How to Retire Happy, Wild, and Free, Part 1

The latest retirement book I’ve read is How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won’t Get from Your Financial Advisor.

The author is a free spirit to say the least, similar to Vicki Robin who wrote Your Money or Your Life, which makes the book a fun and entertaining read.

I’m probably the opposite of a free spirit (is there such a thing as an uptight spirit?), but I liked both of the books above (see The Best Personal Finance Books of All Time: Your Money or Your Life for my thoughts on that book.)

Looking at an issue like retirement from various perspectives is good IMO, so I read a variety of authors on the subject, even if I am uptight and they aren’t. 😉

I liked this book not only for its style but for what it had to say (of course). How to Retire Happy, Wild, and Free had excellent points throughout and thus I recommend it highly to anyone considering retiring in the next 5-10 years.

BTW, at some point I’m going to rank what I consider to be the top ten retirement books, but I have about 30 more to read first. Ha!

There’s no way I can share all the key points the made, so I’ve selected a few, will quote what the book has to say, and add my comments.

And I’ll need a few posts to get them all in.

Some of the thoughts will be suggestions we’ve heard before (though likely said in a new way) and are worth repeating.

Others are new to this book and worth adding to our stockpile of retirement knowledge.

In fact, I’m accumulating so much information on what makes for a happy retirement that I’ll probably change some questions to upcoming retirement interviews (BTW, if anyone wants to do one, shoot me an email).

With that said, here are some thoughts from the book How to Retire Happy, Wild, and Free

The Importance of Non-Financial Retirement Issues

The book isn’t even started yet (still in the preface) when it addresses an issue ESI Money readers are now considering pretty basic — but it’s one that much of the rest of the world ignores.

Yes, I’m talking about how the non-financial issues associated with retirement are as important as the money-related ones.

Here’s what the book has to say:

Although stockbrokers, bank officials, and other “retirement planners” overwhelm us with advertisements, solicitations, and advise on how to plan financially for retirement, they ignore other factors that contribute to a successful retirement.

Similarly, for every twenty books written on retirement, there may be only one that has any worthwhile treatment of the important personal issues.

The result is that many people spend forty years building an impressive retirement nest egg, but no time at all thinking about how they are going to enjoy retirement.

Indeed, the biggest mistake you can make with your retirement planning is to concentrate only on the financial aspects.

Some thoughts from me:

If I created a “how to have a great retirement” class/product, would anyone be interested in it? What would it be worth to you?

The Benefits of Retirement

The book lists “a few of the benefits you get to enjoy once you retire”.

Here are some of those that I want to comment on:

  • You can get up when you want to
  • You have no daily rush hour traffic to contend with
  • You don’t have to deal with the jerks at the office anymore
  • You can spend winter in Florida, Arizona, or Hawaii
  • You get to set your own agenda
  • You have fewer headaches because life is simpler
  • You don’t have to report to a boss about your actions
  • You can go on a vacation when you want to go and not when your employer says you can
  • By doing things when everyone else is at work, you can be much more efficient and less hurried at the same time
  • You can take a carefree vacation without having to take some work with you
  • You can feel morally superior to working people because you have earned your retirement and they haven’t

Here are my thoughts on these:

