How anyone can take multiple career breaks to unlock adventure, advance their career, and find financial freedom

Retire Often

Why do we have to work for 40 years and only retire once? Why can’t we take occasional career breaks to focus on the other areas of life that matter: family, friends, adventure, rest, hobbies, our health, and achieving long-held dreams?

And what if there was a way of doing so that not only avoided financial or career downsides – but brought profound upsides?

Author Jillian Johnsrud has walked the walk – taking numerous mini retirements that have unlocked work-life balance and a more purposeful life, while also
helping rather than hindering her career thanks to simple steps and practical principles that anyone can follow.

She has coached hundreds of people to achieve the same, and in she shares everything you need to make the most of every season of life by retiring not once – but often.

looking for an expert in mini retirements?

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Looking for an expert on mini retirements and sabbaticals? Jillian became financially independent at age 32 despite having a modest income and raising 6 kids. Her and her husband have taken a dozen mini-retirements.

Reach out for news features, to be a podcast guest or speaking engagements.

See her features in Parents.com, Forbes or video featured in Market Watch and Yahoo.

Connect via Email jillianjohnsrud@gmail.com

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jl collins

You don’t need to read this book. The title should be enough to put the idea of mini-retirements in your head. I didn’t even have that back in the day, yet this is how I handled my career. I retired often, although I wasn’t smart enough to think of it in those terms.

For the most part, I loved working. I just didn’t want to do it all the time. So whenever I felt the need, I stepped away. Sometimes for a few months. Once for five years. Mostly it was my call, but there was that time my company kicked me to the curb and there I was.

But you should read this book, and boy howdy how I wish I’d had it back then. If I had, my mini-retirements (which, make no mistake, were great) could have been so much better. So much less stressful. So much more beneficial. Instead of wandering in the wilderness feeling lost, I would have had this map. I would have had Jillian at my metaphorical side, guiding and reassuring me as I made my way. But I didn’t. She hadn’t written this book yet. But now she has, and now she is here for you.

In these pages Jillian shares with us exactly how to do it. How to minimize the risk and maximize the benefits, and how to create a whole new world of experiences. My wilderness wandering was wonderful, and I am so glad I did it. But now Retire Often has blazed the trail, shows us where the quicksand lurks, and takes us to all the scenic overlooks, many of which I simply didn’t know were there.

For one thing, I would have better understood and more easily accepted the mixed emotions triggered by stepping away. The good, the bad, and the baffling. Make no mistake, taking mini-retirements is an exhilarating experience, but those emotions definitely can present challenges along with the thrills.

Learning how to recover from a stressful job with active rest and “un-rushing” (a concept I love!), and how to keep off the couch and free of the mind-numbing TV trap, are worth the read alone. But there is so much more.

Jillian lays out four steps:

• • From Dreams to Plans
  • Unexpected Career Benefits
  • Figure Out the Finances
  • Navigating the Mini-retirement Journey

In the first three, she shows us how to plan our journey, gear up, pack our knapsacks and bravely set out into our adventure. Step four is all about your compass and navigating your way into this undiscovered country.

For me, step three was always my strong suit. Investing and finance are in my wheelhouse. But looking back, the others were not.

Sadly, I never really did much dreaming or planning around my mini-retirements. Mostly I waited till I was burning out and then just pulled the trigger. Figuring out what came next, well, came next. While this mostly worked out, it didn’t always. But either way, as I read, I couldn’t help but wonder how much better each journey would have been with the kind of forethought in these pages. Being aware of what Jillian calls our “seasons of life” and, critically, that these carry expiration dates, would have made a huge difference in my approach.

Each time I did this it felt like I was putting my career in danger. The idea that there could actually be career benefits was stunning to me. Maybe it shouldn’t have been such an eyeopener. Looking back, stepping away never seemed to hurt my work or career. But it always felt like a risk and, while I was certainly willing to take it, the sense of unease was ever present.

Had I read Retire Often, I would have known about the almost magical force that helps pull you back into the workforce when you are ready (and sometimes before you are), and I would have learned how playing it well can propel you into even stronger and more lucrative positions.

Step Two would have made me far more effective in negotiating my departures and returns, opening up whole new potential avenues I never considered. It also would have made me better at crafting the stories around my taking this unconventional step, making employers more comfortable with and open to my eventual return. For example, here are two rules regarding creating stories I especially loved:

Rule One: Everything must be true. 

Rule Two: It can’t be the whole truth.

If these seem obvious, the details may surprise you.

Back in the day, I didn’t really bother with or even think about the guidance Jillian offers in Step Four. I simply had no awareness. But my journey would have been considerably more psychologically comfortable and understandable for me, and those around me, if I had. 

But that’s me. You are very likely different. Maybe for you the career benefits are glaringly obvious and it is the financial advice in Step Three that paves your way. Perhaps the whole idea will come as a revelation and Step One will open the floodgates of your dreams. Or some other combination. Maybe this whole concept and approach is going to be like walking out of a dense, damp fog into the bright warm sunlight. 

Regardless, I’ll wager you’ll be glad you picked up this book. Your life, your career, and your many coming retirements will be lastingly richer for it.

JL Collins, Author of The Simple Path to Wealth and Pathfinders 
February 2025