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 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

  • Investing by yourself is uncomfortable, so many investors wait until others are investing before making a decision. However, a lot of the best startup investments in history have been cases where a single person invested even when no one else would.
  • Investing before clear signs of traction is uncomfortable, so many investors wait until there's proof that a company is on to something. However, the best returns come from being willing to invest before it's obvious that a company will be successful.

Founders

  • Asking for feedback on your ideas is uncomfortable, so some founders avoid customer feedback and end up building something which doesn't have a real market.
  • Firing mediocre performers is uncomfortable, so many founders let them stay in the hopes that they'll eventually improve. However, that usually hurts company culture, decreases company effectiveness, and pushes strong performers to leave.
  • Relinquishing control is uncomfortable, so sometimes technical founding teams will try to do sales themselves instead of hiring professional salespeople. This usually doesn't go well, but people don't like to admit they're ineffective, so they push on and slowly drive their companies into the ground.
  • One key lesson from the book Traction is that companies have dozens of marketing channels to choose from, and usually only one or two of those channels will work well. However, a lot of founders will just try the channels they're already comfortable with, and will avoid unfamiliar channels (e.g. billboard advertising or cold calling). Not trying many possible marketing channels before going all in on the best one greatly reduces the likelihood that a company will build significant traction.

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?