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  1. Maybe you’re one away.

    Before you decide you’re bad at something, make sure you change the conditions.

  2. Give yourself a raise.

    Making more money is great.

  3. What if it works?

    Six rules I use to evaluate growth, protect my time, and decide when to leave money on the table.

  4. Before you make the deal.

    Dolly Parton turned down Elvis Presley to protect the publishing rights to her song.

  5. Your second choosing.

    The biggest decisions of your life are often made before you know yourself.

  6. People deserve bad news.

    Avoiding a hard conversation can feel harmless in the moment.

  7. It made every part of my life better, until suddenly it didn't.

  8. The world will keep moving along, in all its lunacy, whether you watch or not.

  9. Ask for what you want.

    There's something you want.

  10. Mediocrity at scale.

    There's a brand new way to fail, and it's spreading fast.

  11. The machine is a mirror.

    AI promises to free up your time, but history tells us otherwise.

  12. AI can now replicate content, systems, and funnels in an afternoon.

  13. Stop sharpening your axe.

    Why the most skilled person doesn't always win, and what actually moves the needle when you're building a business from scratch.

  14. Manufactured certainty

    You've been brainwashed to argue about the wrong thing.

  15. Rich and broke.

    The difference between looking rich and being secure isn’t what you make.

  16. The two-speed problem.

    Criticism shows up fast.

  17. Unreasonable.

    Why choices that look wrong build lives that feel right.

  18. Your new rabbit hole.

    The hardest move in learning anything new is the first one.

  19. Small enough to see.

    When life gets wider, paying attention to the most important people gets harder.

  20. Why the advice that works for them doesn’t work for you.

  21. Freedom. Sort of.

    What if the freedom you quit your job for isn’t really freedom?

  22. Sweat the small stuff.

    The self-help industry sold us a cure for a disease we don't have.

  23. Selective editing.

    The stories we make up about our heroes (and why we shouldn’t…)

  24. Synthetic purpose.

    When problem-solvers run out of problems, they manufacture fake ones.

  25. The machine or the life.

    Some mornings I wake up and think, what the hell did I just do?

  26. Pick a table.

    Two people joined the same company the same year with the same pay cut.

  27. Most people communicate what's in their own head instead of what the other person needs to hear.

  28. Thief of Joy.

    When I was 27, a friend asked me point-blank how much money I made.

  29. My old boss texted me during the pandemic.

  30. I'm a crazy person.

    The most successful people I know don't have better habits.

  31. Bored to death.

    At some point I got really good at my job.

  32. Get out.

    We squeezed into two bar seats on Valentine's Day without a reservation.

  33. Rock bottom.

    She threw herself down a mountain at 70mph — the same mountain that nearly ended her career four years ago.

  34. He was only 25.

    The winemaker was only 25 when he took over one of California's best wineries.

  35. One person away.

    A sushi speakeasy that seats eight.

  36. Being a purple squirrel.

    Eleven years ago, I watched a sales guy tape together a paper pyramid in a WeWork.

  37. Small by design.

    A tiny Champagne bar in Healdsburg seats twelve people and there's always a line.

  38. Nobody's even trying.

    Everyone says the market is saturated.

  39. Every podcast host asks me 'What's next?'

  40. My wife looked up from her phone in disbelief.

  41. My boss told me to move to San Francisco in two weeks and fire the entire sales team.

  42. You've changed.

    A friend paused his newsletter and podcast after ten years.

  43. The case for anti-scale.

    A consultant at a mastermind was doing $1.3M a year and wanted to 'scale.'

  44. Back in 2018, I was burning out and had no idea how to get attention for a consulting business.

  45. We all remember insults.

    I found a two-and-a-half-year-old email from someone explaining in four paragraphs why I'm a terrible writer.

  46. We hosted a private dinner for sixteen strangers.

  47. I sat down to write the first launch email for my biggest course ever.

  48. My wife lost her wallet in a NYC cab.

  49. A woman we met in a Paris cafe seemed to have the perfect corporate job.

  50. My wife and I just got back from two weeks in Tokyo.