Stingy Compassion, Quiet Misery, and High Achievers

And a Plea to Open Doors to Other People Who Need You.

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Let’s talk about the guy who has it all and feels like shit.

You know the one.

Big house. Nice car. Executive title. Lived-in leather briefcase. Probably drinks a $19 smoothie with collagen and sea moss.

And still?

Miserable. Hollowed out like a wasps’ nest.

How many years will it take for people to act on this fact—that someone faring better at work and financially might still need help?

But say that out loud, and you’ll get one of two responses:

1. “Boo hoo, must be so hard in your second home in Aspen.”

2. [Insert eye roll so hard it needs a chiropractor]

We offer oodles of compassion for the struggling artist, the burned-out teacher, the overworked nurse—and we should. That’s not the problem.

The problem is the false binary we’ve built around compassion.

As if empathy is a rationed commodity, and we used our monthly quota on the right kind of suffering.

The Hidden Bias in Your Compassion Algorithm

It goes like this:

• They have money.

• They have prestige.

• They were handed something I wasn’t.

• Therefore, they can’t suffer in a way that matters.

That’s not justice.

That’s lazy tribalism with a fake moral glow-up.

We’ve turned compassion into a zero-sum game, as if empathy has to be earned through visible lack. The less you have, the more love you deserve. The more you have, the more we assume you bought your way out of pain.

Except no one does.

And that’s the gutting truth of it.

Pain Isn’t a Pie Chart, And You Don’t Get a Bigger Slice Because Yours Looks Prettier

The reality? High achievement can hide suffering better than anything else.

• Success makes you less likely to ask for help.

• Wealth insulates you from real feedback.

• Power warps your sense of worth.

• And accolades? They become your prison.

You start optimizing for how to be impressive instead of how to be alive. And if you dare say, “I’m struggling,” people look at you like you just spit on their rent check.

We forget that measurable success—income, assets, resumes—is not the same as internal well-being. We forget that depression, addiction, emptiness, alienation, and self-loathing don’t care about your LinkedIn endorsements or your generational wealth.

Consider this perspective-warping research…

Asking for Help: A Tale of Two Delusions

Dr. Vanessa Bohns ran a devilishly clever experiment to uncover what’s going on inside our heads when help hangs in the balance—when we either need to ask or might be asked. It turns out that the difference between being the help-seeker and the potential helper is a cognitive illusion worthy of a Vegas magic act.

Imagine you’re stuck downtown without a phone. Or you’re about to blow off your final for a hot date. Or your paper is due, and it reads like a drunk goat wrote it. Or you're woozy on a train and need a seat before you collapse onto a hipster’s tote bag. In these scenarios, you could ask someone for help. But if you're taking the perspective of the help-seeker, you suddenly transform into a self-conscious, over-apologizing gremlin convinced you’re about to ruin someone’s day. You believe asking for help is wildly inconvenient, possibly offensive, and unwelcome. You think you’ll seem weak. Or needy. Or like you just emerged from the underworld with no Uber account and zero pride.

Now in the helper’s shoes, things look laughably different. You're thinking, "Yeah, of course I'd lend my phone. It's no big deal." You're not annoyed. You're not judgmental. You’re not sitting there tallying how selfish the request is. Most of the time, you feel flattered. Needed (source). Like a decent human being with five minutes to spare and a soul.

Help-seekers dramatically underestimate how willing others are to help and overestimate how awkward the ask will be. Helpers? The opposite. They predict the ask is coming and that it’s fine.

Psychological insight?
When we’re the ones in need, we imagine ourselves as burdens. When we’re in a position to help, we imagine ourselves as heroes. The ego flips roles like a bad improv actor. This mismatch leads people to avoid asking for help—not because others are unwilling, but because we’re trapped in a distorted funhouse mirror version of social reality.

So the next time you’re sweating through your shirt about asking to borrow a phone, bum a ride, or get a set of eyes on your disastrous term paper, remember: you’re not begging for survival rations. You’re giving someone a chance to feel useful.

And that’s something we all secretly want.

The Doors You Can Open

This is one reason I adore the recent book by one of my favorite sources of intelligent provocation on social media, Dr. Rosalind Chow. She flings scientifically informed wisdom like a truth grenade into your cubicle and dares you to come out changed.

Her first book, The Doors You Can Open, is not your typical corporate kumbaya about mentorship.”That’s cute. Chow burns the pleasantries and talks about sponsorship—the bold, human act of putting your social capital on the line to open doors for someone else. Instead of advising from the sidelines while sipping your oat milk latte, you get in the game, throwing defensive elbows if needed, and saying, “Yeah, I vouch for them. Let them in.”

