Retire Often

Retire Often

Why retire once when you can retire often? Hear real mini-retirement stories. See how mini-retirements can unlock work-life balance, purposeful living, and financial freedom.

Episodes

June 25, 2025 23 mins

Jillian and Brenda explore Brenda's journey of taking a mini-retirement to rediscover herself through hiking and writing. Brenda shares her experiences of stepping away from a traditional career to embrace nature and the writing process, discussing the emotional and financial aspects of this transition. They delve into themes of trust, community among hikers, and the importance of redefining success in a personal context. Brenda of...

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In this conversation, Jillian and JL Collins explore the themes of financial independence, the value of mini retirements...

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In this conversation, Jillian and Doug discuss the concept of mini retirements and how they can lead to a fulfilling lifestyle while pursuing financial independence. Doug shares his personal experiences with mini retirements throughout his career, emphasizing the importance of taking breaks, traveling, and spending quality time with family.

They explore the challenges and benefits of unconventional choices, the gradual transition t...

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Mitch shares his journey towards a mini-retirement, discussing the challenges of decoupling his identity from work, the role of therapy in his transition, and the planning involved in their adventure. He reflects on the joy of spending quality time with family while traveling and the unexpected return to work with a new perspective. 

Mitch offers encouragement for others considering a similar path, emphasizing the importance of sel...

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Jillian discusses the concept of mini-retirements, exploring how much one needs to save to enjoy these experiences throughout life. She emphasizes the importance of planning, budgeting, and finding ways to increase income or reduce expenses to make mini-retirements feasible. Jillian provides practical calculations and strategies for saving, encouraging listeners to think creatively about financing their adventures and maximizing th...

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In this conversation, Charles shares the inspiring journey of taking a seven-month mini retirement with his family, exploring the motivations behind their decision, the planning process, and the transformative experiences they encountered along the way.

He discusses the impact of travel on his children, the importance of adaptability, and how the trip allowed them to reconnect as a family.

Charles also highlights the lessons learne...

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December 11, 2024 13 mins

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 expiratio...
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November 27, 2024 28 mins
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 ...
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In this conversation, Stacy shares her experiences part way through her mini retirements. She shares how she created d...

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October 7, 2024 33 mins

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 c...

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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 fam...

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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 sign...

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August 28, 2024 22 mins

Frances Benjamin shares her mini-retirement story and the transformative impact it had on her life. Before her mini-r...

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    August 14, 2024 27 mins

    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 emotionall...

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    If you have ever been curious about taking an epic yearlong road trip, Heidi’s story of how her and her family embarked ...

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    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...

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    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...
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    January 24, 2024 28 mins

    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 h...

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    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 suscep...

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    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 s...

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