ChooseFI Podcast, Ep 561: Mini-Retirements—Test Driving Financial Independence

Date: August 25, 2025
Host: ChooseFI (Brad)
Guest: Jillian Johnsrud
Episode Theme:
Exploring the power and practicality of mini-retirements as a way to ‘test drive’ financial independence, build a richer life, and prepare emotionally and logistically for the transition into full FI (Financial Independence). The episode delves into why mini-retirements matter, how to design them, and actionable steps to make the most out of these intentional breaks from career—and why practicing retirement along the journey is as important as the end goal itself.

Main Topics & Discussion Points

1. Defining Mini-Retirements ([02:48])

• Three Core Elements:

  • At least one month off
  • Stepping away from primary job/career
  • Focused on something meaningful and enjoyable (not an unplanned, miserable layoff)

    “A month can be really powerful… focus on something that’s meaningful and potentially enjoyable for you.” – Jillian [02:48]

• Not simply an escape or gap due to negative circumstances, but an intentional pause to invest in life, family, exploration, or self-care.

2. The Philosophy: Living Through ‘Seasons of Life’ ([05:05])

• Life is made up of unique, fleeting “seasons” that seldom repeat (children’s ages, health, relationships, etc.).
• Many opportunities are more urgent than we realize (e.g., family trips, health sprints, time with parents).
• Profound personal stories illustrate the unpredictability of life and the regret of missed opportunities:

  “It was a really deep… difficult lesson I learned when our oldest passed away… that was the only opportunity. And I had no idea at that moment…” – Jillian [06:01]

• Regret over missed life moments can outweigh the fear of lost income or delayed FI.

3. Balancing FI Discipline with Living Fully ([11:48])

• FI audiences trend toward delayed gratification and frugality; essential to also value living well along the way.
• Contrasts those who overspend on mediocre experiences vs. those who over-save at the expense of unforgettable moments.
• Exercise: If hitting FI a few years later meant having a lifetime of rich experiences, is it worth it?

  “You worked 64 to 67. But you can look back and say, but I did all of the things when I had the chance.” – Jillian [11:48]

4. Mini-Retirements as Practice for Early Retirement ([17:59])

• The “Practice” Principle: Just as you don’t run a marathon with no training, you shouldn’t treat retirement as a ‘first try’ event.

  “If early retirement is something you want, you should probably practice it.” – Jillian [17:59]

• Many who reach FI jump straight into retirement unprepared, only to struggle and sometimes return to work.
• Mini-retirements trial-run core skills: coping with free time, spending out of investments, exploring interests, and processing the emotions of identity change.

5. Overcoming FI Community Fears ([22:33])

• Key fear: Unable or unwilling to ‘spend down’ investments after a lifetime of saving.
• Mini-retirements offer a safe practice for withdrawing funds, living without regular income, and testing the psychological transition.

  “Being good at investing money does not necessarily mean you’re good at pulling money out of investments. You’re good at watching the number go up. Are you good at watching the number go down?” – Jillian [21:47]

6. Designing Your First Mini-Retirement ([35:22])

• Start Small, Focused: For a one-month break, pick one major goal; three at most for longer periods.
• How to Choose What to Do:
  • Reflect on your FI “why”—what were you hoping would be different, compelling?
  • Find the intersection of “urgent and important”—what can't wait or what’s uniquely possible now?
  • Examples: Time with children before teens, travel with aging parents, focused health reboot, intensive therapy.

    “There must have been some compelling reason that set you on this path. What if we do a sample size of that right now?” – Jillian [37:04]

7. Avoiding Disillusionment: Experimentation is Key ([32:44])

• Don’t expect every dream activity to be fulfilling; use mini-retirements to test interests and identify what is genuinely meaningful or enjoyable.
• Rethink ‘failure’: Scratching failed ideas from the list is actually forward progress.

  “Spread out the disappointment. Try all this stuff on this list of 50 things and cross off a bunch of the stuff that you don’t like. Learn that early so you can find new things to experiment with…” – Jillian [30:53]

Notable Quotes & Memorable Moments

• “Sometimes we’re more motivated by loss than we are upside... sometimes I try to leverage that fear of regret as powerfully as the fear of disaster.” – Jillian [09:51]
• “Most people have very little practice organizing our time in a way that’s meaningful and enjoyable... Most people I know, even in mini retirements… feel a little untethered.” – Jillian [46:06]
• “If you’re scared to take a month off of work, and you think taking 40 years off will be easy breezy, deal with the fear in this little teeny, tiny low risk package, and then you’ll get better at dealing with it…” – Jillian [19:11]
• “Our lives are the same way. If you take a month and make this big upfront investment—in yourself, in your hobbies, in your relationships… you’ll reap those rewards for years, if not decades down the line.” – Jillian [28:06]

“Nuts & Bolts” — Tactical Takeaways

• Types of Mini-Retirements:
  • Negotiated leave from employer (1-3 months: HR can often facilitate)
  • Between jobs (ideal for 3 months–1+ year)
  • Unplanned interruptions (layoff, family need, etc.—can still be leveraged if you prep mentally/financially)
• Checklist for Planning:
  1. Clarify your FI “why”
  2. Identify 1-3 urgent/important goals (health, relationships, learning, travel, rest)
  3. Negotiate or set the break; line up financial runway
  4. Practice drawing down savings or investments in small amounts ([21:47])
  5. Treat it as a capital investment in your future self ([28:06])
  6. Debrief—what worked, what didn’t, what do you want to try on your next break?

Episode Flow: Key Timestamps

• [02:48] – Jillian defines the mini-retirement and its three core elements
• [06:01] – The power and fragility of “seasons of life”; personal story of loss and perspective
• [11:48] – Navigating the trade-off between rich experiences and hitting FI early
• [17:59] – Why you should “practice” retirement; the marathon vs. mini-retirement analogy
• [21:47] – Psychological challenge of pulling from investments; practicing “decumulation”
• [28:06] – Different shapes of mini-retirements; how to approach employer, planning, and serendipity
• [32:44] – Using experimentation to find what’s truly meaningful and enjoyable
• [35:22] – Practical first steps: how to design your mini-retirement and set achievable goals
• [46:06] – Overcoming the ‘untethered’ feeling; learning to structure meaningful post-work time

Final Thoughts & Resources

• Mini-retirements are the ultimate “trial runs” of life beyond work—giving you confidence, clarity, and skill to live richly before and after FI.
• Jillian’s new book, Retire Often, compiles these frameworks and more. Available September 9, 2025.
• For group coaching, more resources, or to connect: retireoften.com.

“Happiness is one part reducing suffering, but the other part is increasing the meaning of and enjoyment of things.” – Jillian [46:06]