In January 2020, I quit my full-time job at a software company to pursue my own IT content writing business. I decided to turn it into a case study to keep myself accountable and (hopefully) share some interesting and/or useful information with others who are thinking about starting businesses this year.


Why IT content writing? One of the things my wife and I really want to do more of is travelling (both domestically and internationally). For maximum flexibility, this necessitated me choosing an online-based business. I’ve always had a knack for grammar and spelling and had previously done some semi-profitable content writing back in early 2019. So content writing seemed like a good fit. However, I wanted to niche down to help make marketing easier. Since my background is largely in the IT realm, it made sense to choose IT content writing as my niche.


This isn’t my first rodeo. I started my first business (IT consulting) back in 2013 after being fired from my full-time medical transcription job at a prestigious hospital. Knowing what I do now, I probably could have successfully contested that firing and may have ended up going down a completely different path in life. But I digress.

Even though I’ve had a few “day jobs” since 2013, I’ve never really closed down my business. So going into this, I already had an LLC, business bank account, business credit card, domain name, etc.

A few things I learned from my old IT consulting business were:

  1. I have no desire to scale my business into a huge corporation with a bunch of employees, commercial office space, etc.
  2. “If you stand in the middle of the road, you get run over.” “Jack of all trades, master of none.” In other words, niching down (especially in any kind of creative field) is absolutely key to effectively marketing your business.

With all the above in mind, I set some ground rules for myself.


  1. Never do any work without a signed contract.
  2. Never do any free work (also known as “spec work”).
  3. Keep the business development/marketing process as systematic and “brain-dead” as possible.
  4. Exhaust any and all free means of marketing and finding work before resorting to paid avenues.


I’m not going to dive into my actual writing methodology as I don’t feel that would be helpful. Every writer I’ve ever met approaches things a bit differently depending upon what works best for them personally. It’s one of those things you just have to figure out on your own.

What I will shed some light on, though, is my business development/marketing methodology. Look, biz dev sucks. Sales sucks. Marketing sucks. It’s tedious work that no business owner really wants to do. But if you neglect it, you will fail. You have to keep work coming in consistently to keep the lights on. And the only way to do that is to market yourself consistently.

Notice I said consistently, not effectively. Don’t get me wrong. You absolutely want to market yourself effectively, but I’ve seen too many cases where people get so caught up on finding the “best” way to market themselves that they never actually get out there and market.

In my case, I treat my marketing efforts like I do my workouts. The important thing is that I’m consistently in the gym working out daily. Some days I’ll feel like I got a better workout than other days, but as long as I’m being consistent, those low energy days don’t hurt me as much.

I also want my marketing to take as little brain power as possible. The easier I can make it on myself, the more likely I’m making it that I’ll stay consistent with it every day. So for the time being, I’m not worried about using any crazy tools or complex automated workflows. Instead, I’m just using simple spreadsheets and mail merges to cold email potential clients.

In a nutshell, the process goes as follows:

  1. Create a spreadsheet for every major city in every state, and fill it with the information for the target companies (i.e., managed service providers) in that city that I can find within the first few pages of search results.
  2. Use the Mail Merge extension for Thunderbird (my personal email client of choice) to send a simple cold email out to those companies.
  3. Rinse and repeat from coast to coast.

The goal, of course, is to obtain as many direct clients as possible. This gives me the ability to control the relationship directly, gain testimonials and referrals and charge the most money. However, I realize that it will take time to cultivate direct relationships with lots of clients, and I have to keep the lights on in the meantime. Therefore, I’ll also be reaching out to marketing agencies with this same approach to see if any opportunities exist to sub under them. And finally, I’ll even be getting on some of the dreaded “content mill” sites so that I can fill my schedule with some crappy work from them if need be.

To supplement the cold email outreach, I also have a once-per-week task of posting to several relevant subreddits, checking the ProBlogger Jobs section, checking the LinkedIn Jobs section and checking ZipRecruiter. Finally, I have posts queued up for my LinkedIn profile and company page that go out a couple of times per day.


To date, I’ve reached out to managed service providers in every state from California east to Florida, and I’m working my way north up the East Coast. I’ve received a handful of responses from interested parties and secured one paying client.


So far, I’ve earned $180 from one contract.

My goal is to keep these updates coming once per day every weekday. Thanks for taking the time to read this, and I hope you have a nice day!