How Many Days Until I Retire? A 5-Year Preparation Journey

Some days you feel like you’re stuck in the middle of a Tough Mudder, crawling through mud and muck of your plan to retire early, virtually smelling the next guy’s dirty socks, while trying to keep under barbed wire. The goal post is so distant that tracking how many days until I retire is becoming pure drudgery.

Then you start hitting milestones. Time does have that wicked tendency to keep ticking away, doesn’t it? And if you’re not careful, you’ll do what many in this early retirement space are notorious for – not living for the moment.

But hey, why so wistful, Cubert? 500 days to go, man!!

Okay okay… A milestone like this is worth a little retrospective. Let’s review how I put the pieces together to retire from employment-at-will, in my mid-40s.

When my journey began in the fall of 2014, I had had enough. Without a clue, I must have Googled something like “How to retire early.” You can guess who popped up at the top of my search results.

The 1,942 Day Retire Early Plan

The very first thing I did was to study my butt off. And the best place to start was to read MMM’s blog from top to bottom, TWICE. Some posts seemed to know my exact situation and gave me instant hope. I found MMM’s case study posts the most entertaining and informative. Face punches and Debt Emergencies – good humor, with an applicable message.

The first actions I took to reduce how many days until I retire:

1. I switched to Geico. Course, I later switched to different outfit courtesy of my insurance broker. Bundling personal policies with rental property policies yields a very nice discount.
2. I ratcheted down our life insurance policies. The main thing here was to make sure in the event either of us croak unexpectedly, that we’re covered, i.e., status-quo. There’s no reason to correlate a death with winning the lottery.
3. I refinanced our home into a much lower 5 year ARM mortgage. This locked us in at a very low 2.625% interest and gave us the incentive to pay off the mortgage within 5 years. Sort of a “crap or get off the pot” kind of thing, with the biggest pile of debt most of us carry.
4. I went on a crusade to pay off our debts, using the cash flow index to prioritize and pay-down all of our 4.55% interest student loans.
5. I sold my Honda Accord in a private sale, and replaced it with a much more functional and fuel-efficient Honda Fit, for a mere $500 difference.

How to Retire Early at Age 45 (46, 47, and so on…)

In 2015, I decided to add to the rental portfolio. We already had two houses that were cash flowing pretty well, earning us around $500 each net profit per month. I learned a lot in that first year and a half since taking on Rental A in 2013. Particularly, how to avoid broken leases, and how to more seamlessly (and effortlessly) find new tenants.

So in the summer of ’15, we added Rental C. That one was a real treat to set up. If a house were a fingernail, this would be the one with dirt and grime stuck under it. As I always preach though, 90% of long term rental effort is getting it set up for the very first tenant. Today that house brings in $550 a month, net cash flow.

A year later in 2016, we added Rental D. This time, the market was heating up. I must’ve been beaten out on 10 offers before finally landing on “D.” The neighborhood wasn’t quite as sparkly as A, B, or C’s, and I had to settle for a single bedroom home, but the property was very well-maintained, CLEAN, and with a tiny yard, perfect for a tenant to maintain.

The good news was, I was still landing rentals with sub 5% interest rates, at $150K max price. But I knew that as the market continued to overheat in Minneapolis, and the economy recovered as well, housing stock would become even more overpriced, and interest rates would eventually go up. That’s where we’re at today. (And hence, the Airbnb Experiment.)

By the end of 2016, with four long-term rentals in the mix, I found myself two years closer to my goal: 1,200 days to freedom.

When I started on this journey, nearly four years ago, I had a decision to make: I could either mail it in and coast through the next five years, or I could keep on leaning in. I’m glad I chose the latter. Working smart, not just working hard, allowed the bonuses and raises to continue to flow, year after year.

I had two opportunities during this span to accept a promotion. I turned both down, wanting instead to perform well in my current role and keep a healthy work-life balance. I have no regrets looking back, but admittedly, I wouldn’t mind taking on that next level now, to capstone my career.

An early retirement goal, I’ve since learned, gives you more impetus to bust-ass. And as you close-in on your goal, your confidence in the workplace soars. 

Reasons to Retire Early

The question can dog you sometimes: “Am I trying to retire early to escape from something?” Often, you’ll come across comments or entire articles that drill you on this. Heck, I even posted last year about why you should never retire! Yep, we all have our moments of weakness.

