a difference
in the world
I would so appreciate
any amount that
feels right
for you check out
the description
below and again
Jason thank
you so much
anything you
wanna share
with our audience
before we wrap up
thank you so much
Rania for for um
making the test
you know we
we we had um
challenges and
we had some
recording challenges
but we we made it
work we were
resilient we
were flexible
we were adaptable
this is all
just a microcosm of
the whole thing
thanks so much
again yeah it
was a test in
resilience in
practice and
again thank
you so much
to all of you
coming right
off track of us
we look forward to
having your next
adventure of us
until next time
take care bye
Jason see ya