Forrest is a freelance creative director/copywriter with more than 13 years advertising experience. In his freelance travels he's lent ideas to Weiden & Kennedy, Droga5, 72andSunny, ChiatDay, Facebook, Omaze, and Biden for President, to name a few. He's passionate about creating work for a better world, and traveling the world.

FREELANCER MAGAZINE: So you’re from Oregon, I saw you went to the University of Oregon, but then you went to VCU for grad school. They have a portfolio program right?

FORREST BOLEYN: Yeah they have a Master’s program in advertising. I didn’t know there was such a thing, but apparently there was and I did it.

FM: You seem to have taken a fairly straightforward path toward advertising, which is why it was interesting that you say on your site you’re: “while I try and figure out what to do with my life, I write ads.”  Could you elaborate on that a little bit?

FB: Haha, yeah…I like creativity in all its forms and I always wanted to be a writer in some capacity and I thought I would be the cliché, move down to LA, get a job as a PA and move my way up to writing motion pictures. I gave myself, after graduating from Oregon with a crappy not well thought out portfolio, two options: get into grad school for advertising and do that or, if I don’t get in, move to LA and try the movie thing.  As fate would have it I got into VCU, and that’s the path I followed.

FM: And then you moved to LA anyway.

FB: I always wanted to live in LA, and after VCU I thought I’d move to NY. I always wanted to try the NY thing, have that experience, but there was opportunity in LA waiting for me. I took it and then was ruined by perfect weather.

FM: For advertising, NY, SF, Chicago are real hubs. While LA has tons of ad work it isn’t necessarily the first choice for advertising.  So did you move to LA because you also had this dream of being a writer?

FB: I thought it would be fun to be in a space where people are writing things that are equally and often more interesting than advertising. I never took advertising as seriously as a lot of people. I think It’s a fun job and you can take a step back and relax, and when it doesn’t become the most important thing in the world you can have fun with it. In LA, advertising felt like it was the 4th show in town. You were cool if you wrote movies or you were an actor or you were in the music business. Advertising was like ooh ok. Whereas NY felt like it was this celebrated thing with all this pressure. I didn’t want to be somewhere advertising felt too cut-throat or like the coolest thing you could do. I like that in LA it was the fourth thing.

FM: Tell me a bit about your transition into going freelance. Was it circumstance or did you consciously think “I want to be a freelancer?”

FB: It was mostly circumstance. I was three almost four years full time at Chiat/Day, and then another three years at another agency. It was two back-to-back full-time jobs that were intense, they were grueling. With Chiat it was time to go. I had run my course there, but the second job was hard to leave. It was a small startup that felt like a family, and it was with people I loved working with. I loved working in a space of trying to do good in the world, but I was feeling burnt out and desiring opportunities to work with a different client base than I was being presented at the time. It felt like the way to do that was to try something new, but I was scared to work full-time somewhere else. So on the advice of some friends who had been quite successful freelancing, they said “give it shot, you’ll have fun with it, you’ll get to work on different things, meet different people, maybe find the spot that you want to stay next.” Turns out I like just jumping around.

FM: Were those friends freelance copywriters or just freelancers in general?

FB: A copywriter and actually, at the last agency I worked at, my writing partner had to leave for family issues and the person who replaced him was a freelancer who was all about the freelance life. We actually talked about being freelance partners together and ironically he took a full-time job at 72andSunny right after I went freelance.

FM: Could you ever see yourself going back to full-time?

FB: I’ll never say never, it just has to be the right opportunity, the right client, and the right people. It’s tough because part of the reason I went freelance is I’m obsessed with traveling. I’m absolutely obsessed with seeing our world and our 2–3-week American vacation policy is just criminal.  

FM: Is this something that you were thinking about when considering freelance or something you discovered while freelancing?

FB: It was definitely part of the thought of going freelance, traveling. At my last full-time job I had a trip planned to Croatia and there was an opportunity to work on some maybe super-bowl stuff. There was this career carrot dangled in front of me and it was the only time I cancelled a trip I already booked. As advertising would have it the whole project got pushed and eventually tabled. My friend who ended up going talked about the most amazing trip they ever had and I thought, “why am I putting myself in this position where I’m fearful of taking time off.” I found when freelancing I could tell people “I’m just going to take a vacation.” When I was full-time they would say “no you’re not,” but now they just say, “tell us when you’re back.”

FM: If opportunity allowed would you try and remain remote most of the time?

FB: That is my goal. To each their own, I will not put don’t anybody’s way of working. Personally I work the best when I am given space. For me the routine whenever I get an agency job where they say I have to come in, is me trying to find a space to work that inevitably isn’t in the office. I can’t do the open office environment, I get too distracted. I can’t do headphones, I need silence, I need a door that closes. It’s always frustrating when places aren’t open about it because they have their “way of working,” but I give you better work if you give me space to do it.

FM: So given that, and your penchant for travel, have you considered working remotely and living somewhere far away like…Singapore for a year?

FB: I’ve thought about it…short answer no. I like having a home base and I’m moving toward a more adult life here in Oregon.  I’m getting married soon, I’ve got a dog. I just like having a home base to come to, also when I travel I just want to explore. I don’t want to feel like I’m on working vacations.

FM: Obviously a lot of people moved back home during the pandemic but were there other factors pushing you to move back to Oregon?

