Do You Really Want to Be The Boss?

“Millions long for immortality who don’t know what to do with themselves on a rainy Sunday afternoon.”

-Susan Ertz

It’s a great life goal. You want to be your own boss. The benefits are obvious and awesome. Work whenever or wherever you want. Do whatever you want. You answer to no one. I sort of ran out of benefits actually.

It’s truly wonderful to have my rewards be as directly tied to my efforts as possible. I thrive in that environment, but this lifestyle isn’t for everyone. Here are some of the less obvious reasons why.

Stress — I don’t mean that being a leader is difficult. I mean it’s your job to worry. When business isn’t as smooth as it could be, it’s your job to right the ship. When business is booming, it’s your job to keep it that way. When business is stable, it’s your job to think of how it can come apart and stay months ahead of those obstacles. When worst case scenario HAS to be on your mind somewhere to be effective, stress is inevitable. Also, you have to keep your hand steady for the sake of the team. No one wants to hear about how fragile the brand can become in 3 bad moves. The stress of that responsibility isn’t for everyone.

You sound like a tool — No matter how much you tell yourself you are genuine and hate buzzwords, you can be the first person to accidentally take a conversation into industry lingo hell. I frequently add post-scripts to my status meetings.

Sorry I got so deep into redefining our estimates and pipeline. This meeting was supposed to be me saying “Good Work.”

On top of that, you must be the the biggest dreamer for the company. In a conversation that stuck with me alongside Diamond Kinetics CEO, CJ Handron: “If I didn’t think we were going to take over the world, I wouldn’t be a very effective CEO.” That’s exactly right. If you’re not the one reaching as far as possible for success, no one else will. You simply won’t get there if you haven’t mapped out the route ahead of time. “I just hope I get lucky” isn’t very impressive on a pitch deck. Most of the time though, delusions of grandeur are best kept to yourself in order to save face.

Responsibility — My number one concern at SewnR is taking care of the family. That means employees’ mortgages, dogs, and vacations depend on me. That means foregoing my salary for the first few months strengthens the company’s infrastructure to benefit everyone. That means working two job titles late into the night and waking up early mornings until the exact moment both positions suffer. That is more prudent than expanding the team immediately.

When most people wake up and see what they’re doing today, I’m looking 3 months ahead to make sure Joe will still be busy. There is a deep purpose to be found inside of responsibility, but sometimes…it just sucks.

Delegating — It sounds easy to do, but most people struggle with it. When you delegate work, it’s not going to be done the way you want. The job will be done the way that person wants it. You also must think ahead and be as specific as possible. Effective delegation comes from doing the entire job in your head before you hand it over. Nothing kills a project faster than ambiguity. Personally, I love delegating. Everyone on the team is more talented than I am (Recruiting and team building is a much much bigger conversation for later). Planning, instructing, and then handing-off usually results in a product far better than I could have anticipated or done myself.


It’s extremely boring to say steering the ship at a startup is difficult, but it’s interesting to see how rewarding and challenging it is in a thousand ways I never anticipated. No one is here to tell the team what to do. No one makes a ruling on whether the plan is correct. In fact, just about nothing is correct or incorrect anymore. Instead, it’s replaced with a spectrum of valuable versus wasteful. All I can do is be prepared, transparent, and depend on the team as much as they depend on me.

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