Why I Freelance: Wealth and Status Weren’t Worth My Life

By Jessica Kirkwood February 6th, 2020

If we learned anything from California AB5, it’s that some policymakers view creative freelancing as a form of exploitation—rather than the career and lifestyle choice it often is. This is the first in a series of essays seeking to build understanding around why creatives freelance—and how the freedom to do so helps them live richer, more fulfilling lives. Pitch your story to trobinson@contently.com.

Some readers may find this account of mental health difficulties, including suicidal thoughts, disturbing. Click here to find a lighter read.


Imagine working 100-hour weeks just to keep up at work. That was me for the first five years of my marketing career in tech.

Sure, the all-nighters helped me gain more responsibility, climb the corporate ladder, boost my earnings and build credibility in my industry. But did the rewards make up for the sacrifices I made to get there?

Not even close.

Burning out at the peak of my marketing career

In March 2018, I joined a well-funded, high-growth tech startup as head of content marketing. I soon found myself working 100-hour weeks as a high bar for quality and a tendency to say “yes” rapidly broadened my role. Before long, I was leading organic marketing, pitching in with a corporate rebrand and overseeing a massive website migration—all while hiring a remote team of marketers to help me build a top-shelf content brand from the ground up.

I never saw most of that to fruition.

A few months in, I signed off to enjoy a pre-arranged vacation. My wife’s parents had come to visit from the Czech Republic, and we were excited to tour them around British Columbia for three weeks. But two weeks into the trip, exhaustion swept over me. I couldn’t get out of bed, let alone drive for 12 hours to the Rockies with my in-laws in tow. With my wife’s permission, I sent them on their way and spent the better part of the week catching up on sleep—unbeknownst to my colleagues.

Immediately before I was supposed to go back to work, my father’s heart went into overdrive. As a daddy’s girl, it shook me to my core. At 29, I wasn’t ready to start worrying about my parents’ health. I reached out to my CMO in tears to ask for some extra time off.

As the days passed, it became clear that one or even two weeks off wouldn’t cut it. I had been in denial: It wasn’t just my father who was having health issues. Years of being a workaholic, accompanied by chronic stress and anxiety, had worn me down. Not only had I gained weight and lost physical strength, I had been diagnosed with prediabetes and borderline hypertension. More importantly, I had neglected my mental health.

I was now exhibiting all the tell-tale signs of clinical burnout.

Waking up at the brink of death

I began to sleep 12 hours per night, supplemented by multiple two- to three-hour naps each day. When I was awake, I was practically catatonic. I struggled to concentrate for the first time in my life. I couldn’t retain short-term memories. Simple decisions were too hard to make. Sadly, I was also experiencing profound guilt over all my broken promises—to my team, my boss and, most importantly, my wife. I had failed everyone in my life, and I wasn’t sure I could recover.

I spent the next few months in a major depressive episode, living off of the money I had worked so hard to save. Believing things couldn’t get worse, I ate poorly and refused to leave the couch. I had zero interest in former hobbies, so I Netflixed (without chilling) and cried spontaneously, sometimes for hours. Perhaps worst of all, I walled off friends and colleagues, avoiding social media, email, texts and phone calls—ghosting those who cared about me most.

I knew I had reached rock bottom when I started to question whether I wanted to live. Soon after starting on a cocktail of antidepressants, I experienced a wave of what I can only describe as heightened disconnection: I no longer felt guilty about leaving the ones I loved, even if it was in a violent manner. I could do it if I really wanted to, I told myself.

That scared me enough to contact a professional.

Self care as salvation

Over the next few months, I met regularly with both a therapist and psychiatrist, who experimented with different medications until they found one that would help me feel stable and motivated. At the same time, I worked to create the conditions necessary for my recovery.

I started small by eating healthful foods, taking nature walks and going on low-key dates with my wife. Next, I signed up for a few courses at my local university with the intention of improving my health literacy. Soon, I was doing yoga and practicing meditation. Eventually, I even started to bake, draw and paint again.

The key to feeling balanced, I learned, was nurturing my mind and my body. Self-care would be my salvation.

As we rang in the new year, I reached out to Contently. I was ready to work again—but not full time. I was scared that I would violate my own boundaries if given the opportunity to work more than 20 hours per week, so I started taking on one client at a time in 10-hour monthly increments until I had a satisfying workload.

As I reflected on what had unfolded, I came to an important realization: The more I pushed myself to achieve wealth and status, the less happy and healthy I felt. Maybe the live-hard, die-fast life wasn’t for me. Maybe I wanted the work-life balance that freelancing provided to be my permanent reality.

Flexibility to support my mom through her cancer journey

Last Mother’s Day, my mom looked unwell during our visit. My wife and I had urged her to go to the emergency room, but she refused. The next morning, I woke up to an email from her saying she had finally taken our advice. Minutes later, my wife and I were on our way to join her at the hospital.

Near the end of her stay, the doctor sat us down. She explained that the CT scan they had done to rule out any serious issues had revealed an unusual shadow on her lung.

“It could be nothing,” she explained. “But let’s get it checked out.”

It was months before we had a decisive answer. A biopsy revealed in late July that my mother had a large, malignant tumor in her right lung, and a subsequent PET scan turned up cancerous growths in the lymph nodes surrounding both lungs. She had stage 3B lung cancer, an advanced diagnosis fewer than one in five survive.

Fortunately, my parents had recently moved just minutes away from both my apartment and the cancer agency. And as a freelancer, I could attend her weekly oncology appointments—and countless others, including hours-long chemotherapy and radiation treatments. I was even able to set aside time to help with weekly chores—the cleaning, grocery shopping and cooking that she and my dad, who at the time was suffering from pneumonia and recovering from hernia surgery, couldn’t manage on their own.

Had I still been working 100-hour weeks as a marketing director, none of that would have been possible—and I might have regretted it for the rest of my life.

Jes on her 30th birthday.

Looking forward to my future

Since going freelance, I’ve felt profoundly grateful. Not only have I been able to support my family while working fewer hours, but I’ve revitalized and rediscovered myself, rekindled my marriage, and even found time to be with my mom while she battles cancer.

I’m looking forward to using my free time and energy to raise my kids, rather than paying someone else to do it for me—a privilege most people wouldn’t dream of, let alone hope for.

If you or someone you know is considering suicide, call the National Suicide Prevention Lifeline, open 24/7.

Jes Kirkwood is a freelance writer, content strategist and managing editor at Contently, where she works with top business, technology, finance, insurance and healthcare companies. In her spare time, she’s passionate about helping others prioritize their health and happiness over wealth and status. Start a conversation with her on Twitter.

Considering going freelance? Register with Contently for the chance to work with top brands.

Photo Credit: retrorocket

Tags: , , , , , ,