Navigating the Startup Crossroads of when to Persist and when to Pivot

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I have gotten this question a lot recently from entrepreneurs: how do you know whether or not to stick with your startup? Does it just require grit to push through or is your time better spent moving on to a new idea?

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Are you still passionate about the business?

This is the first question I ask. Building a startup is so hard with so many challenges. If you are not super passionate about the problem/space you are solving then the slog can wear you down. If you have lost that passion, it may be time to consider moving on to something that does ignite your passion.

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What have you learned about the market and authentic demand?

Through your early journey, what have you learned about the problem being must-have versus nice-to-have? When you speak with customers, what have their reactions been? Do you have loyal, passionate customers? Do you want to build a big business and if so, is there a path forward? Does the market confirm there is authentic demand and the message/solution is not quite right? Or do you feel like you keep jumping around to the next unrelated thing or customer segment in the hope of finding something? 

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What have you tried in previous pivots?

There are many different types of pivots; some big and some small. Both could be required, but is the pivot driven by insights or a hope that something different will magically work? With any previous pivots, do you feel like you are getting closer to solving the customer problem and they are inviting you in to keep working with them? Or do you feel like you keep trying to sell something they do not really want?

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While there is no perfect answer, I have seen that multiple pivots are usually required to successfully find the right path. Each pivot is met with new insights and deeper learnings that can propel you forward. However, at some point, you feel like you are pushing customers versus them pulling you in to solve their problems. Or you realize that even if you get it right, the outcome will not be worth your time. In that case, it is probably best to move on, reset, and start something different!