15

My daughters turn 15 tomorrow.

It seemed just a moment ago when my wife and I were in Morristown Memorial welcoming Annie and Lily to the world.

On August 26, 2010 they were born – and in a week, high school begins.

Here are fifteen lessons I have learned from fifteen years of parenting that I think could apply well to any area of life:

1. Expect Surprises!

Since I come from a family of boys on my side of the family, we assumed we would be having twin boys. It was a foregone conclusion. Dara and I fought over boys’ names; my votes were Rocco and Max, but she wasn’t having it. We barely thought about girls’ names. 

At approximately 7:05 AM on August 26th, we were thrown for a loop when the doctor said, “The first one is a girl!” 

I thought, “Wow! We’re going to have a boy and a girl!” 

A minute later, he said, “The second one is a girl.” Dara and I looked and each other and just burst out laughing in shock.

It was the first of many surprises along the parenting journey!

2. You Get Out of It What You Put into It

Parenting is a lot of work, but I think it is the most important job in the world. 

The rewards are delayed – especially at the beginning, when the first year plus you are raising little animals who eat, sleep, go to the bathroom, and cry. 

Over time, there is a compounding effect to the time, energy, and effort you spend that only grows each day – or withers – depending on your daily investment.

It’s the ultimate reminder that relationships are dynamic, not static. Moments are earned - not products of entitlement!

3. Every Day Brings a New Challenge

When I was a younger parent, I used to focus on clearing the challenges ahead, not knowing there was another one around the corner. 

First it was, “Once they sleep through the night, life will be easier.” Months later, it was “Once they are done teething, life will be easier.” 

A few years later, my thought was, “Once they are out of diapers, life will be easier.” At some point, you simply realize that the challenges are ongoing. 

As Alex Hormozi, author of $100M Offers, $100M Leads, and now $100M Money Models says, “You’re always solving problems – you’re just solving a more elegant problem with each stage.” 

When I think about parenting, that statement is incredibly on the mark!

4. Sometimes there are messy clean-ups.

I think this one goes without saying – especially in the early years!

Although after a sleepover this weekend, in cleaning up the popcorn, pretzels, and candy from the loft - perhaps this lesson endures!

5. Tomorrow is Another Day

You learn pretty quickly that you are going to have plenty of imperfect days as a parent.

I bat about 10% in trying to find the right words, and sometimes, I wind up being the “Bad Dad.”

Cherish the rare perfect days, but know those are few and far between.

6. Remember that you can do it alone - but you don’t have to. 

It takes a village to raise kids.

This summer with two different pre-season sports schedules, I feel like I need to update my LinkedIn profile to part-time chauffeur - and I did maybe half of it! 

Your village can be family, friends, online resources – it doesn’t matter where you turn, but put your ego aside and ask for help. Ask for help a lot.

7. Shortcuts Bite you in the Ass

Sometimes we get in spots where we are juggling too much and we end up cutting a corner. If that happens, you’re human. Just be careful not to make a habit of it. 

If you need some quiet, and simply assume everything is all right just because your kids are quiet in their room or scrolling their phones, you may be in for an unpleasant surprise. 

I see infants with Ipads at restaurants and every car ride to the grocery store wherever I turn. This might make for a quiet car and dinner table. When they are 9 years old tuning parents out until they go to college and parents wonder why – it won't be a mystery!

8. You’re not Going to Win every Discussion

I’m competitive, and sometimes, I’m also a slow learner.

Living in a house where I am outnumbered three to one, I have learned that as much as I enjoy winning a discussion, there are many times I simply won’t!

Footnote: Since 2023, with Gus (my male golden retriever), it is nice to have someone who doesn’t verbally challenge me! 

9. Expect to be Humbled Often

Building on Lesson #3 of expecting new challenges… 

After those parenting “wins,” it’s easy to think you’ve got it all figured out. 

Just yesterday I resolved a conflict with one of my daughters and felt so great about the conversation, thinking I had solved it for good. 

Today I was humbled by having the exact same conflict, and it was five times more confrontational. Back to the drawing board.

Parenting is humbling. Appreciate the victories, but be prepared to lick your wounds and try again.

10. Staying in the Present is Key

Life is a series of moments. It’s key to look forward to things and to plan for the future, but be in the moment, or you’ll miss what’s important. 

It’s the little things like a family walk, cooking breakfast together, and even doing errands and chores together that add up to an amazing life!

11. Spend 1:1 Time

This is especially for all the twin parents out there.

For so much of Annie and Lily’s life, they have done things together. Same extra-curriculars, same friends, same camps. As a family, it’s easy and convenient to keep all of us together.

What’s important to realize is they are their own person. Finding the opportunities to spend 1:1 time - in whatever way that is meaningful - is crucial to relationships.

Annie likes to write, so I try to find opportunities to read her stuff and review it with her. Lily has gotten back into cooking after a couple year hiatus, and interestingly enough, she loves going to the grocery store with me each week. 

While these may not be my choice of activities, I feel blessed that at 15 they still want to spend time with me!

12. Honor the Struggle!

Being a parent is the hardest, and most important job there is. Nothing comes close.

All of us screw up a million times, and we try to do our best the next day to do it better. If you look at it through that lens, you will have a healthy appreciation for the work required, give yourself some grace, and value the experience.

13. It’s the Journey, not the Destination

Yes – there are milestone wins along the way, but the process itself is where the magic really helps. 

Like Ferris Bueller once said, “Life moves pretty fast. If you don’t stop and look around once in awhile, you may miss it!”

With just four years before college, that realization is starting to manifest itself, giving me more awareness to make the moments count.

14. Let them Fight their Own Battles

As the girls get older, it’s a continued discipline to let them fight their own battles.

The temptation as a parent is to shield your kids from heartache. When they feel pain, you feel pain.

In those moments, it’s important to remember that life is struggle. It’s not all cupcakes and rainbows. The tough moments are opportunities to learn - to overcome adversity, to adapt, and sometimes, to simply experience something uncomfortable.

Each experience is a chance to grow and realize life moves on, and it’s your role to be by their side - not solve their problems.

Helping your kids learn to advocate for themselves is one of the best gifts you can give them.  

15. It gets better every year!

When my girls were born, my friend and former Pingry colleague Ananya Chatterji gave me the most sage parenting wisdom I’ve ever heard. It has endured the test of time.

“Every time you think it can’t get better – it does!” 

I have felt that every year. Each year has been a different blessing with its own character, and I’ve enjoyed them all. 

Of course – she also said this had a part two – “...until they are teenagers – and then you want to give them back!” 

While middle school had its ups and downs, it has all been worth it.

Annie and Lily, here’s to hoping 15 is an even better year in the wild ride of life.

Happy Birthday! We love you!!!

#family