Some days it feels like you’re stuck in the middle of a Tough Mudder. You’re crawling through the muck of your early-retirement plan, smelling the guy in front of you, ducking under barbed wire, and wondering when this will end. The goal seems so far away that counting down the days becomes a chore.
Then you hit milestones. Time keeps moving, whether you like it or not. The danger is forgetting to enjoy the present while you chase the finish line.
But hey—500 days to go! That’s worth a little look back. Here’s how I stitched together a plan to walk away from at-will employment in my mid-40s.
My journey started in fall 2014. I was fed up and, clueless, I googled “how to retire early.” Unsurprisingly, Mr. Money Mustache popped up. I read his blog from top to bottom—twice. His posts felt like they were written for my situation and gave me real hope. His case studies, with their blunt humor and solid lessons—like “Face punches” and “Debt Emergencies”—were both helpful and entertaining.
My first moves to speed up the timeline:
In 2015 I decided to grow the rental portfolio. We already had two houses giving us about $500 net each month. Since taking on Rental A in 2013, I’d learned a lot—how to avoid broken leases and how to find tenants with less stress. So in summer 2015 we added Rental C. That one was a pain to set up, but like I say, 90% of rental work is the initial setup. Today it nets $550 a month.
In 2016 we picked up Rental D. The market was hot; I lost about ten bids before winning D. It wasn’t as nice a neighborhood and it’s a one-bedroom, but the place was clean, well kept, and had a tiny yard—easy for a tenant to look after. The good news: I was still locking in sub-5% interest rates and keeping purchase prices under $150k. I knew, though, that as the market warmed and rates rose, deals like that would get harder to find. (Hence the Airbnb experiment.)
By the end of 2016, with four long-term rentals, I was about two years closer to my goal—down to roughly 1,200 days to freedom.
When I started almost four years ago, I had a choice: coast for five years or keep leaning in. I chose to lean in. Working smarter, not just harder, kept bonuses and raises coming. I even turned down two promotions to stay in a role that balanced work and life. No regrets—though I wouldn’t mind taking the next step now as a capstone.
An early-retirement target gives you a reason to hustle. As you get closer, your confidence at work grows.
There are things I won’t miss. And there are things I might.
As a project manager, I value planning. Mr. Money Mustache is right: build a margin of safety into your plan to handle the unknowns. With that in mind, I’m planning to share any “gotchas” that pop up over the next year and a half. How will I handle the unforeseen? Will something derail the timeline?
If you’re working toward early retirement, I salute you. It means you have things you want to do beyond your day job, and you’re likely to be more productive afterward. Go get it—we’ll make it happen together.
Funny thing: I thought I was decisive, but my countdown has been reset. Plans hit snags. My original exit was March 2020, then it got moved up to July 2019. Now it’s back on the table and I’m still carrying a lunch pail for the foreseeable future.
Why the change? A few things: FOMO, some unexpected expenses, job satisfaction, and, honestly, no solid Day One plan for retirement. For now the countdown is reset. Maybe I’ll aim to be done by 50. That’s farther out than Mr. Money Mustache (30) or some other bloggers, but that’s okay.
This isn’t a race. Most jobs are what you make of them. That perspective often gets lost in the rush to quit work early—something I’ve clung to for years.
There’s a thing called FatFIRE—a version of early retirement that lets you keep a comfortable lifestyle. Maybe that’s where I land. We did well with real estate this past decade, so maybe HeavySetFIRE is in my future. The benefit of FatFIRE: you can stop working but still enjoy dining out, travel, kids’ activities, or a nicer car. If you can swing it, FOMO matters less—you’ll still take that Europe trip and maybe bring the family.
I’ll write more on FOMO later. A lot of society keeps expanding what’s “normal” through hedonic adaptation. Big houses, electric cars, private schools—these things become the new baseline. Can frugal early-retiree types avoid adapting? I worry we’ll slide into new habits. In my neighborhood, modest ramblers are being replaced by McMansions. We all adapted to smartphones and two cars. I hope our family stays true to our priorities, but FOMO could nudge the countdown.
Unexpected expenses are a huge wild card. In the last year we had PRK eye surgery for two (about $3,000 total—half covered by our HSA), a new roof ($5,500), and a rented property’s concrete path replaced ($7,500). These hits change your timeline fast. No matter how well you plan, stuff happens. Health-care policy could shift, kids may need braces, or you might decide you want an expensive car. Those possibilities have to be built into the plan.
There’s also the unexpected cost of FOMO—once you start spending on new experiences, do they become habits? A Disney cruise or a trip to Hawaii can become routine if you let them.
On a brighter note, I met one of my mentors recently—Mr. 1500 Days to Freedom—when he was in town. A few local bloggers and I hung out at a brewery and talked at length about my indecision. Carl’s been out of the rat race for over two and a half years and has no regrets. We’re about the same age, and we share interests like beer and real estate. His advice: lock in on passion projects. Figuring out how to use your free time is the golden ticket.