Artist Spotlight

Freelancing: 3 Months In with Greg Stewart

In this first part of an ongoing series with Greg Stewart, he walks us through his recent move from being a department-of-one at a local agency to the studio-of-one life of a freelancer.

Portfolio | Reel | LinkedIn

Reading Time | 17 minutes

Greg Stewart’s Reel 2018

You’ve been freelance for how long now?

Full time for just over 3 months. Actually yesterday was my 3 month birthday.

How has the 3 months been so far?

It’s been up and down. I had been moonlighting freelance for 3-ish years, so I kind of knew enough about it to know I wanted to do it. Everyone told me it’s always up and down, feast or famine. Really, April and May were super busy, and June, I just did my first paid project this week. For three weeks, it was like I’m having to force myself to work on stuff just to keep myself busy. But I had sort of been planning on freelancing for a while, so I tried to save up quite a bit so it wasn’t like, “oh, I’m not going to be able to eat”.

I honestly kind of enjoy the up and down. It’s sort of nice being really busy with a ton of stuff to do, and then having a little down time to sort of recover. Now I have some time to watch some tutorials or network with some more people. In the seasons where it’s really busy, you don’t have time to network or grow business as much because you have to get stuff done. It’s just kind of a cycle, but so far I’ve really enjoyed it. I had been wrestling with do I or don’t I for a really long time so I think there is a huge sense of relief to have finally made a decision. And, honestly, it was super encouraging how, both here and the larger animation community, were like, “dude your reel is so good I’m excited for you”. I figure at some point all the euphoria wears off.

Are you still riding on some of that euphoria?

I think so, yeah. It’s been fun just being able to try different things. There’s some projects where I’ve been involved more as a project manager—I don’t even have to touch After Effects for this project. I can just help find freelance talent and work with the client or the studio owner to make sure everything is going well. It’s a little bit of time off from being stuck at a computer all the time. Other projects, I’m just handed a bunch of boards and I get to put on my headphones and sit in After Effects for a couple days and just crank on stuff. I think I really liked having the variety: being able to go back and forth.

Was that the most appealing thing for you to go freelance: the variety?

I think it was a number of things. I mean, I have nothing to complain about really from my last job. I felt like I had kind of hit a ceiling in terms of what I could learn when it came to my technical abilities as a motion designer. If I had a question about, “how would you approach animating this?” or “I saw this thing and I’ve never seen it done before how would you?” I couldn’t do that regularly apart from hanging out with people. Hopefully it’s not prideful to say that I was the best person, I was just the only person.

The best person by default.

And also the worst, right? I think there’s a growth appeal of throwing myself in the deep end and just forcing myself to learn to swim in some ways that I’d never have to learn working full time with a bunch of other people. There was the flexibility that was really appealing. It just sort of felt weird at the agency I was at; busy times were really busy and then not busy times were really not busy. We would always joke about me having postpartum depression. I would just be insane on something for a month, then having nothing to do, but still having to find stuff to do and show up to work. I think I just wanted to have the freedom to take a day or two off after finishing up a project, or call it a day and go home if I’d had an especially productive morning. I thrive in having a certain amount of control over my schedule and the projects I’m working on. The nature of working for someone else meant that I didn’t have that. I like traveling and being able to explore new things; you only have so much PTO in a year. I mean, the last few months I drove to Kentucky and back for a work thing. I got to fly to North Carolina and drive back. Fly to like California and back, so I’ve driven to 18 states. It’s been super fun just being able to work really hard for a week then I don’t have to work for a week. I get to road trip with some of friends, or I can go visit family in Vancouver and work from Vancouver and nobody that I’m working for cares where I’m working. I probably abuse that freedom a little bit, but I kind of had to once I started.

Well if you’re going to go freelance, go freelance.

I know. It’s like “be all in”.

Are you building routines or systems for yourself?

