How to Disappoint People

A Beginner’s Guide

Photo by Vitaly Gariev on Unsplash

I work with a lot of talented, creative people who are also very generous with their gifts. They say yes to every collaboration, do favours left, right and centre, and requests for “Can I pick your brain?” are usually met with a “Sure.” Some of them have made themselves so available that their own creative work has started to exist in the margins (often late nights after everyone else’s needs are met, and that’s part of the reason they come to me).

If this sounds familiar, this post is for you.

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When I say “disappointing people”, I’m obviously a bit sarcastic. I don’t think of it as some character flaw (“being a meanie”), but rather of a skill to develop. And for those of us in creative fields, where boundaries are often a bit fuzzy and requests can sometimes be worded like “opportunities”, learning this skill isn’t optional in my view.

The Hidden Cost of Never Saying No

In my practice, I often see a particular kind of exhaustion, like the bone-deep fatigue of people who have become everyone’s go-to contact. They near always say yes and always manage to make time somehow (even if they don’t really have it—which just means it usually comes off their own downtime). They come to therapy not because they’ve done something wrong, but because they’ve done everything “right”. For everyone, except maybe themselves…

But every time we say yes when we mean no, we’re making a proverbial withdrawal from our own reserves to make a deposit in someone else’s account. We can tell ourselves a million times we’re being generous, but generosity requires choice. It’s not the same as self-abandonment.

I have writers in therapy who haven’t written anything in months, and not because they have writer’s block. It’s because their calendars are full with mentoring emerging writers (and they are not editors, to say this very clearly), beta-reading for friends, writing blurbs for acquaintances, and serving on literary nonprofits. They’re so busy with writing-adjacent things that they… never actually write. And when I ask why they don’t say no to any of these requests, they initially look at me as if I’ve got two heads, and reasons range from “people are counting on me” to “because I said I would” or “it might come in helpful for myself one day.”

But this isn’t just about neglecting our boundaries. It’s often about losing our sense of what we’re here to do in the first place. And slightly uncomfortable truth-bomb here: People-pleasing doesn’t actually work in terms of furthering a career because it’s, at its root, a coping mechanism that is sometimes about our need of approval and/or validation, sometimes about our own fears of rejection, sometimes about our own traumas. And sometimes about a combination of all of those.

But even if you say yes to everything, twist yourself into a pretzel and never utter a word of complaint, you will still disappoint people. You’ll “disappoint” them by not reading their minds quickly enough, by having the wrong artistic vision, by succeeding when they wanted you to fail (unfortunately that’s a thing), or by failing when they expected you to succeed.

It’s impossible not to disappoint people at some point, and many of the artists we respect most will probably have done so at some point during their careers: They’ve turned down projects that didn’t align with their vision or made choices that prioritised their creative integrity. Is that really what makes us lose respect?

The same is true in reverse. The people who genuinely support your work don’t need you to be infinitely available. They need you to be honest and do your best work sustainably. A creative community built on constant self-sacrifice and “helping out” for free or exposure isn’t a community (and I’ve seen quite a few of those over the years, and if you dare to say something about it, you get passive aggression at best and get shunned at worst—but maybe that’s actually not bad, because you’re really better off without being taken advantage of under the guise of “community”).

What Does “No” Actually Mean?

Saying no is a skill, and like any skill, it requires practice. But before we can practise, we need to unlearn some deeply embedded beliefs about what saying no actually means.

Saying no does not mean you don’t care. It means you care about multiple things, including yourself, and you’re making choices about how to allocate finite resources. No is not the opposite of generosity, even if some people may want to guilt-trip you into believing it is.

I work with singers who spent years saying yes to every gig, every collaboration request by every “friend-of-a-friend”. They were working constantly but had no time for what they really wanted to do (which varied case-by-case). When they finally started declining work, it felt initially uncomfortable, and they often over-explained everything. “I can’t do that session because I’m working on my album and also I promised myself I’d prioritise my own music and I’ve been really burned out…”

No is a complete sentence, folks. Not always a comfortable one but a complete one nonetheless. You can add context if you want (sometimes it’s kind to do so), but you don’t owe anyone a defence of your limitations.

You can simply say:

“I appreciate your thinking of me, but I can’t take that on right now.”

“That doesn’t work for me, but I hope you find the right collaborator.”

Notice what these don’t include: apologies for existing, elaborate justifications, or promises to make it up somehow. They’re just clear, and nothing about them is unkind or abrasive.

When you first start “disappointing” people, it feels terrible. Nervous systems used to years of people-pleasing will sound every alarm. Your brain will generate catastrophic scenarios: You’ll imagine your entire professional network collapsing and every new opportunity evaporating.

