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Win the Retirement Game: Take Control of Change and Move Beyond the Status Quo

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June 20, 2026 By ESI 3 Comments

A few years ago I started a series on a retirement book I enjoyed. The book is Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy and, as you might imagine from the subtitle, it discusses the nine things that work against retirement to try and throw it off track (and “steal your joy.”)

In that series I posted to articles: Win the Retirement Game, Introduction which introduced the book, then Win the Retirement Game, Fighting Boredom which talked about creating curiosity in your retirement life to defeat boredom. But that’s where the series stopped.

I can’t remember why I stopped the series. It could have been because I was busy, because we were just starting our efforts to find a house in North Carolina, because my back had started bothering me, because I had too many other posts filling up my schedule, or something else.

So I stopped…but I always thought I’d come back to the book. And guess what? That’s exactly what I’m doing today! I’m going to pick up where we left off with this book — starting in chapter 3 which talks about embracing change (instead of being overcome by it) and defeating the enemy of the status quo.

And to make this series extra fun, I’ll be giving away a copy of the book at the end of each post, so be sure to stay tuned and read to the end if you want a chance to win a copy.

With that said, let’s get started…

Loss of Work Impacts Ego

We begin today by looking at the ever-present idea that people lose status when they retire since their job was a major part of their lives. Who are they without their career? This is the biggest change of all for many.

Here’s how the book starts the conversation:

The loss of contact with former colleagues can be felt as a loss in social status. If the loss of social contact and status remain unaddressed, it can impair someone’s adjustment to retirement and, eventually, their well-being. The social consequences of retirement can be exacerbated in situations where factors beyond your control precipitate the decision to retire.

The loss of social connectivity hurts, and it can be harmful in the long term. Cultivating social support is a critical part of aging successfully. But departing the workplace can be a blow to your self-esteem. You’re going from being in the center of all the action to feeling invisible. But the good news is that after an initial hit, people’s self-esteem tends to increase in retirement over time. Another study of retirees found that finding new ways of mattering – making a difference to others – affects how well people adjust and how they feel emotionally in retirement.

A few things to say here:

  • A future chapter will talk more about social connections in retirement, so we’ll save that discussion for that chapter.
  • “Factors beyond your control precipitate the decision to retire.” In other words, retirement wasn’t on your terms. You had a health issue and had to retire, they downsized you out of a job, the company went bankrupt, etc. — you were forced into retirement by something esle — not by a decision you made yourself. I can see where this is a jolt for many, and it’s certainly often tougher than making the decision yourself to retire. But this chapter has some help, as you’ll see.
  • I don’t get the blow to self-esteem personally as my job was never THAT important to me. But I get it for others. If I was a doctor or a highly ranked officer in the military, I’d probably have some loss of self-esteem. If my job was my entire life (or much of it), I would probably have some loss of self-esteem. So I can understand it from those perspectives.
  • “But the good news is that after an initial hit, people’s self-esteem tends to increase in retirement over time.” You know why? Because retirement is GREAT! And you come to see that you didn’t lose much compared to the huge gain in FREEDOM you picked up! In fact, you start to feel sorry for those suckers who are still working. lol
  • “Another study of retirees found that finding new ways of mattering – making a difference to others – affects how well people adjust and how they feel emotionally in retirement.” Some great ways to do this: find a new job that you love, volunteer for a cause you believe in, or find another passion that can be done with and/or for others. Simply find something new that makes you want to get out of bed in the morning. It could be delivering meals to the elderly or playing pickleball — there are lots of options!!!

Status Quo

The book then moves from the issues presented from losing status when retiring to the issue of trying to keep things the same (as much as possible) in your life when you retire.

It goes on:

As humans, we prefer the current state and what’s familiar. The Status Quo Bias is trying to protect us from making any change that we would  perceive as a loss. But what people really fear is regret. We want to avoid decisions we may live to regret, so we overvalue what’s familiar. We default to staying in our comfort zone. We play it safe. Doing nothing is always an option, and the Status Quo Bias often makes it an appealing option we’re pulled toward.

Status Quo Bias deludes us into thinking there’s no reason to change it. Why risk it? Everything is good just the way it is. The pull of the status quo is powerful. But stepping out of your comfort zone to get involved in new activities can help you grow.

