In 2017 I created a set of videos and posts designed to help solopreneurs launch their business. I've gone through this process 4 times now and each time I've learned something new... and relearned something old (aka "the hard way").

You can learn from my mistakes in this playlist! Good luck.


Let's kick things off by getting our heads in the right place and understanding what we're getting ourselves into. This could be a life-changing moment for you and having a plan is essential! So let's take a minute and wrap our heads around this.

You might want to go out on your own but there are some stresses involved. Let's take a second to be sure that this is the thing we want to do.

Is The Contract Programmer Thing Right For You?
Going out on your own is, essentially, turning up the volume on your career. The good parts get better: freedom to choose what you do and when you do it. The bad parts get worse: you will be the worst boss you’ve ever had, and a simple mistake can greatly affect your income.

Getting Organized

If you fly by the seat of your pants you run the risk of letting someone down and losing money, so let's take a second and see some extremely simple ways to get organized.

Let's take a look at two very useful and FREE tools that can help you with this. You should be looking at them every day when it comes to client work, and when you have meetings, instead of popping things in your reminders or sending yourself an email, use these CRM tools to help you out!


Here's your task: head over to my personal favorite list thingy, Trello, and have a look at their CRM (customer relationship manager) templates. Some of the automations require an upgraded account, which is pretty cheap, but most of the stuff is free.


Trello is super easy to use and has a desktop and phone app that you can use to organize things when you're on a lunch break. If inspiration hits, pop a card in there!

You'll be able to track who you talked to when and about what. When a project is kicked off, create a board for it and invite your client to join the board so they can see what you're doing - it's a great all around tool.


Some people (like me) just dig their spreadsheets and if you're that person too, than Airtable can be your new best friend. They have a set of amazing CRM templates that function as simple spreadsheets. I haven't used these yet (I'm a Trello fan) but I use Airtable for a ton of other things, including tracking billing and expenses, and I absolutely love it.

Just... Go. Do It.

Don't overthink it... just go and set one of these things up before you forget and add it to your backlog pile. You'll see and hear me say this often: don't think about it too much otherwise you'll get paralyzed. Execution is the Big Thing when it comes to doing something like this and the more you can tangibly see, the more motivated you get!

Your Business Plan

Yay lots of administrative stuff! This one should be quick, however... should be. You now get to think through exactly what you want to do with your business.

Creating a Solo Contractor Business Plan
We can ponder about our business plan all day long - let’s not. Let’s execute by laying something down right now, and building on it. You’ve learned what’s in a business plan, now let’s put something - ANYTHING in writing and commit ourselves to this vision.

Your Marketing Plan

Here's the simple truth: if you're not willing to spend time on marketing, just stop now. I need to be right up front with you on this: you can't make money unless you tell people you can work for that money.

The reason this is so painful is that it just sucks to go to Thought Leader's website and be subjected to a zillion popups with pictures of them everywhere, crossing their arms in the "proud of myself" stance. Barf!

But listen: you don't need to do that. You just need to figure out how you're going to tell people about what you do so that your sould doesn't whither away. I mean... if you want to put pictures of yourself on your website crossing your arms... go for it. The people that do that kind of thing do it because it works. They hate stupid pop up menus too! But they get customers...


The first thing we need to do is to identify who your market is. For instance: I wrote a book about Computer Science principles but for people without Computer Science degrees. That's a pretty well-defined niche and a very well-defined market.
I like writing and I like trying to take complex things and see if I can explain them in a straightforward way. If you put those two things together, I have identified my market and also my outreach.

As hard as it might sound, think about what you're good at. When I started out on my own, I knew I was good at three things:

  • Web sites, specifically with ASP Classic. I had run a business for years and knew the web well.
  • Databases. I spent years running a massive database for an environmental company and then scheming them out for my tech clients.
  • Product development. Clients liked to talk with me about whacky ideas, and in fact I was told more than once that my "weird, off the wall nonsense" helped shape my client's products.

That's the what. Now to the who. 90% of the people I worked with previously were Fortune 500 companies: big telecoms, Silicon Valley giants including Google and PayPal. I felt comfortable in that world, so it's natural that I should target those people as my market.

Do What You Know

So many people I know have decided to "make a fresh break" and start again by going out on their own. I did this once and it was a disaster! When Ruby on Rails came out I decided I wanted to be a Ruby person, so told my friends I was looking for a Ruby job - specifically Ruby on Rails.

I finally got a call from an acquantance and long story short: it was a total disaster. I didn't understand the world I was entering (mobile startup) and also what they expected of me. I knew Rails pretty well, but not the point I should have - so let's just say that's the last time I did that.

A month later I returned to what I knew how to do: enterprise development using .NET. I ended up getting a contract with the largest payment gateway in the .NET space, designing and building their .NET SDK. It was very good money and I executed happily, which helped me slowly change my focus over time.

If you want out of what you're doing now, you have to have expertise in where you want to go. Otherwise your increased risk of failure will blow this whole thing up!

