STARTING A BUSINESS CAN FEEL LIKE GRIEF & THAT'S NOT A BAD THING

When you quit your job to start a business, everyone congratulates you like you just got engaged. “You’re so brave!” “Living the dream!” “Finally doing it!” No one mentions the identity crisis that hits on your first Monday as the founder, when you are still in pyjamas, wondering if invoicing yourself counts as progress, and seriously contemplating a side hustle in indoor plant care!

What I expected was excitement, freedom, fierce boss energy. What I got (initially) was existential dread, and texts with a few maybe-offers. What I did not expect was the quiet grief of letting go of certainty, status, and structure. That grief is real and weirdly underrated because if you lean into it, it becomes the launchpad for something far better than job security. It becomes the beginning of clarity, creativity, and something that is actually yours.

Grief sneaks in through the small moments. You miss the steady paycheck, being known for being good at things, having a team that laughs at your jokes (partly because they feel obligated todo so!).

But what you gain is the kind of growth you cannot fake. You start to learn the difference between being busy and being effective. Of course there are wobbles, the days where you wonder if you should call your old manager and beg for your cubicle back. But those days start to pass faster and they are replaced with something much much better.

The first shock of entrepreneurship is not that things are hard, it is that you have to change. That all the rules you lived by no longer apply. You are no longer following someone else’s strategy, you are creating your own and to do that, you have to unlearn all kinds of things: the need to always have the answer, the idea that working longer equals doing more, the tendency to ask permission before being bold. It is like spring cleaning your mindset, only messier and with fewer matching containers. But once you start clearing that space, something magical happens. Confidence begins to grow, the kind that comes from making tough calls, backing your own ideas, and learning (quickly) that your self-worth is not tied to your old title.

I have to admit, I really enjoyed my old structure, the 9–5 had a steady rhythm, there was paid leave, automatic super contributions. But it also came with ceilings, politics, and a lot of meetings that should have been emails. But now, I get to build my own system and choose what matters, prioritise what actually moves the needle, set targets, move goalposts…literally anything that creates the picture that I want to paint. At first, it was disorienting. But then it turned exhilarating because for the first time in a long time, I was not just going through the motions, I was building momentum.

Yes, there are days where being an employee looked easier, but easy is not always the goal. This is not just about working for yourself, it is about becoming someone who can back themselves, who can sit in uncertainty and still show up, who can make something out of nothing, and then scale it into something that changes lives (starting with your own).

Freedom comes in waves. One day it looks like a coffee at 10am with no one asking where you are, another day it looks like solving a problem you never thought you could, and realising you are the exact person to lead this. This is not the easy path, but it is the right one…if you are ready to bet on yourself and build something with meaning.

If you are feeling a little untethered, a little overwhelmed, and weirdly emotional in aisle six of Officeworks, that might just mean you are doing it right. Stepping away from your old life is not a sign you have lost your mind, it is a sign you have started listening to it. 

So let it feel like both: grief and excitement. Terror and joy. Structure lost and freedom gained.

Because the grief is not the end of anything, it is the beginning of everything that matters.