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I was sitting at my desk in a huge D.C. office building, wearing a tie and cruising job websites for a new direction in life. An ad caught my eye: “Island Manager.” A land trust that owns a small, uninhabited island off the coast of Massachusetts was looking for someone to do landscaping, greet visitors, and generally keep an eye on the place from June through September. $12/hr. They were also hiring a ranger to assist the manager ($9/hr.). I sent the link to my wife as a half-joke.

“When do we start?” she replied.

Three months later, on a very chilly evening just before Memorial Day, we were dropped on Great Misery Island for the summer. Spending the next four months mowing grass, cutting trails, and chatting with visitors (with no electricity, no running water, no TV, no internet, and only spotty cell service) gave us a new perspective on how we should be living our lives.

Aerial view of the two Misery Islands.
The Misery Islands, Great Misery and Little Misery. Visit if you can.

Up to that point in our mid-30s, we’d embraced the city-life hustle in D.C., both of us working relatively prestigious professional jobs. The pay wasn’t fantastic (we worked in government and journalism), but we lived modestly and saved aggressively, despite our more-than-occasional splurges on fine dining, parties, and vacations.

But spending a few months staring out at the ocean, reading books, cooking fresh-plucked mussels, listening to a solar-powered radio, and having the surf lull us to bed changed everything. Suddenly the money we’d been diligently socking away represented not a comfortable old age 30 years away, but the prospect of a simpler, less-stressful seaside life as soon as we could figure it out.

It took us two years, but one shining September day we were on the ferry to Martha’s Vineyard to begin a new chapter of our lives.

Our DC friends were startled and not a little envious of our move. More than one ruefully admitted that they could never begin a new life wholesale, with far less income. But the there’s no magic: F.I.R.E. (Financial Independence, Retire Early) can be for almost everyone. With a few simple principles, you can do less of what you think you need to do, and more of what you want to do.

“Retirement” #1

After our glimpse of a slower seaside life on Misery Island, we didn’t just “end up” living on the island of Martha’s Vineyard. We made it happen. The steps as I see them are: 1) Imagine, 2) Plan, 3) Budget, 4) Save.

The first step is the most important. It is also the easiest and most fun. Just imagine. Let your mind wander to where you want to be, what you want to be doing. I actually don’t like to use the word “retire” in this context. Very few people want (or can afford) a life of total leisure. Your dream needn’t be a radical change, or it could be a totally different life. Couples and families will likely have to compromise, but finding a shared dream is magical. Our dream was a quiet life by the ocean, riding bikes.

Planning is not nearly as fun or easy. But goals without plans are just that: dreams. Once you have a plan, it becomes a goal. For us, this meant thinking hard about where by the ocean we wanted to live. Florida? The Mid-Atlantic? New England? California? The Pacific Northwest? Then we did research. We had both grown up in New England, and had family and friends there. So we started planning for that, looking at jobs, housing costs, etc. Based on the income we could generate, we could look at the cost of living and see if only one or both of us needed to work, and how much.

We have always been comfortable setting a budget, so when my wife was offered a job, we quickly knew what we would need, and what we could give up. My wife, a journalist, was offered a magazine job on Martha’s Vineyard, and we figured out the salary that would be necessary to make a go of it on Martha’s Vineyard, and we were able to negotiate up to that. We owned our house in D.C. with a lot of equity, and even though housing on MV is eye-wateringly expensive, we could afford something there if we were willing to fix it up, which we did. It’s important to be realistic about this step; most things cost way more than we anticipate. This was true of our move, and one reason I decided to get a job so quickly when we got to the Island.

Save. This is the hardest step, but we had always been big savers, so we were able to make the move without delay, knowing we had a cushion if things didn’t work out. We didn’t want to touch our savings, so we needed to cover our living expenses with our income. Our savings represented even more potential freedom in the future, which was another big impetus for me to continue working.

Photo of Martha's Vineyard in the summer showing a lighthouse and a small sailboat in the distance.
Martha’s Vineyard was pretty nice. In summer.

Again, you might object to calling this “retirement” since there was still work in the picture. But our move wasn’t about lazing around all day. It was about leading lives we wanted and could afford. For my wife, going from a pressure-packed newsroom with daily deadlines (picture All the President’s Men) to running a lifestyle magazine was a delight. For me, I did some freelance writing, and then found a municipal planning job I thought I’d try. Learning new things is exciting for me, so I enjoyed it for a while. But after a year or so, I got restless and stressed. I was again working full-time at another job I didn’t love, and the house was devouring all our free time and money. Was this “retirement”?

So I quit for a part-time gig working on environmental projects. I loved it; a typical day might be spent on paperwork, doing lab work, or scuba diving to count scallops. I had much more time to work on our house (I joke we saved dozens of dollars doing jobs ourselves). We had time to make friends.

With the house done, the relaxed beachy lifestyle we envisioned at our desks in D.C. became a reality in a quaint seaside haven. We had jobs we enjoyed and friends we adored. I had hundreds of miles of quiet country roads and beautiful trails on which to ride my bikes. We pondered having children.

