Love Isn’t the Only Thing You Lose Sleep Over (It's Also Money)

I met Barry for a coffee catch-up the other day. I spotted him first, sat by the sidewalk, phone in hands, bike next to him, looking half like a student and half like a hustler. With his thinning hair (he started balding at 19, poor bloke), he looks older than the rest of us, but the spark in his eyes gives him away.

“Hold on a sec, I’ve just got one more Valentine’s order to send off,” he said before I could even say hello. He was typing furiously to a customer, grinning in that tired-but-excited way people do when they’re running on too little sleep and too much adrenaline.

Barry’s in his twenties, and honestly, his life looks far more exciting than mine sometimes. He’s juggling lectures, part-time shifts, and now this little clothing business he’s building from scratch. I’ll admit, there are moments I feel a twinge of envy.

“Well, I'm the CEO and the janitor and the deliveryman,” he sighed when I asked how things were going. It always cracks me up when he says that. Barry’s always been a bit all over the place, yet here he was describing how carefully he folds every shirt. “Customers are buying these as gifts, so I have to treat every box as if I’m wrapping something for my lover.”

He carried on about the Valentine’s sales rush and how the very first T-shirt design was born after his mate had a rough breakup.

To wind him up, I asked what it feels like to be single but selling shirts plastered with love poems. Barry laughed: “Feels good, actually. It’s like I’m playing Cupid. People wait for my products, and they end up becoming part of someone’s love story. But honestly? The best bit is I get paid.”

That’s when it hit me. Watching Barry hustle made me realise that starting a business is a lot like falling in love. You lose sleep, you overthink, you take risks knowing it might not work out the way you hoped. And still, you go all in, because sometimes, like love, you just can’t help yourself.