Developers: David Colgan helps you escape 9-to-5 employment by building an effective freelance business you'll love to run.

Getting Clients is Pure Luck, So Let's Get Lucky!

Expanding your luck surface area to get freelance work


"How do I actually get clients?" This is the most frequent question I've been getting lately from freelancers-to-be.

It's all well and good to know how to use the tools of the trade, get good at your craft, configure your laptop, and develop your optimal productive routine, but none of that matters much if you can't get clients.

One strategy is to use freelance matchmaking services like Upwork.com. I personally am not a fan, and from what I've heard, neither is really anyone else who uses them.

All of my good remote freelance work as a Django/Python developer has come from "being lucky".

That is, I was in the right place at the right time and met the right people who needed the skills I had who then at some point hired me.

The more you put yourself out there, the more people you meet and the more opportunities you take advantage of, the larger your "luck surface area". Luck surface area is a measure of the serendipity in your life.

How I got every one of my recent freelance jobs

Let me illustrate with how I got all of my good recent gigs. Note how not one of them came directly!

  1. A person in my college graduating class gets a job and two years later contacts the computer science department and asks if they "know any freelancers." I had made it known to my professors that I was going into freelancing and they connected us. Client for 3+ years.

  2. I joined a coworking space and made friends with a guy. I mentioned that I do freelance work. We built rapport. 3 weeks later I'm siting at the tables there and he comes up to me and says, "I'm getting a full time job and can't keep my client. Do you want them?" Client for 3+ years.

  3. I was a teacher's assistant at a college class about software engineering. I made friends with a student. 3 years later his friend was graduating and was interested in freelance. The first student connected us. I offered to meet for coffee with the younger student, and told him everything I know about freelancing. 3 months later he contacts me and says "I decided not to freelance, but this client wants a website, do you want the work?" Primary client for the first half of 2018.

  4. I discovered a podcast by a thought leader in the consulting space about how to find a niche. I sent him an email saying, "Hey I liked your podcast. My niche is Django development." Later another person who does Django work contacted the podcast host. The podcast host shows this other person my website. This person joins my mailing list. I see that person has joined and so sent him an email saying "hello what up"? We connect over the fact that we both do Django freelancing. 3 months later he says "my primary client needs more help with a Django site." This is how I got my current primary client.

The big list of ways to increase your luck surface area!

So, how can we increase our luck surface area? I have seen people find success with all of these strategies:

Do Cold Outreach

This is probably my biggest level up as a self-employed human.

Did you know? You are allowed to send emails to cool/famous/important people and sometimes they respond! This was something I literally only really realized about a year ago.

Liked that article someone wrote? Send them an email thanking them.

Liked that podcast interview they did? Send an email telling them why you liked it.

Do you admire someone's work? Thank them for it.

Know two people who you think would benefit from knowing each other? Offer to connect them.

Don't try to sell them on things, just start a conversation. Ask about how they've been. Tell them what you've been up to. Ask them if they are dealing with anything in their business. We are humans after all. Humans like interacting with and doing business with other humans who are not always out to sell them something.

Go to meetups and talk to people

Go to meetups and talk to people. Don't try to sell yourself, just make connections. People will naturally ask what you do, so tell them you are a Python/Django/whatever developer.

If you are in a larger city, there is probably a meetup for every technology you can think of. I'm in Chicago and so have recently attended these meetups:

Speak at meetups

Speaking at meetups is even better than attending. Most meetup organizers would absolutely love for you to speak at their meetup as there's always a shortage of speakers. If you can present a good talk related to your area of expertise, you can gain "star power" in the eyes of the audience. You just proved you know what you are talking about by talking intelligently for 10/20/50 minutes.

You can usually give a brief shoutout to yourself when speaking. Again don't try to sell anything, just mention that you are a freelance developer and how to contact you. You just quickly and easily gave every person a reason to come up to you if they need your services or if they want to chat. This is very helpful for my socially anxious self, as then I don't have to be the one who initiates conversations.

Often you can ask to have the talk recorded, and then you've got a permanent way for people to find you online.

Participate in online communities

Two things you can do here:

  1. Just participate in the community and get to know people. Answer questions, ask questions, be a cool person. Don't explicitly try to sell, but make it known what you do. Have a profile that has a way to contact you and your website.

  2. Keep an eye out for explicit job postings. Many of these communities have "who's looking for a job" sections, or people may post a thread of "I need a developer who knows X technology. Anyone interested?"

Some examples of high quality free communities:

Hacker News

Hacker News is a tech news aggregation site with high quality technical discussions in the comments. It's run by the widely known Y Combinator venture capital group founded by Paul Graham. It gets a lot of traffic and very smart people read it. I've started a number of interesting relationships from Hacker News just by participating in discussions. Say something valuable that contributes to the discussion and make it easy to contact you from your profile.

