A Look Back At 2023's Top Posts About Living The Semi-Retired Life

Part one

I don’t believe in New Year’s resolutions.

But I do believe in checklists, as long as they’re part of a comprehensive and thoughtful system. We started to formalize semi-retirement as a comprehensive and thoughtful system a few months ago.

Semi-Retirement Is A Lifestyle, Not A Work Arrangement (Part Two)

The risk we run with ideas such as semi-retirement in our society is that they become fads. Cool-looking social media hashtags. A risk because—suddenly—everybody wants to do it. However it’s often more talk than it is action and sustained commitment.

In the above-linked series, we developed qualitative components of Living The Semi-Retired Life. Today, we continue discussing more practical (and psychological) aspects by looking back at some of the best stuff we discussed in 2023. Tomorrow, we’ll do it again. Then we don’t miss a beat for 2024 and 2025’s big plans.

I love end-of-year summaries, as long as they pack good information and inspiration into one comprehensive and cogent punch.

I hope this does that for you and—if you haven’t already—prompts you to upgrade to a paid newsletter subscription so you can fully participate in 2024’s journey, which steamrolls us into January 2025’s move to Spain.

To be semi-retired requires planning in pretty much all aspects of life. Even though I consider myself semi-retired today, I realize there are a series of levels on the road to full-blown semi-retirement. There’s work that needs to be done ahead, during and all of the time.

This newsletter effectively creates the handbook on living your iteration of the semi-retired life. It’s an ongoing, always-evolving process.

Today, I pull a few of my favorite—and most important—written specimens from 2023.

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• Perfecting the work and money meets life equation.

Part Four: How To Theorize And Strategize Your Semi-Retired Life

The less money you’re on the hook for each month, the less income required. Plain and simple. It’s what we discuss all of the time. The concern about taking on too hefty of a housing or car payment and knowing that, each and every month, you have the pressure of hitting that number.

A low cost of living, particularly on your biggest fixed expenses can help relieve or eliminate that pressure …

I want to live a soft, easy, semi-retired life with less work, but I don’t want to do it at the expense of discretionary spending and monthly cash surpluses.

So I had to look at my work. This is what I did as I transitioned back into freelancing during the stay-at-home portion of the pandemic, now three years in the rearview mirror.

While you probably can’t directly apply my experience and process to whatever yours was, is or will be, you can likely look at what you do for a living—or want to do for a living—and adapt it.

I theorized a life where I could work in short 1-to-4 hour spurts, once or twice a day, no more than 20-30 hours a week, five days a week with two days—usually Sunday and Monday—where I don’t work at all. I also wanted the freedom to take other days off randomly as well as longer, pre-planned periods of time to rest, recharge and/or travel.

I strategized by looking at the work I do and breaking it down into bite-size pieces. Increasingly smaller, more manageable and less stressful bite-size pieces.

So much of this comes down to organization. Of having visibility of 2-to-4 days out, knowing what you need/want to get done in that period, then methodically knocking off each task, one-by-one.

I used to think you could only do this as a freelancer or small business owner. However, thanks to a trend the pandemic helped rapidly accelerate, you can be a full- or part-time employee and, relatively speaking, call your own shots on timing. It has a lot to do with remote work, but also workers demanding greater autonomy from employers.

Because let’s face it. You waste more time in an office on a rigid schedule than you do at home.

Here’s how I like to organize my work, from the above-referenced installment—

• Complete a 1-to-2 hour work task.

• Take a 20-to-40 minute walk around the neighborhood.

• Complete another 1-to-2 hours of work.

• Take an hour long walk that includes a stop for coffee or a snack.

• Come back and wrap things up (maybe another hour or two of work) and set things up for the next day.

When I worked in an office, I basically did this. But—my co-worker Thomas and I felt like we were sneaking around as we strolled Downtown San Francisco during the workday. We’d get side-eyed when we walked back in the building, then basically fuck off half the time at our desks.

And we were still two of the top and most reliable people in the office.

At home, you can produce, not get side-eyed (except from maybe your cat) and use your downtime freely and more productively.

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• When you organize work and money around your life you can live more evenly across the lifespan.

Part Six: The Financial Component Of Living More Evenly Across The Lifespan

Most people don’t live evenly across their lifespans.

