How I Retired at Age 50

About ten years ago, I hatched a plan to quit Corporate America and abandon my cubicle by the spring of 2020. I was oh-so-ready to hang it up in March of that year, but as soon as the pandemic lockdowns swung into place, an uncertain world put the “big plan” on hold.

Much bigger fish to fry with a deadly virus in circulation…

But after plugging away for another three years, I finally had my fill of the scene and resigned in June of 2023. The original six-year plan wound up becoming a nine-year plan. Oof.

It seems, in retrospect, like a cubicle prison eternity, but when there are two amazing little kids in your life, life flashes by in a blink.

This post is for the planners and strategists out there, folks who aren’t intimidated by spreadsheets, leveraging debt, and can stomach the marathon of long-term, conservative investing.

Know this: It is paramount for you to find contentment while working in a cubicle (and to find a purpose after you hang it up). If you choose to be frugal-miserable for several years in the hopes that retirement cures all, you’re in for a bitter surprise.

Investing and Diversifying

From day 1 at my first job, earning a salary of $27,500 with no bonuses, I started squirreling money into a “401k“. I contributed 8% back then while living a modest, though far from monk-ish, lifestyle.

I had a roommate to share the rent in an apartment, an okay car purchased new for $18K, and splurged on exactly two big trips in ten years. Travel was still a bit of a novelty way back in the late 90’s / early 00’s.

Coming out of college with over $20K in debt, I had no choice but to live within my means. Carrying credit card debt was scary to me. I had a collection agency come after me during my senior year, and that left a mark. The amount I owed was just under $200, but the collection folks are hardcore no matter what you owe.

Fast-forward ten years, and after a few job changes with good pay bumps, getting married, and owning a house, we were still in debt with barely enough assets to have a $0 net worth. Inspired by a silly (but at the time useful) book that shunned the 401k in favor of pure real estate, I went out on a bit of a limb and started investing in rental properties.

Taking Measured Risks

There are risks whenever you leverage debt for anything (a house, a car, an education, etc.). Rentals convey risk, but they work amazingly well when cash flow from rents is significantly higher than debt payments and maintenance costs.

We used our home equity and later a 401k loan to come up with down payment cash for the first two properties. Because we knew the market of the neighborhoods and had a solid cash-on-cash assessment for both houses, the risks were minimized.

Cash flow from our four single-family rentals paid for childcare during the twins’ pre-grade school years. The rentals were then put to use to pay off our home mortgage.

Meanwhile, my 401k contribution rose to 15%, and eventually, I got it maxed out. My wife’s practice started earning enough extra cash to allow her to set aside some money in a solo 401k, which is an amazing savings plan from a tax advantage perspective.

Bottom line: Our “portfolio” is as simple as a handful of solid rentals and 401k plans with a single large-cap index fund running on autopilot. Nothing fancy. No crypto silliness. It works.

Scrimping and Saving

The very first thing I’d recommend here is to find a home or apartment within walking or biking distance of your frequent destinations. Schools, grocery stores, drug stores, libraries, and even a coffee shop. If you live in the suburbs or rural area that requires driving to get to anything and everything, the costs (gas, wear and tear, insurance) will add up dramatically over just a few years.

The unseen cost is that driving everywhere takes away the opportunity to occasionally walk or bike to errands (or work). And if your lifestyle leans more sedentary, the cost of health care can eventually become a huge drain on the budget.

Even though we live within a short walk of just about everything we need here in Minneapolis, I couldn’t wait to retire and break free of the tether of work to my desk – home or office.

Scrimping and saving also means going meatless for most of the week (or longer). Not only does a plant-based diet save you money upfront at check-out, but it will improve your odds of avoiding heart disease, dementia, and cancer.

If you need a car, stick with paid-off vehicles and go with fuel-efficient machines that are easy to maintain. Avoid the fancy wheels until you have become financially independent.

When you have the money to afford the new tires and oil change for your fancy BMW, you can kick yourself for the pleasure and at least still be financially secure.

Accelerating and Inheriting

Accelerating is simply taking advantage of opportunities to pull in your retirement timeline. If you get a raise or a bonus, do you run out and buy a jet ski, or do you sock it away into your Roth IRA or post-tax savings? A jet ski is kinda fun, but they can be rented for the handful of times you’d want to use one in a given summer.

Are there job promotions you can push for at work? Sure, you’re trying to ultimately get away from the grind, but you CAN make the best of the situation while you’re stuck in it. Get that promo and start putting the extra dollars towards your kids’ 529s, your mortgage pay-down, or the new roof you need on your small but perfectly comfortable home.

If you’ve been fortunate enough to receive an inheritance, then use those dollars to pay off debts. Take the family on a cruise, and bolster your donations to good causes. I lost my father to cancer back in 2021 after a brief but very hard battle.

Sadly, he never got to enjoy the wealth he saved after decades of union work for GM. (Though admittedly, he was proudly cheap and seemed to enjoy living an extraordinarily frugal life. RIP, Dad!!)

Windfalls You Don’t Plan For

The gift of inheritance accelerated my early retirement. It fulfilled a large amount of college savings for our kids. It also paid for the renovation of our basement, allowing the kids to finally have their bedrooms. I’d be dishonest in this whole blogging enterprise if I glossed over the inheritance.

Key Point: Even without inheritance dollars, we still had the means to support early retirement. I learned that it’s mentally difficult to draw down savings. Whether it’s savings for your gap years between retirement and 401k distributions or the 401k drawdown itself. I suppose that’s why wealthy people work hard to maintain their capital and only at or near death give it away. I’m of the mind that donor-advised funds are the ideal solution.

Surviving Those Dreaded Cubicle Years

Another key piece to the early retirement puzzle is finding peace in your given situation. Working in a cubicle can be very stressful, and that stress affects your health and your relationships. Fortunately, there are effective coping solutions.

For one, you can hone your EQ skills and jujitsu workplace relationships to your advantage. In the worst case, you can get out of toxic environments by switching departments or companies altogether. Easier said than done for many. But with a new dynamic that’s more favorable to working from home, more options exist for workers than ever before.

Find a job that offers vacation time, has reasonable business hours, and no weekend work. Use all of the vacation time you’re given as it’s part of your compensation. Avoid checking in while away.

When you take all your vacation and go off the grid, you are essentially proving your value to your company. Ever notice how grateful colleagues and bosses are to have you back?

Ultimately, make the best of your cubicle years. And here’s the kicker: guess what happens when you land a job that you love? This whole concept of early retirement becomes moot. Those jobs do exist, but for many of us, they are unicorns.

Often, a great job gets ruined by a-hole bosses, organizational changes, mergers, etc.

My advice is if you want to retire by age 50. Even if you have the dreamiest of all dream jobs, always be planning for contingencies. Always be working towards financial independence.