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The Moment I Was About to Give Up, I Turned My Freelance Career Around

After what felt like six years on a turbulent flight, the last thing I want to do is talk. In fact, I’d rather gouge out my eyes with an acetylene torch, but my Lyft driver’s energy is so infectious that I secure my earbuds in my pocket. I listen. He’s outfitted his car with signs proudly boasting his five-star rating after 5,745 rides. He has chargers, water bottles, spearmint gum, and magazines at the ready. All you need to do is ask. What do you need? Just ask! Driving for Lyft is his full-time job and he loves it.

This man is a teardrop of light in my cold dark.

I can get a job. I can make lattes at Starbucks, but can I get flexibility? Can I get my life when I want it? Can I turn off for a few hours, pull over in Santa Monica, and walk on The Promenade, the beach? Can I do what I want when and where I want to do it? My driver nods in his mirror, confident and assured. This is where we’re headed, he says. FlexibilityMy time.

My driver asks me where I’ve from because I sound east coast. I tell him I moved here four years ago from New York because I wanted geographic, physical, and mental space. I suppose I wanted to see time as more than a unit of measure, but as something that needed to be carefully tended to, preserved.

What I hadn’t expected was how hard it would be to uproot my career, my network, my life. Here I was, on the verge of 40, and I felt stalled in the in-betweens. Life shouldn’t always be this hard. When does it get easier? Does it get easier?

I kept saying this as I submitted my resume for the jobs I didn’t want, to work for companies I didn’t believe in. As part of one interview, I gave a presentation to a packed room of incredibly smart and passionate people, and it occurred to me that everyone in that room was white. In another interview with another company, I was told that my creative writing would be monitored. Recruiters told me I’d have momentum — I’d cease getting the overqualified or “fit” lines, which is a translation of you’re too expensive or you’re not 25 — if I scratched the first four years off my resume to give the impression that I’d graduated in 2001 instead of 1997. Recruiters repackaged my resume into a neat and tidy box, eliminating everything that was unique about me and my particular experience, why I wasn’t just another marketer with 20+ years of experience.

With a stroke of the delete key, I’d been reduced to a series of bullet points. All traces of the story I’d created, a life I’d built and assiduously believed in, were erased. Apparently, I was a marketer who needed to be more marketable.

Once, someone told me that it was good that I didn’t look my age. But we’re not here about that.

After consulting for six years, I started looking for a job because I grew tired of financial instability. Of having to constantly farm, cultivate, and weed. Although I prefer to spend much of my time alone, I missed human contact because my cat could only give so much. I started looking for a job because I was ashamed of where I was in my career. Had I done enough? Was my work significant? Had I reached my best-by date? I asked myself all the big questions, and I suppose this is what a mid-life crisis looks like save for the sports car and Botox injections.

I went a few rounds for a few months with a few companies, and I realized I was making the hardest sell. But I wasn’t pitching hard for them to hire me; instead, I was selling these companies to me. I created a fantastic fiction, but I wasn’t buying the story. I knew I wouldn’t be doing the caliber of work I’m doing now, and after I boarded the last plane back to Los Angeles, I decided to try to fix everything in my business that went off the rails wrong.

I tell my Lyft driver all of this, and he laughs and swats the steering wheel when he says that I’m reclaiming my time. In front of my home in Los Angeles, he turns around and tells me that I need to make my life work for me because it seems as if I’ve spent too long working for it.

In a span of two months, I radically changed my business — and more importantly, my attitude. Because here’s the thing — you can complain about your life or you could do the hard work to change it. There’s no nobility in posting screed after screed if you’re not foraging your way to a solution.

Here’s how I did it.

I. Just because you’re good at something doesn’t mean you need to be doing that something.

But here’s the thing — I’d much rather be at the beginning of things. I’m also a published author, and I’ve realized that crafting a positioning statement is no different than writing a poem because there’s no room for fat — you have to be economical with the words you choose because every one of them counts. Architecting a brand reminds me of developing a novel outline. Both serve as a blueprint that builds the foundation of a house, which could weather any storm if you plan it right. If you take time with the schematics and make the careful measurements.

But marketing plans exhaust me. I glance at a PowerPoint and an acetylene torch and consider the options. Right now, I have one left to complete, and then I’m done. I stripped down my service offerings on my website to free myself up to do the work that bolts me out of bed in the morning. I’m built for the beginnings.

