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

by Jillian Johnsrud

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 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 Retire Often she shares everything you need to make the most of every season of life by retiring not once – but often.

Genres: Nonfiction, Finance, Audiobook, Self Help, Personal Finance

288 pages, Paperback

Published September 9, 2025

About the author

Jillian has been slowly growing her creative and entrepreneurial life since she was a teenager. About once a month she realizes she's not cut out for this life and quits, but only for a few hours.

Her work has been featured in Forbes, Good Morning America, USA Today, Glamour, and Parents. Her work has been viewed over a million times with it's fair share of praise and criticism.

She is a popular podcast guest, speaker and coach. She runs an online education company teaching people how to create financial freedom while building meaningful and enjoyable lives.

Over the last 19 years of marriage, she and her husband, Adam, have adopted 4 kids, had 2 biological kids, traveled to 40+ of the United States and 27 more countries, lived abroad, bought and renovated homes, then became financially independent in their 30s.

Jillian and Adam live in Montana with their 5 kids and dog, Cheesy Taco. They spend their time reading, hiking, drinking tea, watching their ducks and traveling with their kids.

Reviews

[Laura · Rating 3 out of 5]

Thank you to Money with Katie for interviewing the author and leading me to this book. While the book is well written, its content is illogical for most professions and individuals. The theory is fantastic and if you can make it work and still jump back into the corporate bandwagon after (if you still want to) then I'm very happy for you. However, I don't see how this could be feasible for me. I appreciate that she gives examples but they too are just not applicable. I would suggest to integrate her suggestions into as long as vacations as you can get from your employer. Maybe you get 2, 3, 5 weeks off each year, if you can put them back to back then implement suggestions from this book to make the most of that time.

[J M · Rating 2 out of 5]

Very barebones personal finance book. Cute concept — not exactly practical in an age of constant layoffs and attrition. Author clearly endured some trauma in her life which gives her this “happy go lucky” mentality. I’ve never seen anyone who has purposely adopted 5 kids say “sometimes life just happens” so often. Anyways, kudos to those of you who can actually pull this off. Wouldn’t pick up again.

[Rachel Lucas Hough · Rating 5 out of 5]

Jillian’s work completely changed how I view retirement. Because of her, I took my own mini-retirement, and it was life-giving in ways I didn’t expect. Retire Often is encouraging, practical, and a reminder that you don’t have to wait until you're 65 to step back, rest, and reset.

[Sophia Khawly · Rating 5 out of 5]

Great book on how to take multiple mini retirements. I used to think I wanted to retire early, but after taking several mini retirements, it is no longer necessary.

[Alexandra · Rating 5 out of 5]

I've followed Jillian's work for over seven years, and her latest book, 'Retire Often,' is her most impactful yet.
Chapter 2, which dives into lifestyle design, was a standout for me. Jillian offers practical tools to help readers envision their ideal day, week, and year — from crafting a dream to-do list to reflecting deeply on what they truly want out of life. Her guidance feels both inspiring and actionable.
As a former HR Business Partner, I also appreciated her bold critique of traditional work culture. In Chapter 12, she challenges the status quo by suggesting that employers give employees a month off every year — a radical idea that feels surprisingly reasonable once she lays out the case.
The book is highly readable from start to finish, but it also works well as a reference guide, especially when planning specific phases of a sabbatical or mini-retirement. I only wish 'Retire Often' had been around when I took my own career break — it would have helped me approach that time with far more confidence and intentionality.

[Lore H · Rating 3 out of 5]

three stars because I liked the idea and execution of this book, but didn’t love it. you can tell this is a topic the author is passionate about and has lived experience navigating. however, the audiobook felt a bit repetitive to me. I would have preferred a shorter guide with fewer anecdotes, or a memoir focusing more in depth on her life stories. I particularly appreciated the chapter that summarized health insurance options for its practical application. An interesting psychological phenomenon that I hadn’t thought much about before reading this book is how folks feel an urge to “help” folks in mini retirement by sending them job opportunities, even when they may not be actively searching. The author says this is often due to our own discomfort towards people who stray from the beaten path, and our natural desire to want to support them. After reading this book, I’m not personally convinced that mini retirement(s) is the path for me, but I think this book is still a valuable resource for those considering and planning for this specific goal.

