Here’s our latest interview with a retiree as we seek to learn from those who have actually taken the retirement plunge.
If you’d like to be considered for an interview, drop me a note and we can chat about specifics.
This interview was conducted in September.
This guy is long-winded so we’re going to split his interview up into two parts. Hopefully he doesn’t bore you with part 1 and you come back for part two. 😉
My questions are in bold italics and “their” responses follow in black. Let’s see if you can guess who it is…
Let’s get started…
How old are you (and spouse if applicable, plus how long you’ve been married)?
I am 59 and my wife is slightly older.
We’ve been married for 32 years this fall.
Do you have kids/family (if so, how old are they)?
We have two children.
Our son is 27 and works in Colorado.
Our daughter is 25 and also works in Colorado.
Our son-in-law is 24 and also works/goes to college (GI Bill) in Colorado.
We see our daughter and son-in-law quite often as they make frequent trips to Florida.
What area of the country do you live in (and urban or rural)?
We live in The Villages, Florida.
In case you somehow missed it, here are several of my experiences in The Villages:
- Life in The Villages, Florida: Purchase, Arrival, and Getting Settled
- Life in The Villages, Florida: February 2023 Update
- Life in The Villages, Florida: March 2023 Update
- Life in The Villages, Florida: April 2023 Update
Is there anything else we should know about you?
I think I just spilled the beans on who I am…and if you’ve been reading this site for some time, you likely know all about me. Hahaha.
Before this site I had a blog called Free Money Finance that I started in 2005. I still pay the $150 a year to keep it as I don’t have the heart to see it go away. lol.
How do you define retirement?
I define retirement as leaving your established career.
For example, I worked almost 30 years as an executive in various businesses. It was a career that I built by initially getting a bachelor’s degree and then following that up with an MBA.
When I left that career, retiring from the last position where I used those skills in a business that someone else owned and where they directed me, that’s when I retired in my mind.
That said, I don’t think that retirement and work are mutually exclusive. Retirement has been undergoing a change in definition over the last decade or so. In fact more people now say that they expect to work at least some in retirement than people who say they will not work. Thus the definition of retirement now includes work for the majority of people.
What sort of work are they talking about? When you have the freedom to retire from your career, you can choose whatever work you want to do.
Some people work part-time jobs just to make a little money and to get out of the house.
Others start a business or bring one into retirement and run it as sort of a passion project or something that provides excitement and challenge to their lives (this describes me).
Others might buy a business that already exists and start working on it.
And even others might take lower-level positions in industries they always wanted to try out and think that they will enjoy.
Those who do not work, might pursue work-like activities such as volunteering. This could take many forms of course (from hands and feet on specific tasks to offering strategic guidance to non-profits). And because volunteering offers many of the non-financial benefits that working does, it’s a popular choice for retirees.
For me specifically, I have purchased a business (Rockstar Finance) as well as created a couple others while I’ve been in retirement. I’ll share more on those throughout this interview.
How long have you been retired?
As of this writing, I have been retired over 7 years.
Is your spouse also retired?
Based on the definition of retirement I gave above, my wife has been retired for over 25 years. That is when she left her career as an audiologist to homeschool our children.
Once they were educated, she did work at our church part time because she enjoyed it (she started as a volunteer and they had a policy change that required teachers to be “on staff” – so she joined the staff because she wanted to teach), but she hasn’t returned to her career since she originally left it.
So I guess she’s the one that should be doing this retirement interview instead of me – she has much more experience than I do! Hahaha.
What was your career and income before retirement?
I worked in business, and specifically in marketing, for many businesses throughout my career.
I got my undergraduate degree in Business Administration. I had gone to school to ultimately become a lawyer, but an internship I took changed the course of my life. You can read about how I transitioned from working in the law to being a marketing executive in How an Internship Saved me from the Law.
Once I made that transition, I knew I needed more education to get the type of job I wanted (and to make the sort of income I wanted). That’s when I applied to several schools to get an MBA and ultimately went to a Big Ten school for it. You know, back when the Big Ten had ten schools in it. LOL.
After that, I worked in several different businesses in many different industries, but all were within the realm of marketing except for a brief two-year stint I had as president of a company.
