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This Reddit thread has every high earner rethinking their finances
Hundreds of 6-figure earners confessed the quiet mistakes draining their wealth — and the replies are uncomfortably relatable.
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If you make over six figures and still feel broke, you’re not alone (and now we have the receipts to prove it).
A trending Reddit thread recently asked a seemingly simple question:
“What’s your biggest money mistake as a HENRY?”
(HENRY = High Earner, Not Rich Yet. You earn $100K - $250K+, but your net worth feels like a rounding error.)
What followed was a financial confession booth that pulled back the curtain on what’s actually happening behind the paychecks of high-income earners.
The responses?
Shocking.
Relatable.
And way too common.
These weren’t horror stories. They were slow leaks.
No Vegas blowouts. No bankruptcies.
Just tiny, seemingly harmless mistakes (often repeated over years) that quietly torched people’s financial progress.
A few real replies:
“For me - I rolled over a couple of old 401ks into an IRA in early 2020 when I was between jobs. I’m a very “set it and forget it” investor, especially when it comes to retirement since I’m yearsssss away. Welp. It took me TWO YEARS to notice they were just sitting in cash, not invested. Two high growth years of compound interest lost cuz I wasn’t paying attention to my accounts. 😭”
“Probably when I cashed out my 401k during the '08 recession.
It was only 13k and I was so financially illiterate I had no idea what it was invested in (or really how I had a 401k. It was news to me when I got the paperwork) OR that cashing it out would have tax implications the next year.
The worst thing? I didn't even need the money, but the stock market was crashing and I had a vague idea that retirement accounts were "stocks" and I figured it would be better to have it in my bank account than vaporize on Wall Street.
It was a whole mess. I learned my lessons, but I wish that I had compounding money since my early 20's!”
“Not starting retirement savings earlier.
After HENRY status, sacrificing way too much savings to help family members. Now that I'm actively trying to find a different job and the job market is in shambles, having that extra ~$80k+growth in accessible investments/savings would have been enough for me to pull the ripcord and quit without an offer.”
No wild spending. No meme stocks (well… maybe a couple).
Almost all of the responses just came from smart people with good jobs who never got the manual.
What’s really going on?
As more people hit six-figure salaries, many are realizing the hard way that income doesn’t automatically lead to wealth.
The biggest problems?
They’re not flashy. They’re invisible:
Cash sitting idle in rollover IRAs or brokerage accounts
“Set it and forget it” investing that was… never actually set
Overpaying for advice they don’t use
Filing taxes without optimizing anything
Avoiding financial decisions because they feel intimidating or boring
In other words: it’s not about making bad decisions.
It’s about never making the good ones.
Why HENRYs are most at risk
HENRYs are stuck in a strange middle ground:
They make too much money to justify being disorganized…
But not enough to coast on mistakes.
And the pressure to look successful or the expectation to support family and friends (without knowing when they should really be saying “no”) only makes it worse.
What this thread exposed is that most high earners are:
Overworked
Under-optimized
Operating on autopilot
They’re working hard, earning more, and assuming the wealth will sort itself out.
It doesn’t.
A quick gut-check to avoid becoming the next Reddit confession
If any of these sound uncomfortably familiar, here’s a 5-step “I didn’t screw up (yet)” checklist:
Have you opened any retirement or brokerage accounts?
Check to see if the money is actually invested (e.g. you’ve allocated those funds vs. just sitting there).
Saving for later can also lower your taxes now.
IRAs, HSAs, Solo 401ks don’t just help you save and take advantage of compound interest. They can also strategically lower your tax bill.Search your advisor’s name + “AUM fee.”
You might be surprised what you’re paying… and what you’re getting.
Look at your cash balance.
What’s earning 3-4%+? What’s earning 0.01%?
Pull last year’s tax return.
Just scan it. Look at deductions. Ask what you missed.
Pick the one thing you’ve been avoiding.
The rollover. The Solo 401k. The question you keep pushing off.
Tackle it this week.
No spreadsheets. No five-hour YouTube rabbit holes.
Just one smart step. Then another.
TL;DR
These HENRYs didn’t all just blow their money.
They just drifted.
And in personal finance, drift can be expensive.
Not all at once.
Just slowly.
Until one day, you wonder where it all went.
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