Retire Often

In this conversation, Brooke Thayer shares her experiences with taking multiple mini retirements and traveling the world. She discusses the inspiration behind her mini retirements, including a difficult divorce that led her to reevaluate her life. Brooke shares the challenges and benefits of open-ended travel, staying in hostels, and finding connections in the travel community. She also talks about the financial aspects of long-term travel and offers tips for affordable travel. Brooke highlights the importance of transitioning from saving to spending mode and gaining agency in making personal choices. Overall, her story serves as an encouragement for those looking to reimagine their lives and pursue their travel dreams. Takeaways Taking mini retirements and traveling can be a transformative experience, providing opportunities for personal growth, self-discovery, and reimagining life. Open-ended travel allows for flexibility and the freedom to explore new destinations and experiences. Staying in hostels and utilizing budget-friendly accommodations can make long-term travel more affordable. Transitioning from saving to spending mode can be challenging, but having a budget and financial plan in place can help maintain financial stability. Taking the leap to pursue your travel dreams requires courage and a willingness to step out of your comfort zone.

Brent and his wife were on the path to financial independence, planning to retire early at 40. However, they realized that their plan wasn't serving them well and decided to take a mini-retirement. The challenges of asking for unpaid leave and shifting from saving to spending were overcome by their desire for change. Brent's mini-retirement involved a two-month road trip with his wife and eight-month-old son, inspired by Canadian hero Terry Fox. The trip had its challenges, but it allowed Brent to fully enjoy time with his family and sparked a desire for a more flexible and lifestyle-friendly career. The mini retirement provided the space for Brent to reimagine his path to financial independence and prioritize quality time with his family. He now embraces the idea of retiring often and being open to different seasons of work and rest. Brent encourages others to take the leap and try something new to get unstuck and gain clarity.

Diania shares her experience of negotiating a mini-retirement to walk the Camino de Santiago in Spain. She initially planned to support her uncle on the journey but ended up going alone. Diania discusses the financial preparation she made, including paying off debt and learning about financial independence. The time off was full of self-discovery and awareness, including recognizing her weak internal compass and susceptibility to external influences. She emphasized the importance of community and in-person connections, which led her to create the Economy Conference. She is a great example of how to negotiate a leave of absence and how time brought her closer to financial independence.

In this episode, we accompany Cosmin on his remarkable journey from the brink of burnout in his career to embracing a life of nomadic adventure. After years of high-intensity work, he took his first month-long mini-retirement. Cosmin returned with a new perspective: continue on a path of stress and exhaustion or forge a new way of living. He chose the latter, setting off on an inspiring journey of self-discovery and global exploration. Cosmin shares the challenges and triumphs of transitioning to nomadism, the insights gained from diverse cultures, and how he redefined his notions of success and happiness. His story is a compelling testament to the transformative power of breaking free from societal norms and choosing a life filled with travel, exploration, and personal growth.

In this conversation with Darlene, we delve deep into the journey of early retirement and the surprises it holds beyond the workplace. Darlene's story goes from her demanding corporate career to a retirement decision spurred by an enticing severance package. This episode is not just about the transition into early retirement; it's about the unexpected emotional roller coaster that followed. Darlene candidly shares the challenges of filling days once packed with responsibilities, the struggles of maintaining friendships outside the office, and the enlightening process of rediscovering her passions. She discusses her initial forays into entrepreneurship and volunteering, providing an honest look at the quest to redefine purpose. Through this discussion, we explore the idea that retirement isn't an end but a complex beginning, offering insights on how to prepare for its profound changes. Darlene opens up about the initial post-retirement travels, the subsequent feelings of loss of identity, and the proactive steps she took to rebuild a fulfilling life. She touches on the importance of community, the impact of proximity principle post-retirement, and the innovative approach of taking 'mini non-retirements' to maintain a sense of purpose. Darlene's journey encourages us to look beyond the numbers and to anticipate the emotional aspects of retiring not just early, but well.

In this conversation with my friend, JL Collins, we take a look at a professional journey that defies convention, punctuated by career breaks and the power of 'F.U. money.' His career began marked by intense work periods that eventually led to inevitable burnout. But through these experiences, JL began taking mini-retirements, illustrating that stepping away can often add more meaning in life. This episode isn’t just a look into JL's path of financial independence; it explores his philosophical pivot from earner to explorer. We chart his transition from a traditional careerist to an unconventional path, where extended travel and periods of freedom became the norm. JL unveils the strategies that enabled his shift towards a life less ordinary. He doesn't just share tales of his travels; he provides a thoughtful perspective on redefining success, the value of time over money, and how to wisely navigate the financial tides to craft your own path of liberty and discovery.

