Am I Doing Enough? The Fear That Keeps Every Dad Awake at Night

Exploring The Four Areas Where Dads Fear They’re Falling Short—And How to Show Up Anyway

My 4-year-old ran into the bathroom during Thanksgiving break and wouldn’t open the door. We were in a house full of extended family, including four teenagers. When my wife finally convinced him to let us in, he screamed “They were laughing at me!” He had this look of shame that was hard to forget. He was talking about the teenage boys, and while their laughter wasn’t directed at him, he perceived it that way. The way he internalized it and hid in the bathroom, gave me eerie premonitions of a painful teen life.

I know moments of embarrassment and even harassment are unavoidable, and I want my boys to be resilient and prepared. But the look of hurt was so scary to me as a dad. It made me reconsider if I was truly setting up my boys to thrive in all the ways that mattered most.

Am I doing enough?

It’s a question that keeps many of us Ambitious Dads awake at night. It can feel overwhelming to even consider this question. How do we really know if we setting them up for success? And while our definitions of success are deeply personal, this fear is truly universal.

The Four Pillars of Success

When it comes to (not) doing enough, there were four areas of success that the Ambitious Dads I interviewed focused on: financial, emotional, educational, and role modeling.

Financial Success: Will my kids have the resources they need to pursue their dreams?

The seismic shift in the workplace roles of men and women hasn’t lessened the cultural pressure most fathers feel to be the breadwinners for their families. This weight feels heavier now because we strive to be equally involved at home. According to the Boston College Center for Work and Family, more than three quarters of fathers want to equally share in parenting responsibilities.

College, healthcare, summer camps, tutors, babysitters, sports teams, and extracurriculars—the list of expenses required to prepare our kids for the future feels endless. Beyond creating wealth, Ambitious Dads are focused on teaching the value of money. One of the best practices CEO Jesus Gerena shared with me was this: “spend, save, give.” Create three jars, and every time your child receives or earns money, particularly from a very young age, have them divide it equally between these jars.

Another key insight comes from Harvard’s multigenerational study, which found a strong connection between household chores and later professional success. Chores teach responsibility, teamwork, and an understanding of family contribution. And by offering an allowance as part of it, we can introduce financial responsibility, too.

Emotional Success: Am I raising a child who can handle life’s challenges with grace and resilience?

When it comes to emotional success, one of the most critical and basic factors is to be sure that social and emotional skills are being taught in our children’s classes. More and more, school programs are focusing on teaching kids to identify and express different emotions, develop empathy, and practice active listening. Some also incorporate mindfulness and self-regulation strategies to help students manage stress and build resilience. We need to be aware of whether the schools we send our kids to are not offering this.

Regardless of what’s taught in schools, the language and dialogue around emotions needs to extend into our homes. Many of the Ambitious Dads I spoke with focus on positive self-talk. Words like “It’s impossible” or “I can’t” are banned, and in their place, phrases like “Can you help me?” are encouraged when frustration arises.

The power of positive self-talk is undeniable. Stress expert Kelly McGonigal highlights studies showing that when people are told “You’re the kind of person whose performance improves under pressure,” their actual performance improves by as much as 33%, regardless if the feedback is accurate. And it all starts with us modeling this type of self-talk.

Educational Success: Am I pushing too hard or not hard enough?

As the world spins faster, it’s clear our children need a strong education to keep up. However, education is no longer just about grades; it’s about fostering lifelong curiosity and learning.

One Ambitious Dad noted, “I’m trying hard to foster curiosity over perfection.” This mindset helps kids find joy in learning rather than fear failure. Another dad, a Director of Technology, shared, “I’m struggling to define the goal around success—is it short-term happiness or a longer-term focus on academics?”

The balance is tough. Where do we draw the line between academic excellence and deepening stress? Ambitious Dad Asheesh Advani has written a book that focused on it, titled Modern Achievement, the focus is about the journey as much (if not more) than the achievement destination. (Full disclosure, I’ve co-authored the corporate facilitator’s guide for the book).

Role Modeling: What if I pass on my flaws and don’t live up to the example I want to set?

“The biggest thing stressing me out is my inability to manage my emotions,” confessed a world-renowned CEO coach. One McKinsey dad put it plainly, “I see that when I get angry my son copies it immediately.”

Nothing will impact this fear more than how we model our behavior in front of our children. I’ve written extensively about this challenge here.

Recently, I saw the fruits of my own efforts during my oldest son’s parent-teacher conference. His teacher shared that whenever he has a disagreement in class, he goes out of his way to apologize and repair afterwards. This brought a huge smile to my face because we focus on “repair” extensively in our house. Whenever I lose my cool—or my children do—we always follow up, explain what went wrong, and apologize. It’s rubbing off!

Overwhelmed yet?

Yes, there is a lot of fear to go around. And without a doubt, we can always do more. But here’s the good news: we don’t have to do it all at once. Our children don’t need “more.” It’s our presence and intentionality that matter most.

So maybe our call to action is merely this: take one small step today. Whether it’s having a heartfelt conversation, modeling mindfulness, or designing your ‘save, spend, and give’ jars, every small action builds the foundation for success.