We Quit Our Jobs to Take a First Retirement From a Sailboat

‘… Or we could just quit our jobs and do whatever we want.’

The first time it came up, it was more of a joke than anything. We were sitting together in the living room of our downtown Seattle apartment in April 2025, watching boat traffic on Lake Union, when Charlie suggested it.

We were looking for options. Bianca was in the US on a work visa, and for weeks our worried families in Canada had been sending us news stories of US visa holders and tourists getting arrested at border crossings and enduring weekslong detentions.

At first we casually shrugged it off, but as the news stories kept coming, we became less certain. Ultimately, our immigration lawyers advised Bianca not to leave the country for the foreseeable future.

We took their advice in stride and continued to plug away at our jobs.

We were making the most of Seattle’s tech boom, but wanted something else

Bianca was a senior finance reporter at Business Insider. What had once been a specialized beat — how Wall Street’s biggest firms use and invest in technology — had exploded in popularity as AI became one of the hottest topics in the economy.

Charlie was a software engineer within Amazon’s payments organization. He had joined as a new college hire, but eight years later was on his way to becoming a principal engineer. He was then leading multiple engineering teams responsible for most of Amazon’s buy-now, pay-later businesses in the US and Canada.

Not surprisingly, succeeding in our corporate jobs required an intense commitment, and we always felt it came at the cost of other pursuits, like artistic hobbies and longer, more immersive trips to see the world. We’d discussed finding work that would allow for more flexibility in our schedule and lifestyle, but had always chosen new work opportunities, which often came with generous paychecks and bonuses.

By early April, we felt we had to choose between staying in the US indefinitely or ignoring our lawyers and taking a risk at the border each time we re-entered. Facing that decision prompted us to think about our lives in a much bigger way, and eventually we began to consider leaving the US entirely.

We decided to buy a sailboat and travel

We’d moved to Seattle in 2017. Like many recently minted Seattleites and many of our friends, the Emerald City drew us in because of the surplus of tech jobs. Meaningful yearly raises and an ever-rising Amazon share price made saving easy — while still taking yearly trips to Europe, buying NHL hockey tickets on a whim, and staying up-to-date with Seattle’s growing restaurant scene.

That’s why, at first, we laughed off the idea of leaving those jobs. But as we imagined more and more glimpses of a life temporarily unemployed, the idea began to take root in our minds.

Since convincing Bianca to take a beginner’s sailing course together a few years prior, Charlie had been moving deeper into the world of sailing on his own. What started as a way to be outside during the pandemic was turning into something more; by 2024, Charlie was flying down to San Francisco a few times a year to take advanced sailing clinics and had connected with a boat broker. As we considered buying one, we searched for ways to extend the limited time we could spend on a boat each year. Taking a break from work could solve this.

There were other factors: We had more tentative travel plans than vacation days remaining, including three weddings that we didn’t want to miss. Something would have to give.

After about a month, the conversations went from What we should do? to How we should do it? A few weeks later, in May, we quit our jobs and entered our “first retirement” at age 30.

Sorting out the financial tradeoffs was key to making the decision

We’ve always been very financially conservative and knew we wanted to be debt-free during “retirement,” so we took a hard look at our finances first.

The budget accounted for known costs like our everyday living expenses and travel. We then worked-in unpredictable costs like the surprise maintenance items that every boat owner learns to fear. The final piece was ensuring we’d have enough money left over for our life post-retirement.

After verifying our estimates were reasonable, we ran the numbers and saw (with relief) that it could work — but we would have to make some meaningful lifestyle changes.

We sold our Seattle condo rather than rent it at a loss, despite a tough housing market. To keep costs down, we decided we’d stay with family when we weren’t traveling or on the boat, knowing it would be a temporary but necessary tradeoff.

We worried about the long-term impact to our careers

Beyond the financial considerations we had to sort out, we examined the risks and sacrifices. In today’s market, what would be the consequence of having a blank time period on our résumés? And what would returning to work in our respective fields even look like with the rise of AI and AI-related layoffs?

We began to prepare for workplace conversations with our teams and managers. Key to us was leaving on good terms. We gave the appropriate amount of notice (three and four weeks, respectively) and made sure to set up meetings with coworkers we liked and respected, including those who’d moved on from our direct teams. Colleagues expressed jealousy, managers told us we were brave, and Bianca’s industry sources were so interested they gave her their personal cell numbers to send photos from the boat.

In addition to prepping for difficult conversations at work, we also discussed the fun stuff. We drilled down into what we hoped to accomplish from time off and why it spoke to us. Fleshing out this side deeply was important for us to ensure we were leaving for the right reasons.

Though there are sacrifices, this ‘first retirement’ feels like one of the best decisions of our lives

Twelve months in, some of these goals have started to come to fruition.

With our dog, we’ve cruised over 1,000 miles along the Pacific Northwest coastline in our 42-foot sailboat, Windsong. We’ve traveled to places we’ve always wanted to go (to see Tokyo in springtime bloom and eat a delicious bowl of noodles streetside in Ho Chi Minh) and have discovered new ways to see the world (scuba diving in French Polynesia and getting scuba certified in Mexico).

We’ve also taken some spontaneous trips — cruising in the Bahamas, climbing Utah’s iconic red rocks, wandering Istanbul’s steep and winding streets — thanks to our newfound sense of being able to say, Why not?

Back at home, we’ve spent more time with our immediate families than we have in years. Bianca has learned to play her first instrument, bass guitar, and we get to jam for hours on end. Charlie is slowly becoming an amateur electrician, mechanic, and plumber, thanks to necessary repairs that have popped up on the boat.

Beyond these concrete pursuits, there have been lifestyle benefits. We’re less stressed and better rested, which has had some mental-health benefits. Being more active has quieted nagging injuries.

Some of these outcomes were expected, some unexpected, but we think they only materialized because we gave them the space to flourish.

So, what’s next?

This first retirement began as a break, but we want it to be more than that. We’re now seriously considering how to incorporate some of our lifestyle changes into our working life.

We’re increasingly open to pivoting careers entirely — trying our hand at freelance work or small business ownership. We hope to be working in some capacity by the new year and have started meandering through businesses for sale on the West Coast. We know we may fail and need to try and go back to a corporate gig, and are aware of the downturn the labor market has taken.

That said, up to this point we haven’t allowed ourselves to think too seriously about what kind of work we want to do on the back end of this year. What would be the point to step away from the restraints of current-work, only to worry about challenges of securing future-work?

Got a career story to share? Contact this editor, Debbie Strong, at dstrong@businessinsider.com.