A Crisis of Confidence

For the last nine years, I’ve observed a serious challenge in the startup world. I’ve experienced it firsthand in my own ventures, discussed it at length with my entrepreneur friends and even co-launched a couple of organizations with the goal of addressing it head on. It’s a challenge faced more intensely in startups than almost anywhere else, one that far too often leads to serious depression, burnout and even suicide. It’s the challenge of confidence—a challenge so serious, we're calling it a crisis.

Much has been written about the high rates of depression in Silicon Valley. Brad Feld, a thought leader in the tech and startup world, has some powerful stuff on this topic, and many others have analyzed the correlation between working in a startup and emotional and mental strain. Business Insider cites a study by Dr. Michael Freeman (entrepreneur and clinical professor at USCF):

Depression . . . was present in 30% of all entrepreneurs . . . That's a much higher percentage than the US population at large, where only about 7% identify as depressed.

The fact that startup culture can cause mental strain isn't groundbreaking. But my goal here is to personalize the research with some of our own stories. In doing so, I hope to encourage continued conversation on this topic and help broaden its scope to include non-founders.

Over time, and thanks to the bravery of our team, Astronomer has begun to foster a culture friendly to sharing real struggles. Since one of our core values is Openness, several team members have agreed to let their stories be shared publicly. Let's start with one of the main reasons confidence begins to falter:


The pressure to perform at the highest level in a startup is the most intense pressure I’ve ever been under! In my case with Astronomer, though, it’s not the threat of consequences that drives the desire to be the best but the sense of ownership of my chunk of Astronomer’s success and the fear of letting my high-performing colleagues down. Couple this with societal, cultural and industry expectations outside the workplace, and it’s enough to make one crumble under the weight. I’ll admit—I did crumble, big time. My expectations for myself were unrealistic and unachievable, which created an unending cycle of self-doubt, negative self-talk and ‘you're not good enough’ syndrome.

Until now, my career experience has lead me to believe that it’s crucial for me to be rock solid, confident and unswayed. I’m supposed to 'lean in.' In the startup environment, however, I’ve realized that I’m fortunate enough to have a team to lean on, and that has helped ease the pressure to achieve excellence. 

  • Becky, Account Executive

When I think of confidence, it seems subjective, totally up to one’s self-perception—“a feeling of self-assurance arising from one’s appreciation of one’s own abilities or qualities,” according to the New Oxford American Dictionary’s “Special Usage” section.

I was a bit surprised to read Oxford’s main definition, which says confidence is “ the feeling or belief that one can rely on someone or something; firm trust.” Likely a symptom of my American individualism, I fully expected the definition to center around a person’s self-perception, not this broader application. Words like “rely” and “trust,” while applicable to one’s self, seem to indicate the involvement of an external party. In my experience, this is not the typical context for our use of “confidence.”

I think the difference between these two definitions is perhaps a critical point. One of the most common experiences I’ve witnessed inside of startups—particularly venture-backed startups—is the sense of isolation created by talented, highly-motivated people working toward an incredible goal. It’s almost counter-intuitive as you’d expect an environment of motivated people chasing a shared and exciting goal to lead to a comradery or a “foxhole brotherhood.” But it doesn’t, usually.

More often, we’re threatened by the talent and passion of our colleagues—which gives way to insecurity about our own contribution and relative value. Becky described this sensation even though she was one of the easiest, no-brainer hires we’ve made and has absolutely crushed her role!

I’m not saying contribution and high performance aren’t critical in a startup. But confidence must be derived from something else.

So, what can you base your confidence upon? This is a concept far deeper than I’m capable of doing justice, but I think a possible secret lies in the definition: “the feeling or belief that one can rely on someone or something; firm trust.” Could reliance on and trust in others be the source of true confidence?

Maybe you can get this in your company, but often you can’t. This crisis is pervasive and many startup cultures actually foster it. If you find yourself in such a place, you’ll need to look outside of the office. Who in your life can you count on to “have your back” or help in a time of need? Who can you “rely” on and “trust”?

Asking these types of questions can help to build a strong foundation of confidence. But this crisis isn’t only born out of a lack of a reliable support system. There are some other intense dynamics at play here:

Failure or the Fear of Failure

The roller coaster of emotion you feel as a startup founder is not for the faint of heart. Each day carries a different feeling, sometimes of confidence that you've never felt before and sometimes of uncertainty that's nearly unbearable. As is so common with founders, my startup became my identity. When a potential investor said no, it felt like he was saying no to me personally. When someone liked my idea, it felt like they were affirming me as a human.

The hardest part for me was when I realized that we had to close down operations. In fact, the day I told one of our two employees that we could no longer pay him was one of the lowest moments of my life. He was a friend, and he had moved from a different city to be a part of my dream. I felt not just his pain, but the pain of all the people who'd believed in me and invested so much time and money into my company, into me. Before this, even on the darkest days, I rested in the idea that people were behind me and that we just needed to push through to reach our goal. When I let my friend go, my confidence fell like a house of cards. I felt like a fraud.

