The Boss Stories

Three hundred and forty-one. That’s how many resumes hit my inbox when I posted one part-time contractor role — one — with the word “remote” in the title. I did not sleep well that week. Not because the job was hard to define. Because I looked at that number and thought: there is no version … Read more

Here’s a fun fact nobody tells you: you can run a profitable freelance business for three years, file your quarterly taxes like a responsible adult, learn to say no to scope creep — and still be a complete idiot the first time you try to hire someone. I found this out in real time, in … Read more

Tuesday, 9:14 a.m. Client A messages: “Quick favor, need the revised deck by noon, sorry for the short notice!” Client B messages four minutes later: “Circling back — did you get a chance to look at the copy? Kind of on a timeline over here.” Client C hasn’t messaged yet, but Client C’s invoice is … Read more

Three months. That’s how long I knew Priya wasn’t going to work out before I actually sat down and said it out loud. Not to her — to myself, in the shower, at 6am, doing that thing where you rehearse a conversation for the ninetieth time and still don’t have it. Three months of “maybe … Read more

Here’s a fun exercise: add up every hour you’ve spent this year on hiring, onboarding, or firing someone. Now imagine you’d spent that time on billable work instead. I did this math last month and had to close my laptop and go stare at a wall for a bit. It’s a lot. It’s always a … Read more

Nobody hands you a manual when you hire your first person. There’s no orientation packet for “how to tell another human their work isn’t quite landing.” I got promoted from Boss of Myself to Boss of Other People with zero training, same as every solo owner who’s ever brought on a VA or a subcontractor. … Read more