We quit our jobs and gave up the golden handcuffs try a 'first retirement' in our 30s, have no regrets

We'd been thriving in Seattle's tech boom — Bianca, in the US on a work visa, was a senior finance reporter at Business Insider covering how Wall Street's biggest firms use and invest in technology, and Charlie, a software engineer within Amazon's payments organization, had spent eight years working toward a principal-engineer role.

We had what people like to call golden handcuffs: good salaries, rising careers, and a sense that if we just kept working hard, we'd likely keep making more money. The handcuffs weren't all that tight, either; they were actually pretty comfortable.

But for us, quitting our jobs and taking time away from work was a constant if far-off dream. When immigration concerns made our international travel commitments uncertain, we decided not to postpone our dream any longer — and started to look at the numbers.

For years, we had saved and invested traditionally: 401(k)s, an apartment that would hopefully appreciate and provide a nest egg for a family home, and some riskier exposure to the stock and bond markets. To leave our jobs, we'd have to figure out how to balance spending during our break without blowing the financial future we'd spent years building.

So we did the thing that makes almost every big life decision feel slightly less terrifying: We put together a spreadsheet. We pegged dollar figures for daily spend, travel, and the boat. Even though they were rough, and there was a sense that the estimates could prove to be way off, putting it down in front of us made it feel real. It also gave us an opportunity to get comfortable with the level of savings we could expect to draw down.

By June 2025, we'd both quit our jobs, sold our Seattle condo, and bought a 42-foot sailboat, Windsong, beginning what we now call our "first retirement." Almost a year and a half later, we and our dog, Stella, have sailed well over 1,000 miles around the Pacific Northwest, traveled to a dozen countries, and committed more meaningful time towards our families and hobbies.

As it turns out, for us, the hardest part about quitting lucrative jobs wasn't financial planning for a year and a half without a paycheck. It was getting comfortable with the uncertainty, risk and likely impact on our "final retirement" down the road.

With a bit of budgeting, asset-rearranging, and confidence in ourselves and each other, we were able to make quitting feel like less of a reckless leap and more like a calculated bet on ourselves. For anyone considering such a plan, here's how we did it.

Our budget's main expenses would be daily living costs, multiple international trips, the purchase of a sailboat big enough to live on for months at a time, and the unpredictable costs of boat ownership (especially unpredictable for us since we'd never owned a boat before).

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Until this point, we'd been pretty financially conservative and risk-averse people. We earmarked a portion of our savings we were comfortable saying goodbye to — in return for our travel, boat purchase, and daily living expenses.

This mostly came from Amazon common shares that comprised the majority of Charlie's compensation and some certificates of deposits that were growing modestly. By diversifying our savings throughout the past eight years, we were able to retain brokerage accounts and 401(k)s, so that we wouldn't be starting from zero on the backend of our first retirement. It worked out that to achieve our personal goals for this time off work, we would be preparing to spend 10% to 20% of our savings.