How to Disappoint People and Still Sleep at Night

The beautiful, ordinary practice of gentle defiance.

The text arrives at 10:47 PM on a Wednesday: "Hey! My flight lands at 6 AM Saturday. Could you maybe swing by and grab me? I know it's early but you're such a lifesaver!"

I'm already typing "Of course!" before my brain catches up with my fingers.

Six AM. Saturday. That's my only morning to sleep in this week. Three-hour round trip to the airport. But my thumbs are already committed to the performance, muscle memory from decades of being the person who says yes before thinking, who prioritizes other people's convenience over his own rest.

I hit send and immediately feel that familiar ache. Not exhaustion, but something more profound. The hollow feeling of betraying yourself in real time.

When did I become the person who treats his own time like a public resource?

The Audition I Never Remembered Taking

I've been thinking about how we become the accommodating friend or family member. I don’t think it happesn overnight. It's more like method acting. You slip into the role so gradually that you forget you're performing.

Somewhere, sometime, someone asks for a favor and you say yes. They're grateful, effusive even. It feels good to be needed, to be the reliable one. So you say yes again. And again. Before you know it, you're the person people call when they need last-minute help, airport runs, emergency dog-sitting, someone to listen to relationship drama at midnight.

You've trained them to expect this availability from you.

The costume becomes familiar: always having your car keys within reach, your phone charged and ready for urgent requests. The dialogue gets easier: "No problem at all!" delivered with enthusiasm that never quite reaches your actual feelings. You perfect the emotional range required—endless patience, unwavering helpfulness, cheerful availability that feels increasingly hollow.

Here's what I've realized about this particular performance: the audience starts believing it's who you actually are.

And after a while, so do you.

I think about my friend Jake, who calls me his "lifesaver" because I've driven him to three different airports, helped him move twice, and listened to him dissect the same job frustrations for six years. The gratitude feels genuine, but there's something else underneath—an expectation that I'll always be available for the next crisis, like I'm a utility service he can depend on.

When did being helpful become my entire personality? When did I agree to be the human equivalent of AAA?

The Theater of Self-Erasure

We've confused being helpful with being human. As if our worth is measured by our willingness to dissolve into other people's convenience. As if saying no were a character defect rather than a basic life skill.

This hits me as I'm calculating the logistics of Saturday morning. Set my alarm for 5:15 AM. Skip my usual coffee ritual that centers me for the day. Rush through traffic to arrive precisely when their flight lands, because heaven forbid they wait ten minutes for a ride they didn't pay for.

But here's the part that makes me feel slightly sick: I'm not just saying yes to the favor. I'm saying yes to the entire identity I've constructed around being endlessly accommodating. The person who never has conflicts because he never has preferences. The friend who's always available because he's never quite busy enough with his own life to justify saying no.

I'm performing a version of myself that prioritizes everyone else's comfort over my own aliveness.

The performance has become so seamless that I've forgotten it's a choice. I've turned myself into emotional infrastructure for other people's lives while treating my own needs like optional add-ons.

That night, I lie awake thinking about all the Saturday mornings I've sacrificed for this performance. Not just the airport runs, but the birthday brunches when I wanted to stay home and read, the dinner parties where I smiled through conversations that felt like verbal quicksand, the countless times I've said "Whatever you want!" when asked what I preferred, as if having preferences were somehow evidence of selfishness.

When did I decide that my rest mattered less than their convenience? When did I start believing that my time was worth less than everyone else's?

The answer comes to me around 2 AM: I never consciously decided it. I just drifted into it, one accommodating gesture at a time, like I’m the crab in slowly boiling water that never notices it's cooking… until its too late.

Breaking Character

Saturday morning arrives gray and drizzling, which feels appropriate for the death of my sleep. I'm in my car by 5:45, driving through empty highways while the rest of the world enjoys the radical concept of rest. My friend texts updates about delayed baggage claim, apologetic but not QUITE apologetic enough to suggest I just go home and he'll figure it out like a functioning adult.

Standing in the pickup zone, watching other people hug their arriving passengers, something crystallizes for me. I'm not here because I want to be. I'm not even here because I should be. I'm here because I've convinced myself that saying no would reveal me as fundamentally defective.

But what if disappointment isn't abandonment? What if it's actually a form of respect, treating people like capable adults who can handle minor inconveniences without falling apart?

What if the real disrespect is assuming they can't?

Three months later, the text comes again. "Flight lands at 5:30 AM Tuesday. Dude, you’d my hero if you can swing it!"

This time, I stare at the message for a full minute before responding. I can feel the old performance trying to activate…the automatic "Of course!" that wants to tumble out of my fingers. But something has shifted.

"Can't make it work this time, but there is always uber! Let’s grab a drink sometime and catch up on your most recent adventure."

I hit send before I can change my mind, before I can spiral into justifications about why my Tuesday morning matters.

The response comes twenty minutes later: "No worries, man! Thanks anyway. Of course - maybe this weekend?"

That's it. No guilt trip. No dramatic disappointment. No friendship-ending crisis. Just a normal human being handling a minor inconvenience like a normal human being.

I sleep until 8 AM that Tuesday and wake up feeling something I haven't felt in years: respect for my own boundaries.

That morning, something shifted for good.

The Revelation Nobody Warns You About

Here's what they don't tell you about disappointing people: most of the catastrophic outcomes you imagine live entirely in your head.

I spent years convinced that saying no would result in damaged relationships, hurt feelings, evidence that I was fundamentally selfish. I carried around this mythology that good people never disappoint anyone, that love and care mean endless availability, that boundaries are just selfishness dressed up in therapy language.

But when I finally started disappointing people, something unexpected happened.

Nothing fell apart.

