Carl’s Top 6 Retirement Tips

1. Consider Retiring Earlier Than You Think You Should

I’ve interviewed over 90 guests on “I Used to be Somebody” and almost all say they wished they had ended their careers earlier. This includes me. However, it’s crucial to consider your financial situation before making such a decision.

Honestly, think about your Sunday nights or Monday mornings. Do you have the same enthusiasm to get to work that you used to have? My last 3 or 4 years of work, it felt more like a grind, but I ignored it. I wish I had listened to my “Monday gut” and I would have created an exit strategy earlier, taking into account my financial readiness.

2. Stop Calling It Retirement!

I hate that word. To me that means “You’re done, you have nothing else relevant to contribute to the world”, which is why I call the phase after your primary career (un)retirement. It’s a time of brand-new possibility and personal reinvention! It’s a time to explore new interests and fulfill new dreams.

3. Figure Out the Money Thing


Figuring out if you have enough money to stop working full-time is pretty important. I talked to my financial advisor 5 years in advance. Don’t be afraid to start figuring out your new life ahead of time. And although I know you’re super-smart and everything, hire a certified pro. Most financial planners offer an initial financial consultation for free

4. Think About Your Future

If you retire in your 60s and you’re in reasonable health, chances are you’re going to live for decades more. Give some deep thought in ADVANCE about what you want to do next. Most people spend more time planning a 10-day vacation than how they want to live for the next 20+ years.

5. Don’t Jump Off a Cliff

One of the worst things you can do is have this hard-driving career for 25++ years and then just stop one day into the retirement abyss, telling yourself you’ll be able to figure it all out when you have more time. DISASTER ALERT! It truly takes some serious commitment to figure out who you are outside of your career. But you’re worth it!

6. Try the Gentle Slope Idea

If you’re in the corporate world, consider discussing with management about transitioning into a part-time or consulting position. If you’re an entrepreneur, go ahead and start off-loading responsibilities to staff, or hire a consultant to figure out what part of your operation is more profitable and get rid of the part of the company that isn’t successful. Do more mentoring and less “working.”

I know my tips probably seem like added work when you’re contemplating retirement. It’s a big decision to end a career you’ve had for a long time. It might even feel kinda scary. But these tips are inspired by my discussions with over 90 successful people who have taken the time to do “(un)retirement” right!

Author Profile

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The Author: Carl Landau, Guest Author

Host of the popular podcast "I Used to be Somebody," inspiring 50-plus-year-olds to build their (Un)Retirement good life, including, of course, a little bit about the virtues of the game he loves—pickleball. He is co-author of the Amazon best-selling book "Pickleball for Dummies" and organizer of the I Used to be Somebody World Tours.