Past Midway Ramblings on Business & Life

Being the Boss & Making Mistakes

Nothing prepares you for entrepreneurship like being an entrepreneur.

As the leader of your company, you are tasked with articulating the mission, setting the overall strategic direction, ensuring successful execution and establishing & shaping the corporate culture. Simple right? But few of us are excellent at leading a company, especially our first company.

As leaders and managers, we fail, sometimes epically. Worse yet, we see ourselves failing in real-time, acutely aware that we may not know how to right the ship.

Being Real (& Clueless)

Earlier this year, I was on the phone with Kendra, our Vice President of Operations. We had just finished a long conversation about strategic initiatives. Before we hung up, as an impromptu aside, we discussed why the conversation hadn’t gone so well. We just weren’t very effective on the call together, which is really unusual. I suppose it took us by surprise, so we just talked about it.

At the end of the call, I said something to the effect that she was asking me strategic questions about marketing for which I had no answer. It wasn’t my strong suit. Consequently, I simply did not know the next steps forward. Thinking out loud, I remember saying,

“It’s strange. Even though this is my company, I’m not sure what we should do next in this area. It seems like the founder should have some answers and maybe know how to do stuff.”

But we often don’t. At least I don’t.


For most leaders who have established a record of relative success in life – starting with academic success in school and perhaps early career success as an employee – it’s difficult to cope with the realization that we consistently make mistakes and frequently have very little clue what we are doing as an entrepreneur. It’s an environment ripe for imposter syndrome.1

As founders and company owners, we need to accept that uncertainty and ambiguity are part of the job description. But it also helps to know most of our fellow entrepreneurs feel like they are flying by the seat of their pants a lot of the time as well.

The best we can hope for is to get lucky with our decisions at least some of the time, to learn from our mistakes at other times, to backfill our ignorance with brilliant teammates where possible and to work with patient people who can tolerate our shortcomings as leaders.

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  1. “Imposter syndrome” describes the feeling that we do not deserve credit for our accomplishments, that our successes are somehow the result of luck rather than competency because deep down, we are fairly certain we have no idea what we are doing. Even though others might perceive us as capable, it seems like someone more capable should probably be in charge.


By Andy Jones
Past Midway Ramblings on Business & Life

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