My advice to brand new freelance programmers and aspiring freelance programmers

As time goes on I find myself being asked with increasing frequency what advice I have for someone who’s just starting out as a freelance programmer. Here’s my advice.

Freelancing == marketing

My first piece of advice would be to make the realization that successful freelancing is all about marketing. The one skill that matters more than everything else is the skill of finding clients who are enjoyable to work with, who value the work you do, and can afford to pay well.

It’s pretty easy to find freelancing meetups or freelancing books that discuss things like taxes, accounting, contracts, etc. All that stuff matters but it matters way less than the ability to get good clients. Administrative work is pretty easy. The reward for doing it well is not that great. Marketing is super hard. The reward for doing successful marketing can be life-changing.

The key question to ask in freelancing is: how can I constantly be getting more leads for better, more lucrative clients?

Hunting and farming

There are different methods of acquiring clients. I put these methods into “hunting” and “farming” categories.

Hunting tactics include things like responding to job board ads, reaching out to people you know to see if they can help you find a gig, or going to a conference to try to find a new client. Like real hunting, hunting for clients can be fast, but it’s only successful a fraction of the time, and you don’t always get something good.

Farming tactics include things like writing blog posts, writing books, speaking at local meetups, speaking at conferences, guesting on podcasts, hosting podcasts, and other things that demonstrate your technical competence to a (if done successfully) large number of people. Farming can yield much better results than hunting, but there can be quite a long interval between the time you plant the seed and the time you get to reap the harvest. And just like in real farming, not all the seeds you plant will sprout into plants that bear fruit.

In my freelancing career I’ve kind of made a three-part transition from hunting to farming.

  1. Early on I got most of my gigs from job boards
  2. Later, as I developed a network of peers, I was able to rely more on referrals from past co-workers or “co-freelancers” (and by the way, these usually weren’t unsolicited referrals, but referrals I specifically asked for at times when I needed work)
  3. Later, as I got more into speaking and writing, there were a couple occasions when prospective clients came to me who I attracted via my speaking and writing, and these turned out to be the best clients of all

I strongly prefer “farming” methods. If I go knocking on someone’s door to ask them to hire me, the burden is on me to convince them why I’m worthy and why they should hire me. Plus, if I’m responding to a job ad, I’m typically competing with any number of other applicants to that gig. Conversely, if someone comes knocking on my door and they’re asking me if they can hire me, then the burden is on them to convince me why I should allow them to divert my attention from whatever work I was doing when they found me and work for them instead. It’s a MUCH stronger position to be in, and it typically results in much better fees.

When farming is impractical

If you’re just starting out freelancing and you want to get your first client ASAP, it probably doesn’t make much sense to focus on farming tactics to the exclusion of hunting. Luckily there’s no reason hunting and farming can’t be done in parallel.

I would suggest that the very first thing you do as a freelancer is plant a couple certain seeds:

  • Get a non-Gmail email account (e.g. jason@codewithjason.com)
  • At the same domain where your email is hosted (in my case codewithjason.com) put up a very minimal website – it almost doesn’t matter what’s on it because very few people will be visiting it anytime soon

What I would not advise is to fuck around with business cards, logos, business entities or any of that stuff. None of that stuff, not even having a business entity set up, is a prerequisite to getting your first client. Get your first client first, then deal with that stuff.

Then I would suggest hunting for your first client.

How to hunt for your first client

The people who are the most likely to agree to pay you money for programming now are the people who have paid you money for programming in the past. So my first move as a freelancer would be to go back to all my old employers and say, “Hey, I’m available for freelance work now. Want to work together again?” In fact, that’s exactly what I did when I first went freelance and it worked. It’s a super common thing for people to do when they start freelancing. A lot of times people even start freelancing by going to their current employer and pitching their employer to switch from an FTE relationship to a contract relationship. Sometimes it works.

Next I would reach out to some of my past co-workers and see who of those people I might want to reach out to about freelance work. I would start with the co-workers who I’d feel most comfortable asking about it and then gradually reach further out until there are no more past co-workers who I’d feel comfortable reaching out to. I would probably word my outreach something like, “Hey {{friend}}, I’ve decided to go out on my own as an independent contractor. I’m looking for my first client. Do you know anybody I should talk to?” Most of them won’t know anyone, and for any intros you are able to get through your past co-workers, most of them won’t pan out. This is just how it goes.