I think that’s been one of the hardest things; no two weeks are the same. You’re never working on the same projects, typically, or the same thing for the same project. Sometimes you’re really busy, sometimes you’re not. I’ve been reading this book called Deep Work. It talked a lot about the value of routine and how people who had invented things or made significant contributions have always had routines. Like, Albert Einstein wasn’t sleeping in until noon. I’ve really had to force myself to have routines. In the times where I don’t have a week already spoken for I’ve had to really force myself to schedule at least a 35 hour work week and give myself stuff to do. It’s been an important thing, but that’s been one of the challenging things, you know? I’m not going to just go hit the beach or something when I don’t have something to do. If I was employed by someone else, I wouldn’t want to see them being lazy all week. I have to try and treat this like it is a full time job and not just peacing out whenever I don’t feel like working.

“Riverbridge: Invest With Endurance” – produced at Open Book Communications

I think a lot of people are afraid to make that jump to freelance because they’re worried about getting clients. It sounds like you’ve had some pretty good clients from quite a wide array of locations; can you talk about that a little bit?

I think I found my first freelance job on Craigslist with a studio owner here in Minneapolis. He was just looking for some video editing help and I was like, “$25 an hour? That sounds awesome!” But he was actually one of the first people who was like, “you actually have some decent motion chops. You should maybe focus on that a little bit.” I just started googling stuff and trying to find people looking for things. That lead to a couple of things here in Minneapolis. There’s a fine line between I want something that’s going to challenge me to push myself a little bit but also is within my comfort zone enough that I know I can really deliver a good thing. I’ve just seen over and over again that your skill set, your abilities, are important but your character and your ability to deliver on time and communicate is equally if not more important.

That’s like soft skills vs hard skills.

I, as someone who has hired freelancers, would rather work with someone who is like B-grade but is really good at communicating, that’s always going to deliver when they say they are than someone who is awesome but really flaky.

I think sometimes that means it’s a good decision if it feels a little scary but you’re not being a total idiot.

Freelancing has been something you’ve been cultivating for a long time so that when you did finally take a dive, you had an idea of how deep the water was.

It still felt like a jump. I had never been self employed. I tried to do a ton to prepare for it, but it was still really hard to walk into my boss’s office and say I want to go out on my own. I, about as well as I could have, really prepared and it was still really hard: exciting but hard. I think sometimes that means it’s a good decision if it feels a little scary but you’re not being a total idiot.

Now let’s go into why you choose certain clients, or do you let client choose you at this early stage of your freelance career?

I sort of developed three laws of how I decide to work on things. First and foremost, do I feel morally OK working with this client? Clients deserve, they’re paying big bucks, to have someone who’s invested in the project: like personally invested in it. It’s not me saying I hate you. It’s just you really should hire someone who’s really going to work with you on this. So that’s the first thing. Then kind of like, does it pay well? Or if it doesn’t pay well, is this going to challenge me to grow in a way that I want to grow? I took Sander Van Dijk’s “The Ultimate Freelance Guide” course and he talked about how important it is to have values and parameters that you filter your projects with. I want to have it be simple and not like some crazy list of ten or twelve things. It’s just hard to say no to things. That’s another thing I’ve been learning. Time is the one resource that you can’t ever get back so do I want to spend my time working on something I really don’t want to work on if I have the option?

Have you had to say no a lot yet?

I’ve had to say, “not yet”. I’ve had to say, “I’m not available to start until this date”. I’ve been trying to not overwork myself too much, but it is hard to say no. Especially in the insecurity of being freelance. This month being really busy doesn’t mean next month is going to be busy. So if I say no to this now, what happens if I don’t have a ton of work next month and I needed that money? But I think, at the end of the day, you only  know what you know and you have to go based off what you know. If I say yes to this, then I won’t be able to do a good job, then I don’t want to say yes to it because that’s going to taint my reputation. Your reputation is everything in a service based industry.

Why not have a goal that’s lofty?

You’re not worried about trying to find something specific to do right now. It’s more just getting your feelers out there and getting a bit of everything. A year from now or five years from now, do you see yourself being more specific?

I have a decent understanding of my skill set and I want  to leave some room for discovery. I got started in film and I sort of discovered accidentally that I love making stuff in After Effects. Maybe that will happen again, so I want to leave some room for that but I think my goal is I’m going to work on stuff that I’m really proud of as an animator. I have a goal of hitting $100k in revenue my first year which, I feel like it’s not crazy, but it’s ambitious. Why not have a goal that’s lofty? The worst that will happen is I’ll probably make more than I would have if I didn’t have a goal.

