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Doubting Myself Every Day Makes Me A Better CEO

Heidi Zak

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ThirdLove was about to move into a brand new office, and the other day I was walking around our old space, thinking about the time we’d spent there.

I had this sudden surge of uncertainty and started thinking, “Oh my god, I’m employing all of these people.”

It was a moment of stress that seemed to come out of nowhere.

Am I making the right decisions? Am I doing everything I can to make our company really successful?

The thing is, I’m more confident than ever in my abilities as a leader and the business as a whole. But even now, almost six years after founding my company, I still have moments of doubt like this.

I don’t think self-doubt ever goes away. And honestly, I think doubt can make you stronger as a leader.

It forces you to ask these questions, as I asked myself, about whether you’re doing everything in your power to make your company successful. It forces you to evaluate your own leadership.

Of course, too much self-doubt can be crippling. But a healthy amount will keep you on your toes.

Here’s how it happens:

When you recognize you’re not perfect, it pushes you to be better.

If you genuinely have no doubts about your abilities, you also have no incentive to improve.

Those moments of doubt can be frightening. They grab hold of you for a few minutes, or hours, and make you unsure of yourself and your decisions. When it’s over, you know you don’t want to feel like that again.

And the only way to make that happen is by developing yourself.

What caused your moment of uncertainty? Whatever it was, that is precisely what you should try to get better at.

Self-doubt can be a strong motivator because it helps you recognize your weaknesses — and where you should focus to become a better leader.

If I were to walk around all day thinking I was amazing, it wouldn’t be good for the company. And it certainly wouldn’t be good for my own personal development. I would have no motivation to improve, no hunger, no drive.

You learn to ask the right questions and make a plan.

Questioning yourself is the essence of self-doubt. When you’re unsure of yourself, you question your abilities as a leader.

At some point, you’ll find yourself reacting to a situation you didn’t expect. You’ll realize that something isn’t working or you’ve made a mistake. That’s when the doubt will creep in.

That’s not necessarily a bad thing, though. If you take those questions seriously, address them, and make a plan to figure out what you could do better, then you’re turning a negative situation into an opportunity to grow.

You won’t always feel great about how things went, but you can learn from those moments and come out a better leader on the other side.

Over time, you’ll start to realize that it’s easier to get through these situations and accomplish great things.

You’ll always doubt yourself after a mistake. It’s natural. So, ask those questions of yourself, get the answers, and then move forward.

Building confidence allows you to take more risks.

Someone who doesn’t take risks — who’s afraid of failure — will never become the founder of a company.

I say that, because the chances of failure are fairly high. In fact, it’s 100% certain you will fail at something along the way. It’s an inescapable truth.

And, odds are, it’s going to happen more than once.

At one point at ThirdLove, when we started growing super quickly, we decided to outsource our customer service overseas. I felt like it was the right move at the time, but we quickly saw that the level of service our customers were receiving was not up to our standards. Our customers weren’t happy, and I was doubting myself tremendously.

We didn’t let the failure derail us. In fact, it was the impetus we needed to create our own customer service team right here in California. Even though it was stressful at the time, that failure was a learning experience that led to something much better.

Your goal as a leader should be to make the right decision most of the time. But “most of the time” is about as much as you can hope for.

When you do fail and begin to doubt yourself, don’t let it overwhelm you. Use your doubt constructively to decide where you can improve and grow.

Heidi Zak is the co-founder and co-CEO of ThirdLove. Prior to ThirdLove, Zak cut her teeth in retail at Aeropostale where she quickly rose to Director of the retail giant, launching and running the International Division, before becoming a marketing executive at Google. Zak holds an undergraduate degree in Economics from Duke University and an MBA from MIT Sloan. In her free time she loves spending time with her two kids. Heidi has been named one of Fast Company’s Most Creative People, Goldman Sachs 100 Most Intriguing Entrepreneurs, Business Insider's 30 Female-Founded Startups to Watch, and SF Business Times 40 Under 40. Follow her on Instagram: @Heidi.

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