Definition of Winning

Listen to this article.

0:00

/1012.84059

1×

Last week I wrote about what it looks like to fight for something. So many of you wrote back to share the ways you’re already in the fight.

Some of you fight to save our democracy (thank you, Sam). Others shared personal stories of fighting on behalf of senior citizens and veterans (thank you, Cecelia). Some wrote about fighting for our planet (thank you, Marlo). Others wrote about fighting for children with disabilities (thank you, Julia), and for other causes that keep them up at night (thank you, Yvonne).

And then one of you asked me a question that I’ve sat with all week: What does it even look like to win?

I love that question. In fact, I think it is one of the most important questions we could ask ourselves. And truthfully, I think most of us never stop long enough to actually do that.

When I was younger, I thought winning meant scoring a certain job, title, or recognition. It meant being chosen. Being seen. I remember those moments when I didn't land a big exclusive interview—I felt like I was failing at the business I was in. Even worse, I felt like someone else had been chosen over me. I know in the scheme of things that might sound small. But in the day-to-day experience of striving and trying to make your way, those moments add up. You end up feeling discouraged. Defeated. Disillusioned.

I hear about people experiencing that feeling everywhere I go right now. People who have played by the rules, paid their taxes, worked hard, been good parents and good children and good citizens, and yet who don’t see how they can ever cross the finish line. People who look at the cost of a home and know it might never be within reach. Who look at the cost of caring for an aging parent and think: How? Who feel that no matter how hard they try, winning is something that happens to other people.

I especially think about parents. So many parents today do not feel like they are winning. They struggle with school issues, with their children's mental health, and with their own mental health. They lie awake at night asking themselves: Am I doing something wrong? Will this ever get easier? I remember that feeling so well. I'd look at my kids in middle school and high school, with all the issues on the table, and wonder: Am I doing this right? Or am I failing? Will it all be okay?

And it's not just parenting. The rules have changed at work too. The metrics have shifted. AI and algorithms have thrown everything into chaos. No one seems to know what it means to win at work anymore. The goalposts keep moving, the game keeps changing, and most of us are just trying to keep up.

We are entering an era where machines will seem like they are winning at everything. They will get the jobs our kids are trying to secure. They will change every business. And in turn, they will force all of us to look inward and decide what is worth fighting for or uniquely our own. What will we humans define as success? As victory? That's a dialogue we should all start having right now.

Meanwhile in politics, there are so many people running for office who want to prove to us why they should win this November. In the coming days we will be inundated with news regarding the midterm elections. Some will even tell us that these are the most important elections of our lifetime. And I have no doubt in my heart that the millions of Americans who don’t feel like they’re winning will fight back and throw out the politicians who are too busy building ballrooms, renovating buildings, waging wars, and throwing people off health insurance to care. It will be the people’s chance to redefine winners and losers.

I often think of those who have all the trappings of success and wonder. Why is it not enough? Why is more always on the table? Why are some so stuck in this old game that many no longer want to play? It’s tired and it’s outdated. Those who inspire me and take my breath away now are the people serving on the frontlines of humanity—individuals caring, serving, and tending to the hearts of those who feel forgotten, unseen, and alone. That’s what winning looks like. We as people can rewrite old rules and insist that we play a new game.

I think we owe ourselves, our kids, our friends, and our communities a broader, richer, more honest definition of winning. Think about how other cultures define winning. In Denmark, they talk about hygge, a concept with no direct English translation. It means something like coziness, togetherness, and the warmth of being with people you love in a space that feels safe. Think of it as a different definition of winning. Not scoring the corner office, but gathering at a candlelit table with people who know you.

In Japan, there is ikigai, a word that describes what gives life value and joy. It can be a purpose, a passion, a relationship, a hobby, or simply something that makes life feel worth living. In the West, ikigai is often portrayed as the intersection of what you love, what you’re good at, what the world needs, and what can sustain you. But the Japanese concept is broader than that. It can be found in the small things that give your everyday life meaning. Winning, in that framework, is not about accumulation. It is about alignment. Living a life that feels like yours.

Meanwhile, in Bhutan, Gross National Happiness offers a broader way of thinking about progress than GDP alone. The country has developed a framework that evaluates well-being across nine domains. They even do periodic surveys where they evaluate their population across those domains: psychological well-being; health; education; time use; cultural diversity and resilience; good governance; community vitality; ecological diversity and resilience; and standard of living.

And then there is the current American definition of winning. Hard work. Financial success. Professional achievement. Status. The bigger house, the better title, the higher number. We are not wrong to value hard work. But somewhere along the way we forgot to also value character. Kindness. Integrity. Honesty. Humility. Service. The quality of our relationships. The way we treat strangers. The life we live when no one is watching.

We so rarely hold up a life of integrity and care and service and say: Now, that’s winning.

