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Happy Money Series | How to Spend Well and Enjoy Your Money More  In the winter of 2025, after five years of 'we should really do this,' my friends and I boarded a flight to Hokkaido, Japan. We were going to experience "Japow", the legendary powder snow that has made Hokkaido one of the most coveted ski destinations on the planet. If you're not familiar, many ski resorts in Hokkaido (the north island in Japan) receive well over 500 inches of snowfall in any given winter. It's one of the snowiest places in the world, and we had been waiting years to finally ski it firsthand. The planning phase of this trip alone was a rewarding process; locking down the tour company, mapping out resorts, researching restaurants, building a loose itinerary for Tokyo and Kyoto. Months of excitement and anticipation materialized on a shared google doc, building toward our January departure date. Then, in the week before we left, a dry spell appeared in the forecast. We weren't too worried… a few days without fresh snow wouldn’t completely ruin the trip. But it was not a just few days…  This dry stretch lasted our entire 10-day ski touring trip; not a single inch of fresh snow fell while we were in Hokkaido — one of the snowiest places in the world — during a winter where most of the resorts we visited recorded 400-600” snowfall totals. Not an inch. I’d being lying if I said this didn’t crush our collective spirits. Yes, we were in Japan, one of the most incredible countries I've ever visited. Yes, we were all skiing blue-bird days together, eating amazing food, and exploring somewhere none of us had ever been. Yes, we still laughed the entire trip. We also spent several days in Tokyo and Kyoto before flying home, and those days were nothing short of spectacular. But if you had asked me to rate my ‘Japow’ experience in real time? I would have given it a 7 out of 10. I came in expecting knee-deep powder, and the reality didn't match. When you build something up for so long, the gap between expectation and experience can be a gut punch. Looking back on that trip today, though, I wouldn’t trade it for anything. I'd go back tomorrow if I could. I was with some of my closest friends, who, on any given day are scattered across the country and are seldom all in the same city at the same time. We spent two weeks together exploring a country we had never seen. We skied nine days in a row, ate incredibly well, and laughed constantly, even at our own terrible snow fortune. In hindsight? That trip is a 10/10. Easily. That gap between a 7 in the moment and a 10 in the rearview is exactly what this article is about. Memories don't just sit in some drawer in the back of our brains. Memories appreciate. When you understand the psychology behind why that happens, experiences (like my trip to Japan) stop feeling like a splurge and start looking like one of the best investments you can make with your money. Memories Don't Depreciate, They Appreciate There is a reason you remember your best trips more fondly than you experienced them in real time. It isn't selective memory or wishful thinking. Through a process researchers call the Fading Affect Bias, the emotional weight of negative experiences fades significantly faster than the emotional weight of positive ones. The long airport lines, the bad weather, the flight delay; all details that lose their sting over time. The peaks survive.¹ A 2023 study out of Cornell illustrated this as cleanly as any: participants consistently rated past experiences more positively months later than they did in real time, and their satisfaction continued to climb the more they retold the stories.² This is the opposite of what happens with material goods. Buy a new car, and the thrill peaks somewhere around the first week. From there, hedonic adaptation kicks in and the brain recategorizes it from "exciting new thing" to "background of normal life." Your brain just stops registering the new car almost right away.³ Experiences work differently because memories are not static recordings. Every time you recall a trip, your brain reconstructs it. In the process of that reconstruction, the hippocampus and amygdala work together to give a higher emotional weighting to the positive moments. The result is a memory that improves with age. The Three Phases of Experience Value Material purchases have one moment of peak value: the day you buy them. Experiences are different; they pay you back in three separate ways. Phase 1: Anticipatory Utility The return on a great trip starts long before you board the plane. Behavioral economists call this anticipatory utility, and research suggests it can be the highest-joy phase of the entire experience. A Cornell study found that people derive more positive emotion from anticipating an upcoming experience than from anticipating an upcoming purchase. The planning itself becomes part of the product.