🥁 How Looking Young at Work Stopped Being My Problem

I’m Allison Stadd, drummer turned CMO, and I write for people who want the way we work to work for us.

This week’s soundtrack:

“How old are you?”

“You’re so young for your role!”

“You’re so accomplished for someone your age.”

If I had to guess how many times people have remarked on or asked about my age in a work setting (I’m really bad at those guess-how-many-jelly-beans-are-in-the-jar games), I’d venture something like 2,000. Maybe 5,000?

I’ve always looked young. It runs in my family.

My mom looks 20 years younger than her age. It’s become a fun parlor trick getting people to guess how old we are.

It was a real pain in the ass the summer all my friends weren’t quite 21 but could get away with convincing bartenders and liquor store cashiers to serve them, whereas my baby face was a dead giveaway.

It’s one of those things I used to get so annoyed about people telling me I’d someday appreciate (“you’ll love it when you’re older!”), and now, what do you know, I do appreciate.

Looking young was also exacerbated by the fact that I often clicked more with people a few years older. Through every phase of my life, leading up to marrying someone eight years my senior, I made older friends and was told I was “wiser than my years” and “had an old soul” or was “mature.”

Who knows, people like to tell kids weird things.

But regardless, looking young was a challenge in the workplace for so many years.

I’ve—big exhale—finally gotten to a place of spending zero energy on it. I’m all out of flying figs to give. Or else I finally look closer to my age (I did notice new wrinkles recently 👀).

The reality is, looking young can hold you back. According to the BBC, people who look older are more likely to be considered for high-status managerial roles and deemed more suitable for jobs requiring a higher level of education. I’ve personally experienced too-many-to-count instances of disrespect due to perceived age.

But it’s not insurmountable.

If you’ve ever grappled with this, or know someone who has, I thought I’d share a few reflections on how to move through it: how to respond when someone asks how old you are, if it’s worth actually trying to look older, choosing when to address it directly vs. let it go, and more.

Three moments stand out when I think about my experience dealing with looking young in the workplace:

I’ve always straddled two worlds: full-time and freelance. I started freelance writing my senior year of college and have really never stopped.

One of my first clients, who hired me to ghost-write for some of the businesses she did PR for, remarked during an ordinary status call how mature I seemed for my age. Irked, I told her some dude had just asked me outright, at a work dinner the other night, how old I was and how much that had wrankled me.

She said she could relate from earlier in her career and told me exactly what to say.

“Ask them how old they are.”

I’ve never forgotten that guidance. I’ve used it a few times when people have had the audacity to ask my age, but more commonly I’ve channeled the attitude. If someone is wondering my age at work, they’re either a) purely curious and my irritation over it is more my stuff; or b) they’re being judgmental and it’s a good reminder that I can speculate right back at them.

I was catching up with a mentor some years ago and explaining how, having been recently promoted to a very senior role leading a large team, I was struggling to feel worthy of the position. I told her my self-consciousness over my seniority at a non-”senior” age was getting in my way.

She listened, let me finish. Then frowned and said:

“I don’t actually think you’re that young for your role.”

She told me about several other mentees in her orbit and folks in her organization who were my age or even younger and at my corporate level or above.

It was a perfect reality-check. It also made me feel dumb in the best way 😂

Maybe you’re not actually that young, objectively, for whatever role you’re filling. As you get older and more experienced, sheer years matter less.

I’d been spending so much time hand-wringing over my perceived youth I hadn’t noticed how much time had passed.

I’m embarrassed to admit this.

But, even after so many years grappling with looking and feeling young, I committed the ultimate pot-calling-the-kettle-black offense.

When interacting with a new colleague, a fellow VP at the time, I instinctively categorized her as “young” based on her face alone. Before I even consciously clocked it, after a couple of Zoom calls with her I realized I thought of her as young, maybe even younger than me.

Again, embarrassing!!! After all the time and work batting down this very concern, I’d drawn the same conclusion about someone else.

But almost instantly, I realized something else: she was super impressive. She was articulate, strategic, a clear communicator, and her experience showed. She had my respect.

It was a helpful illustration of what the best case scenario could be of people’s perceptions of me: fine, they may think I was young; but that didn’t mean they didn’t also respect me.

I used to constantly overcompensate for looking young by emphasizing my age: finding excuses to mention it, investing effort in looking older.

I realize four things now:

1. How annoying over-credentialing is (no one likes a name dropper, let alone an achievement dropper)

2. Dressing for the age you actually feel is more powerful than dressing to prove something

   1. Some unlocks for me on my looking/feeling older style journey: bold glasses (I have and love these from Jimmy Fairly and these from Eye Buy Direct in both purple and green), shorter hair (not as short as “the cut”), a vintage Casio digital watch

3. At some point the math stops mattering: 10 years is 10 years, 15 years is 15 years, etc., regardless of your birth year

4. Results are the ultimate equalizer; that old chestnut “be so good they can’t ignore you” is legitimate

Before I summited Mount I’m Comfortable With My Age, I wore the knees out of this quote:

“It’s not about how many years of experience you have. It’s about the quality of your years of experience.” – Jacob Cass

Put differently: you don’t have to win every room; you have to win the right ones.

I know this sounds clichéd but I really mean it: the people worth impressing aren’t counting your years. They’re watching how you think, how you listen, how you make decisions, what kind of relationship residue you leave around you.

And turns out, the best thing about getting older is caring less about proving it.

Have a great week,

Allison

Folks across 42 U.S. states and 73 countries from companies like LVMH, Unilever, Salesforce, The Atlantic, and The Home Depot are reading along. You in?

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