I marketed everything from dryer sheets to ketchup to frozen food to music to books to much more. In general the concepts were similar: find a market and tell consumers why they needed your product so they would buy it.
My first job out of graduate school in 1988 paid $40,000 a year. That doesn’t sound like much, but if you put it into the CPI inflation calculator it works out to over $100k in today’s dollars. (FYI, I passed earning an actual $100k about seven years into my career.)
In my highest earning career year, I made roughly $275,000. This does not count side hustle, dividend, real estate, or any other income.
To read about all the jobs I had throughout my career (and how they played out), checkout the My Jobs series.
Why did you retire?
I retired kind of by accident. You have to remember that at the point when I was considering retirement the FIRE movement was pretty much in its infancy. Or at least it wasn’t as big/widespread/practiced as it is today.
Yes, we had had Your Money or Your Life for many years, but the concepts within that book were not really adopted into mainstream personal finance thinking until a group of people lit the fire (literally) and started talking about how to become financially independent.
With that background, my plan had always been to retire early at 60. I didn’t know anyone who had retired that early, so I figured that I was way ahead of the curve if I retired then. Thankfully I didn’t wait that long as I would still be working today – yikes!!!!!
Then an unfortunate set of circumstances, or at least ones that appear to be unfortunate, presented themselves.
I’d been minding my own business, working for a company that I loved with people that I loved. I’d been there almost 10 years, when another company recruited me to become their president.
My wife and I thought about the opportunity long and hard, with many pros and cons associated with staying versus leaving. Ultimately we decided that the new job was for us. So we moved across the country, and I started my new position as president of a $100 million company.
Within the first full year of my presidency, I delivered the highest sales in company history and the fourth highest level of profitability. This was in an industry that was declining double digits because of competition from many different sources (but primarily from Amazon).
A little over four months after posting these achievements, I was rewarded by being fired. My boss, the owner of the company, had left the company to work on another family business. As a result, he turned over control of his company to another relative, who didn’t need or want a president. As such, I was let go.
To say it was a shock is an understatement. I had had a very successful career up to this point. I had left an amazing position and company to travel across the United States for this new job. So to be fired after delivering such great results just seemed unfair in so many ways.
At this point my net worth was a little bit over $3 million and given our lifestyle we had more than enough to retire. But there was one small snag: we lived in Oklahoma.
I’d never imagined myself retiring in Oklahoma, and after living there a couple years, that imagination was reinforced as something I didn’t want to happen. I know some people love the state, but it wasn’t for me.
So I started looking for a new job, and within a couple of months found one running marketing for a Colorado Springs-based company.
Once we got to Colorado, we found out how amazing it was there. And after a while the work became terrible. I had a micromanaging boss, who wanted to do things his exact way with no exceptions. This obviously was not what I had signed up for, and since we had now moved to an amazing area of the country, I felt like there was no better time to retire than now.
So I gave my notice, retired, and haven’t looked back one bit.
PREPARATION FOR RETIREMENT
When did you first start thinking seriously about retirement and when did that turn into a decision to do it?
It started a few months into the job in Colorado.
The work was not interesting, the company was in decline, and my boss was not great. I found myself yawning consistently throughout every day. I was bored, not challenged, and my heart was simply not in working for this company.
But that’s what I did, I worked, right? I still hadn’t gotten it. I had enough to retire at that point and for some reason it just didn’t click.
Then one day my boss asked me, “Isn’t this job the most important thing there is to you?”
Obviously, he expected me to say yes it was the most important thing, but I chuckled a bit and said, “No, it’s not even close to number one. It’s probably three or four on my list at best.”
This is not what he wanted to hear, and he didn’t take the response well. Hahaha.
It’s at this point that I knew my time was limited at the company – either he was going to fire me or I was going to leave. So I started making plans for my escape.
It didn’t take very long to know that I had enough to retire financially. And while I’ve learned a lot about retirement since then and how important it is to plan for the life side of retirement, I didn’t really have a plan for what to do with my time. I just kind of knew that I had enough interests and I was a curious enough person that it would work out.
I stayed long enough to celebrate my one year anniversary with the company as I felt I owed that to them for moving me to Colorado. I retired the month after that.
What were the major steps you took from deciding to retire to developing a plan to do so?
