Why I Gave up Being the Boss
Here’s the thing about being good at your job: sometimes you get rewarded. Sometimes that reward is a promotion. Sometimes a promotion is a change in career that strips away all of the things you’re good at and assumes you’ll be equally deft at managing people, thinking strategically, and delegating the “doing”.
When such a career change takes place, it’s presented like a reward, a gold star with a glint that blinds and distracts. Your ego likes this gold star. Shiny! It swells into all of the spaces in your brain that are earmarked for weighing pros and cons, for thinking critically. That part of my brain is generally flooded with misguided enthusiasm and 3.5 cups of coffee and Wes Anderson and hobby farm daydreams, so maybe I was screwed anyway.
Actually, I wasn’t promoted. I stayed in the same place and accumulated underlings (kidding, kidding! they’re smart, creative babes who will be your boss one day).
So, I was a manager. A boss. Just like that. No multiple-choice exam or retina scan or final thesis or urine sample. I was suddenly responsible for the success of other humans! I imagine I felt the same crushing inadequacy parents feel when they realize the same about their new charges.
Hey, I can bark orders with the best of them: I’m the oldest of three, born with with boss-duty baked in. I, all-knowing and suprememly wise due to my 2 year headstart on my next oldest sibling, took my position seriously, doling out parts in our backyard plays, coaching my brother on the adequate milk to cereal ratio, calling out atrocities as self-appointed whistle-blower. Of course my siblings did not thrive under this “leadership”; they only resented me into their 30s.
My boss’s boss’s boss, our Founder and CEO, told a group of fresh-faced new managers (hey, that’s me!) that management isn’t synonomous with leadership. There goes the only other notch on my career bedpost that potentially qualified me for this job. I was, in the distant past, the President of my high school student council. President of Poster Paint and Much Music Video Dance Parties. I could plan everything from yard sales to career fairs to weddings to 3-week road trips, directing volunteers through my colour-coded spreadsheets. I could lead a raucous group singing of The Banana Song (with actions!). I could lead, but could I manage?
It turns out that, maybe, I couldn’t. Almost 2 years ago my team of one became two. Shortly after, we were a threesome. Delegating isn’t in my DNA (that’s a euphemism for: “mine! my way! everything my way!”) but we were a tight team, tackling a ton of work and ideas together, and I was letting go. We were blurring the friend/peer/boss lines which suited me fine because: holy shit, what is a manager!? Couldn’t I just get away with being fair, and caring about them a lot, and protecting them from bad guys? Wait, that’s parenting.
At the risk of this post becoming even more rambling and tangential, it’s important to mention that “The Great Women in Tech Can Have a Baby and a Career Too Debate” was being waged on both sides in my head, my heart, and the all-women Slack channel at work. I have all the feels (yet, no confident and conclusive answer) about this topic, but this post isn’t about that. Business is business. It was however, the decision to have a family that had me questioning and considering my path. What would happen when I went on mat leave? When I came back? The median age at my company is a lot (like, a lot) younger than I am, and there are few, if any, examples of women returning to work to resume lead roles (and have it all!). Yet. A group of these pioneering women, poised to return next year, are sure to quell all of my fears, right? In the meantime, my decision was this: I would use mat leave as an opportunity to transition out of management and sidestep into a role where I could create again. (I went to art school, you know.) The stress and anxiety of squirming around in skin that didn’t fit wasn’t going to be good for a baby. Work life balance could be an actual thing that I could actually have!
I value happiness above status and money in my work life. I am a doer, a creator, a producer, a maker.
I’m not pregnant yet but two things became apparent: 1. I subconsciously already had a foot out the door, and 2. if I’m feeling this now, why wait?
A younger version of myself might have allowed ego to rule. I’m closer to 40 now than 30, though, and my ego packed up and left a couple of years ago. I suppose I’ve always been pretty self-aware, but self-awareness is now a driving force. I don’t regret trying. I also don’t have any hesitation with telling you that I failed. (The first thing I ever failed was my G driver’s test. I was 22. I was a late-blooming failure virgin, but I’m learning the benefits of crashing and burning and starting over. With perspective.)
My two direct reports aren’t professionally scarred, nor do I think I have completely failed them, because at least I cared deeply. And I tried really, really hard. I do however, know that I’ve hit a ceiling. I can’t grow them anymore if I’m not growing. There is surely some biology analogy in here, but it’s 2AM, so imagine, please, that I would have been witty or artful in some way at this interval.
Last week, I told my boss that I’m stepping sideways. I intended to title this post “Here’s Why I Demoted Myself”, but it’s not really a demotion. In fact it’s only a little diagonal. Downward, but at least to the right. It’s that little dip in the rollercoaster that creates the momentum for the upswing. Physics. Funnily enough, I hate actual rollercoasters. My mother once told me, loudly over the sound of my inconsolable sobbing, that my highs wouldn’t be so wonderfully high if my lows weren’t so low to balance them, so that i should be thankful for them. It makes me sound manic, but at the time it was comforting.
I’ve built my “career” on failure and setbacks and sidesteps. So far, it’s been really positive. A restart is just as good for the soul as it is for my cranky Macbook. Insert 6000 clichés about making me stronger and better and wiser.
On my flight back from Vegas last week, I read Bossypants, cover to cover. I worried that the timing of the read would cause me to doubt my decision. That I’d glean some magical recipe for managing people (and liking it) from a lady-boss I admire. I didn’t. One thing that Tina said did stick with me, however: “In most cases being a good boss means hiring talented people and then getting out of their way” In my case, I think “getting out of the way” means getting way the fuck out of the way.
In the new year, I’m transitioning out of my role, and nestling into a new home on the content team, literally 12 feet from my current desk. I’ll be creating again! My inaugral Medium piece (this one) is my warm-up. I’m lucky to work for a company that gets that management is, like, really hard. The return policy on my boss gig was really generous.
This team that I’ve built? They’ll be fine. They’ll be great with the right manager. Will you step into my shoes?
