Kevin Gainey

Better Answers to Poor Questions is a Trap
Why asking a better question is critical to winning the game you choose
2 hrs ago • Kevin Gainey
We Judge Our Past Selves With Our Present Minds
And why everyone is doing the best they can with what they have
Sep 11 • Kevin Gainey
What 13 Years of Living With MS Has Taught Me
On September 4, 2013, my world changed.
Sep 4 • Kevin Gainey

August 2026

Complaining Hardens Problems: What to Do Instead
David Bayer said something that stuck with me: complaining hardens a problem.
Aug 28 • Kevin Gainey
The Minimum Effective Dose of Thinking
Overthinking stalls you. Decisions move you.
Aug 21 • Kevin Gainey
The Expectation Gap
Unspoken expectations are premeditated resentments
Aug 14 • Kevin Gainey
Embarrassment fades. Regret doesn’t.
When you think of going after a dream, what feelings come up?
Aug 7 • Kevin Gainey

July 2026

How To Know If You Actually Want It
(Or Just Like Saying You Do)
Jul 31 • Kevin Gainey
25 Years of Getting Ready
Do you truly feel your life is your own?
Jul 24 • Kevin Gainey
The Past Does Not Get a Vote
You are not your failed business.
Jul 17 • Kevin Gainey
What You Lose When You Win the Wrong Game
I had a great life, a fun title, and the weekend plans everyone approved of.
Jul 10 • Kevin Gainey
The Patience Assembly
You have been casting a future version of yourself for years.
Jul 3 • Kevin Gainey
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