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

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 it's 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 Scheffler, 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 their 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 PhD, a trust fund, or a laminated Dave Ramsey envelope system.

Today we're tackling a question that almost no one 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 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 8 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 everything

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 okay, 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 ask 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 metals.

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 no 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 worldview.

And over time, that thrift becomes so calcified, calcified, it's not a choice anymore.

It's just who they are.

They're the kind of person who skips appetizers, who reuses tinfoil, who orders the cheapest wine, but acts like they did it on purpose because mulbex are getting too showy these days.

This is why some retirees, even wealthy ones, withdraw less than their 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 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 seven 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 kids' obsession with Minecraft.

And yet people plan their lives like they're going to be ziplining through Costa Rica at 93.

I hate to break it to you, but Costa Rica is hilly, and ziplines 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 someday 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.

Regret number three.

They retired from something,

not to something.

There's a moment, often about 11.15 a.m.

on the first Monday after retirement, when it hits.

The to-do list is done.

The inbox is empty.

Heck, you might not even have an inbox anymore because you got kicked off company email.

You've already cleaned the lint trap and eaten the emergency biscotti your neighbor gave you in 2016.

And now you're just, well, sitting there in stretchy pants, watching an ad for reverse mortgages and wondering if you've made a huge mistake.

That feeling, it's not just boredom.

It's the existential hangover of having no idea what you are or who you are without your calendar and your colleagues.

Because for years, decades even, your your time was structured.

You had meetings, reports, Monday bagels that were never actually good but gave you a reason to speak to Kyle from accounting.

You were somebody

doing something.

And then, poof,

it's gone.

Like the free office coffee you used to complain about, but now miss with a strange hollow ache, it's like being dumped by your schedule.

And the problem is no one tells you this is coming.

The retirement pamphlets all show a couple kayaking in matching vests, grinning like retirement is a sialis ad.

But what they don't show is what happens when the kayaking is over, and you're just two slightly damp people with no plan and too many hummus options in the fridge.

Here's what I've seen after two decades of connecting with people about money.

People assume that retirement is the destination.

but it's really a massive blank page, and most folks never learned how to plan for for filling that page beyond a three-week tour of Italy.

Instead, they spend their first year of freedom alphabetizing spices, wandering the aisles of Home Depot, or signing up for adult ed classes they have no business being in.

Now, don't get me wrong.

I'm all for learning new things in retirement.

But if your retirement plan can be summarized as maybe I'll finally read Infinite Jest, I'd like to politely recommend a backup plan.

Though, to be fair, I'd also recommend reading Infinite Jest, so you're reminded to stay away from spending the next 20 years watching Netflix.

Know that retirement is not a vacation.

It's not even a sabbatical.

It is an identity transplant.

You are no longer the teacher, the VP, the small business owner, the dentist with the waiting list.

And most folks don't even care that you once were.

Congratulations, you have officially lost that social clout that once clouded.

Now, you're just Carl, and Carl needs a reason to wake up that's not just, today's the day I finally fixed the drawer that squeaks.

Study after study confirms the following.

Retirees without purpose experience steeper cognitive decline, higher rates of depression, increased feelings of loneliness and regret, all because the one thing no one taught them to solve for was meaning in the absence of chasing work and money.

And this isn't just about older retirees.

I've had 30-somethings who took sabbaticals after tech windfalls text me six weeks later like, hey, is it normal to cry in the cereal aisle?

Yes, Derek, it is.

I do it daily.

You need to know this.

Purpose is portable.

but you do have to pack it before you leave the office.

If you don't believe me, just talk to anyone who tried to retire early and ended up back at work 18 months later.

Not because they needed the money, because they needed a reason to change out of sweatpants before noon.

Take a former client of mine, we'll call her Barbara.

She sold her business at 62, a wildly successful exit by anyone's standards.

The kind of payday you imagine might come with a confetti cannon and a permanent smug expression.

Six months later, she called me with an odd tone of panic.

I bought a boat, she said.

Oh, congrats, I replied.

I hate boats, she said.

Huh?

I hate boats.

I just needed something to do, and some of my neighbors have boats.

Now, I'm not anti-boat.

I'm anti-accidental boat.

I'm anti-people mistaking a purchase for a purpose.

So if you're five years out from retirement, or five weeks, ask yourself not just how much money you'll have, but how you'll spend your attention.

Because attention is currency.

It's the thing that makes you feel real, seen, useful.

And once the meetings are gone and nobody cares what you think about quarterly projections anymore, you need something else that makes your eyes light up.

Volunteer, mentor, build furniture badly, write postcards to voters, or join a trivia team and get irrationally competitive about 80s sitcoms.

It doesn't have to be noble.

It just has to be yours.

Because if you don't retire to something,

you'll feel like you disappeared the day you stopped getting reply-all emails about sandwich orders.

Let me leave you with this.

In the world's longest study of adult happiness, the Harvard study of adult development, Do you know what predicted fulfillment in later life?

It wasn't money.

It wasn't achievements.

it wasn't even your cholesterol.

It was relationships, purpose, and feeling useful.

So I ask you to retire like a writer, not someone closing the book, but someone starting a brand new chapter, a weirder, freer, slightly saltier one.

And for the love of all things holy, know that nobody, not a single person in the history of retirement, has found meaning in fixing that one weird light switch in the garage.

To recap, you saved for decades.

You skipped the lattes.

You maxed out the 401k.

For all intents and purposes, you made it.

And now you're here.

The here chapter that nobody prepares you for.

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 it's time.

And three, a calendar so empty it echoes and an existential identity crisis.

This is the part of your story where most people expect a triumphant symphony, but what they often get is a kazoo solo in an empty theater.

Because wealth, strictly financially speaking, is not the point.

An absence from your job is not the point.

The point is what you do with the newfound money and time that you now have.

Who are you going to spend it with and how awake are you going to be while it's happening?

Because if you spend your whole life treating joy like a dessert cart that only comes around once you've eaten all your vegetables, news flash, that cart sometimes breaks down or skips your table entirely.

So if you take nothing else from this episode, well, first of all, you've made it this far, which already puts you ahead of most people who clicked play thinking this was a true crime podcast.

but second of all take this

live now not recklessly but presently spend money on purpose spend time like it's more valuable than money because it is and plan not just for retirement but for aliveness starting today

that might mean opening an emergency spending account it might mean taking your spouse to that one place you always said you'd go someday it might even mean finally learning to kayak even if you capsize immediately and shout profanities at a duck.

Whatever it is, please do it because money is just a means to an end.

And if you don't define the end, the means never will feel like enough.

Thanks for tuning in to your money guide on the side.

If you enjoyed today's episode, be sure to visit my website at tylergardner.com for even more helpful resources and insights.

And if you are interested in receiving some quick and actionable guidance each week, don't forget to sign up for my weekly newsletter where each Sunday I share three actionable financial ideas to help you take control of your money and investments.

You can find the sign-up link on my website, tylergardner.com, or on any of my socials at SocialCap Official.

Until next time, I'm Tyler Gardner, your money guide on the side, and I truly hope this episode got you one step closer to where you need to be.