Bill D'Alessandro

4 things I wish I would’ve known about running a business with small children

Published 5 months ago • 4 min read

I’m writing this from my new baby’s bedside as my wife sleeps - our third child was born a few days ago! Everyone is healthy and doing great, and now we are a family of five.

My son is 4 and my daughter is 2.5, so I’m a few years into my journey as “dad”. So today, I want to talk about - how do you run a business while also raising young children?

I admit there’s not a one-size-fits-all answer, but this is a topic I think about all the time — and something that’s generally under-discussed among entrepreneurs.

Here’s 4 things I wish I would’ve known about running a business while raising a young family:

1. You don’t know what you don’t know

If you’ve seen The Matrix, you remember the scene where Morpehous tells Neo, “No one can be told what the Matrix is. You have to see it for yourself.”

Having kids is exactly that. It’s your own personal singularity.

I remember how obnoxious this whole notion of “You won’t know what it’s like until you have kids” sounded before I started my family. But it’s very true - even if you intellectually know what parents are going through, it’s very hard to truly understand as a pre-parent.

Online, it feels like there’s this mass view into these influencers who have morning routines and perfectly optimized sleep — but I now can tell you now, these people are not parents. My morning routine involves getting every minute of sleep I can before my son explodes through our bedroom door, attempts to shower with me, and insists I come downstairs for breakfast. I then get to spend some high quality time with my kids before I head off to work. It’s wonderful in it’s own way, but I assure you there is no meditation, skincare routine, or early morning exercise.

2. You need an office

I know we’re in the age of work-from-home, and it’s great for many people. For me, the pandemic was especially tough. When I work from home and my children know I’m in the other room, it sucks to be “at work” — especially when I hear my son in the next room clamoring to spend time with me. I was suddenly trapped in my home office - desperately wanting to come out and see the kids, but knowing if I did it would throw them (and me) off their routine.

Before kids, working from home was awesome. After kids, I realized I had to get into the office. Personally, my life is much better this way. My kids, my wife, and I all get the structure we need in our days when dad leaves for work, focuses during the day, and comes home for dinner.

Plus, I get the classic “dad’s home from work” celebration Monday through Friday, without fail. Nothing feels better than that.

3. You aren’t a bad parent if you’re not 100% indexed on your family

Before I had kids, I felt like there was plenty of time for everything - my company, my wife, and myself.

Then the kids showed up. And as all parents know, it usually feels like “work, wife, kids, self - pick 3”. James Clear calls this the “Four Burners Theory”.

I have an awesome relationship with my dad. When I told him I was struggling to balance all four of my burners, he told me that when my siblings and I were young, he was all-in at work as a surgeon. He left early and came home late, and I remember knowing he was busting his butt to build a life for our family.

I don’t remember being sad he wasn’t there. I only remember being happy when he came home. And he was always there for all the stuff that mattered - game days, plays, and family dinners. In fact, one of my favorite things to do was go with him to visit his patients at the “popsicle hospital” sometimes on Saturdays - I got to meet them all and watch him do his job, then get a popsicle from the surgeon’s lounge at the end. It was a great way for him to blend his family with his work.

Time is a balance you can play with. But understanding it is a balance helped me get some perspective from the cultural pressure that you have to be 100 percent in on family every single day or you’re a bad parent.

4. Your kids probably won’t be entrepreneurs

Not only is entrepreneurship not for everyone, it’s not for most people.

I’ve hired countless people, coached many entrepreneurs, and have had incredible highs and lows over the past decade of being an entrepreneur. I’ve got the gray hairs to prove it.

Sure, your kids have your genes — but it’s most likely they won’t pursue their own business.

Instead, I’ve found it to be much more rewarding to teach my kids how business works. Not only does it make them a better employee for someone else, it helps them understand what’s going on in the world around them. I try to help them understand money, incentives, decision-making… the list goes on.

If they want to know more, I’ll teach them. I won’t push them or set them up to take over my business.

If you have kids, what’s your biggest lesson about being an entrepreneur and a parent? Let me know and I’ll share a few examples in an upcoming newsletter.

If you liked this newsletter, I have 4 places where I share more like it:

  1. 👔 The 1-1 coaching that I do with CEOs (I currently have ONE slot open).
  2. 🐦 I tweet (a lot) - follow me @BillDA.
  3. 🎙️ My podcast, Acquisitions Anonymous, where we break down real businesses that are for sale.
  4. 📬 This weekly newsletter! Click here to subscribe and read past issues.

Until next time,
Bill D'Alessandro

Bill D'Alessandro

I've been an entrepreneur my whole life - now I coach others.

Join my newsletter and I'll send you non-public stories, tales from the ecommerce trenches, and even opportunities to invest in private deals with me.

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