I have an acquaintance who recently reached out to talk about how they “might approach getting into freelance writing.”

This sort of request happens fairly frequently and I always oblige. I have to say though, my track record of selling freelance writing as a career is less than stellar. Maybe it’s my sales pitch.

Here’s what you need to do to be a successful freelance writer, like myself: 

Get a journalism degree – What many would-be freelance writers don’t understand is this: I actually, shockingly, TRAINED for this little career I have. It’s not the journalism career I thought I would have but I didn’t just start writing one day, either. I didn’t do something else first and then become a writer. I’ve been “honing my craft” for more than 30 years now.

I went to college for journalism, and took many, many classes on the basics of good writing and good interviewing. I took investigative journalism classes to learn how to crunch data (this was early Excel days) and find patterns that could lead to stories. I took classes in business journalism and learned how to read earning statements. I took classes in legal journalism so I could read legal documents and speak to attorneys without looking like a total idiot. I took classes in city zoning and planning so I could someday cover city council meetings and know what the hell was being discussed. I took journalism classes on critical thinking so I would be able to better detect when I was being sold a one-sided bill of goods and could then find other sources and ask questions in an interview that would (hopefully) allow both sides to be presented. I took journalism ethics classes to learn how to be a balanced, fair, non-biased writer who protected their sources, and worked hard to get the story right.

Work in journalism – I spent many years working very long hours for shockingly little money on various newspapers and in various positions. I started as an editorial assistant while in college, sorting faxes, emails, snail mail, phone calls, and wire reports for the real writers on the business desk. Once in a great while, I got to update and localize small wire stories (with no byline). I also pitched stories that I sometimes got to write and sometimes had to watch as they were assigned to other, more senior writers. But I loved the job. I felt like I had already landed my dream job – working on a daily newspaper.

From there, I started working on stories for our real estate section. It was the late 90s in Austin and the commercial and residential real estate markets were booming. I would write on real estate trends and projects, interviewing developers and real estate agents, city officials in charge of approving projects, and residents and business owners who would be impacted. I went on to an internship in Seattle, where my main job was hanging out in the garage of tech companies who had gone bust by this time (this was 2000-ish) and try to get the recently fired employees to talk to me on the record on one of the worst days of their lives. Then I returned to Austin and had a similar task (as I said, the era of the dot.com bust).

When tech advertising dried up and the one newspaper in town (my newspaper) started slashing jobs, I worked for a legislative tracking service as their full-time editor, cleaning up and shaping scribbled notes from various committee hearings to 1) make some sort of narrative and 2) show our clients that their lobbyists had actually showed up to the hearing and made their attempts to support or kill a bill. The hours were long and the pay was not great.

Finally, I graduated from college and moved to D.C. to spend three years writing about U.S. trade policy, even though, when I first started, I didn’t even know what the WTO was (guess I should have taken an economics course in college). It was an ass-kicking, humbling experience that eventually broke me on journalism. I think I was making like, $30,000 a year and working 70 hours a week in a high-cost of living city. The math was not mathing.

Jump ship to the “private” sector – Exhausted and tired of being broke, I went with the money. I started writing member communications for a large business advocacy association (read: lobbying group). This would be verboten for a journalist. You can never go back once you write for anyone you might have previously covered or included in a newspaper story. You are no longer an “unbiased” reporter.

But I made much more money for much fewer hours of work. It was quite a challenge to learn how to write persuasive advocacy content for a membership audience, especially in my case where I did not agree with what the bullshit the association was selling. I had to fake it for the paycheck, which I did. What I did not count on, and what had not been part of any newsroom I had ever worked in, was the internal office politics.

Get fired from your cushy job – One of the interesting things about working in the association world is the churn, most of which is motivated by office politics. You look at a big business association or lobbying outfit and you think, “Wow. What a unified, consistent front this group is for their membership. Everyone is singing from the same book.” Under that united-seeming front is a bunch of petty little egos jostling for just the slightest little edge over their co-workers and other departments.

In association communications, you’ll typically have divisions such as strategic communications, external communications, internal communications, digital communications, press relations, event and education communications, and executive communications (aka: speech writers) — all of whom are competing to have their messaging take priority. On top of that, other coalition groups and task forces within the association will have their own scrappy little communications divisions, who don’t want to share work or credit with the larger communications apparatus. The whole system is designed to engender competition and breed turf wards.

I (who worked in member/external communications) went to war with the head of our strategic communications. I won a few battles but ultimately lost the war. First, my boss fired (I still don’t know why. He actually did not go to war with the head of strat comm.). They found a replacement boss who I trained, and then I got fired. Shortly after that, the replacement boss got fired too.

