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Retiring Early? Now What? What We Plan to Do.

Continuing the early retirement series, we have a problem. Now that I have had a chance to process our retirement plans beyond the cash-flow and sequence-of-return risks, we still have one big item to consider. What’s the plan?

The problem with retiring early is that you have 25-30 years of life expectancy. That’s a lot of time reclaimed from day-to-day commutes and mind-numbing code-switching work. No more set schedules or mandatory errands on limited weekends. All things considered, it’s not that bad. Besides, we might either expire sooner or get ill. The latter is a bit more terrifying based on current financial data.

Here’s some information to help you jump-start your own retirement savings. A 65-year-old couple in 2026 can expect to spend $375,000 on healthcare throughout retirement. Single people (over 65) will need to stash as much as $200,000 in savings to cover these expenses. These estimates cover Medicare premiums, deductibles, and out-of-pocket costs, but usually exclude long-term care. Note that for long-term care, private nursing homes cost over $10,000 per month. While the average stay differs, women should plan for an average of 3.7 years ($400,000+) and men 2.2 years ($250,000+).

However, if all things pan out for the best, my wife and I will have a runway of at least 20 years to fill up before any long-term care consideration kicks in. With that out of the way, we have a lot we can fill our time with and no shortage of ideas. To make it easier to grasp, I divided the plan into primary and secondary focus areas, flanked by optional activities.

A Quintessential Start – Year 1 of Our Retiring Early Saga

First things first, we are definitely packing up and heading south. There is no need to live in an area that drops near 10 degrees. Shoveling snow while your fingers freeze is not my idea of a good time.

Mantra – Retiring in the North is for Vikings or Fools

Our primary focus will be to move to Orlando (aka the family home with my in-laws). While others might feel stifled by living with their parents, my wife and I don’t. Besides, if we need more alone time, we can always rent a local hotel or, better yet, travel.

Part of the reason is to secure the old space from maintenance and upkeep. This includes cleaning, landscaping, and/or adding a fence.

I see it as having a home base of operations. Additionally, it will be a great opportunity to emphasize medical checkups and/or physical therapy. Moving back home saves on monthly housing costs while improving everyone’s overall mental conditioning. Living in separate locations has done quite a bit of damage to Western society. Multigenerational housing is a critical piece toward fixing financial insolvency and the ‘affordability crisis.’

Next up, we are selling real estate assets in the DMV. There might be cause for keeping the space and putting it under management, but that’s a bridge we can cross when we get there. The main idea is to limit unnecessary expenses and downsize liabilities.

Our secondary goals include staying in shape and/or picking up cycling. Since we intend to travel extensively, we will need to go to school for Spanish/Portuguese, supplemented by salsa classes for fun. The first big trip will start with 28 countries in the Caribbean (for 45-60 days).

Finally, we will need to structure our investments to gain $60,000 annually in Dividends. I’m also considering spending the time to write a book or pick up consulting gigs. So much to do already, on top of potentially becoming foster parents. The last part would certainly shake up a lot of plans (very likely).

The Locked-In Retirement Plan from Year 2 through Year 5

Continuing the trend but getting more locked into retirement, for years 2 through 5, it’s all scope expansion. Our primary focus will include family home renovations (i.e., Phase 1). This would include remodeling the kitchen, backyard, and adding more natural lighting. We may have to replace the AC unit and/or heater. Far beyond that, we might start locking into purchasing our 1st property overseas in Brazil or Portugal.

Retiring to travel
Retiring to Travel the World Over

If you haven’t noticed, our objectives from year 1 tend to bleed into the next objectives. For me, a great plan fosters synergy and balance. To quote George Lucas, “It’s like Poetry, it rhymes.”

We will also plan to see all 12 Countries of South America, and the 40 Countries of Asia. With four years to work with, we can knock them out comfortably. The best part is that we would have seen the whole of the Western Hemisphere. It’s all about ‘Slow travel‘ as we finish our language immersion through practical application.

Depending on time, I might head back ot school for financial planning. My wife is looking into creating an Event Space or Event consulting gig. Picking up contracts here and there is always a great way to challenge ourselves and engage more with the community. I’m sure that we will also purchase 1 or 2 properties as rentals.

I do need to structure our investments to gain an extra $100k annually in Capital Gains to fund some philanthropic initiatives like an endowment at our alma mater or some scholarships. With our passion for travel, I wouldnt’ mind working on Spring break or Summer Trips for teens and/or college students. To translate, we have a lot of experience in transcending our socio-financial class, which compels us to find a way to spark the next generation.

Even a Christmas Block Lighting event isn’t beyond our scope. While it might run us $15,000, it would be interesting to see. Some of these projects aren’t meaningful to others, but they light up kids while creating deep memories. That’s something special. Because of that, it’s worth pursuing. I’m this close to deciding on semi-annual barbecue day for the block.

The Final Piece of the Retirement Puzzle for Years 6 through 25?

For the final length, we will focus on finishing home renovations (i.e., Phase 2) and then venture to all 54 countries in Africa. While it might be a massive undertaking, I can’t wait to see a clear night’s sky with plenty of shooting stars. After that, we will set aside some time to see the remaining countries in Europe and the 14 countries of Oceania.

By 2040, we will be counted among the few who have ever visited every country.

Back on the domestic front, if we didn’t get the chance to set up a non-profit or philanthropic initiative by year 5, we should be all-tires on the ground for year 6. Plenty of room for scholarships, endowments, scholarship-housing, international trip grants, and/or hosting international student exchange. At this point, it’s all part of our legacy.

With time to spare, I’ll continue writing and publishing. Since our contemporaries will need to retire by 2050, we should have even more to engage with. Since all plans are subject to change, we will adjust as necessary. Be it health complications, family issues, or some other universe curveball, we will strive to go through life’s challenges with optimism.

Basically, there is a lot to engage with. Or not engage with. That’s the beauty of retiring early with the cash flow to support future endeavors. My wife and I didn’t come from families built on a legacy of wealth. Instead, the path has been quite the opposite. Because of that, we are making do with the limited time we have while impacting people who will never know that we ever existed.

With that thought, “The future is definitely interesting.”  

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