How to Parent

The title above is misleading because it implies I’ve figured parenting out, which I most definitely have not. But Father’s Day is coming up and we’ve been doing this “how to” series of posts over the last few months, so we thought this would be an interesting subject. 

I’ve been a parent for about 18 years (33 collectively if you combine both kids). I’ve gotten some things right. I’ve made plenty of mistakes. I know that I love my kids and they love me. I know they’re good kids. They’re generally happy and healthy. I’m very grateful for them. 

Below is some of what I’ve learned, mostly from trial and error. If you’re a new parent, you’ll probably still make most of the same mistakes I did, but hopefully at least seeing it here first will make you feel a little less bad as you make them.

(1). Life is not linear.

Your kids will do well at times. And then they’ll struggle. Then they’ll bounce back. Then they’ll struggle again. Of course we only want good things for our kids at all times but they’re human beings. You can’t create a world where nothing bad ever happens. You can create a world where they know they are loved unconditionally and can come to you for support at any time.

(2). Most of the things you’ll worry about are not that big a deal.

In my opinion, where they go to preschool doesn’t matter. Where they go to high school doesn’t matter. Where they go to college doesn’t matter. What they get on a standardized test or whether they make the varsity team or whether they’re the lead in the school play doesn’t matter. 

To me, all that matters is that they hopefully find things they enjoy and are good at and can ultimately make a living doing some version of it. Not only is that not correlated to the prestige of the school you attend, arguably, the correlation is inverted because the prestige often pushes you in directions that sound good but very well may make you absolutely miserable. 

Spending a career as an investment banker or corporate lawyer or management consultant may be the last thing that will actually make you happy. When I was finishing law school, my parents couldn’t understand how I could turn down high paying jobs at law firms to make $36,000 at the Parks Department. Luckily, I ignored them. 

At the same time, make sure your kids understand that anything worth achieving only happens from a lot of work and a lot of sacrifice. No one hands you anything and even if they do, you’re never going to feel truly good about yourself if that’s how you made it. Better to have less but have it be your own. 

My kids will never go hungry, but my goal in life is not to leave them with generational wealth. That doesn’t really help them and it definitely doesn’t help anyone else. The goal is to use the money I make to try to impact the world in ways that are meaningful to me (and hopefully to them). I think demonstrating that to my kids is far more valuable than the cash. 

(3). Your kids are independent human beings.

Accept them for who they are. Of course you should teach them values and of course you should provide them with structure and discipline. But trying to mold them into something specific is only going to make them hate you. Your ambitions, your needs, your insecurities are yours. They have their own. Let them be whoever they are and love them for that. Full stop. 

When my son was little, it was important to me that he know how to defend himself, so I signed him up for boxing. He had a good attitude but never really loved it. The gym closed when covid hit and he started playing golf. I’ve never played golf (although I did get a hole in one once in mini golf; right through the windmill). It’s not my thing. But he loves it and now we have a golf net in the living room. 

(4). Show your kids that you’re human.

Yes, when they’re really little, they will idealize you and think that you’re perfect. And yes, when they’re teenagers, they’ll probably hate you and think you’re a moron. Those are phases. 

Overall, they need to understand that we all have strengths and we all have weaknesses. We all succeed naturally at some things and struggle with others. It’s okay if they’re not a great student or athlete or artist. It’s okay if they’re not popular or dynamic or charismatic. And the best way to show them that is to demonstrate your own humanity. Own your mistakes. Admit to them. Explain what is challenging for you. The more they realize that you’re human and fallible — that you’re accountable for it and have a sense of humor about it — and it’s still okay, the more they’ll develop their own self compassion (which then makes them more compassionate towards others). 

For example, I quit smoking weed about a year ago. I told my kids that I did and I explained that because it had become so ubiquitous in New York, I was struggling to use it in moderation and decided that quitting altogether was the better approach. They understood that and they also understand that like me, they may have addictive personalities. I think my admission, difficult as it was, has helped them – and will continue to help them – navigate their own experimentation. I’m glad I did it. 

(5). Put in the time.

