Freelance Developer Coach

TL;DR: I’ve launched a new company called Freelance Developer Coach ( and we’re releasing our first product November 1st of this year.

The longer version is that I’ve done a lot of startup work over the years, but never something that was completely mine.  Last month I started designing a new company with what I considered to be an ideal business model.  I wanted something I could build and scale on my own where every piece would be automated so I could build once and sell thousands of times.  I knew that I wanted to create something which helps people and doesn’t steal time from their lives with no return in the real world (I’m looking at you Fortnite!).

I was fortunate enough to listen to a Tim Ferris podcast on a long drive where he mentioned some of his principles from The 4-Hour Workweek. One of his recommendations was to ask yourself, “What’s easy for you, but hard for others?”.  I immediately thought about hiring and managing freelance developers.  I’ve spent the last 6 years very focused on hiring and managing freelance developers for various companies and projects.  At first, I thought about creating something for hiring managers like me to manage this process.  Then it occurred to me that my greatest satisfaction came from coaching developers on the non-technical skills and habits which made them easier to work with – and more valuable.  After all, that’s what I’ve spent years writing about here.

After that drive, I returned home and sketched out the application and the business.  I had recently read Disciplined Entrepreneurship after a hearing it mentioned by a guy I really respect so I worked through the 24 steps and made sure I had answers for the 21 which applied to my idea (the other 3 are more for enterprise software).  That weekend I outlined a couple of ebooks related to the idea, set up some landing pages, and ran Google Ads.  My theory was that if people are interested in the ebook, then they’ll probably be interested in the software.  More importantly, if they aren’t interested in the ebook then I need to rethink the messaging, the market, or both.  So I launched my ads late Saturday evening to see what I could find.

I woke up Sunday to leads –  hundreds of people had clicked through my ad and dozens had provided their email address to get the ebook.

At that point, I knew that I could reach my market with a message they were interested in.  Since that was the critical first step, I started planning out the rest and after I completed the financial model I was pretty sure that I was on to something.  So now I’m back on familiar ground: building mode.  The first release is planned for November 1st, with follow-on releases every 30 – 60 days after that as long as the market continues to indicate interest.

I’ll post updates here at Big Swinging Developer, but there probably won’t be anything until after launch – focus and execution are top priorities until then.

How to Level-Up With 1 Simple Capability

Yesterday I wrote about assets and capabilities and while I gave some examples I left off the one capability which has allowed me to consistently level-up over time: figuring out what people want.

Often this is as easy as just asking.  Other times it requires some deeper thought to analyze the available info, the options, and extrapolate potential outcomes.  This is the skill portion, but that’s not enough – you need to put it into action for it to turn into value.  That’s really what this post is about and where the “simple” part comes in.

Make a list of everyone you affect – direct reports, managers, peers, clients, even personal relationships if you like.  Next, put down what each of those people want – specifically from you, but feel free to think more generally for extra credit.  For example, your direct reports usually want things like a clear definition of success, feedback on what they’re doing, interesting work, money, and any number of other things like training, software, hardware, and dozens more.  Your manager wants to know how things are going and that the next milestone will be hit successfully – perhaps another thing or two.  Once you have the basics, you can drill into detail for the particular projects you’re working on.

This list is dynamic and needs to be updated frequently.  For people you manage, this might be daily as you look at specific tasks.  For your manager, weekly should do it.  As you get further out to clients, then monthly may be enough.

This should be a simple exercise – given a person you affect, write down what you know about what they want.  If you are unsure, then the next step is fill it in.

Once you know what people want, you have your playbook and it’s time to start providing it.

For a direct report, maybe they want to work with a new technology and you find budget to provide training.

For a manager, maybe it’s time to update the project plan or to start looking at the next release – before being asked.

For a client, are they struggling with something which keeps them from using what you typically offer them?  If so, that’s a prime opportunity to provide assistance above and beyond your typical offering.

While this entire process really is simple, it’s not easy – especially in the beginning.  You’ll feel like you don’t know what people want or you may even doubt your analysis.  That’s natural and don’t focus on it too much and instead work to validate your assumptions.  Also, the more you practice this the easier it is to identify opportunities to give people what they want as you’re talking to them.  You’ll start to make mental updates to your list (which can be turned into actual updates once the discussion is complete) and you can adjust what you provide accordingly.

Lastly, what do you want?  How can you make it easy for those who affect you to know that and provide it?  It works both ways, but it starts with you.

Assets and Capabilities

Several years ago I developed a personal career strategy that I call The Assets and Capabilities Model.  For the purposes of this model, an asset is something which you control and a capability is something which you can get done.  Notice that this is different than “things you own” and “skills” – that’s intentional and to clarify, here are some examples before moving on:

Some of my assets:

  • My AWS account
  • My company’s reputation on Upwork
  • My computers (note that some assets are, actually, “things you own”)
  • Software I’ve purchased
  • My blog
  • My Zoom account (previously my WebEx account)
  • My relationship with my kick-ass designer in Ukraine
  • etc.

