How to Retire Happy, Wild, and Free, Part 2

I have already shared part 1 of my thoughts on the book How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won’t Get from Your Financial Advisor.

Today we continue with my review.

As I’ve been doing with book reviews lately, I’ll be sharing portions of the book and adding my commentary.

Here we go…

Retire Sooner Rather than Later

I get asked frequently what my thoughts are on retiring sooner rather than later.

I’ll get to that in a minute, but for now, here’s what the book says:

Regardless of how much wealth you acquire, you never know if you are going to live long enough to enjoy it. Eventually retiring at seventy-five with $10 million in the bank won’t do you much good if you die a month later. So, when is the ideal time to retire?

There is no ideal time to retire but you don’t want to put it off longer than you have to.

Several thoughts to share here:

  • I would NEVER counsel someone to prematurely retire. I prefer a solid retirement plan that includes strong financials with several margins of safety and at least a working plan of how the person will address the non-financial retirement issues talked about in this post and others. I am concerned that many early retirees (mostly younger ones) are cutting things a bit too close (at least financially) — too close for my comfort at least. Doing something like that would stress me out big time.
  • That said, I would recommend that once a person meets those criteria that he retire as soon as possible. Retirement is so AWESOME (if you have the above areas covered) and IMO should be enjoyed for as long as possible. Nothing is guaranteed and life has a way of crushing people indiscriminately. Why put the best years of your life at risk by waiting once you’ve won the game?
  • I say the above because waiting to retire was the biggest mistake I made in my FIRE journey. I really, really, really wish I had retired 5-10 years earlier than I did. And I could have since I was FI a decade before I retired.
  • That said, if you truly love and enjoy your work, then stick with it if that’s what you prefer. It’s your life, so make the best choices for you. But I know that’s not the case for most people and that’s why I’m giving the suggestions above.

Ok, go ahead and call me the ambassador of retirement — I just think it’s the coolest thing and want as many people as possible to experience it for as long as they can.

Could Retirement Last Longer than Work?

Here’s a quote that made me think.

The book was talking about how people are living longer these days when it made this comment:

This means that if they retire at fifty-five, there is a good chance that retirees will have three or more decades of life ahead of them.

Which got me to thinking, can l live long enough to be retired more than I worked?

My career lasted 28 years.

I retired at 52, so to be retired for 28 years I’d have to live to be 80.

I’m now 56 and according to a web search my life expectancy is almost 25 years, putting me at 81 when I pass.

So it will be close, but I could end up living in retirement more than I worked. Wow! That’s such a strange concept.

The old definition of retirement had our grandparents working until 65 and then watching TV and playing golf or bowling until they died a couple years later.

That’s about 45 years of work for two years of retirement.

And I might be looking at 28 years of each. It blows my mind…

Thirty Years is Worth Planning For

Combining the first point in part 1 (that we should plan for retirement) and the last point (we could spend a few decades retired), here’s a great group of thoughts:

Given that you may have thirty or more years of retirement life ahead of you, to not plan for an active retirement is to set yourself up for a difficult one. Failing to plan financially may result in you spending most of your retirement days thinking about all the fulfilling activities you aren’t able to pursue due to a lack of funds. Failing to plan emotionally may result in your working hard for many years, amassing a lot of money, and then wasting away your “golden years” in boring leisure activities.

Evens and Gail found that missing friends from work, being bored, and having trouble adjusting to change adversely affected these retirees more than a lack of money or poor health. Ideally, workers should start planning their retirement interests and activities several years before they actually retire.

It’s wise to start thinking about the personal side of a long time before you actually retire, particularly if you are a workaholic with few interests outside of work. “The more your life revolves around work, the more of a shock retirement will be.”

Thirty years.

Three decades.

A long, long time.

Don’t you think it’s worth five hours per year to plan for both the financial and non-financial parts of retirement?

Ok, I’ll give it a rest now…at least for a bit. 😉

But on the subject of work, I know the exact sort of person they are talking about — the one who works, then works, then works some more. His outside interests are zero because all he does (and maybe likes to do) is work.

So when this sort of person gives up the one thing in his life that means something to him, is it any surprise that things go poorly?

I would suggest someone like this begin developing outside interests five to ten years out from retirement. That gives them enough time to 1) wean themself a bit from work and 2) find out what they really like to do that could last for a long time.

Of course, if you ENJOY work, then by all means keep at it. But at some point, most people will be forced to stop working even if they’d prefer to keep doing so (health reasons often are the cause). So even the toughest workaholic is going to have to plan for a non-work life at some point — might as well be now.

