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

I’m Having the BEST Year and This is How I Did It

Image by mohamed Hassan from Pixabay

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. Flexibility. My 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.

I use to call myself the “end-to-end marketer,” which meant that I knew how to manage a brand through a spectrum, or if you want to get real jargony about it, its “life cycle.” From building a brand’s core elements, story, and positioning to marketing brands and products to end consumers, I had a proven track record to back my fancy-pants claim. While my peers were talking about streamlining, specializing, and “niching,” I was walking around with a billboard proudly touting that I CAN DO IT ALL.

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.

One of the biggest challenges in my business is my inability to plan a pipeline. If you peeked in my window, you’d find me head down, working. When I’m in my zone, nothing else exists and the world shifts to the periphery. I ignore that important event I should be attending or that lucrative freelancing retreat. I know I should be meeting people for coffee dates, but ghosting in Los Angeles is a default setting so I keep telling myself why bother?

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.

Without dropping a pile of marketing terms like “customer journey” in your lap, know this — some fields of work take a longer lead time to close than others. For my strategy work, for which I sell for $20K+, the deal process is long and complicated. So I hedge that timeline with other streams that operate on a shorter timeframe. While my core business centers on market research, brand platform development, and audience segmentation studies (translation: big deliverables, more cash money, longer lead times), I hedge those projects with short-term writing gigs.
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.

I’ll be honest. I set the bar above the sky for myself and for anyone with whom I work. But I’ve written about the palpable loneliness freelancing can breed. However, I’ve partnered with smart, trusted peers where our competencies complement, not compete. Our loose partnerships are mutually beneficial — they get the benefit of my expertise and a broader portfolio offering and I get to work in the company of awesome people from whom I’m constantly learning. Also, I get to work with people who challenge me and are fun. Remember fun?!

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.

I have clinical depression, and even with all the therapy, meds, and self-care under the sun, I have days where the sun is an assault and moving from one room to another becomes a Herculean effort. Leaving my home is inconceivable. Paralyzing self-doubt is my default setting. While I can’t control when the fall and depth of these days, I can make the environment me manageable.

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.

It’s been interesting to see people who’ve been writing on Medium for a minute complain about Medium as if their $5 monthly membership fee should afford them trespass to instant stardom. As if they’re entitled to fame and a readership because they ask for it. As if the simple truth that the onus is on the writer to cultivate and retain a readership fails to register. I’ve been publishing online since 2001, and have written on Medium since 2013. Do I want people to read and share my work? Sure. Do I want people to buy my books? Of course.

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.

I’m an exceptional writer and marketer. I can say that with confidence because I’ve worked at both for decades and have personal growth and professional results to prove it. But I’ve learned that it takes more than being good at what you do to thrive in doing what you do. I publish. I talk to people. I take care of myself. I work on what challenges and nourishes me. And the acts that surround your work will reap a remarkable harvest. I’m having the best year of my career and while I believe that it’s okay to acknowledge when you need to make an exit, it’s also okay to try to make the thing you love work.

Subscribe to my newsletter!