  • I love, love, love getting up when I want to. In the almost four years since I’ve been retired I have set my alarm fewer than ten times, and many of those have been to get up to catch a flight to somewhere awesome. Ha! When I first retired I was up at 5:30 am almost every day and hit the ground running. These days we go to bed later and get up later as well. But we have complete freedom and it is AWESOME!
  • The commute. Ugh. Who likes a long commute? Thankfully I never had a bad one (I had a friend in New York who used to commute two hours each way), but the time still adds up. 20 minutes each way is 40 minutes a day round trip, 200 minutes a week, and 10,000 minutes (literally 167 hours or almost 7 full 24-hour days) PER YEAR. That means over my 28-year career I spent at least 194 complete days (24 hours) commuting. That’s over half a year! And if you took it as the percentage of awake time it would look even worse. I tried to make the best of it (I listened to books on tape to redeem the time), but still I am very glad to be rid of a daily commute (and especially so when there’s bad weather).
  • Anyone ever work with people they didn’t like? Hahahaha! A better question is probably, “Have you ever worked anywhere where you liked everyone?” I actually have (one time, for nine years) but even then people get on your nerves from time to time. It’s much easier to distance from jerks in retirement.
  • We are really grappling with the snowbird thing. Colorado had a very long, cold winter this year (it snowed a lot starting in October — thankfully we were in Florida). The snow, cold, and overcast conditions held on for months — way longer than normal. I think the rough conditions have finally convinced my wife to move to Florida for 2-3 months each winter, but now we have to work out when and where.
  • Freedom is what makes retirement most awesome IMO and freedom to do what you want when you want is amazing.
  • Life is way simpler in retirement. It’s also way less hectic, both of which are very nice.
  • Anyone ever work for a boss they didn’t like? Hahahaha! I don’t think I need to comment further on this one…
  • We give ZERO consideration to work issues when we plan vacations these days (at least our work issues — if we go with someone else, they have issues to deal with). In the past, I always had to consider what was going on at work when I was determining vacation dates. In retail, we had a policy of no vacation time in November and December. That alone is enough to put a major crimp in your scheduling.
  • One of the biggest advantages of retirement is that you can go places when others are at work — the grocery store, the gym, the coffee shop, walk the neighborhood, the theater, vacation, and on and on. And since these are usually “off peak” times, you can often get discounts. 😉
  • Have you ever taken work home on vacation? I have, many times. Even if it was only checking my email and forwarding on important messages, doing anything work-related while on vacation is a huge pain. (I can still remember checking my email every day on our first cruise. Ugh!)
  • Hahaha! I must admit that when someone my age starts spouting financial advice, I ask myself “if he’s so great with money, why isn’t he retired yet?” Obviously it might simply be because he loves working. But I still get a wee bit of moral superiority in there. LOL!

The book summarizes the above with this awesome quote:

The best part about retirement is that it allows you to stop doing what someone tells you to do; instead, you can start doing what you want to do.

As I said earlier, it’s all about the freedom. 😉

For more thoughts on the advantages of retirement, see Ten Things I Didn’t Expect in Early Retirement and Top Retirement Don’ts.

Few Commitments

Here’s a quote I really identified with:

“But once you retire—and that’s one of the things, if not the thing, I enjoy more—there’s a minimum of binding commitments that I can’t rearrange or circumvent or get around. I enjoy that after so many years of being very rigidly involved and committed to a timetable that I can’t control.”

Most of my work life was built around a calendar and that calendar was chock full of meetings.

Especially at the end of my career where I was high up in the organization, I had many days where it was one meeting after another all day.

The best job I ever had (also the one where I liked everyone) had few meetings or even appointments (we were a small company), but the vast majority of my 28-year career was committed to one thing or another.

That’s why I loathe putting even one thing on my calendar in retirement.

Seriously, if I have an appointment in a day it really puts a damper on my retirement style.

So…I try to limit appointments.

Of course I can’t eliminate everything (trips to the doctor/dentist, car maintenance, etc.) but I can take out many of the non-essential get-togethers in life (like coffee invites from “friends” (aka casual acquaintances), activities at church, financial seminars (ha!), and the like.) Only stuff I really want to do makes the calendar these days.

Leave Nights Wide Open

Here’s a quote that goes well with the one above:

For the happiest life, days should be rigorously planned, nights left open to chance. — Mignon McLaughlin

Now for me, “rigorously planned” does not mean a scheduled event or appointment, but a general idea of what will happen in the early part of the day.

Most of our days currently either look like this:

  • Get up
  • Feed cat
  • Drink a glass of water
  • Check the web (my sites, a bit of news, sports, etc.)
  • Play/love the cat (depending on what mood he’s in)
  • Go for a long walk with wife
  • Eat and do Sudoku puzzle
  • Write a bit
  • Exercise
  • Write some more
  • Walk again
  • Eat dinner

Or this:

  • Get up
  • Feed cat
  • Drink a glass of water
  • Check the web (my sites, a bit of news, sports, etc.)
  • Play/love the cat (depending on what mood he’s in)
  • Walk to the pickleball courts and play for 2-4 hours
  • Eat when I get home
  • Write a bit
  • Exercise
  • Walk with my wife
  • Eat dinner

The day ends at dinner and is wide open for whatever — watching a movie, sitting and talking, reading, or whatever. Once I “knock off for the day”, which is usually about 4 pm, it’s all over. Nothing productive is planned or done.

BTW, those are my recent schedules. I used to exercise earlier but during the stay-at-home orders I altered much of life, liked the changes, and haven’t gone back.

That’s it for this time. If you want to read more about this book, check out part 2 of this series.


Originally posted at

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