FB: The biggest was I had bought a home in Portland a few years ago and was renting it out. My then renters moved out in August of 2020. That was a scary moment and I thought “oh my god I have to try and put new renters in a house during a pandemic.” And if I couldn’t find someone, or if whoever I found couldn’t pay rent, I’d have to cover my expensive Los Angeles rent as well as the house. That was a terrifying prospect. That combined with the fact that my fiancé and I were stuck in a one-bedroom apartment, both trying to work from the dining room table.  It just made sense to occupy the house and have our own offices with doors that close, and pay a cheaper mortgage than we were paying rent in LA. See where things go from there.

FM: Since moving to Portland are you still working with mostly LA clients or are you working with more Portland clients?

FB: It’s been both. I was working with a NY agency back in LA and still am. I just started working with a Portland agency for the first time since coming here, but it’s been a mix of everywhere for a while. Most of my jobs while in LA were also in LA, but I’ve always worked with agencies across the country no matter where I was.

FM: Just looking at your resume you’ve worked with a ton of different shops while freelancing, and I was wondering if you could give me the most common scenarios in which those connections starts.

FB: In the beginning it was me blasting the entire universe and trying to make as many connections as I could. Now it’s mostly people reaching out to me. At the beginning of the year I’ll send an email to my usual roster as a heads up, or general run down of my availability, but I have been extremely fortunate in that I got a great network through Chiat/Day. It helped to work at a huge agency as my first job. Back then the creative department had 100+ people, who now have all since gone off and worked all over the place, so knowing all of them and proving myself in front of them have led to a lot of connections. Plus my VCU peers have also opened doors for me. This year has especially been a good one. I get an email weekly if not multiple a week saying, “are you free?” Good problems.

FM: Great problems. Would you say is there an average length these contracts last or do they vary completely?

FB: It’s usually one of two camps. It’s either months on end, or two to four weeks. It’s either a long-term whole project deal, or a quick, last round, we need something solved in a hurry.

FM: When someone asks, “what do you do?” do you say copywriter? do you say freelance copywriter? do you just say writer?

FB: Depends who asks haha. Depends on who I’m trying to look cool too. I try to avoid advertising because so many people have such negative conceptions of what this industry does, and rightfully so. Usually I just say copywriter or I work in advertising or I write commercials. They then ask “have I seen anything you made?” and I say no.

FM: Do you think of yourself as a freelancer?

FB: Absolutely.

FM: In however many words you need, how would you define what a freelancer is?

FB: I think of myself as just a problem solver. When you reach out to me it’s because you need something done and either you haven’t cracked it because the clients been a pain, or you’re just lacking resources, or anything. I’m the solutions guy and I very much enjoy that role. Unlike a full-timer where there are often a lot of politics and relationships you need to deal with as part of the job, I like doing the work. To me just being able to come in and focus on the work is the part of advertising I like the most.

FM: Would you say you have a lot of friends who are also freelancers?

FB: They’ve come and gone over the years. Some people don’t have the stomach for it and I can understand that because it’s terrifying when you don’t have a job lined up and there are bills coming. Right now I’ve got friends who just went back to full-time because they wanted a title increase, or they went freelance to pursue other things and were done with that. I also have friends who just left full-time for the freedom aspect of freelance and to take a break from the grind and allow themselves to vacation.

FM: Would you say most people who freelance do it for similar reasons to you?

FB: I think there are lots of reasons to leave the stability, or what they consider stability. I think everyone’s trying to figure out something else, they’re just not sure what that next full-time job will be so they’re testing the waters. Originally that was my thought. “Let’s freelance for a year or two and see what’s out there and then you’ll land somewhere that feels right.” I’ve been at lots of places that felt right but I loved knowing that there was an end date too. I loved that there is a vacation or a break on the horizon and I find I do better work with that in mind.

FM: Would you say freelancing has given you more time to work on personal projects?

FB: It’s giving me more time to talk about working on personal projects.

FM: Okay hahaha.

FB: I’m the cliché in a lot of ways. It’s hard when there are no deadlines. I’m always frustrated because when I take a freelance job, I’m amazed by my ability to get things done because I procrastinate so much but I always make my deadlines. I can’t flip that same switch on when it’s just me. I take writing classes sometimes, and I have the fantasy of writing a novel and I’ve been working on some short stories. Those things are fun side projects, but the reality is I’m still trying to find that perfect balance. It’s hard to write for fun when you spend all day writing for work, and when you finally get done with work and have time off, it’s hard to sit in front of a computer when you finally don’t have to. But I’m trying, it’s an everyday struggle is the short answer.

FM: What would you say are the toughest parts of freelancing, or the parts that would make you want to go back to full-time?

FB: A lot of people complain about the lack of stability or the lack of control. I haven’t had a lot of those issues. The toughest thing is to let go. If you need to be in control, and want to feel like you’re work is totally your vision, that’s tough as a freelancer. The way I rationalize it though is working in advertising you learn that your work is never your vision, it’s the clients’ vision, and it’s such collaboration. I can accept that and I try to make it the best I can. But then the writing stuff I do on the side that’s my baby. That’s where I scratch that itch. That’s where I get to control what it looks and sounds like, and make it the exact way that I want it to be. It keeps me sane. When something doesn’t go right at work, I can go back home and do my project the exact way I want.

FM: Would you say that the majority of freelancers you know work in advertising? Is your idea of what a freelancer is very much based in the world of advertising?

FB: Yes, until this year. Earlier this year my fiancé who works in fashion took her first freelance job. Before this year when I thought freelancer, it was synonymous with advertising. Now I’m rooting for her to make that career work and if we could take time off together that would be great. Although on the other hand if she could stay full-time and provide all the health insurance and the stability that would be even better haha.

FM: Haha, well thanks so much Forrest.

FB: Yeah of course. I like this life and I encourage others to not do it so they don’t take it away from me.