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The Free(lance) Life, Freelance & Friendship

Am I a better writer or a better friend? Just something I’ve contemplated lately (and then contemplated whether it was even worth contemplating, but… here we are). Looking back at my first handful of months as a freelancer, it’s clear I’ve been granted the majority of my opportunities by friends. Some directly and some indirectly. I guess 25 years in the Minneapolis advertising market has a way of getting you all networked up. Unlike others though who are experts at drawing lines and categorizing relationships (LinkedIn-only vs. Facebook-worthy vs. “What are you up to Friday night?”), I’m apt to turn more of those connections into friendships, at least on some level. I can’t help it. I think I just like people.

But I’m not entirely sure why I’m even writing this. Maybe it’s just a roundabout way of saying thank you to all my friends who’ve afforded me this ‘in’ of sorts. A pledge that I’ll always do my best to make them look extra good in front of their bosses and clients. A chance to assure them I’ll never take their kindness and their faith in my abilities for granted. Or, tapping into my insecurities, maybe I’m writing this as an admission to myself (and to you, of course) that I may not have otherwise been their first choice. If you’ve spent any time in this advertising community, surely you know there’s an abundance of accomplished – and available – wordsmiths out there. Frankly, it’s an honor to just be considered an alternative to some of these local who’s whos.

So here I am, trying to find comfort in that grayish area smack dab in between what you know and who you know. True, during the last quarter of a century spent toiling at numerous shops, working with ad school students and attending myriad industry events, I’ve made a lot of good friends who today are creative directors, agency owners or even potential clients – meaning, I’ve got plenty of people I can call on. Then again, I’ve also worked my ass off to become a better writer, gained a wealth of knowledge and knowhow, helped win new business along with industry awards, and earned a mountain of trust over that time – meaning, I believe I’m someone who’s worth being called on. If it sounds like I’m rationalizing, that’s because I am.

This much is undeniable: I love working with my friends. When you consider the lack of medical insurance, 401K and PTO, having the freedom to choose who you work with is actually one of the major benefits of being a freelancer. I don’t see it as mixing business with pleasure; rather perhaps just a more pleasurable way of doing business. We text instead of email. We have a shorthand that works every damn time. We can be brutally honest and completely inappropriate. We can piss each other off, huff and puff, then go get lunch like nothing happened. Most importantly though, we always want what’s best for each other, and we never let the other fail. In fact, thinking about all this stuff kinda makes me miss working full time at an agency with a really close-knit team. But only kinda.

I realize it’s a very small sample size, but to this point, my freelance career has certainly gone far better than expected. However, if I remove the rose-colored specs, long term I likely won’t be able to make it relying solely on my friends for work. Moving forward, I’ll need to be more diligent at reaching out, re-reaching out and re-re-reaching out so I can add on to my tried-and-true network. I’ll need to seek out projects with complete strangers. I’ll need to be okay with being a stranger. I’ll need to whittle down entirely new shorthands. And I’ll need to earn that all-too-important mountain of trust all over again. You know, so these people will keep calling me back. And so we can eventually be friends.

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