If you make something interesting technically, you can create a "Show HN" post, which often are easier to get traction than posting an article link. Hacker News loves technically impressive things, though know they can also be fairly harsh in criticism. Make it easy to contact you, and remember that all publicity is good publicity.

In addition, every month there is a "Freelancer? Seeking Freelancer?" thread on the first of every month. Post your one paragraph pitch on there and get some nice exposure. If you can't find this month's post, they all have the same title plus the month and year. I ran this search to find all of them. from the search box at the very bottom of the front page.

Here is last month's thread: Ask HN: Freelancer? Seeking freelancer? (August 2018)

Regional and Specific Tech Slack communities

You may already be a part of a growing number of Slack groups. I know I'm in upwards of 10 currently! These can be a great place to hunt for gigs, as many larger cities will have a Slack dedicated to local tech. Many will have a #jobs channel or a #freelancing channel. In addition some larger cities will have Slacks for specific technologies.

Basically search for "<tech name> slack" or "<city name> tech slack" and you'll probably find something.

For example: I'm currently a member of these Slack channels:

Have an up to date LinkedIn profile

This is one I'm not as experience with, but I know many people who get work from LinkedIn. It's just one more way to find you online, and the more of those the better. If nothing else just put your experience and that you are looking for freelance work.

For added quality, try paid communities

I once talked to the founder of a paid online community, and he said that since they added the entry fee of some $200 a quarter, the number of trolls dropped to zero. I imagine nobody is going to pay that much money just to be a butt. I've heard of Founder Cafe and I'm a part of Freelance Camp.

Create open source software

I've heard of a number of developers getting work from creating a useful open source library and then helping clients in projects that use that library. Just make yourself easy to contact and put a note in the project readme. You may already have something you can open source fairly easily. Posting your library to Hacker News may be a good way to get some exposure.

Go to conferences

Especially if you enjoy meeting new people in person, conferences can be a great way to meet lots of new people. I went to Microconf the last two years in Las Vegas and have met dozens of people I still stay in touch with and refer around through it.

Technical conferences can be a great way to meet people inside of a tech ecosystem. Something I want to experiment with more is going to business conferences. If you are the only person at the conference who speaks code, you may be a hot commodity as compared to if you are one of hundreds of fellow developers.

Speak at conferences

This one takes a little bit of a build-up, but if you've successfully given talks at meetups, giving a talk at a conference can be a natural next step. Conference talks go out to everyone in the audience, and often go up on Youtube afterward giving you a perpetual boost to your luck surface area.

Now, follow up!

You've put yourself out there. You've met a lot of people. Now you need to follow up.

This is the most important part! Our goal here is to stay "top of mind" with as many people as possible. We do this by regularly staying in touch.

One of my all-time favorite articles on this subject is Derek Siver's article Stay in Touch With Hundreds of People.

In short, put everyone interesting you ever meet into a system and regularly send them emails asking how things are going.

We aren't going to explicitly sell anything even here. We will just ask them how things are going. Ask about details you remember them talking about the last time you met them. See if you can provide value somehow.

It will definitely help to use a tool to do this, as I seriously doubt you'll be able to keep track of this many people in your head.

There are hundreds of CRM (customer relationship management) tools you can use, from full-fledged apps like Pipedrive and ActiveCampaign to a simple Google spreadsheet or Trello board. Start out with whatever is the easiest for you to use. Set it up so that you reach out to each person in your CRM with some kind of regularity.

But David, I don't want to be a salesperson

Cool, neither do I! It seems to me that sales is "sleazy" when you are trying to take without giving, or trying to get people to buy something they don't ultimately need or want. I find it way easier to put myself out there when my primary goal is to provide value to others rather than suck everyone dry and take as much as I can.

I find it a lot more fun this way too.

As you might be able to guess, this generally doesn't work as a short term, gotta get work right right now strategy, but the difference in quality of clients is night and day. Provide value, make connections, increase luck surface area.

And don't feel like you have to do everything here

The nice part here is that you can just pick a few of these strategies. Are you more extroverted? Attend live in-person networking events. Are you more introverted? Do more cold outreach.

Good luck!


P.S. This is the earliest reference to "luck surface area" I can find:

www.codusoperandi.com/posts/increasing-your-luck-surface-area

P.P.S. Fun fact: all of these skills are really useful when building products, but without the added complication that building products bring. As such remote freelancing can be a great stepping stone to building products.


I first sent this article as a letter to my mailing list. New letters go out each week!

Learn to Freelance from
The Less Boring Letters

Learn freelancing from someone who's gone down this path before. In the the Less Boring Letters, I'll teach you everything I know about ditching the 9-to-5. Build a profitable new business that you love, benefitting from all of my trial and error.

"I send all my newsletters straight to an email box I almost never read... except David's! Insightful, honest, sometimes downright hilarious, and truly helpful even after years of freelancing."

Elise Fog
It Must Bee: Websites with a Buzz!