But that isn’t discomfort evidence that you’re doing something wrong. It’s only evidence that you’re doing something new.

Unfortunately, for us comfort-seeking humans, growth and comfort often don’t coexist in the same moment. The feeling of anxiety when you set a boundary is a sign that you’re challenging an old pattern. Your body is rebelling against the loss of its familiar coping mechanism, even if that mechanism was slowly destroying your (creative) life.

The discomfort does lessen with practice. The first no might feel like jumping off a cliff, the tenth feels only feel like stepping off a curb. But you have to be willing to feel the fear and do it anyway, trusting that the short-term discomfort is worth the long-term freedom.

Who Gets Angry When You Set Boundaries?

I always recommend to clients (and myself 🤣) to pay attention to who gets most upset when you start setting boundaries, because not everyone will respond the same way.

Some people will be momentarily surprised, then adjust. They might even express relief because your newfound honesty gives them permission to be more honest, too. These are people who truly want a relationship with, not just favours from, you.

Others will escalate. They’ll guilt-trip, criticise or threaten to withdraw their support. They’ll tell you you’ve changed (and maybe you have, but that’s the point). They’ll try to make you feel bad by telling you about how helpful you used to be (translation: how useful you were to them). They’ll make your boundaries about their feelings rather than respecting your limits.

And that’s telling you that the relationship was built on your compliance, not on mutual respect. NB: It doesn’t necessarily mean the relationship has to end, but it does mean it needs to transform. Otherwise, chronic resistance to your boundaries, especially when coupled with manipulation or guilt, is a red flag. End of.

You’ll definitely learn to distinguish between boundaries that are essential to your wellbeing and moments where more flexibility serves your values, so this is not advocating for a transactional approach to creative community where you never go out of your way for anyone. Sometimes the most meaningful thing you can do is show up for someone, even if it’s inconvenient in the moment. But the key word is “sometimes.”

The question I have always encouraged clients to ask is:

“What am I saying yes to when I say no to this?”

If saying no to a collaboration means saying yes to your own creative projects, to rest, or to work that actually pays, that’s a good trade. If you’re saying no just to prove you can, or out of resentment, that’s worth examining.

All of this also means being really clear about your values. If I take myself as an example (and I’m obviously not other people): I’m usually fairly okay with going the extra mile for people whose hearts I know, for emerging artists I genuinely want to mentor and for projects that feel creatively alive to me. But I’m not inconveniencing myself (anymore) for exposure-only opportunities and for people who habitually disrespect my time. All of that turns nto an even bigger No if they don’t even take the time to build up a relationship.

When you set boundaries, you’re not taking something away from your creative community. You’re giving them the gift of your honest presence instead of your resentful compliance.

Would you rather collaborate with someone who’s wholeheartedly engaged, or someone who’s physically present while mentally cataloguing all the things they’d rather be doing?

When you stop over-functioning in your creative community, you create space for others to step up. You invite reciprocity. You model what it looks like to treat your own work with respect. And you make room for collaborations that are actually sustainable rather than ones that run on people’s gradual depletion.

Trading relationships that are built on your usefulness for ones built on mutual care and creative exchange is always worth it.

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Thank you for reading this far—there’s really so much amazing stuff on here, so I truly appreciate it. If what I write resonates in any way, a comment, restack or like is really welcome…

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If you’re reading this thinking, “I’ve tried setting boundaries before and it didn’t work,” I want you to know that boundary-setting isn’t a one-time event. It’s a practice you’ll return to forever, in different projects and contexts.

You’ll have moments where you revert to old patterns. You’ll say yes when you meant no, or explain when no explanation was needed. You’ll feel guilty for disappointing someone who has historically relied on your inability to set limits. This is all part of the process.

The goal is not perfection but a creative life where yeses (is that even a word? 🤔🤣) mean something because nos are possible. Where collaborations aren’t based on unspoken obligation.

We don’t have to be everything to everyone.

A Final Thought

As I already mentioned: The title of this guide is deliberately provocative, but learning to disappoint people isn’t really about disappointment at all. It’s about external choices aligning with our internal values and recognising that we are not an infinite resource, and that our limitations are not moral failures.

Some people will be disappointed when you change. But their disappointment is not your responsibility to fix, and their inability to respect your boundaries is not evidence that you’ve set the wrong ones.

You are not required to metaphorically set yourself on fire to keep others warm. Learning to disappoint people is really learning to live like your work matters.

And it does.

The people who value your work will stick around. The ones who valued you only for what you did for them might not. But that’s not a loss. It’s just gaining clarity, and sometimes, that hurts a bit initially. Just like ripping off a bandaid to give your skin the chance to breathe.

I’ll leave you with this:

What’s one small no you’ve been avoiding? What would become possible in your creative practice if you finally said it?

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