Redefining Winning When the Rules No Longer Fit

By May Binstock

Strategic Communications & Executive Positioning Expert

At 2:17 a.m., with a newborn in one arm and a laptop balanced on my knees, I submitted a final assignment for a Harvard Business School course. I hadn’t slept more than two hours in days. My toddler would be up in four. Outside, the country was in political turmoil.

By every traditional metric, this didn’t look like winning.

No promotion. No applause. No headline moment.

But that night quietly redefined success for me.

For most of my career, I helped executives win. As a communications and branding strategist, my job was to build visibility, authority, and influence. The kind of wins that look great on paper and even better on LinkedIn. I believed in that equation because it worked. Until life intervened.

Divorce. Two very different maternity leaves. A global pandemic. Political unrest that made it impossible to sit still. Suddenly, the old scorecard felt irrelevant. Progress was no longer linear. Achievement wasn’t loud. And winning, as I had known it, didn’t fit the season I was in.

I’m not alone. Research shows that nearly 1 in 2 women report feeling burned out by mid-career, and working mothers are significantly more likely to consider stepping back from leadership, not because they lack ambition, but because the definition of success they’re chasing is misaligned with real life. At the same time, studies consistently show that leaders who integrate empathy, lived experience, and adaptability outperform their peers on trust, engagement, and retention.

So what does winning look like now?

In this season of my life, winning looks like alignment over acceleration. Choosing work that reflects my values. Using my voice to elevate others who don’t always have one. Building impact without burning myself out, while raising two young children and staying present for the life I’m actually living.

One of my biggest wins didn’t look like success at first. During my second maternity leave, I enrolled in Harvard Business School’s Design Thinking & Innovation program. On paper, it made no sense. I was exhausted, emotional, and stretched thin. I studied between night feedings, submitted assignments half-asleep, and questioned my sanity more than once.

At the time, it felt indulgent. Even irresponsible. In hindsight, it was transformative. That decision re-anchored my confidence, expanded my strategic toolkit, and reminded me that growth doesn’t pause just because life gets hard. Sometimes, growth happens precisely because it does.

The most important shift, though, came when I broke a rule I didn’t realize I’d been following for years: the idea that women must choose between being visibly ambitious or deeply human, but never both.

For a long time, I compartmentalized. Professional here. Mother there. Vulnerability kept neatly out of leadership. Eventually, that separation became exhausting and limiting. When I stopped hiding parts of myself and started integrating them, everything changed. My leadership became sharper. My communication turned more honest. My definition of success is now more sustainable.

Winning, I’ve learned, isn’t about doing more or proving harder. It’s about choosing intentionally. It’s about recognizing that quiet progress still counts. That resilience doesn’t always look impressive in the moment. That redefining success isn’t a step back. It’s often a step forward.

If you’re in a season where your wins feel invisible, or your ambition doesn’t look like it used to, know this: you’re not failing. You’re evolving.

And sometimes, that’s the biggest win of all.

Connect With May

www.linkedin.com/in/comms-master