There was a season of my life when winning at work felt like the whole assignment.
When I worked in the U.S. Small Business Administration’s (SBA) Region V Advocate role for the Midwest, my job was built on movement. Airports. Hotels. Rental cars. Long days in cities that were not mine. The mission mattered, and I was grateful for the opportunity. But the travel was relentless. I would walk into another hotel room, take off my jacket, and feel that quiet tension so many leaders know. I was doing meaningful work, but I was also missing meaningful moments.
Balancing ambition and family in that season was tough. And it shaped me. It forced questions I still carry now. What does winning mean if the people I love are paying the price for it? What does success matter if the cost is my home?
We do not talk about that enough in leadership circles. We celebrate promotions, milestones, and big goals. We clap for the grind. We reward availability like it is virtue. But selfless leadership asks a different question.
Winning for who, and at what cost? If my family only gets the leftovers of my ambition, that is not success. That is trade. And trades like that always come due.
Here is what makes this tricky. Work gives you feedback fast. You get credited. You get recognized. You get the email, the meeting, the applause. Home is quieter. Nobody applauds you for showing up to the little moments. Nobody hands you a headline for being present at dinner. And because losses do not announce themselves, leaders can drift without realizing it.
You are present physically but absent mentally.
You come home too tired for real connection.
Your spouse or kids get the drained version of you. You miss moments you cannot get back.
Sometimes you do not notice the shift until your house starts to feel like a place you visit instead of a place you live.
We tell ourselves, I will slow down after this season. But seasons multiply. There will always be another deadline, another initiative, another fire, another opportunity you think you cannot miss. Work will always ask for more.
So the real question is not what kind of life you will build someday. It is what kind of life you are building right now.
Selfless Way leadership means the most important people in your life do not have to compete with the most important work in your life. Boundaries are not selfish, they are protective. They keep your calling from becoming your cage. Real winning is sustainable and shared, not one sided.
That is why presence beats perfection every time. Your family does not need the flawless version of you. They need the real version. The present one. The one who listens. The one who shows up in the small moments, not just the big ones.
And here is the part leaders have to own. If work makes you sharper but also harsher, something is off. If you are getting more patient with your coworkers than with your kids, something is off. If you are giving your best creativity to your team and your worst exhaustion to your spouse, something is off.
The goal is not to be admired at work and absent at home. The goal is to be whole.
So the people who love you most get the best of you, not the rest of you.
A few practical moves have helped me over time.
First, a daily handoff ritual.
Before you walk through the door, pause. Breathe. Reflect. Let the day end before you enter your house. You do not have to bring every meeting, every frustration, every unfinished task into the living room. Your family should not have to feel the weight of work before they feel your presence.
Second, a calendar audit.
If someone looked at your schedule, would they know your family matters? Not by what you say, but by what you protect. We make time for what we value. Your calendar is not just a tool. It is a confession.
Third, redefine winning.
Winning is not only what you accomplish. It is who you become while you accomplish it. It is the relationships you hold onto. It is the way your success strengthens your home instead of starving it. A life that looks impressive but feels empty is not winning. It is a warning.
I learned in that heavy travel season years ago that ambition is a gift, but it has to be carried with wisdom. If you only chase vision, you will eventually lose the people you were supposed to carry with you.
Selfless leaders do not just win for themselves. They win in a way that lets everybody they love breathe too.
So wherever you are in your leadership journey, ask yourself honestly. Am I winning at work without losing at home? Are the people I love getting my presence or my leftovers? Is my ambition building a life I am proud to live in right now?
Because the best kind of success is the kind that still leaves you whole when you turn the key and walk through your front door.
Beyond the Title
Beyond the Title is a series of Q&As with alumni of Madison365’s Most Influential lists.
Dr. Damira Grady-Saffold
Vice President of College Culture, Climate, and Community Impact, Madison College
What’s one question every new leader should ask during their first 100 days and why?
Always make your bed. It is this simple morning practice that sets the tone for your whole day. It starts the routine and keeps things calm and in order. When you don’t make the bed, you are most likely rushing and time is thrown off. Make the time to make the bed. Be mindful of your day.
Kabby Hong
English teacher, Verona Area High School
What’s the best advice you’ve received from a mentor?
I had a mentor teacher tell me that the closer you are to your authentic self, the better you will be as a teacher. I think it’s true in the classroom and true in life. Removing the artifice and the insecurities to become who you really are and it’s intensely attractive to others because you can’t fake authenticity.
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