Are You Winning?

For years, it appeared I was. I was one of the youngest leaders in my industry and one of the only women at my level.

Being a young, successful woman should have given me a huge sense of pride in my achievements.

But what might have felt like a victory often felt hollow.

Imposter Syndrome? It actually wasn’t that. I had confidence in many of the things I was doing. I felt I deserved to be there and was as good as (and sometimes better than) my older and predominantly male colleagues.

What felt hollow was that I was alone in my experience.?

I was perceived as an “insider” by those I led and by an industry that gave validation for title, salary and power.

But in my day-to-day work, I felt like a complete outsider.

While I was celebrating a new business win over lunch at my desk, my male peers were bonding at a 10k run or over a two-martini lunch (or occasionally both - it was the world of Mad Men, after all). I couldn’t keep up in either sense and in the early days, I didn’t have my own version of that.

Luckily, somewhere along the way, the scales tipped.

As time went on, more young, driven, smart women gained a foothold (stiletto-hold) in the business, and more women were promoted into positions of leadership. I wasn’t the only senior woman in the room anymore.

I wasn’t the youngest either.

That was a good thing.

With enough of us in tow, we created our own version of the 10k and Mad Men lunch.

Our tipping place was the Mad Women Ladies Room.

The Ladies Room was a place of respite (except for the flushing) and a place to talk without being overheard. It was a place to share advice, trade stories and lend or take a hand as needed.

Have you seen groups of women walking together to the ladies room? It could be that this is where it all began.

It all happened in the days of open floor plans and cubicles, where we had to seek a place to bond and bitch in private.

While my celebration of being the youngest and the first had felt hollow, now being part of the early stages of change felt like an explosion of growth.

It was a crucial lesson in the value of bonding. Proof of the strength in numbers. The realization that victories are meant to be shared, and failures are not always fair or your fault.

When I realized I wouldn’t be the youngest or the first forever, I saw my place as part of a much larger whole and understood that the size of that whole was not fixed.

Fast forward to now.

Some may say I’m in my third life chapter. By most accounts (just ask Chat GPT), the third chapter means the last chapter.

I’m one of the older people in the room.

With time comes the awareness that still having much to learn is much better than knowing a lot.

With experience comes the realization that another door will always open, and what’s behind that door may be realizations, connections and opportunities never before imagined.

From the perspective of having lived, one comes to the realization that framing life in terms of winning means that there’s a likelihood that the game will be over once you’ve won.

I’ve only begun to play.