Today is my last day in my current role at work, and tomorrow I start a new position at the same company. I don’t talk much about my job here, but I am currently the Head of Support for WordPress.com, which involves overseeing our largest support division. It’s over 20 teams of 200+ people. It’s a big job with a lot of responsibility. My company is very employee focused and so when I had Edith, I had six months’ paid parental leave — everyone in my company gets this when they add to their family, including men. That time was invaluable.
When I went back to work, I expected it to be difficult, but I just dove right in and for awhile it was fine. A lot of people I work with assume I habitually overwork, but I really don’t. I have firm work/life boundaries and my company genuinely doesn’t require working all the time in order to be successful. Plus we’re fully distributed, so there’s no pressure to put in face time.
But here’s the thing: at a certain point in a leadership career, your job becomes less about doing tasks and more about strategizing and making decisions. That is probably the main part of my job — there are constantly big decisions that need to be made, decisions that affect the working life of 200+ people plus our customers and the business itself. And decisions are something that you make 24/7, not just when you are at your desk. I mull about work fairly constantly, it’s just an always buzzing mental background noise, which didn’t used to be an issue. But now I was noticing that in my evenings and weekends with Edith, I just wasn’t as mentally and emotionally present as I wanted to be. And now in addition to work stress, I had all the worries of new parenthood — whether she was getting what she needed when she needed it, whether I was doing the right things at the right time, etc. It all just started to feel like too much.
But if I left the role, would it be a mistake? Would I lose career momentum? If I ever left my current company (I don’t plan to, but you don’t know what the future holds), would it look bad on my resume? What would other people think? Would I regret it?
I went back and forth on this for months, I talked to my career coach, I changed my mind a thousand times, but finally, I asked my boss if I could move out of leadership. I feel like this story is so cliched, it’s embarrassing even to write. I felt conflicted about moving to a role with less responsibility because when you’re a woman, especially one in what would traditionally be considered a high profile role at work, your actions don’t just affect you; they reflect on all women. I know this is a thousand times more true for POC and especially WOC, and other marginalized groups. I was talking to a friend about pay inequality recently and how women are still paid less for the same jobs and paid for their experience rather than their potential, whereas with men it’s the opposite, and she said “well, partly that’s because men don’t do what you just did.” I got really angry and defensive, but I’ve been thinking about it since, and I don’t even think it’s accurate anymore.
I’m forty, so my view on careers is probably more aligned with what people were doing in the 90s and early 00s than what they’re doing now. The landscape of work has fundamentally changed. Younger people and people in tech have a vastly different relationship with work and their employers than my parents’ generation did (and probably still in more traditional careers and businesses like law, which was my job experience before going into tech).
At my company, a lot of men have done exactly what I just did. Without even really trying, I can think of five right now. Some did it because they became parents, others because they didn’t feel like leadership was the right role for them, others because they just wanted to have less stress and enjoy their work more.
Likewise, almost all the women in executive roles at my company have small children, and they are not going anywhere. These things simply don’t break down along traditional gender lines anymore. But we still act as if they do, and we still pay people as if they do.
I will also say that my own company does a lot right that made this choice very easy for me and relieves a lot of traditional pressures that don’t serve employers or employees well anymore. For one thing, it doesn’t view leadership roles as promotions and it rewards people (including financially) depending on how much value they bring to the company overall, not according to whatever role or title they currently hold. This is to avoid the traditional issue of people going into management just because that’s “up” and sucking at it and hating it and making everyone’s lives miserable.
But the problem is that the rest of the workforce hasn’t caught up with my company. So when I make decisions about my career, I typically worry a lot about what it looks like in the “real” world which I always fear I will have to reenter one day.
In the end, though, what really helped me give up this concern is that ever since I was about 30, I have been prioritizing future security over present happiness, and the current state of, you know, the whole world is making that look like an increasingly foolish gamble. I can’t say if this role change will make things a little harder for me in twenty years, but I also can’t say if the economy will still be functioning in twenty years. So I ought to just do what makes sense for my family right now.
Anyway, the role I start tomorrow is perfect for me — I will be essentially an internal leadership coach, helping team leads all across our company support their team members and thrive in their own careers. This enables me to draw on my long experience in leadership to continue to add value to our company (and beyond just my area of the company as well), but without having to be in a leadership position myself. Also, my lead will be a good friend of mine who brought me into the company ten years ago and who I worked very closely with before, and the broader team I’ll be joining is also full of good friends of mine who I really enjoy spending time with. So, I’m really happy with the decision, and I’m also really happy that I work for a company that enables this kind of progression.