For years, I’ve been hearing firms describe their cultures as “entrepreneurial,” and I hardly paid the slightest attention. Like “collegial” or “collaborative,” it just seemed like so much white noise. Then finally I heard it once too often and had to face cold reality: I had absolutely no idea what these people—a lot of smart, articulate people—were talking about.

Let’s go to the dictionary, where we find:

/äntr?pr? no?or??l/

1. characterized by the taking of financial risks in the hope of profit; enterprising

Other notions orbiting around the concept of entrepreneurism include engaging in genuine innovation and invention (to the extreme of shattering the status quo), proceeding decisively in the face of profound ambiguity and uncertainty, and shouldering the personal risk of sacrificing years of reliable income provided by others for whatever rewards you can persuade the market to deliver—with a meaningful risk those rewards could be nonexistent.

This is an audience participation column, so I ask you this: Would you describe your own firm as “entrepreneurial?” Are there firms you admire or look down upon that you’d describe as “entrepreneurial?” What mental image or behavior, what cultural archetype or partner personality type, pops into your mind when “entrepreneurial” is used to describe a firm?

Now that you have solidified your own image, I’ll tell you what I came up with when I forced myself to engage in this exercise: Anarchy.

“Entrepreneurial” seemed to me a code word for utter undisciplined chaos: Each partner pursuing his/her own preferences, based overwhelmingly on opportunism and not a roadmap, rigor, focus, or anything whatsoever having to do with a larger integrated strategy—heaven forfend one developed on the premise of a “one-firm firm.”

We’ll get back to anarchy in a moment (yes, I hear disagreement on this score), but let’s stick with “entrepreneurial” for another moment.

Can one really, seriously, be an entrepreneur when an income from several hundred thousand dollars year to up or to way way up, generated by the powerful machinery of the firm one is a partner in, is essentially assured? When one is not remotely putting one’s future livelihood, even for a year or two, on the line? When any personal capital invested will be returned quite promptly and in full, if you bail out? When a painless exit strategy (we’re all elevator assets, remember) is a few phone calls away? When the last Big New Thing that was invented in your chosen industry was the Cravath System ca. 1900—and you’re not dreaming of the 21st Century version 2.0 of the Cravath System in any event? When the number of employees relying on your perspicacity and market savvy for their livelihood is, well, precisely zero?

Or we could approach this from the psychological dimension.

Entrepreneurs are:

  • Risk-tropic
  • Creative
  • Intuitive
  • Trusting
  • Big thinkers, and
  • Extremely resilient.

Lawyers are:

  • Risk-averse
  • Conventional
  • Judgmental
  • Skeptical
  • Detail-oriented, and
  • Over two standard deviations below the population norm on resilience.

As for “anarchy:” We know as well from studies of lawyer psychology that we are autonomy-seeking missiles. We don’t want to be guided, much less managed. This can be a strength in the practice of law, where it permits us to be creative and iconoclastic in our approaches to issues, but when it comes to running a law firm it can be a nightmare for leadership.

Understand what I’m saying and what I’m not saying.

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