A Startup Employee's Checklist for Tough Times

Startups are, by their nature, risky endeavours. As an early-stage employee, you’re often exposed to much of the same risk as the founders: namely, what happens when the money simply isn’t there to make that month’s payroll? There’s an enormous opportunity cost associated with sticking around once the runway runs out, but leaving too soon may be foolhardy.

When I faced the prospect of working through a “dry period” at a startup, I had trouble finding clarity and direction. Answering the following questions, and revisiting them periodically, was immensely helpful.

The Questions

  1. How long am I willing to work without pay?

  2. How long can I work without pay?

  3. What concessions do I need to make working without pay feasible?

  4. What lifestyle changes should I make to ease working without pay?

  5. To what degree can my employer extend its runway through cutting costs?

  6. How confident am I that my employer will raise additional funding?

  7. If my employer raises additional funding, how and when am I likely to be compensated for my working without pay?

  8. When is my apartment’s lease up for renewal?

  9. Under what terms can I extend my lease?

  10. Should I extend my lease, find a new place, or move to another city or region?

  11. What job prospects are readily available?

  12. What do I need to do in order to be ready to apply for them?

  13. When should I start applying for them?

  14. When should I start contacting people in my network in advance of applying?

Or, to put it another way: What is my personal runway, how far down it am I willing to go, and how likely is it to pay off in the end?