Midlife Remix The Wake-Up Call Every High Achiever Gets in Midlife
Nov 24, 2025
Larry Olson, an award-winning creative director who has worked with Nike, Apple, Spike Lee, and Al Gore, recounts a midlife reinvention sparked by success that felt hollow. He talks about the Times Square turning point, a three-item post-it that refocused his life, moving from ego to purpose, meditation, grief, and rebuilding creativity and meaning.
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Times Square Success That Didn’t Feel Like Success
- Larry Olson had three career goals: a national campaign, a Times Square takeover, and a Gold Pencil award.
- He achieved all three within six weeks yet felt a sinking emptiness eating takeout alone in a New York hotel room.
Use A Post-It Compass To Redirect Your Career
- Do write down clear non-negotiables to create a personal compass when your career stalls.
- Larry put three items on a Post-it (mountain life, meaningful work, inspiring people) and within weeks an opportunity to work on climate change appeared.
From Ego To Service Changes Creative Energy
- Larry shifted from ego-driven work to service-driven creativity by listening to his intuition.
- He stopped trying to sell himself and instead showed up to solve problems, which changed the energy in meetings and improved connection.