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Outside the Box: 6 things to know before you jump into retirement

May 5, 2022

I’m six months into my retirement from the corporate world. How are things going? Any regrets? Any big surprises?

No regrets, for sure. I knew that leaving the workplace at age 61 would be a trade off of freedom gained versus money forgone. But I had a second-act dream to pursue—becoming an author—and, for me, that trade off was worth going for. So far, it has been. I have my first book out and another in the works. While I’m not making much money, having the freedom to pursue my passions without having to ask permission from anyone is, to quote a notable credit card commercial, priceless.

But there definitely have been some rough moments along the way. If you’re thinking about retirement, here are six considerations to keep in mind before you jump:

1. You have to create an entirely new identity for yourself. For 30 or 40 years, you had an identity conferred on you by an organization and by the working world in general. You could see that identity on your email signature, your business card, your LinkedIn profile. That identity came with fancy titles that brought certain privileges and power.

All of that’s gone now. It was all part of a game and the game is over. Outside the organization, you’re just a person, like anybody else. Who am I now that I’m no longer vice president of global public relations for a Fortune 250 company? I’m just a writer, an unknown one. I’m starting over.

Even for someone like me who never put much truck in titles, the void is startling and I’m still getting used to it. What I’m finding is that we’re never really as important as we think we are when we’re working, and that we’re more important in other ways than we ever realized. Those new aspects of identity, however, need to be discovered. Which brings me to my second realization.

2. You need to find a new purpose for your life. We humans need purpose in our lives, and work provides that. We don’t just work to make money. We work to make meaning for our lives and our time here on earth. You may not love your job—most people don’t, according to surveys. Still, that job gets you out of bed in the morning, which is a good thing.

Now that you’re no longer working a job, what’s that purpose that gets you up and (hopefully) raring to go? It can’t be about closing deals and making money any longer, so what’s it going to be? Giving back to the world? A new creative hobby? Helping your kids?

I consider myself fortunate that I’ve always had a powerful sense of purpose in my passion for storytelling. From the time I was a kid, I always felt my calling was to be a writer, and that never left me. Because of that, I never felt a strong connection to my identity in the corporate world, and finding a new purpose in retirement hasn’t been particularly hard. If anything, it’s been a huge relief, since all through my working years I felt like I was trying to serve two masters. Now, there’s only one, and happily it’s the master that gives me the greatest satisfaction.

3. Ramping down your spending is tougher than you think. I spent years preparing for an early exit from the grind. I built a nest egg, downsized, eliminated debt and slashed my monthly expenses to a fraction of what they’d been. The expectation was that the early years would be tight since I don’t plan to take Social Security early and I have to cover medical expenses until I can go on Medicare. I knew I’d have to budget carefully to make the plan work, but I’m pretty frugal to begin with, so I didn’t see a problem with that.

What I didn’t expect was how hard it would be to cut some of the frills out of the budget—like eating out. When I was bringing home a steady paycheck and wanted to go out to eat on Friday and maybe Saturday, too, I could do it without worry. Now that I’m living on my savings and I know those savings have to last me for the rest of my days, I need to weigh every expenditure, pondering what I will gain and what I’ll lose. Should I spend $70 on dinner and drinks, or save it for the property tax bill coming up next month?

To ease the transition, I’ve picked up a few writing and PR consulting projects on the side. Nothing too onerous—I don’t want to take away from my personal writing time—but enough to bring in some extra “frills” money. That’s helping a bunch.

4. You need to keep to a structured routine. I heard plenty of warnings about this before I retired, and they were all correct. Having a routine is critical in retirement.

Let me repeat: Having a routine is critical in retirement. It’s critical to both our physical and mental vitality. All the studies show that, without structure and routine, our cognitive capacities tend to decline faster as we age. I don’t want that, and so I’ve kept pretty much the same daily schedule I had when I was working.

I still get up early—usually around 5:30 a.m.—to get in a workout. From there, I make coffee, take Cassie for a walk, and come back inside and start my work. I usually write until 2 p.m. or so, and then I take a break and work on other projects, writing or otherwise. The difference now, of course, is that my routine is devoted to what I want to do, rather than what a big company wants me to do.

5. You need to give yourself permission to take it easy. This is the flip side of No. 4, and it’s been the hardest transition for me. When you’ve been working a high-pressure job for 30-some years, it’s hard to all the sudden take the foot off the gas and say, “Hey, it’s time to relax.” This is particularly the case for someone like me who has always invested a good deal of his identity in the notion of accomplishing things.

It’s OK to still want to accomplish things in retirement—things that are personally important to you. I certainly have a lot of things I want to accomplish in the years ahead. Still, if I’m not going to find time to smell the roses now, when am I going to do it?

So that’s what I’m working on: Giving myself permission to do nonwork—meaning non-writing—things that give me pleasure. I’m getting back into fly fishing and tying flies, which I didn’t have much time to do when I was working. I also plan to start golfing again, once I get this arthritic left hip replaced. Ugh.

6. You need to discover new ways to socialize. For me, the biggest loss I’ve experienced in retirement, more than the steady paycheck and the benefits, has been the camaraderie of the people I used to work with. I didn’t like spending hours of my day in fruitless meetings, of course. But I enjoyed being able to message people on the fly, work on projects together, have lunch or dinner while traveling—the things we take for granted while working.

All of that’s gone now. I’m still in contact with many of my former colleagues, but rarely do I talk to them during the workday. I’ve had to find other ways to connect with people and make friends. The gym is one of those places. I’ve already made a few new friends at the gym, all by just spending a few extra minutes there in the morning and taking the chance to speak to people. I’m also doing volunteer board work for a nonprofit and have met new people there as well.

No matter what age you are and how much planning you do, retirement likely will be a shock to the system, like jumping into a cold pool. I’m still adjusting to the water. But I sure am enjoying the swim.

This column first appeared on Humble Dollar. It was republished with permission. James Kerr led global communications, public relations and social media for a number of Fortune 500 technology firms before leaving the corporate world to pursue his passion for writing and storytelling. His debut book, “The Long Walk Home: How I Lost My Job as a Corporate Remora Fish and Rediscovered My Life’s Purpose,” was just published by Blydyn Square Books. Jim blogs at PeaceableMan.com. Follow him on Twitter @JamesBKerr and check out his previous articles. ​

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