When Should I Give Up?

When should I give up on something and when should I see it through?

I’m asking this question after my third attempt this week at writing a blog post I’ve been thinking about writing for the past year.

The idea for the blog post seems so promising when I think about it. I’m able to imagine it in its fully finished form and I can picture the effect it would have on the reader.

But the words don’t flow when I sit down to write it. I can’t seem to thread a cohesive narrative for the reader that is engaging and educative at the same time.

This doesn’t always happen to me. Sometimes when I sit down to write a blog post the words seem to just pour out of me as if they desire to escape my head and be on the page.

This mental block isn’t unique to writing blog posts. I’ll run into it any time I’m doing something that requires creativity and isn’t just rote execution. Like when I’m building a side project and I just can’t structure the code in a way that makes sense. Or when I’m pursuing a business idea and it just seems like no one cares and I’m not actually solving a problem.

Should I always expect it to be easy? Is getting blocked my subconscious’s way of saying that I’m working on a bad idea and it isn’t worth my time? Or, on the other extreme should I always try to push through these mental blocks? The idea being that struggle is a prerequisite for doing something great.

Both of these diametrically opposed positions feel wrong to me. I can think of examples on both sides where giving up or pushing through were the right call. It scares me to waste my life working on things that will never succeed. Yet I’m equally scared of spending my whole life bouncing between projects without conviction and thus never creating something meaningful.

I don’t think that there are any right answers here. And if there are they lie in a blurry middle ground that is constantly shifting. My intuition says that knowing when to give up or keep going is part of the craft. Going forward, when I feel blocked I’m going to try and ask myself the following questions to see if I should give up or keep going.

• Am I blocked for internal (I can’t do it) or external (no one wants it) reasons?

  This is a hard thing to figure out but very insightful. Internal blockers are probably best pressed through. External blockers are often an indicator that what I’m doing isn’t worth it. Fair warning though that the greatest innovations often come from pushing through external blockers e.g. basically every new technological innovation.

• How many times have I tried?

  If I’ve only tried something once or twice, maybe I just haven’t tried hard enough and should give it another go. What’s the upper limit on the right number of tries? Is this proportional to the difficulty of the project?

• How passionate about this am I?

  If I’m not passionate about something it isn’t worth doing even if I succeed. In the startup world this is often called product-founder fit.

• What am I doing instead?

  Is the alternative to pushing through the mental block sitting on the couch and doing nothing? I should probably keep working. Is the alternative working on a new idea that I can’t stop thinking about? Maybe it’s a good idea to go pursue it.

• What have I been doing too much of?

  If I’ve given up on the past five things I’ve tried, then maybe it’s time to stick it through on one. The inverse is also true.