My startup was my life and when it went away, it felt as though my identity went with it. I fell into a depression unlike anything I'd ever experienced before. Like a lot of people, I'd experienced sad and difficult seasons, but this was something different. I felt numb. It felt like it went beyond sadness, into a place where I didn't really feel much of anything. I believe it was my mind's way of dealing with the pain of losing a huge chunk of my identity. My confidence was gone.

Every founder believes that his or her startup is the next big thing that will change the world. This is critical. You must carry the burden of confidence, and somehow turn every 'no' from an investor into a reason to bolster that confidence. I 'knew' that one day those foolish people would see my startup's success and know that I was right all along. When everything failed, I was overwhelmed by the feeling that maybe I was the fool all along. And that almost immediate shift in confidence is something I still deal with now, over a year later.

  • Chris, Creative Director

Failure is a powerful growth and learning mechanism. I know that’s not new—frankly, it’s probably cliché—but I seldom consider how seriously fear of failure affects my daily confidence.

Chris’s story is a common narrative about the powerful effects of failure on identity. But why is that? At the end of the day, what really took place in Chris’s story?

One way we could view it is the following: Chris and his co-founder took an idea that they loved and poured their time and energy into trying to build it into something tangible. They found others who were passionate about their idea, with skills that could help bring it to reality, and hired them. They brought friends, family and investors alongside to support its growth. They read anything relevant they could get their hands on, researched the industry and business model, uncovered processes and methods for construction and laid the foundations for growth. They learned how to pitch, how to hire, how to fire, how to do taxes and investment docs. They learned a huge amount of what it takes to start and build a company.

But most importantly, they learned what not to do. Chris could probably give you a doctoral thesis on mistakes he made and things he would have done differently. This kind of hindsight is gold! It not only puts Chris miles ahead of the game for his next startup, but it makes him a HUGE asset to Astronomer. Almost daily, he challenges the decisions we make or the processes we deploy. He can do that because he’s seen what works—and what doesn’t.

We have to kill the stigma of failure in startups. I’m not trying to trivialize the pain of failing. I am, however, trying desperately to trivialize the belief that failure in any way makes you less valuable. Failure, once the dust settles, is a major asset and should be a source of confidence.

It may not come as a shock that isolation and failure play a role in confidence, but there’s one more angle I want to investigate:

Confusion and Complexity

Joining a tech startup is one of the hardest things I’ve ever done. Getting in at an early stage has its pros and cons naturally, but overall, it is what seems like a never-ending challenge. When I left the last company I started to join Astronomer, I figured I’d be able to tap my network and get quite a few good leads—and ideally a few deals to jumpstart the growth team. In theory, that is a hell of a plan, but I didn’t take into consideration the fact that we didn’t have an exact product yet . . . or much supporting material.

Fast forward a few months and it was the SAME story. That’s when it began toying with my confidence and emotions. I started to ask questions: Am I good enough for this? Would someone else come in and be better? WHY HAVEN’T I SOLD A SINGLE THING?! I had to tell myself, 'Just keep pushing.' But I started to doubt myself. Luckily, we had founders who understood that even though we didn’t have a product to sell, it was still beneficial to talk to prospects. 

  • Brad, SMB Sales Director

My dad once told me that business is just “logic wrapped up in jargon.” The land of startup is riddled with intimidating terms and concepts. The perfect ten slide pitch deck, three-year cash flow model, scalability metrics and design thinking . . . there are dozens, maybe hundreds, of blog post headlines that can disorient and distract from the logic that first instigated your great idea. Startups are trendy, and this trendiness has led to an insatiable amount information sharing. But at the end of the day, a vast amount of this information is repackaging the same basic building blocks and logic.

When faced with all you have to accomplish in a startup, each one of these new metrics, processes and concepts adds significant stress. It doesn’t take much to completely overwhelm and ultimately discourage you.

Brad has a strong sales intuition, and he just kept approaching things logically. There were moments of intense confusion and insecurity as virtually everything he was doing was brand new. But he kept driving forward and an amazing thing began to happen: Each move he made taught him something, and over time he began building an experience-based understanding of SaaS sales, as well as gaining invaluable information about what companies really need, which helped shape the unique way we do SaaS. Today, Brad intuitively understands much of the buzzword philosophy that gets thrown around. He doesn’t need to read a book to tell you the best closing process for a given industry—he’s learned it through trial and error.

At Astronomer, we openly acknowledge that we engage in a daily battle with the crisis of confidence. We talk about how it impacts us, why it happens and how we can deal with it. We’re experimenting with ways to create “wholeness” across our team, whether that’s a company-funded HSA so that no health care costs come out of pocket; a monthly stipend to be used on mental health (Becky recently used hers for a National Park pass); or whole-team remote work trips (we’re heading to Nashville in November!). Someday, I hope to have tactical solutions for combating the crisis of confidence plaguing our profession, but in the meantime, find people to lean on, take pride in your failures and keep grinding through the barriers!

If you’ve faced (or are facing) this challenge and want to commiserate, feel free to reach out to me or anyone on our team. We’re an open book.

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