“When I was a boy of 14, my father was so ignorant I could hardly stand to have the old man around. But when I got to be 21, I was astonished at how much the old man had learned in seven years.”

~ Mark Twain

Being a boss in 2019 is…the worst.

First of all (of course), no one cares if it’s the worst. You’re the boss, so: “who cares about you, you embodiment of privilege.” But I often feel like a good leader—willing to take risks, doubledown on integrity vs. short-term fear or profit…

…and a vulnerable, clumsy to-put-it-politely, giving, fallible boss/manager. But the truth is bosses aren’t bosses, often. Often, they set out to create something—she or he is an entrepreneur. They set out to create something—a very different skill or interest than being any good at managing, which is its own humbling path of listening, learning, communicating.

Secondly, this millennial thing–if that’s what it is–basically presupposes that “I may be young and new at this job but I know everything, hierarchy is dead, I have nothing to learn from you, I know everything, you may give me direction and I may not but I won’t do it, and that’s your problem, not mine.”

On the other hand, when I was young, new at a job, I chased my mentors around for days just hoping for 5 minutes of their time, one sentence of wisdom that I’d then cling to and feed off of for a month. As a boss, now, I communicate 1000x more than any mentor of mine ever did. That’s half-good, and half-taken-for-granted.

So I am glad the hierarchy is flattened, somewhat–but goddamn there’s got to be a middle gear, here. Question, criticize—but not from arrogance, from a place of sharing one’s own wisdom and being willing to learn, too. Other folks, sometimes older, do know things I don’t know! (I ask mentors for wisdom, still, every damn day).

There is a thing called wisdom, called experience, a thing where one generation can pass on lessons to the next not out of patronization but out of investing in your basic goodness.

Thirdly, no boss can ever talk about this, except quietly with other bosses, because the empowered employees will rise up and kill you—not directly, of course, our anger ain’t brave—but on twitter. So there’s no communication around it, and millennials can continue to bull-in-a-china-shop their way through their 20s, never feeling consequences or learning from boundaries or expectations. But the obvious fact remains: bosses need to be able to express her or himself, too—to learn, share, be vulnerable. News at 11: we’re sometimes at a loss, too!

When I was 25, I remember my boss and mentor asking me to reserve a 1-800 number for a fundraiser. I created the 1-800 number, but got one of the letters wrong–meaning all the money would get lost when folks typed in the wrong code. My boss said to me, sternly but gently: if you were at a normal business, you’d be fired.

I learned.

But being a boss today—any “insult” of consequences becomes a rant on Instagram, or Facebook, or Twitter by the insulted party (i.e., the employee). This is good, in that the hierarchy—too vast in the past, is flattened. But it’s bad, in the sense, that instead of investing in learning, employees often invest in being right. But investing in being right—whether we’re in a relationship, whether we’re the employee or boss—is fragile. It’s my way or the highway. We can’t listen, we can’t grow.

Out beyond ideas of wrongdoing
and rightdoing there is a field.
I’ll meet you there.
When the soul lies down in that grass
the world is too full to talk about. ~ Rumi

So: if you’re going to be a boss…and you want to be a good one…forget your business. You’ll no longer be working. You’ll be serving.

When things are hard, or drama is high, you serve as everyone’s punching bag and therapist, and when things are good, of course, you are forgotten (as a boss should be).

 “Who Knows Only His Own Generation Remains Always a Child.” ~ a quote on the CU Library.

In Buddhism there’s the notion of the three bowls. An upside-down bowl will never take in any water poured into it—we can’t learn anything. A broken bowl will leak, and retain nothing—we have to be present, and focus. An empty bowl, right-side-up, can learn…everything.

PS: the sunny side of today, which I didn’t write enough about: folks if empowered can all be their own bosses, which includes communication and responsibility toward one other, not just independence.

PPS: the truth is I’m very lucky to get to work with amazing people, and I don’t want to be a boss every other day. This is offered up not as a passive-aggressive complaint, or an airing of grievances. It’s an attempt to communicate fallibility, and I-may-be-the-boss-but-I-too-have-no-idea-what-I’m-doing-sometimes.

I had two really good, hard, complete communications today. What prompted this was more talking with a friend in a café about the generational shift in dynamics.

See below video on “Natural Hierarchy,” a Buddhist teaching that’s been helpful in my path.