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PODCAST

Retire Often

Jillian Johnsrud

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.

business careers

All Episodes

32:17

F-You Money, Side Hustles, and Hacks to Afford for...

Retire Often ·

2025/09/10

Jillian and Chris dive into Chris’s seven-month mini-retirement, where he and his wife traveled through Asia and Europe. Chris shares how they structured the trip, from budgeting and planning to navigating without a traditional schedule. He explains the cost advantage of taking a long trip vs many shorter trips to accomplish a long bucket list. And he goes through different hacks to increase income during a mini-retirement and reduce travel costs. We also talked about how his next upcoming

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23:16

Reinventing Life Before Retirement

Retire Often ·

2025/06/25

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 offers insights on using writing as a tool for self-discovery and

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36:46

JL Collins: affording mini-retirements on the Simple...

Retire Often ·

2025/06/11

In this conversation, Jillian and JL Collins explore the themes of financial independence, the value of mini retirements, and the importance of life experiences. They discuss the parable of the monk and the minister, which illustrates the balance between wealth and resilience. The conversation delves into the fears surrounding financial decisions and the journey towards financial independence, emphasizing that experiences in youth may not be as accessible in later years. Through a case study of

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27:38

Mini Retirements to Practice for Early Retirement

Retire Often ·

2025/05/14

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 to early retirement, and the value of practicing mini retirements to

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28:36

How to Decouple Identity from Career for a...

Retire Often ·

2025/01/29

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 self-evaluation and planning for a fulfilling life beyond traditional

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11:11

Mini Retirements: A Lifetime of Adventures by saving...

Retire Often ·

2025/01/15

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 their experiences. Takeaways How saving an additional 6.5% of your

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30:19

Developing Failure Immunity with an around the World...

Retire Often ·

2025/01/01

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 learned about resilience, the value of pausing in life, and his upcoming

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13:43

Seasons of life with expiration dates

Retire Often ·

2024/12/11

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

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28:54

When the dream job becomes soul crushing

Retire Often ·

2024/11/27

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

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19:23

Embracing the Three Phases of a Mini-Retirement

Retire Often ·

2024/11/13

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

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33:32

Your Guide to Negotiating A Month Off

Retire Often ·

2024/10/07

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

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34:36

Building Freedom for Mini-retirements into Your Business

Retire Often ·

2024/10/02

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

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18:56

Do you have the Capacity to Suffer or the Courage to...

Retire Often ·

2024/09/23

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.

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22:09

The Rest You’ve Earned

Retire Often ·

2024/08/28

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

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27:32

Business Growth after a Year Off

Retire Often ·

2024/08/14

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

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32:33

Take an epic year-long road trip with the family

Retire Often ·

2024/07/31

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

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33:30

How to Take a Mini-Retirement Every Year

Retire Often ·

2024/06/06

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

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35:46

Reinventing Yourself Post-Divorce with Travel

Retire Often ·

2024/02/07

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

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28:04

Road Trip Across Canada

Retire Often ·

2024/01/24

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

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31:28

Negotiating Time Off to Hike the Camino Trail

Retire Often ·

2024/01/03

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

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32 results

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