You don’t have to offer everything in your consultancy model simply because you can do it well. Offer the work that challenges you, moves you to do your best. I’m constantly refining my brand development process. I’m building more sophisticated methodologies, using the latest tools, and crafting simpler, compelling stories. Even after twenty years, I consider myself a hungry student.

II. Yes, it’s possible to network without having to leave the house.

The bother is looking up from my work to find that time has crept by, rent is due, and I don’t have another project lined up because I’m 43 and I still don’t have my pipeline tight. Closing business has never been a problem — I find it challenging to devote a portion of my week to harvesting relationships. Because while that harvest won’t yield a crop today, continuous work and crop rotation will sustain me.

So I set aside time during the week to focus on peer relationships. I keep up-to-date with my B&C network with Skype, Zoom, or Facetime “dates.” My B&C network is comprised of LinkedIn acquaintances with whom I used to work or have encountered online. Video catch-ups are perfect because you save commuting time and money. And if you live somewhere where networking is challenging, this can be the perfect solution to stay connected.

Let’s be clear — this isn’t some smarmy strategy. I’m all about cultivating relationships where both parties mutually benefit, but I don’t come with an agenda other than to chat about our careers, challenges, and trade stories and advice. Being transparently transactional never works.

I often find that most of my leads come from my B&C extension networks because you have access to a group of people you wouldn’t otherwise be privy to. Now, I don’t reach out to randoms, instead, I make a list of people whom I admire, peers who are putting out smart thought leadership or jive with me philosophically. I make an effort to read their feeds and keep up with the medium or blog posts. Do your due diligence. Make an effort to show that you’ve done your homework in establishing a peer friendship with someone you genuinely respect.

With my B&C contacts, all my previous encounters have been friendly, and we say that we need to catch up, yet we never do because life gets in the way.

III. I finally diversified my income.

This year, I’ve managed many copy projects from B2B articles to website and marketing collateral copy. The timelines are clearly defined, the work is manageable, and the onboarding swift.

Nurturing my calendar is important from both a project management and new business perspective.

IV. Partner with smart people so you’re not always alone.

As your consultancy grows, you’ll notice that you’re referring people to do work that’s not in your skillset. I’m constantly making referrals for CDs, graphic designers, SEM pros, and brilliant tacticians. Referrals breed good will across the board and people will reciprocate. It only occurred to me that there’s value in forming temporary alliances with fellow freelancers. Not only do you have a trusted partner with whom to brainstorm and collaborate, but you’re also able to up the project rate because you’re positioning yourself as a team instead of a solo person on a project.

V. I made my mental health a priority.

Cal Newport’s Digital Minimalism made a formidable imprint. I deleted all of the social media accounts that amplified my illness (or gave me a platform to rant incoherently about it). I excised all the human barnacles from my life — the people who are intent on sucking the breath right out of your mouth if you let them. And before you drop prized nuggets about how Medium is a social network, I’ve already addressed my view on Medium vs. the other platforms in this piece.

I’ve designed a schedule that allows for two hours a day free of screen time and stimuli so I can rest and recharge. I’m surgical about the people and clients I allow into my life. For me, self-care isn’t about lighting candles and spouting mantras, rather it’s about giving myself permission to refuse the things that bring me harm and unnecessary anguish.

VI. I write about what bolts me out of bed in the morning.

You can be conscious of your wants and tend to them without having them subsume your reason to be.

I write because I live to tell stories. And while I do consider the reader to a certain extent, I don’t write solely for them because that would be an impossible task and remove all the verve and passion from my work. I write about what moves me, and while that may appeal to some I’m not here to win the world over. If I wanted to write commercial fiction instead of strange novels, I would. If I wanted to write the things I know will get me traction, I would. You don’t like reading the long articles and essays I write? Then read someone else’s shorter work. There’s a difference between adapting to audience and trends and completely pandering to them.

Instead, I write to connect with others. I write to share what I’ve learned — whether that’s about writing and publishing or my work as a marketer and journey as a freelancer. And that sharing has resonated with the people with whom I want to work. People have hired me based on the work I’ve published on this platform.

Like networking, I don’t write with a transactional agenda.


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