Well, some of you may be shocked to learn that I didn’t have much of a plan. I have learned a ton about retirement since retiring, but prior to retiring I didn’t know much about it (at least the reality of it.)
This is one reason I’m skeptical of “retirement experts” who are not retired. It’s one thing to know about retirement as a concept, but it’s a whole different thing to really know it by living it.
As I’ve written quite often on this site, to be successful at retirement you must have two areas covered. You need to have the financial side of retirement planned for as well as the life/time side prepared for.
I knew I had the financial side covered as I had both a decent level of assets (about $3.3 million) as well as some sources of income. Plus I knew I could always pick up some extra income if I had to. Plus I had other margins of safety as well. So the financial side was more than solid.
That was the extent of my financial planning for retirement. I did not run a million budget scenarios or project income and costs for the next 30 years. Over twenty-five years of solid money management allowed my to feel pretty secure with our financial set-up going into retirement. (I did create a retirement budget for the first three years just to make sure, but it simply reinforced what I “knew” in my heart – we had more than enough.)
However, as noted above, the life side was really not considered. I had always been a curious and involved person, so I just figured that I would have more than enough to do in retirement. But I didn’t sit down and think about what those things might be, how much I enjoyed them, the impact on my spouse of me retiring, or really much of anything else. This was a mistake and something I would correct if I had to do it all over again.
I did know that I would much prefer my freedom than work. And since I had the finances to be free, so why not go for it? If the worst case scenario happened and I hated it I could always go back to work.
That was the extent of my retirement plan. Obviously I don’t recommend this level of planning for anyone. In many ways my writing has been me as a guinea pig doing things that I think might work out financially. Many do and some don’t, but whether they do or don’t they still serve as examples for others to either emulate or avoid as they make decisions later on.
This one, the life side of retirement planning, serves as a “don’t,” even though things worked out fine for me.
What did your pre-retirement financials look like?
I had approximately $3.3 million in net worth when I retired.
About $600,000 (at cost) of that was in 14 rental units in Michigan. These delivered roughly $60,000 in income per year. With that income alone, I knew we could survive because we didn’t have a mortgage and we could keep costs low if need be.
I also knew that we could withdraw from some of our assets if we needed to. But about that time, this website started doing well and earning more. So the rental income, some dividends, and website earnings combined more than covered our living expenses.
What was your overall financial plan for retirement?
My overall financial plan was pretty much to stick with what’s described above.
I would keep the rental units and their income.
I would keep writing on this website because (first of all) I found it to be fun, interesting, and a mental challenge. But also it had the very nice side benefit of producing a decent income. LOL!
If income ever dropped below expenses, my plan was to start withdrawing from assets.
That’s about as “complicated” as my plan was.
Did you make any specific moves to prepare your finances for retirement?
I had made moves years in advance that had helped prepare me for financial independence as well as retirement (like buying real estate).
Those were in place when I wanted to retire so I didn’t need to make any specific moves at retirement. However, I did make several financial moves after I retired. See below for details.
BTW, if I had to do it all over again, I would have done a complete medical series (physical, dentist, eye check, etc.) before I retired (when I could still use my company insurance.) In the end it didn’t matter that much financially, but I think doing this is generally a wise pre-retirement step to take.
Who helped you develop this plan?
It was completely on my own. I did not have a financial planner or seek advice from anyone else. Of course I talked to my wife about retiring but the extent of her involvement was a simple, “Go for it!”
I had, of course, written and studied about personal finances for over two decades at the point I retired so I had a pretty solid knowledge of money and how it worked – probably better than most advisors have.
So why did I need help? Hahaha.
What plans did you make in advance to leave your job?
No plans really.
One day I simply said to myself, “I’ve had enough of this. I have enough money, so why am I doing something that I hate?”
The answer to that was there’s no good reason to do something that I hate, and that’s when I decided to retire. After talking to my wife, I went in the office and told my boss that I was going to retire. Then we began planning for it.
Within a month or so, I was gone. It was a looooooooooong month. Hahahaha.
What were your pre-retirement concerns (financial or non-financial)?
Retirement is a huge financial move.
If you’re like me, you were probably quite nervous the first time you purchased real estate. You had either brought more money with you than you’d ever spent on anything else or were borrowing more money than you’d ever borrowed for anything else, and you were wondering if it was a smart move or financial suicide.
