How to Retire

I just read one of the best retirement books I’ve read in years. It’s one of the best I’ve ever read.

The book is How to Retire by Christine Benz.

As you’ll see over the coming posts, there’s a lot to like about this book.

Here are the highlights of why I liked it so much:

• The book covers so many major issues related to retiring well — especially the non-financial ones (which historically have been covered very little but are now gaining ground in newer books).
• Each topic is covered by an expert in that area — someone who has researched it, lived it, etc. I prefer ‘lived it” over “researched it”, but some of these folks research some pretty interesting stuff.
• The topics are covered one chapter at a time with Christine interviewing the subject matter expert. It’s enough to give you most of what’s important in considering a topic without boring you to death.
• The chapters are fairly short and self-contained, so it makes for really easy, quick reading. You can read a chapter here and there even if you don’t have much time for reading.
• Christine does an awesome summary at the end of each chapter which catches all the major points in less than one page. These are great takeaways that people can use to begin building their retirement to-do lists.

I recommend this book highly for anyone who is 1 to 40 years away from retirement. Hahaha. At some point I might rank the over 50 (maybe closer to 60 now) retirement books I’ve read, and if I do, this would be near the top.

In fact, I liked the book so much that I’ll be giving away several copies of the book (one every post about the book) throughout this series. See the end of every post to discover how you can win a copy.

The book is full of gold nuggets which I’ll be sharing with you over the course of several posts. After I share those thoughts, I’ll give you my two cents as well (of course!)

We begin with this short summary of what the book covers:

On your journey, the two dimensions you’ll constantly juggle are time and money. How can you best use the money you’ve accumulated and the time you have left?

I love that this book recognizes both the money side of retirement as well as the time/life side. Most books focus on the former while ignoring the latter. This book has a good mix of both.

Retirement Uncertainties

The book also understands that retirement is not static, and while it requires planning, it also necessitates the ability to roll with the punches that life throws your way:

Planning is crucial, but you’ll also find those plans are constantly revised. You might imagine life’s turmoil stops when you quit full-time work. But don’t fall prey to the end-of-history illusion, the misplaced notion that all change is behind you and that all will be calm in the years ahead. In truth, life’s upheaval both bad and good— will continue apace.

The bad upheaval includes everything from stock market crashes to health issues to family turmoil to cognitive decline. But what about the good upheaval? And how can upheaval be good? You might enter retirement confident that you know what you want to do with your time and money — but there’s a good chance you’ll quickly discover you’re dead wrong.

I’ve been retired many years and have seen positive and negative events hit both my life and finances. The positives:

• The successes of my various web businesses — ESI Money, Rockstar Finance, and the Millionaire Money Mentors
• Finding a new passion in pickleball
• Moving to a new part of the country with my family (North Carolina)
• The success of the stock market (and thus my index funds) and the selling of my rental properties
• Traveling with my family and having time free for significant life events
• Getting a cat

And some negatives:

• The passing of my mother
• Moving out of my (still beloved) Colorado to Florida
• Having back problems which slowed me down significantly
• Investing with a syndicator who was dishonest and others who were incompetent
• Covid

There are probably others I am forgetting but these serve as good examples.

None of these were expected when I retired and thus none could be planned for. I had to adjust to each along the way.

The book goes on:

View retirement not as a done deal, but as a long period of trial and error — which, let’s face it, is what your life has been up until now. Test drive the retirement life you want, trying out the activities you think you’ll enjoy and spending many months in the place you might move to.

See if you can take a phased approach to retirement, rather than quitting work cold turkey.

And don’t imagine the life you want at 62 will be the life you want at 72, or 82, or 92. As with your life up until now, you’re going to be making it up as you go and that’s a big part of the fun.

I’m not sure it’s “fun” — I know some of it is most certainly not fun — but it does keep things interesting.

The book’s point is true though: my retirement at 52 was completely different than what it will be at 62 (which is fast approaching). Who knows where I’ll be at 72 — I’m sure it will be a place none of us can predict now.

All the above was just from the book’s foreword. If we get that much from the first few pages, just imagine what there is in the rest of the book!

Now let’s dig in…

Not One Big Vacation

Chapter 1 of the book is an interview with Michael Finke, who studies “what activities and habits contribute to in-retirement satisfaction and joy.”

His work reminds me of Wes Moss and Wes’s book on what the happiest retirees know.

