Ask a Freelancer

What I Learned From Writing 62 Advice Columns

By Nicole Dieker September 15th, 2015

On June 2, 2014, I pitched The Freelancer the idea of running a weekly advice column. Here’s the pitch in its entirety:

Once a week, I will answer real questions from real readers. Advice columns tend to be ridiculously popular anchor features for publications, and having a weekly advice column will drive reader contributions as well as get repeat visitors to the site.

But you don’t need me to tell you this. ; )

We’d probably need to seed the first column or two with internal questions and then wait for the reader questions to pour in. Or I could ask people on Tumblr to send me questions for the first few columns.

Other headline ideas:

Advice From A Freelancer: [Subtitle]

Ask a Freelancer: [Subtitle]

Ask a Full-Time Freelancer: [Subtitle]


Although The Freelancer had already reached out to me with an assignment, this was the first pitch I submitted to the editors. It’s funny to go back through my records and realize that I asked them, right out of the gate, for a weekly advice column—because it isn’t a tactic I would recommend to anyone else. If I were advising another freelancer, I’d suggest doing at least three months of consistently strong work before asking for a column.

But I took a chance on The Freelancer, and the editors took a chance on me. I got to write Ask A Freelancer for just over a year—62 articles, including this farewell column.

But, to borrow a cliche, all good things come to an end. My editors and I agreed it was time to say goodbye to Ask A Freelancer and start exploring new ideas. After 62 columns, we had covered a lot of advice, and over the final few months, many of the reader questions I received could be answered with a link to a previous Ask A Freelancer column.

I’ll still be writing for The Freelancer in the future, so keep an eye out for my byline. But before I pitch my next piece, there was one question I didn’t answer: “What do you do when one of your biggest freelancing assignments ends?”

The short answer is that you move on and pitch your next big assignment.

The long answer is that I started planning for the end of Ask A Freelancer in July since I predicted—correctly—that we would close out the column sometime in its second year. At that time, Ask A Freelancer brought in roughly 20 percent of my writing income, which meant I needed to find either one big client to fill that income gap, or a few smaller ones.

I made the process easier for myself by thinking of it as filling four separate financial chunks—one chunk for each week.

My Patreon took care of one chunk, and so far I’ve been able to reach out to other clients to fill the other three. By Spring 2015, I’d like to find one new client that can fully replace it.

In addition to the practical moves, I’m also spending time reflecting on how being an advice columnist impacted my career. One of the best ways to see exactly what I’ve learned is to go back and read some of the early columns. My first article, “How Do You Get Over the Fear of Asking People For Work,” was only 430 words long, not including the introduction. It took me—and my editor, Jordan Teicher—about a month to really figure out what this column was and what voice we wanted it to have.

I owe a huge debt of thanks to Jordan for helping me solidify that voice and a sense of purpose. I began the column with the idea that maybe I could become the next Heather Havrilesky or Cheryl Strayed, which is such an entry-level freelancer fantasy that, in retrospect, it seems hilarious. So, as I tried to figure out what kind of distinctive voice would catapult me into freelance fame, Jordan steered me towards straightforward, actionable advice—which was what this column needed.

Jordan will also remember how I used to push back against a majority of his edits. When you’re used to writing one-off pieces, it’s easy to get defensive about revisions and just move on to a different publication after a disagreement. But when it’s a long-term relationship, you learn that the process is about more than just your words; it’s about the publication and its style and its readers. You learn when to compromise and when to push back. For the most part, a good freelance assignment will feel like a collaboration.

I’ve also learned that trying to create a “distinctive voice” is generally a terrible idea. My voice, as a freelancer, developed its own distinct qualities over time based on the stories I wrote; I didn’t have to force it. That first Ask A Freelancer column fascinates me because I’m reading a much younger version of myself. I’ve written over 800,000 words since June 2014, and I’ve learned a lot from my editors. It makes sense that my writing has grown.

From a financial perspective, I’ve been tracking my freelancing income online for three years, so I can tell you exactly how my income has grown since I started writing this column. Although I had already established contributor relationships at sites like The Billfold and The Penny Hoarder when I started, I was also doing byline-free work for 4 or 5 cents a word, and I was still writing content for Crowdsource.

In June 2014, I billed $3,902 worth of freelancing work. Last month, I billed $6,513.

I now have a Freelancing A Team made up of regular contributing jobs at eight different publications, as well as a B Team I can pull from when I am in a temporary lull. I’m also incorporating crowdfunding into my long-term freelance strategy by inviting readers to support my serialized novel, The Biographies of Ordinary People, on Patreon.

In other words, I made sure to practice what I preached. I couldn’t advise someone else to regularly negotiate their rates if I wasn’t doing it myself. I couldn’t share that Ann Friedman quote about developing every idea into three different pitches without thinking about how I was going to develop my ideas into three different pitches.

I have always believed that what gets measured gets managed—which is why I originally started sharing my freelance income online, three years ago—and writing this weekly advice column was a way for me to both measure and manage myself against the advice I was giving other people.

I know I am earning more money now than I would have if I hadn’t written this column. I am also working smarter, procrastinating less, and avoiding long hours whenever possible. If I wasn’t doing something other freelancers were asking about, I did my research and tried to work it into my process. The very act of writing the column, week after week, taught me to be a better freelancer.

I hope it taught you how to be a better freelancer as well. In fact, I’d love for you to share your biggest takeaway from this column, either by emailing me at or sharing them on Twitter. (Please include @hellothefuture and @TheFreelancer so we see the tweet.) I’ve already received so much positive email from readers letting me know how the column has helped their career, so I’m glad to know that our work has done some good.

I’ve also received plenty of critical response from our readers, especially on topics like whether a freelancer should ever write a sample on spec, as well as what constitutes a fair freelance rate. Other readers have asked how I can possibly manage to write 20 short pieces a week, and whether my method of freelancing is sustainable.

I think we all have to figure out what is sustainable for our own careers. Right now writing a lot of short pieces, plus a few longer researched articles, feels like the right kind of workload for me. Over the next week, I’m going to be sending out a few pitches to bigger magazines and publications (the first one is already out, and I’ve got two more to send), and over the next year I hope to expand my portfolio to include at least one of these magazines.

I also want to work on landing more branded content gigs since I enjoy putting together sponsored copy and these gigs tend to be great for my bank account. (Yes, I’m a freelancer who is excited to write advertorial. Contact me.)

And finally, I want to build the audience for my novel. I’d love to finish the first draft and query publishers while including stats on how many people have already supported the work on Patreon. I’ve received strong feedback from my readers—and I’d like to share it with as many people as possible.

So that’s what you might see from me in the future. And who knows—I may end up writing another advice column someday! It’s been extremely fun to write Ask A Freelancer, and I’d love to address some of these freelancing questions again as I continue to evolve in my career.

I still have an inbox full of Ask A Freelancer questions, so if you’ve emailed me and I haven’t replied yet, I’ll be clearing out that inbox by emailing each person very quick advice over the next month or so.

To all my readers: Thank you. It has been a pleasure writing this column, and I hope you learned as much as I did.

Image by Kunal Mehta/Shutterstock
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