An Ongoing List of Persistently Frustrating Problems

I’m not asserting any claim to these problems, nor am I validating them. I’m listing them here to commiserate and inspire. I invite you to submit the frustrating, persistent problems you experience in the form below.


  1. Determining the most important thing you should work on at any given time
  2. Small businesses (and startups) struggle to price
  3. Small businesses (and startups) struggle to sell
  4. Small businesses (and startups) don’t know how to engage customers
  5. People have a difficult time identifying what the obvious next action should be
  6. People don’t know what their super power is
  7. Proactively measuring coronary blockages is imprecise and expensive
  8. People struggle to successfully collaborating asynchronously
  9. People don’t know how to effectively use a calendar
  10. People make low value calendar commitments
  11. Common sense climate interventions aren’t being funded at scale
  12. US row-crop farmers are only getting older
  13. Leveraging one’s network for fun and profit
  14. Companies engaging with their customers only in superficial manner
  15. People are uncomfortable saying ‘No’
  16. Leveraging others networks for fun and profit
  17. People are uncomfortable stopping a project they think should be stopped
  18. Making friends, especially as adults
  19. Healthcare not a basic right in the US
  20. Sharing organizational knowledge/history in companies
  21. Remembering and passing down family stories
  22. Job boards are incentivized to take ad dollars, not find candidates
  23. Creating and maintaining IT workflows
  24. Uncritical assessments of news media and social media posts
  25. B2B order tracking at scale
  26. Landfills are filled with stuff that shouldn’t be there
  27. Properly disposing of unwanted stuff, whether yours or a deceased loved one’s.
  28. Communication amongst a group of 50 neighbors
  29. Diets don’t satisfyingly answer what happens when success has been reached
  30. What should we have for dinner? for lunch?
  31. Finding higher-quality products on
  32. Getting tighter feedback loops (and therefore faster improvement) in homebrewing
  33. Email client UIs (e.g. Gmail) not supporting the today’s workflows.