One thing Michael states right off the bat is that retirement is life, it’s not a decades-long vacation.

Here’s how he addresses the issue:

The weekend, or a vacation, is a relief from life in the workplace. It is doing something different. It’s relaxing. But you’re relaxing from something. And when you’re relaxing all the time, when you have a complete lack of structure, what is it that’s actually providing you joy?

Financial services companies are great at giving you images to help you imagine why you’re saving so much money. One of my favorites is the couple who’s sitting on a beach. Every financial services company feels like they need to take a picture of a couple sitting in beach chairs and looking out over the ocean.

And have you done that? I’ve done that before. I’ve sat by the ocean and just looked, and I can last maybe an hour. Maybe I’ll read a book. But by the time I get to the end of the week, I’m done. I’m ready to do something different.

And when it’s just a vacation, it’s glorious to be on a beach where it’s warm, and to be doing something different than the regular grind. You appreciate the change in your routine. But when the leisure activity becomes the routine, is it really going to provide the same amount of satisfaction as it used to when it was the thing that you did when you were on vacation, or the thing that you did on the weekends?

Let me say that before I retired I would have thought these comments were rubbish.

I remember a couple decades back when a friend of mine said he was never going to quit working (he worked at a non-profit and had a strong connection to its calling).

I told him I couldn’t wait to retire.

He asked me what I’d do with all that time.

I said I’d simply enjoy life…it would be like a permanent vacation.

He said he thought I’d get tired of that pretty quickly. I assured him I wouldn’t.

He was sort of right.

I have enjoyed retirement and it’s one of the best money moves I’ve ever made. But it’s been that way because (for the most part) it hasn’t been like a permanent vacation…it’s more like just plain life, but a life where I could dictate what I’d be doing, not having an employer do most of that.

In fact, the two years that were very similar to a permanent vacation — the time we spent in The Villages — were my least favorite in retirement. It was just a surreal place in many ways and didn’t seem like “real life.” Now that we’re in North Carolina and back to living in a “normal” neighborhood, we’re back on track (and happier).

I joke with my wife that I won’t need a vacation for a decade or so as I’ve had ten years of vacations…they were just all rolled up into one two-year stint in The Villages. Hahahaha.

Good Habits are Part of a Successful Retirement

Michael goes on to discuss the importance of creating habits and routines in retirement as they are the building blocks of happiness.

His thoughts:

So should your goals be episodic, or should they be more about habits? To me the most constructive goals are about establishing habits. If achieving goals becomes episodic, then it can be a letdown, and there may also be a moment of, “So what?” after it has happened. “Now I’ve done it. Now what do I do?”

We tend to be terrible at imagining what’s going to actually make us happy. Oftentimes it ends up being different than what we expect. And when we create our bucket list, usually earlier on in life, our estimation of wha’s going to give us fulfillment and satisfaction doesn’t necessarily align with our new reality of being a retired person.

So my perspective is that you should be very deliberate about your habits, create these grooves that you are going to follow for decades. And establish those grooves early on, so that you can develop productive habits that are not going to lead to a disappointing retirement. It seems like you probably want a combination. You want those healthy habits that you’re practicing every day punctuated with those joyful, exciting big plans.

This was a big part of why our move from Colorado to Florida was not a success for me.

In Colorado I had a routine based on several habits that made my life great.

I thought I would be able to replicate those in Florida, but the “always on vacation” lifestyle (an artificial lifestyle really) was not conducive to that (at least for me). As such, my happiness dropped like a rock when we lived there despite the place having many advantages.

BTW, it’s interesting to note that my wife had the complete opposite experience. She found the activities and social schedules built into The Villages lifestyle to be great assets that made setting her routines easier.

Which leads to a couple very important points:

• If you’re in a relationship, retirement involves you both, which each having an impact on the other’s retirement plans, activities, routines, and ultimately happiness. So you better get on the same page or someone is not going to be happy.
• Thankfully my wife and I are usually on the same page. But I know not all couples are — and I have seen one person retiring not going over well for one reason or another. So yes, get on the same page about retirement like you do on other things in your marriage.

As for the topic of moving, my advice is to be very careful before you leave a place you like a lot/love, even if you’ve checked out the new place thoroughly. Once you make the leap to move, it can be difficult to impossible to go back.

