From Higher-Up to Hired Gun: Delayed Observations from a First-Time Freelancer

I had risen just a bit too high, and had a few too many family responsibilities, to indulge in soul-searching. Partly, I just wanted another angle on the profession I’d chosen. To gain perspective. To grow. To stave off boredom. And wouldn’t this be nice: being home for dinner, asking my kids about their day, and actually listening to their answers.

My movement up the creative ranks had been going almost exactly as planned—in a generally linear and vertical direction, with some purposeful meanderings into new territories to diversify my experience. I’d worked for traditional and digital agencies, mid-sized and giant ones, independents and holding companies, all over this country and a handful of others. As of October 2014, I held the “Executive” title at a growing integrated agency, and had accomplished much of what I’d envisioned within that organization. My professional life was eerily close to what I’d imagined way back in high school, when I was projecting my future for college applications.

Time to revisit something I’d long been pondering, but had never done. Freelance.

It’s incredibly common in our industry, of course. And much has been written about the labor transformation to a freelance economy. But why would I make that shift when I didn’t have to? To condition myself for a macroeconomic trend? Not quite. My motivation came from several directions. There was something pure and almost romantic to me about this life where I get a real-time view into my market value, and am paid for what I deliver. With management off my plate, I could refocus on my craft. The variety appealed, too; while most ambitious creatives prefer a mix of assignments, for me it was as much about studying a bunch of organizations’ cultures, management styles and efforts to differentiate themselves. And naturally, I was drawn to the flexibility to pursue personal endeavors that might make me rich and/or venerated after my death—books, products, business concepts, pornographic enterprises, new religions, etc.

I had contacts. I had a selling proposition. I had a litany of assurances for my wife who worried about disrupting the steady paycheck. Ready, set, jump!

It’s been about six months now. While I haven’t yet seen a full year’s cycle of ups and downs, to my mind, this is the perfect moment to reflect. It’s just enough time to have a general sense of what works and what doesn’t, with a clear memory of what I expected from freelancers when I was on the hiring side. I often imagine how I would have responded to the ways I market myself, conduct myself when hired, and serve up my deliverables. (I could be rather picky and demanding, and would probably have given the freelance me a severe bout of anxiety.) In other words, my circumstances are somewhat different from most freelancers I know, which may make my observations—and approach—of some value to you.

Judge for yourself…

The Year of Hustle

Because I’m really looking to make a go of this, this first year is all about the hustle. Build my network. Get inside as many places as possible. Deliver the goods. “Freelance ECD + Writer” is my job, and it gets the full weight of my attention. If I’m between assignments, my days are spent casting more nets. My plan is to establish a number of “core accounts” in Chicago, where I live, supplemented by other agencies around the country whose names look really good on a resumé. Chicago agencies tend to be more enamored of coastal creatives than they are of the locals, so to keep things entirely local wouldn’t particularly help my market value here. Besides, going national means more prospective clients to fill my calendar. And then there’s my thing about getting an insider’s view of more places… and if one of those places can be, say, Apple, that’s a hard opportunity to pass up. After a year of having been built this foundation, I’ll weave in more of the other benefits of the freelance life. More family time. Personal projects. Thorough self-actualization.

Hello, and Hello Again

One of the things I’ve enjoyed most is the speed-dating: meeting lots of new people, fast. Not to mention getting back in touch with some of my favorite people at agencies past—people whose company I enjoyed, but who, because we’d never fully entered the friendship sphere, almost ceased to exist the day I moved on. To this end, I’ve done my own version of multivariate testing, and the email subject lines with the highest response rates have been “Hello” and “Hello again.” Point is, it comes off as a conversation, not a sales call. When I was on the hiring side, I saw all sorts of approaches, including one guy who comped up an Adweek news feed with a feature on his extraordinary future performance at my agency, followed by a sycophantic piece about me—with a photo he’d grabbed from one of my Facebook albums. Was it creative? Maybe. Did it creep me out? Absolutely. In general, I find it much more effective to be a (non-stalking) human than a bullhorn. On a related note, more than a few of my freelance friends will occasionally say to me, “I’m thinking of reaching out to (agency/person).” Um…exactly how much meditation does it require to do that? Why not just do it, and then do it again 20 times a day, to 20 different people?

Market Value vs. Self-Worth

The response to my entry into the freelance marketplace has been good so far. Really good. That’s not to say I’ve come anywhere close to meaningful conversations with everyone I’ve approached. It’s a timing and resources game. If my availability doesn’t line up with the project start date, then there’s no conversation to be had. I hear lots of grousing from people who just can’t fathom why a creative director or recruiter won’t make the time to get back to them. (This seems to drive most of the acrimony in the Agency Spy comments section.) But I refuse to take it personally when I don’t get a response from someone who has no need for me. Even if the timing is right, my skills or sensibilities—versatile as I think I am—won’t always line up with what the agency needs at that moment. Maybe, just maybe, the person looking at my body of work simply doesn’t like it. That’s okay, too. We don’t all watch the same movies, listen to the same music or like the same portfolios. And then, even if I’m exactly the right person at exactly the right time, they might not have exactly the right money. In these cases, rather than feeling undervalued, I simply measure up the opportunity and determine if there’s something to be gained beyond the money—a name-brand agency on my resumé, a new relationship, a different challenge, or a creatively satiating exercise. If not, I’ll respectfully pass. It’s not personal, it’s business.