Sam over at the legendary Financial Samurai wrote an excellent post a few years back about what you won’t miss when you retire early. Here’s my simple list – inspired by Sam:

What I won’t miss in 500 days, by Cubert

1. Friggin’ commutes. Just last night I was stuck in a half-hour crawl-fest to get home. I like to “do the math” on this kind of sh*t while I’m stuck in traffic. I figured that at an hour a workday (half-hour there, half-hour back), I was giving up nearly 500 days of my life to commuting. That blows.
2. Sitting on my ass all day, staring at a screen. Or lately, standing and leaning there like an idiot all day. We have stand-up workstations, but I’m not convinced that’s a cure-all for staring at a screen all day in a cubicle. F*ck. If I’m going to stare at a screen, I’d rather do it during my chosen window of time and produce something I care about (e.g., a blog.)
3. Office politics. Even if you’re a really good operator, you can’t avoid this one. I don’t let it bother me like it used to. But then, I’m probably shell-shocked now twenty-plus years into the corporate scene. Ultimately, it is taxing on the brain to witness really bad decisions by really highly paid executives, on an all too frequent basis.
4. Being stuck inside all dang day. Sort of in-line with number 2. But honestly, I wouldn’t mind staring at my screen as much, if I had a cubicle outside during nice weather. Practically speaking, I’d rather have the flexibility to get outdoors when I want and for as long as I want, with no technology involved. Health is Wealth. Yeah, we have a gym on campus, and yeah, I bike to work (after the ice melts.) But I’m a firm believer that optimal health and fitness is very hard to achieve while working a full-time job. If you are pulling it off today, what else are you sacrificing to make it happen?
5. Being bored. Funny I should put this one on the list. I just wrote about the fear of being bored in retirement. What a gas, huh? Well, it turns out that boredom can afflict even the most dedicated office trooper, well-before a traditional retirement “strikes.” Half the time for me anymore, the work itself just doesn’t inspire, even if the stated mission of the company does.

What I might well miss

1. The comradery. People are pretty neat, most of the time. There are several peeps at the office I enjoy chatting with, going for walks or a coffee. We commiserate and complain together. And sometimes there are fun happy hours. Volunteering in the community with your colleagues is fun and supremely rewarding. I will miss this aspect of the job most.
2. The pay. The bonuses. The benefits. But that’s why we all follow these bloody blogs, right??? …To get the mechanics fully understood and in place, so we don’t end up in a van down by the river.
3.  A wee bit of prestige. Sometimes it’s nice to don the sport coat and/or tie. Not often, but sometimes. And the chase up the ladder can be rewarding/thrilling if you manage to pull good reviews, and you know you’re on the radar for promotion.

Making the Best of the Next 500 5,000 Days

As someone who’s learned the value of preparing and planning (I’m a project manager for Pete’s sake!) I feel I’ve got a good handle on what I need to do to pull this off. Mr. Money Mustache is clear about this: You have to have a margin of safety in your plans, to account for the unknowns.

With that in mind, I’m excited to share with all of you over the next year and a half any “gotchas” that may emerge. How will I handle the unforeseen? Will something come up to throw the timeline way off track?

Speaking of “gotchas”… The big update from July 2019

If you’re on a path to early retirement, I salute you. It means you have some other passion in your life that you want to pursue outside of your current day job. It means you’ll be a MORE productive member of society after you’ve left behind your employment-at-will situation. Go get it. We’ll make it happen together.

Here I thought I was a pretty decisive guy. Now, it appears my early retirement countdown has been reset, yet again. Plans have hit a snag (or two). At first, the goal was to give up my cubicle job in March 2020. Then, it got accelerated to July 2019. Well, here were are, July 2019. And I’m still gonna be carrying a lunch pail for the foreseeable future.

Why am I changing course now? There are several factors: Fear of missing out (aka “FOMO”), unexpected expenses that popped up, job satisfaction, and you’ll never guess — No solid plan for retirement day 1.

For now, the countdown is reset to month X of year Y. Maybe I’ll just choose to be done by 50? That wouldn’t be so bad. There’s certainly nothing extraordinary about 50 and it’s a far cry from Mr. Money Mustache (30) and even Joe at Retire by 40, but I’m okay with that.

But I’ve got to remind myself that this isn’t a race. Most jobs are what we individually make of them. That’s what tends to get lost in all the rush and push among those clamoring to retire early (a group to which I’d clung for several years up until very recently.)

Delaying Retirement Due to FOMO

I just wrote about that Disney Cruise. And I still have all these hedonic treadmill gears spinning about how and when we’ll sail on the next one. I don’t necessarily think that’s a bad thing.

There is a phenomenon called “FatFIRE”, a truly American construct that allows the big winners (and physicians) to retire early and not have to sacrifice the fruits of our commercial heritage. Maybe that’s where I’m destined to land? I’m no doctor, but we’ve done pretty well this past decade with the real estate side hustle, so maybe HeavySetFIRE is an objective?

The beauty of FatFIRE is you get to have your cake and eat it too. Tired of working? No problem. You can hang up the job, but avoid having to sacrifice the good stuff (dining out, travel, having kids, a Tesla in the garage…)

If you can muster FatFIRE, there’s less reason to dread your early retirement countdown. It’s all good. FOMO be damned – you’re going to take that trip to Europe, and you might even take the family with you!

