Right then. I’m starting a diary. Yes, an actual diary, well online at least. Like Doogie Howser. If you don’t know who Doogie Howser is, congratulations: you are young and fresh-faced and probably haven’t had to Google “how to write a business plan” at 2am with a half-drunk glass of rosé in your hand.
This is going to be a series: The Diary of a Mildly Chaotic Solopreneur. Because I, dear reader, am one. Slightly chaotic, mostly functioning, semi-confident, and permanently caffeine-dependent. If you imagine solopreneurship as a sleek MacBook aesthetic with plants and perfect lighting, I’m hRight then. I’m starting a diary. Yes, an actual diary, well online at least. Like Doogie Howser. If you don’t know who Doogie Howser is, congratulations: you are young and fresh-faced and probably haven’t had to Google “how to write a business plan” at 2am with a half-drunk glass of rosé in your hand.
This is going to be a series: The Diary of a Mildly Chaotic Solopreneur. Because I, dear reader, am one. Slightly chaotic, mostly functioning, semi-confident, and permanently caffeine-dependent. If you imagine solopreneurship as a sleek MacBook aesthetic with plants and perfect lighting, I’m here to tell you that image can fuck right off. My version is Post-it notesere to tell you that image can fuck right off. My version is Post-it notes on every surface, receipts in every pocket, and mild heartburn from too many flat whites.
Chapter One: From PAYE to “What The Hell Have I Done?”
Once upon a time (about two years ago), I had a proper job. A real one. With a desk and a landline phone, and people who did things like payroll and holiday cover. It had structure. Predictability. Passive-aggressive team meetings. And then one day: redundancy. Cheers for that. Genuinely because it turned out to be the very shove I needed.
But what they don’t tell you about going from PAYE to self-employed is that your job title quickly becomes literally everything. Marketing? You. Finance? You. IT? Still you, sobbing while resetting your WiFi router for the third time that morning. HR? Also you, giving yourself a stern talking to in the mirror now and again.
Setting up your own business is like trying to build a plane while flying it and simultaneously Googling “how do you land a plane”. And sure, everyone claps when you take off. But halfway through the flight, you realise your co-pilot is a mug of coffee and your onboard snacks are six Sainsbury’s jam doughnuts and a packet of Wispa Golds!
Team Meetings for One (and a cat who totally judges me)
Every Monday, I try to have a “team check-in”. It’s just me, my notepad, and an air of desperation. Sometimes I open a Google Doc to take notes for myself about myself! Sometimes I argue with myself about strategy. I once sent myself a follow-up email and thanked myself for my time. The madness is real people
When you’re running a business on your own, you start narrating your tasks just to feel less alone. “Right Kevin, let’s smash out those invoices, lad.” Followed by, “You absolute legend” after remembering your company reg number from memory. Then silence. Because no one claps for you when you do the boring-but-essential stuff. So sometimes I clap for myself. Sue me.
Also, shout out to my cat, who has witnessed every meltdown, brainstorm, victory jig, and midday nap. Shee remains unimpressed, but loyal. Probably just in it for the catnip!
On Friends, Sanity, and Sharing the Load
If you’re reading this and considering going solo: do not do it without your people. You need a crew. Not necessarily business partners, but mates you can message with, “Do I charge VAT on this or just cry?” or “Rate this logo idea: 1 to sack me.”
Running your own show is glorious and horrifying in equal measure. Having people around who’ll tell you when you’re being a genius and when you’re being a tit is vital. Find your people. Hold them tight. Buy them coffee and say thank you. Or wine. Or a massage voucher if you accidentally sent them seventeen voice notes in one afternoon (that’s low for me!).
The Dream vs The Reality
Everyone talks about the dream. Flexibility. Freedom. “Work from anywhere.” Which, yes, includes The Cluster and your best mate’s garden, and the car park of a BP garage because you needed their WiFi.
But here’s the reality:
You will forget to eat lunch.
You will stare at your own face in Zoom and wonder how you aged five years in one week.
You will have a day where you consider applying for a job as a Cineworld popciorn shoveler just for the pension.
And yet… there is nothing like the feeling of making something from nothing. Of sending an invoice and knowing it’s going straight to you. Of creating a life and a business that (even if it’s a bit scruffy round the edges) is yours.
The Bit Where I Pretend to Be Wise
Here’s what I’ve learnt:
You don’t need to have it all figured out.
You do definitely need snacks.
Don’t underestimate how hard it is to do everything yourself. But don’t underestimate what you’re capable of, either.
Success doesn’t always look like six figures. Sometimes it looks like sending one perfect invoice and going for a smug walk afterwards.
This diary is going to be a place to offload, overshare, swear a bit, and document what it’s like to be a one-man-band business. The highs, the lows, the bloody WiFi outages.
If you’ve made it this far, well done. That’s basically a whole podcast episode in 80s diary form.
Stay tuned for Chapter Two: probably titled “Why Did I Think I Could Do This Myself?” or “HMRC Sent Me Another Letter and I Need a Lie Down”.
Until then, clap for yourself. You’re doing alright.
Kev x
Chief Clustodian 47.5 and winging it!
