The Hardest Boss to Fire Is You (with Diana Alt) episode artwork

EPISODE · Jul 17, 2026 · 45 MIN

The Hardest Boss to Fire Is You (with Diana Alt)

from The Corporate Escapee: Sometimes You Gotta Say WTF

"Work should feel good. Not a long, slow march to oblivion." That's Diana Alt, and it's the perfect line to open our first guest episode under The Time Rich Project. Diana is an executive and career coach who came out of tech. She works with people who are still in corporate and quietly wondering if this is it. Her take lines up with where this show is headed: corporate isn't the enemy. It's a client. You get to decide if the deal still works for you. We got into: The four cornerstones of an aligned career (right work, right boss, environment, culture) and how to spot which one is actually broken Why burnout comes more from misalignment than from long hours "The hardest boss to fire is you," and why building a business you hate is easier than you'd think Mission vs. money: don't burn down the thing paying the bills to chase the thing that lights you up Why anyone with 10+ years of experience should have an LLC in their back pocket The only two things you need to make your first dollar on your own: an offer and a way to get paid If corporate has stopped feeling good, this one gives you a way to figure out why, and what to do next. GUEST: DIANA ALT Executive and career coach helping people build work that aligns with who they are, in corporate or on their own. Host of the Work Should Feel Good podcast. * Podcast & site: https://workshouldfeelgood.com * Newsletter: https://dianaalt.com (click the "Let's Connect" button) * LinkedIn: Diana Alt, the No BS Coach: https://www.linkedin.com/in/dianakalt/  LINKS & RESOURCES Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes The Time Rich Collective (connect with Gen Xers on the same path) → https://trp-collective.circle.so/checkout/the-time-rich-project-collective  Website → https://timerichproject.life Mentioned in this episode: * Working Genius (Patrick Lencioni) — the six genius types * Time Rich by Steve Glaveski * Grace McCarrick — soft skills coach CHAPTERS / TIMESTAMPS 00:00 — First guest under the new name (and how we found each other) 01:15 — Fountains and drains: choosing who you spend your time on 02:10 — Who Diana is: work should feel good 04:05 — Your company isn't your boss, it's your only client 05:00 — The biggest flex in business: firing what isn't aligned 07:00 — The hardest boss to fire is you 07:30 — The four cornerstones of an aligned career 10:40 — Why burnout is about alignment, not just hours 16:00 — The 50-hour week and how little of it is real work 16:50 — Someone says "I'm done." Now what? Find what's actually broken 20:30 — Agency, victim mode, and the clients Diana won't take 23:00 — Good people who lost confidence in what they're great at 28:30 — Diana flips it: what to build for time freedom 29:00 — Owning your calendar, and the time-blocking experiment that failed 31:40 — The scorecard: relationships, health, purpose, fun 34:00 — Low-friction income and becoming a high-functioning lazy person 35:50 — The car-buying guy doing $300K a month 36:40 — Mission vs. money: don't burn down the day job 39:50 — Everyone should have an LLC in their back pocket 42:40 — You only need two things to start: an offer and a way to get paid 44:10 — Where to find Diana

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The Hardest Boss to Fire Is You (with Diana Alt)

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This episode was published on July 17, 2026.

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