Adulting So Hard, Part 1: Managing

In the last six months, I became a parent, a teacher, and a boss.

And thus died the years of my youth, free of responsibility.

Today’s post is about my recently departed job, and on moving from an “individual contributor” (read: peon) to “manager” (read: still peon, but now with the added weight and responsibility that if you screw up, somebody else’s life may be ruined).

First, though, the obligatory music video:

I bet you feel sorry for whoever had to report to me, eh?

Now that that’s over, let’s all file in a quiet and orderly fashion to our Systems Conversion Transaction Confirmation Process Review meeting. Yes folks, that’s a real meeting. That I once attended. Count’em: six consecutive nouns. Aren’t I lucky?
Decorative Line

In which I attempt to slice the Gordian knot of corporate bureaucracy and end up cutting my hand, resetting our “Days Since A Metaphysical Accident” calendar to Zero.

Processed with VSCOcam with f2 preset

In August, I hired my first direct report. (I won’t be using her name here. I have no idea if she would mind being named or not, but preserving privacy seems a prudent precaution.) The hiring process went about as I expected, save that I was working remotely and hiring someone you’ve never met is more than a little trippy. Still, I was confident that I made a good decision (and as of the date I left the company, still am; I think she’ll have a great career). Like a kid on his first day of school, I was all prepared to welcome her and be The Best And Most Overeager Boss Any Employee Could Want.

After that first day, and first week, I had a whole new respect for bosses. I should have personally called each of my prior managers to say Thank You, purely for their willingness to put up with arcane procedures, obscure bureaucracy, and my whininess over a 3% raise.


I am amazed just how much goes into bringing someone on-board. Just getting her set up on our labyrinthian systems and computer programs took the better part of two weeks (!). I spent so much time trying to get IT to fix problems and issues I may as well have learned Linux and added her to all the systems myself.


She was a quick learner and took good notes, but you don’t realize how much goes into helping someone learn a complex industry and business. There was a point I literally needed to replenish my electrolytes because we spent so much time training. It’s not just the technical parts either, like “How does universal availability work in a 403(b)(7) plan?” It’s stuff like, “Where are the bathrooms?” and “How do I book a meeting?” Oh, that’s right – SB uses a silly system to book conference rooms that’s not intuitive at all. Let me show you.

And Then I Up and Quit

Which I felt bad about. Truly. It wasn’t exactly a last-minute decision that I’d be staying home, if you catch my drift, but you can’t exactly broadcast that sort of thing. So for many reasons but a large one being my new report’s happiness (and sanity), I did my best not to have long-term short-timer syndrome.

She was about as good an employee as I could have hoped for. She was smart, studious, and self-reliant. And I was genuinely sorry to depart as her manager when I quit. But in a lot of ways, she’ll be better for it. I can tell now that, while remote managing is possible, it should be the employee who is remote, not the boss. And effort aside, I was probably a subpar manager for her. My first time managing an employee, my being remote, and the complex and difficult nature of the business all stacked the deck against me. I made it work, but it was never going to be a great situation.

So I wish her well. I know she’ll do fine without me, and I hope to have the opportunity to manage someone again in the future. In the meantime, I need to go manage my daughter, who from the sound of her crying is currently dying from lack of food, given that I haven’t fed her in nearly fifteen minutes.


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