You Can Always Do More as a
Business Owner, but Should You?
The
best leaders understand that they have to deliver both consistency and
intensity in varying degrees on a regular basis.
EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V
AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1
Sep 30, 2025
Recently, I was asked if
I was interested in writing about a world-traveling CEO who prided himself on
basically never being in the office but still had a successful, growing
business. His representative suggested that he’d be happy to share the secrets to
his “success” with me and also explain what a wonderful time he was having
flying all around the globe to exotic and exciting places. To be clear, this
was demonstrably not business travel.
I passed on the pitch,
although the topic of in-office work isn’t one that’s likely to disappear any
time soon. Amazon’s having a tough time forcing its workers back to the
office. The new CEO of Starbucks is getting loads of grief from his
own employees about his plan to “commute” to the office by company-owned jet
from Newport Beach to Seattle. Work from home has always been a sub-rosa class
issue since the pandemic began: essential, blue-collar, and no-collar workers
never got a break during COVID, while many white collar workers worked from home and barely felt a thing.
But one issue about the
proposal stuck in my mind. Without knowing the particulars of his situation or
seeing his company’s actual financial records, I found myself asking this
simple question: if his operations were really doing well—essentially in his absence—how
much better could the business be doing if he was actually present and
available to his team, paying attention every day to the nuts and bolts of the
business, and concentrating on improving his margins and identifying new
markets and opportunities instead of running up his frequent flyer
miles? And frankly, what kind of lazy board and indifferent investors
would tolerate this kind of selfish and lazy behavior. I’d say, “less showboat
and more tugboat.”
It felt to me like this
guy was perfectly happy to settle for good enough, which I don’t think any real
entrepreneur ever does. Anyone who has ever worked with me knows two things:
(1) I’d never ask more of them than I ask and expect of myself; and (2) I
believe that there’s always more in each of us than we even know (until we
try). Once you see and realize that potential and prospect, then you’ll never
be happy or willing to settle for less. It’s not about acceptance, it’s about
expectations: people learning, growing and becoming. If I accept you as you
are, I make you worse. If I treat you as though you are what you are capable of
becoming, I help you reach that goal.
I’ve called this
approach obsessive iteration or the process of successive approximation—always
getting a little bit better every day toward the unreachable and delusional
goal of perfection. There’s really no quit in a true entrepreneur because
there’s always another mountain to climb and there’s a constant internal drive
which keeps pushing you forward, demanding what’s seems impossible, and
sometimes even achieving it. You never sit still or stop. There’s no finish
line and rarely any appropriate time to celebrate. More isn’t necessarily
better, only better is better. But there’s always a lot more to do to be even
better. Or, as we used to say, too much is not enough.
I have a reputation for
relentlessness and I’m proud of it, although I do concede that it’s not for
everyone. It’s critical for new business builders to understand that not
everyone shares your craziness or is quite as zealous and committed as you are.
If you aren’t careful and learn to occasionally rein in your own drive and
enthusiasm and spend some time making sure that there’s room for other people,
attitudes and approaches, you’ll never build the kind of team or business you
want. It’s a balancing act and it’s easy to intimidate or even scare off the
exact kind of talented people you’re going to need to succeed if you’re not
careful. Pushing your people too hard is a sure way to push them away. The best
leaders understand that they have to deliver both consistency and intensity in
varying degrees on a regular basis. This helps the team understand what to
expect and appreciate what you expect. It’s not an easy task, but it’s
essential.
And to be clear, there’s
also another vitally interested and important party to these considerations,
and that’s your family. Your family will ultimately be a much more
important extension of yourself than any work you do, although it often takes
quite a while for young entrepreneurs to realize that. There’s always more
work, but you only have one family. They share every bit as much as you do in
the ups-and-downs of the business building and the
sacrifices as well. Even more to the point, your inbox will always be there
waiting for you, but your family might not be, so put them first. Family is
more important than fame or fortune. Don’t try to tell yourself
otherwise.
It’s easy to think that
you’re constantly working like a maniac for your family, but if you ask them,
it’s very unlikely to be their view. They’d much rather have more of
you. And please don’t make the stupid mistake of ever telling your spouse
or your kids that you’re working for the money so you can afford to give them nice things,
live in a lovely home, and take great vacations. This is the worst message in
the world. It’s not about making money or a living—it’s about making a life
you’re proud of and making something that makes a difference. If you don’t know
why you’re working and doing what you’re doing, then maybe it’s time for a
change.
So, the next time you
find yourself wondering whether it’s time to call it a day or whether you
should maybe put in a few more hours at the office (and likely miss dinner or
an important event with the family), ask yourself: I know I could do more, but
should I?
