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Dealing with Your Demons as a Startup Founder

Alisa Cohn

Alisa Cohn, named “Top Startup Coach in the World” at the Thinkers50/Marshall Goldsmith Global Coaches Awards, has coached startup founders into world-class CEOs for 20 years. Author of From Start-up to Grown-up. She was named the number one Global Guru for Startups in 2021 and has worked with Venmo, Etsy, DraftKings, Mack Weldon, and Tory Burch.

Max, the founder and CEO of an AI data company located in Miami, came into one of our coaching sessions obviously upset. Now, Max is a pretty high-strung guy to begin with, and I had gotten used to his ups and downs, but this was even more pronounced than usual.

He got straight to the point: Sri, his brilliant CTO, had quit, and Marianne, the hot shot Chief Marketing Officer he had been trying to recruit, had declined the offer. All within the last 24 hrs.

This happens in startups – that’s why the classic image of startups is a roller coaster.

But, when the downs of the roller coaster are happening to you, the founder, with all the other relentless pressure on you, it can feel like this is the end of all your dreams and hard work.

Even worse, these difficult moments can leak into your psyche, and you may wonder about your own capabilities, like Max did. In our session that day, he didn’t want to talk about how he was going to replace Sri. He didn’t want to strategize about how he would re-invigorate the search process for the CMO. He couldn’t get over the difficult thought: maybe I’m just not cut out for this. “I have this recurring thought which I can barely admit to myself or to you,” he told me, almost in a whisper. “What if I’m just at the end of my road? I can build this company up to here, but I’m not going to be able to take it from here. And everyone is going to find out.”

Although Max thought he was alone, the truth is that feeling like you’re a fraud and that you’re about to get found out – known commonly as imposter syndrome – is a normal experience of many elite performers and, certainly, entrepreneurs.

Over my two decades of coaching founders as a startup coach, I’ve developed a set of tools you can use to if not overcome your self-doubt fully, at least stop it in its tracks, examine it, and give yourself the mental and emotional bandwidth to deal with it rationally and move forward. Here are three you can try:

Create a Highlight Reel

The problem with all forms of self-doubt is that many of your self-critical concerns are not real, but they sure feel real. So, you have to gather evidence of your actual competencies, not just what your inner demons tell you. Namely, you need to create a highlight reel.

In Max’s case, we worked on his highlight reel on the spot. “I know that you’re daunted by having these setbacks,” I told him. “But that’s not the whole story. You’ve had plenty of successes. Let’s write those down.”

After a little prodding, I wrested about a half dozen examples out of him. He had raised so much money that other founders came to him to ask him for tips for raising capital, and some people jokingly called him “the VC Whisperer.” He had calmly guided the team through a massive product failure at a customer site and immediately gotten that customer to double their order, and the rest of the executive team (aside from the departing CTO) was excellent.

As we talked this through, Max calmed down. He even smiled. “This highlight reel could be a good thing for me to remind myself of every day,” he said to me. Absolutely! Create a highlight reel for yourself and look at it a few times a week as well as moments when you are having a crisis of confidence. It will help you keep everything in perspective.

See Yourself through the Eyes of Others

When Max’s critical voices got too loud, thought he was a terrible manager. That’s why he was having this severe talent problem. However, I had personally talked to his team when I conducted 360 feedback, and the reality is that they loved his leadership. He was a sincere person they trusted implicitly. He was humble enough to admit what he didn’t know, and he always painted an enthusiastic picture of the future, even when things were blowing up.

Did he have room to improve? Of course – we all do. But, overall, his executives saw him as one of the best leaders they had ever worked for and were enthusiastically and energetically working for him and the ultimate success of the company. His board was equally positive about Max’s leadership strengths. I pulled out the 360 feedback report and reminded him of how people saw his strengths. I then asked him to role-play a few of his executives as if they were talking about him. Yes, he was embarrassed, but he couldn’t help but see that he was his own worst critic by far. When you remind yourself how others see you, it automatically lets more voices into the committee in your head. The new positive voices can often stand up the negative voices and give you a better sense of how you really are.

Build Healthy Habits

The final tool in helping you deal with your imposter syndrome is to get on top of your state of mind by building healthy habits. A few years ago, one CEO I coach said, “It’s not just lonely at the top, it’s exhausting.”

That’s why, for the sake of the company, you absolutely must attend to your health – physical, mental, and emotional. Otherwise, even little things can knock you off your game. It is not just “eat your vegetables” because “eating your vegetables” somehow gives you the moral high ground. You do these things so that you can cope during difficult time, make good decisions under stress, and stay on an even keel when things get tough.

As Max and I talked, we did a checklist of the habits that he had built over the past year. Healthy eating? Check – he had signed up for a food delivery service that was working well for him. He had mostly given up alcohol. Fitness routine? Yes – he had a friend he ran with twice per week and a fitness trainer who came to him twice a week. Enough sleep? Ah…not so good. He had been working too late at night and it took a long time for him to calm himself down and then fall asleep. Because he was high strung, he woke up anxious in the middle of the night. To compound his problems, he often had early morning calls with Europe and late-night calls with Asia, which interfered with him keeping a regular sleep schedule.

I get it – it’s not always easy to get enough sleep. But, as I told Max, you have to try. I asked him to explore his nighttime habits and see where he could improve. Perhaps, he could go to bed earlier when he didn’t have late night calls, or maybe he could get off his devices and do calming things in the evening so that he didn’t get so spun up right before bed. I also asked to add a day or two of fitness to his schedule if he could – we agreed that he slept better on days he worked out.

You need to diagnose your own habits to see where you need to upgrade, but I promise you this: if you upgrade your physical health, your mental health will follow.

As a startup founder, you have a lot of problems and pressures. That’s normal. You may feel like an imposter or have some self-doubt. That’s also normal. But, by intentionally putting in place these specific strategies, you will have a much better change of dealing with the darkness and accessing, much more often, your inner lightness.

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