Retire Often

In this solo episode, Jillian discusses the necessity of taking mini retirements to engage in meaningful activities that have expiration dates, such as family adventures. Jillian reflects on her own experiences and the unpredictability of life, encouraging listeners to prioritize these moments before they pass by. Takeaways Mini retirements allow for experiences that can't fit into weekends Some life experiences have expiration dates that can't be postponed until 65 Life is unpredictable, and we should seize opportunities when they arise Regrets often stem from not taking chances when we had the time The joy of experiences can outweigh the hassle of planning them As we age, our preferences and abilities change, impacting our adventures  

Jacob Wade shares his transformative journey from a high-stress tech sales job to a life of travel and family connection through a mini retirement. He discusses the mental health challenges that led to his decision, the planning and execution of a year-long RV trip with his family, and the profound impact it had on their lives. Jacob reflects on the shift from a corporate career to entrepreneurship, emphasizing the importance of embracing risk and prioritizing personal fulfillment over financial metrics.   Takeaways   Jacob experienced a mental breakdown due to work stress and travel demands. Jacob's journey highlights the importance of mental health and family connection. He realized he didn't need to reach a financial finish line to make life changes. The FIRE movement can create a mindset that limits freedom vs create it.  He learned that life is about the journey, not just financial goals. The risk of staying in a job you hate can be greater than the risk of change.   Follow and Connect with Jacob:   YouTube.com/@Roadmapmoney Instagram.com/@roadmapmoney threads.net/@roadmapmoney

In this conversation, Stacy shares her experiences part way through her mini retirements. She shares how she created distinct phases. While explaining the importance of having a structured yet flexible approach to this career break. We cover how she overcame one more year syndrome and the fear of losing out on that extra income.  Takeaways She felt the need for a better work-life balance due to her stressful job. The group coaching provided valuable support and perspective. Hesitations about leaving a stable career are common but manageable. Volunteering unexpectedly became a fulfilling part of her journey. Flexibility in planning is crucial for a successful mini retirement. Prioritizing rest before tackling new challenges is beneficial. Calculating financial implications helped Stacy make informed decisions.

In this episode, I explain that a month is an ideal starting point due to the ease of negotiation, lower costs, the ability to achieve significant personal goals, and the chance to practice for longer breaks. The conversation then moves into strategies for negotiating time off, emphasizing the importance of a collaborative approach and the recognition that negotiation is often a multi-step process. I then detail the importance of crafting a compelling narrative when negotiating a mini-retirement. She outlines four key elements for framing the story: it should be positive, interesting, specific, and ideally a one-time event. Throughout the discussion, she offers practical strategies for framing the conversation, addressing challenges, and using compromise to create a win-win situation for both employee and employer. You can request access to the 2 free resources to plan an incredible 1-month mini-retirement at http://retireoften.com/onemonth

In this conversation, Jillian speaks with Ken and Mary from The Humble Penny about their journey of taking mini-retirements as business owners. They discuss the impact of COVID on their work-life balance, the transition from corporate jobs to entrepreneurship, and the importance of building systems that allow for freedom in their business. They share insights on the creative energy that comes from taking breaks, the dynamics of family life as business owners, and the mindset shifts necessary for success.  TakeawaysL COVID prompted a reassessment of priorities and the desire for more autonomy Transitioning from corporate to business ownership requires discipline and organization Building systems and having a supportive team is crucial for taking breaks It took Ken and Mary four years to achieve the freedom they desired in their business Taking breaks allows for rejuvenation and clearer vision in business Starting with systems in place can prevent overwhelm later on

In this solo episode, Jillian Johnsrud covers one of the tools that she uses with her coaching clients, focusing on the dual skills of courage for change and the capacity to stay and suffer. She emphasizes the importance of developing both skills to navigate life transitions effectively. Jillian provides actionable steps for listeners to clarify their goals and take necessary actions towards change, while also highlighting the significance of building resilience for future challenges.

