ChooseFI Episode 569: "Always Come Back to the Why" with Alan and Katie Donegan

Release Date: October 20, 2025
Guests: Alan and Katie Donegan, Rebel Finance School
Host: Brad Barrett (ChooseFI)

Episode Overview

This episode is a candid, wide-ranging conversation between Brad Barrett and the Donegans (Alan and Katie) from Rebel Finance School. The central theme is the importance of continually returning to "the why" behind pursuing Financial Independence (FI)—the core purpose and intentionality that drives lifestyle and money decisions before and after achieving FI.

The discussion weaves through topics like community-building in the FI space, overcoming adult social fears, changing one’s relationship with money post-FI, the mechanics of managing finances in early retirement, the importance of flexibility and experimentation, and how to deal with economic uncertainty and market fears.

Key Discussion Points & Insights

1. The Power and Importance of FI Community

• International connections: The Donegans, currently in Palm Springs, share how they use local FI groups to connect with like-minded people wherever they travel.
• Community autonomy: Brad reflects on how each ChooseFI group grows its own distinct flavor, powered by the local admins and diverse members.
• Advice for newcomers: Alan and Katie urge listeners not to lurk but to show up and push through the fear of being "the outsider." The recurring message: putting yourself out there is crucial to building adult friendships.
• Quote:

  "People are so friendly at these meetups. They just, like, welcome you in, and it's just a lovely community feel." (Katie, 06:17)

Timestamps

• Community-building and making friends: [01:59]–[10:34]

2. Redefining Adult Friendship

• Flexible definitions: Alan, Katie, and Brad explore what "friend" means as an adult (it's OK if you don't talk every week).
• Low-bar for connection: Alan notes that for him, the bar is simply "someone really nice and interesting that I've met once and that I can reach out to again."
• The art of going first: Initiating a second hangout—"platonically asking someone out"—is likened to dating, and it's acknowledged that feeling nervous is entirely normal.
• Quote:

  "The quickest way to be interesting is to be interested." (Alan, 12:39)

Timestamps

• Adult friendship and connection: [06:56]–[14:34]

3. Avoiding the "Shoulds" and Living the FI Life

• Life post-FI isn’t about ticking boxes: Brad emphasizes leaving behind the "shoulds," and instead focusing on intentional living based on real desires, free from outer expectations.
• Front-loading the sacrifice: Discussion critiques the idea that FI is about deprivation and reframes it as a question of sequencing big, expensive fun (like an African safari) until after FI, rather than outright sacrifice.
• Compounding and freedom: Alan highlights how investing early and letting compounding work its magic allows you to "spend the same dollar many times" in the future.
• Quote:

  "At the start you can only spend every dollar once, but later you can spend it many times because compounding turns it into many more dollars." (Alan, 17:14)

Timestamps

• Mindset and reframing the FI journey: [14:49]–[21:44]

4. The Donegans’ Financial Results and Realities

• Transparency: The Donegans retired with $1M in 2019, and despite drawing down for six years, their net worth is now $2.4M due to market growth and compounding.
• Side income & giving back: Their business brings in some income—but much less than they spend, and they invest their time and money to keep Rebel Finance School free.
• Dealing with "retirement police": Alan references Millennial Revolution’s A/B portfolio experiment to reassure skeptics that FI "works" even without post-FI income.
• Quote:

  "We retired in 2019 with a million invested, we've spent a bunch of money, and we're now worth 2.4 million six years later ... this stuff is magic. And you don't have to understand it. You just have to invest your money." (Alan, 21:44)

Timestamps

• Donegans' post-FI finances: [19:02]–[26:21]

5. Embracing Change and Experimentation

• Changing isn’t easy: The group acknowledges friction and fear in making life changes but suggests that all growth lies just beyond our comfort zone.
• Small steps matter: Katie suggests "exposure therapy" for change—take small risks, try different coffee shops, or cross the street in a new place.
• Quote:

  "Change can be the most amazing thing in the world ... if you never risk it, you'll never find something better." (Alan, 31:14)

Timestamps

• Change and intentional experimentation: [29:29]–[41:20]

Memorable Moment

• Alan’s "Ask Someone Out" Challenge:

  "Here's the challenge to everyone listening ... Ask someone out. That's your challenge for this week. Ask someone for a coffee, ask someone for a hike, ask someone to play board games, ask someone else." (Alan, 41:20)

6. Maintaining a Healthy Money Relationship as a Couple

• Monthly Finance Meetings: For 10 years, Alan and Katie have met monthly to review net worth, spending, what brought value, and their "why".
• Gamifying finances: They make it fun with burritos or coffee. Others do "cheese and wine" meetings—whatever works!
• Always Return to the Why: When money debates arise or anxiety spikes ("That seems really high!"), they refocus on their shared mission: to use wealth for experiences and living fully, not accumulating endlessly.
• Quote:

  "Always come back to the mission. Always come back to the why." (Alan, 46:29)

  "I don't want to be the richest person in the graveyard ... Let me enjoy it. And that was the purpose." (Katie, 47:01)

Timestamps

• Couple’s money management and best practices: [43:42]–[51:48]