It’s a topic I’ll spend a future post on – this whole FOMO thing. A good chunk of our society is continuing to expand its norms via hedonic adaptation. Soon enough, the “haves” will make these accouterments (big houses, electric cars, private school) the new NORMAL.

The question is whether frugal, early retiree types can avoid adapting themselves. I look around our cute little neighborhood and it seems every other week a new McMansion has replaced a modest 1500 square foot rambler. We’ve all adapted to “needing” smartphones and tablets, and “needing” two cars in the garage.

I’m still optimistic that our little family unit can stay true to our True North. But I do have some hesitations about how FOMO will affect this guy’s early retirement countdown…

Unexpected Expenses Delay Retirement

There have been a few of these over the past 12 months. From PRK eye surgery for two ($3,000 – the other half was paid by our HSA) to a new roof on the house ($5,500), replacing a concrete pathway at a rental ($7,500!!!)

And now a new one — some upcoming legal fees for allegedly using a copyrighted image without permission on THIS blog. More on that later.

So, you know, that stuff adds up!

Money “gotchas” present a big variable to anyone’s early retirement countdown. I don’t care how good of a planner you are. Stuff happens. And who knows where future policy decisions on health care will land? What if the kids need braces? Will I eventually need a Tesla Model S? All of these things have to be taken into account.

I’m not certain this falls in the category of “unexpected”, but what about the unexpected cost of FOMO? If we start to pick up new and exciting things to do with our money (e.g., a Disney cruise, or a trip to Hawaii) do these things become habits?

Fortunately, I got to connect with one of my gurus earlier this week. Mr. 1500 (Carl) was in town and I, along with a small group of top-notch local bloggers got to hobnob with our guest at a rather Surly brewery. We got to talking about all my indecisiveness as the supposed early retirement countdown clock ticked away.

See, Carl has been out of the rat race for over two and a half years and has no regrets. We’re about the same age and have some similar interests, beer and real estate among them. He told me to lock in on passion projects. Figuring out how to best make use of your newfound “free time” is the golden ticket. Indeed…

When Job Satisfaction Holds You Back

When you get promoted, it’s as if you’re being recognized for surviving the sh*t-show of Corporate America. All of a sudden, there’s a vindication of the political wrangling, monotony, and wasted effort, that goes hand in glove with the big wins, commitment, and resilience you’ve demonstrated.

It’s hard to take a step back when you actually, finally get recognition (take note, all bosses and managers reading this…) I mean, it’s not like work is paradise now. On the contrary, things got quite hectic right at the time of the promotion, earlier this year.

It wasn’t until May that I decided to double-down on my productivity at work to re-balance time with non-work commitments. Work is still very demanding, but there’s a real sense of achievement and pride when a well-deserved promotion comes along, and you feel your decisions and actions make a difference.

Here’s another “out of left field” notion: Global Warming. Yes, global warming is keeping me tied down to my job right now. Why? Well sadly, the weather here in the Upper Midwest has been sh*t. Yes, we live here on our own volition, but no, we do not expect every day to rain, humidity, and clouds. It’s as if we’ve gone straight from winter to the Amazon rainforest.

There is no fear of missing out on outdoor activities, while perched inside the air-conditioned confines of headquarters. I haven’t been able to ride my bike to work more than once, maybe twice a week on average this summer due to weather shenanigans. I don’t mind riding in a little rain, but I draw the line at lightning and monsoon downpours.

It’s Not Easy to Travel When Kids Are in School

There’s an “unevenness” when one partner in a couple retires early, while the other continues to work. It’s also a tad difficult to travel the world when your kids are in school and have begun to establish their rhythms, routines, and friendships.

Now that we’re locked into a school calendar for vacations, it’s that much harder to book good flights. Everyone wants to go somewhere during Thanksgiving, Christmas, and spring break. Airlines know it, hotels know it. And Disney sure as shootin’ knows it.

Even in early retirement, my “vacation” time would not change. I’d still be pretty much adhering to “the calendar”. The one that our local schools publish. Oh, and then there are the patients who don’t like it when Mrs. Cubert is away from the clinic for more than a week or two.

So yeah, talk about FIRST WORLD PROBLEMS…

I do believe this whole early retirement idea is a sound one. If nothing else, it motivates us to get our financial act together, and maybe even become better stewards of the planet. Ultimately there are three beliefs at the forefront of my decision making:

1. Thou shalt have no regrets when the bell tolls
2. Life goes on, regardless of whether you’re in the office or at home focused on passion projects
3. You’ve only got one life to live. Each day is a gift. How will you make the best use of that gift??

Whew. That’s a lot to stew on, particularly for someone spotting age 50 on the horizon. If I’m not done by then, my name is MUDD. But at least I’ve gotten over the Sunday Scaries!