The people who truly cared about me adjusted. They found other solutions, made different plans, or simply accepted that I wasn't available. The people who got angry or manipulative about my boundaries revealed themselves as people who valued my accommodation more than my wellbeing.

Both outcomes were useful information.

I think about that Tuesday morning when I chose sleep over service. How I made coffee in my own kitchen instead of rushing through traffic. How I read three chapters of a book instead of making small talk in airport pickup lanes. How I treated my morning like it belonged to me instead of like it was public property anyone could claim.

I didn’t have capacity that morning for that added stress. I just didn’t. Especially at the last minute. And I listened to myself.

Disappointment, it turns out, is a form of honesty. It's admitting that you have limits, preferences, a life…just like every other human out there. It's trusting that the people who love you can handle the reality of your humanity, including the inconvenient parts.

And I’m left with a truth: boundaries aren't walls you build to keep people out. They're clarity you provide about what you're actually available for.

The Practice of Gentle Defiance

Now when I get those late-night requests, I pause. Not just a hesitation—a full stop. I put the phone down and ask myself the questions that used to terrify me:

• Is this request coming from their emergency or their poor planning?

• Am I saying yes because I want to help or because I'm afraid of what happens if I don't?

• What would I tell a friend to do in this situation?

There's something that feels, sometimes, almost violent about typing “Can't make it work this time.” my chest tightens, my thumb hovers over send like I'm about to detonate something. But then I hit send and feel this rush of, relief, maybe? Like I've finally told the truth about something I'd been lying about for years.

Sometimes I still say yes, but from choice rather than compulsion. When I want to help, when it works with my actual schedule, when the generosity feels genuine rather than obligatory. When it comes from aliveness rather than from the hollow space where my boundaries used to be.

Other times, I say no. Kindly but clearly. "Can't make it work this time." No elaborate explanations about why my time matters, no apologies for having boundaries, no justification for treating my own life like it belongs to me.

The disappointing people part gets easier with practice. The sleeping at night part was immediate. That might sound weird, given that saying no should create anxiety. And there was some. But there's so much more anxiety wrapped up in all those automatic "yes" responses that the net effect on my sleep was profound improvement.

Because here's what I've learned about disappointment: it's not the end of the world. It's not even the end of relationships. It's just information about what you're available for and what you're not.

Most people, it turns out, are perfectly capable of handling that information like the adults they are.

The Beautiful Ordinary of Boundaries

These days, my Saturday mornings belong to me. Coffee that I make slowly, books that I choose, conversations with myself that nobody else needs to overhear. The revolutionary act of treating my time like it has value.

My friendships haven't suffered from my newfound boundaries. If anything, they've improved. When I show up now, it's because I want to be there, not because I'm trapped by a performance I can't escape. My presence feels more genuine because it's more chosen.

The people who love me have adjusted to the reality that I'm not endlessly available. They make backup plans, consider my schedule, ask rather than assume. The people who couldn't adjust revealed themselves as people who were more invested in my accommodation than my wellbeing.

Both outcomes were gifts.

The text that arrives now gets a different response. Sometimes it's still "Of course!" when the timing works and the generosity feels authentic. Sometimes it's "Can't swing it this time" when my Saturday morning feels more important than someone else's travel convenience.

Either way, I now sleep just fine.

This is where you start, if you're ready: with the small disappointments that don't feel world-ending. Decline the office potluck. Skip the group text about weekend plans. Practice the phrase "Not available this time" until it stops feeling like a foreign language.

Before responding to any request, ask yourself: "What would happen if I said no to this?" Usually the answer is: they'd figure it out, just like they did before you became their go-to solution.

Saying no is like any other skill—terrible and awkward at first, then surprisingly natural. The first few times felt like rebellion. Now it feels like basic self-respect.

Because disappointment isn't abandonment. It's a quiet, loving insistence that your rest matters just as much as their comfort. It's trusting other people to be capable adults who can handle minor inconveniences without your constant rescue.

It's the radical recognition that you're not responsible for managing everyone else's emotions at the expense of your own aliveness.

Congratulations on disappointing someone—and finally, not disappointing yourself.

Your Saturday morning was always yours to give or keep. The revolutionary act is remembering you have a choice.

A Small Ask

If this resonated with you—if you found yourself nodding along or feeling that familiar ache of recognition—would you consider sharing it with someone who might need to read it?

I think there are people in your life who are still driving to airports at 6 AM when they'd rather be sleeping. People who've turned themselves into emotional infrastructure for everyone else's convenience. People who need permission to remember that their Saturday morning was always theirs to give or keep.

Sometimes the most radical thing you can do is help someone else remember they have choices too.

Coming on Thursday

For paid subscribers, Thursday brings a deeper dive.

Introducing "Kindly Unavailable: Reclaiming Your Boundaries with Courage," a thoughtfully structured reflection where you'll explore the emotional patterns that lead you to sacrifice your own needs, accompanied by a downloadable workbook with journaling prompts, body-awareness exercises, customizable message templates, and affirmations.

Because sometimes we need more than insight; we need a roadmap.

About Alex

I’m Alex Lovell — political psychologist, yoga therapist, and writer.

Lived homeless. Been divorced. Survived a seven-car pileup with a semi. Fell in love with questions that don’t have easy answers. I’ve met a lot of thresholds. Even the one before death.

These days, I split my time between research, writing, and holding space for people figuring out who they are after everything shifted.

This Substack is where I make sense of things out loud.
I write for people in transition — between roles, beliefs, relationships, selves.
The ones quietly wondering, “What now?” but allergic to one-size-fits-all answers.

Sometimes I quote research. Sometimes I quote my own nervous system.
One speaks in data, the other in sensation. I’ve stopped choosing sides.

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