⁴ For our Japan trip, that meant five years of conversation, a shared Google doc, resort and hotel research, and restaurant lists. The trip hadn't even happened yet, and it was already delivering. Phase 2: Experiential Utility This is the phase we tend to over-weigh when deciding whether a trip was "worth it." It is also the most volatile. Weather, logistics, illness, and unmet expectations can all drag the real-time rating down. As my Japan trip demonstrated, a 7 in the moment is not the final score. The experience is significant, but it is just one chapter of a three-chapter story. Phase 3: Memory Utility This is where the real return lives. Every time you recall the trip, share a story from it, or laugh about what went wrong, you are collecting a memory dividend. Unlike a stock that pays out once a quarter, this dividend has no dividend schedule and no expiration date. The more you retell it, the more embedded it becomes in your identity. Economists and psychologists describe this as residual utility, and here’s what makes it genuinely remarkable from a financial perspective: the ROI on a memory technically increases every year you hold it, at zero additional cost.⁵ A $2,000 trip we revisit mentally and socially for the next 20 years is a completely different purchase than a $2,000 Peloton bike collecting dust in the garage. The price tag may be the same, but the return we receive is not even close. The Social Dividend There is one more dimension to the return on experiences that anyone who has sat around a dinner table with good friends understands: Experiences are socially rich in a way that material goods simply are not. Talking about a material purchase tends to trigger social comparison, while talking about an experience tends to trigger social connection. When you mention a new house or new car, people start benchmarking. When you tell the story about a trip you took, people tend to lean in and contribute to the conversation.⁶ My Japan story is a perfect example. Every time we tell someone about that trip, they ask about the food I ate, cities I visited, and places I saw. This is the social fungibility of experiences. They open conversations, build connections, and become part of a shared narrative between the people who’ve experienced something similar. Material goods typically fail to accomplish this same social value. The Investment Reframe The three-phase framework also undersells one of the best parts about investing in experiences: even the disasters can pay off. Take a Europe trip I went on in 2017. My wallet got stolen in the airport right before I got on the plane to leave, which left me cash-strapped and credit card-less on a foreign continent (this was the pre-apple pay era). I had to get really creative just to move between cities, constantly asking strangers for help, and at one point, missing a flight from London to Germany because a train kiosk wouldn’t accept anything other than credit cards. In finance terms, this was a total portfolio collapse. It was stressful and downright frustrating at times. But in the rearview mirror, that disaster is now one of my highest-growth assets. My pain made for a hilarious post-mortem breakdown of my travels. I get to share the story of my wallet-less, struggle-filled, solo Europe experience again and again. When we spend on experiences, we are essentially diversifying our lives. We are moving numbers from our bank account into a permanent, inflation-proof residency in our own identity. Most material goods we buy end up in a landfill, but even an experience that registers as a "market meltdown" becomes a good story to tell forever. So, stop looking at experiences as a "line-item expense." It’s a capital allocation toward the only version of wealth that actually appreciates as you age. Conclusion Travel, concerts, sporting events, festivals, beach days, holiday events, family dinners… these aren't frivolous line items to be justified after the "real" financial decisions are made. They ARE the real financial decisions, at least when it comes to where discretionary dollars generate the most lasting return. The three-phase return on our experiences (anticipation, the event itself, and years of memory dividends) makes a genuinely compelling case for how we should spend our discretionary money. Your financial plan should reflect that. Not in a reckless manner or at the expense of the fundamentals (emergency expenses, retirement saving, etc). However, if the choice is between another material purchase that flatlines in value and an experience that compounds in your memory for the next twenty years, the math skews toward the latter. And for those approaching retirement: the window for some of these experiences is finite in a way that a bank account balance is not. Spend accordingly. More Reading: Want to Enjoy Your Coffee More? Don’t Buy It Every Day Why Americans Are Still Grieving Over High Prices Retirement Calculators Give You One Number. Reality Gives You a Range. References ¹ Walker, W.R., Skowronski, J.J., & Thompson, C.P. (2003). Life is pleasant and memory helps to keep it that way. Review of General Psychology, 7, 203–210. ² Kumar, A., Killingsworth, M.A., & Gilovich, T. (2014). Waiting for Merlot: Anticipatory consumption of experiential and material purchases. Psychological Science, 25(10), 1924–1931. ³ Frederick, S., & Loewenstein, G. (1999). Hedonic Adaptation. In D. Kahneman, E. Diener, & N. Schwarz (Eds.), Well-Being: The Foundations of Hedonic Psychology. Russell Sage Foundation. ⁴ Kumar, A., Killingsworth, M.A., & Gilovich, T. (2014). Waiting for Merlot: Anticipatory consumption of experiential and material purchases. Psychological Science, 25(10), 1924–1931. ⁵ Van Boven, L., & Gilovich, T. (2003). To do or to have? That is the question. Journal of Personality and Social Psychology, 85(6), 1193–1202. ⁶ Gilovich, T., Kumar, A., & Jampol, L. (2015). A wonderful life: Experiential consumption and the pursuit of happiness. Journal of Consumer Psychology, 25(1), 152–165.
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