Welcome back to another Question of the Week here at The Confusing Middle! After spending the last three weeks exploring various flavors of public humiliation (because apparently Gregory Stock really wanted us to confront our deepest fears), we’re shifting gears to something a little different. Instead of asking what we’d endure, this week we’re exploring what we’d give up.

This week’s question: Would you accept an inflation-adjusted lifetime stipend of $150,000 per year if it meant you couldn’t earn or inherit additional money? What would be the lowest such stipend you’d agree to?

The Easiest Question Gregory Stock Has Ever Asked

Let me save you 1,500 words: Yes. Absolutely yes. Where do I sign? Do you need it notarized? Should I bring my own pen? Is there a line, because I’ll camp out overnight like it’s Black Friday and this is the last PlayStation 5 on Earth.

Seriously, this might be the fastest I’ve ever answered one of these questions. Usually, I need to wrestle with moral implications, weigh pros and cons, consider various scenarios. This time? The only wrestling happening is me trying not to seem too eager when I accept this deal, like playing it cool when that girl you liked in high school asked to borrow a pencil.

Here’s the thing: I work for a non-profit. I knew what I was signing up for when I chose this path—meaningful work, making a difference in early childhood education, and a salary that ensures I’ll never have to worry about paying excessive taxes on my yacht because, spoiler alert, there will never be a yacht. I’m not complaining (okay, maybe a little), but let’s just say that six figures might as well be seven figures for how achievable they feel from where I’m sitting.

So when someone offers me $150,000 a year to essentially exist? That’s not a philosophical dilemma. That’s winning the lottery without having to buy a ticket.

Let’s Talk Numbers (Or: How I Learned to Stop Worrying and Love Basic Math)

One hundred and fifty thousand dollars. Per year. Adjusted for inflation. Forever.

I need you to understand that this is roughly—checks notes—way more than I make now. Way more than I’ll probably ever make. Unless United Way suddenly decides that coordinating early childhood education programs should be compensated like playing shortstop for the Yankees, I’m pretty sure my salary ceiling is somewhere south of this offer.

Let me put this in perspective for you. With $150,000 a year, that’s $12,500 per month. My current monthly budget for one single person living in Roanoke, Virginia? Let’s just say it’s… not that. Not even close to that. I could pay my current monthly expenses and still have enough left over to develop expensive hobbies, like collecting vintage typewriters or… I don’t know, eating at restaurants that don’t have drive-throughs… Filling the gas tank all the way.

The question asks what the lowest stipend I’d accept would be. Honestly? I could live comfortably on half of what they’re offering. Seventy-five thousand a year would still be a significant upgrade. But if someone’s offering $150,000, I’m not going to negotiate myself down. I’m not that noble.

The Geographic Lottery

Now, I realize that my enthusiasm might be influenced by the fact that I live in Southwest Virginia, where the cost of living is what people in San Francisco would call “adorably quaint” or possibly “fictional.” My mortgage payment here might cover a parking space in Manhattan. Maybe half a parking space.

The dollar stretches further here in Roanoke than it would in Northern Virginia, where apparently they’ve decided that townhouses should cost as much as small countries. Here, $150,000 a year isn’t just comfortable—it’s “I can shop at Whole Foods without checking my bank balance first” money. It’s “I can get guacamole at Chipotle without hesitation” money. It’s “I can subscribe to all the streaming services and actually remember I have them” money.

But even if I lived somewhere more expensive, this deal would still be incredible. Sure, $150,000 might not go as far in Los Angeles or New York, but it’s still a guaranteed income that’s adjusted for inflation. Forever. Do you know what most of us have guaranteed? Nothing. Absolutely nothing. Companies fold, positions get eliminated, entire industries disappear. But this magical stipend? It just keeps coming, like a financial Groundhog Day except instead of Bill Murray learning piano, I’m learning what it’s like to not check my bank balance before buying name-brand cereal.

The “But What Would You DO?” Chorus

I can already hear the objections. “But Aaron,” you say, “wouldn’t you be bored? Wouldn’t you miss the satisfaction of earning your money? Don’t you want to contribute to society?”

First of all, bold of you to assume I find satisfaction in earning money. I find satisfaction in having money, sure. But the earning part? The waking up to an alarm, the meetings that could have been emails, the emails that somehow became meetings, the commute, the office politics, the annual performance reviews where we pretend that a 2% raise is keeping up with inflation? I could probably learn to live without all that.

As for being bored—are you kidding? Do you know how many books I haven’t read? How many movies I haven’t watched? How many blog posts I could write without worrying about squeezing them in after work? I could actually finish my next novel without falling asleep at my keyboard at 11 PM.