[S.A. Klopfenstein · Rating 4 out of 5]

Listened to Jillian a few months ago on a FI podcast, and really enjoyed her perspective, and heard several folks on other podcasts mention this book as a good follow-up to Die With Zero, which I would agree with.

All may not be able to replicate her exact approach, but it's worth the read to think about how you might re-think retirement and make sabbaticals (or something similar) a part of your journey along the way.

I really like the concept of spreading out experiences throughout your life. But for the book itself, I felt like the strongest parts were more personal and philosophical, though much of the book was on the practical side. These sections (like way too many chapters about how to negotiate time off and talk to concerned friends about what you're doing) slipped into the weeds for me.

Still really liked the book, overall.

[Kateryna Maw · Rating 4 out of 5]

The premise of the book is great and I enjoy the author's podcast. But somehow the book felt uninspiring and flat to the premise preached. I believe people can set goals to take mini-rerirements, financially-speaking, but also, find time to do it. I think that the structure described in the book does help but I also felt as though it was written poorly. I wish there were other, better, books about this topic that are inspiring to leap! On the other hand, I appreciated that the book was not all about travel. I agreed with the author that we often ignore the mess in the house that can not be dealt with during nights and weekends, so that mini-retirements are not always about luxury trips to Europe but also time to declutter and make time for the projects that have been neglected.

[Jean M · Rating 3 out of 5]

After taking a retirement course, looking ahead, I began thinking about what I want with the next portion of my life. I went looking for books, and this is one of the books that found me.

Great idea worth hearing early in life, about how you craft your life around the experiences you want. I paired this book with the audiobook Die with Zero by Bill Perkins and was blown away at the synergy and messages. It's really helping me see different and consider other paths. As with many self-help topics, I wish I knew this earlier in life.

I highly suggest for anyone who doesn't see making money as the end all be all of life. Take what you can from the lessons and decide for yourself how YOU want to live your life.

(Shout out to Die With Zero - Bill Perkins)

[Fritz Gilbert · Rating 5 out of 5]

If you've ever considered taking a sabbatical, this book is for you.

Jillian draws a beautiful map, based on her personal experience and coaching clients, to lead you down the path that many thought impossible. Rather than wait until 65 to retire, sprinkle regular "mini-retirements" throughout your life at key points (e.g., before the kids leave home). Avoid future regret, and live your best life now.

Many people dismiss this alternative approach, but this book shows that its possible, and lays out all of the steps to make it a reality in your life. A "must-read" if you're curious about a new way of living, and a trend that is gaining steam.

[Katy Aoyagi · Rating 3 out of 5]

Time off from the work force can go by many names: sabbatical, career break, mini-retirement, hiatus...

As I am currently on a mini-break, I picked up this book to gain some insight on how others go about this often weird time of limbo. Some go balls to the wall and keep the workforce momentum going with super busy schedules and others may go the entirely opposite route with lots of periods of rest. I'm probably somewhere in the middle ... trying to get logistical stuff done while also tending to my health and listening to my body when I need rest and down time.

The audiobook was alright, albeit a bit repetitive.

⭐️⭐️⭐️

[Brandon Lee · Rating 3 out of 5]

A little wordier than necessary but makes up for it with some good anecdotes and real-life stories. Essentially a checklist of things to consider and plan for, with elaborations. Some of it you probably won’t need to be told, but the financial section is a little underweight and further reading will likely be required. As with many of these books, very U.S.-centric with their wacky taxes and healthcare rules. Mostly useful advice, although I enjoyed figuring out a lot of this stuff for myself when I took a sabbatical!

