What If More Money Still Doesn’t Feel Like Enough?

Tyler Gardner (0:00)

You saved for decades. You skipped the lattes. You maxed out the 401k. You made it. And what's waiting for you? Three things if you're not careful. Number one, a reluctance to spend. Number two, a fear of living before its time. And three, a calendar so empty it echoes, and an existential identity crisis.

Hello, friends. This is Tyler Gardner welcoming you to another episode of Your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing. So let's get started and get you one step closer to where you need to be. I want to start this week's episode by asking something slightly uncomfortable. What if the biggest financial surprise in your life is that having enough doesn't feel anything like you thought it would? What if, like American writer David Foster Wallace, you publish that masterpiece, and within weeks fall deeper into a depression, asking, well, now what? Or, what if, like professional golfer Scotty Schaeffler, you train your entire life to be excellent at a sport, so excellent, in fact, that you win a tournament, like the Masters, and within a few hours, you're sitting there wondering, what am I cooking for dinner tonight for my family? This week, I'm focusing specifically on the idea that, and yes, I'm assuming a little bit here, we all want more money in some way, shape, or form. Some of us might have a specific number for what we want to see in that retirement account. Others might be fighting throughout their lives to make six figures, and others might not have even named there enough, but are aspiring towards the same idea of completeness and fulfillment based on how much money we make or how much money we've managed to keep.

But what if we're putting the cart before the horse? What if we've been told our entire lives to want more before figuring out what the heck we'd actually do with our lives once we got to that point? What if you save diligently, hit your goals, retire responsibly, and still feel like the main character in a movie that forgot to write the second half of the script? That's what this week's episode is about. We will unpack the personal finance stories hiding behind Monte Carlo scenarios and try to make sense of money without needing a Ph.D., a trust fund, or a laminated Dave Ramsey envelope system. Today we're tackling a question that almost no one wants to admit they're asking. What happens when you make it and it still doesn't feel like enough? This episode is about the regrets I've seen up close in people who've checked all the financial boxes and still feel vaguely like something's missing. We're not talking about blowing your 401k on a yacht, or realizing too late that you probably should have invested in Apple instead of vintage beanie babies. We're talking about the quieter letdowns, the emotional hangover that hits after we achieve that number in the bank account we believed would somehow offer us peace of mind. And hey, if any part of today's episode resonates with you, I'd love it if you'd leave a review on Apple Podcasts, or share the episode with a friend. For those who already have done either or both, thank you. It means the world to me that the show is growing, and you're the ones that make that happen. And frankly, it also lets me know that I'm not just talking into the financial void with nothing but my dog by my side and a half-used moleskin for company. And if you want to go one step further, or if you're so bored of my rambling and wish I'd just sum it all up for you in three quick bullet points, well, I do. I send out a free weekly newsletter with three simple, powerful takeaways that build on each podcast episode. You can subscribe at tylergardner.com or search Social Cap Official on Substack. Think of it as the follow-up you won't forget to open. Hopefully.