It’s certainly a cultural thing. A very American thing.

• Get this or that out of your system in your teens and twenties.

• It’s time to settle down, buy a house, maybe move to the suburbs now that you have a steady, stable job.

• Work hard now so you can enjoy it later.

• In a few more years, you’ll be able to rest.

All statements most of us probably never thought twice about until we started thinking twice about them.

The prevailing lifestyle in the United States looks like this—

• Get a job. Move up the ladder. Make it a career.

• Start making good money. Rent an apartment. Buy a new car. You deserve these things because you’re working hard and making good money. They’re a reflection of you.

• Start saving for retirement. Contribute to the 401(k). Take the employer match. Maybe open an IRA. Start saving for a down payment on a house.

• Buy the house. Move in. Fill it up with furniture and other accessories. Buy a better car.

• Move to a bigger house. Settle in until you’ve saved enough to comfortably retire and quit work altogether.

• Retire.

• Die.

Thankfully, this linear lifestyle is no longer the norm for an increasing number of people.

However, even if people are leading non-linear lifestyles—essentially doing things out of the order their parents or grandparents might expect—many still stick to the same core principles of saving for traditional retirement and home ownership.

The double whammy of traditional retirement.

It’s not that there’s anything inherently wrong with traditional retirement or home ownership. It’s just that they’re obviously incredibly difficult to do, especially at the same time. We have been asked—and often expected—to do what has proven anywhere from impossible to soul crushing for millions and millions of people.

There’s a reason why we have a retirement crisis.

There’s a reason why most people can’t afford to buy a house.

There’s a reason why, over the last 10 years, you hear so much about work-life balance.

There’s a reason why quiet quitting, going part-time, working in the gig economy and semi-retirement have become things over the last couple years.

Because the status quo doesn’t work for many people. Even with this writing written permanently on the wall, we attempt to maintain—to strive for—the status quo. We take a clearly collective problem—a problem with our overarching ways of organizing life—and internalize it as there must be something wrong with me.

Guess what? There’s nothing wrong with you if you can’t be successful following a model that could only work when it worked—for a few decades coming out of WWII when the sole focus was getting people in motor vehicles and suburban homes.

Circumstances—economic and otherwise—have changed. It’s impossible, if you’re under 50 and haven’t already done it, to do what your parents and/or grandparents did.

That is if you prefer a life doesn’t revolve around work. Because if you go all-in on the double whammy of traditional retirement today—or even just yesterday—that’s what you’re signing up for. Just thinking about it makes me love life less.

The solutions?

Live—and manage your money—more evenly across the lifespan.

Or, as I sometimes call it, live and manage your money backwards.

Here’a a rough sketch. We get into the specifics of each in forthcoming installments this month.

• Find and maintain a low cost of living. Use backwards budgeting to help get there.

• Work less than 40 hours a week—hopefully much less—to meet your fixed expenses and have regular monthly surpluses to spend and save.

• Direct your surpluses to pots of money, each earmarked for specific near- and long-term needs and wants.

• Don’t buy a house if it doesn’t make you better off financially today—immediately—than you were yesterday.

• Don’t stress over saving for traditional retirement.

• Don’t forget that you’ll probably collect Social Security. And, if you have a low cost of living into relative old age, it will be a meaningful amount of monthly cash flow.

• Aim to have no or a low housing payment once you enter relative old age and beyond.

  • This might mean you have paid off the house you bought. The one you didn’t have to struggle to buy and service. But the one that made you better off financially and didn’t sentence you to a stressful life that revolves around work.

  • It might mean my backwards plan. Save money and once you have a nest egg accumulated, use that cash to pay cash—or close to it—for a property in a place that’s affordable where you actually want to live.

• Work a modest numbers of hours per week—or craft and nurture some other form of cash flow—to use in relative old to cover your super low cost of living (with no or a very low housing payment) and discretionary spending.

Instead of packing more than 62,400 hours of work into 1,560 weeks, do it over 3,120 weeks. That’s the difference between working 40 and 20 hours a week over 30 years.

Bottom line—It’s the difference between heading into relative old age overworked with not enough saved or going there capable and vibrant so the reality that you don’t have enough saved is an afterthought.

A look to Downtown Los Angeles from a hike we took before this week’s rain.