My Full Arsenal, or Just the Dart Gun?

What I can contribute from my ECD experience isn’t necessarily what’s wanted or needed. Often, I’m just called upon to concept and write (and I presume they expect me to be proficient and prolific at those things). I try to be attuned to what will make the project and the people successful, but even better is to ask directly: Which of my capabilities will be most useful to you? In the past I’ve hired some very senior freelancers who, when I didn’t take full advantage of all they thought they could offer, acted like they were racehorses giving pony rides (a favorite expression from my friend David R. Mitchell). It’s a pain in the ass, especially for the creative director with dozens of other egos to manage. By all means, over deliver. Just don’t over deliver the wrong packages.

Being There, but Not Really

The thing I miss most about full-time isn’t the health insurance, it’s the full inclusion in the agency’s identity, culture and events. I can form strong bonds with my project team, and have a good chuckle with old acquaintances at the coffee machine, but the moment that “all-agency meeting” notice goes out, it’s clear that I’m on the periphery. Man, I used to lead these meetings! (And the audience felt obliged to laugh at my jokes.) At my last job, I once walked around our open office checking the work on the walls, delivering edicts, forming impromptu meetings, when someone finally informed me I had a long tail of toilet paper hanging out of my pants. Embarrassing, yes, but as a full-timer I was contributing to the trove of stories people share at agency happy hours; if I were a freelancer, I might never have been informed, and the amusement at my expense would have been more furtive. It’s clear my relationship with the agency has become purely transactional. Now, I could go on about how the only real relationships are interpersonal, not organizational. Having driven culture development, though, that would be disingenuous of me. One drives the other, and vice versa. I said earlier that there was something romantic to me about the purity of this relationship, but it’s proving to be the biggest trade-off for all the benefits. There’s not much romance to sitting in an empty cube farm, wondering where everybody is, then hearing the entire agency laughing and clinking bottles somewhere down the hall.

Sleeping Through the Night

Being one who focuses on the positives, I’ll end on the biggest upside. The freelance life is significantly less stressful. Okay, okay, I haven’t yet experienced that dry spell that has me fretting about how to pay the mortgage; it’s sure to come eventually. For now, let me have this, all right? I’m not getting bombarded the moment I step into the office. Not getting buzzed at all hours of the night. Not spending all day in meetings. Not expending my psychic energy on office politics. Not conspiring against that person who’s angling for my job. Not waking up at 3 AM shivering in a pool of sweat, terrified of that life-or-death presentation. Going into all these agencies (and that one non-agency in Silicon Valley), I see so many people running around like the sky is falling, driven more by urgency than importance, acting out of fear of a bad meeting with the boss, client or committee. Freelance can sure give you some healthy distance from that feeling. Of all the emergencies out there, an advertising emergency is pretty low on FEMA’s list. I can see that more clearly now. Which doesn’t make me unsympathetic or complacent. It makes me clear-eyed about what actually matters, and how I can contribute to that. If and when I go back to that big full-time job, I don’t want to let go of this perspective. Pretty sure it leads to better decisions, professionally and personally.

Speaking of which, will I? Given my carefully constructed, exuberant yet pragmatic view on the freelance life — and the fact I took the time to write this piece in the first place — will I ever go back to full-time? To be honest, yes. Probably. Even if I publish a best-selling series of novels, give rise to a new religion from the ashes of Scientology, and establish the best relationship with my children in the history of parenthood, I’ll likely make my way back into a management role at some point. Freelance is activating some dormant parts of my brain, and I love that; but there are other parts that will atrophy if I don’t ever lead the creative endeavors of a matrixed organization again.

For now, allow me my revery. I’ll see you at the coffee machine, and we’ll have a good chuckle.

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About the Author:

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John Carstens, Freelance ECD+Writer

John Carstens is a seasoned and cured creative director, and copywriter by trade. He’s pitched, preened and written his prose at the likes of SapientNitro, Cramer-Krasselt and TBWA\Chiat\Day, and to show for it, has a plastic crate filled with awards in his basement. He’s currently freelancing nationally while residing in Chicago with his two mildly eccentric children and tolerant wife. Follow him at Twitter, Pinterest and Instagram @carstensible.

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From Higher-Up to Hired Gun: Delayed Observations from a First-Time Freelancer