The Road to Success is Paved with Discomfort

TL;DR: If you’re a founder and you want your company to succeed, you have to put what’s best for the company ahead of what feels most comfortable for you.

One of the first engineering teams I was on had a lot of micromanagement. The tech lead did (unsolicited) reviews of everyone’s code, and also gave implementation tips for new features down to the “you should write a function called XYZ” level. If you’re not an engineer, that’s akin to giving a writer a list of paragraphs to include in their short story.

Senior developers on the team were frustrated by this level of micromanagement, but I thought it was great. My main programming experience was in college, and having a smart tech lead tell me exactly how he would implement each feature was a wonderful learning opportunity.

At the next company I worked at, things were very different. After I spent a few days getting oriented, my boss sat me down for a chat and asked me what I’d like to build. I wasn’t sure what he meant. Wasn’t he supposed to tell me what to work on? It turns out that’s not how the new company operated. At the new place, engineers decided what they wanted to build and how they wanted to built it, and then they’d simply start coding.

I’ll admit it: I panicked. I knew I had good programming fundamentals, but I also had a lot of self-doubt. I had never designed non-trivial software from scratch. What if I made a bunch of mistakes? What if my designs turned out to have flaws? What if the company decided they shouldn’t have hired me? I explained to my manager that I wasn’t sure I was ready to take on so much responsibility, and he replied, “I think you underestimate yourself. Give this a try and see what happens. I think you’ll be pleasantly surprised by the results.”

The words of encouragement helped, but only a little. What helped even more was that I didn’t really have a choice. I had to do what my manager asked, otherwise I’d lose my job. So, I found a project that interested me, designed and implemented some software for it, and the results were good. That success gave me a confidence boost, and over the next few years I took on more challenging work and became more willing to step outside of my comfort zone. I ended up learning much more from being thrown into the deep end than from being an apprentice, and I became a much more effective engineer. And and it all comes back to that reassuring conversation and being forced to overcome my discomfort.

Fast forward to today, where I’ve now been a VC for almost 3 years. When I first started investing, I thought the reason companies failed was because they ran out of money, or because they didn’t build something that people wanted. Those explanations are true in a literal sense, but I think the underlying cause of failure is that many founders are afraid of discomfort. Of course, it’s not just founders who are afraid of that, it’s employees, investors, customers, and… well, pretty much everyone.

By definition, discomfort doesn’t feel good – and people like feeling good. The problem is that sometimes the uncomfortable thing to do is the best thing to do. Below are some examples of how avoiding discomfort as a founder or investor can lead to poor results.

Seed-stage Investors


At a company-wide level, the Innovator’s Dilemma can also be seen as the repercussion of doing what’s comfortable in the short term instead of what’s best for the company in the long term.

What’s the solution? If you want to be successful, you have to be willing to push through discomfort. If you’re a founder, you’re going to have to fire people, you’re going to have to talk to customers and sometimes hear negative feedback, and you’re going to have to make cold calls. If you’re not willing to do those things – or at least hire someone else to do them – then that’s okay, but your likelihood of succeeding will drop dramatically. At the end of the day, you have to ask yourself what’s more important: your comfort and your ego, or your success and your company’s success?

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