Success Is Embarrassing (and other lies we tell ourselves)
Here’s a fun thing no one tells you about getting the things you want: it’s humiliating.
Not because you didn’t earn it, but because now everyone can see what you were aiming for. And maybe worse, they can also see that it mattered to you.
And let’s be honest: there are few things more deeply uncool than caring a lot.
In the last year, I managed to reduce my hours at a job I didn’t love, then quit entirely. I built a business. I launched a blog. I launched a podcast. The kind of things that, if you list them too cleanly, start to sound like an ad for Squarespace.
And I’m proud of all of it. But the second I hit “post” on anything related to it, I immediately want to duck behind a couch.
Because the moment you admit you care about something - really care - you become extremely visible. And visibility is awkward. Visibility means people can watch you win, sure, but it also means they can watch you fail. Or stall. Or get exactly what you said you wanted and still feel weirdly unfulfilled.
Which, incidentally, is where I’ve been for the past two weeks.
I handed my notice in at my job two weeks ago. Two. Weeks.
That is how long it took for me to start mentally backfilling my time with freelance listings and part-time roles I don’t need. Not because I want to do them. Not even because I need the money (yet). But because wedding season is slowing and I’ve apparently conditioned myself to fear free time like it’s carbon monoxide.
And sure, I could call that ambition. I could call it drive. But if we’re being honest, it’s just chronic productivity addiction with a decent brand voice.
The thing is, I was under the impression that “success” - however loosely defined - would come with a sense of arrival. Or at least a faint smell of clarity. I assumed that once I’d built something that worked, the doubt would die down, the anxiety would take a seat, and I’d feel... steady. Capable. Grounded in my own vision.
What I got instead was the same overthinking, but with slightly better analytics.
Because here’s what no one says out loud:
Once things start working, you lose your favourite excuse. You can’t say “I’m stuck” or “It’s not happening yet” or “I’m still figuring it out” - at least not without lying. You are doing it. People are noticing. And if you still feel unsettled? Well. That’s a much harder thing to pin on your LinkedIn headline.
I’ve told myself a lot of comforting things over the past year:
“Once I go part-time, I’ll have balance.”
“Once I resign, I’ll feel free.”
“Once I launch the podcast, I’ll finally feel legitimate.”
“Once it starts working, I’ll stop doubting myself.”
None of those turned out to be true. They weren’t lies, exactly - just delays. Nice little placeholders for the real work, which is this: sitting with success without immediately trying to bury it under the next project.
And don’t get me wrong - I still want more. More control. More money. More space to make things I’m proud of without immediately asking if they’re “valuable.” I don’t think I’ve “made it.” But I do think I’ve crossed some invisible line where I’m no longer waiting for permission to try.
And that, apparently, is where the discomfort starts.
Because when you stop apologising for your ambition, when you stop pretending your wins are accidents, you lose the safety net of likability. You risk being seen clearly. And being seen clearly is its own kind of exposure. Especially if you’re a woman. Especially if you’re used to deflecting praise like it’s an incoming frisbee at a BBQ.
But I’m trying to get better at that part. At letting things be good. At wanting more without twisting myself into a shape that makes it easier for other people to digest. At letting myself be a little bit unbearable, because that’s what self-belief actually looks like sometimes.
So yeah… success is embarrassing. Because it’s loud. It’s visible. It shows your hand. And we’ve been taught that if people know how much you want something, they might decide it’s too much. That you are too much.
But here’s what I’m starting to believe - and I say this gently, not as a motivational quote, but as someone who’s still trying to unlearn her own bullshit in real time: The most radical thing you can do is let your life get big.
Not curated-big. Not “here’s my launch!” big. Not “new chapter, feeling grateful” big.
I mean actually big. Big in its risk. Big in its honesty. Big in the sense that it’s fully yours, and you’re not asking for permission to live it anymore.
It might be awkward and a little too loud for the version of you people are used to. But at some point you have to decide which discomfort you’re willing to live with: the discomfort of being seen, or the discomfort of never showing up as yourself at all.
I’m choosing the first one. Even if it still makes me want to hide under the duvet afterwards.
- S