Archive - 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

June 2026

The Decisions You're Avoiding

Most people who feel stuck are not actually stuck.

Jun 26 • Kevin Gainey

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