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I’ve been seeing this convergence-divergence cycle as a founder as well. We are forced to be like an octopus doing full-court press in 8 different disciplines to build a bootstrapped startup. Your inner engineer always cursing at your inner creative, and occasionally getting disillusioned when your customers don’t respond well to some feature or tweak.

How to keep morale and quality and technical debt at bay? If you have the answers please share, here are some of my steps to combat the above:

1. Your brain plays some steps better than others at certain parts of the sleep cycle. Knowing when to do what so you do it well is half the battle. Example: no brainstorming or solving complex problems when sleep deprived, but yes to grinding through mundane easy but boring tasks when sleep deprived (your brain is too tired to care so it doesn’t hinder with distractions / ADHD ).

2. Step back from some tough tasks and go to a different environment then let your brain sleep on it or wander before looking at them fresh. Prioritize as if someone else is doing the work and validate everything with quick prototypes/calls to users instead of putting in large effort on assumptions.

3. Having kids has helped, ironically. If your break involves spending time with them and teaching them, breaking down the problems for them and talking through with them helps see things clearly as well.




Word of warning, your kids may grow up with strong opinions about product management, corporate governance, user interaction design, and service business value propositions. It happened to me


Nodding in agreement: I'm also a child of serial entrepreneurs. Felt lonely thinking about all of that all day every day, until I went to grad school :) There needs to be a peer support group for children of entrepreneurs.




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