Building a Family and a Career: Lessons From My Dad and My Husband

Most weeks, I write for working moms. I discuss the mental load, communicating your value, and balancing career and motherhood. So this Father's Day, I turned the microphone around. I sat down with two of the hardest-working men I know — my dad and my husband — and asked them questions I was genuinely curious about, but also questions I think working parents everywhere in the modern workplace will resonate with.

I asked questions like, what does it take to build a family and a career at once? What would you do differently? What do you wish someone had told you earlier?

I expected tidy answers. I got honest ones, which are always better.

My dad: 35 years of building a business and a family

He ran his own mailing business for most of my life. Here's what he said.

What was Jenna like as a kid that people would be surprised to know now?

He didn't pause: "Fearful. Fearful about everything." (He's not wrong, I used to have a great fear of closed doors, locked doors, elevators, and my parents leaving me at night). 

Then he proceeded to say, “but thanks to Alanis Morrisette, we got over that” 

For all my 90s kids…. The album Jagged Little Pill single handedly describes my experience as a child. 

What is one piece of advice for hard working professionals who are in the trenches?

"Keep pluggin away. it's gonna work out. It's going to take a lot of hard work but it'll work." "Be passionate about what you're doing.” To which I replied skeptically …. "you were passionate about the mailing business?"  We both laughed. And he said, "I was passionate about my own business. Doesn't matter what business it was in."

I think that’s a good nugget for all of us. We don’t have the passionate about WHAT we are doing as long as we are passionate about WHY we are doing it. 

How did you balance your business and family?

"Putting out fires. Whichever is burning brightest takes your attention" 

As a kid, I remember vacations being interrupted because of work events. As a parent, how did you manage? Looking back, would you change anything?

I assumed he'd say no, he wouldn’t change anything. Instead he said, “I would have hired more people to do better coverage. I would have hired differently. Someone that was working 2 days a week and another 3 days a week vs full time employees"

We went back and forth about money because that’s a big business expense… you can't pay people you can't afford. BUT his point landed: he waited too long to build a team around himself, and the cost wasn't the business. The business was fine. The cost was the interrupted vacations, the moments he stepped away, the glass balls that dropped because no one was positioned to catch them.

Our conversation evolved into the state into the job market today because careers today look much different than careers 35 years ago. I ask him, “do you think you could have found good talent back then for a 2 day a week part time position?” He immediately said “no”. 

But in 2026… that narrative has changed. People are looking for that kind of work and companies need that type of employee (seems like that’s been the case for 35 years). 

What's your most underrated parenting advice?

"Let them be kids. Allow them to grow, make mistakes, you can't do it for them” 

To which I replied… “So how did you apply that to me being fearful?” (because I know as a mom now I would do anything to take that fear away from my own daughter)

He said “Pointed out you don't need to be fearful. And played Alanis Morrisette 4,000 times”

*editors note: as we were wrapping up lunch where I was interviewing him, Alanis Morrisette, Right Through You from Jagged Little Pill started playing over the restaurant sound system. 

My husband, Kevin

His questions were different, and his answers were softer. 

What's one thing you think Jenna does really well as a mom that she probably doesn't give herself enough credit for?

“How many hats she wears as a mom. She's engaged with other moms, with the school, with volunteering, with scheduling activities, with making dinner, and being involved in a lot of aspects of the kids lives.”

What do we do well as a couple?

“We compliment each other very well. I have strengths in opposite areas Jenna has strengths.” 

How do you view your work life fitting in with your family life? 

“To me, family always comes first but it's always a tough balance. I wish there could be more of a balance” 

What is one thing you wish all hard working dads heard on a daily basis? 

“That they are making an impact on their children’s lives. I feel like sometimes dads feel like if they are working too much or missing something they miss the point of still providing for them and being an example for work ethic. They are impacting their kids in different ways.”

Thank you to Kevin and my dad for being willing to participate in the work I do at Career Civility by offering your perspective as two hard working men who value family. 

Two men, two generations, one quiet agreement underneath all of it: building a family and a career is a struggle to balance it all for both men and women. My dad’s perspective is from the “other side” now that he is in retirement. My husband is from the perspective of still being “in it” and both of them, in their own words, were describing the same struggle trying to provide for your family while putting the kids first. 

To the hardworking dads reading this, and to everyone holding a job and a family in the same two hands,  Happy Father's Day!