Career Advice / Career Planning and Goals

Career Planning, Goals, and Big Decisions

Your career will not go according to plan. You still need one.

Careers stall when decisions don’t happen. These articles are about direction: setting goals that mean something, keeping your options open, and making the call when the answer isn’t obvious.

The tool for thisCareer Game PlanTwelve questions. A 90-day plan written for you. Free. Open it

96 articles on career planning and goals

May 28, 2026

Watching Other People’s Lives is Ruining Yours

We have almost too much information now, and it is quietly eroding our ability to trust our own judgment. Most people already know what they need to do long before they do it, and endless research has just become a socially acceptable form of procrastination. Scott on why you have to stop staring at everyone else’s party from the sidewalk and walk into your own.

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May 24, 2026

Love of Chaos by Guest Writer Mo Ibrahim

Guest writer Mo Ibrahim on why the obsession with AI-proof and recession-proof careers is missing the point. Using Nassim Taleb's concept of antifragility, Mo argues some careers don't just survive chaos, they get stronger because of it. The future belongs less to the people trying to avoid uncertainty and more to those who learn to navigate it directly.

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June 4, 2026

The Problem Is They Can’t See What You’re Doing

Scott’s favorite Seinfeld episode is “The Pick,” where Jerry gets accused of something he never did and nobody cares about the truth because they already made up their minds. The same thing happens in your career. People only see fragments of your work and fill in the rest themselves. Scott on why visibility is not bragging, it is clarity, and why nobody can support a goal they do not know exists.

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May 23, 2026

The Most Honest Version Keeps Pulling Us in One Direction

A Medium told Scott yesterday to lean into what feels natural and stop fighting what's coming his way. He laughed, then she pointed out 25 clients isn't a side hustle, it's a business. Scott on three years of coaching, the people who've shown up since day one, and why the feeling of being stuck usually has less to do with talent and more to do with honesty.

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