The View From Unretirement: These are the forces trying to ‘steal your joy’ in retirement

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Many people pondering retirement focus primarily — sometimes exclusively — on the financial part, to avoid outliving their money. But in Joe Casey’s new book, “Win the Retirement Game,” the Princeton, N.J., retirement and executive coach and Retirement Wisdom podcast host writes that nine other forces may be “trying to steal your joy.”

In my recent interview with Casey, the former Merrill Lynch HR exec shared his advice for combating some of these forces: boredom, the status quo, loneliness, inertia, expectations, uncertainty, complacency, obligations and drift.

Thrown for a loop

“Some people are prepared to adjust and pivot. Others are not,” Casey told me. Retirement, he noted “can be a big opportunity, but it can also be something that throws people for a loop.”

“Win the Retirement Game” is a parable about a composite character in his mid-50s named Pete learning how to face each potential retirement obstacle. Along the way, readers get smart advice from Casey — a 2021 Encore Network Champion — for plotting their own retirements to make them fulfilling.

Casey, it turns out, is a big fan of what he calls a “multipurpose retirement,” combining part-time work, learning new skills and finding meaning and purpose. Some call this “semiretirement.” I call my new life stage “unretirement.”

Here are highlights from my conversation with Casey:

Richard Eisenberg: There are so many other books about retirement. What makes yours different?

Joe Casey: I think it’s different because it’s based on my experience coaching people in creating their next chapters over the last 7½ years.

I wanted to give people an inside look into what things people come up against and how they navigate through them so they can anticipate them and be better prepared.

Read: ‘You don’t want to die at your desk sending an email.’ Beyond the numbers, are you ready to retire?

The book’s title talks about ‘the retirement game.’ Why do you call it a game?

I think it’s a game because there are challenges, and you need a strategy. I view it as a game in a positive sense. It’s something you can win at, and you can defeat these obstacles.

What do you consider a win in retirement?

I think that is defined by each person. But I think it comes down to what are the things that people find most satisfying in terms of how they invest their time.

Often, it’s family and other social relationships. For many people, it’s giving back to others. For some, it’s getting back to really good health. A lot of my clients wanted to get in the best shape of their lives.

The book goes through nine obstacles and how to deal with, or combat, them. I think hearing that there are nine might sound scary to people.

I took a look at all the clients that I’ve worked with, and no one dealt with all nine. There were usually two or three that were significant.

One of the points of the book is to be aware of the nine, because you can’t always predict exactly which one’s going to be a big one for you.

Read: People who do this one thing every day have HALF the dementia risk than the rest of us

Are certain types of people more likely to encounter one or more of these nine forces than others and struggle with them?

I hate to generalize, but I see more women struggling with obligations than men. And they feel like that limits their time. But you can renegotiate them. You can reprioritize them.

Are any of the nine forces especially pernicious?

One is boredom. Boredom can really lead you down a path of atrophy. Some people have had a dynamic, interesting career and then, all of a sudden, it’s not there unless they’ve navigated a gradual retirement. And they can get stuck.

The other is retirement expectations. Take a look at ‘What are my expectations and how can I not let other people’s expectations present too heavily in what I’m deciding to do?’ Stop judging yourself by others.

One of the forces you talk about is the ‘disorientation of overwhelm.’ What do you mean by that?

I think I’m in one of those periods. The disorientation of overwhelm can distract you from focusing time on what is truly most important to you. Are you doing the things you want to do? What adjustments do you need to make, as opposed to just doing, doing, doing?

Part of the planning, you write, is thinking about ways you’ll find meaning and purpose in retirement. You say that can be the final challenge. How hard is it?

When I first started doing this work, people knew they needed to find a new purpose, but they got stuck because that sounds daunting. They got frustrated and paralyzed.

What did you tell them?

Experiment with a creative vision of the things you really like to do. How do you want to invest your time? Then, come up with some ideas. You can have a portfolio of things you try, and purpose may emerge from this.

I have people design three alternative visions of the future for the next five years. Think swim lanes: your personal life and some version of work, maybe.

After the first one, develop the second five-year view that’s totally different. And then the third one — the wild card plan; if there were no restrictions, what would you really want to do? It’s kind of the run-away-and-join-the-circus plan to expand your thinking.

Then what?

Go and talk to people. If you want to teach, talk to people who have done that. If you want to run a marathon, talk to runners. If you want to start a business, talk to entrepreneurs.

You’ll learn a lot. Sometimes, you learn that it isn’t really cut out for you.

The other thing that happens: It develops new connections. Sometimes, it’ll turn into ‘Well, have you ever thought about doing that here? We could use someone like you on a part-time basis.’

What are a few ways people go wrong preparing for retirement?

There’s all-or-nothing thinking. Sometimes, people think ‘I’m going to retire and not work at all after working full time.’ And they’ve missed this semi- retirement option.

And people can sometimes forget we don’t stop growing once we retire. There are a lot of opportunities to keep stepping out of that comfort zone, but you have to do it yourself.

Your book suggests trying new things in retirement and if you’re not good at one or don’t think you’re going to get good or don’t like it, that’s OK. You can just move on without feeling like you failed, right?

Yes. You can try something just for fun and there’s probably a learning experience in there.

You also write about setting goals for retirement. Can you talk a little bit about that?

People coming off a long work life are used to having goals. All of a sudden, you go to retirement — you’ve probably seen the statistics of how much television and screen time people watch when they retire. It’s amazing.

Without goals, you can really drift. I think it helps to set goals around things you love to do, or something you want to learn. They don’t need to be mega- goals; just a framework that gives you some direction.

One challenge I’ve had in unretirement is deciding when it’s OK to say ‘no’ to things people ask you to do.

Saying ‘no’ is very hard for many people, but it’s like a muscle. Once people say ‘no’ to things, they discover it’s liberating. The world doesn’t end. The sun comes up the next day.

In his book, ‘The 7 Habits of Highly Effective People,’ Stephen Covey made the point that if we don’t say ‘no’ to things of lesser importance, we can’t say ‘yes’ to the really important things.

Some people struggle with a loss of identity in retirement. One way some deal with it is doing the type of work they used to do, but part-time. Or starting a part-time business. Are those good ways to deal with identity issues?

I am a big fan of redeploying your skills in retirement or keeping doing what you’ve been doing in a different way, because it keeps you engaged and contributing. A lot of times people don’t think that it’s possible. It does take some work and planning.

One challenge a lot of people have is determining the right time to retire. What’s your advice?

It starts with the financial side and getting an independent assessment of: Can you retire? What’s the chance you will outlive your money?

Then: What would you regret more — staying too long at the fair or the opposite?

I also think it’s how you feel about your job. Is it time to put your energy into something else? What’s really calling you now?

What would you tell people with spouses or partners about preparing for retirement?

Talk about these things early and often; most people don’t. What are each of your dreams? What do you each want in retirement? What are your concerns?

And I always give this advice more to my male clients than my women clients: Show up in listening mode and be curious about the other person’s perspective.

You’ve mentioned the importance of talking with a financial adviser to prepare for retirement. But are there other types of people to talk to?

You want to have your own board of advisers. For some people, the spiritual dimensions of retirement are really important, so they want to have some connectivity there. A psychologist or counselor or therapist would be another part. For fitness, you might have a personal trainer.

And then, mentors who can give you life advice.

Any final words?

Don’t go into retirement without giving it reflection and thought. And then make the most of it. It’s your time; you’ve earned it.

Learn how to shake up your financial routine at the Best New Ideas in Money Festival on Sept. 21 and Sept. 22 in New York. Join Carrie Schwab, president of the Charles Schwab Foundation.

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