Some of my capabilities:

  • I can design large-scale distributed systems
  • I can implement a business or development process, train people on it, and monitor it instantly
  • I can perform code analysis and technical due diligence (in part because of experience and in part because of some of the software I own)
  • I can build remote teams quickly
  • I can schedule an online meeting at the drop of a hat
  • etc.

Take notice of some of the overlap – I can build remote teams quickly in part due to my experience and my company’s reputation on Upwork.  I can schedule an online meeting at the drop of a hat because of my Zoom account and because I’ve done it many times before.  I have long lists of assets and capabilities which took years of conscious effort to develop and several times a year I ask myself a few questions:

  1. What assets aren’t being fully capitalized upon? (I’m looking at you, list of domain names)
  2. What capabilities aren’t being used frequently enough?
  3. What are some assets I can acquire/develop?
  4. What are some assets I can divest? (domain names, old computer gear, and books are common)
  5. What are some capabilities I’m missing?
  6. What are some capabilities which need to be improved or refreshed?

I recommend the exercise to anyone who is interested in actively managing their value – pretty much anyone who isn’t retired.  The exercise starts simply enough: grab your note-taking tool of choice (I have a thing for Canson Sketch Pads) and start listing things you have/control which can be used to solve problems and things that you can get done, either yourself or via your network of strong relationships.  I find it’s helpful to link things together to find self-reinforcing constellations of value – things like AWS, Upwork, large-scale system design, building remote teams, and development process implementation all fit together to form a higher-level capability of “I can start a software company in an hour with nothing but an idea, a credit card, and an internet connection”.  As you perform your asset and capability cataloging exercise, you’ll naturally identify some of these higher-level capabilities yourself.  After you do, then you can follow on with questions about how to make that capability stronger, how to capitalize on it, etc.

What’s the point of doing all of this?  Right now you’re probably sitting on a gold mine of value, but it’s not being actively managed.  Once you have your catalog, you’ll see what you need to read, what kind of training you should seek out, which things you need to practice, and gaps which need to be filled – this is internal management.  Next, your eyes will be opened to opportunities.  You’ll find yourself coming across people who need something that you can can do or a chance to deploy an asset – this is external management.

As a final example, I remember some time around the end of 2009 I decided that I lacked public speaking experience.  I had no problem speaking to groups in meetings, but I had very little experience presenting to an audience who was there specifically to listen to me.  I developed an idea for a talk about the future of work and how it affected recruiter, contacted a few recruiters, and said, “I have this talk and I’m trying to get better at speaking – may I present to your team sometime in the next month?” Not everyone responded, but a couple did and I got to practice.  Public speaking is now on my list of capabilities because I’ve actually done it and so I know I can do it again.

What’s on your list?  What are you missing? How are you going to capitalize on the unique collection of assets and capabilities that you possess?


I love to read and have a rule that whenever someone recommends a book, I buy it ASAP.  Lately I’ve also been getting books I see referenced in other books.  There’s a ton of research and anecdotal evidence which correlates reading to success and I’m pretty convinced that there’s causality, not just correlation working there.  As such, here are some recommendations for things to read to contribute to your success.

Tools of Titans is one of the most interesting and diverse sets of interviews, pull quotes, and anecdotes I’ve ever read.  Does anyone else feel like Tim Ferriss is the next Shep Gordon?  Read this book if you’re an interesting person, or want to be an interesting person, or want to find other great stuff to read.

Extreme Ownership is referenced in Tools of Titans since Jocko Willink (one of the authors) was interviewed by Tim Ferriss. Read this book if you lead people, want to lead people, or to find out how to become a better team member.  Each chapter starts with a (literal) war story from Iraq, but if you’re not into military stuff you can actually skip to the Practice and Application to Business sections which follow.

Rands in Repose is tied with Seth’s Blog for my favorite blog. Michael Lopp is a brilliant manager with enviable writing skills.  Read this blog if you manage technical people or you are a technical person.  His book Managing Humans is also excellent, but the blog is not to be missed.

Safari Books Online is my secret weapon.  Yes, it’s $399 per year and that’s not cheap but combined with their Queue app it’s a bargain if you’re a technical person who likes to learn.  In the last year I’ve read through dozens of O’Reilly books and watched a couple of their training videos.  The books alone would have cost me triple or more.  If you are a developer and like to learn from books, this one is a no brainer.  If I were running a company with employees, buying the team version would probably be on my list for recruiting top talent.

Okay, one more just for fun: Living with a SEAL is one of my favorite books to give to people.  My friend read the entire thing on a red eye from Seattle to Miami one night after I convinced him to “give it 4 pages and see what you think”.