Why Your Business Will Break You (And That’s a Good Thing)
Entrepreneurship will change you, but not always in the way you expect
When I started my business, I thought growth would come from learning how to market, sell and act vaguely like a CEO.
And it did… but honestly not in the way I imagined.
What I really learned?
How to have hard conversations.
How to sit with rejection and not make it mean something about me.
How to trust myself when the numbers didn’t look how I wanted them to.
How to get comfortable with not being liked by everyone.
How to stop trying to prove myself and instead lead with authenticity and vulnerability.
The blessing and the curse of entrepreneurship is it’s one of the deepest self-development journeys you can go on.
Not because you become your own boss and get to make all the decisions.
But because it makes you reach down into the deepest pits of your soul.
And once you’re down there you’ve got two choices:
Succumb to your deepest insecurities, doubts and fears and ultimately quit
Rise up stronger and become the most badass version of yourself
(There’s sort of a third option too: flounder somewhere in the middle, stuck in your old patterns until the plateau is even more painful than the awakening).
You'll come face-to-face with the sharpest edges of yourself
It's a bit like becoming a parent for the first time. You think the challenge will be the 'keeping a small human alive' part. Sleep deprivation. Logistics. Food.
But in reality it's one hard look in the mirror. You catch yourself reacting in ways you swore you never would. Repeating the same reprimanding phrases your parents said (that you swore you'd never say).
You see your own childhood play out in how you handle your toddler melting down over the wrong colour plate, or your teenager lying point blank to your face.
Business has a way of doing the same thing.
You initially think it's about laying the foundations. Solid offer. A marketing plan. Putting yourself out there. And then you realise it's about all the in-between moments.
The time you launch something and no one responds.
When a client says an excited yes and then ghosts you.
The low income month which has you question your ability to do this.
Receiving an email saying you're 'so inspiring' on the same day you're doubting your whole existence.
And you feel all of it.
The part of you that deep down fears you're not good enough.
The part of you that wants to be liked and tries to control everything (hoping control will keep the fears at bay).
The part that wants to appear successful and like you have your shit together (even on your lowest income month).
The part of you that worries you'll be found out.
I used to think I could outrun those patterns by achieving more.
If I just created more success, hit 10K months, then 30K months, built a team and systems.… then I'd finally feel clear and confident.
But what I've learned, again and again, is that until you meet those deeper patterns head-on, they'll keep running the show.
No matter how many courses, productivity hacks or Stripe notifications you throw at them.
At a certain point, it stops being about how to build your business, and becomes about whether you can hold the thing you're building.
And the worst part?
Each new level in business brings its own set of unique head-fuckery challenges.
As a client once said to me, ‘new level, new devil.’
It's one thing to launch a programme or put your prices up. But can you actually sit with what comes after that?
Can you raise your prices without that horrible spiral of guilt? Without lying awake at 3am convinced no one will ever buy from you again?
Can you say no to the shiny opportunity that strokes your ego, but deep down you know will pull you completely off track?
Can you handle more eyes on you, more money coming in, more people expecting things from you... without spiralling into self-doubt or becoming someone you don’t really like anymore?
Most of the time we don't talk about this stuff.
We stay busy serving clients. Optimising funnels. Downloading someone else's blueprint for the hundredth time.
I'm not saying there's no value in that, but none of it matters if your nervous system is set to ‘panic mode’. If your self-worth is connected to your bank balance. Or if you're terrified to let people see who you actually are.
That's when the sneaky self-sabotage starts.
It'll have you procrastinate with launching.
Or tinker with your offer for the tenth time instead of sending the damn email.
It'll tell you now's not the right time, that you're not quite ready, that someone else is already doing it better.
Sometimes it shows up right before you press publish, and other times, it lingers for weeks in the background, like static in your brain you can't quite switch off.
Business is like a mirror that shows you everything you've been trying not to look at
Whatever's unresolved will find a way in.
That voice that says, "You're not good enough" will rear its head every time things get challenging.
That part of you that wants to be liked whispers to tone down your emails, swear less, or keep things general so they're useful to everyone.
And just as you're about to press publish on your latest email… that thought: "Who do you think you are?"
We've all experienced it, but what I've learned is that it doesn't work to push those parts away.
You can't bypass them with a slicker funnel, a new mentor or the next course (yes, we all try and buy our way out of these uncomfortable thoughts and feelings).
Instead you have to: Meet them. Work with them. Grow through them.
When you can do that, things shift, not just in your business, but in you. You become a kinder, more patient and resilient person. You become the best possible version of yourself. And you'll see this ripple out across your relationships, your parenting and your life.
When you avoid doing the inner work
You could try to avoid looking inwards and just keep going, but I don't recommend it.
From my experience, when you do this, you stall. Your income plateaus. You burn out trying to outwork the fear. You start thinking maybe you're just not cut out for this, and you keep rebuilding from the same broken blueprint.
You hold back your real voice, your actual ideas, the path that's obviously yours... because deep down, it doesn't feel safe to be that visible.
Avoid the inner work and you end up productive but disconnected. Visible but armoured. Appearing successful on the surface, but secretly, stuck.
If that’s you, you’re not broken. Most of us were never taught how to actually feel our feelings, let alone work through them.
We learned to push through. Stay professional. Perform. Definitely don't cry at your laptop.
…But the thoughts come anyway.
So how do you actually do the 'inner work'?
Here's what I've learned (and have to keep reminding myself):
Hold those disruptive thoughts lightly
Just because you're thinking them, doesn't mean they're true. You can notice them without letting them run the show.
Give them a name.
Mine's Ruth. When she starts with her "you're not good enough" bullshit, I say: "Not now, Ruth. It's 7am and I don't need this." Some days she gets more compassion. Other days I tell her (with love) to fuck off.
Don’t run from your feelings.
Just notice them. Notice the tightening in your chest. The lump in your throat. The churn in your stomach. Don’t attach a story to the feeling. When you notice physical sensations, they tend to shift. Breathe through them. Lean into them. Can I go as far to say as love them? It’s just your body processing emotion.
Re-build your relationship with your body
Strength train. Do breathwork. Meditation. Dance to stupidly loud music. Get out of your head and back into your body.
You don't have to think your way through everything.
Then, just keep going.
The goal isn't to become someone who never doubts themselves. It's to stay with yourself when the doubt shows up. To keep showing up even when it's messy.
Want to do this work together? I'm running a retreat this October called The Cocoon for business owners who are ready to outgrow old patterns but aren't sure what comes next. Three days in the mountains, doing the kind of inner work that makes everything else feel clearer. Details at: gemmagilbert.com/cocoon