Work your network – After you get fired, you’ve got to work your network. The one and only good thing about working for an association and all that churn is that there are former colleagues everywhere. They all move on to other associations, and there is no shortage of associations in D.C. So, in the beginning at least, I reached out and went to lunch with as many of those people as I could find. I have literally gotten all my work from former colleagues in the association world — even now, almost 10 years after I was fired.

Skip the networking events – I went to tons of networking events in my early freelancing years, but it felt like a waste of time. Everybody there was looking for work, not offering it. Over 10 years, I think I’ve only gotten one client out of a networking event.

Leave your morals at the door – Just as I sold out and gave up on what I considered the noble profession of newspaper reporter for the cushy life of an association writer, I have also had to take on jobs as a freelance writer that actually conflicted with my own personal (Austin-progressive-bordering-on-hippy) beliefs. I have worked with and for associations involved in industries that I consider pretty awful (Although, thankfully, not the gun lobby. I have to draw the line somewhere).

I’ve also worked with associations representing industries I would have thought were delightful and they turned out to be the most entitled, awful, impossible-to-please members.

At least in the beginning, you don’t really get to pick and choose. If you are very lucky and successful, one day in the future, you will be experienced and wanted enough to charge the gross industries more to help wash away the guilt of making them seem more palatable to the public.

Become smarter with money – Without a regular income (or retirement benefits), you have to become a very disciplined saver. I squirrel away money when it comes in because I don’t know when the work will dry up or your contact will move on (see: association churn). And, I’ve noticed, clients can be very slow to pay. It can take up to two months to get paid on something, so you need to have backup funds to pay your bills while you’re waiting for that check.

Also, I have to keep track of my time so I know how much to charge. I don’t always get it right (I usually underestimate how much time something will take), but I have gotten better at it over the years. I also have to stay on top of invoicing and payments, saving for retirement, paying my own quarterly taxes. Sitting down and writing is actually only a small part of my freelance writing business.

Have a supportive partner – I would have never been able to go freelance writing if I didn’t have a supportive life partner, and I mean supportive as in financially and emotionally. When I got fired, I had a severance and a bit of savings, but my first reaction was to start looking for a new job immediately. XFE convinced me to give freelancing a try, at least until my severance ran out. He also makes quite a bit more than I do, so we have never worried about my contribution to the bills, AND he has awesome health insurance which covers spousal equivalents (ie: me), so I never had to worry about health insurance. So, find yourself a financially secure, emotionally supportive partner if you want to get into freelance writing.

Don’t have children – Sorry, but it is just a fact. From a financial standpoint, not having children has given me the freedom to be a freelance writer and (potentially) make less income. And as most people learned during COVID, working from home when you have children is practically impossible. If you think freelance writing is just a fun side hustle where you can work from home and save money on childcare, think again. You have to be super-disciplined and treat it just like going into a real job with the added difficultly of constantly marketing yourself and looking for new work to keep the pipeline flowing.

Be prepared to become obsolete – On both a micro (ie: personal) and macro (ie: industry-wide) level. Literally, all these things have happened to me as a freelance writer:

• Your contact or source on a project could leave or be fired or go on maternity leave, and the new person who comes in has their own freelance writer friend they want to work with.
• The association you are working with could decide to restructure/reallocate funds/cut overhead costs, and you, as a freelancer, are the most expendable non-employee on the books.
• A client might hire someone in-house to do your job. Or, as one association contact once told me: “We’re all essentially writers here.” I had to bite my tongue hard on that.
• An association client may decide to automate their newsletter to a service like SmartBrief or move their membership magazine to online only or get rid of the membership magazine altogether.
• A marketing agency you were working with on a major campaign did not get its contract renewed so now you are off the project, too.
• A grassroots, lobbying project you were writing for (for months) finally gets approved or killed, and that’s the end of that project.
• A client decides that AI can get the job done for a lot cheaper.

On the other hand, new writing opportunities have arisen over the years that I could have never foreseen. I’m doing a lot of social media writing for one client, which is very challenging for someone as long-winded as myself (see: this post). A couple of other association clients are moving into podcasts, which have their own content needs both in pre- and post-production.

So that’s my quick and easy, step-by-step advice on how to become a successful freelance writer. Oh, you also need to be self-directed but also willing to take direction from a number of different stakeholders, be collaborative but also ok with working alone, be able to defend your worth and skills when potential clients balk at your rates, and project competence and confidence even when you have no idea what the hell is going to happen in your career from one day to the next.