Growing as an Entrepreneur
Every so often I sit down with a fellow entrepreneur – somebody a bit ahead or behind me in their business journey. I don’t mean financially ahead or behind. Where someone is in their business journey and how much money their business makes are correlated, but not the same. Instead, I mean something less easy to quantify: the emotional journey of being an entrepreneur and the challenges that come as a result of building something new in the world.
In 2021, Zander Media grew from two full-time employees to ten. Then, in 2023, our client base contracted and we had to contract, too. We had some disgruntled employees, difficult partings, the threat of a lawsuit. I had months of agonizing heartache.
A CHRO friend saw me in tears one day. When I explained what was going on, she said, "I'm sorry to hear it. This is your first time getting threatened with a lawsuit? Poor baby. We all remember our first time."
She wasn’t putting me down or lessening the significance of my struggle. She had just been through similar challenges – hypergrowth, layoffs, disgruntled employees, and lawsuits – many, many times. Having been through it, she knew something I didn't: that everything was going to be okay.
I just returned from five days filming and managing a 12-person film crew at the Transform conference in Las Vegas. Before that, we had a whirlwind 24-hour turnaround filming for Suzy Welch in New York City. Earlier in March, I produced the first Snafu Conference and I got married. (Obviously, the last of those is by far the most important.)
I could not have done what I've done in the month of March without all of the business learnings that came before.
I don't have an exact guide for how to get progressively better at difficult things. (Though if you haven’t read it, my new book This Might Work is a good place to start.) But here are some of the things that I advise my friends when they're just getting started on their own entrepreneurial endeavors.
Derive Meaning Outside of Work
The 4-Hour Workweek was an important book for me when I was just getting started as an entrepreneur. Reading someone else describing a different approach to work – something I’d been doing from an early age – encouraged me to explore an atypical path.
But the chapter that I now believe to be the most underrated in Tim’s book is about building life outside of work. He calls it “Filling The Void.” If one of the goals of entrepreneurial success is to define life and work on your own terms, you have to decide how you’re going to spend your time, as well.
Financial Success For The Sake of Financial Success Feels Hollow
I'll never forget the first time I received a check for $100,000. It was a couple of years into Zander Media, and it was the largest check I’d ever seen. I was thrilled for the ambition of the project we were undertaking – and surprised to find that the money felt hollow.
After the initial elation of getting paid, financial success for the sake of financial success feels hollow. Money matters, obviously. But a rich life is about more than making money.
Exercise More Than You Think
I’ve been training movement almost every day for thirty years. When I’m asked about exercise, my advice is always the same: move every day and more than you think.
It’s true in general, but especially so in the life of an entrepreneur.
So much of our work is interacting with employees or clients, asking for things, stretching emotionally. Building a physical habit will help you stay grounded.
Take Breaks Your Way
My friend, psychotherapist and author Emily Anhult once wrote “Don’t cope the same way you celebrate.” Over time, I’ve come to disagree with her.
When I’m stressed out and overwhelmed, I go for a long run or lift heavy weights. To celebrate a really intense period of work, I do the same.
I think Emily was referring to more unhealthy or addictive practices like alcohol or binge-watching Netflix. If so, then perhaps I agree. But ultimately my advice is: take breaks your way.
Have People You Confide In
I have close friends who’ve shared every step along the way, and also people peripheral in my life, like the CHRO who offered comfort in that moment.
Every so often, a fellow entrepreneur will ask me for advice while offering a ton of caveats: “if you have time,” “if you don’t mind,” and more.
We all need people to talk to. I’ve had people supporting me. We can all pay that support forward.
Talk to people – both those who've been through it, and those who will go through it in the future. You’ll be a better, more empathetic person for having done so.
Take Yourself Less Seriously
I'm more guilty than most of taking my own stress more seriously than is necessary. If we don't even remember Alexander the Great's full name, why do I believe that my work is going to be any different?
It's not to say that it doesn't matter, or to treat it as less of a big deal. When I'm believing that everything rides on this moment, it's sometimes helpful for me to pause and remember that I am not all that significant, after all.
Mistakes Are Recoverable
When I first started writing Snafu, I felt agonized every time somebody pointed out a typo – which was often. In the early stages of entrepreneurship, it feels like every misstep has the potential to be catastrophic.
Almost all mistakes are recoverable. The only ones that aren't are the ones that result in death or maiming.
Never Stop Learning
One of the reasons I love entrepreneurship is that it requires ceaseless learning. Even though Zander Media hasn’t hit the high mark in terms of absolute gross income that we reached in 2021-2022, the company has been more profitable since, and we’ve undertaken more creative, ambitious projects.
What I’ve just successfully accomplished during the month of March (did I mention that I also got married?!) would have been impossible for me even a few years ago. That the Zander Media team executed the work with aplomb makes those successes even better.
Of course, I want to win. But the joy of learning for the sake of learning is as important along the way.
3 Things I’ve Loved This Week
Quote I Think About Often:
“Sometime in my 20s, my mom told me ‘You’re too old to blame your parents for anything you don’t like about yourself,’ and I think that’s the most important thing she’s ever said to me.”
This from entrepreneur Tara Viswanathan, who spoke on stage at Responsive Conference 2024.
Video I’m Loving:
I prefer ravens over crows, but this is wild. The Twitter account “Nature is Amazing” is a bright spot on the Internet.
Tool I’m Using:
I’ve been flying a lot lately and wanted something better than my in-ear Airpods to block out the sound of the airplane engine.
After a bit of searching, I discovered these Walker’s Razor Electronic Muffs. They’re designed for gun ranges, but work incredibly well for flights (or when operating my weedwacker at home).
Added bonus, my ears pop less and hurt less when I use them on takeoff and landing.
Want more?
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Responsive Conference is coming back in September! With AI and a changing economy, our jobs and careers are changing faster than most of us can adapt. Attend Responsive Conference and learn how to keep up with change.
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Until next week,
Robin
