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.

20 Sep 2016, 1:41am | 7 comments

  • Arman Tokanov

    Great point. Also, I think, another factor is that even if you don’t do major pivots the actual day-to-day activities will probably change significantly as the startup evolves. So even if someone will broadly be doing the “same thing” (e.g. supply chain management), the actual actions, which really define the experience, at the end of the day, will probably change anyway.

    • DanShipper

      Also true!

  • https://www.hardbound.co Nathan Bashaw

    Great post! Along the same lines as your “am i learning” question, here are some questions that have helped me:

    * Even if this all fails, will it still have been worth trying?
    * If we succeed doing this, will I be proud of what I’ve done?
    * When I’m old, how will it feel to explain what I did to my future kids?

    These questions all get at the moral core of a startup. To me, the thing that pulls me through is having a purpose that’s higher than just making a lot of money. Because lots of times it’s very unclear whether that will ever actually happen.

    Obviously everyone has to discover their own style of answering these questions, but this way of approaching it has helped me a lot.

    • DanShipper

      Excellent! These are amazing, totally agree.

  • Sheena

    Enlightening as always, Dan 🙂

    • DanShipper

      Glad you enjoyed it!

  • http://brandonhilkert.com/ Brandon Hilkert

    Hey Dan – really enjoyed the post. It’s definitely helpful to the find that questions that motivate you. Similar to you, learning is high up on my list. I wonder if some people don’t know what those questions are and so it’s hard to ask them to give direction. Probably takes a little more introspection than most articles dig in to. I wrote an article about the things that I’ve found helpful to ground me in new opportunities: http://brandonhilkert.com/blog/care-about-what-you-build/. Somewhat more extreme, but answers a similar motivation question. Would love your thoughts if you get a chance to check it out.


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