Sheesh, I’m still nervous buying real estate these days even though I’ve done it a ton (because of the high amounts involved). FYI, I get the same nerves when wiring a lot of money somewhere (for a syndication, for example).
Anytime you combine large amounts of money with something you don’t do that often (like buy a house), it’s nerve-racking because you’re spending money on something you’re not really that familiar with. What if something goes wrong? There’s a lot at stake and you don’t have much experience at doing what you’re doing.
Retirement is that on steroids. You are making a 20 to 30 year multi-million dollar decision that you have no practical experience with. It’s like jumping off a cliff. Or maybe it’s like that leap of faith in the Indiana Jones movie.
Whatever it is, it’s a gigantic decision that’s not easily recovered from that involves everything you’ve worked for for decades, impacts your family in the most meaningful way, and with which you have no experience.
Does that make you shake a bit just reading that last sentence? It does me!
So given that, my only concern was “Am I going to be able to make it once I step off into the unknown?” For the answer to that, you’ll have to keep reading. Hahaha.
How did you handle deciding on and paying for healthcare?
I’ve written about this quite extensively, and eventually we selected a health sharing ministry as our healthcare.
As of this writing we have had it for our entire time in retirement.
You can read about the process we went through starting with Picking the Right Early Retirement Health Insurance.
How did you tell your family and friends of your plans?
We basically told everybody, I’m retiring. That was it.
But did they believe us? Some did and some didn’t.
The people closest to us believed. That’s because they had at least some insight into our finances and where we were financially.
But those who weren’t as close wondered what was going on. Had I been fired? Was I sick? Was I crazy? What was the problem?
Even people I ran into would ask “what are you doing this these days?” I would say “I’m retired” and they would give me the strangest looks. So I had to experiment with what I said to people. The basic “I’m retired” threw them for a loop.
Eventually I came up with “I invested in real estate many years ago when the market was low, and I have income properties that have allowed me to retire.” This seemed to be the one explanation that everyone could accept. So that’s what I went with for several years. Then I got tired of it, didn’t care if people freaked out, and went back to the basic “I’m retired.”
Did you have/make any plans for how you’d spend your time in retirement?
No, I did not.
I knew I would do more of the things that I was already doing, like exercising, walking, and writing for my website.
I also figured I would spend more time relaxing and enjoying entertainment as well as traveling some now and then.
And I figured I would explore some new things that were at that time undiscovered, and probably pick up a few activities here and there.
But that was really the extent of my retirement time planning.
As luck would have it, on one of our retirement walks my wife and I discovered these strange looking courts that had just been built in a park near our house. We learned the sport was called pickleball. It looked interesting since we had been tennis players when we were younger. We did a little research, ordered a starter set of paddles and balls from Amazon, and tried playing. From there the rest is history! Hahahaha.
While I didn’t really have a plan for how to spend my time, I did have a base of core activities that I enjoyed doing and knew I could spend more time with them. I also had the openness to try new things, in this case pickleball, to see if I could add to those activities, which is what I did.
THE ACT OF RETIRING
How did you ultimately retire?
I talked to my boss and told him I wanted to retire.
We then developed a transition plan for my retirement.
We implemented the plan over the course of a few weeks.
The last week or so was simply working to move most of my responsibilities to other employees.
My boss asked if I wanted to have a party or celebration of any sort, but I did not. I had a simple get together with me and my department employees in a conference room. We chatted and enjoyed refreshments for a bit and that was plenty for me.
The day of retirement was fairly surreal. I came in the office at my normal time and didn’t have much to do. I hung around for a while and then left early in the afternoon. That was it. It was a Friday afternoon and I was moving into the weekend as free as a bird.
What went well?
Pretty much everything.
I had enough money, and I had a (tentative) plan for how to spend my time.
With those two things covered, how could it not go well?
What didn’t go so well?
Pretty much everything went well.
There was an adjustment period, but it was very short as you’ll read below.
How did you ultimately find the courage to do it?
It was pretty easy. I hated the job and disliked working for my boss.
I had more than enough money and I was ready to leave.
I preferred freedom over anything else.
So there wasn’t really any courage required. Hahaha.
To read part two of this interview, see Retirement Interview 50, Part 2.