When I founded my first company Connected back in 2011, I was really surprised by the intensity of the emotional rollercoaster. By then I’d already worked everywhere from large corporate Microsoft to tiny new startup and felt prepared. I was dead wrong. I remember describing it to a friend as, “After I started a company, everything became 10x more intense. The highs and lows filled with terror, sometimes all in the same hour. Everything else I’d done in my professional career fades in comparison.”

In retrospect, I may have made every mistake in the book. I made the company the core of my identity and self-worth. Churned customers and even chance negative remarks were crushing and the metrics controlled the oscillation of my mood. When Connected launched on TechCrunch, the post was flooded with negative comments because we’d done something unthinkable at the time – we’d launched with a 14-day paid trial and weren’t giving the product away. The self-doubt was agonizing and we debated pricing long into the night. In hindsight, this turned out to be one of the best decisions we’d made because it focused us on the users which mattered.

I had impostor syndrome before I had a name for it. We were just some kids working out of a one-bedroom apartment, and that feeling made it difficult to go out to events and pitch the company on stage. I worked intensely, considered weekends nonexistent, and dropped almost all my outside relationships, rarely having one-on-one conversations with anyone that wasn’t work related. 

And all of this happened with a pretty successful story as we raised funding and ultimately sold the company to LinkedIn!

Looking back now, I realize how unprepared I was for the emotional toll of being a founder. There’s something uniquely difficult about being a startup founder that I didn’t know to expect.

The challenges of being a founder

I’m writing this as a way to share some of the unique insanity that pervades the founder experience. My hope is that others will be a little more prepared and to offer a little relief if you’re struggling with these feelings now because you aren’t the only one. In no particular order, here are some of the challenges that I’ve struggled with myself or noticed others have faced too. It’s a hard job, and this is a pretty long list!

  1. The lack of structured days. What should I do today? What is the right way to focus my time and energy? When you’re starting a company, it starts with sitting at your desk and deciding what you want to do. The early startup experience removes the comfort of a boss, clear objectives, scheduled meetings, and the rhythms of operating within a team. The need to build a plan from scratch AND execute on it is a unique challenge.
  2. The lack of feedback. Am I doing the right things? Did any of the work I did today matter if the business isn’t moving? In an academic world, there are grades and GPAs to provide regular feedback on progress. In the corporate world, there are titles, compensation, performance reviews, and peer feedback. In society, there’s status from your employer and profession. Startups are like a black hole for feedback. No one tells you you’re doing a good job, and most of the world is demanding more. The clear milestones for achievement aren’t availableand replaced with highly ambiguous ones.
  3. The lack of data to make decisions. Is this the right decision? Will this work? Starting a company is like charging down a path without a map and hoping that you’ll burst into clarity later. There are reasons to second guess every decision you’ve made, like my earlier story about launching Connected with a paid trial. I call this high ambiguity environment “the fog of war,” where it’s unclear whether or not things will work and quick decisions must be made based on conviction rather than data.
  4. Completely justified Impostor Syndrome. Am I cut out for this? Do I have what it takes? Founders are often critically unqualified for their roles. Objectively, they would not have passed an interview process for their role or level of responsibility. As their businesses scale, they find themselves in positions of leadership, management, and cross-functional responsibility which they have to rapidly to grow into. This is everything from how to actually operate a business to critical soft skills like how to hold others accountable. When your whole team is counting on you, the pressure is intense.
  5. Intense highs and lows. There are certain milestones of running a company that take up large blocks of time and emotional energy: fundraising, hiring, firing, restructuring, churning key customers, etc., all happening at the same time. It was thrilling to have the first investment check hit the bank account and feel the validation that someone believes. But a quick follow-up was mapping out our runway and contemplating certain death if we don’t figure it out.
  6. Your identity is your startup. It is really difficult not to deeply tie your identity and self-worth to your startup. I think we all know we shouldn’t, but it’s very common to feel so much ownership that moods fluctuate with ARR and churn, self-worth is in lockstep with fundraising, and every comment feels personal. Successful companies are a combination of skill and blind luck, and it is possible to do everything right and still fail. It’s really hard to keep this fact top of mind.
  7. It’s a sales job. Sales is an integral part of the job. Founders are always selling their idea and painting visions of what it will become. From fundraising to hiring to management to closing sales, it’s a relentless sales process to try to eke some yes’s out of a sea of no’s. This can be intensely demoralizing and stressful. It’s a rare subset of the population that is cut out to be in sales, and it’s a surprise to many that this is a core part of the job.

An additional insight into a lot of these challenges: it’s incredibly difficult for founders to get support. There’s is a “We are crushing it! Up and to the right!” bravado and highlighting of winners within startup culture which pushes relentless optimism without room for conversation about hardship. It feels like everyone is winning except you.

Also, there is a clear downside for talking about problems – who do you talk about them with? If you talk to your investors, you could impact your next round. If you talk to your cofounders and employees, you could demoralize them. If you talk to your partner or friends in your network, maybe it’ll bite you later? Would they even get it? Not to say that this is true, but the paranoia isn’t uncommon.

Dealing with the problems

A lot of entrepreneurs struggle when they hit these challenges, and are constantly tested at certain decision points such as heading into another cycle of fundraising, evaluating their exits, or pouring more years of their life into their startup. So what do you do to manage this? As you hold everything together and grow your team and business, here are some strategies that might be helpful to you.

  • Expect it and normalize it. One of the reasons why I’m writing this post is to shed some light on the challenges of being a founder. Invariably you’ll hit bumps. Finding ways to manage your expectations can reduce the intensity of the highs and lows, and normalizing it as part of what founders go through can make it easier to bear.
  • Build your support before you need it. I don’t mean joining a founder community and humblebragging. Form real relationships where you can have Real Talk and have trusting and vulnerable conversations. Maybe this is with family, friends, or making an effort with other founders you meet. This will be useful and helpful to you in those crucial moments.
  • Diversify your portfolio. It’s tempting to devote 100% of your time and mental energy to your startup. This is a mistake. It is not sustainable in the long-run because you’re shelving everything else in your life, and the challenges get magnified to epic proportions without anything to offset them. Invest in finding other outlets and take care of yourself. This can be exercise, relationships with friends and family, hobbies, and personal passions. There is nothing wrong with this and it is a healthy and good investment for you.
  • Focus on yourself, today. Not your legacy, not the story others will tell, not the way others will perceive you. It is a rabbit hole to always think about the big picture and the hypotheticals of where this will go and what might happen. What is the one big thing you want to accomplish today to move forward? Focus on impressing yourself and your needs now, and see what comes.
  • Celebrate wins. There is scientific evidence that practicing gratitude can change your brain. There are many approaches to this that aren’t just gratitude journals, from thanking others to counting your blessings to mindfulness practices. It’s worth looking into.

There is no magical panacea for the founder’s journey, but with time and some hard-earned wisdom I’ve found that it does get easier. I could write a lot more about this, but I’ll save thoughts for next time. 🙂