Word of Mouth

It's always going to be your best bet. So right now I want you to pop open your Trello board (or Airtable or whatever you decided to use) and write down the names of some people you can call. These are potential leads and you need to create cards to help you:

  1. Remember to call them
  2. Track what was said during the call (or email/text) and then "score" the lead in terms of a getting work
  3. Remember to thank them later on

These people can be friends, old bosses, family (if you're OK with that) and people you might meet at a conference or event of some kind.
I know... random strangers? Really? Well..

Networking and Events

If you don't go to any meetups you need to start now, if only to get yourself out there to see what other people are up to and how they market themselves. You can find these things anywhere, but heading over to is your best bet. Find an event that suits you and just drop in to say hello.

Everyone is there to network, and that's what you're trying to do. So write down a few meetups in your marketing plan, and include them in your overall market approach in terms of defining your niche.

For instance: do you find yourself wanting to go to the MongoDB meetups more than anything else? Great! There's a possible market for you.

Just start writing... make stuff up if you have to. The point is that words, when they flow, tend to stitch themselves together. You just have to start with the first sentence...

I love doing X and it would be a dream if I could do it for Y...

Setting Up Your Services

You'll need them! An accountant, lawyer, and others. This might seem completely overwhelming but it's easy! It just takes a few minutes.

Setting Up Professional Services for Your Contracting Gig
Trying to run a business on your own is a sure way to burn yourself out. You have to delegate certain duties to online services and third parties. It might seem like an expensive thing to do, but it’s really not.
Setting Up Your Finances as a Solo Contractor
In this section we turn our attention to your new company’s finances. It may seem intimidating, but tracking your income and expenses can be quite easy with simple to use online services.

Growing Your Business

Now that all the machinery is in place and we have a plan, let's get to work! We'll need to find that work though - that's what these videos are all about.

Growing Your Professional Network
In this video we’ll look at ways to find your most important client: the very first one! We’ll get out and meet other developers, creating a legitimate network of peers. Finally, the best work is repeat work, so we’ll look at things you can do to make sure you are your client’s go to person.
Branding Your Solo Contracting Business
You need to stand out and make your virtual self look sharp and competent. This isn’t about physical looks, it’s about how you present yourself to others and the care you take in making an impression. These things matter a lot and they don’t take a whole lot of effort.

Now Go!

Thanks so much for watching this playlist and I sincerely hope it will help you in your future endeavors. I know you've heard me say it so many times (and read it too), but your dedication, discipline and ability to execute will make all the difference.

Three Things to Remember

You will be discouraged and, probably sooner than later, you will also feel defeated before you even start. This is natural and expected, it's also very human. We can dream the wonderful dreams but when it comes to putting transitioning those dreams into something real it can be terrifying.

But! There is a cure for that feeling of defeat! Can you guess what it is..? It's broken record time... but the best way to get over your self-doubt is by doing something. Even the smallest step forward is self-propelling.

For instance: right now you might be making lists and taking notes but you haven't actually done anything substantive. Let's change that! Seriously, right this very second.

Getting Off the Ground

Let's say you might have jotted some notes for a business plan, signed up for a few services and looked online for an accountant and/or lawyer. These are great plans - but they don't amount to executing your vision, so are a few things I want you to do for a first, substantive step.

Register Your Domain

If you haven't picked a domain yet, do it right now. Here's the link in case you forgot. Set a timer and pick something in the next 5 minutes. GO.

Once you've done that, sign up at Cloudflare and have them serve your site for you. You'll get a free SSL certificate which is rad.

Setup Your Site

Now, let's choose a platform for your site. Let's keep you focused - pick one of these:

  • Squarespace. It looks nice and keeps things simple.
  • WordPress. This is what I use (the OpenLiteSpeed version) for my front-facing stuff. This is a great option as you can use some outstanding marketing tools like Thrive Architect to help you grow your online presence. Let's not get ahead of ourselves, however. WordPress is a great pick just to get off the ground.
  • GitHub Pages. This is a good option if you like playing with HTML and want things for free (which is good)

Pay for Your Services

I have a simple bit of advice for you on this: DO. NOT. OBSESS. ON. FREE.. This is your business and your focus needs to be on getting paying customers to see you and call you. Do not develop a habit of freaking out over $30/month for a service that can bring in thousands. This is easy to do, especially in the beginning.

Can't Decide? Do This.

Once you've decided on your domain and registered it with Cloudflare, click that link above for the WordPress site and create a $20 image at DigitalOcean. Once that's done and you're into your site, install these plugins:

  • Thrive Architect. It's $67 but it will transform the way you think about your site, I promise. You may eventually want to get a Thrive Membership as their themes and marketing stuff is amazing - but for right now let's get you going.
  • WordFence. Search for it in the plugins directory. People suck and WordFence is a great way to keep them from hacking your site.
  • The Astra Theme. It's free and comes with some starter templates.

Once your site is up, we need a few pages. Things like the services you want to provide, more about you, your resume and your blog where you're going to post professional superstar stuff later on.

This can be super hard to conceive, so click this link and go get started.

Enough Reading! Go!

You can do this. I swear you can. I don't know you personally but I know that our industry needs really good people and if you're watching this you're one of those people.

Only you can make this happen for yourself. Put another way: you are your biggest problem! But I just said you're awesome so get over yourself and get to work!

Good luck!