How I Created Four Years of Unnecessary Suffering Building My First Startup
Christmas 2008. Weeks after Lehman Brothers collapsed during the financial crisis.
I broke down crying at my wife's (then girlfriend) family's house in Florida.
Almost four years of 16-hour days, seven days a week. Almost four years of feeling like a zombie, unable to think clearly, constantly exhausted. Almost four years of grinding myself into a shell of my former self.
"I don't know what to do," I said. "I feel totally trapped."
And I was trapped, but not by what I thought.
The trap wasn't the startup. It wasn't the 16-hour days. It wasn't even the financial crisis that had just slashed our acquisition price.
All that grinding to control the outcome. But it was something else that was controlling me the whole time.
The Bet I Made About Myself
When I started Wellsphere in 2005, I'd just graduated from Stanford Business School with massive loans. I went from making decent money in finance to two years of no income while spending hundreds of thousands on school.
I told everyone in my world I was starting a company.
And somewhere in that process, I tied the outcome to something much deeper: If this fails, it would reveal and confirm the belief of my unworthiness.
Not "the startup failed." I would be exposed as a failure.
I felt more pressure to not fail than I did to succeed. It wasn't "I want to win." It was "I can't fail, that would be catastrophic."
Now failure wouldn't just be disappointing. It would be public proof I wasn't enough. I couldn't quit. I couldn't leave. Even when I was fried and miserable, I was trapped by my own making.
So I worked. And worked. And worked.
My logic was simple: At least if I work as much as humanly possible, I'll know I did everything I could. If it fails, I can't blame myself for not trying hard enough.
I was trying to outrun a feeling (unworthiness, shame, self-blame) through sheer effort.
When External Circumstances Make the Decision Anyway
For the first couple years, we built something that didn't work. We pivoted. Eventually, we found traction and grew to six million monthly visitors pretty quickly.
In August 2008, we started negotiating to sell the company. Things were looking good.
Then Lehman Brothers collapsed.
The 2008 financial crisis was in full swing, and suddenly it was really hard to raise money. The acquisition went through, but the price declined from what it would have been if the world hadn't fallen apart while we were negotiating.
That was kind of heartbreaking. We'd finally built something of value, but external circumstances limited our options.
After four years of grinding, it wasn't much of a huge outcome.
All that suffering. All that effort to control the outcome and the macro environment, completely outside my control, decided what the outcome would be anyway.
What I Know Now That I Wish I Knew Then
Years later, after hiring a coach and going through the Landmark Forum, I realized the story I had about being unworthy and I finally saw what I couldn't see then.
I wasn't operating effectively. I was operating performatively. I couldn't think clearly. I had no mental spaciousness to step back and see the bigger picture.
The exhaustion wasn't preventing failure. It was preventing the clarity I needed to succeed.
And here's the irony: The startup world is probably the most gracious industry about failure.
I've seen it now many times with clients who've failed. They land on their feet. Generally, you can get a pretty good job. You can raise money again. No one judges you harshly. They appreciate that you went for it.
The amorphous boogeyman my mind created wasn't real.
But the trap I created by tying my worth to outcomes? That was very real. And it created very real suffering, suffering that had nothing to do with the actual situation and everything to do with the meaning I'd assigned it.
Year-End Reflection
It's December 21st, just a few days before Christmas.
That Christmas breakdown seventeen years ago was the beginning of understanding something:
I'd created my own suffering by making the outcome mean something about my worth. And when you do that, you trap yourself.
You can't quit, you can’t allow yourself to rest, and you can’t trust life to carry you through its inevitable change. You're stuck trying to control something that the world will likely influence regardless.
The only way out is to see the trap you've created, to recognize where you've tied your worth to outcomes and consciously choose to let that go.
As you're reflecting on this past year, I invite you to ask yourself:
- What have I been trying to prove about myself this year?
- What outcomes this year (preferred or not) did I make mean something about my worth?
If you'd like support with deeper reflection, here are my 3 favorite (free) guided workbooks:
- Conscious Leadership - A Year of Conscious Reflection
- Year Compass
- Steve Schlafman's Annual Reflection Guide
I'd recommend choosing one. If you're unsure, do the Conscious Leadership one.
Please feel free to share your reflections with me. I'd love to hear about your vision for the year ahead and support you in any way I can.
Merry Christmas,
