Would I do this for 10 years?

Let me tell you something I believe that I think most people in tech don’t:
If you’re a young entrepreneur just starting out, asking yourself “Would I do this for the next 10 years?”, as a way to figure out whether or not you should be working on something, is, in my opinion, totally unhelpful.

This isn’t because I’m advocating against a long term approach. I think it’s great to work on something for a long time.

Rather, I think it’s a bad question because we’re just not good enough at predicting our desires over the long term to be able to answer it. We’re capricious animals. We’re generally fickle and impulsive. We’re maddeningly mercurial.

Mostly this advice is given by 50-year old investors to 20-year old founders as a way to figure out what they should work on. But I think it misses something important: when you’ve never worked on anything for more than a couple of months, you don’t have the tools to judge whether your answer to this question is reflective of temporary enthusiasm or something more lasting.

I’ve seen this first hand. I can’t tell you how many of my friends have come to me at some point or another and say things like, “I feel like I’ve found it! Supply chain management is what I want to spend the next 10 years on!”

With a few exceptions, they’ve almost always moved on to something else within a couple of months.

Most pressingly, when you’re just starting out, I think asking yourself that question can be actively harmful because it sets the bar too high. If you’re constantly asking yourself, “Would I do this for 10 years?” for something you’ve just started, the answer is more likely than not to be “No” at a few points along the way — given the extreme ups and downs involved in starting a company.

When you ask yourself that question, you’re focusing on surface-level results which tend to fluctuate randomly early on. Some days you’ll be on top of the world, and some days you’ll be down in the dumps. It’s a bad habit to draw long term conclusions (like whether you should be working on this long term) from short term results. It will make it much harder to manage your psychology.

Instead, it’s more helpful to ask yourself questions whose answers don’t depend so entirely on how things have been going that day. For me, the most helpful one was this:

Am I learning? Importantly, am I learning what I want to learn?

If the answer was yes — and at Firefly the answer was mostly yes — it gave me the stamina to keep working even when things didn’t seem to be going my way. And that can make all the difference.