The Myth of the Fearless Entrepreneur
We tend to overplay the boldness of people who start businesses.
But understand that fear is going along for the ride, and you need to have a
plan for it.
BY HOWARD
TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH
INVESTORS@TULLMAN
Everyone will tell you that entrepreneurs are fearless risk
takers. They’re heroic characters and great adventurers who willingly face
tremendous barriers and work tirelessly to overcome the imposing obstacles to
success.
Everyone, that is, except the entrepreneurs themselves who, if
they’re honest with themselves and you, will tell you a much different story.
Michael Jordan, as arrogant and self-assured an athlete as they come, once
said: “I’m not really sure whether anyone, if he’s telling the truth to himself
in the middle of the night, is a hero to himself. You’re not a hero when you
look at yourself. You just try to do the best you can.” Heroes and cowards feel
the same fears-- heroes just react differently to it.
The best entrepreneurs are those whose faith in themselves and
the future is stronger than their fears. And the first step in managing your
fears and concerns-- to keep them from keeping you from getting ahead-- is to
recognize and acknowledge them and then to address them. Action conquers fear.
Fear always flows largely from ignorance-- if you can identify, illuminate, and
examine the causes, you can deal directly and successfully with them. It’s
always better to suck it up and face your fears than to just suffer on and keep
living with them.
And to be clear, there are some folks who are simply beyond
salvation. They’re overly ambitious and ignorant or they’re so deluded that
they don’t really appreciate how the odds are stacked against them. Or how
unrealistic their dreams and expectations may be. They have nothing of value to
teach you other than what not to do. Of course, these are the people who will
crash and burn repeatedly because they never learn. As the Foo Fighters said, in My Hero: “the best
of them bleed it out, while the rest of them peter out.”
Sadly, but not surprisingly, as in the case of the WeWork
founder, some of the most prominent venture capitalists reinvest with these
dreamers and schemers and continue to promote certain delusions and their
promulgators. These guys have memories shorter than even the MAGA morons
and their greed clearly overcomes any good sense that
they may have once had.
I’m not trying to be clinical here, only practical. I understand
that doubt, anxiety and even depression are an inevitable part of the process
and that everyone is going to have plenty of ups and downs regardless of how
rosy the path looks from the outside. Just ask Bruce Springsteen about that
sometime. And I also appreciate that we all face the standard set of objective
worries and concerns, including aggressive competitors, ridiculous regulators,
constant changes in emerging technologies, and talent shortages. But the real
key to moving upward is to look carefully inward. You don’t conquer a
mountain-- it’s always there. You conquer yourself and your fears on the way to
the summit.
Overcoming your fears is all about asking yourself honestly what
it is that you’re actually afraid of. What’s holding you back from moving ever
more boldly forward? This list is theoretically infinite and unique for each of
us, but when I talk to serious and successful serial entrepreneurs, there are
always a few clear greatest hits that are on everyone’s list. If these look quite
familiar, I hope that doesn’t come as much of a surprise. Seeing them clearly
is the first step to dealing with them, and hopefully figuring out how to get
around them and put them behind you.
Caring Too Much About What Others Think
In our hyper-observant, obsessive, and critical world, where
everyone’s an opinionated expert on everything and they come equipped with
massive social media megaphones, it’s easy to lose your bearings and to care
far too much about what the “world” thinks. Supreme Court Justice Sonia
Sotomayor says: “I don’t measure myself by others’ expectations or let others
define my worth.” Letting yourself, your work, and your impact be measured and
determined by someone else’s opinion is a fool’s game because there’s no way to
ultimately win in a media world that relishes and rewards conflict,
controversy, and criticism. No one’s interested or easily excitable about the
trains that run on time or the accidents that didn’t happen.
Worrying About Disappointing Family and Friends
Half of your friends and family members secretly believe that
it’s admirable but a little nuts (at this time, at your age, in this
environment, etc.) to be chasing your dreams so aggressively. Meanwhile, the
other half will tell you all day long that you can do anything you put your
mind and your energies to. They all think they’re being supportive, but they’re
really just piling the pressure to succeed on your already over-saddled
shoulders. The vocal supporters think they’re helping to encourage you, but the
truth is that no one else can give you the necessary drive or appetite.
Motivation is something you have to find deep within yourself.
There’s no easy answer but, as long as you haven’t borrowed
money from them or asked them to invest, the shortest response is to ignore
both the pats on the back and the slaps to the forehead and just move ahead
understanding-- whether they do or not-- that you know the risk/reward ratio
and that you’re prepared to live with the consequences. The true friends will
be there whatever, and your family has to take you back win or lose.
Feeling You’re Simply Not Up to the Job - Imposter Syndrome
This isn’t a new problem or an uncommon feeling because everyone
(other than narcissists named Trump) feels it at times. A touch of doubt is a
healthy thing and likely to keep your enthusiasm from overwhelming your
experience. Interestingly, most solid entrepreneurs would say that they’re less
concerned about diving headfirst into murky waters than they are about being
reluctant to take those first few steps in a different direction. Every dog is
brave on his own doorstep. It’s when you need to venture out into the deeper
water and lose sight of the shore that your resolve and your confidence are
really tested.
Part of being an entrepreneur is the willingness to run toward
your fears rather than away from them. Turning obstacles into opportunities is
critical and OTJ (on the job) learning how to handle, adapt to, and master
these conversions on the fly, whether you “know” what you’re doing heading into
the mess or not, is what separates the winners from the losers.
Doing the Job for Someone Else
Building a business is tough. It takes preparation,
perspiration, perseverance and, most of all, a true passion to help you stay
the course and weather the storms. It’s not something you do for someone else, for
your peers or parents, or to prove a point. Try as you might, you’ll never be
successful if you’re trying to run someone else’s race or to live someone
else’s life. Make sure you know what you’re doing in your own mind and exactly
why what you’re doing is important and worthwhile for you and for all the
others that you believe your efforts will ultimately benefit. If you’re doing
it only for yourself or only for someone else, forget it.
Going It Alone
Being the boss, even surrounded by the best and brightest team
you can attract, is still a lonely job. Only those who are comfortable with the
responsibility and the solitude that comes with the job are going to succeed,
because that ability and willingness to withdraw, to contemplate, and then
ultimately to decide how to proceed is an entrepreneurial superpower.
I see it in the best of the best. People in the midst of an
active, anxious and attentive crowd who can still separate themselves from the
turmoil and tumult and focus their attention and energies on the problems at
hand. They’re tightly connected and aware, but alone and in their own space at
the same time. This is a learned discipline and if you can’t be comfortable and
alone, you’ll always be lonely and never successful.
The rewards of great leadership go to society at large, but the
price is usually paid by the leader alone. The good news is that it may be
lonely at the top, but at least it’s not crowded.