Retirement is often not the only change people are dealing with. If you’re retiring at any age, you’re also getting older, and aging brings changes you’ll need to adapt to. Some people view aging as being about inevitable decline. But it’s not that simple or that negative. Psychologist Paul Baltes characterized aging as part of a lifelong process of adapting, noting that every phase of life includes gains and losses. Some declines are a fact of life. But there’s a lot you can do to mitigate them, delay them, and age successfully. One strategy is compensation, in which you make up for what you can’t do as well anymore by using different ways to accomplish the same goal or task. You don’t want the status quo to keep you away from things that can generate gains for you and be left only with the decline side of the equation.

Some thoughts from me:

  • Well, retirement itself is a change from the status quo, right? But I think what they’re talking about here is trying to keep everything else (activities, etc.) in your life the same just to maintain your sanity (or so you think).
  • I can tell you from experience that you really don’t have a choice — retiring changes everything — so you better get with the program and make the best of it or you’re going to be one unhappy camper.
  • From the first minute of the first day, it all changes — what you do, where you go, when you eat, what your options are, who’s around you, and on and on and on. Your life that used to be on at least somewhat of a schedule (if not a rigid one) is now wide open…with no one guiding it but you. It’s a blank canvas, an empty page, a clean slate.
  • The good news is that it’s a blank canvas…and you can make anything of it you want. The bad news is that it’s a blank canvas…and if you lack initiative, plans, curiosity, and interests, this emptiness can swallow you up. This is why I highly recommend having a plan for what to do with your time before you get to retirement. Otherwise you might find yourself adrift at sea.

Because of this (potentially) vast emptiness, many try to hang onto the status quo. But that ship has sailed. If you try to hang onto it you will not have a great/happy retirement. And you most certainly will not win the retirement game.

Which the book gets to next with this:

How do I defeat the status quo bias? By taking control.

Researchers underscore the importance of a sense of control in transition periods, where the rhythm of daily life is upended and your emotional state is thrown off. Some people experience ripple effects and become passive and disengaged, which can spark a downward spiral. When you’re in a transition, it’s essential to regain a sense of control.

People who are retiring can gain control by moving away from the status quo and making small, positive changes to build new healthy habits. Starting small ratchets down the risk. You’ll be less likely to fear regret because you’re making a small investment. It’s easier to step out of your comfort zone that way.

I think small changes are ok, but what I personally prefer is more of a plan — that you develop before you retire — of what your retirement life will look like.

You consider and test out the activities you think you want to do in retirement BEFORE retirement. You make a plan for how you want to spend your time in retirement BEFORE retirement (at least in the general sense). Then when you get there, you aren’t in some sort of limbo land where you drift aimlessly.

The Power of Routine

The book next moves to these thoughts:

Structure is one of the losses people experience right away when they move away from full-time work. Work provided organization — now that’s up to you. The flexibility to do whatever you want can be a blessing or a curse.

We rely on our habits more than we realize. Around 40% of our behavior is habitual. Our brains love rules of thumb. It makes things automatic and conserves energy when we don’t need to think about things consciously. And that’s what habits do. Habits matter. Research shows a significant portion of our subjective well-being, or happiness, comes from our habits.

There is great benefit in establishing a routine in retirement. Not a rigid, every-second-is-planned schedule, but at least a framework that you can live your life by.

I personally like to have an anchor event in the morning…which for me is exercise.

This gives me a partial routine as well as lets me accomplish a basic goal early in the day. This is why exercise is set first thing for me.

Then the rest of the day can be flexible and develop however I want it — stay at home and work on posts or get everyone in the car and head for the outlet mall for some super shopping.

This gives me enough of a routine that my life has structure but not so much that I feel I am moving from one thing to another with no choice about what I’m doing (which is a lot of what work-life is.)

I had a great routine in Colorado and rode that thing for several years. I had a hard time setting one in The Villages, probably because my gym was a bit wonky on when I could reasonably work out (it varied by day — some days were so packed I had to workout in the afternoon) and because so much “new” was always going on in The Villages. I have developed a North Carolina routine like the Colorado one, though it has less pickleball (which was getting out of hand honestly).

Now I feel I have structure, balance, and flexibility in my routine and it’s pretty awesome.

Final Takeaways

The book ends this chapter with the following takeaways:

Learn to accept and embrace change. Adapting to change is a crucial life skill, and it’s vital in retirement. How well you adjust during the transition to retirement will significantly impact how satisfied you are in retirement.

