Transitioning from Founder to Employee

A friend is looking to sell their company and asked me, “How difficult was it to transition from Founder/CEO to employee?”

Here’s my response:

It depends on what you want or see for yourself. If it’s “I’m tired, I could use a break”, then it can be 80% great.

If you’re in the “I’m still hungry and ready to keep pushing” camp, then not great.

But even in the first example, there are times when I feel, “I don’t like this or that decision.” Which is why I say 80%. But that’s the trade-off when taking a backseat.

You aren’t the main point person anymore, and you can be more in the weeds. But you also don’t get the final call or make the decision you think is best.

Personally, I was more on the tired front.

I do disagree with management decisions at times, but:

a. I was the one who sold and stepped back. It was my choice and I must remind myself that, and…

b. I have to remember how stressful it really was actively running the business. As an optimist, as most of us are, you only think of the good times. But in reality, was it really good? It was fun building, but also a lot too. Rehiring, churn, a bad customer review, toxic employee, etc. I try to have that full-body perspective.

The other thing I realize is we’re all still young.

There’s plenty of time if I want to dive back into a founder role again.

I could also do it differently, maybe fewer people and not 100% focused on growth. What if I optimized for cash flow and work/life balance? Cool, I can dabble there in a few years too.

I’m still figuring it out, but when I zoom out to a 5-year window instead of 2wk, it all gets a lot less anxious and stressful.