Thoughts on self-employment, six months in

It’s six months this week since I resigned from my day job. Here’s what I’ve learned…

(First, some caveats. We’re very lucky. Very lucky. Things have worked out for us because we do something very specific that hardly anyone does well, in a very small city, with an even smaller web community filled with people we already knew either professionally or socially. Those people have taken chances on us that have given us the experience we needed to get clients on our own. Those people are amazing and we owe them a hell of a lot.)

If you think it’s possible to quit your job, quit your job.

Six months ago, I was terrified. I remember a late-night conversation in my kitchen — me asking my boyfriend for the eight thousandth time if he thought I was doing the right thing. Him reassuring me that it would work out, that money was just money, that he had a steady job if we didn’t get any work. The idea of not having a regular paycheque seemed so utterly terrifying, like I wouldn’t have any control at all.

Oddly, now I feel like I have more control than I ever have. I can’t guarantee we’ll have any money six months from now, but it’s within my power to go and get work, to turn down work, to decide when and how we’ll work.

When people hire us, they’re paying us enough that they have to take us seriously. They can’t squander our time or our work like employers can (and frequently do). I have the freedom to ask for what I need to get things done, and to go away and do it well, without interruptions. I can’t tell you what a difference those things make to my morale, my productivity and the quality of my work.

Until I didn’t have to do it anymore, I didn’t realise how much energy I’d been losing just by spending eight hours a day in a noisy, open-plan office filled with constant distractions, emails and meetings. Turns out I do my best thinking outside, usually while walking. If I lose focus, changing location can help me get it back — sometimes I migrate two or three times across the city in the course of the day. I’d spent twelve years battling my concentration span, only to find that, mostly, it’s just that nothing about a 9-5 office job matches the way my brain works.

(Central heating is amazing, though. God I miss central heating.)

Now, on days when I’m unproductive, I don’t waste anyone’s time or money but my own — I can give up, go and annoy my cat, and try again later. When I’ve got nothing to do, I might not get paid, but at least I’m free to spend my time on whatever I want.

The deal I made with myself when we started Sixtyproof was that I’d save enough money for six months’ rent and expenses before I quit, so I didn’t have to go to sleep every night worrying about paying the next bill. The first year we existed, I managed to save less than a quarter of that, and worked just about every weekend. If a client hadn’t cold-called to offer us tens of thousands of dollars of work we needed to be available Monday to Friday to take, I’d still be sitting at my desk in an agency, writing app micro-copy and trying not to die from boredom.

It’s good to have a plan. You need to have a plan. But at some point you have to take the risk — and that point is always going to come before you’re ready for it. Be sensible, but not too sensible.

Get good at talking…

I’m an introvert. I’m also a writer, not a talker, and a lover, not a fighter. The business world is not designed for people like me.

As an employee, I was endlessly frustrated by the fact that the people who made the most noise got the promotions, were credited with the ideas, and had their opinions considered. There is no correlation between talking the most and having the best ideas… but the entire system of corporate business is set up as if there is.

As a consequence, if you want to convince people you know what you’re talking about, you have to sound like you do. (This doesn’t mean you shouldn’t say “I don’t know” when you don’t know — but say it with confidence, and offer to go and find out.)

The biggest thing I’ve learned in the last six months is to start talking. I used to wait until I had my entire thought mapped out before I started speaking — so, often, someone else got to my point first, or the moment passed before I could formulate my argument. I got nervous worrying that I’d forget my thought or my point would turn out to be irrelevant once I said it — and sometimes it was. But so much of everything is conversation and relationships that even if I put forward an idea that turns out to be a dud, it’s usually worth exploring to find out for sure.

I’m not saying I’ve become a noisy blowhard (or at least I hope not) — I think I’m still a good listener and a careful thinker. I just had to start trusting myself and taking risks, because confidence is so key to building trust with clients. They’re trusting you with their money and their intellectual property — you have to be able to show them that you deserve that trust.

…But don’t play the game.

Your work should speak for itself — you just have to be able to talk about it intelligently and on demand. You don’t have to become a jargon-slinging, bourbon-swigging ad-man. Our industry is filled with guys in tight shirts and hundred-dollar haircuts talking slick, stylish nothing over the top of one other. We don’t think we need to be like them to play in their sandpit. We’re (trying to be) unapologetic about being women, about Sara being a mother, about not having a fancy office and a retinue and polished pitch-patter that’s 90% name-dropping and buzzwords.

We’re also actively trying not to hire. It seems like that’s the thing everyone does — like growth is success in and of itself. We started Sixtyproof to do what we love to do, well, all the time. But we also started Sixtyproof because we hated working in offices and being tied to our desks for eight hours a day, and we have (or want to have) families.

We don’t need an office, so we don’t have one. We have almost no overheads — no one else’s wages to pay, no rent to keep up with, no equipment to buy. That means that if we want to work 15 hours a week, we can. Sara can take the morning off and play with her daughter. I can take a day to work on my novel (which is what I’m meant to be doing right now). On the flip-side of that, if a client needs us to work through the weekend to meet a deadline, we can and happily will.

Hiring six people might make us more “successful”, but it would also mean we’d have to go back to working in an office. We’d have to show up and leave on time, and we’d have to manage our staff’s work rather than doing the work ourselves. We’d definitely never get to go on holiday again (as opposed to now, when we’re hopeful that’s only a “probably”).

The week before I quit my job, I told one of the senior guys at work that I was thinking about taking the leap to self-employment. He asked me to think forward five years — did I want to be “some mom and pop two-man shop”, or be a top man in an agency like the one I worked for, making loads of money for prestigious clients and managing a bunch of juniors? It was obvious which one he thought sounded more impressive — and as soon as he said it, I knew exactly what I wanted.

Our goals have never been money or the trappings of success. Success, for me, is doing really good, involving work — on my own terms, in my own way, with time to write my own stuff and go on adventures with my boyfriend and read too many books about climate change.

Right now, we’re managing that. And that’s pretty cool.

I’m not sure why I felt the need to write any of this down, other than that maybe I wish someone had written it down for me so I could have felt slightly less scared and alone in my kitchen that night. But if anyone out there is thinking about going out on their own… be brave. Back yourself. And feel free to get in touch.

By Katie Freire

Writer of things. Annoyer of cats. Mother of very small dragons.

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