Always Come Back to the Why | Alan and Katie Donegan | Ep 569

41 snips

Oct 20, 2025

Guest

Katie Donegan

Guest

Alan Donegan

Alan Donegan, founder of Rebel Finance School, and his wife Katie, a co-founder, share their insights on achieving financial independence with intention. They discuss the significance of understanding your 'why' and how it drives meaningful spending. Tips for making adult friendships and overcoming social fears feature prominently. The Donegans highlight the importance of monthly finance meetings to align goals and values, while advocating for geo-arbitrage as a strategy for lifestyle design. They inspire listeners to embrace change and experiment with life for richer experiences.

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ANECDOTE

Meetups As A Friendship Engine

Alan and Katie use ChooseFI local groups to make friends wherever they travel.
They credit meetups with helping build community and meaningful connections worldwide.

ADVICE

Go From Lurker To Participant

Do stop lurking and attend a local meetup to meet like-minded people.
Ask someone out for coffee or a hike and accept that vulnerability often leads to friendship.

INSIGHT

Be Interested To Be Interesting

The quickest way to be interesting is to be interested in others.
Asking good questions usually creates stronger connections than rehearsed stories.

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Brad, Katie, and Alan Donegan discuss the significance of understanding the "why" behind pursuing financial independence (FI). They delve into their journey, emphasizing the importance of community, intentional spending, and lifestyle design. Listeners are encouraged to confront their fears of rejection when building friendships and to embrace vulnerability for meaningful connections. The Donegans advocate for tracking spending to align financial choices with personal values, reshaping the narrative around saving into one focusing on buying freedom.

Chapters:

Introduction to the Donegans’ Journey (00:00 - 01:55)
- Overview of where the Donegans are currently living and their latest adventures.
Building Community and Friendship (03:20 - 06:24)
- The significance of joining local ChooseFI groups to foster connections.
- Overcoming the fear of rejection and expanding your social circle.
Monthly Finance Meetings (45:12 - 51:01)
- The importance of having regular financial discussions with a partner to evaluate spending and financial goals.
Tracking Spending (51:01 - 54:41)
- How tracking spending drives awareness and better financial choices aligned with personal values.
Flexibility in Lifestyle Design (54:41 - 01:24:43)
- The concept of geo-arbitrage and adjusting your lifestyle to lower costs.
- Emphasizing the importance of understanding the philosophy behind financial independence to enhance life experiences instead of simply focusing on multiplication of wealth.

Key Quotes:

"Stay focused on your core purpose." (01:24:43)
"Live life enjoyably, not just to save." (00:46:58)
"Everything good in life comes on the other side of being vulnerable." (00:09:11)
"The quickest way to be interesting is to be interested." (00:13:01)
"Understand your core motivation." (00:45:47)

Actionable Takeaways:

Join Local ChooseFI Group - Participate in meetups to connect with like-minded individuals. (Timestamp: 00:06:03)
Track Your Finances Monthly - Enhance your awareness of spending and align it with your values. (Timestamp: 00:45:12)
Engage with Others - Foster connections by asking questions and showing genuine interest. (Timestamp: 00:13:01)

Discussion Questions:

What is your personal "why" for pursuing financial independence? (Timestamp: 00:45:47)
How can you incorporate community into your FI journey? (Timestamp: 00:03:20)
What steps can you take to tackle the fear of making new friends? (Timestamp: 00:06:24)

Action Items:

Ask someone out for coffee or a hike this week. (Timestamp: 00:41:30)
Review your monthly spending and identify areas for improvement. (Timestamp: 00:51:01)

Related Resources:

Rebel Finance School – A platform for financial education and personal growth.