Indie Pentathlon

Learn to Build Your Services Pipeline

If you're up for it, try this short exercise.
It might scare the crap out of you:

  1. Get a sheet of blank paper. Draw a line vertically down the middle of the sheet.
  2. On the left side of the line, list every project that's come your way based on a pre-existing relationship. Use shorthand notation to keep it compact. Your list should include projects that came from:
    • People you used to work with before you went solo
    • People who you knew before you started working for yourself
    • People you met after you started working for yourself but you met outside the context of your business. Referrals count too. Business that comes from family, friends, and friends of friends/family count too.
  3. In big letters at the top of the left side list, write ACCIDENTAL BUSINESS.
  4. On the right side of the line, list every project that's happened because someone:
    • Filled out a form on your website
    • Responded to an ad you paid for
    • Responded to cold outreach
    • Read your writing or heard you speaking (in a marketing context)
    • Met you because you specifically reached out to them
    • Sought you out based on the strength of your positioning, focus, or reputation.
  5. In big letters at the top of the right side list, write BUSINESS I CREATED ON PURPOSE (CAUSE I'M A BALLER).

What does the balance between the left and right sides of your sheet of paper look like? Most importantly, are you comfortable with that balance?

If you're not, then Indie Pentathlon will help you learn how to change that.

Indie Pentathlon is a completely free, 5-part, self-paced program with 1 goal: help you learn how to generate demand for your services so you can stop relying 100% on luck and accidental relationships to keep your freelance services business going.

Ready to try it?

Again, it's completely free.

The best way to discover if it's right for you is to sign up below.

You'll get set up with a login to the learning platform where Indie Pentathlon happens. Waiting inside are short self-paced audio lessons, tips, examples, and troubleshooting help.

If you need more support than the learning platform provides, I'll tell you how to sign up for a paid online coaching & accountability group or individual coaching with me. Some of you will execute the challenges on your own, others will be happy to pay for extra support. It's a choose your own adventure thing.

You can start the first challenge right away:

Sounds interesting, but a bit more detail would be nice.

I hear you. Let's start with what the 5 challenges are:

  1. Find a compelling advantage
  2. Find an overlapping market opportunity
  3. Build a gift of free knowledge
  4. Find 10 willing recipients for your gift
  5. Become a source of advice for at least 1 gift recipient

Seems pretty simple, right? And it is simple.

But if you look at that list and say "pshaw... I can do that in my sleep", then I would have to ask you: are you conflating simple and easy?

Because these challenges are not easy.

There are lots of "get more clients" courses out there. What's different about this one?

First difference:

This is experiential learning. Each of the 5 challenges tells you what to do, and gives you some general suggestions about how to do it, but that's it.

Rather than give you a (potentially outdated) "recipe" like a lot of online courses do, Indie Pentathlon gives you a framework that orients you just enough so that you can learn by doing.

Indie Pentathlon doesn't feed you; it teaches you to fish. And it teaches you to fish in a way that's unique to you and therefore will be more useful and powerful for your business.

Second difference:

You'll get to experience what it's like to specialize. Some "get more clients" courses skip this part, which relegates you to harvesting only low-hanging fruit. You've probably harvested all that fruit and now you're ready to learn a more effective way to find clients--or even better--build a way for them to find you.

Should I join Indie Pentathlon or The Expertise Incubator?

Think about it this way:

I'm here to accelerate your success by helping you build an expertise asset. If you already know roughly what that expertise asset will look like and precisely who will benefit from it the most, then join The Expertise Incubator ( If you don't know what that expertise asset looks like and/or you don't know who it's ideal for, then join Indie Pentathlon.

What are these resources you keep talking about?

These resources are also embedded in the Indie Pentathlon learning platform, but there they are organized by which challenge they relate to. There's no reason to lock them behind a registerwall, even a free one, so here they are, organized by media type:

Dev Shop Marketing Briefings

If you want to build a robust pipeline of work for your custom software development business, you will find my Dev Shop Marketing Briefings very valuable. I or a guest expert will spend 30 minutes teaching you how to market your services better and 60 minutes answering your questions.

The Positioning Manual for Technical Firms

Narrowing your marketing focus to a single, highly-profitable niche is the most valuable improvement you can make to your software development business. Actually pulling this off is not easy. You will face strategy, research, and emotional challenges. The Positioning Manual will help you succeed.


Many lead generation techniques do nothing to build trust. Paid advertising is an example of this. My Trust Velocity research profiles 46 lead generation techniques by how much trust they build, how quickly, and how suitable they are for generating high quality leads rapidly.


Identifying and dominating a desirable market position is the cornerstone of a profitable, in-demand services business. This process is often a high-stakes, low-certainty exercise in fear and frustration. My free Positioning Crash Course helps you cut through these roadblocks.


Most web design patterns emphasize ease of scanning content or following hot trends (parallax, anyone?), but fail completely at generating leads. Grab a free copy of this Lead Generating Website Template to avoid staring at a blank text editor only to produce yet another crappy "me too" website. MOAR leads!


See how others have specialized their business.


How do coders become consultants? They specialize, develop a point of view, and market based on their ability to move the needle for clients. This podcast explores the transition from coder to consultant through interviews with those making and enjoying the results of this transition, and occasional audio essays from your host Philip Morgan.