559 | Zero-Based Everything: FI, Travel, and the Art of Starting Fresh | Katie & Alan Donegan

ChooseFI | Financial Independence Podcast

Jonathan Mendonsa & Brad Barrett | Choose FI Media, Inc

Careers, Business, Investing

4.8 • 5.2K Ratings

🗓️ 11 August 2025

⏱️ 83 minutes

🔗️ Recording | iTunes | RSS

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Summary

Most people obsess over net worth. Katie and Alan Donegan calculate something entirely different: their freedom fund. Joined by Brad, the trio unpacks five and a half years of full-time travel, the psychological trap of dividend investing, and why zero-based thinking—"Knowing what I know now, would I choose this again?"—has become their most powerful decision-making tool. Katie and Alan share hard-won lessons from bouncing between Airbnbs in Brazil, the surprising stability they've found as digital nomads, and how they've restructured their portfolio to reflect what money is actually for: buying back your time. Timestamps: 00:00:00 - Introduction with Friends 00:03:48 - Zero-Based Thinking Discussion 00:04:54 - Experiences as Digital Nomads 00:11:04 - Traveling vs. Stability 00:18:44 - Understanding Investments 00:28:00 - Shifting Perspectives on Net Worth 01:20:00 - Closing Thoughts Key Topics: Zero-Based Thinking: Evaluate decisions with the question, "Knowing what I know now, would I choose this again?" Katie and Alan applied this exact framework when deciding whether to rebook a disappointing Airbnb in Brazil. (Timestamp: 00:16:19) Traveling vs. Stability: After five and a half years as digital nomads, Katie and Alan discuss the tension between fast-paced travel and the surprising need for stability—even on the road. (Timestamp: 00:11:04) Freedom Fund Concept: Shift your focus from traditional net worth calculations to a 'freedom fund'—assets that generate freedom, not just income. They've restructured their entire portfolio around this idea. (Timestamp: 00:28:44) Probabilistic Nature of Life: Decision-making isn't about guarantees. Even great choices (two aces in poker) lose one out of 20 times. Understanding probabilities helps frame expectations. (Timestamp: 00:24:20) Quotes: "We get 80 or 90 years on this planet if we're really lucky. The point of FI is to be able to control your time and do what you want." (00:17:43) "Knowing what you know now, would you choose it again? If the answer is no, then it's time to get out." (00:18:36) "Your entire net worth is in your freedom fund." (00:28:44) Resources Mentioned: Rebel Finance School (Timestamp: 00:19:08) What's Your Split? Visualizing net worth (Timestamp: 00:19:08) PDF Guide to Optimize Your Life (Timestamp: 00:57:41)

Transcript

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0:00.0	Hello and welcome to Choose a Phi. Today on the show, we have our good friends, Katie and Alan Donegan. And we're just going to do a fly-on-the-wall conversation amongst friends. We're going to let you in on this conversation that we'd be having anyway. The three of us are great friends. We've traveled the world together. And we have these fun, far-ranging conversations. And we usually talk about life and FI and everything in
0:22.0	between, what we're up to, how we change our minds, what we're reading, what we're watching,
0:26.0	what we're playing, I don't know, maybe commiserating on some things that we have come up in the
0:30.8	world that we're not so thrilled with, et cetera. But at the end of the day, it's about
0:35.2	just thinking and talking and looking at the world and trying to have fun and explore.
0:40.8	And I think that's what Alan and Katie do best.
0:43.1	And yeah, we talk about travel, which they've been doing as digital nomads for five and a half years now.
0:48.6	We talk about zero base thinking, which is an interesting concept they've come up with that I love.
0:52.9	A little bit about Robin Hood and Tesla and selling shares and how difficult or not
0:56.9	difficult that may be, a little bit about dividend investing and then just a lot of fun of what
1:01.5	we're up to in our own lives.
1:02.7	I think you're really going to enjoy this.
1:04.1	And with that, welcome to choose FI.
1:17.1	Katie and Alan Donegan, welcome back to the podcast.
1:17.8	Hello.
1:19.0	We are back.
1:20.2	We are back.
1:20.5	Yeah.
1:22.1	So this is going to be fun.
1:23.8	We envision this episode.
1:26.1	Basically, we talk all the time.
1:27.1	We're great friends.
	...

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