Happy Freelance-a-versary

15 things I’ve learned from two years as an “agency of one”

Two years ago I left a great job that I loved to step out on my own and go freelance as a writer and creative director. At the time, I told myself, “Let’s give this two years and see how it goes.”

Well, two years are up, so I guess my report is due.

Here are 15 lessons in four sections — what I love about freelance, what I miss about a staff position, other things I’ve discovered, and some thoughts about what’s next.

What I Love About Freelancing

1. I love making stuff and I love focusing on the work. I knew this before, of course. But the further you move up in advertising, the further you move away from actually making ads. Coming up with ideas, writing scripts, presenting work, selling a campaign, working with directors, casting, the shoot, the edit, making creative decisions — THAT’S why I got into the business. Those things are a hell of a lot more fun than meetings and management, which is what a lot of full-time staff positions become. AND, I’ve been very lucky in that I’ve landed freelance gigs where they’ve let me go on production and actually make things.

2. I love the clarity. Freelance life is transactional— you pay me X to do Y. I’m either on or I’m off. As long as we’re both clear about expectations, there’s no gray area and both parties know where they stand. Neither I nor my clients feel taken advantage of because we’ve defined the terms of engagement. Compared to the ambiguities and insatiable expectations of most staff roles, it’s been a nice change.

3. I love the variety. I get to work on a wider range of brands and briefs. I get to work with a wider range of people, at different agencies and at different clients. I think it’s good for my brain and my creativity to move around and work in different categories and I think my work is better because I’m not trying to plow the same territory over and over again.

4. I love the control. Now I don’t want to oversell this part of it. Freelancing is a service business and while it’s fun to think of yourself as your “own boss,” you really have LOTS of bosses. But you do have more control over your life. You can choose to take an assignment or not. (Trying doing THAT as a full timer — most places don’t give you any such choice.) And you have more control about carving out time for your family, which is important to me at this stage of my life with young kids. (My wife says I’m in a better mood since I started freelancing; I suspect this is a big reason why.)

What I Miss About a Staff Position

5. I miss making decisions. (See that “many bosses” bit above.) You can do your best work and give your best advice, but as a freelancer, it’s highly unlikely that you’re going to be making the final call. If you’d gotten to a place in your career where you DID get to make the big decisions about the work, you have to make your peace with not calling the shots.

6. I miss helping to lead a place. Yes, you are leading your own freelance business and that’s rewarding. But it’s different than being part of a team that’s building an agency/company and leading the way forward. I miss the chance to have a larger impact on an organization.

7. I miss the status that comes with the full-time staff role. There are people outside the biz who think “freelance” is a polite word for “unemployed.” Our jobs (title, the reputation of the agency, the halo that comes from the work) can be a big part of our identity. You give up some of that status when you go out on your own.

8. I miss benefits. You really have no idea how screwed up health insurance is in our country until you become your own benefits administrator and have to figure out all that shit by yourself. It sucks that nobody hands you a packet with your benefits, nobody matches your 401K investments, and that there’s no paid vacation anymore.

Other Discoveries

9. I am an agency of one. As a freelancer, you’re really running a one-person agency. Your reputation is based on your creative output and how pleasant and productive it is to work with you. (Here are some tips on how to do it well.) Also, you have to handle a bunch of things that others used to handle for you: new business, account management, HR, IT, and more.

10. Some agencies use freelancers better than others. I’ve been at places that have a well-oiled process for moving temporary help in and out of the organization, that give me great opportunities and make me feel valued. Some places are…less well-oiled. (Here are some tips for agencies that want to be one of the good ones.)

11. It’s easier to plug in as a freelance creative than almost any other kind of freelancer. Given my eclectic background, when I went out on my own, I imagined that I would take on a variety of different projects — PR, communication consulting, and new business development, in addition to creative work. But I discovered a few things: 1.) There’s a greater need for good creatives, 2.) There’s a well-established system and protocol to bring in freelance creatives, 3.) The assignments are longer, and 4.) They pay better.

12. There’s a difference between agency assignments and client-side assignments. In the San Francisco Bay Area, there are lots of direct-to-client opportunities. While the experience varies from company to company, and there are definite perks associated with working client-side (free lunch, anybody?) I’m definitely more sympatico with agency peeps. The healthy cynicism that’s seen as an asset in agency land (“that idea is bullshit”) is not always appreciated by “new economy disruptors” (“we’re changing the world with our app!”) [More on the differences between the two here]

13. Having side projects is good for the soul and good for your “brand.” (Ugh. I just referred to my “brand.” You can punch me next time you see me.) It’s been nice to have a few ongoing side projects that are all mine. Whether it was my columns on advertising, the LinkedIn project or the 97% Conference twitter feed, they have been fun to write, helped me make new connections, generated some nice press, and led to new assignments.

14. Nobody has it figured out. One reason I went freelance was the chance to work with lots of different agencies and brands to see who “has it figured out.” Guess what? Nobody does. There is no foolproof formula. Every place is just doing their best to determine what’s next, figure out the right service offering, land clients, make great work, etc.

What’s Next?

When I went out on my own back in 2015, I thought that two years would give me all the insight I needed and that I’d finally know what I want to be when I grow up.

I don’t.

I like freelance. I’m on a great long-term assignment right now and am working with people I really like. It feels like I could keep doing this for the foreseeable future. But is anybody really going to hire a 50-year-old copywriter? You know, in 20 years when I turn 50. 😉

I’ve had a number of full-time staff job offers in the last two years, two of which I considered pretty seriously. Ultimately, they weren’t the right fit. But that’s not to say the right opportunity won’t present itself. I definitely have a clearer sense of what I’d want from a staff position and what I’m worth.

I’m often asked if I’d like to start my own thing. I’m not sure the world really needs another agency, but I suppose that’s a possibility at some point.

So that’s all a rambling way of saying, “Who knows?” Our industry seems to be in a perpetual stage of expansion, consolidation and disintegration, so it’s hard to say what the future will bring.

But that brings me to my final lesson:

15. Be thankful. I’m incredibly grateful for the past two years. I’ve met a lot of new people, rekindled connections with past colleagues, made some good work, and learned a ton. It’s been fun and challenging and I thank all of you who have supported me, in various ways, during the journey.

I say this all the time, but this work that we do, it ain’t diggin’ ditches. I get to make stuff up for a living, have a lot of fun doing it, and am well paid. That’s a pretty damn good gig.

Let’s see what happens next, shall we?

When he wrote this, John Kovacevich was a freelance writer and creative director in San Francisco. Later, he pulled in his freelance shingle to go full time at an agency. And then he decided to open his own shop.

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