Retire Often – Details, episodes & analysis

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Retire Often

Jillian Johnsrud

Business

Frequency: 1 episode/26d. Total Eps: 37

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.

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https://www.instagram.com/dougcunnington
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https://www.instagram.com/reclaim_physician_coaching
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https://www.instagram.com/stacyennis
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https://www.youtube.com/@DougCunnington
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https://youtube.com/@stacyennisauthor
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https://www.youtube.com/@Roadmapmoney
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Score global : 58%

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Opting for mini-retirements instead of FIRE

Season 1 · Episode 35

Wednesday, January 21, 2026 • Duration 27:26

Brian Herriot discusses the concept of mini retirements and the journey towards financial independence with Jillian. Brian shares his personal experiences, including the challenges he faced during the pandemic and how he shifted his perspective on what financial freedom means. They explore the importance of taking breaks, the lessons learned from traveling, and the value of optimizing for time freedom rather than just financial wealth.

Pre-order Time Freedom and get the audiobook free—instant access today, paper copy in September. Normally, that takes three copies, but for "Retire Often" listeners, just one.

timefreedombook.com | code: JILLIAN

Takeaways:

Financial independence is not just about money; it's about time control
Taking breaks can enhance creativity and professional growth
It's important to challenge limiting beliefs about work and time off
A seasonal schedule can help balance work and personal life

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Mini-Retirements in Healthcare and Other All-Consuming Careers

Season 1 · Episode 34

Wednesday, October 29, 2025 • Duration 28:58

28% of doctors consider leaving the profession on a weekly basis. Can mini-retirements allow people to stay in these demanding careers that they love, but are burning them out? Jillian and Christie discuss the importance of taking sabbaticals in the healthcare profession, particularly in light of the burnout culture that often pervades the field. Christie shares her personal journey of feeling overwhelmed in her role as a palliative care physician and the steps she took to reclaim her well-being through a sabbatical. They explore the systemic issues that contribute to burnout, the fear associated with career transitions, and the importance of finding agency and options within the medical field. The discussion emphasizes the need for self-care, the value of coaching, and the significance of maintaining one's identity outside of work.

Links:

Website: reclaimphysiciancoaching.com, where any physician interested in exploring coaching can book a free introductory conversation.
Instagram: https://www.instagram.com/reclaim_physician_coaching
Facebook: https://www.facebook.com/profile.php?id=61578579675081

Takeaways:

Many doctors feel trapped in their roles due to systemic pressures
28% of doctors contemplate leaving medicine weekly
Cultural beliefs can create a false binary of being 'all in' or 'all out'
Investing in wellness programs can save healthcare institutions money
Fear of losing identity can hinder career transitions
Creating a structured sabbatical using the mini-retirement phases can enhance the experience
Finding community support can help in navigating career changes

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Seasons of life with expiration dates

Season 1 · Episode 25

Wednesday, December 11, 2024 • Duration 13:43

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

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When the dream job becomes soul crushing

Season 1 · Episode 24

Wednesday, November 27, 2024 • Duration 28:54

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

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Embracing the Three Phases of a Mini-Retirement

Season 1 · Episode 23

Wednesday, November 13, 2024 • Duration 19:23

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.

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Your Guide to Negotiating A Month Off

Season 1 · Episode 22

Monday, October 7, 2024 • Duration 33:32

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

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Building Freedom for Mini-retirements into Your Business

Season 1 · Episode 21

Wednesday, October 2, 2024 • Duration 34:36

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

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Do you have the Capacity to Suffer or the Courage to Change?

Season 1 · Episode 20

Monday, September 23, 2024 • Duration 18:56

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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The Rest You've Earned

Season 1 · Episode 19

Wednesday, August 28, 2024 • Duration 22:09

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

Business Growth after a Year Off

Season 1 · Episode 18

Wednesday, August 14, 2024 • Duration 27:32

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.

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Retire Often – Details, episodes & analysis

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Retire Often – Details, episodes & analysis

Podcast details

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Apple Podcasts

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Other28

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