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Leadership·9 min read

How Motherhood Taught Me to Lead and Help Founders Let Go

By Charity Starrett ·
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A child's handwritten grocery list beside an envelope of cash, a receipt, an apple, and two frozen pizza boxes on a kitchen counter

I didn't set out to be a mother. In fact, I feared it, having been raised by two parents who were anything but nurturing. It was admittedly an accident. Fate stepped in and broke the barriers to make it happen, literally.

I remember looking at the test result with a mixture of dread, fear, and sheer determination, knowing absolutely that my life would never be the same.

Little did I know that I would eventually mother three other children who weren't my own but grew to be through marriage and circumstances. That I would lead other young lives through my writing. That I would guide and impact thousands of lives throughout my career.

I have learned some really important lessons in the almost 20 years since that singular moment.

The most important is this: if you can get a human being from infancy to adulthood safely, you've worked some miracles along the way. Guaranteed. And you might be the only one that knows it.

Parenthood is long-horizon leadership

Parenthood is long-horizon leadership under continuously changing and sometimes even hazardous conditions with incredibly high stakes and no instruction manual. Every single day you're tasked with figuring it out against a risk of failure that never ends. You live in daily fear that some outside circumstance will cause you to fail. But then, even if you magically succeed, in the end, you still have to let go. The entire point of raising a child is to make your leadership unnecessary.

If you succeed, they go out into the world on their own and face the hazards without you. So while you hope for success every day, as you watch it happen, you also dread the day the letting go must happen. The day they no longer need you and you become more witness to their life than a guide.

The $50 experiment

I remember when my kids were pretty young doing something that people around me thought was genuinely crazy. My daughter was 7, my stepson was 8. Dinner had turned into a complaint-fest about what we were eating. As the primary cook, I was sick of hearing it. So I did something radical.

I gave each child a $50 budget for the week and told them to shop for themselves. I had the right to veto any purchase, but they had to choose what they would eat for the week and stay within budget. They could not go over. And if they ran out of food, they wouldn't starve obviously, but they would have to eat what I cooked.

The contrast in their choices was honestly hilarious. My daughter's choices were genuinely healthy overall: fruit, vegetables, chicken nuggets. She naturally chose a pretty good mixture with a little candy and some snacks for variety. I was pretty proud of her choices, they were reasonable. My son, on the other hand, chose almost entirely frozen pizza. Two boxes. A twelve pack of Dr. Pepper. Some snacks. A few energy bars. Internally, the mother in me groaned.

I gently asked him if that was all he wanted to eat all week and without hesitation, he said yes. Gritting my teeth against my own impulses, I kept my expression as neutral as possible and we checked out. I told myself that natural consequences are sometimes the best teachers and a week of nothing but carbs wouldn't kill him.

Of my children, he was my “It has to be my idea” child. I could have spent an hour explaining why frozen pizzas weren't a particularly good nutritional strategy. Or I could give him enough room to discover it himself. I told myself he would still have school lunches and breakfast.

Recognizing which one would actually teach him was part of knowing how to lead him.

The week progressed pretty normally with the hecticness of school and work. Saturday, grocery day, rolled around. On the ride to the grocery store, I asked them what they thought of our little experiment. They both lit up. They loved having the things they enjoyed eating. My daughter said “I probably need more meat this time though. I got hungry really fast when all I ate was fruit. But I noticed the meat filled me up better.”

Internally, my heart leapt for joy. What an amazing lesson! Yes, exactly. Then my son spoke, “Yeah, the pizza didn't last very long for me either. I would be hungry again in just a couple hours. I was having to eat again before bed.”

And so we had a mini discussion about nutrition and growing bodies, about how more activity needs more fuel. And they didn't just listen, they asked questions. A little later, at the store, the amount of protein for both of them increased dramatically. Each one came to me with their choices and asked for my opinion. I taught them how to evaluate it against their nutritional needs for the week. Together we collaborated on the best way to avoid exceeding their budget.

I admit, I got a lot of questions from people around me. Cashiers noticed. The good ones praised the kids directly, especially the ones with children themselves. Many of them said “I have to try that with my kids.” And it became something we did for a long time. Both my kids became my grocery buddies rather than coming along simply because they couldn't stay home alone. Years later, when my son was sixteen and living independently he called my husband and told him something I never forgot, “I miss Mom shopping for me. She always knew what I liked. I can't find my soap.” Bottom shelf son; look down (he's 6'2” now).

The lesson I carried into business

Raising my kids taught me lessons about leadership that I would eventually carry into business. One of the most important: no two people are exactly the same or interchangeable. I couldn't force my son to like what my daughter liked or vice versa. And they both learned differently. My daughter is dyslexic and my stepson is autistic, which meant teaching them required being adaptable to each of them individually. So I learned to communicate with them both one-on-one directly but specifically in the ways they needed.

Business leadership isn't actually that different. In the beginning, founders have to do almost everything. They establish the values and guardrails. They build the systems and processes. They make decisions constantly because there isn't anyone else to make them.

But then something changes.

The business becomes more capable.

Founders have to learn to let go too

And the leadership that got it there has to change too.

This is where many founders struggle, justifiably so, in slowly letting go. In recognizing when the business has reached a new level and adapting to that. The entire point of building a healthy organization is to make the founder progressively less necessary to its daily functioning. Initially, the founder should be everywhere. But eventually the organization starts to grow up. And the way you lead must grow with it.

Some founders never learn how to make that transition. They keep making everyone's grocery choices because they know what everybody should buy. But the question to ask is this: is the choice dangerous? Or just different? Can you let someone discover a different answer?

Motherhood taught me that leadership changes as capability grows. And for the last decade, I've found myself helping and teaching founders to make that same transition. You don't stop leading, you adapt how you do it. Eventually, if you've built it right, your role evolves from doer to teacher to manager to coach to advisor. And the founder role doesn't disappear, it naturally rises.

Good leadership means continually giving away the very control you needed in the beginning.

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