In college, Joe fell in love with hiking and climbing. He loved the community and time in nature. He tried pursuing a corporate life, but a mini-retirement where he hiked the Appalachian Trail shifted his path. He realized that corporate life wasn’t how he wanted to spend the rest of his life. But he also wasn’t drawn to the “dirt bag” life of taking odd jobs to pay the bills between adventures. So he rapidly saved money from the corporate job to pursue financial independence. After taking another long mini-retirement to hike the Pacific Crest Trail, he made an even more significant life shift.

Getting diagnosed with a brain tumor during her residency helped Dawn refocus on who she wanted to be as a person and what she wanted her life to look like. Instead of losing herself in her profession, she consistently course corrected by using mini-retirements. The medical profession, like many others, can become an all consuming identity. Instead of accepting the prescribed narrative to what her life should look like based on her job, Dawn carved out a whole new path.

Eric was a schoolteacher in Boston. Along with his wife and two kids, they moved to France for two years. This seems like an impossible step for many people. But it was after years of practice taking smaller trips and spending time abroad. His wife is originally from France, and she used that time to complete a master's program. Eric shares the financials behind a massive move like this, showing how much more affordable France was than their life in Boston. His story shows how much can happen in life when you create some space for new things.

Stepping away from a successful, lucrative, and important job can be tricky. Even when that job is eating up all your free time and bandwidth and at the cost of your health and relationships. It’s scary to kill the golden goose. But Amanda discovered all that life had to offer on the other side during her mini-retirement. Surprisingly, the lower stress and more free time even helped their finances. This mini-retirement created a huge opportunity for growth as a mom and wife. Plus it gave her new skills that might be a future business. She had a hard time imagining ever leaving her career, but now she and her wife are planning for a life full of travel and adventure.

Vikaash has always been good at work. Professionally, success came quickly. From Harvard Business School to 40 Under Forty Young Business Leaders award by CNBC, to CEO. But that type of success has a cost: 15 to 18-hour work days and little time or energy left over for family, health, sleep, or hobbies. At the peak of his career, he decided to take a mini-retirement. What I find incredible about Vikaash is the vision and courage to take this step. I’ve known a lot of successful professionals, and stepping away from the thing they do best, in order to focus on areas of their life that need attention is not common. There is too much ego and fear and unwillingness to lean into the discomfort. Vikaash shares about the motivation to make that change and the challenges along the way. Plus he’s leaning into being the best father and husband he can while finally getting enough sleep and exercise. The great thing about a professional half-time is that it allows you to regroup, refocus, and refresh. He probably won’t go back to 18-hour work days. But this next chapter might be even more impactful professionally. He can leverage his expertise and skill set in new ways that support the lifestyle changes he’s been making progress on. I’m sure his most impressive professional accomplishments are yet to come.

Jamie and her husband are both self-employed. Walking away from their business for a month seemed overwhelming. But they desperately needed to rest, recover, and focus on family, health, and fun for a bit. Jamie shares how they planned and prepared for that first month off. It was so good for everyone that they knew they wanted to do it again. Now, after their second mini-retirement, they are figuring out how to create more passive income to fund a yearly mini-retirement. They are organizing their work, home, and lives to be able to Retire Often.

Chad (Coach Carson) started his financial journey by investing in real estate. It helped fund his and his wife's first budget mini-retirement. Over the years, as his rentals became more profitable, he was able to upgrade the mini-retirement adventures as well. He is just finishing his third mini-retirement, a year-long trip to Spain with his family. Chad gives practical and encouraging advice on how being a small real estate investor can give you even more financial freedom. Just a few rentals can fund your Retire Often lifestyle. His new book, The Small and Mighty Real Estate Investor is out now. https://amzn.to/3OLykyl

In her mid 30’s, Rachel decided it was time for a change. She had been working 10 hours a day, 6 or 7 days a week, stressed about even asking for a day off. She was ready for a change of pace and autonomy over her life. Despite never being a hiker and never even traveling outside of the country, she began preparing for a 500-mile pilgrimage in Spain. Her two-month mini-retirement plan expanded into a year, as she finally started working on a business idea she had been dreaming about for years. Old beliefs around work and money arose as she started spending down her savings. But this mini-retirement allowed her to focus on her personal growth that she can carry forward as she returns to work.

Growing up in Mexico, Angel never expected to travel the world. If he did well financially, there was an expectation of simply buying nicer stuff. During his 20's, he took an open ended trip to Southeast Asia, assuming this was his one chance. That trip shifted his perspective and changed the course of his life. He came back knowing he wanted to be different and live differently. After his baby was born, he and his new wife, set off on a year long adventure. Angel shares how that first trip helped him grow into someone ready to be a husband and father. He explains how different the first solo trip was from planning to travel with a spouse and baby. You'll see how the first mini-retirement set him on a path to be able to do it again.