Notes On Being an Entrepreneur: January Pressure
On self-doubt, embracing the chaos and learning to back yourself
Notes On Being an Entrepreneur: January Pressure
On self-doubt, embracing the chaos and learning to back yourself.
January is a weird one. And on top of that, being an entrepreneur in January is even weirder.
As someone who doesn’t have a perfect plan, and never really has, I feel the pressure more than any other month to suddenly have one. I think I’ve said “I need to get my life together” most days. Sometimes jokingly, sometimes not.
And don’t get me wrong, January does have its benefits. I really am learning to enjoy it and to embrace it. It allows you to pause. It forces you to look at things properly. To re-align, to prioritise, and to ask what you actually want to keep and what you’re ready to let go of.
But with that comes a lot of noise.
January has a way of amplifying certainty. Suddenly it feels like everyone around you is fully optimised and ready to go. New routines. New goals. New plans spoken out loud before they’ve even settled. You notice it everywhere. In conversations. Online. In the questions people ask.
And you’re still figuring out what you’re even doing, let alone where it’s going.
Yesterday I had one of those days where everything clicked. One of those days where you think, yes, I’m onto something. This makes total sense. I feel ready for it.
And then today I’m like… who do I actually think I am.
Welcome to the life of an entrepreneur.
That contrast is usually where the self doubt comes uninvited.
The reality is that I have no one telling me what to do. And yes, that’s a great thing in so many ways. It’s the freedom I wanted. But I’d be lying if I said it wasn’t also a struggle at times.
As an entrepreneur, you need the discipline of a manager, the patience of a long term thinker, and the self trust of someone willing to move without constant reassurance.
Some days that feels empowering. Other days it just feels heavy.
January makes that weight more noticeable. There is no straight path to this life. That’s part of the appeal and why I chose it in the first place. It’s fluid. It changes. You’re allowed to evolve without permission.
But it also means there’s no structure resetting itself for you. No objectives handed down. No clear KPIs. No sense of being folded back into something that’s already moving. It is all on you.
The art of backing yourself.
Sometimes I do wish someone else could back me other than myself. Someone to sit next to the idea, or quite literally inside my brain, and say, yes, this makes total sense. Keep going.
The reality is, wanting that doesn’t mean I don’t believe in what I’m doing. I think it just means I’m human. Most paths come with built in reassurance. This one doesn’t.
Self promoting myself, or giving myself a pay rise, doesn’t quite land the same as someone else doing it for you. It’s like clapping for yourself. Necessary, but it never quite hits the same.
So you learn to move without it. At first that feels unsettling. Then, slowly, it becomes a quieter kind of self trust.
And yes, people do love to romanticise entrepreneurship. But just like anything in life, it’s mostly made up of quiet days. Small decisions. A lot of sitting with uncertainty and not really knowing if you’re doing it “right”.
This is also fun. And it is a privilege. I’m aware that getting to sit with these questions at all is not something everyone gets. Knowing that doesn’t make it easier, but it does stop me taking it for granted.
Some days I wish someone else could carry the responsibility with me. Other days I recognise how rare it is to have this much ownership over my own life. Both can be true.
So yes, January is strange. The doubt is there. The pressure to have it all figured out feels louder than ever. But even when it feels pretty uncomfortable at times, there’s something very alive about it.
