That time I did $150k worth of work for free

No, that’s not a typo. And I’m not exaggerating.

It was 2007. My marriage was unraveling and my days as a baby-wearing, attachment parenting, home-schooling stay-at-home parent were numbered.

I needed to find a way to support myself.

I had worked as a freelance copywriter until the day before my son was born. Wrapped a project, celebrated with a team lunch, and went home to wait for him to arrive.

I’d squirreled away enough money to take a 3-month, self-funded maternity leave. But just about the time when I would’ve had to go back, the Internet bubble burst. It was perfect timing. I didn’t want to leave my son, and now I didn’t have to.

And then, all of a sudden, I did.

So, I created a LinkedIn profile, contacted people I’d worked with, and haunted and craigslist. I’d only been off the treadmill for six years, but it felt like I’d been gone for a lifetime. Everything had changed.

Back in 2001, I was working 50-60 hour weeks and routinely turning down gigs that offered me twice my regular hourly rate. Now, nobody was hiring freelancers, and half my old copywriting colleagues had given up and taken “real jobs.” The other half was limping along, cobbling multiple 10- and 20-hour projects into a living wage.

And then, out of the blue, I got an email from a guy I’d worked with at the tail end of 2000. He’d hired me to create a library of personal finance materials for what was, at the time, the largest bank in Boston.

It was a dream project. The topics were fun: “Planning for Retirement” and “Buying Your First Home.” We had an unlimited budget, and I was able to hire two of my friends to write content with me. We worked remotely, but met once a week in Cambridge for lunch and progress reports. It was my first experience as a content strategist, and I loved it.

Having this guy contact me at the exact moment when I needed a job felt like a gift from the Universe. We met for coffee and he explained the project. He and a few buddies had developed a proprietary “thing” that allowed them to predict a particular kind of consumer behavior with 90% accuracy. They needed a web site, sales materials, and a blog. Did I want to take on all of the content and copywriting?

Of course, I said, “yes,” feeling a wave of relief wash over me as I envisioned a regular check coming in for the next few months. That, however, never happened. I got a check after my first invoice. But after the second and third ones went unpaid, I got a call from “Robert” instead.

Money was tight. The team was looking for some VC funding. Prospects were great, but it was going to take a little bit of time. “Robert” offered me a stake in the company in lieu of payment. He explained some very complicated plans that involved our start-up being acquired, and incremental payments, and possible government backing.

And just like Fox Mulder, I wanted to believe. I wanted to believe that this guy thought of me as a friend, not just a freelance contractor. That he cared about me as a person, since I’d cried in front of him more than once when he asked me how things were going. I wanted to believe that he wouldn’t knowingly scam me.

I worked without a paycheck for the next year and a half, draining my savings account to stay afloat. Fantasizing about being acquired and how maybe my tiny sliver of the company would equal enough money to pay the mortgage off entirely. Or maybe pay for the kids’ college.

Over the course of those 18 months, I steadily lost confidence in “Robert.” The focus of the company seemed to change on a whim. Maybe he’d made millions on other ventures, but it clearly wasn’t happening this time. Without that sense of hope and possibility, it became harder to feel enthusiastic about changing our strategy — and all of our written materials — yet again. Plus, the job was exhausting. I’d get calls at 6:00 in the morning, on weekends, and late at night.

So why did I do it for so long? That’s the $150k question, right?

I call it “Bad Boyfriend Syndrome.” As in, even a bad one is better than being alone. Fresh from a heartbreaking divorce, new to the workforce, I was the poster child for low self-esteem — personally and professionally. I was just glad that somebody wanted me.

And then one day, after a particularly contentious phone call, I was done. I told him that I couldn’t continue to work for free and he very politely wished me well. That was almost five years ago.

And here’s where it all gets weird. Because not two days after that phone call, I got an email from a woman who’d gotten my name from a friend who’d told her that I had a lot of healthcare writing experience. The woman was Mad*Pow’s Amy Cueva. We talked on the phone, I showed her some samples, and she hired me.

At the time, I’d worked on one healthcare project. Robert’s. But I had a solid portfolio of work to show for it, and it was enough to convince Amy to give me a shot. That has led to years of collaboration with dozens of smart, funny, inspiring Mad*Pow people doing work that actually improves lives. And when I added that work to my portfolio, it attracted other clients in the healthcare sphere.

I didn’t set out to find a niche for myself, but somehow it found me. It’s my bread and butter. And unlike the me of 2007, I know that I do it well. And that the folks who hire me are as lucky to have me as I am to have the work.

That time I did $150k worth of work for free? I wouldn’t be here without it, and here is an awesome place to be.

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