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Hustlin': How I Became My Own Mentor in a Freelance Economy

As the "contingent" workforce grows, we need to embrace the freelance hustle.

In our weekly Hustlin' series, we go beyond the pitying articles about recession-era youth and illuminate ways our generation is coping. The last few years may have been a rude awakening, but we're surviving. Here's how.

At 32 years old, I’ve never had a real job. Or more accurately, I’ve had a shitload of them, just never one at a time. I’ve never had a desk where I was expected to be sitting during work hours, never had a chat by the water cooler (does that really happen?). I’ve never even had a boss.

And no, I’m not a trust fund kid whose parents have been secretly slipping cash into my checking account all these years. I’m a serious freelance hustler, or to use my dad's preferred term, I have a 'portfolio career." I write books, pen op-eds, blog, speak at colleges and conferences, do communications and strategic consulting with a slew of awesome social justice organizations, ghostwrite, serve as an individual writing coach, and, occasionally teach. I’ve made enough money over the years to afford health insurance, splurge on books and vintage clothes, and even buy my own little home-sweet-home in Brooklyn.

Of course, not all of my peers have been so lucky to “choose” the freelance lifestyle—sometimes more accurately described as underemployed. Fast Company optimistically described the “Flux Generation”: "a mind-set that embraces instability, that tolerates—and even enjoys—recalibrating careers, business models, and assumptions." But often, this just means plain ol' unemployed and underutilized. Nearly half of Americans adults ages 18 to 25 are jobless. And worldwide, there are now 3.3 million unemployed workers between the ages of 25 and 34.

The fact is, freelance is becoming the new 9-to-5, whether we want it to or not. Tom Fisher, writing in the Huffington Post, reports that “contingent workforce,” meaning the self-employed, freelancers, or "accidental entrepreneurs" laid off from full-time positions, will make up between 40 and 45 percent of the workforce by 2020 and become a majority by 2030.

Early on, I realized this kind of "contingent" work was not going to come with an instruction manual, nor with any one-stop-shop mentor. I’ve had the support of a clown car’s worth of incredible people along the way—nonprofit directors, journalists, social media gurus, emotional intelligence experts, community organizers, grassroots activists, teachers, conflict mediators, and everyone in between. My friends, probably more than anyone else, have taught me wise lessons about surviving financially while doing work that matters to me in this strange economic time. Each of these people has given me insight into the kind of person—both personally and professionally—that I wanted to be, but none of them could advise me on all the various bells and whistles that animate my idiosyncratic career.

For that, I realized, I really needed to count on myself. So over the years, I’ve morphed into my own career coach.

What does that look like in practical terms? First, I have a strategic plan that I revisit once a month or so. Dorky, I know, but it helps me stay centered in the winds of career chaos. If I get job offers that I don’t have a gut instinct about, I can hold them up to the test of my strategic plan. Does this fit into what I said I wanted to be doing with my energy? Or will this be a distraction from the path I want to be on right now?

I balance these calculations with my projected income—also a feature of the plan—which helps me know when I need to be hustlin’ harder than usual, or when I can be a bit more choosy about the jobs I take on. There’s nothing like realizing you don’t have enough money in the bank for some basic expense—an experience every freelancer has from time to time—to teach you that keeping a chart on your projected income is totally worth the annoyance.

It also allows me to find that happy medium between reactive and proactive. Some opportunities have grown like beautiful little dandelions right in the cracks of an existing relationship. I didn’t have to tend or cultivate the projects; they just happened. But some things are a bit more elusive. Sometimes you have to go after a collaborator or a work gig. I’m not big on "networking"—at least the version of it talked about in women’s magazines and at some alienating conferences. But I do believe in "friend crushes." If someone does particularly awesome work, or has a way of looking at the world I find really unique, I will go out of my way to get to know them. It’s never with a set goal in mind, but more with the faith that putting a bunch of amazing people in my orbit will guarantee cool opportunities arising down the line.

To this end, my strategic plan features all kinds of useful lists: work that's in process, work I’d like to do in the near future, people I’d like to work with, kinds of work I realize I hate, kinds of work that really lights me up, skills I’d love to learn. Some of this may seem intuitive, but I’ve found that it can be hard to keep track of in a busy life.

There is something very powerful about putting things in writing. So much of what I’ve written down in my strategic plan has come to life not by some mystical force, but by the determination of my own intention. Once I’ve written something down—say, a new skill I want to learn—I start to walk around with a radar for opportunities to make it happen. It’s the organic byproduct of the seemingly inorganic practice of keeping the plan current.

The plan also contains my own personal mission statement (again, I wave my dork flag proudly). Theologian Fredrick Buchner says that you must find "where your deep gladness meets the world’s deep need." For me, that sweet spot is where true fulfillment lies, and it can be hard to find. When you’re a freelancer, it’s easy to feel like your life is being spent in a million different dribs and drabs, especially if you initially didn’t choose to make your living piecemeal. What does it all add up to? When you’ve got a mission statement, and you can check the different projects and jobs you’re doing against it, you have a greater sense of the whole.

I know I'm ridiculously blessed to have chosen freelancing and have it work for me. I also know it doesn’t come easy. Without the guidance of a supervisor or the wisdom of a mentor who understands the totality of my career, I have to be my own mentor, hold myself accountable, and give myself the space to dream.

Photo via (cc) Flickr user Matt Biddulph.

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