Close to the edge

I’ve done more reflecting, and had more discussions with friends, since my first career rumination.  I’ve gravitated to focusing more on how I’d feel in different situations.  Herewith, a potpourri of brooding.

At-will employee vs. contractor

A basic doctrine of American law is at-will employment.  This is the employee’s and employer’s right to terminate the employee’s job at any time, without notice.

Federal and state law have defined statutory exceptions to this.  For example, employment agreements can stipulate termination notice periods and severance pay. Generally, absent an employment agreement or wrongful termination, you can be canned without notice at any time.

I’ve been wrapping my head around the differences between at-will employment and contractors.  What are the pros and cons of each, and why should one choose one over the other?  If there are no fundamental differences, maybe the choice should come down to a gritty financial calculus. There are many intangible and circumstantial differences, but I’m trying to get at the first principles.

My initial approach was based on absolute attributes. A summary, assuming there’s no employment agreement:

Characteristic Freelance Employee
You can be terminated without notice or severance
You must monitor your career’s direction
You ought to monitor the company’s direction √ but how much is up to you
There’s a clear delineation between the company & yourself
You have perceived mutual loyalty with your company
You have actual mutual loyalty with your company
You have more complicated income taxes √ but it’s easy to learn

But this comparison oversimplifies the positions’ relative strengths and weaknesses, precisely because it uses absolutes. The probabilities in a healthy company are more useful.  Why?  Long story short, all bets will be off in an unhealthy company anyway, and a higher probability event can be discerned in advance if you’re sufficiently aware.

This changes the comparison quite a bit, to:

Characteristic Freelance Employee
Higher Pr(terminated without notice or severance) √ can be much higher
Higher Pr(career direction overhead)
Higher Pr(feeling connected to a greater purpose, and making a difference)
Higher Pr(clear company vs. self delineation)
Higher Pr(mutual loyalty with your company) √ but only if you’re a valuable asset
Higher Pr(quickly migrate to interesting work, and exit unpleasant assignments)
More complicated taxes √ but it’s easy to learn

For now, I’ve altered my thinking to include full-time employment, with perhaps the option of side consulting to use as a network extension.

Yes, I’m sure your tables would be different. But this is my blog and these are my tables. If you don’t like them, see Figure 1.

The company and the boss

Two common errors are to expect a company’s loyalty, or try being friends with your boss.

A company is a soulless beast.  It’s (usually) not evil, but it does act according to its own best interests.  There’s nothing wrong with this…it’s just reality. The company isn’t a surrogate family.

Your boss is…your boss. It’s OK to be friendly with your boss.  If you both believe in your team’s mission, are competent, and have high integrity and character, then it would be hard not to feel something akin to friendship.

However, true friendship is precluded by the positional power imbalance. There’s nothing wrong here, either — it’s just reality.

But companies and bosses do differ.  Companies can be dysfunctional, well-run, fast-moving, slow-moving, informal, formal, serious, fun, and/or any other adjective. They can simultaneously be multiples of these, and they can also attain different states in different circumstances.

Some managers “manage upward,” others “manage downward.”  Some are about process, or teamwork, or metrics, or goals, or stretch goals, or integrity, or winning at all costs, etc.  Some are more ruthless about missed milestones, more understanding, more hard-nosed, or more open.  Et cetera.

Higher RPMs

What turns my crank?  I greatly enjoyed working on TrenchMice, more so than my work in some of the companies prior to it.  A large part of that was the Python and Django technology.  But in a newsflash from the Duh! desk, I realize that a large enjoyment component came from other sources.  A not complete but decent list would be:

  • Feeling connected to a purpose
  • Being part of a (small) team
  • Ownership, responsibility, authority
  • Working with innovative technology
  • Creating something new
  • Creating value

It’ll be hard to find the first four as a freelancer.

OTOH, some argue that the first three are usually mirages, or ephemeral at best.   The movie industry has done very well with an entirely contractor-based ecosystem.  Actors, directors, etc. were employees of the studios in the old days.  Since circa 1948, the studios sign contractors in the form of actors, directors, post-production houses, etc. A typical movie can be evaluated as a large outsourcing exercise.

Some friends, and my wife, have said my energy level decreases when I talk about preparing to be a freelancer, and rises when I talk about some recent employment opportunities.


Sometimes I’ll percolate on an issue, and it resolves itself without warning.  And it often resolves ancillary issues at the same time.

I’ve recently had two unexpected employment opportunities appear on the horizon.  I’m well (if not perfectly) suited for both of them (even if I do say so myself). They’re exciting, in different ways, and while they have different characteristics, I can see myself having a blast and making a difference in both.

Synchronicity in action.

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