Retire Early, Retire Often

A few months ago, a friend told me something that shook my world: He was retiring. 

“That’s awesome,” I said. But in my brain, I was thinking, Why would you retire now? You’re only 58!

He explained that he had the financial security to make it happen, and he didn’t want to be one of those people who died in his job. Sure, he wanted to pick up some consulting gigs or project work, but he was done with the stress that came from the full-time job.

Two emotions were boxing in my 54-year-old brain: In one corner, there was envy that he had the ability and courage to step away. In the other, there was a quiet confidence, knowing that I’m happy with my work and have no burning drive to stop.

I suspect a lot of men feel similarly — there are things I love about my job, a bunch I like, and some parts that I’m into the same way I’m into smoke alarm batteries wailing for replacement at 3 a.m. It’s like being stopped at an intersection with one foot on the gas and one foot on the brake. You want to speed up to a life with fewer responsibilities and more fun, but you’re also in no hurry to leave the career you’ve spent a lifetime working toward.

So how can we have it all, both the cake (a satisfying job) and the icing (the freedom to play whenever the hell we want)? I reached out to the experts for guidance. Here are four options to help you construct a retirement plan that’s not all or nothing.

Option 1: The Part-Time Plan

What it is: Scale back to part time, but work well into your 70s. After all, stopping completely in your early 60s is a long time to “be on vacation” with longer life expectancies, says Steve Vernon, president of Rest-of-Life Communications, who’s published six books on retirement planning.

Is it right for you: Only if you really love your job. Fifty-four percent of people who keep working into their 70s do it because they want to work, while just 17 percent do it for the money, according to a 2009 Pew study.

Option 2: The Side Hustle Transition

What it is: Start part-time work now in a new field, and transition that into your home-stretch full-time job. This also gives you a chance to see what you like before you step down from your full-time job, says retirement coach Sara Zeff Geber, author of Essential Retirement Planning for Solo Agers.

Is it right for you: If you love new challenges and don’t mind becoming an absolute beginner again, then absolutely. Eighty-two percent of people reported successfully transitioning to a new career after age 45, according to a 2015 American Institute for Economic Research study.

Option 3: The Gig Life

What it is: Give up full-time for consulting and projects, to reframe your skill set into other avenues of work — without the ties and obligations of a full-time job. “I know doctors who have become expert witnesses,” says Franz Gilbert, founder and author of The Retirement Manifesto.

Is it right for you: Only if your retirement case is strong. It can be stressful to hustle for new gigs at that age if you don’t have some financial cushioning.

Option 4: The Step-Down

What it is: Take extended vacations or sabbaticals, or work with your employer to create a lesser role with less responsibility. The most effective way to retire early can be to do your current job in more flexible ways, rather than finding something completely new, says Nancy Collamer, founder of MyLifestyleCareer.com and author of Second-Act Careers.

Is it right for you:  Not just the most doable, but the option with the best balance between play time and fulfilling work. A 2022 study from the Netherlands found that gradual retirees had more vitality overall. So there’s not just more free time for living, but you’ve got the energy to enjoy it.