What Interests You?

We’re going to shift gears now a bit.

For the rest of this post and the entirety of part 3 the subject matter will be on one topic: the importance of interests/activities in retirement.

I’ve beaten this dead horse for some time now, so we all know how important it is to have enjoyable retirement activities.

But the book shared several thoughts that expanded on what we’ve already discussed. Plus it’s an important enough topic to keep covering for new readers and those still dragging their feet in denial. 😉

So here goes…

You Need Several Interests

Let’s begin with the fact that you need several interests/activities to have a happy retirement. Here’s what the book says:

Breadth of interests is important. Retirement will feel empty if your interests aren’t varied. Just one interest, such as golfing, will not be enough to fill your days.

You Can Retire Sooner Than You Think gives even more detail.

In How to Have a Happy Retirement I noted this finding from their study:

The happy folks have at least 3.5 core pursuits — the activities and interests they love to do.

That’s not really that many (I’d round up to 4 versus going with 3). If you don’t have 4 non-work interests you can pursue in retirement, I’m declaring you in need of some “activities” coaching. Ha!

Don’t worry, the book has tons of suggestions for you. We’ll get to those in a minute.

But we haven’t previously seen the phrase “breadth of interests” used.

What does the book mean by “breadth” — the number of activities or the type of activities?

In the past we’ve talked about the number of activities and some qualifiers, but it appears they want the activities to be varied in type as well.

How exactly does this work?

For instance, let’s assume your four activities are as follows: golf, pickleball, tennis, and cycling.

These give you a breadth in numbers, so that’s good. But they are all physical, sporting activities, so are they varied enough in type? They are different sports so maybe they are.

It’s hard to tell what the book means as it doesn’t elaborate.

Anyway, it’s probably a moot point since most people who have 4+ activities have ones that are different enough to be considered a “breadth” of activities.

But there are some clear qualifiers for interests, so let’s get into those now…

Purpose and Achievement

The book puts a definite requirement on at least one of the interests you should develop:

It’s also important that you choose at least one major activity that provides some purpose and a sense of achievement.

I’ve heard both “purpose” and “a sense of achievement” used several times in multiple retirement books.

I look at it as you want to do something meaningful — whatever that means to you.

Volunteering is a great way to do this and we’ll talk about that in a minute.

But there are many other ways to do something meaningful — care for a loved one, research and document your family history, paint beautiful pictures, or a wide range of activities.

For me, I have a couple pursuits that give meaning to my life (other than my family which isn’t an activity):

  • I write and maintain this site. Over 1.7 million unique people have visited since I started writing (my previous site, started in April 2005 and which is no longer active, had over 10.9 million visitors and 24 million pageviews). I have to think that at least some of these readers have made decent financial progress in their lives based on what they’ve seen here. That gives me a lot of satisfaction, purpose, and a sense of achievement.
  • I volunteer at church, serving as a greeter. Being a greeter is not changing the world, but it can make a difference to some people. It may be the only friendly smile and warm greeting they’ve had all day (or week or month). So it makes a small bit of difference and it’s great knowing I’m part of a larger team focused on serving others.

BTW, I am still looking for a more “high level” volunteer opportunity as well but have been doing that for some time, so we’ll see if I ever find it.

How to Find Your Four Activities

The book suggests the following for how to find and develop your retirement activities:

A valuable exercise is to make a list of the ten favorite interests and activities that you would like to pursue in retirement.

At the same time, write down how much time you are presently spending on these activities.

Leisure consultants and pre-retirement planners state that if you are not spending any time pursuing these activities before retirement, it is unlikely that you will spend much time on these activities after you quit work. Retirees must choose activities that are right for them.

Ok, now they are asking you to develop a list of ten activities while before we only needed four. That could be a challenge for some people.

In the end you really only need four good ones, but my guess is that they want you to consider more because it takes ten tries to find four you like.

But it’s not that hard, really. For instance, working out can be one activity and is something everyone should be doing anyway. You should also have at least one thing to challenge your mind as well, so that’s two.

Add in a few fun activities and you’re easily past five and headed to ten.

As an example, here are ten that I not only could pursue in retirement but I do pursue:

  • Exercising (cardio and strength workouts)
  • Walking (around the neighborhood)
  • Pickleball (of course!)
  • Hiking (trails/woods)
  • Traveling
  • Family activities (get togethers, regular calls, etc.)
  • Blogging
  • Reading
  • Chess
  • Sudoku

Still having trouble thinking of ten? Well the book has you covered.

Check out part 3 of this series for some ideas.


Originally posted at

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