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By By Alex Randall Kittredge

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Category: Entrepreneurship

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Episodes: 12

Description

Career strategy for the post-AI economy from a Columbia and Cambridge educated entrepreneur. Written for operators, fractional execs, and anyone who's stopped waiting for permission. One essay a week: careers aren't ladders, they're portfolios.

alexrandallkittredge.substack.com

Episode Date
Getting Laid Off Might Be the Best Thing That Happens to You in 2026
Mar 06, 2026
AI Is Coming for Your Job. Your Coworkers Are Already Building the Exit.
Mar 05, 2026
Why High Performers Stay Stuck in Careers They've Already Outgrown
Mar 05, 2026
Why the Fractional Executive Is the New Safety Net for Corporate Refugees
Feb 27, 2026
“If You Can Build a Business in Italy, You Can Build One Anywhere”
Feb 25, 2026
From Great Resignation to Layoff Job-pocalypse
Feb 13, 2026
Layoffs, AI, and the “new” career moat — Why You Should Be Building a Portfolio Career in 2026
Dec 12, 2025
How to Save $10.5 Million (At Work)
Nov 17, 2025
The Last Immigrant in My Family — and the Work Ledger He Kept
Sep 03, 2025
Captain’s Log: Sailing as Leadership Development
Jul 08, 2025
After the Term Sheet: Why Every Great VC Needs a Cynic in the Room
Jul 05, 2025
Pride and (Professional) Prejudice
Jun 21, 2025