It all happened very gradually. In the first year I only had one paying freelance job, and went out and bought a new surfboard with the money. The next year I did two or three jobs which paid a little bit more, so I went out and bought a bike and another surfboard. After five or six years it built to a point where I was freelancing, literally, from 6 pm until 2 am in the morning, five or six days a week.I know everybody brags about how hard they work, but I was truly working myself to the bone.

One Friday afternoon, around the time when the economy went south, I got laid off from my day job. I went over to my wife’s place of business and said “I just lost my job.” She was panicking and said “what are you going to do?” I said “I don’t know, but I do have some freelance I can go home and work on.” So, I went home, got to work, and that was the beginning of full-time self employment. I don’t know if I could put my finger on a specific moment when or how my practice took off. That first year was just one weird time.

I was working that 9 to 5, and then coming home and freelancing but jobs started coming out of the woodwork. Self-employment wasn’t a conscious decision or a big life goal. Had I not gotten laid offI might still be working a 9 to 5 job. I’ve always worked hard because I’m in love with what I’m doing, so as a result my business grew and grew. The stars have consistently just kind of aligned. 

I work by myself and I have an accountant. He’s as close as I’ve got to an employee, though he’s not at all my employee. My clients are pretty diverse and all over the map, which is something I love. About 30% are local, 30% regional, and about 30 or 40% national or international. Any given month those numbers might skew one way or the other, but that’s the gist.

I have no plans to expand or hire any employees. I get asked about this all the time, but I’ve seen enough designers-turned-studio-heads who aren’t doing much creative work themselves anymore because they’re too busy taking meetings, corralling their employees, and returning phone calls. I’m stressed enough by my relatively simple situation. I don’t need any more stress. I’m keeping my goals lower and more manageable. I’m really happy with my work, my family, and my life. As far as I’m concerned, I’ve got the best job in the world. Most days.  

I do occasionally need to partner with developers, photographers, copywriters, and so on, but frankly I try and link those people with the client directly if possible. I’ll stay on board and coordinate / mediate if need be, but it makes more sense from a time management standpoint for me to connect my client directly with those people and let those other creative people steer their own ships however they’d like to.

This might make me sound technologically inept, but almost every time I’ve tried to implement any sort of fancy project management program to make my life easier, there’s so many more bells and whistles than I need. They’ve all felt too complicated so I would abandon it and just go back to my rudimentary desktop folders full of text documents – project notes, deadlines, invoices, and so on … a green-highlighted invoice file means it’s been paid and a red one hasn’t. Simpler is better for me.  

“I went over to my wife’s place of business and said “I just lost my job.” She was panicking and said “what are you going to do?” I said “I don’t know, but I do have some freelance I can go home and work on.” So, I went home, got to work, and that was the beginning of full-time self employment.”

Over time I’ve carved out my own simplistic way of doing things and have never encountered a problem because of it.

You know, I can’t really explain why new clients keep coming my way, other than knowing my work is out there and people see it and they like it. That probably sounds overly obvious, but it’s essentially my entire marketing strategy. Sometimes I think larger clients are simply looking for a designer who does consistently good work, and quickly. So, if I can be that vendor in their database, some of those agencies will come back once a month and ask if I’m available say Tuesday through next Thursday. They’ll overnight me an advance payment and we’re off and running without any fuss. So as long as I don’t drop the ball, those clients are easier to keep happy.

I constantly panic over losing all my clients and work completely drying up. What if everything suddenly evaporates overnight? It’s something I’ve been thinking a lot about lately. I guess anybody in my situation is kept up at night wondering about the same thing. At a lot of 9 to 5 jobs you get to take some things for granted – there are other people whose job it is to look out for you. Getting laid off, for me, came out of the blue. Luckily I’d already built a whole separate nighttime design life that I rolled right into, but still, it was fairly shocking. But now, with such a hyper-awareness of what I’m working on, what’s on deck, what’s in the bank, and so on, I think my potential demise would set in gradually. That’s what I tell myself, anyway. That it won’t be like getting let go from a 9-to-5. I’ll see it coming from further off and have time to prepare.  

Everything right now is wonderful, I have way more work coming my way than I can handle, I’m doing great financially, everything is awesome. Despite my fears, it’s not just going to suddenly end tomorrow. I’ve spent the last couple years getting that possibility squared away. If something catastrophic happened and I was out of commission for a little while, my family would still be fine. 

It’s tough being a one-man show and trying to figure out how to keep everybody happy. Clients with smaller projects and lower budgets can often be needier than those with huge projects paying five times as much. But it comes with the territory and I’ll often find myself taking three steps backwards with somebody so I can set myself up to take four steps forward with somebody else.

“Everything right now is wonderful, I have way more work coming my way than I can handle, I’m doing great financially, everything is awesome. Despite my fears, it’s not just going to suddenly end tomorrow.”

Thankfully it’s been rare that I’ve lost a client. Usually the projects that don’t go well are projects that I can’t imagine going well for any designer.

A big hurdle for me was realizing there’s a point in the process where you have to flip the perfectionist switch off and just get it done. I used to pull my hair out and have a lot of back and forth with clients, trying to get everyone on the same page. Going to battle over every single aspect of the work that I thought was worth fighting for. I wouldn’t call it “being difficult.” It was just what I thought was my ethical duty as a professional designer. What I learned after a while is that sometimes clients are who they are and you’re not going to change them. If they demand that they get what they want regardless of whether or not it’s what they actually need, you might as well just give them what they want. Save yourself the headache. I articulate my decisions and defend my work once, and if it falls on deaf ears I’ve learned it will unfortunately continue to fall on deaf ears.

As for actually breaking up with them or firing them, I’m admittedly not great at that. I’m not good at flat out saying this isn’t working out, it was nice knowing you. I don’t think I’ve ever done that. I’ll just keep grinding myself into the dirt, trying to make people happy, until I’m making about $2 an hour.