Back to Work

We had the life we’d wanted. So why blow it up? Well, the only constant in life is change, and the things we wanted changed.

Most importantly, the quiet life is… quiet. Especially in winter. “The Rock” (as MV is not-so-affectionately known) is pretty dull and cold in the off-season. Beaches and sailboats are of little comfort the eight months or so each year when it’s too frigid to enjoy them. We escaped to Florida for six weeks each winter, but we still started to chafe at the limitations of Island life after seven years.

Also, our financial goals changed. I was sitting at my desk one day thinking that I had a great, cool, fun job for someone in his early 40s. But it wouldn’t be so cool in my early 60s. And because it didn’t pay well, I’d be there that long if I wanted to save up enough to finance a “real” retirement. We were still saving, but the Great Recession had given us a scare. Even though we had decided against having children, we felt like we needed a bigger cushion. And my wife was growing restless in her job as well.

Stay Flexible

So we started to imagine what we wanted, again. A warmer climate. A new challenge in a new place, with a higher income. And again, we didn’t just “end up” in a new place. We had to plan and work the plan. We thought for a while that we’d move to San Francisco, but then things that looked promising fell through. Not discouraged, we kept at it until we both applied to jobs in San Diego. We visited the city and loved it; all the ocean we wanted, with the city life we’d started to miss, and mountains close by to boot. And the best weather imaginable.

I was offered a job. Our budget said that we could live well on that one income, and that a job for my wife would provide the savings we wanted. So we headed west. As it happened, my wife was offered a job a couple days later.

A palm tree lined street and a boardwalk with people watching the sunset on the ocean. San Diego is a great place to "retire early".
San Diego. Nice all year.

So we were back in the rat race, to a degree. I told my wife I could do my new job for five years, and then we’d likely have enough to “retire” again. I didn’t love my new economist job, but I liked it well enough. And it was fulfilling: a public sector job making San Diego a better city for everyone. My wife loved her new journalist job, despite the modest pay, but hated the commute from our new, small house in a fun, walkable neighborhood near downtown.

So it wasn’t perfect, but it was pretty darn nice. And we were making progress on the financial plan. It was a balance between maximizing our incomes totally, and having a good quality of life in the meantime.

We paid off our house. I hit the five-year mark at work, and that day asked to reduce my hours to 30 a week. This was a gamble, but after five years, we’d saved enough that I was prepared to walk away if they said no, which they didn’t. But when you ask for something like reduced hours, most employers look at it like you’re asking for reduced responsibility (which I wasn’t) or demonstrating reduced commitment (which I guess I was). I was gently stripped of my supervisory duties. And I began to feel a little “out of the loop” at times, not because I wasn’t around enough, but because management wasn’t accustomed to an employee who advocated for a healthy work-life balance.

After a year, I decided it was best I move on. Frankly, it is emblematic of a work culture that sometimes pays lip-service to “work-life balance,” but almost never actually accepts that concept. It’s their loss, frankly, as talented employees decide to leave.

Of course, around that time my wife was laid off when her company was sold. She got another job fairly quickly, but it wasn’t a job she loved. So she kept looking for a job that would speak to her, and she found it a few months later at the local humane society. She loves animals (we both do), so putting her skills to use helping critters was another “dream job,” except for the fact that it paid about half of what someone with her skills and experience should be making. She took it anyway; what is the use of working toward “freedom” if you don’t feel like you can take advantage of it?

Retirement #2

Even with her greatly reduced income, I still decided to leave my job. I had been working since I was 16, so I felt entitled to take some time off, and our cost of living was pretty low.

I left at the end of 2019. And haven’t really looked back. Sure, there were a few tense moments early in the pandemic when the economic future was terribly murky. But the truth is that I would’ve hated working from home (my wife loves it).

I also lost two friends my age within a couple weeks of leaving my job, one to cancer and one to suicide. The loss of those friends was a bitter reminder of why I was leaving: Life is short. What are you living for? My wife and I have been lucky to have each other, lucky to be healthy, lucky to be educated by caring parents (who valued education even if they didn’t have much money themselves).

Since I started my “sabbatical” (still hate the r-word), I have done a lot of nothing. But I also took a part-time job in a bike shop, despite being a novice mechanic. I started writing and editing for a friend’s successful food blog (, despite not being much of a cook. But most importantly, I’ve done what I’ve wanted to do (while obeying Covid restrictions) and haven’t really had to worry about money. I pay a lot of attention to money, because that’s my nature. But I don’t worry about it, because I’ve done the work of imagining and planning and budgeting and saving to the point where it’s second nature.

I don’t know what I’m going to be doing a week from now, never mind 10 years. I may go back to full-time work (unlikely). I may decide to do nothing at all (also unlikely). But I am absolutely sure that now I have the freedom to do what I want to do. And if I what want to do changes, I have the tools to make that new dream a reality. I hope you can make your dream a reality, too. At Dollar Peak, we want to help.