How I Conquered Self-Doubt As A First-Time Startup Founder

“Impostor syndrome” is what it sounds like—the feeling that you’re a fraud, you’re in over your head, and you’re about to be found out.

How I Conquered Self-Doubt As A First-Time Startup Founder
[Photo: Flickr user Siris]

It’s 4 a.m. and I’m not sleeping. I’m wondering if my company will make it to the next quarter. I told the board, my team, my investors–I told everybody–that everything would be fine. But truthfully, I don’t know if it will.


Those were the thoughts that kept me up at night as a 28-year-old tech entrepreneur who’d started a digital video company that would later go public. Of course, I didn’t know that then. Here’s what I did know: We had a good product, customers were interested, and we were about to expand overseas.

At the same time, I wasn’t sure if the contract details we were considering were right, or whether the rep I’d just sent to China would get arrested when his flight landed, thanks to some regulation or other I might’ve missed. Oh, and what exactly was our pro forma cash flow statement supposed to look like? The truth is, I felt like I had no idea what I was doing.

Enter The Impostor

“Impostor syndrome” is exactly what it sounds like–the feeling that you’re a fraud, you’re in over your head, and you’re about to be found out.

Like a lot of first-time founders, I didn’t know what to do with the stress and anxiety that caused me. To be sure, there’s a permanent voice in just about every CEO’s head that second-guesses their decisions and plagues them with self-doubt, but it can be especially strong among first-time leaders. And it can make the job a lonely one.


But, like every good startup challenge, facing down that feeling is an experience you can learn from and turn to your advantage. Here’s how.

1. Go Ahead And Freak Out

Running a company for the first time is overwhelming. It wasn’t that I was doing a bad job, I just had a lot of people depending on me for answers. I was a product guy, and being CEO meant pulling away from what I wanted to work on the most—the actual product. It also meant I had to go from “I have this awesome idea” to “shit just got real.”

All of a sudden, you actually have to run a company, which includes handling legal issues, financial issues, process issues, and issues that don’t even fit into clear categories. You’re going to worry a lot. You’re going to have sleepless nights. You’re have moments when you’re uncertain about what to do next. The important thing is to recognize all this, embrace it for a moment, then stop feeling guilty about it and start problem solving.

In other words, let yourself freak a little, then get back to work. It’s a skill you’ll use in leadership roles much further down the road.


2. Hire A Strong Leadership Team

The smartest thing I did as CEO was hire smart people. That sounds obvious, but it isn’t so easy in practice. Under pressure, uncertain startup founders tend to have the reverse impulse–to buckle down and try to manage everything from the top. You might be afraid that hiring world-class talent means you’ll look worse by comparison.

It’s actually the opposite. You should actively try to hire people that you feel are better than you. You’ll all benefit individually from the pooled skills and expertise of your team, as well as from what you can accomplish together. No one does it all alone, and if you attempt to, you’ll only compound your self-doubt.

My first hire came after too many nights of waking up and thinking, “Oh God, do I have enough cash to get to the next quarter?” I had a limited finance background, and it turns out that years of balancing my personal checkbook just wasn’t enough. Just as we coach business-oriented CEOs to go out and find an amazing technical cofounder rather than learning to code, I realized I was spending way too much time trying to become a finance person instead of playing to my strengths.

After making that first hire, I instantly felt better. It was a giant weight off my shoulders. I did my job better, knowing that the numbers were being looked after by a professional. Looking back, I wish I had hired all of my key positions earlier. Still, it’s important not to forget that you’re still the CEO, and responsibility ultimately falls on you. Don’t just hire people, leave them to their devices, and hope for the best. Spend time to work through the details collaboratively. Ask stupid questions. They just might save your company.

3. Talk It Out

Somewhere in your leadership team, or on your board, or even with a professional leadership coach, you need to find someone to talk to. I got lucky. That crucial hire, my CFO, also became my “guy.” He had my back and we went to war together. He had a strong business mind, was whip smart, and thought about things in a more process-oriented way, which added to my perspective. I was never alone with my thoughts and concerns, and just running these things by someone helped me make better decisions.


It’s also a good idea to connect with other startup founders in a similar position. They’re probably going through the same problems, so you can bounce ideas off them and get advice. Check with your investors, your alma mater, and industry groups, and look into organizations like YPO and FounderDating. Whatever you do, don’t hesitate to get expert advice or coaching to help you keep a good perspective.

Truthfully, freaking out and screwing up made me a better CEO. It was sort of like moving to a foreign country without knowing the language–you have to pick things up on the fly and adapt, and it leaves you with deeper knowledge, empathy, and practical experience. To be sure, it was the most uncomfortable situation of my life, but learning to embrace self-doubt as a business leader is a skill in its own right–and it comes in handy long after you’ve stopped being a first-timer.

Ajay Chopra is general partner at the VC firm Trinity Ventures and former CEO and founder of Pinnacle Systems. Follow him on Twitter at @AjayChopra.