[Elizabeth Burton, LCSW, PMH-C · Rating 3 out of 5]

Overall, Jillian offers some beautiful and compelling ideas that do help reassess how to save and how to live for both security and freedom. At the same time, I had a lot of tension knowing that despite the title this isn’t for anyone. Over the majority of Americans live paycheck to paycheck, the concepts feel aspirational in a way that isn’t practically accessible for most. The overall philosophy feels tailored to a specific socioeconomic class (people with financial cushions and flexible careers). For those without that privilege, it may feel unrealistic and discouraging.

[Sarah · Rating 5 out of 5]

Inspiring read. This book provides a solution to one of (my) life’s biggest problems: the feeling of being stuck in a job or locked into a career path with no end in sight for decades and not having time to do what brings me joy. It could be more feasible than you think to take a break. I’m on a break now and this book made me feel more empowered to return to work in the future with a roadmap for how I can continue taking mini retirements throughout my career. Recommend!

[Frieda Sewald Weigle · Rating 4 out of 5]

An great book that invites the reader to explore the ideas of mini-retirements and how to accomplish this goal both emotionally and financially. It provides the framework for making this a regular part of your life. Both pros and cons are presented in this book, which adds to the books value. A must-read for those who are experiencing burnout and mental health challenges.

[socerangel86 · Rating 5 out of 5]

Great book with a different perspective on life. It makes no sense (unless financially needed) to only retire when you’re older. But it is a total mindset shift. I love the idea of taking time off to knock out a project (you know those can linger). Lots of innovative concepts. A great read (even if you don’t think you want to retire often).

[Tim Mathis · Rating 5 out of 5]

I really enjoyed the practicality and philosophy behind the book. Super useful and I feel like the author is a kindred spirit. Would recommend to anyone looking to take control of their life back from work and/or an unreasonable sense of responsibility to accumulate.

[Josh Overmyer · Rating 5 out of 5]

Jillian has been an invaluable resource for me as I planned and then have taken my own Mini-Retirement. I love this concise collection of her best stories and examples from her career coaching others and the guests on her podcast.

[Margaret · Rating 2 out of 5]

Admittedly I didn’t go into this very open because I heard the author on a personal finance podcast and was doubtful of its applicability to my life and I still feel that but it’s a nice thing that maybe I’ll eventually try for :/

[Jon · Rating 3 out of 5]

Decent book to rethink stretching our breaks in careers, life etc and budget effectively to do so. Sabbaticals and pushing the limits to not work just to retire but making vacations into normal annual life is good to look at

[Kim · Rating 4 out of 5]

I like the concept and agree with much of it. Some of the approach seems overly positive and “what could go wrong?” While other parts have practical insights and some ways to approach taking mini retirements or sabbaticals.

[Rachel · Rating 4 out of 5]

Very interesting perspectives. My favorite section was the last one which felt the most practical with real struggles of people who had done this before.

I wish the author discussed opportunity cost more as well. Overall good read. Would recommend.

[JL Kegley · Rating 5 out of 5]

Taking breaks from work made easy!

Easy and fun read.

[Zachary Blake · Rating 5 out of 5]

This was a great read and would be helpful in a different phase of life. I will hopefully be returning to this book soon.

[Ashley · Rating 5 out of 5]

This book is my new personality.

[Chris · Rating 3 out of 5]

Great concept, but maybe a little lacking.

[Jamie Hatcher]

Love the idea and am trying to implement it!

[M · Rating 3 out of 5]

Audiobook. I love and agree with the premise of the book but it didn’t need to be that long.

[Sarah Beadle · Rating 4 out of 5]

A very interesting concept, made me think in a new way. I really enjoyed this!

[Hannah · Rating 5 out of 5]

Jillian Johnsrud is a good one. I really enjoy her podcast about mini-retirements and I love how down to earth she is about sharing logistics for making big career changes work.