The Freelancing Technologist Success Ladder

I’ve been doing a lot of pondering about the different approaches people take to being an independent IT professional.

There are really (at least) 4-5 camps. And they make all the difference in the world when it comes to how happy you are with where you are and what approaches to take when trying to get where you want to be. Each has different trade-offs.

If you aren’t aware of their existence than you may be “barking up the wrong tree”.

Many think the folks more successful than themselves are better at marketing, lucky… or some other mysterious attribute. That may be true but often they’re in an entirely different business. (It’s no wonder folks get frustrated trying to chase others when they are on the outside looking in.)

They’re chasing the outward results someone else is achieving but don’t understand the underlying strategy or positioning.

The table below documents what I call the Independent IT Professional Success Ladder.

This ladder will, undoubtedly, annoy a few folks. Too bad. If they get over it, they may learn something about where they are and getting exactly where they want to be (and staying there.)

Your position (which is under your control) on this ladder drives your strategy, income, level of success, types of clients, hours worked, quantity and types of client, projects, and engagements, durability through varying economic climates, and market and specialization agility. So, basically everything. :)

More importantly though, clearly knowing where you are and where you want to go should reduce frustration and give you greater clarity about how you are going to get to where you want to be.

Do you have to be at the top to be successful? Not at all. You define what you want success to be. There are different trade-offs to be made at every step on the ladder. Which ones make sense for you to stand on is a matter of personal preference & opinion.

Do you have to take go up the ladder in order? Nope. But it often works that way.

If it’s not already obvious, knowing where you’re at and where you want to be is key to your happiness with your level of success. It is the key to assembling an effective strategy for your business.

My point in sharing this ladder is four-fold:

  1. To get you thinking about where you want to be (your destination)
  2. To get you thinking about where you are (your present-day starting point)
  3. To get you thinking about how you’re going to get from where you are to where you want to be.
  4. To give you greater clarity if you’re happy with where you’re at already so that you can make sure you’re armed with an appropriate strategy to stay there in an effective and efficient way.

It also puts all advice you hear from or observe in others into context:

  • Where are they?
  • Where are you now?
  • Where are you headed?
  • Which things are they are saying or doing make sense in your context… and which don’t?

The Independent IT Professional Success Ladder

(Role then Key attributes)

Thought Leader -

  • Perception of “when we want the best we absolutely must get this guy”
  • Large body of work (books, reports, articles, interviews, speeches, case studies, client lists, endorsements, testimonials, etc.)
  • Above market fees, often way above so-called “market” fees. Clients consider fees an investment, judging based upon outcome and perceived quantitative as well as qualitative value versus tasks/inputs.
  • Highly differentiated/unique (perception)
  • Respected and viewed as an equal (if not more) by buyer/client

Trusted Advisor -

  • Relationship akin to having an outside financial advisor/planner, long-time personal family lawyer, trusted business coach
  • Advises on a variety of matters, informally and formally, which may or may not be directly technical
  • Contains many, perhaps most, of the attributes of the Management Consultant and Technical Consultant
  • Strong bond with the client that is based on more than just being an expert and meeting expectations
  • Respected and viewed as an equal by buyer/client

Management Consultant -

  • Strategy emphasis over tactics
  • Executive level discussion
  • Business-orientation yet tech-savvy
  • Straddler of business & technical communities. Not simply a geek or computer guy.
  • Leadership potential,
  • Tendency towards “trusted advisor” status
  • Primarily concerned with figuring out what should be done to achieve the organization’s objectives not necessarily exactly how to do it.
  • Independent of any vendors

Technical Consultant/Project Manager -

  • A small body of work
  • Agenda definer collaboratively with client.
  • Provides pro-active recommendations or findings (formally or informally) at end of engagements.
  • May follow a (more) typical general consulting approach, process, methodology.
  • Leadership capabilities.
  • Tendency to be outcome oriented. Sometimes paid as such rather than task oriented.

Freelancer/Contractor/Technician – 

  • Akin to an employee-on-demand
  • Paid hourly, generally based on prevailing market rates.
  • Very difficult to charge above market rates.
  • Minimal loyalty even if client is delighted
  • High likelihood of being typecast into “the computer guy” role
  • Any formal interaction with business requirements is accidentally or peripheral
  • Often a generalist with some specialization tendencies. Or a deep specialist with little generalist capabilities.
  • Generally short-term tasks and projects
  • Unlikely to have or need a proprietary methodology
  • Often break-fix
  • Little real influence
  • Primarily concerned with properly carrying out decided upon plans (agenda implementor, not agenda setter).
  • Usually paid based upon tasks / work input rather than output.
  • Not a peer with management. “Hired help”.
  • May be respected by buyer but not necessarily considered a peer
  • No client independent body of work

Some final notes regarding the ladder that are, in general, true:

  • Income level/pay scale is in descending order, highest at the Thought Leader level
  • The farther down the ladder you are the more difficult it is to differentiate yourself
  • Attracting new and higher quality business is easier the higher up the ladder you are
  • Sales cycles are often shorter the higher up the ladder you are
  • Specialization as well as being a broader generalist can exist at any level
  • Expertise remains important at all levels but is not the end all be all. It is quite possible to be the poorest, most over-worked, most stressed out, and smartest guy in your niche at the very same time. Doh!
  • Pinpointing where you are (or want to be) is not an exact thing. The ladder is meant as tool for pondering your strategy within. You don’t have to agree with every step or attribute to benefit from the thinking it encourages.
  • I put this together for my own clarity and planning originally. I did not spend hours editing and perfecting it. It was unnecessary once the big picture became clear. Feel free to build your own that is more agreeable.
  • Perception is reality
  • There are exceptions of exceptionally successful firms/individuals at all levels. In reality though these exceptions only appear to be exceptions. In most cases they are borrowing strategies from more than one ladder and simply appear to be at one step when they are effectively really at an entirely different level than you think. :)

Share your thoughts on the ladder and this viewpoint with me by hitting me up on Twitter, posting on reddit’s /r/freelance, shooting me an email, or commenting.

What do you think of the ladder?

Do you think it’ll help you in your strategic thinking?

Where are you right now?

Where do you want to be?

Note: I published this to my private email list about 4 years ago and got a lot of positive feedback on it so I decided to re-publish it here on my freelancing blog.

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