If I reached the end of my past employers and co-workers without landing my first freelance client (a distinct possibility!) then my next step would be to start hitting up the job boards. The job board I’ve used most successfully in the past for contract gigs is We Work Remotely, although I’ve had some success with craigslist as well. Sometimes the jobs I apply to are specifically contract jobs and sometimes not. I never shy from applying to a full-time job as a contractor unless it specifically says no contractors. I make sure to be upfront from the beginning that I’m looking for a contract relationship, too. No point in wasting either of our time if they’re not open to it.

The sales process

I see freelancers make a lot of mistakes around the sales process. Ironically, programmers tend to be hypersensitive to anything that appears “salesy” and programmers don’t want to be salesy themselves, but probably the most common mistake I see freelance programmers make is to try to sell themselves too hard too early.

Recently I introduced a friend of mine to a potential prospect via email. He committed the classic mistake of emailing his whole life story to the client including a list of past accomplishments. Dude, they were already sold on talking to you. Just give them your phone number and say give me a call.

The job of an email isn’t to sell the prospect on hiring you for the project. The job of an email is to sell the prospect on getting on a call. The job of the call is to sell the prospect on having another call. Then, maybe, the job of that call is to sell the client of hiring you for a project.

And when I say “sell the prospect on…” I’m really not talking about pitching or persuading. All the sales process is is an honest attempt to answer the question: “Are we a good fit to work together?” If so, then not much persuading is necessary. What is necessary is a certain amount of trust-building. Trust-building can be built a few certain ways. Some simple psychological triggers like hearing someone’s voice and seeing their face are ways to build trust. The more times someone has the opportunity to hear your voice and see your face, and the longer period of time over which that happens, the more they’re likely to trust you. Spending time in person also builds trust a lot faster than just interacting online. That’s part of the reason it’s so much easier to get someone to hire you if have an IRL relationship with that person prior to a discussion about working together.

Another way to build trust is by having strong marketing, strong authority pieces that signal to the client that you know what you’re doing without you having to make a single claim yourself about your own abilities. This brings me to my advice on what marketing activities you should engage in (since again, freelancing is all about marketing) after you get your first freelance client.

Seeds to plant after you get your first client

After you get client #1, I would suggest that you spend all your working time outside of working for client #1 on the job of securing client #2.

If you have a client who’s paying the bills, you can afford the luxury of the slow tactic of farming. Like I said earlier, the farming tactics that will attract clients are speaking and writing. What if you don’t like speaking or writing? Then you can’t farm, and you’re at a huge disadvantage. But hopefully you either already enjoy speaking and writing well enough or you’re willing to take your freelancing career sufficiently seriously that you’re willing to get past the fact that you don’t enjoy speaking or writing and do them anyway. Even just doing one is better than doing neither. I personally enjoy writing and feel like I’m pretty good at it. I am NOT good at speaking and I loathe the sound of my own voice most of the time and I’m embarrassed by 80% of the things I say, but I do it anyway because my desire to be successful is stronger than my distaste for speaking.

In your farming activities you can select from a menu of options:

  • Writing blog posts
  • Writing books (self-published or traditionally published)
  • Developing courses
  • Speaking at local user groups
  • Speaking at small regional conferences
  • Speaking at big national conferences
  • Guesting on or hosting podcast

I myself have done every one of the above items. If I hadn’t done any of these things before and I were just starting out, I’d probably start out with writing blog posts and speaking at local user groups, and in fact that’s exactly how I did start out. These activities are relatively low on the ROI scale but they’re also relatively low on the time/effort/expense scale.

Blogging is most successful when it’s done around a specific topic. For example, I currently mostly write about Ruby on Rails testing. (I also have a podcast and give talks on the same topic.) Deciding on a technical focus can be a little bit tricky. I arrived at the focus of Rails testing as a result of enrolling in 30×500, a class that teaches entrepreneurship skills to developers.

For more help

There’s probably a whole bunch of important stuff I’m leaving out. If you’d like to learn more about how to be a freelance programmer, you can my other posts and/or join my freelancer Slack.

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