Meet Mt. Freelance, an Online Course Built to Take Your Career to New Heights
Interview by Mike O'Donnell / Editor
Every year, we release our creative community’s list of the Top Companies where they want to work—it features the kinds of destinations that make you feel like you’ve arrived at the apex of creativity. The names themselves are towering: Nike, Wieden+Kennedy, Google, and Apple. But how do you actually get there, whether in a full-time role or as a freelancer? If you’re looking to start living the freelance dream, continue basking in it, or are simply looking for ways to fine-tune your independence, meet Mt. Freelance, a 4-level, 33+ lesson online video course built with practical steps to become a master of your freelance career. Why is it worth your time? For starters, Mt. Freelance comes from WNW Members Andrew Dickson and Aaron James, two freelancing veterans with over twenty years of combined freelancing experience at practically all of the companies featured on the aforementioned Top Companies list. And beyond that, it’s predicated on results as well as building your community. To learn more about Mt. Freelance and how it can enable your growth as a freelancer, scroll down to our interview with the Portland-based, professional-freelancing duo.
Who are Aaron James and Andrew Dickson?
Aaron: Over my career I’ve had a quite a few job descriptions, going from Graphic Designer to Art Director to ACD to CD. I worked both at agencies and client side earlier in my career, but for over a decade of my career I’ve been freelance. In between gigs, I work on a few businesses that I’m a partner in. I grew up in a small town in Oregon called Silverton where I worked on farms, logging crews, and was a beaver trapper. Love sports, my family, and checking my email.
Andrew: I’m a freelance copywriter by profession. Sometimes that can mean creative directing a team, doing a little commercial direction, or acting more like a creative consultant and offering bigger ideas or even a different approach to solving a problem—especially as I work not only with agencies but also design firms, interactive shops, and even directly with clients. But I like sitting down and just writing most of all. I also have a filmmaker and performance art background, so I host monthly storytelling shows for The Moth, perform my own work, and even auctioneer a handful of non-profit galas every spring and fall. I’m also a Dad.
How have you navigated your creative professions up until now?
Andrew: I went to film school back when you shot and edited on 16mm, and moved to Portland way back in the 90s to make movies. But I also knew I needed some set experience so I started out as a production assistant and then became a union set dresser. Purely by accident I put myself in one of my short films and realized how much I loved performing, so I got into doing one-person shows around town. Eventually I was commissioned by the Portland Institute for Contemporary Arts to make a show called AC Dickson: eBay PowerSeller, based on my experiences selling stuff on the site. But it was also a send-up of sales culture that made you question whether the whole thing was made up or not. Mike Byrne, who was then the CD on Nike at Wieden+Kennedy, saw it and asked me in to pitch a project. Initially I was pretty skeptical, but then a payment was discussed—let’s just saw it was more than I was making in six months as an artist / eBay PowerSeller.
Eventually I took a full-time job there and spent years essentially learning how to write ads as I was making them. I worked on lots of accounts but Old Spice and Travel Oregon were my favorites. I also got to run WK12 for a few years. About five years ago, I was let go during a big layoff and was suddenly freelance. And it’s been really, really great. I work with all kinds of clients and still get to make work. So I guess I’ve been navigating my career a little bit like a rookie crew taking a white water raft down a class-four river?
Aaron: For me, it’s been about trial and error. I’ve never taken an art class or an advertising class. Taught myself Photoshop on my Apple in college. My first career was in the music industry, working at a independent record label with big distribution. Loved it. Then Napster happened and kids stopped buying music. I set out to do more creative work. I didn’t even get into advertising until I was almost 30. It’s just been one weird step after another, but I realized I was in the right career when the more creative and interesting I tried to make something, the more doors would open.
I got my first ad job in Portland (on a health care account) and after about a year was part of layoffs. But maybe I should restate that, because I was the only one laid off. Anyhow, the next day I was freelance. One project led to another and within 3 months I was scheduled for a day of meetings with different CDs at Wieden+Kennedy to interview for freelance openings. From my point of view, it didn’t seem like things were going too well until the end of the day and the ECDs looked through my book. It took them about a minute and a half to get from cover to cover. But they both went back and looked at a hand-made comic book I had created for my church. (Of all the things right?!?!?) It was about the difference between consumerism around Christmas vs. relational giving. In favor of the later. That weird comic book that I made with a friend in three days ended up getting me my first freelance gig, which lasted for over a year.
Since that time I’ve been in and out of 40+ agencies and brands as a freelancer. Agencies often freelance me for pitches. I’m pretty good at that. I’ve also been a part of some other start-up businesses. One is an online baseball training membership called The Hitting Vault and the other is Howler Magazine, a quarterly magazine covering soccer from an American perspective. I love the challenge and variety that a business can bring. In fact, I had a great experience a few weeks ago guest teaching some graduate and undergraduate classes at the University of Oregon for the School of Journalism’s Advertising department. It was a great milestone that gave me perspective about the journey I’ve been on.
Why did you team up to start Mt. Freelance? What was missing as you found your footing and gained experience, and what do you wish there was more of?
Andrew: We had known each other for years, having overlapped at W+K, but we first worked together as a writer and art director a few years back when a Portland agency paired us on a pitch. We’d go out to lunch everyday and usually ended up comparing notes on freelance. What this place is like to work at, or what rate that place was willing to pay. We were talking about household brands and agencies and at a certain point Aaron was like, “this is pretty valuable information. What if we shared it?”
