Twenty-five years. A real career. It was real work, it was awesome, it taught me a ton, and it introduced me to tons of cool people. Then this one big beautiful life opened up the next chapter, and I said yes.

Here are the ways I’d celebrate leaving a long career, then a few reflection prompts to close it out well.

Ways to celebrate

1. Book the celebration dinner, that night

In January 2024 I shut my laptop mid-meeting and called my boss. It was final, it was bold, and it was true. That same night Mason and I celebrated my career transition with a fancy date-night steak and wine dinner. It felt so good to get out of that mess and step toward time with Mason, time for me and whatever came next. When people ask how I pulled it off, the answer is “I just did it, maaaan,” after I planned and made sure it worked, of course. Don’t wait for a better time. Pick a place and toast to where you’re headed.

2. Celebrate the people you led

I’m most proud of all the super cool, talented, and dope-ass people I was fortunate enough to lead during my career. THEY were awesome. The corporate BS was not. Hope they feel the love always. Write down the people you’re proudest to have led or worked with. Then tell them. A text, a note, a coffee. Let them feel the love too.

3. Write a gratitude list, including the hard people

I’m grateful for the colleagues I loved, and also for the people I worked with who were not kind. They all played a role as secondary characters in the screenplay of my life. Write both lists.

4. Do a symbolic delete

One of my first acts of freedom was deleting LinkedIn and my ever-loving corporate profile. It was plainly just no longer who I was. Pick your version.

5. Notice what fades

The early-morning texts stop. The jargon goes too: two friends asked about my CTAs, and I had no idea what they meant. My gap year brain had officially unsubscribed from the business jargon newsletter. Write these down. They’re wins.

6. Celebrate body wins

Rest first, then the wins come: my first chin-up, a lifetime PR on front-rack weighted lunges with zero knee pain. Celebrate yours out loud.

7. Book your first “yes”

My first big booking was the CrossFit Level 1 in Nashville. We made it a vacay, and I passed. Put one thing on the calendar that’s purely for the new you.

8. One bit of practical housekeeping

If your employer asks you to stay on for a retention payment, have an employment attorney review it before you accept. I didn’t, and it wasn’t worth it. You’ll celebrate more freely without a bad deal hanging over you.

Reflection prompts for leaving a long career

Give yourself 10–20 minutes per prompt and write freely. Your answers will change, and that’s fine.

• What achievements are you most proud of, and how have they shaped the wisdom you carry now?
• What parts of your old success story no longer feel energizing? What are you ready to release with gratitude?
• Describe a time you felt truly alive and fulfilled. What made it so magnetic?
• Who are you without the title? (I was more worried about this than the money.)
• Write a short letter from your future self, 6–12 months ahead, thanking you for taking this pause.
• What single word or short phrase wants to guide this next season?

These come from my free Vision Prompts. If you want a starting point for what comes next, take the free Soul-Pull Assessment, and if you like writing it out, the $19 Intentional Pause Workbook has thirty days of pages.

Congratulations on choosing to live life. 🤎

Related: How to Plan a Career Break You Can Actually Afford and A Midlife Career Change Isn’t Quitting on Life