6 Top Tips to Successfully (Un)Retire

When I first retired, I had a traditional view of what retirement was going to be like but over the years of both my own experience and talking with others, I have learned that it can actually be something else altogether. I have since embraced (un)retirement and here are 6 of the top tips that I now wish I knew before I took the leap;

1. Stop calling it retirement!  

I hate that R 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. 

2.. Retire 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. 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.  

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. Plus, you can go into most financial planners and get an initial financial evaluation for free.  

Bonus Must: Get your Estate Planning in order! 

4. Think about your future. 

If you retire in your 60's 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, maybe discuss with management  about working 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 have taken the time to do "(un)retirement right! 

About the Author

Carl Landau currently hosts the popular podcast I Used to be Somebody, inspiring 50-plus-year-olds how to build their (un)retirement good life, including, of course, a little bit about the virtues of the game he loves — pickleball. He has been an entrepreneur since the age of 26 and now in (un)Retirement is founder of Pickleball Media. He has started and sold three successful media companies, published five magazines (software development, winemaking and craft brewing industries). Carl is also the co-author of the Amazon best-seller  Pickleball for dummies.