A Behind-the-Scenes Glimpse Into Early Retirement

The reality of being retired in your 40s... from someone actually doing it

I'm writing this on March 26th, 2024, exactly 18 months after I officially announced my retirement.

I remember that day like it was yesterday. It was the company's annual meeting, where those of us who worked in head office presented a year-end summary on our divisions for the rest of the company. It was a huge event, with everyone of any importance gathered in one place. We prepared for weeks, tweaking and retweaking our presentations endlessly in an effort to make them perfect.

I was particularly apprehensive about 2022's edition because it combined two of my least favourite things -- public speaking and giving people bad news. My presentation was also last, which just ratcheted up the pressure.

With my knees practically knocking together and sweat pouring from my armpits, I got through my talk and gave everyone my big news. I was leaving the company… to do nothing.

I awaited everyone’s reactions, expecting the worst.

But pretty much nothing happened. 

There were no gasps of horror or people fainting in surprise. Folks collectively shrugged and moved on, probably relieved they got to go home after a long day.

The news apparently had sunk in by the next day, because I was peppered with questions. What was I going to do next? Most people assumed “retirement” was code for something, with many convinced it really meant working for a competitor. I assured everyone that wasn't the case. I planned to sit back, relax, and focus on investing.

Others were concerned I didn't have enough capital to pull this off, as if their very incomplete glimpse into my finances somehow gave them some sort of insight. I must've been in a good mood, because I actually placated these people. These days I don't even bother responding to such criticisms.

A couple well-wishers were concerned about what I'd do all day. They couldn't envision a world where their time was entirely their own, so they were curious. How could I possibly fill all that time? Won’t I get bored?

I had the same answer then as I do now. Boredom has not been a problem. We’re now a year and a half past my early retirement decision and I can firmly say I’ll never return to traditional employment. Ever.

This post is to answer those naysayers, but it’s mostly for those of you working towards your own early retirements. I’ll talk about what a typical day looks like, but mostly I’ll talk about what’s great about it and what’s not-so-great. Yes, there really are drawbacks of early retirement.

Sign up for my FREE newsletter for more thoughts on early retirement, dividend investing, and a whole lot more. Straight into your inbox. No crap, I promise.

A typical day

One of the best parts of early retirement is I don’t really have a typical day. Sometimes I’m travelling. Other times I might sleep late and go for a nice brunch. Or I might wake up at 5am and start cracking open annual reports by 5:30. My life is conducive to whimsy, and I try to take advantage of that.

Usually I wake up around 6:30 or so, and without an alarm. One of the first things I did in early retirement is ditch the alarm and let my body wake up naturally, and it’s been wonderful. Breakfast is usually toast with peanut butter, but sometimes I’ll have eggs. I’ll check Twitter and hang out with my cat for a bit (he loves the garage), and then I’ll head off to get ready for the day. By 7:30 I’m typically ready to go.

7:30 is when the market opens, so I’ll spend a few minutes checking the big stories of the day and looking at my portfolio for big unexplained moves. By 8:00 I’ve usually moved onto more substantial reading, and by 8:15 my nose is buried in some piece of research.

Sometimes I write about the companies I research for the premium version of this newsletter, but I’m mostly doing this for my own portfolio. My aim is to keep myself at least halfway updated on most dividend paying stocks that trade on the Toronto Stock Exchange, and I find that an hour or two worth of research on each company every few months does the trick. Then, when I consider the price to be attractive, I can dive in and make a buy decision fairly quickly.

Some investors yearn to learn every last detail of the stocks they own, convinced that level of knowledge will protect them if the business ever goes south. What I’ve seen is the exact opposite thing happens — it creates a false precision and one’s ego gets wrapped up in the name. They’re unable to separate the forest from the trees; they’re simply too invested in it.

I want to avoid such a fate, so my time is spent trying to identify the major drivers of each stock I research. Once that’s accomplished, subsequent research gets a lot easier.

I’ll usually spend the morning reading about stocks and periodically writing about them. As I stumble upon interesting facts or attractive investment opportunities I’ll tweet about them, usually scheduling them for later.

The afternoon is really where I switch things up.

Typically once or twice a week I’ll go for lunch with somebody. Some of my friends are still working, while others are retired or have more flexible schedules. The flexibility of my lunch mate’s schedule often determines how long lunch will go. They can sometimes last hours as we talk and debate a whole list of topics. Once or twice a week I’ll go for lunch alone or with my wife. Other days I’ll make something quick at home and go back to work.

After that is really unpredictable. Sometimes I’ll stay out and do my weekly grocery shopping, using my retail experience to get the best prices by stopping at multiple stores. Other times I’ll come back home and write something for y’all. Midweek afternoons are a great time for other errands. I might take a book with me to lunch and spend a few hours reading it. I might go to the library and find a physical book and comfy seat. If there’s a good movie playing — especially on cheap Tuesday — I might catch an early show. Nobody goes to movies on Tuesday afternoon. It’s great.

Golf has become a priority in the summer, so the warmer months will feature more random day trips to fun new golf courses, as well as my weekly Thursday tee time with my ex-work chums. I’ve even been brave enough to show up randomly at a course and say “hey, I’m a single, got anyone I can play with?” It’s a great way to meet new people.