Frances Benjamin shares her mini-retirement story and the transformative impact it had on her life. Before her mini-retirement, Frances was working multiple jobs and juggling the responsibilities of being a single mom. The catalyst for her decision to take a break was the pandemic and the realization that her daughter would soon be leaving the nest. Frances prepared for her mini-retirement by decluttering, saving money, and paying off debt. She embarked on her break with her daughter, traveling to Mexico and Thailand, immersing themselves in the local culture and enjoying the freedom to do what brought them joy.    Unexpectedly, Frances had to return home due to a family emergency, but this experience brought her closer to her father and reinforced the importance of prioritizing family. The mini-retirement allowed Frances to shift her mindset about work, putting herself and her family first. She now values her own well-being and is more selective about the commitments she takes on. Frances encourages other women to take breaks and prioritize their own happiness.   Takeaways   Taking a mini retirement can be a transformative experience, allowing individuals to prioritize their own happiness and well-being. Family emergencies can disrupt a mini-retirement, but they can also bring family members closer together. A mini-retirement can lead to a shift in mindset about work, with individuals valuing their own well-being and prioritizing family. Frances Links: Ask Me Anything 1:1 Career Break Coaching Tools & Resources

PT, is the creator of a large event, FinCon. Taking a mini-retirement as a business owner can be stressful, confusing, and scary. PT shares his experience of taking a step back from his business and how he slowly extracted himself while empowering his team. He discusses the challenges and transformations he went through during his mini-retirement, including finding new hobbies, spending more time with family, and healing emotionally and spiritually. PT also talks about the expansion of his business after his return, including acquiring another conference and taking over his family's CPA firm. He encourages entrepreneurs to prepare financially, trust their team, and be open to the possibility of a mini-retirement. PT Links: PT Money blog: https://ptmoney.com FinCon Expo: https://finconexpo.com TravelCon: https://travelcon.org CPA Firm: https://taylorassociatescpa.com Takeaways: Taking a step back from your business can be transformative and healing. Preparing financially and having a trusted team in place can make the process smoother. Mini-retirements can open up new opportunities and allow for massive business growth. Being open to new hobbies and experiences can lead to unexpected passions and connections. Entrepreneurs should consider the possibility of a mini-retirement and plan accordingly.

If you have ever been curious about taking an epic yearlong road trip, Heidi’s story of how her and her family embarked on a year-long mini-retirement traveling all around the US, will inspire you and give you practical tips for planning. They took an intentional break from work and school, with no W2 jobs and no traditional schooling for their three kids. They experimented with different experiences to prepare, such as traveling in Hawaii for three weeks and renting an RV. These experiments helped them make decisions and prepare for their mini-retirement.    They saved enough money to travel for a year, but ended up extending their trip to 15 months. They budgeted for $70,000 to $90,000 but ended up spending around $60,000. (Heidi mentions they spent $45,000 during the interview but let me know it was close to $60,000) They were surprised by how well they got along and how close they became as a family during their adventure.   Takeaways   Link to Heidi’s additional resources: https://ordinarysherpa.com/lifestyle Taking a mini-retirement or family gap year can be a meaningful and impactful experience. Experimenting with different experiences can help in making decisions and preparing for a mini-retirement. Budgeting and saving enough money is important, but it's also important to be flexible and open to unexpected opportunities. Finding joy in everyday novelty and valuing different types of experiences can enhance the mini-retirement experience. Spending quality time together as a family can strengthen relationships and create lasting memories.  

Dr. Corey Allen and his wife embarked on a month-long mini-retirement, traveling in an RV and exploring national parks. The idea originated in 2010 when they considered taking their kids out of school and traveling full-time. However, they decided to wait and eventually started taking one month off every summer. Corey is a marriage and family therapist, while his wife is a CPA. Learn how Corey’s wife negotiated a month off every summer as part of her contract. Cory maintained his work responsibilities while traveling, and his wife took occasional days off to catch up on work.    In this conversation, Corey Allan and Jillian discuss the benefits and challenges of taking a mini-retirement and traveling as a family. They emphasize the importance of framing the experience in a positive way and viewing it as an opportunity for personal growth. They also discuss the normalcy of conflict and the need for space in relationships. The mini-retirements strengthened their marriage and created lasting memories for their family. Cory shares the reactions he has received from friends and family about his lifestyle and encourages others to make intentional choices to create the life they want. They also discuss the value of flexibility and the benefits of traveling with young children. Takeaways Asking for what you want and taking risks can lead to great experiences Maintaining work responsibilities while traveling is possible with proper planning and delegation Mini-retirements can strengthen marriages and create lasting memories for families Frame a mini-retirement as an opportunity for personal growth and positive experiences. Conflict is normal in relationships, and it can be an opportunity to learn more about oneself. Create intentional choices to design the life you want. Flexibility is key in making the most of travel experiences. Traveling with young children can provide valuable learning opportunities.

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.