Episode 17 started with a simple question: what did we used to apologize for that we don’t anymore? For Jose, it was years of taking his earrings out before work so he’d fit the mold. For Jason, it was buying khakis he didn’t own because someone told him to look the part.

Neither of us was being ourselves, and both of us figured that out late. So here’s the tool we wish we’d had sooner: a quick audit of your apologies, and what to do with each kind.

My shoes do not dictate what I know. They do not remove my experience.

Step 1: Write down every sorry for a week

Keep a note on your phone. Every time you say sorry, or feel like you should, write down what it was for. Out loud, in a text, or only in your head. That last kind counts too. By day three you’ll see the same few show up again and again.

Step 2: Sort each one into a bucket

Every apology on your list goes into one of three buckets.

  1. You owe someone. You let someone down, broke a promise or hurt somebody. Keep these. Make them, and mean them. Jose said it plainly: he still owes a few people apologies and he’s working through them. Not apologizing for who you are is different from never apologizing.
  2. Someone else’s rule. How you dress, talk, where you’re from, the music you like. If you change it because you chose to, that’s fine. If you change it because you were told who to be, that’s the one to drop.
  3. The voice in your head. Nobody asked for an apology, but you feel like you owe one anyway. This is where imposter syndrome lives: sitting at a nice dinner wondering if you belong there, or feeling like everyone else would run your business better.

When you choose to be that, it’s different than when you’re told how to be.

Step 3: Do something different with each bucket

For someone else’s rule: ask one question. Is this a dress code I’m choosing to meet, or a version of me I’m being asked to hide? Jose still dresses up when the room calls for it. These days he walks on stage in a blazer, slacks and his Jordans, because the shoes don’t change what he knows.

For the voice in your head: write down what you’ve actually done. Not what you haven’t done yet. Jason has shipped over 500 orders of a product he started out of his garage, and he still caught himself thinking someone smarter would have done it better. The goalpost moves every time you reach it. A written list is harder to argue with than a feeling.

For someone you owe: make the apology. Short and specific. Then stop carrying it.

When someone says “must be nice”

You don’t owe an explanation for how you spend money you earned. Pick a line and let it go: “It is nice. It took a long time.” Or simply “Thanks.” Keeping your plans private until they’re done is fine too. You’re not hiding anything by not announcing it.

If you run a business: the free-time apology

This one hits owners hard. Your team is doing the hands-on work, and you’re at the gym at 9 a.m. It can feel like you owe them an explanation.

Jason used to apologize to his crew every time he’d be out for a morning. Then he listed out everything he actually does: purchasing, pricing, marketing, ordering material, the website, after-dinner admin nobody sees. The guilt didn’t survive the list. His job isn’t to build the tables. It’s to grow the business that pays for them.

Jose’s point: if the business can’t run a day without you, you built yourself a job, not a business. And the person who puts up the money, covers payroll, taxes and insurance, and carries the risk earns a bigger share when it works.

You don’t take the highest risk and then make the same as everyone else.

Your 15-minute audit

1. Read back your week of sorries. 2. Mark each one: owed, someone else’s rule, or the voice in your head. 3. Make the owed ones this week. 4. Pick one “someone else’s rule” and stop following it. 5. For the voice in your head, write five things you’ve actually done and read them before the next nice dinner.

Your turn

What did you used to apologize for that you don’t anymore? Or what are you still apologizing for that you know you shouldn’t be? Tell us. You might end up on a future episode.