Not every moment is special. Some are miserable. Many are boring and wholly unmemorable. But the more reps you get, the better you get at parenting. And the more you’re there, the more you’re there. That’s what they want – to know you’re around and available to support them if they need it. My kids are teenagers now and there are nights where I physically see them for all of twenty minutes even though we’re in the same apartment. That’s okay. They know they can yell out “dad” at any time and I’m there. 

(6). Show don’t tell.

This is usually the advice you get in writing classes but I think it’s equally true with parenting. If you want your kids to develop good values, they need to see that you have good values. If you tell them that helping other people is important, they need to see you actually volunteering and giving away money (enough to hurt) and going out of your way to help others. If you tell them that respect is important, they need to see you show respect to everyone you interact with (especially those in a service capacity). If you tell them that exercise is important, they need to see that you exercise. If you tell them that reading is important, they need to see that you read. If you tell them not to be judgmental, then they can’t see you constantly passing judgment on others. If you tell them that family is important, they need to see you have good relationships with your parents or siblings or whomever. If you teach them that kindness and empathy is important, make sure they see you showing kindness and empathy to others in real, tangible ways (not just the words coming out of your mouth). If you want them to embrace new experiences, embrace the things that excite them too (even if it means listening to a lot of drill music). If you don’t want them to constantly complain and feel sorry for themselves, don’t make yourself a victim either. If you don’t want them to be hooked on social media, don’t spend all of your time on Instagram. They learn from watching you so the better you are, the better they’ll be.

(7). Make sure they know you’re in their corner.

I was bullied my entire childhood and my parents didn’t really know how to handle it. I’ve experienced minor versions of that with my kids, and while there’s generally no single right answer (my instinct to go burn down the bully’s home is definitely the wrong one), if they see that you are there, you’re standing up for them, you’re talking to the school, you’re talking to the other parents (even if it embarrasses them, even if they beg you not to), then they know you’re in their corner. That is essential. 

(8). Teach them it’s okay to fail.

I make mistakes all of the time. I take risks professionally that don’t pan out. I start companies that fail. I support candidates who lose. I write books that don’t sell particularly well. Not that many people will read this column. I never enjoy failing, but trying new, difficult things is the only way to ever achieve anything meaningful. 

I try to make sure my kids see that. Of course I want them to know when I succeed, but it’s probably equally important – if not more so – for them to see when I fail, how I handle it, what I learn from it, and that I keep going and keep trying new things. If I accept responsibility for my own choices and my own failures, they will learn to do the same and that ultimately improves their ability to manage negative emotions, which means they’ll be happier. 

Perhaps even more important, teach them that life is not all bliss all of the time. It’s not even supposed to be. If they grow up thinking that’s the baseline, they’re always going to feel disappointed and they’re likely going to think there’s something wrong with them. Life is great. And life is hard. Usually at the same time. That’s okay. The goal is to find sustainable peace and contentment and happiness within that dynamic. 

(9). You’re going to make a lot of parenting mistakes.

No one bats 1.000 as a parent. The good news about parenting is there are lots of at bats. You usually get another one literally the next minute after you mess something up. Just hang in there and keep going. And when you mess up, take accountability. Apologize to your kids. Let them know how you should have handled it differently and how you will handle it differently in the future. That’s how they learn the exact same thing. 

(10). Teach them where happiness comes from.

Yes, there are basics – health and stability and freedom and safety, a place to live, food to eat – that are essential. But beyond that, your kids’ happiness is not going to come from more and more status and more and more money. Those things can be nice but all research shows that happiness really comes from two things: meaningful relationships and a sense of fulfillment. 

Good relationships mean finding people you like and trust and feel safe with. It doesn’t matter if it’s family or friends or colleagues or classmates or neighbors or anything else. It’s just important to have them. Fulfillment can come from your work, your volunteer activities, your hobbies, your family, your faith. But it means feeling good about something you do and then enjoying the contentment it brings. Living without it, or just tying it to external markers of success, is a recipe for misery. Make sure they understand this and model it for them as best you can. Over and over and over again. 

Being a parent is wonderful. Being a parent is difficult. I’ve done the best I can raising my daughter and my son. I have gotten some things right and I’ve gotten plenty of things wrong. But I know this: I love who they are. I love who they have become. I love being their dad. And I can’t wait to see what comes next.