The mantle of becoming CxO (part 1)
The ambition a baby unlocks
There’s one thing that’s changed tremendously in my life since 4.5 years ago…
We’re no longer a one-kid house!
This year we welcomed another baby girl into our home, and here was the biggest surprise:
My ambition level DIDN’T CHANGE ONE BIT.
If anything it rose - inspiring me to map out my goals for the next decade.
How does this transformation happen, you ask?
By three things:
- Constraints force creativity.
- Challenge raises energy.
- Love enables grit.
Urgency is a luxury of your early 20’s.
Early in our career we can use this feeling to bludgeon our to-do list and power through low motivation.
There usually aren’t family members who depend on you waiting at home, whose needs would clash with your goal-oriented urgency.
As responsibilities and family grows, we have less time and space and more problems to solve, for a smaller set of high priority people and things.
That’s the winning recipe for more creativity, energy, and grit.
The key is to first pop out of “work mode” when shifting contexts. Relationships need us to let go of control rather than apply it. Open listening is much more important at home than executive actions or analysis.
There’s one group of people who illustrate this dance so well: the entrepreneurs building both their young companies and families at the same time.
For this article I talked about ambition, entrepreneurship, and family with Bryan Wang and Cait Larson, who are the cofounders and CEO/COO respectively of Boswell. Boswell is a new healthcare company that pairs software and data with community health services to drive care for the patients who need it most.
Me: What, if anything, has changed about how you view work-life integration and your ambitions?
Bryan: Early in my career, my ambition was based on impatience. Specifically, trying to “get ahead” – whether through a good school or a prestigious job. Before kids, I had a pretty standard 9-to-6 workday, followed by a few hours off, and then back to work until late into the night. Now, my schedule revolves around my family. My priorities have evolved. I think about gender roles and being a very involved dad.
My ambition has shifted more to what I really want to accomplish, as independent from external benchmarks as possible. I went into healthcare to learn more about the industry and to make a true positive impact on the world.
Now that I have a kid, my ambition also includes wanting to be the best parent I could be. I see my career ambitions on a longer time horizon. But I don’t think the degree of my ambition has changed much.
Me: And how about you, Cait?
Cait: Parenthood has been a huge mindset shift for me. I’ve been an athlete my whole life, was a full scholarship athlete in college. I’ve always wanted to win. Like Bryan, my ambition hasn't changed, but it's spread more laterally now, across the landscape of what I care about.
Now, some of my drive also fuels lessons about kindness and sharing for my kids. I'm still passionate about my work, but I've learned to prioritize and give myself grace. It's about finding a sustainable pace.
For example, if I'm struggling I ask myself, can I change my mindset to make this easier?
I used to push myself to the limit, working incredibly long hours. I’m wiser now. A lot smarter now. One of the best skills I’ve developed is knowing which balls I’m juggling are plastic, and which are glass. I can confidently set things aside - turn things off in my brain.
Me: Do you have any tactical suggestions for the daily juggle?
Bryan: I wake up early to give my wife some extra sleep, work a focused 9-to-5, dedicate time in the evening to my child, and log back in to finish up after her bedtime. It's definitely a challenge to be efficient, but I've also been able to be more focused during work hours. Sometimes balance also means I strap my kid to myself while doing admin tasks!
Cait: At home, be present. When you're with your kids, give them your full attention. There’s a common saying that’s so true - “Nobody remembers the extra hours you work except your kids”. Also, don't be afraid to be vulnerable with your team if you’re struggling with a personal issue. It might seem counterintuitive as a leader, but sharing your struggles can actually strengthen your leadership and build trust. People see you as more human and relatable.
Me: What's one message you want to give to founders who value family and aspire to build high-growth startups?
Bryan: Of course, there will always be the question of whether early-stage high growth entrepreneurship is compatible with early parenthood. On one hand, I do have more flexibility and control over my own schedule compared to working for someone else; but on the other hand, you are still going to be working a ton, which takes time away from being present as a parent.
So I want to say, make sure you have a good support system – both for childcare and financially.
Cait: I do think it's possible to have both. Remember, your kids are learning from you. Kids can pick up from what we say the best parts of our work, and the challenges they should be thoughtful about as they grow and come into the world. As parents we can help them understand a journey of emotional highs and lows too. By showing them our passion for our work while being committed to the family, we're setting a powerful example.
Also, founders care so much about their company. Becoming a parent helps us help our people even better. I know the value of our people even more deeply, and take the time to really develop trust with them.
Clearly, for both Bryan and Cait, their level of ambition hasn’t changed. Like me, if anything, they have a chip on their shoulder to prove the world wrong - that a richer personal life can fuel even more professional ambition.
This is the first article in the series “The Mantle of Becoming CxO”, where we discuss mindsets, tactics, vision, and the motivation of startup leaders who lead their lives and companies with equal passion.
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Boswell bridges gaps in care for U.S. Medicaid members by serving as the trusted technology and wraparound service partner for food pantries, social service organizations, and Medicaid health organizations. By pairing software and data insights with community health worker services, Boswell drives engagement, better health outcomes, and lowers costs of care.