How to pick a side project strategically - Deepstash

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The Golden Trio

Use these three criteria to evaluate an idea:

  1. Longevity — Will it stay relevant for a long time?
  2. The monetization sweet spot — Can you make a living?
  3. Limited but extensible scope — Can you pull it off?


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Riding the hype train can get your project trending quickly, but you'll have nothing left when the hype is over. So find something that has longevity instead. What's something people will keep searching for in the coming decades? Email, DNS, online meetings, and timezone conversions are all examples of things that have a high and steady search volume.


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The monetization sweet spot

If your project can't attract any users, then it's obviously not going to generate any meaningful revenue, let alone allow you to eventually build a business around it.

Too much monetization potential, on the other hand, can attract regular businesses, or venture-backed businesses. So ideally, we'd be somewhere in between.


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Limited but extensible scope

You can't undertake a massive project on the side, so the scope needs to be minimal. Once an initial version is live, it should be extensible incrementally. Adding many small features that add up to a great product. Since side projects are primarily done in the evenings and weekends, the available time is usually chunked into sessions of a couple of hours.

That's another reason to find something that can be built iteratively. Try to ship something every other session.


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