Two school teachers who quit their jobs to travel the world after just 8 years reveal the hardest part of retiring before 30

Joe and Ali OlsonThe hardest part of retiring before 30 wasn’t the tight budget or pressure of a side hustle — it was the uncertainty of starting over.

Joe and Ali Olson are living their dream.

After just eight years in the workforce, the couple, both in their early 30s, were able to quit their jobs as public school teachers in August 2015, retire, and begin travelling the world — now with their 1-year-old daughter, Annabelle, in tow.

By living frugally and finding a good side hustle — in their case, real estate — the couple was able to achieve financial independence relatively quickly. After purchasing their Las Vegas home at a steep discount in 2007, they started scooping up rental properties for cheap, a result of the battered housing prices during the financial crisis. They lost money at first, but eventually the market flipped and they began to turn a profit.

But even as their net worth rose, they didn’t succumb to lifestyle inflation. The pair continued to save 75% of their income and resided in their 400-square-foot home.

Fifteen properties later, they were able to retire as millionaires and tackle new dreams: travelling the world and starting a family. (You can follow along with their travels on their blog, Adventuring Along.)

The hardest part of their journey didn’t have anything to do with living on a tight budget or running a side hustle while still working full-time, however. The most difficult thing about retiring before 30 was actually taking the plunge and quitting their jobs — and the uncertainty that came with it.

“It’s scary to jump into a life made up entirely of unknowns,” Ali told Business Insider. “Luckily, our families and social community were so supportive, and as teachers we knew there was always a job waiting for us somewhere if we wanted to head back to work.”

Retiring young with your whole life ahead of you is daunting. It means pushing out of your comfort zone and restructuring all of your routines.

“People will rightly point out there are so many unknown risks,” Joe says. “Health issues. Stock market gyrations. The fact that you are now responsible for your own time and entertainment, instead of your employer dictating the majority of your hours.”

But for the Olsons, the risk was worth the reward. As Joe explains:

“To early retire, you have to embrace the uncertainty. Yes, risks happen. They happen when you’re still working, too. Being flexible is key. Wanting to try new things. Being willing to tighten your belt and adjust your spending, if necessary. Realising that going back to work isn’t the worst thing in the world. Yes, it means your retirement ‘failed,’ but is going back for two years before quitting again (after enjoying a decade of freedom) any more of a failure than not pushing off retiring for years, and working way longer than necessary, out of fear of the uncertainty?”

That’s the thing: You can always go back to work and earn more, but you’ll never know if early retirement is the right choice unless you dive in and try it.

“A lot of people get the ‘one more year’ syndrome and delay retirement because of a fear of what’s out there post-career, away from the comfort of a steady paycheck,” Ali says. “But every year is one more year of your life you can’t get back.”

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