7. Withdrawal and Spending Strategies in Early Retirement

• Trackers, not budgeters: The Donegans don’t have a fixed monthly budget—they track spending, compare to their safe withdrawal rate (now comfortably using 5%), and adjust as needed.
• Geoarbitrage as flexibility: Living in countries like Vietnam or Colombia can cut expenses drastically if needed (e.g., in big downturns).
• Stress-testing FI in practice: Their approach is more conservative than the "textbook" 4% rule, but if needed, they know they can adjust spending or locale.
• Quote:

  "If you're unwilling to ever change your spending, then you should stick to 4%. If you're willing to be even remotely flexible, then you could probably increase that amount." (Alan, 55:56)

Timestamps

• Withdrawals and practicalities of post-FI spending: [51:48]–[60:26]

8. Dealing with Global Instability and Market Fear

• No "imminent collapse": Brad strongly rejects fear-based investing or lifestyle decisions, instead advocating for optimism, perspective, and a focus on what you can control.
• Refusal to time the market: The Donegans stick to a globally diversified index portfolio because market timing is a fool's errand and nobody can do it reliably, repeatedly.
• Quote:

  "Anytime we try to get our brains involved in 'I know better'...the likelihood that you're going to know better than everybody else twice, not less once...is infinitesimal." (Brad, 63:49)

Timestamps

• Handling fear of economic collapse: [61:13]–[72:18]

9. Why Passive Index Investing Still Works

• No concern for ‘index fund bubbles’: The hosts refute YouTube scaremongering about "index fund bubbles," reiterating index funds’ self-cleansing structure and long-term reliability.
• Stock picking isn’t for everyone: Even professionals can’t consistently beat the index; survivorship bias means outliers shouldn’t drive your strategy. Time is better spent living, not obsessively picking stocks.
• Quote:

  "If 200,000 people listening to this put all their money in an index fund, 200,000 of them would be successful over the long term. That is a replicable strategy." (Alan, 83:16)

Timestamps

• Index fund “bubble” and investment strategies: [73:39]–[84:44]

10. Always Come Back to the Why

• Simplicity & intention at the core: The episode closes by re-centering on the core message: in finances, relationships, and lifestyle choices, repeatedly ask yourself what you want out of life (your "why"), and let that guide your actions.

• Quote:

  "Always come back to the why. We're trying to make the best choices we can make to live the best life we can, however you define that ... You have to iterate and you have to work on it. But go out there and have fun and come back to that why, whatever that means to you." (Brad, 86:40)

Notable Quotes & Memorable Moments (with Timestamps)

• On starting connections:
  "Come out of the shadows, stop lurking. Go meet some people." (Katie, 06:31)
• On intentional post-FI living:
  "I don't ever think about should anymore. And it's just a really. Yeah, it's a really liberating thing." (Brad, 15:30)
• On compounding magic:
  "I've spent that money. I've spent it on trips, on food, on pizza... and I'm worth more than I've ever earned. So technically I've lived for free." (Alan, 19:02)
• On couple's finances:
  "Always come back to the mission. Always come back to the why ... the small details melt away because you're matched on the why." (Alan, 46:29)
• On living despite global fears:
  "I am responding by having a nice life, enjoying my friends, because I can't do anything about that." (Alan, 67:15)
• On index fund “bubble” scares:
  "Until somebody presents me with a better strategy, I'm 0% concerned about this." (Brad, 77:15)
• On stock picking vs. index funds:
  "It's like the light switch. I don't really understand electricity, Brad, but I love it ... I can invest in an index fund so I can have my time." (Alan, 84:44)
• On strategy for life and money:
  "There's a way to have a better life and there's a way to have a worse life, why on earth would you not pick the better way? It makes no sense." (Brad, 70:26)

Practical Takeaways

• If you feel isolated in your FI journey, take the risk of joining a meetup or asking someone out for coffee—you’re almost always rewarded with connection. ([41:20])
• Consistency and fun matter in money meetings: long-term success comes from regular check-ins, asking what’s working, and celebrating progress. ([43:42]–[51:48])
• Flexibility is a superpower in FI. The willingness to adjust spending, travel, or even location provides both mental freedom and practical security. ([55:56], [57:30])
• Ignore fear-based financial media. Focus on time-tested strategies—mainly index investing, living intentionally, and returning to your core “why.” ([77:15], [84:44])

Resources Mentioned

• Rebel Finance School – free self-paced financial education from Alan and Katie
• ChooseFI Local Groups – FI meetups worldwide
• Books/Authors:
  • The Simple Path to Wealth by J.L. Collins
  • Millennial Revolution (Kristy Shen & Bryce Leung)
  • David Gardner & Motley Fool
  • Brian Feroldi
• Concepts:
  • "Retirement Police"
  • The 4% Rule & Sequence of Returns Risk
  • Geoarbitrage
  • Index Fund “Bubble” Debate
  • Compounding Magic

Final Word

Always come back to the why—whether making spending decisions, navigating relationships, or facing financial fears. Let your intentional, personal mission guide every choice, keep experimenting and learning, and lean into community and connection along the way.

For self-paced lessons on building your own financial independence and mindset, visit Rebel Finance School, or join one of the 300+ ChooseFI local groups worldwide.