Why does this matter? Because mentorship is safe. Sponsorship? It costs something. And that’s what makes it morally thrilling. It turns you into the kind of person who isn’t just good at the game but who changes the game—for colleagues, friends, and frankly, anyone whose talent exceeds their access.

If you’re even remotely interested in being a better human at work—or just less of a self-absorbed bystander in life—click the link, crack the spine, and get to work.

👉 The Doors You Can Open

Put an end to wafer-thin diversity initiatives. Increase your meaningful social contributions. Get the guide here: link.

Why We Fill in the Blanks (Wrong)

Humans are pattern-hungry animals. We want a tidy narrative. So when we see a well-dressed, high-functioning person, our brain reaches for the nearest cultural Mad Libs:

“Nepo kid.”

“Daddy’s money.”

“Privileged male.”

“Crypto douche.”

“Snake in suits.”

“Mommy blogger with a nanny.”

“Trust fund burnout.”

And maybe some of that is true. But since when did someone’s tax bracket determine whether they’re worthy of being cared for? When did it become okay to allow irrelevant variables (height, weight, race, aversion to soup dumplings) to determine whether someone hurting is worthy of our help (our sponsorship)?

Here’s the sickest twist:

We don’t just fail to offer compassion. We resent their request for it.

As if they’re stealing something from us.

Imagine If We Did Science Like This

Imagine if your favorite antidepressant only had to prove effectiveness in people with an income under $50k.

Or if we said, “Well, it doesn’t help rich people, so we can’t count that data.”

You’d lose your shit.

We hold medical science to rigorous, nonpartisan standards of evidence. (At least in theory - see

Steve Stewart-Williams

and how political ideology melts scientists brains - here).

Can we please try to hold our emotional lives to a higher bar?

We Need a Better Moral Metric

One that doesn’t use:

• Net worth as a shortcut for worthiness.

• Proximity to your personal politics as a prerequisite for empathy.

• External suffering as the only valid kind.

Yes, it’s easier to measure assets than agony.

Yes, it’s simpler to feel for people who look like us.

Yes, it’s comforting to believe that pain and privilege cancel each other out.

But comfort is not the goal. Truth is.

And the truth is messy. It’s unfair. It doesn’t fit on a protest sign or an Instagram quote card.

An Alternative? Radical Compassion That Doesn’t Need to Be Justified

Because here’s what’s really punk rock:

Caring about someone before you’ve audited their pain for political and social ROI.

We don’t need to like everyone.

We don’t need to absolve assholes.

But we do need to stop pretending we can tell, from the outside, who deserves to be seen and soothed.

So here’s your uncomfortable homework:

• Listen to the miserable managing director without flinching.

• Ask your successful friend how they’re really doing—and believe them when they say, “Not great.”

• Make space for the high achiever who feels lost. Don’t interrogate their resume first.

Because pain doesn’t ask for permission.

And neither should your empathy.

Below is my attempt to help you do something impactful with that great work above by Drs. Vanessa Bohns and Rosalind Chow (link).

Radical Compassion Worksheet

Uncomfortable Questions for Self-Reflection. Use this for yourself. Break people into pairs or small groups and have them discuss these provocations in your classes/workshops - on values, social relationships, kindness, or curiosity.

1. When are you at your happiest, and who would roll their eyes at your answer?

2. Do you want peace, or just victory in your imaginary social class war?

3. What do you secretly want that someone richer already has?

4. Which kind of success do you trust more—yours or someone else’s you haven’t forgiven?

5. If money fixed everything, why do so many of your favorite artists die in rehab or alone?

6. How many compliments would it take for you to stop self-denigrating yourself for a week?

7. Whose suffering would you never retweet, and why?

8. Which type of pain makes you generous, and which type makes you cruel?

9. Would you still think you’re a valued contributor if no one clapped when you gave your opinion?

10. Who do you mock because you’re afraid of becoming them?

11. What invisible loneliness do you keep just beneath the clever punchline?

12. If the world saw your bank account, would they think you’re happy? Would they be right?

13. If compassion came with a receipt, would you check the balance first?

14. Whose joy triggers your insecurity the most?

15. What’s your favorite excuse for being an unkind bastard to someone you envy?

16. Which version of yourself gets your full compassion—and which one gets ignored until they break?

17. If someone else’s suffering threatens your moral narrative, do you mute them or listen harder?

Like many areas of psychology, what Dr. Rosalind Chow talks about might be bred in the bone but it still malleable. Both are true.

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Todd B. Kashdan is the author of several books including The Upside of Your Dark Side (Penguin) and The Art of Insubordination: How to Dissent and Defy Effectively (Avery/Penguin) and Professor of Psychology and Founder of The Well-Being Laboratory at George Mason University.

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