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Episode 17 · Mindset

Sorry, Not Sorry: Things We Don’t Apologize for Anymore

Oct 29, 2026 · 43 min · Season 1

Things we don't apologize for anymore: how we dress, how we spend our money and how we spend our time. Jose talks about taking his earrings out for years to fit in at work, and why he now walks on stage in a blazer and Jordans. Jason shares how he was told to wear khakis to look the part as a young pastor, and how he still feels like an imposter at a $300 steak dinner. We also get honest about “must be nice” comments and the guilt that comes with finally having some freedom as a business owner. If you've ever shrunk yourself to fit a room, this one's for you. Heads up: there's a lot of language in this one.

In this episode

Questions we get into

  • Should you change how you dress to fit in at work?
  • Why do I feel like an imposter even when I've earned it?
  • How do you handle “must be nice” comments?
  • Why does the goalpost keep moving after you hit a goal?
  • How do you stop feeling guilty about free time as a business owner?

Key takeaways

  1. Choosing how you show up is different from being told how to look.
  2. Feeling like an imposter doesn't mean you don't belong in the room.
  3. Hitting the goal won't quiet the voice if you keep moving the goalpost.
  4. You don't owe anyone an apology for how you spend money you earned.
  5. Taking the risk of owning a business is part of what you're paid for.

Chapters

  1. 0:00Things we don't apologize for anymore
  2. 1:49Taking my earrings out to fit in at work
  3. 3:03Blazer, slacks and Jordans
  4. 5:28Authenticity and Jason's khakis story
  5. 9:50Choosing a dress code vs. being told
  6. 12:54Imposter syndrome at a $300 dinner
  7. 16:18Apologizing to yourself
  8. 18:03The goalpost keeps moving
  9. 19:20500 orders and still not enough
  10. 21:36We don't apologize for how we spend money
  11. 22:22“Must be nice”
  12. 24:52Keeping your life private
  13. 26:43Guilt about free time as a business owner
  14. 28:57When an employee questioned the spending
  15. 30:41Feeling guilty while the team builds the tables
  16. 31:27Gym first, then the shop
  17. 34:05A business vs. a job you built for yourself
  18. 37:56Taking the risk means taking more
  19. 40:22What freedom actually costs
  20. 41:16Final takes
“My shoes do not dictate what I know. They do not remove my experience.”
— Jose · 3:50
Your turn

What did you used to apologize for that you don't anymore?

Tell us in the YouTube comments, or send your question in anonymously for a future episode.

Companion post
The Sorry Audit: What to Stop Apologizing For
Read it →
Related reading
The Five-Line Success Scorecard (Money Goes Last)
Read it →
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