What’s Your
End Game?
Ambition is a powerful and valuable thing.
But you have to know how to use it.
WHY DO WE KEEP GOING?
It sounds like a dumb ques-
tion. Entrepreneurs are pro-
grammed for movement—to
grow more, to achieve more, to
be more. But it’s worth stepping
back to ask: Why?
I got to thinking about this
recently, after a conversation
with Katie Sturino. She’s a
body-positivity activist who
launched a personal care brand
called Megababe in 2017, and
the past few years have been
transformative. “If you would
have told me 10 years ago what
I’m making now, I would have
been like, Whaaaaat!” she said.
“But every year the stakes get
raised. I’ve been trying to figure
out, not a financial point, but
what life looks like to feel
comfortable—because I don’t
think there’s ever a number.”
We were talking during a
taping of Hush Money, a pod-
cast I cohost, and her question
resonated with me. I have also
achieved a lot of my initial goals,
and have also discovered that
there’s no bell to ring or finish line
to cross. There’s no moment of
pure comfort where I kick back
and think I’ve made it. Instead,
as I grow my career, I just start
comparing myself to even-more-
accomplished people—ones who
have a larger platform, a higher
income, and a greater impact
on the world. The more we
achieve, the more we want.
“How do you shield yourself
from that?” Katie asked me.
I didn’t have an answer,
but I thought back to the first
12 / E N T R E P R E N E U R . C O M / April-May 2020
time I realized ambition’s end-
lessness. It was 2008, and I
was living with a girlfriend in
Boston. We’d already moved a
few times for jobs of mine as
I pursued my goal of working
in national magazines. Then I
got the offer: A big magazine in
New York wanted me. But the
girlfriend was done moving.
“When does it end?” she asked
me. I repeated that question to
my parents as I wrestled with
whether to pick the job or the
relationship, and my parents
gave me excellent advice: “It
never ends,” they said. If I
stopped now, I’d just feel stuck.
They were right; I took the job.
So that’s what I said to Katie.
If you’re the kind of person ful-
filled by growth, then take joy in
the endlessness of it. sure it’s done right? itself. We want to be actively
But after we wrapped up and Here’s what I’ve come to doing the thing we love, and
left the studio, Katie’s question think: We each need a goal actively fulfilling our vision of
kept nagging me. She hadn’t that’s not about outcome. ourselves. We are in a state of
just asked about whether it We can’t say, “I’m doing this being. That doesn’t stop.
ends; she asked about getting to get rich,” because you can So what drives me? Having a
lost in the endlessness. That’s always get richer. We can’t say, strong voice, and a message to
a reasonable thing to worry “I’m doing this to be famous,” share. I go into that more in my
about. Our pursuit of bigger because you can always be more profile of Dwayne Johnson and
things can take us away from famous. That’s a recipe for dis- Dany Garcia in this issue. And,
those we love. Other times, it appointment. So when we con- hopefully, I also accomplished it
can be an unhealthy distraction. stantly pursue bigger things, we in this column here. But it’s done
Tim Ferriss wrote about that cannot actually be on a quest now. Time to write another.
recently, admitting that his for bigger things.
initial quest to become famous We must instead know, deep
was driven by deeper personal down, what drives us. Is it to
problems. “I desperately hoped make an impact in a commu-
that love from without (i.e., nity? To solve problems? To
from masses of other people) innovate? We can do those
would somehow make up for things endlessly—and if we do Jason Feifer
hate from within,” he wrote. them well, our opportunities jfeifer@entrepreneur.com
So if we’re going down an will only grow bigger. The pro- @heyfeifer
endless road, how do we make cess, therefore, is the prize by S U B S C R I B E : entm.ag/subscribe
Photograph / N I G E L P A R R Y