Working in Retirement

The Retirement Police are going to hate this next section. Hahaha.

The book’s conversation now shifts towards work and the impact it has on retirement (before and after you retire). Note that the author and the interviewee are both comfortable talking about working after retirement.

Michael begins his thinking here with these comments:

One idea that is ingrained in us socially is that we just step away from the workforce at a certain age. That’s what retirement means. In the future I hope that we will increasingly see retirement as the ability to control one’s own schedule. It doesn’t necessarily mean that we stop working forever.

Golfing is a good metaphor for this. During the working week we have so many intellectual challenges that it feels good to be able to get away from all that and just relax. So maybe we go golfing on the weekend. You have a very simple objective, you’re out in nature, you’re walking around. But when you get to play golf every single day, then, all of a sudden, golf is like work. You might want to get back to that challenging environment that you used to have. Having that variety can actually make us happier.

Several thoughts here:

• As we’ve discussed, the definition of retirement is moving from the old-school thought that you never work in retirement (it’s actually impossible to since retirement means “no work”) to an updated definition where retirement simply means you’ve left your decades-long career and can now do whatever you want…which includes work if you so wish.
• We’ve discussed how work or work-like activities is one of the top retirement activities every retiree should consider. The benefits that work and volunteering provide are critical to having a great retirement for a large part of the population.
• The golf discussion is a great example of how too much vacation can become boring (as we discussed above). That’s one thing that got to me about The Villages — there was just “too much” vacation —- you couldn’t get away from it…even if you tried. And thus it got repetitive. It also was never “settled” as “always on vacation” equated to “always on the go.” I just needed a nice, normal, relaxing day once in a while! Ha!

Why People Miss Work

Michael goes on discussing working in retirement with these comments:

Serotonin gets released by our body as a way of rewarding us for maintaining a higher social status, and we lose that when we leave the workforce. In fact, it’s as if we had a steady supply of a drug while we were working, and then we leave the workforce and no longer receive it. One of the things that people say is, “I used to have respect, but I’ve lost that. How do I regain that respect?” In some cases that can be difficult to do unless you’re doing the thing that you are an expert on. If your hobby is something like playing golf, where you don’t get that level of respect, then you’ve lost something. You’ve lost a part of your life.

I’m going to have to take his word for this.

I know that for many people a big part of who they are is what they do. And when they leave what they do, they struggle with who they are. I have talked to many who feel this way, so I know it’s a major issue that many must address. But it’s never been something that’s mattered to me.

My career, while fairly enjoyable, had one major primary objective: to provide for our family both while I worked as well as well after work time was over.

This is why I focused on managing my career to maximize my income (within reason of course, I still wanted to enjoy my work as well as make sure it was complementary to a good family life)…so I could earn a lot to save a lot to invest a lot to retire early. Then I could move on from doing what someone told me to do (in exchange for money) to doing what I wanted to do.

I was pretty successful at it as well. The vast majority of my career (all but seven years) was at the VP level or higher. But it was never who I was. It was a way to make a good amount of money so I could essentially buy my life back (from employers). That’s it.

Michael gets at this in his next set of comments:

Forty hours a week is a lot of time to be at a job, to essentially hand your freedom to do what you want with your time over to an employer. If you can get some of that back because you have achieved financial independence, while at the same time keeping the parts of that job that you really enjoyed, that seems a better strategy to me than just simply giving up every aspect of the job that you had before going cold turkey. It’s a big lifestyle change.

This is what I did.

I left my career and working for someone else to working for myself…with the hours, time flexibility, work tasks, etc. that I enjoyed (much more than my career).

Initially I didn’t think it would come to much, but a funny thing happened along the way (remember those unexpected things that pop up in retirement we mentioned at the start of this post?): my efforts took off.

I was probably successful because I enjoyed writing about money and finances, so I did a lot of it. Thus I had a lot of blog posts out there attracting new readers. Then I made a couple decent moves with Rockstar and the Millionaire Money Mentors and it transitioned from a fun hobby that I was doing for free to a fun hobby that generated a decent income.

The benefits from a non-monetary standpoint were that I had the fun and interesting challenges that come with work without all the crappy parts like commuting, company politics, terrible bosses and co-workers, and on and on. It was a win-win.

And it was a home run from a monetary standpoint as well, primarily because I earned enough that (so far) we haven’t had to live off any of our savings. This allowed our assets to keep compounding during a great time for the market, which is why our net worth is over twice as much now as when I retired.