Alright, let's begin with the first hard truth and one of the first biggest regrets I see. Regret number one, savers who can't spend, aka the curse of the responsible adult. There's a very specific kind of person I connect with again and again in this line of work. They have excellent dental hygiene, own multiple fleeces and think going out to dinner is something you do after checking the coupon drawer. These are the savers, salt of the earth, budget loving, debt avoiding savers. The kind of people who will drive across town to save eight cents on bananas, even though they spend more than that in gas to get there. The kind of people who proudly brag, we've never paid a dime in credit card interest and say it with the exact same energy someone else might use to announce they just cured Lyme disease. These are the people who have, according to the traditional playbook, done every thing right. They maxed out the 401k, they avoided financial scams, they politely declined annuities from guys named Carl, and did I mention, they floss. I told you they have excellent dental hygiene. And now, well, now they've arrived. The mortgage is paid. The nest egg is, well, egged. Their financial advisor says, You're all set, and you have a 99.7% chance of being OK, whatever the heck that means. And what do they do? Nothing. Because for some reason, they can't spend the money. They won't even look at the money. They treat their brokerage account like a mysterious, haunted attic, something you know exists, but don't dare go into because it's probably full of spiders and emotionally complicated candlesticks. I once worked with a couple worth just under $6 million. They flew economy regularly, stayed in motels that smelled like mildew and broken dreams, and split entrees at dinner because portions are huge. But they were lovely people, thoughtful, kind, generous in spirit, but asked them to spend $500 on themselves, and you'd think I'd suggested they light their grandchildren's inheritance on fire. The problem wasn't them, per se. It was that they weren't ever taught to enjoy their wealth. They were preserving it like jam or old war medals. And I get it. I come from this exact same genetic lineage. I was raised by people who treat wasting leftovers like a mortal sin. We had a family motto growing up. And I quote, That's still good. It applied to food, duct tape, extension cords, socks, and at least once, a couch that had been passed down from one generation to the next, and may or may not have begun to turn green based on certain moldy growth patterns. To be fair, absurdly comfortable couch. So believe me when I say, the savers have my heart, but they also break it. Because here's what's actually going on. They've spent so long building the habit of know that they forgot and forget how to say yes. It's no longer a math problem. It's a story problem. Their entire adult identity has been forged around frugality, restraint, calculated self-denial. They no longer see money as a tool. They see it as a force field, one that keeps them safe, righteous, and respected at the dinner table when someone brings up credit card debt. But the problem with treating saving like a moral virtue is that it becomes sticky. It's not just a habit. It becomes a world view. And over time, that thrift becomes so calcified, it's not a choice anymore. It's just who they are. They're the kind of person who skips appetizers, who reuses tin foil, who orders the cheapest wine, but acts like they did it on purpose, because Malbecs are getting too showy these days. This is why some retirees, even wealthy ones, withdraw less than they're required minimum distribution. Not because they have a plan, but because they don't have one. They're not frugal. They're stuck. And according to the Employee Benefit Research Institute, over 60% of retirees take out less than the government requires. And this isn't because they're planning some grand philanthropic endgame. It's because they're afraid. And not of running out, but of letting go. Now, if you're listening to this and thinking, Tyler, you're being a little harsh here. First of all, yes. And second of all, I say it with love. Because I know this person. Heck, I am this person. You know how I celebrated hitting a big revenue milestone in my business this year? I told myself I'd buy some new furniture for our house that we've lived in with inherited furniture for over five years. Let me repeat that. I told myself I'd do it. That was the reward. Still haven't actually done it. Because every time I get to that final step of looking at the price in my digital cart, I remind myself that the inherited furniture from the previous owners is actually perfectly adequate and comfortable. That's how deep this goes, my friends. But here's what we all miss. Money unused isn't wealth. It's just potential. And potential, like bread, eventually goes stale. So what do we do? We practice. You don't wait until retirement to start learning how to spend. You don't just magically become a joyful, free-spirited, adventurous hedonist at 65 because your fidelity rep said you could. You start now. I recommend something I call an emergency spending account. And this is so, so, so far from an emergency savings account. In fact, it's designed to fight against the emergency savings account mentality. It's not for car trouble. It's not for root canals. It is for fulfillment and for practice, for building the muscles of actually using money in service of your values before your body becomes a value menu of creaks and regrets. I'm talking about setting aside a sliver of your net worth. It doesn't have to be a scary number. Maybe 1%, maybe less. And committing to spending it every year on purpose. Not randomly, not guiltily, not just to treat yourself after a hard week, but thoughtfully with intention on something that makes your life bigger, deeper, weirder, or more memorable. For me, that might be a couch that didn't belong to the previous owners of our house. Take your kid to Japan. Buy the camera you've talked yourself out of for 7 years running. Go to that Michelin-starred restaurant and don't pretend to understand the menu. Just enjoy the absurdity of paying $38 for one single Romaine heart. Because if you've never practiced spending in alignment with your values, retirement will feel less like