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

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)