Social Habits in Retirement

The last thing Michael discusses is the impact of social relationships on happiness in retirement.

His thoughts:

Living near our old friends can actually have a positive impact on how happy we are in retirement.

So can living in an environment that is conducive to more frequent social interaction.

I had a professor at Texas Tech who had done some research on this, and he found that people who lived in their own houses were happier throughout their lives up into their late 70s. Once they hit their 80s, people who live in apartments are actually happier than people who live in houses because they’re less at risk of becoming socially isolated.

The other thing we can think about is: How do we create habits where we maintain these opportunities for social engagement? Does that mean going to the gym on a regular basis? You’re probably doing that to maintain your health, but also for social interaction. Or volunteering.

I have lots of thoughts on these:

• This is probably one reason that the move to Florida was a bust for me — I left behind a lot of great friendships. None were really that life-changing by themselves, but I had so many relationships at so many different places (gym, pickleball courts, church, etc.) that they added up to something significant, even for an introvert like me.
• If you’ve lived somewhere for some time, you’re probably the same — you have a pretty substantial list of friends that you’ve developed over years or even decades. Replacing them will be harder than you think (believe me), which is another reason to really give it some serious thought before you decide to move.
• Once again we see how important having social relationships is on creating a happy retirement. This is why I put them into my list of must-consider activities for all retirees.
• He again mentions habits (routines). Is anyone seeing a pattern here? lol
• He has a great point about some activities doing double duty (or more) in contributing to a great retirement. For example, if you become a fitness instructor in retirement then that one activity alone can satisfy your need to work, to stay physically active, and to create social interactions!

As we wrap up chapter one, I want to include this little bit near the end of the chapter because it makes a vital point:

You’ve created an investment policy and an investment plan, but you also have to create a plan for figuring out what you’re actually going to do. You need to set yourself up in advance, so that you can establish those habits early on.

The vital parts:

• The best retirements are planned. If you play it by ear, you get play it by ear results (which usually aren’t good).
• You need to create your plan in advance. Don’t wait until you retire to create a retirement plan!
• One last mention of habits (routines). Hahaha.

The Summary

At the end of the chapter the author summarizes what she took away from the interview as follows:

Well before retirement begins, start thinking about some of the key things you want to achieve during your retirement years. They can be small but satisfying tasks, like finally giving the garage a good emptying out, or they can be bigger, such as writing a memoir.

If you like your job and are in a position to continue working in some capacity, approach your employer with the suggestion that you continue doing the parts of your job that you enjoy the most. In addition, l’d suggest you also compile a list of tasks that you want to stop doing because they sap your energy.

Plan to build structure into your days during retirement. Your schedule doesn’t need to be as rigid as it was when you were working, but having structured activities and tasks to accomplish will help you enjoy your downtime that much more.

Invest in relationships and your health just as you would invest in stocks: Start early and make ongoing investments.

If a lot of your social interactions come through work, aim to expand your social reach by volunteering, joining a meet-up group, or joining a club of people with similar interests. Don’t be shy about being the first to suggest a get-together when you meet new people who you click with.

These are mostly self-explanatory, but I do have somethings I’d like to add on:

• I recommend testing out the various parts of your retirement plan before you actually retire. Try new activities (keeping the ones you like), create outside-of-work friendships, consider developing a side hustle or volunteering, etc. Then you can fine-tune your plan with things you know will work, helping you to create a happy retirement.
• Employers these days seem much more open to workers scaling back on their jobs versus having to quit completely. I would have loved this option back in the day. I remember being in my early 40’s wondering if my employer would let me go to three days a week, but I was afraid to ask (because I knew the answer was no and it would put me into the “not a long-term player” group).
• You need at least some structured activities in your retirement to build your life around. Mine are currently my morning routine (puzzles and games), fitness (swimming and walking), afternoon fun or accomplishments (like household tasks), and evening entertainment/activities with my wife/family. These are pretty regular each day with the new stuff fit in around this (or part of the afternoon time).
• So many people focus on physical activities in retirement. If you’re not planning to do so, it’s a big mistake IMO.

These are some great topics, aren’t they? I told you it was an awesome book.

To read the next post in this series, check out Planning for Retirement.

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As I said above, I’m giving away a copy of How to Retire 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!!!!