Aaron: There’s a lot of great advice out there, but not all in one place. And a lot of it is inside other creatives’ heads. For years I thought I was freelancing really well, until I worked on a pitch down in San Francisco and realized the writer I was paired with was making twice the rate I was for the same project. That’s a moment when you really understand that you DON’T understand how this works. He and a handful of other super-experienced freelancers took me under their wing and shared all this great information—about rate but also communicating with clients and how to act on a job so that you get hired again and again. Super valuable stuff. I really wanted to create something that served that purpose for anyone.
“There’s a lot great advice out there, but not all in one place. And a lot of it is inside other creatives’ heads. For years I thought I was freelancing really well, until I worked on a pitch down in San Francisco and realized the writer I was paired with was making twice the rate I was for the same project. That’s a moment when you really understand that you DON’T understand how this works. ”
Andrew: Freelancers tend to really open with each other on a job after they’ve been in the trenches together for a week or two, but less so online. There is a tendency to see other people who do what you do as competition. But there is more work out there than ever before, and the more we help each other be good freelancers, the more clients and agencies will trust freelancers. A rising tide lifts all boats.
Aaron: Mt. Freelance has a lot of practical advice, but we also really want to help people get intentional about freelance. We both started freelancing because we got laid off. So we didn’t really think about what kind of freelance business we wanted to create. We just started trying to get work. What I’d like to see is every freelancer treat their career like the business it is and take the time to set objectives and get really specific about the kinds of work they want and how they want to grow their career. Sometimes we forget we can say no to work we know we don’t like and go after the kinds of work we really enjoy and thrive at.
“There is a tendency to see other people who do what you do as competition. But there is more work out there than ever before, and the more we help each other be good freelancers, the more clients and agencies will trust freelancers. A rising tide lifts all boats.”
How does Mt. Freelance work?
Andrew: It’s essentially an online course of 33 videos that covers every aspect of creative freelancing we could think of, and a members-only community on Facebook for sharing tips, getting feedback on portfolio website relaunches, and crowd sourcing problems that arise. You sign up, take the course at whatever speed you like, and check in with the online community as much as you like.
Aaron: But we know no one wants to take a course. They want the results. So Mt. Freelance is the short cut to results you want in your freelance business. We also know freelancing can be lonely. People want to be part of something that makes them connect with others in the same boat. Building your community is a big part of success.
Andrew: What’s been surprising and gratifying is the range of people who signed up. We’ve had creative directors and art director and copywriters, but also UX designers, account folks, producers, photographers, directors, and even a few small business owners.
Aaron: We’ve also had people who are both new to freelance, but also folks who have been freelance for years. And younger freelancers but also several folks who have had executive level creative roles at really big agencies. All of which is really making the community that much richer and more helpful.
We’ve actually been getting some of our best and more positive feedback from the more senior and experienced freelancers, which is gratifying because that shows us that even they are learning and growing from Mt. Freelance.
What have been some of the challenges?
Andrew: The biggest challenge was just the time it took. It’s one thing to say you know a lot about freelance, another to put it all down on paper, map it out into a coherent course, then write and rewrite 33 videos and upload them to a teleprompter, hire a crew, shoot for a few days, and then edit them so they are watchable. Not to mention building out the website, creating emails, and free blog posts and then marketing the thing. It took us about a year longer to create than we anticipated.
Aaron: To be fair, we did spend a good part of that year freelancing.
Andrew: The other thing has been striking the right tone. We don’t want to be too hard sell. That’s not our style, but we also want to make people understand that this can really help them.
Aaron: We know that marketing anything to people in advertising is really tough to do. How do you get such a cynical crowd to try it out or trust us? We are still working on how to reach folks with the right message that this can really help. We are all “talented” but that doesn’t mean we don’t need a lot of help with areas that aren’t our primary proficiency.
Why should people sign up and listen to your advice?
Andrew: Well, for starters, it’s not canned advice. We based it on our own experiences freelancing for places like Apple, Google and Wieden+Kennedy and combined it with the experiences and advice of freelancers we’ve collaborated with. It’s all stuff we learned the hard way. We didn’t look at any online freelance advice until we were done. And when we did we realized most people are cutting and pasting the same advice and re-writing it. Ours is really our own and based on what successfully freelancing in the creative industry is like right now. And if we don’t cover something, you can pop into the Facebook group and ask us.
Aaron: I would say straight up, Mt. Freelance will make you freelance better. That might mean making more because your website gets better, or you negotiate harder or serve your clients more effectively, which means you get rehired more often. Or it might mean making the same amount but working less because you learn how to work smarter. Mt. Freelance is full of all these pieces of advice and hacks, and if you implement just one or two that you aren’t currently using, that could mean tens of thousands of dollars more in earned income over time.
Andrew: And hey, if you don’t like, it no worries. We offer a 30-day, money-back guarantee!
Aaron: Well, from a practical side, whatever you pay for Mt. Freelance will be back in your pocket within a month. That’s the truth. We’ve had people tell us the course provided confidence to ask for more money. When people report back that they realized they were undercharging and asked for a rate double what they’ve ever gotten before (and they got it!), that’s an amazing thing. It’s certainly not all about money, but when the course and private group empower people to make more, it’s very satisfying.