1. When did you realise you wanted to be a freelancer?

I always wanted to be one, something about working in your underwear, making your own hours and playing bad music as loud as you want just sounds so appealing. It wasn’t until I got my first big editorial client that I told my boss at a restaurant that I was done being a short order cook because it was distracting me from getting the work done that I wanted to.

2. How did you get started and what was the biggest hurdle you overcame?

I got started by accident, getting my name tossed around by various bands until finally I became a go to guy for merchandise design in the emo boom of the mid 2000′s. The biggest hurdle is really a combination of monotony and consistency. I go through cycles of working with bands where I find myself just drawing a blank, especially designing for bands I’m genuinely not into. Eventually I’ll go for a run or take a day off and my juices are charged, but when a client comes to you with not much direction and you aren’t particularly inspired, it can be tough. Other times work might be slow which usually means the next week will be hell.

3. What’s been your most successful way of getting clients?

Just word of mouth I suppose. Another means is to be spread out quite a bit, I’m known for being a merchandise designer, an illustrator, and a photographer. Often times people might be a fan of one thing I do, stumble upon other work I do, and commission me for work for something they originally had no idea I even did.

One of my biggest successes was a website I made called yourscenesucks.com. The site has a bunch of illustrated profiles of scenesters that I make fun of, but the site has led to me doing probably 100 or so commissioned portraits and various other illustration work.

4. How do you get clients to stay with you and use you for more work?

Simple, just provide them with quality work over and over again. Don’t leave them hanging for too long and just develop a relationship with clients that isn’t too chummy but not too professional either.

5. Do you ever have issues with clients paying late? How do you manage that?

Absolutely, especially working in the music industry. There are a few horror stories but luckily it doesn’t happen as much as it used to. I’ve found that with the advent of social media it is now ridiculously easy to call out a client. I had one a year or so ago who was six months delinquent on a payment and wasn’t responding to months of emails from me. Once I mentioned him in a tweet with something along the lines of “hey, care to talk about that invoice?” he paid that afternoon.

6. What does your typical work day look like?

Wake up, eat cheerios, answer emails, walk my dog, work, eat lunch / reddit / hulu, work, run, cook dinner, work, watch awful movies on netflix. In reality as a freelancer there is no set schedule, but you have to keep your schedule fairly open as a client can email you and need something the next day.

7. Any piece of advice/wisdom that you’d like to give the readers at Freelance Unleashed?

Don’t sleep until you are cozy, If a client asks you to do something and you don’t know how to do it then learn how to do it overnight, Be shameless, Don’t pigeonhole yourself, Expand into other avenues, Go for a run, Get eight hours of sleep when you are cozy.

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You can see more of Rob’s work here:  Rob Dobi  |  Rob on Tumblr  |  Fullbleed

Chris Green

Chris Green at This Design Life
Chris Green is a designer and marketer. He runs an agency called Calloway Green and is also the founder of This Design Life.

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