Stories about Software


The Opportunist’s Guide to Start Consulting (Abridged)

Given the recent launch of Developer Hegemony, I decided to address a reader question.  This question hits near and dear to my heart and to the subject matter of the book. I’m going to paraphrase for the sake of anonymity.  But, either way, it amounts to a question about how to start consulting.

But First, Some Housekeeping

Before I dive into that, though, I’d like to make offer some links.  If you want to hear and read more from me, I offer you the chance.  Check these out.

And now, back to your regularly scheduled post.

The Reader Question

Without additional preamble, I’ll offer up the (paraphrased) reader question.

I’m currently a developer, and want to transition to freelance consulting. But I’m not quite sure where to start.. Do you have any advice on that? How did you manage to start a consultancy business?

First of all, understand the dichotomy here.  He asks for my advice and he also asks how I did it.  I ask everyone reading to understand that these aren’t necessarily the same thing.  In other words, I can tell you exactly what I did, but that doesn’t mean I think you should do it in exactly that way.

Oh, don’t get me wrong.  I don’t think I made any horrible mistakes or anything like that.  But I kind of wandered my way through the experience, not entirely sure at the time what I wanted.  Unlike the reader asking the question, I never explicitly decided to become a freelance consultant.  In fact, I just had some free time and wanted some extra money.

How I Started Consulting

I’ll go through my own narrative for this first.  It hardly makes for a methodical how-to, but it contains some elements worth noting.

I started a graduate CS degree in my early 20s.  I worked on and earned the degree while also working a full time job.  As a result, I became quite used to working beyond a normal work day.

When grad school ended, I had something of a gap.  I then filled it by doing two things: blogging and moonlighting.  I took on relatively small, fun projects with lots of autonomy.  These I earned through my network because I had no real urgency other than wanting extra money and experience.

A couple of years later, I went to work for a custom app dev shop full of software pros.  Oh, it called itself a consultancy, but so does every company that writes software for other companies.  Still, it familiarized me with the mechanics of selling app dev (proposals, billing, statements of work, etc).

Eventually, I decided to leave the world of salaried employment and strike out on my own.  By the time I did this, I’d been moonlighting, had published Pluralsight videos, and had experience with how a shop sells app dev.

Distilling the Lessons

Let me now crystallize my experience into some pieces of wisdom.  Specifically, consider that I managed to learn some thing piecemeal before going off on my own.  And also, consider that I make a definitive distinction between app dev and consulting.

First, I moonlit (moonlighted?) a bit.  This gave me experience dealing directly with buyers of my services in a low pressure situation.  I learned a bit about contract negotiation, invoicing, and the like at a time when my livelihood didn’t depend on it.  I also incorporated during this time, once I decided I’d make moonlighting more than a passing fancy.

Moonlighting taught me a bit about how to run my one person LLC.  But going to work for an organization that did some of these things at more scale gave me additional perspective.  I learned some new tips and tricks, and I also got another perspective on some things I did myself.

I picked up some leadership skills as well before going off on my own.  In different organizations and at different times. I had team lead roles.  I also managed developers and ran a department.  This helped my consulting, albeit indirectly.

And, finally, I had marketed myself.  By adding the blog and Pluralsight courses to my public presence, I established some credibility among potential buyers.

How You Can Start Consulting

What I’ll offer as advice obviously depends heavily on your timeline.  But I’ll assume that nobody has pressing need to flip to consultant immediately.

First, lay some groundwork.  Decide on what Book Yourself Solid author Michael Port calls a “who and do what” statement.  I help {who} do {what}.  For instance, I might today say I help software developers become consultants.  When you decide on this, start using blogging, speaking, and other means of raising your public profile to establish yourself in this context.  Do that steadily as you execute on other steps.

Now that you’ve started to market your eventual services, you need to learn about consulting and free agency.  I prefer low risk approaches, so I’d suggest doing this while gainfully employed.  Learn enough about marketing, sales, finance, and business that you’d know how to find, acquire, and bill clients.  Incorporate a business for yourself.  Start working on things like your invoices and contracts.  Learn this stuff with zero risk.

Once you have that squared away, start taking on small, low-risk gigs.  Get comfortable with every facet from client acquisition to following up on late invoices.  While you’re doing that, size up what happens at your current employer.  Think how you’d sell your services and to whom.  Start trying to position yourself as an adviser, and one that understand the business.

At some point, your moonlighting will push you to the point that it conflicts with your day job.  At that point, you have a decision to make, and I doubt you’ll struggle with it.  It’ll feel risky and uncomfortable, but you’ll be ready.

I Could Say More…

And I probably will say more at various points.  But I think this answers the question for now.

For those of you reading that follow the blog regularly, I’d ask you to consider something.  As I pursue my own lines of business now exclusively, I’m weighing what to offer next as a follow up to Developer Hegemony.  I have some ideas in the most general sense.  I’d like to offer info products and perhaps eventually services for developers looking to take charge of the software development industry.

Some ideas I’ve had include courses about facets of business or about hanging out your own shingle.  I’m also leaning toward writing a book about going from developer to consultant (meaning an actual consultant that gets paid for advice and not for code).  But I’d like to hear from you reading as to what you’d find valuable.

So feel free to use the form below to let me know what you might like to see.

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[…] actually wrote about a related topic recently.  But that question more concerned my personal background and how to become a consultant. […]

Ron HD

I like your ideas for future topics. I’d love to see more on how to find and win clients. Not just general marketing, but actual sales.


[…] with a well established consulting practice could earn […]