But I think that is what winning really looks like. In fact, I think it might be the only kind of winning that actually lasts. I think in this era of AI, winning at being human is where we should focus our efforts. (And on the subject of being human, I encourage you to read our contributors’ pieces in this week’s newsletter, which beautifully articulate different ways of doing just that: Marisa G. Franco on making peace with hard feelings , and Danny Meyer on creating connection through hospitality .)

So let me offer you a different definition of winning, one I have earned the hard way. In my opinion, you are winning when you feel loved. You are winning when you have a purpose bigger than yourself. You are winning when you have a mission—something that gets you out of bed in the morning not because you have to, but because you want to. You are winning when you are surrounded by all forms of love. When your kid calls and asks you to take a walk or go to dinner or just spend some time. When you can sit in silence and be okay. When you look in the mirror and like the person looking back at you, even if they're older, even if they have wrinkles, even if they're not the person they used to be. You are winning when your dog jumps up on you like you are the greatest thing in the world.

One of our Sunday Paper PLUS members named Polly plays the harp in nursing homes. That is her version of winning. MJ does a podcast focused on helping others at midlife. Terry fights for women who have spent years adapting and keeping the peace. She's fighting for their return to self. Jen fights to create community.

The list goes on. This is what a community of Architects of Change looks like: people of different ages, different backgrounds, different genders, and from all different states and countries, actively trying to make life better. That should give us all hope. And they are demonstrating how real winners behave.

What I love about our work here at The Sunday Paper and through my publishing imprint The Open Field is that we publish voices that can inspire us to find new ways forward in our own lives. And on that note, I’m excited to finally announce today that my longtime friend Rob Lowe’s new book What I Do Know: A Guide to Living, will be published by The Open Field . The book distills the lessons Rob has learned about constructing a good life after a lifetime of reinvention, sobriety, marriage, parenthood, aging, and a long and storied career in the public eye. I’m so grateful to him for trusting me to help publish his new book and thrilled to share more details with you below.

My point in sharing these examples of people in this community who inspire me isn’t to give you a reason to compare your version of winning to anyone else's. The point is to find yours. It’s time you name it and stop measuring yourself by a standard someone else set for a life you're not living.

It’s time to ask yourself: What makes you feel like a winner? and answer it honestly. Not what you've been told should make you feel that way. Not what you see in the public square.

Today happens to be my son Christopher's birthday, and let me tell you: being chosen to be his mother 29 years ago makes me feel like I won the lottery. Full stop.

When I think of Christopher and my other children, I feel deep in my soul that I am so blessed. They are the most important people in my life, and on their birthdays, I try to tell them how incredible they are. But I probably don't say it enough. Their very existence makes me feel like a winner every single day of my life!

I share that with you because I know this is a place where I can safely express my feelings. I know so many people who have lost a child and who tell me they still feel blessed that they had that child in their life for however long they had them. That love doesn't go away. That sense of having won something profound doesn't disappear with loss. If anything, it deepens.

I also feel like I won with my parents. Were they perfect? No. But I'm not either. Age has illuminated for me that none of us are. So we should probably stop trying to win that race. It's not winnable. End of story.

I feel like I won with my brothers, the same ones who tried to beat me in every possible way growing up and who are now among my closest friends and greatest champions. I feel like I’ve won with all the people in my life who surround me with love, support, and community. The ones who really listen and who I know see me for who I really am.

So what is winning? I know now that it’s not a destination. It is not a title or a salary or a house or a finish line you cross and plant a flag in. Life experience has changed how I see the game entirely. It has changed my view of success. It has reminded me how important failing, trying, and getting back up again actually are. Not as setbacks on the way to winning, but as the substance of a life worth living.

Winning and losing. Succeeding and failing. These are constructs made by society and culture. Each of us gets to decide what winning means. Each of us gets to ascribe meaning to the experiences we've had, the painful ones as much as the joyful ones. It is just as easy to believe you are winning as it is to believe you are losing. The difference is usually a question of what you are measuring.

As for me, I am not measuring titles anymore. I am not measuring recognition or reach or any of the things I used to reach for.

Today, winning is feeling a sense of joy. Contentment. Purpose. Love. I have fought hard for a long time to resurrect myself. To come home to myself. To stop running from the parts of myself I didn't understand and finally start making peace with all of it. That is the fight I feel like I've won.

And on a day when I get to celebrate the birthday of one of the four greatest gifts of my life, I feel like the luckiest woman in the world. I truly feel victorious.

Happy birthday, Christopher. You make me feel like a winner every single day.

P.S. I'd love to know how you define winning right now. Not what you've been told it should look like, but what it actually feels like to you, in this chapter of your life. Write to me. I read everything. And I try to respond!

Also in this week’s issue:

• Want to Be a Better Friend? Learn to Sit with Hard Feelings

• “You Cannot See It. You Can Absolutely Feel It.”

• Maria Shriver's The Open Field To Publish What Do I Know: A Guide to Living by Rob Lowe