And contributing to society? Who says I’d stop? The question just says I can’t earn additional money. It doesn’t say I can’t volunteer. I could still work with early childhood education programs—I just wouldn’t need a paycheck. I could write for the pure joy of writing. I could help people because I want to, not because I need to pay rent. Imagine how much more you could contribute if you weren’t exhausted from contributing for survival.

The No-Earning Clause (Or: The Part Where People Panic)

The restriction is that you can’t earn or inherit additional money. For some people, this is apparently a deal-breaker. These people clearly make more than $150,000 a year, and frankly, I don’t have a lot of sympathy for their “problem.”

But let’s examine this restriction. No earning money means no side hustles, no passive income, no selling things on eBay. For me? Not an issue. My current side hustle is writing, and let’s be real—the chance of me suddenly becoming the next Stephen King is about as likely as me becoming the actual next Stephen King through some sort of consciousness transfer experiment.

If I need to get rid of stuff, I’ll just list it for free on Facebook Marketplace. I’ll be the hero of local bargain hunters. “Free couch! Free bookshelf! Free vintage typewriter!” (Okay, maybe not the typewriter. I’m not made of stone.)

The inheritance part is even less of an issue. I’m not exactly from old money. I’m not even from new money. I’m from “let’s check if we have a coupon for that” money.

The “What’s the Catch?” Investigation

This deal seems too good to be true, which means my cynical brain is searching for catches like I’m looking for Waldo if finding him meant financial security.

Maybe the catch is psychological. Maybe without the need to work, we’d all spiral into existential crises, lying on our couches at 2 PM on a Tuesday, eating cereal from the box while watching our fourteenth consecutive episode of something we’re not even enjoying anymore.

Except… isn’t that what weekends are? And vacations? And we seem to handle those just fine. Better than fine, actually. We live for them. The only difference is this would be permanent weekend. Permanent vacation. Permanent “sorry, I can’t come to that meeting because I don’t have meetings anymore.”

Or maybe the catch is social. Maybe we’d lose our identity without our jobs. “What do you do?” is usually the second question people ask after your name. But I could answer that question. “I write. I volunteer. I travel. I read. I live.” Sounds a lot better than “I coordinate spreadsheets and attend meetings about having meetings.”

The People Who Would Say No (And Why They’re Wrong)

I suppose there are people who would turn this down. People who already make more than $150,000 and can’t imagine downsizing their lifestyle. People who define themselves entirely by their net worth. People who think luxury is a necessity rather than a… well, luxury.

To them I say: really? You need more than $150,000 a year to be happy? What are you buying? Are you eating gold? Is your car made of other, smaller cars? Do you have a subscription service for subscription services?

There’s something to be said for “enough.” And $150,000 a year, adjusted for inflation, forever? That’s not just enough. That’s more than enough. That’s “enough” with a comfortable cushion, a safety net, and a little umbrella in case it rains.

The Freedom Factor

What this question is really asking is: would you trade the possibility of unlimited wealth for the guarantee of more than adequate wealth? Would you give up the lottery ticket for the guaranteed payout?

Yes. A thousand times yes. Because here’s what that guarantee buys you: freedom. Freedom from worry about layoffs. Freedom from staying in a job you hate because you need health insurance. Freedom from the Sunday night dread. Freedom to pursue passions that don’t pay. Freedom to take risks that aren’t financial. Freedom to help others without wondering if you can afford to.

That’s not selling out. That’s buying in—to a life where your value isn’t determined by your salary, where your time is actually yours, where you can wake up and ask “what do I want to do today?” instead of “what do I have to do today?”

Your Turn

So what about you? Would you take the $150,000 deal, or are you holding out for the chance to become a billionaire? What’s the minimum you’d accept to give up the rat race—assuming you’re even in the rat race and not, like some of us, in more of a hamster wheel situation?

Are you one of those people who actually loves working? Who would miss the grind? Who thinks that earned money somehow feels better than free money? (If so, please explain this to me, because I’ve had both birthday money and paycheck money, and they spend exactly the same.)

Drop your thoughts in the comments below. Tell me why I’m wrong to jump at this opportunity. Convince me that there’s nobility in the struggle that I’m missing. Or just admit that you’d take this deal too, and we can start planning what we’d do with all our free time and financial security.

Until next week, when Gregory Stock will hopefully ask us something that doesn’t involve money, humiliation, or moral quandaries (though at this point I’m not holding my breath), this is Aaron, still here in The Confusing Middle, already mentally spending my hypothetical $150,000, and genuinely curious if anyone would actually turn this down.