One goal I have in the first year is to have someone I can bring in regularly both as a kind of an intern, someone I can teach, but also someone that can carry weight and do work. I love teaching. I’ve learned so much from people who have given away project files online or have answered questions that I’ve had and been willing to be a resource. It’s important for me to do that for other people.

“History is Happening in New York” – produced at Open Book Communications

It sounds like being a freelancer is allowing you to really explore who you are, not just as a professional, but as a person. You’re trying to define who you are but you are leaving yourself open to grow and change. It’s harder, and it totally makes sense why it would be harder, in a studio or agency setting. They hire you for a reason and if suddenly you’re like, actually I prefer to do something else, they’re like well now we have to find someone to replace you.

Where I was coming from, they were really generous when I was like, “I want to try designing” they were like OK. They flew me out to New York City. I got to be a consultant and I was like, “oh this pressure is killing me”. I think it was through them giving me a lot of opportunities to try so many different things that I realized I wanted to really focus on motion design; so I’m really grateful they gave me that freedom to explore. I don’t find it as stressful because now this is all riding on me. If I screw this up, I’m not screwing a bunch of people on my team up. I think I’ve felt more freedom to experiment and branch out a little bit being on my own maybe that’s just a personality thing.

Do you ever envision yourself getting a full time job again at a studio or at a company and then, knowing who you are, would you feel comfortable stating, “this is what I need out of this job”?

I think so. I think I’ve learned a lot about advocating for myself. If I want to be happy and healthy as a freelancer I have to be able to do that. Or at least communicate about what I need then reach a compromise. Right now, I just love the freedom, the free part of freelance: that will wear off at some point, I’m sure.

If I want to be happy and healthy as a freelancer I have to be able to [advocate for myself].

If you were to try your best to summarize in 5 to 10 steps that you took to start your freelance career, what would they be?

I think the first step was identifying that I wanted to do it.Or, at least that I wanted that option at some point and wanted to explore that possibility. Having goals and like having that self-awareness sort of saying this is something I want to do.

I think step two is identifying what stands in between me and making the jump. Two-A would be artistically or creatively. Two-B would be the business stuff. Have a creative and business financial plan and execute on it.

Step three—you’re never going to have all the ducks in a row. It’s just never going to happen so don’t try to do it because you’ll wait too long, you’ll second guess yourself, and it’ll just suck.

There’s always reasons to not do it.

Yeah there’s always going to be something—another month of expenses you want to save up, or another computer you want to get—that’s always going to happen.

I think one of the most important steps too would just be relationship building. I kind of had this pet idea of build up maybe two or three really solid relationships with people who need my skill set. Like, I got to know a couple people who are in film. I know they’re going to want lower thirds, they’re going to want logo animations, so if I needed some pretty consistent income they’re already going to have a huge inflow of clients and if I can kind get myself to be their go-to guy when it comes to graphics. Diversification is a great investment strategy, I think it’s also a great business strategy…I don’t remember what step we’re on. Step four, build good relationships with people who can get you work.

Step five would be make a bit of name for yourself. Anytime I finished something I knew was good, I would share it around. It’s not like I’m coming out of nowhere. I’ve gotten so much freelance work from the people in the School of Motion Alumni Facebook group because it’s like, “oh yeah I’ve been seeing you post in here for a while”. I had three or four people ask for my day rate when I said I’m going freelance. I think trying to establish some kind of presence in the world before you make that jump.

One step I wish I would have taken is have a portfolio. I didn’t build my site until two months after I was freelance. Partly, I didn’t have time but that’s definitely something I would have done sooner because it’s been way easier to get more work or network.

That kind of goes back to not having all your ducks in a row, right?

Yeah that’s maybe one duck I wish I would have lined up a little bit.