Step out of your comfort zone. It’s the pathway to ongoing personal growth. But the pull of the status quo is powerful. Fearing making decisions, you may regret what holds you back and prevents you from taking actions to lead to gains and growth.

Starting small reduces how you may perceive the risk of making changes. Change takes time. New techniques, especially the tiny habits method, can kickstart your efforts and get you on track faster.

My thoughts:

  • I’m not big on change and retiring itself is a big enough change to deal with…then everything else in your world changes too. You have no choice but to change with it — or, I suppose, curl up in a ball and cry all day, but that doesn’t seem productive. This is why having a plan and tested ways to spend your time in retirement will help you — they are enjoyable, familiar activities which will buffer the effects of all the change and help you make a smoother transition.
  • On point two, retiring is getting you out of your comfort zone in and of itself (at least IMO.) Take what you want to do and create a basic structure to your time — then test out new things as you find them. You can try many things and see what sticks. For me, this attitude led me to trying pickleball, and you know how that turned out. 😉
  • I do like starting small and building from there. When we tried pickleball, we got a cheap set of paddles from Amazon and played with those. Once we saw we liked the sport, then we invested in better paddles, shoes, etc. that made the playing time even more fun and productive.

To wrap this all up, my thinking is that you must be open to new things just to retire. So in addition to that you don’t need to change the world on day one. There is an adjustment period, for sure. The first week was just so strange for me — because it was so unfamiliar. But then I found the joy that comes with retirement freedom and I was off to the races!

To ease the transition, have a basic schedule set up, then experiment with new things here and there as time and your feelings allow.

I’m still doing this to this day — 10 years into my retirement. I try out new things now and then and decide whether or not to add them to my list of activities. I also prune out things that aren’t bringing me as much joy.

If you keep this adding/deleting cycle up throughout your retirement, you’ll do just fine.

That’s it for today. Stay tuned as there’s much more from this book to share.

——————————————

As I said above, I’m giving away a copy of Win the Retirement Game on every post I do about the book. Here’s how to you can enter:

  • Leave a comment below telling me what you liked best about this post, what you think you can use, or something you learned from it. Basically just share anything meaningful related to the content above (note: “please enter me to win” and similar comments will not be considered out of pure weakness! At least put a bit of effort into it!) This should be fun!
  • Be sure to leave your email address when you leave the comment so I will know how to reach you if you win (the email address will not be visible to anyone other than me).
  • The winners will be selected by me at random a few days after this post goes live. I’ll announce who wins in my own comment.
  • I’ll email the winner, get their address, and send them a book from Amazon.

As with most giveaways, there are rules. Here they are.

Good luck!!!!

Filed Under: Books, Retirement

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Comments

  1. Bradford Deudne says

    June 20, 2026 at 4:47 am

    I enjoyed this post. Seems like i’ve experienced a lot of what you covered. some of my identity was tied up with my job, big adjustment getting used to my new “status”. 4 years in and still excited with retirement. Especially enjoying the “blank slate” and creating my schedule and new routines. It took a minute to adjust to the new relationship (or lack there of) with my former work peeps. Making an effort to get out of my comfort zone. Good Stuff!

    Reply
  2. Steveark says

    June 20, 2026 at 10:29 am

    I liked the thougts on work as an identity. I had that kind of job, but I also had outside identities as a volunteer, a marathoner, a tennis team player, a fisherman, a church member and was part of other tribes as well. But I was the plant manager/top exec of a billion dollar company in a small rural town. We were the largest employer in the entire county and paid the highest compensation for our employees. Its kind of like being Andy Griffith in Mayberry, everyone knows you and most everyone respects you. Its an ego trip, that feels good if also kind of impostery. I thought I’d miss all the affirmation, but oddly, I never did. Not even for a single day. I never really was that guy, the big boss. It never was who I was. I was trying to be fair and nice to my coworkers, not to be in charge. As far as schedules go, mine is erratic, especially when the fish are biting. I got up at 4:40AM yesterday and pulled the boat to a local lake where my buddy and I caught a bunch of big bass. Super fun, and something I could not have done on a weekday in my former life!

    Reply
  3. BSue says

    June 20, 2026 at 11:19 am

    This article will be forwarded to my hubby, a 72-year-old lawyer who worries about full retirement because he doesn’t have a lot of outside interests. He works part-time now due to health issues. I wish he could find some new interests and a retired friend or two to make full retirement less daunting. He enjoys the mental stimulation of his small law practice.

    Reply

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