freedom and more like house arrest, maybe with better lighting. And nobody wants to be the millionaire who dies with perfectly preserved khakis and an unused national parks pass. So start now. Use your money like it means something because it does. Regret number two. They waited too long for happiness and missed it. There's a particular affliction in the wealthier people with whom I connect daily. It's subtle, sneaky, hard to diagnose at first. They look fine, they eat well, they use the word portfolio a lot, but deep down beneath the tax-optimized donor-advised funds and the 97-page estate plan written in lawyer hieroglyphics, there is a strange, quiet ache. They're still waiting to be happy. They don't say it out loud. They say things like, we're just waiting until the house is paid off, or once the kids are out of college, or we just need the market to stabilize. Quick side note, the market will never stabilize. And all of this is roughly the equivalent of saying, I'll go for a jog when gravity is less annoying. And what this all really means is, I'm postponing joy until it's somehow more convenient. So let's call this what it is. It's financial purgatory, a place where fun goes to die and spreadsheets go to multiply. And again, I get it. I've lived this. Well, I live this. I once spent six hours researching toaster ovens instead of calling a friend back. Not because I needed a toaster oven, but because I wasn't quite ready to be a person with nothing urgent to optimize. This is what psychologists call the arrival fallacy, the idea that happiness lies just over the next horizon. Once I get there, we think I'll relax, I'll slow down, I'll breathe, I'll buy that neon green bike I've had in my REI cart for four years. But the horizon, as it turns out, is quite rude. It keeps moving. And in the meantime, people build these elaborate life plans that hinge on one pesky little problem. Their future self is expected to be in perfect health, emotionally available, and just delighted to finally use those museum passes you bought in 2022 I've seen this go wrong so many times I could write a folk song about it. It would be called He Worked Till 67, then tore his rotator cuff at Disney, subtitled The Cruise Was Non-Refundable. The data here is brutal and clarifying. The average retirement age in America is about 63 The average healthy life expectancy, note, not life expectancy, just the years you're mobile, energetic, and unlikely to pull something sneezing, is around 68 That's a five-year window, five. You know what else lasts five years? Your car loan, your fridge warranty, or your kid's obsession with Minecraft. And yet people plan their lives like they're going to be zip lining through Costa Rica at 93 I hate to break it to you, but Costa Rica is hilly, and zip lines are less fun when you need a lumbar cushion. Now let me be clear. I'm not suggesting you blow all your savings on a camel safari in Morocco just because your lower back made a weird noise when you stood up yesterday. But I am saying that if every single plan for joy is scheduled in your mental outlook calendar for some day after tomorrow, you may want to reschedule. Here's the actual tragedy. People save up their whole lives, and when they finally reach that magic number, something else always seems to go wrong. They were playing financial Tetris for 40 years, and now someone handed them a blank screen and said, Congratulations, it's time to feel fulfilled. And they just stare at it like it's a test they forgot to study for. I once had a client, we'll call him Bill, who spent the better part of 20 years grinding in finance. Wonderful guy, proud of his work ethic, had a beautiful spreadsheet that predicted his net worth within a margin of 200 bucks, which is either genius or a sign of mild madness. Anyway, he hit his number, retired, I asked him what he wanted to do. He said, and I quote, I'm going to alphabetize the pantry. And he did, almost every single day. He just kept tinkering with the system. First, he did it by item, then by brand. Then he thought better to do it by expiration date. I went to his house once and his wife whispered, please give him a hobby or a mild sedative. This is what happens when you spend your entire adult life waiting for later to begin. You reach it and have no idea what to do, or you can no longer do it based on your mobility or mental clarity or lack thereof. It's the Clark Griswold problem. He gets the family all the way to Wally World, only to find it's closed. And then you realize maybe it was never about the destination after all. So what's the solution? Honestly, once again, commit to spending what now I'll call some weird money. I only call it weird because we spend most of our lives finding reasons and creating excuses not to spend this money. So you should take your daughter to Paris instead of buying her another round of emotionally charged holiday sweaters. Fly your dad to the Red Sox in person instead of watching the same game with 11 seconds of lag over FaceTime. Or sign up for that writing class, pottery class, improv class. Yes, it'll cost $400 and no, it won't cash flow. But maybe it will unlock a part of you that's been curled up in the fetal position since 2006 We need to stop treating joy like a suspicious line item on our financial plan. Because if you wait too long, you won't just lose time. You'll lose the actual ability to enjoy what you've told yourself you're going to enjoy. And even if you're in good health, others that you love and wanted to share these moments with might not be. So don't get too used to waiting and used to postponing. Because if you do, all those dreams that were right around the corner are now blocked by a mobility scooter and a bad shoulder. Here's a quick new guideline for you to use starting today. If it's something you deeply regret not doing and you can afford it without sacrificing your future, do it now. Not next quarter, not after we reallocate, now, because the real goal isn't just to retire early or build generational wealth or reach some abstract version of enough. It's to have stories. And stories do not come from balance sheets. They come from moments that surprise you, challenge you, and crack you open in a good way. So go make one before your knees start making that clicking noise that alarms your dog.