The Business of Family: The Loneliness of Leadership

The first in a series on what building a business has taught me about building a home - and what building a home has taught me about business.

I have spent my career at the intersection of investing and startups. I have operated inside them, founded my own, and sat across the table analyzing hundreds more.  What I did not expect, when I became a mother, was how much of that same terrain I would find myself walking -  this time in a kitchen, the bathtub, or even a swimming pool parking lot.

Someone once told me they thought parenting was one of the greatest lessons in leadership they had ever encountered. It was a small comment, but it reoriented something in me. Before that, I had mostly been surviving motherhood - getting through the days, managing the logistics. After it, I began to see the role differently. Not as a departure from the discipline I had built in my professional life, but as its continuation. Two responsibilities, it turns out, that are far more complementary than I ever gave them credit for - each one quietly refining me for the other.

My father used to come home from church leadership meetings or long days at work and talk about what he called "the loneliness of leadership." He meant the particular weight of decisions that no one claps for - the calls that are right but unpopular, the ones you make alone even when you're surrounded by people. I understood this in a professional sense long before I understood it in any other. I had made those calls in boardrooms and in founder meetings. I thought I knew what the phrase meant.

Then, this morning, I loaded my two-year-old into the car and drove away from a pool we had arrived at only minutes before.

She has been learning to express herself, and hitting has become her language of frustration - worse than usual these last few days. Before we left the house, I told her plainly: if she hit anyone at the pool, we would leave immediately. Five minutes in, she hit her cousin. So I did what I said I would do. I pulled her out of the water, walked her to the car, and drove home.

On the way, we talked: About why we leave when this happens - to keep other kids safe. About calling her cousin later to apologize, once she was calm enough to mean it. About what to do with big feelings. The situation tested my own frustration management as much as hers.

I have been looking forward to this morning all week - catching up with my sister and her kids, and finishing my book poolside. Driving away, I felt the full cost of following through: a devastated toddler, a disappointed sister, angry cousins excited to play together, and a mother who had wanted, quite simply, a few hours to rest. Follow-through is easy to endorse in the abstract. It is much harder when the price is your own dream day.

I could have handled it differently - given one warning instead of an immediate consequence, softened the line before we ever left our driveway. But I hadn't. I had already set the terms, out loud, before we arrived. And once a leader states the terms, the only real choice left is whether to honor them.

This is where the two halves of my life folded into each other. I have sat in plenty of rooms making decisions that made me unpopular - with a boss, a co-worker, an investor. In the moment, those always felt like the harder version of leadership. But nothing in a boardroom has tested my resolve quite like a screaming, heartbroken toddler in a car seat, knowing I was the only one who could have prevented it and chose not to, because the prevention would have cost her - and eventually all of us - something more.

The loneliness of leadership does not stay in the office. It shows up anywhere someone is responsible for the outcome and has to hold a line that nobody around them wants held. My father knew this from the pulpit and the workplace. I am learning it from a pool deck. The loneliness of leadership isn't something to avoid. It's often evidence that we're carrying the responsibility leadership requires. 

As parents, we are teaching leadership while being trained in it ourselves - shaped by the very people we are trying to shape. And while it may feel lonely in the moment, it's also one of the greatest privileges we'll ever have.

What leadership principles have you learned from family life? 

This piece opens a new series on Polygon: the through-lines between building a business and building a home - what each one has quietly taught me about the other.