A writer's career and timeline

The joy of doing work you love.

Image created via Midjourney

Earlier this year, I watched Jonathan Groff accept his Tony Award for his role in the Broadway show Merrily We Roll Along. If you're not a musical theater junkie like me, you might know Groff from his role as the voice of Kristoff in Frozen, his role as Jesse St. James on Glee, and — my favorite — his role as King George in Hamilton. Anyway, he's an immensely talented actor, and during his acceptance speech, he recounted his lifelong love of theater. He said, "I'm now 39, and musical theater is still saving my soul." He also said:

I used to record the Tony Awards on a VHS tape and watch the performances over and over again. And to actually be able to be a part of making theater in this city and just as much, to be able to watch the work of this incredible community has been the greatest gift and pleasure of my life.

In a few weeks, I'll be 41. Like Groff, I've had a lifelong love of my craft, starting when I was very young. I wrote so much: stories, newsletters, and an endless stream of journals filled with a young girl's dreams.

It's been two years since I went out on my own as a freelance writer and four years since I quit my 15-year career at a tech company. It's kind of wild to me that people pay me to write things, and it sometimes feels weird that people I've never met read stuff I write on The Internet. Though that's the goal of a writer, right? To put words out into the world. I get to spend my days being a creative person.

October is a month of celebrations for me, so I wanted to take a moment (a few days early) to reflect on those.

Writing all the time

Yesterday, I recorded a podcast episode as a guest. The host asked me about my work and I talked about how I write for clients and also for myself (like this Substack).

On average, I write several long-form pieces per week between my blog, my other blog, this Substack, and my newsletter. In addition to writing for clients. Probably, on average, I write anywhere from 7,500 - 10,000 words per week, about half of it being for clients and the other half being my own writing.

If you're not in the writing world, a standard novel might be anywhere from 80,000 - 100,000 words. So, in the span of a few months, I'm writing as much as some people put into an entire book, though the medium is obviously different. Writing a 1,500-word blog post is nothing to me now, because I can sit down and structure it within a few hours. There's a more definitive beginning, middle, and end. Someday, I'd love to write a book, but I know that's an entirely different challenge because it's so long. It's drawing out a story for a completely different type of audience.

Still, in this season of life, I write so much. I have the energy to write on top of client work because I get to write about things I care about. This Substack was born in October 2021 after a post I wrote on LinkedIn about remote work went viral and hit almost 4 million views. It felt like people were itching to have open conversations about work, which was evident in more than 1,800 comments on the post.

A timeline

With the celebrations of October, it's also my birthday month. I'll be 41 this year. I've been working (full-time) since I was 22, so this is my 19th year of working. I've now spent almost four years in this "new career" after leaving my tech job. Almost 20% of my career has been spent in writing and writing-adjacent work.

To a large extent, this career still feels new, even though it's not new. I still feel like the new kid on the block, even though I've established a very successful freelance business and others look to me for advice. In fact, a fellow small business owner recently commented to me on Threads that she thought I'd been in the marketing industry much longer.

But I've also been building for this my whole life, even though I didn't know it. I was gathering expert knowledge. I was acquiring skills that would set me apart. I've been writing in my personal blog.

I started a blog when my oldest child was born back in 2009. I wrote fanatically. I saw other "mommy blogs" of that era take off and wished (at the time) that mine would do the same. But honestly, I didn't know what I was doing and didn't know that I had to market myself. People wouldn't just discover my blog on its own. And I don't know if that — long term — was the right type of content for me anyway. That blog has since been retired since I wanted to protect my kids' right to control their own narrative on The Internet as they got older.

My other blog was born in September 2015, mere days after my daughter, Nelle, was stillborn. That blog is now nine years old. Even though I don't write in it as frequently anymore, it still exists.

A career path

That brings me to today. I spend about half of my time writing for clients, and the other half is spent writing on these different platforms and creating social content. It's so skewed because client work is 98% of my income. But someday, I feel like writing about the things I love will pay off. It already has. Truly, I've been writing online since 2009. I didn't give up. Even though that blog never gained traction, I didn't stop. I felt like I had a story.

In 2020, when I knew I wanted to change careers, I took on freelance work for a content agency. I was paid $27 per 1,000 words. I trained myself to write 1,000 words in a little more than an hour so it wouldn't feel like a terrible rate. It was a content factory. I'd be in a very different place if I hadn't gotten a job that paid a decent salary to writers. At that rate, I would have needed to churn out so many words per day that my brain would have nothing left for my own work.

But instead, I got a job at a content agency. I left my corporate job. I took on a retainer at a magazine and a freelance client to offset the massive pay cut I took when I left my executive role. That was from early 2021 to October 2021. I didn't do much personal writing because I was so focused on my paying work.

Then, I took a job at an agency where I didn't have to write. I was the account director; I was supposed to manage client relationships and sales. In so many ways, that was the wrong job for me. Wrong company, wrong boss, wrong for my skillset. It all fell apart.

But the year I spent at that agency gave me time to think about what I really wanted to do. I started this Substack. I worked on building my online presence. Shortly after I lost my job at that agency, I started my newsletter.

When I left my first agency job, I thought, "I don't want to write for clients all day, every day." But that's not true. I like the client work I do now, because I get to draw on my expertise. I'm in control of the work and the outcomes. It doesn't feel like a chore. It's easy — for lack of better words. As a result, I have the time and mental bandwidth to do the work I love, which is all the other writing I do.

So here I am, 41 years old in a few weeks. Two years of working for myself. Three years into this Substack. Four years in this new career. Nine years into my blog. Fifteen years since I first started a blog.

When I look forward, I can't imagine anything else. I don't even think about the word "retirement" the way other people think about retirement. Maybe for me, retirement is just the freedom of writing without thinking about money. Not needing to trade my words for payment. But I don't look into the future and see this "cutoff" when I would stop writing.

It's immensely satisfying to get my work in front of people who care about it. Who read it and say, "I needed to hear this" or "This helped me in some way." Writers write so other people feel like they're not alone. That's certainly why I write.

"Choose a job you love, and you'll never work a day in your life," as the saying goes. I disagree. Finding and working a dream job isn't the only career-related measure we should be using.

Choose work that puts you in control of how you spend your time. Choose work that gives you the time and mental bandwidth to do things you love.

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