Could’ve, Would’ve, Should’ve

  • Should’ve. Well now, there’s a question to ponder. Over the course of a professional journey, the should-NOT-have’s have a way of presenting themselves pretty readily, but what about the should-haves?

A few answers come straight to mind. I should’ve:

  • Taken more risks. I never took a creative risk that didn’t pay off. (And after all, what’s to lose? You’re the boss. If you don’t deem a piece publishable, you can always send yourself back to your desk and make yourself do it again.)
  • Shared more first drafts. (More than that one time, I mean. Geez, Susan.)
  • Allowed myself to write more like Anne Lamott.
  • Trusted myself to write more first-person pieces, earlier in my career.
  • Read more David Foster Wallace. Read more fine contemporary essayists in general. Read more Shakespeare, more often. Ditto for poetry.
  • Started Fast Company myself.

Bigger questions demand serious thought, though. What articles should I have written? What stories should I have told? What could I do about that now?

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