What I Learned About Being a Boss Before I Ever Was One
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I started my business at 18, which means my entire frame of reference for what being a boss looked like came from retail and waiting tables, and while that sounds like it should be a disclaimer, it really isn’t, because as it turns out I got incredibly lucky in those early jobs and didn’t know it at the time.
My first retail manager Helen ran a tight ship (low wages, pretty hard work, high standards) but she also once handed a mop and bucket to a customer whose kid had peed in the fitting room, and I remember standing there thinking: she’s on our side. She has our back. We are a team and she is our captain and she will go to bat for us, even when going to bat means handing a grown adult a mop and a pointed look. (Obviously, I was also thinking…WTF?!).
Looking back at 40, I’m actually kind of floored by how good those early experiences were. I was a solidly working class kid who wanted money in my pocket and the independence that came with it, and those jobs delivered that and a lot more besides. Waiting tables continued the theme: another boss who somehow turned a rotating cast of teenage characters (and BOY were there some characters…) into a genuinely functional, hardworking team where everyone pulled their weight and looked out for each other. (Waiting, it most certainly was not.) Sure, some of it was gross, and yes I would mostly rather have been out with my friends, but I was learning what good leadership actually looked like without realising I was in class.
So when I started my own business, I didn’t walk in cynical or suspicious of what being an employer meant. I walked in with a surprisingly solid template for what good looked like, and absolutely no idea how hard it was going to be to actually deliver it.
The moment it got real
A few years into running the business, the owner of the operation next door asked me why I was there so much. I had employees, why was I here every day? Didn’t I…play golf or something?
My internal answer, if I’m being straight about it, was: because it’s my goddamn business, and I am trying to grow it into something, and I have absolutely no interest in just toddling along with something that works okay when there is so much more potential on the table. I wanted to set an example, I wanted to keep my foot on the accelerator, and I fundamentally believed — and still do — that you have to evolve or die, and dying was not on my roadmap (not that I really had too much of a roadmap back then, other than “make business good”).
His outlook on owning a business boiled down to: hire people, they work, you don’t. Which even then just felt so small and short-sighted to me. Absolutely at odds with every instinct I had about what building a business meant. What I didn’t fully reckon with in that moment was how much my model was going to cost me, and I don’t just mean financially.
What nobody warns you about
You expect the money stuff to be hard, and it is. You expect the long hours, and you get them. What you don’t expect, and what nobody really prepares you for, is the weight.
From the very beginning I was employing people across a whole range of ages, including people who were twenty years older than me, and I had no management training, no business degree, and nobody who’d done this before that I could call and ask for help. I was learning everything from Google and business books and trial and error (let’s be fair…a lot of error sometimes), which is fine and survivable but is also goddamn exhausting in ways that are hard to describe until you’ve lived it.
I couldn’t take a trip without my laptop for the first ten years. Delegating something as fundamental as payroll felt for a long time like it might actually kill me. There was also something else, something harder to name…a kind of embarrassment? Or maybe more accurately a dissonance, because people have very specific expectations about what a business owner should look like and how they should carry themselves and what their life should resemble, and for a long time I felt like I was performing a role I hadn’t quite grown into yet.
And then there’s the people management piece, which for someone like me is its own particular flavor of challenge, because I am at my core a people pleaser with what I can only describe as a pathological need to be liked, and becoming a people manager when that’s your factory setting is not something you just fix or logic your way out of. It’s something you work on, slowly and imperfectly, year after year. (I know, I know. That’s what therapy is for. Way ahead of you.)
The weight of other people’s lives
The thing nobody told me at 18, and the thing I find myself thinking about most when I reflect on those years of running a business, is the sheer weight of responsibility you carry for the people who work for you. These are real people with real lives and real bills and real families, and their stability is tied in a very direct way to the decisions you make, and I think the employers who forget that — who stop feeling the weight of it — are the ones who end up making the worst calls, not just ethically but strategically.
The weight is a feature, not a bug. It can crush you if you’re not careful about it, or it can press and press and press until it creates a diamond.
On employing your friends
I’m not going to tell you categorically not to employ your friends, because I don’t think it’s that simple and I’ve seen it work, but I will say this: don’t employ the friends you know, somewhere in the back of your mind, are going to be bad employees, because you do know, and you are not doing them or yourself any favors by ignoring what you know.
People warn you about mixing friendship and work for a reason, and the reason isn’t just abstract. It’s because the dynamic shifts in ways that are genuinely hard to predict until you’re in them. The question isn’t really whether friendship and a working relationship can coexist, because sometimes they absolutely can. The question is whether you actually know that person’s work ethic, their attitude towards responsibility, and critically, their attitude towards you, not the version of you they grab dinner with, but the version of you who signs their paycheck and has to have the conversations that nobody enjoys having.
It can work out beautifully. It can also be kind of gut-wrenching to discover that the person you hired out of loyalty and genuine affection doesn’t extend the same respect back in the other direction, and that particular realization hits in a way that a difficult hire through normal channels just doesn’t.
What the gap actually looks like
Being employed and being the employer aren’t two points on the same line. They are fundamentally different jobs with different skill sets and different pressures and entirely different definitions of what a good day looks like, and I think one of the most useful things I can tell you is that treating them as a simple progression, a natural next step, sets you up to be surprised by things you didn’t need to be surprised by.
When you’re employed, someone else is carrying the weight. When you’re the employer, you chose to pick it up, and nobody made you do that. On the hard days that distinction actually matters quite a lot.
What I keep coming back to, though, is those early jobs. Helen with her mop and her pointed look. A boss who somehow turned a bunch of teenagers into a team that actually worked. I didn’t know I was in class at the time, but turns out I was taking notes, and I turned those into some of the most valuable lessons of my career.
Chloë Scout previously built and exited an ecommerce business that grew to nearly $10M in annual revenue with over 100 employees. She writes about the practical, unglamorous, nuts-and-bolts side of building and running a business, without the MBA.