Lessons in Leadership, Learned Through Motherhood

The Takemoto Family

by Rebecca Takemoto, WIN Executive Director

Over the last several days, our marketing team has been speaking with many of the mothers in our organization, and it got me thinking about some of the career lessons I’ve learned through motherhood and through the many different seasons of life.



When I was a young entrepreneur — long before I had kids — I was 100% all in on work. Much to my husband’s dismay, I spent nearly every waking hour focused on my business. At the time, I thought that kind of singular focus was what success required. But looking back now, I can see how detrimental it can be — not just to the business owner, but to the business itself.


Now, having raised four children, I can clearly see how my intense focus kept me from stepping back and looking at the bigger picture. I was so intent on making everything perfect that I lost sight of long-range goals. I prioritized perfection over innovation and rarely gave myself the space to make mistakes, learn, and evolve.

I had my first three children in three years, so you can imagine the chaos that came with such a quickly growing family. Motherhood forced me to let go of many things. I ended relationships with clients who were never the right fit. I gave my staff more freedom to learn, problem-solve, and make decisions on their own. I found myself having more creative conversations and coming up with better ideas — because conversations that happen while you’re walking through the park with your kids or sitting on the sidelines at baseball practice are inherently different from the ones you have while multitasking behind a computer screen.

Motherhood taught me flexibility. The best-laid plans are almost always interrupted when you have toddlers running around or a baby on the way. I learned to think quickly, trust my intuition, and make important decisions without overanalyzing every detail. Most importantly, motherhood taught me to give myself — and the people around me — grace: the space to fail, learn, get back up, and try something new.

On Mother’s Day, I was reminded that this day can hold many different emotions and experiences for women. For some, it is joyful and celebratory. For others, it may bring grief, longing, complexity, or reflection. And for many women, their most meaningful accomplishments and identities may have nothing to do with motherhood at all.

One of the greatest lessons I’ve learned during my time at WIN is that every woman has a unique story — and every story deserves to be honored. Every single day, I meet or hear about women accomplishing extraordinary things, often while navigating immense challenges, responsibilities, and sacrifices. Sometimes motherhood is part of that story, and sometimes it isn’t. But all of us carry complicated lives, meaningful ambitions, and obstacles we are working to overcome — including the ones within ourselves.

To all of you: I celebrate your wins, I stand beside you through your losses, and I am continually inspired by your resilience, talent, and courage. My hope is that the community we are building at WIN can be a meaningful part of your story — whatever that story may look like.

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