I just about always make dinner these days, and I find I immensely enjoy cooking. I’ve learned how to make a few delicious dishes and a bunch of other things moderately well. It saves us money, is more nutritious than eating out, and lets me be creative with the ingredients I buy.

After dinner is when I decompress with my wife. Sometimes we’ll watch TV, or go for a walk, or go for an after dinner beverage. Other times she’ll do her own thing and I’ll play video games — specifically MLB: The Show. I also like to follow baseball, so I’ll often have a game on in the evenings.

So many people worried I’d get bored during early retirement. I can honestly say I haven’t been bored at all. How can I be when there’s literally a whole world of things to do or places to explore out there?

An atypical day — travel

A big reason why I retired early was to have more time to dedicate to travel. In fact, the very first thing I did after telling my boss I intended to retire was buy airfare to London to celebrate.

2023 was the year of travel. I spent more than 10 weeks away from home, going to the Netherlands, Germany, England, Scotland, Washington D.C., Montana, South Dakota, Wyoming, Ottawa, Toronto, and Japan.

I won’t travel as much in 2024, but I did go to Colombia in January and have a trip to Minneapolis scheduled in a few weeks. I also plan to do at least a couple golf trips closer to home this summer, and have tentative plans to go somewhere in November or December. This year’s travel schedule will see me spend something like 5-6 weeks away from home.

The travel schedule will ebb and flow each year depending on whether my wife can find good travel deals and what we feel like doing. I also think Canada is a wonderful place during the summer, so I’m likely to stay closer to home when it’s warmer.

I was away from home enough in 2023 to experience some of the little-mentioned downfalls of travel. It’s stressful to plunk yourself in a strange city where you don’t speak the language and try to figure everything out. In small doses, the adventure wins out; it’s exciting to try and figure out a new place. But after a while, fatigue sets in and you don’t want a challenge any longer. You just want your bed and your cat and your regular lunch order back.

The downfalls of early retirement

I’ve already covered the benefits of early retirement — like lots of free time, total autonomy, having the freedom to write stuff like this without worrying about how it’ll pay the bills — but it’s much more interesting to talk about the downfalls. So let’s do that.

By far the hardest part of early retirement was switching from a saving to a spending mentality. To get to the point where I am now, I saved an average of 50-60% of my income every year for two decades. I delayed vacations and lived in a cheap small town and drove an older car.

I got into the habit of saving large chunks of my income which I’d then invest into dividend paying stocks. Each time I put that capital to work, I’d update my spreadsheet and watch that succulent passive income increase. It got to the point where I pretty much got addicted to watching my dividend income go higher.

These days, my dividend income does slowly march higher — since I withdraw approximately 66-75% of my dividend income each year and reinvest the rest. Most of the stocks I own also increase their dividends annually. But it’s much slower than before, and it does feel a little bit like I’m falling behind.

I spent a ton of time reading, talking to other early retirees, and pondering my future back when I was thinking about retiring. I remember considering this very issue and thinking I was over it. Alas, I was not, and I still struggle with it. It hurts every time I take money out of my accounts.

Another big downfall to my early retirement is I spend a lot of time by myself. Work forced me to interact with people when I’d rather just be left alone, which I think was a positive aspect to it. It forced me to be a little more social than perhaps I wanted to be.

As I mentioned, I do spend quite a bit of time with my friends. I also make sure I stay in touch with a random text or a funny meme in between visits. I definitely spend more time with friends than when I was working. It just pales in comparison to spending 40+ hours a week surrounded by people.

Finally, there’s the gnawing doubt that I’ll run out of money — even though I have multiple safeguards in place. The logical brain thinks it’s a silly feeling, but my less evolved lizard brain still has doubts — and nothing will ever fully relieve that feeling. My net worth could double and my lizard brain would feel the same way.

There seems to be a misconception that FIRE devotees like myself do things like live in a van down by the river and eat nothing but delicious cheap ramen. The reality is my life is very similar to most other middle class lives. I live in a nice house in a good neighborhood in a top Canadian city that’s a little too big for two people, I have friends and hobbies, and have more time to travel. It’s honestly pretty great. I want for nothing.

Final thoughts

Overall, early retirement is the ticket. I get to spend my days exactly how I want, and I have the freedom to throw any routine out the window if I’d like. I travelled more in the last 12 months than my grandparents travelled in their entire lives. It’s a privilege to have that freedom, and I thank younger Nelson every day for his sacrifice.

Considering how immature young Nelson was with everything else, I’m quite impressed with his financial acumen.

One thing I realized as I approached early retirement is my sacrifice was pointless without a reward at the end. I scrimped and saved for two decades only to live in fear of losing my job just like my colleague with $5,000 in savings. Realizing this was a big reason why I was finally able to take that leap.

The sacrifice wasn’t easy. In fact, it was pretty damn hard. And early retirement isn’t all sunshine, lollipops, and rainbows. There are some negative aspects to it. But, overall, if you gave me the option to go back two years and have my old life, the answer would be a resounding no. Sure, sometimes I miss the way things were, and it’s rewarding to work with people towards a common goal, but I just couldn’t go back. Not after tasting freedom.