I think that surround yourself with people who can help you get better and people who can speak into your life and help you identify your strengths and weaknesses. Community is just like super important. Both people that are above you and can help get better, help you get work, and people who are kind of on your level, who can encourage you. I remember going into June, like I don’t have any work. I was talking to my friend and he was like, “yeah I had two months where I didn’t have any work”. It’s reaffirming to know this isn’t abnormal. It’s good to have people you can teach too, I learned so much from mentoring too, you know?

It kind of reinfuses the initial feeling of or the exhilarating feeling of just watching someone learn something.

I think maybe the last step is the impostor syndrome never goes away like every, every day I will never not feel some amount of, “what am I doing?” Even when I go to Nice Moves things, I’m like, “how am I a mentor here?” All these people have degrees in this stuff. They know about stuff I don’t even know how to spell. It just never goes away, even people who are miles ahead of me I’m sure deal with it. One, that’s OK, and two, I think that helps you get better because it can really push you to work harder and up your game, or you can shrink back and be like, “I’m not good enough why bother”.

Greg Stewarts’ Six Steps to Kicking Off Your Freelance Career

  1. Identify that you want to do it
  2. Identify what is stopping you, both creatively and business-wise
  3. Forget about getting all your ducks in a row
  4. Build good relationships with people who can get you work
  5. Make a name for yourself
  6. Understand that impostor syndrome can hurt you or motivate you

It seems like it’s pretty important to be self-aware about your ego because, as artists, we get a little bit of a following and we tend to think that we’re going make money because we’re so awesome. It sounds like you’re very pragmatic and you’re very realistic about the expectations of the freelance world.

I think that’s so true. I know so many artists, like myself the foremost, that’s simultaneously kind of an asshole, like overconfident in some ways and under confident in others.There’s times when I find myself talking about my work like, you just hear yourself talking and like, “my goodness, I just need to shut up.” Then there’s the other end of the spectrum like, “my goodness look at what they’re doing I’m never going to be that good.”

A lot of time, the idea is that you’re going to get work because you make good work. But the reality is that sometimes work is actually a lot less about the work than it is about all the other stuff. Is there anything surprising related to that that you discovered in the past few months, or has your three year moonlighting been able to set you up?

I think yes, in the sense that there are a lot things that set me up for success. Understanding these are the kinds of jobs I’m going to be good at and these are the sorts of things that are going to be profitable. But I think it’s very different doing it part time nights and weekends than it is doing it full time. I think something that’s been hard is, I don’t think I’ve done, no offense to any of the projects I’ve worked on, but I don’t know there’s anything I’ve done yet that I’m like, “yeah I really want to show this”, which stinks. Where I was at before was like, everything we did, I was super proud of. So now I feel like I kind of set up this expectation that I was going to do really good stuff and most of the stuff I’ve done has been for the meal not for the reel.

But you can be proud of these projects for other reasons. It’s not just the visuals of it; you can be proud of it because you led a team or because you got to try something new.

When the places you’re going to for inspiration are Motionographer and Wine After Coffee, you just see the top 1% of the work that’s out there. You just think that there’s this world that doesn’t actually exist. No agency is doing that 100% of the time and there’s all sorts of work that’s actually probably more of their income that you don’t see. I think experiencing that has been a little bit of a reality check. There was a guy in the School of Motion Group that made an anti-reel which was a minute compilation of all this stuff that he made that just sucked or all the weird render issues he had and couldn’t figure out and just had to give up on. It was actually super kind of encouraging to see this guy that has some really great work, has made some really ugly stuff. I even go back and look at some of the first things I made in Apple Motion 4 or 5 years ago, I’m just like, “oh my gosh this is so bad.” Who knows, years from now I’ll probably look back at what I’m doing now like, “oohh mmaaann.”

Since we’re doing this as a series do you have any messages you would like to send your future self or questions you would like to ask?

I think if I was to talk to myself in a year, I would ask like, “Did you say no when you should have said no?” I think I’ve found that to be a hard thing and, “Did you create space for yourself to do life giving things?” My propensity is just to work work workworkwork and I think that’s been my reality for the past couple years. And, “Have you been kind to people? Have you invested in people? Have you given what you’ve learned for free away for free?”

We will be following up with Greg Stewart again in a few months as his freelance career continues to grow!
If you have a question you would like us to ask Greg, send an email to

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