Issue 002
Comfortable Being Uncomfortable
My son is five.
And lately I've been thinking a lot about something that I'm not sure has a clean answer.
How do you make your kid feel completely safe without making his life too safe?
I want Nikko to know, without question, that he's loved.
That his mom and dad have his back.
That there's a place he can always come home to.
I hug him constantly. I tell him I love him. I want him to grow up with a kind of emotional security that wasn't necessarily common for men of my generation.
But at the same time, I don't want to protect him from every difficult thing.
Because I'm not sure that's actually protecting him.
Life is going to be uncomfortable.
He's going to lose.
He's going to fail.
Somebody is going to be better than him.
He's going to get his heart broken.
He's going to try something he sucks at.
He's going to be scared.
And eventually he's going to face things Melissa and I can't fix for him.
So maybe part of my job isn't preparing the road for my son.
Maybe it's preparing my son for the road.
What we inherit
I've thought about this a lot through the men in my own family.
My grandfather died when my father was thirteen.
My dad grew up in the Bronx and had to become independent pretty damn quickly.
By the time I came along, I think a lot of his understanding of being a good father was tied to providing.
You worked.
You took care of your family.
You made sure there was food on the table and a roof over everyone's head.
That was love.
There weren't a lot of hugs.
There wasn't a lot of talking about feelings.
In fact, I don't think I remember my dad telling me he loved me until I was in my forties.
But I never doubted that he did.
I knew it because of what he did.
As I got older, though, something changed for me.
My dad was getting into his seventies. He'd had heart issues. And I was very aware that his own father had died when he was only thirteen.
I started thinking about time differently.
And somewhere along the way, I decided I never wanted to walk away from my father wondering whether he knew how I felt about him.
So every time I saw him, I'd make a point of saying it.
“Hey, Pops. I love you.”
My dad was a Bronx guy. This wasn't exactly his natural language.
His response, in that thick Bronx accent of his, was usually:
“You too, kid.”
That was Dad.
And I knew exactly what he meant.
Maybe that's part of why I'm so deliberate about saying it to Nikko now.
I don't want him to have to translate it.
I want him to know it through what I do, the way I knew it with my father.
But I want him to hear the words too.
And some of the things I inherited from him have served me incredibly well.
Independence.
Resourcefulness.
A willingness to figure shit out.
The belief that if something needs to be done, you probably shouldn't sit around waiting for somebody else to do it.
But every generation gets to decide what it wants to carry forward and what it wants to do differently.
With Nikko, I want both.
I want him to have the security.
The hugs.
The words.
The certainty that:
You're loved.
You're safe.
I've got you.
But I also want him to hear:
You're capable.
Try it.
Do the hard thing.
Get knocked down.
Come back.
Those things don't seem contradictory to me anymore.
I'm starting to think they actually belong together.
You go first
I knew pretty early that I wanted Nikko to do Brazilian jiu-jitsu.
Not because I want him growing up looking for fights.
Almost the opposite.
I wanted the athleticism. The dexterity. The confidence. The discipline. The experience of doing something difficult and slowly getting better at it.
And I wanted him to be able to travel the world someday with confidence.
To know that he can take care of himself.
There's something about knowing you can defend yourself that, hopefully, means you don't feel the need to prove that you can.
You don't need to walk around with a chip on your shoulder.
You don't need to be the toughest guy in the room.
You just know something about yourself.
But there was another part of the decision that mattered to me.
If I was going to ask my son to do something hard, I wanted him to see that I was willing to do something hard too.
So when Nikko signed up for jiu-jitsu, I signed up too.
I was 57.
We couldn't train at the same academy at first because the schedules didn't work. Nikko was training in Aguadilla and I started training in Rincón.
But we were both beginners.
Both putting on a gi.
Both walking onto a mat where we didn't know what the hell we were doing.
Both learning.
And I liked that.
Because I don't want to stand on the sidelines of my son's life telling him:
Be brave.
Try hard things.
Don't quit.
Get back up.
While making sure I never have to experience any of those things myself.
Sometimes the best way to teach something is to go first.
About six months later, the academy in Rincón started building out a class for kids his age. Eventually we were able to move Nikko over.
Now, about a year after we started, we're finally training at the same place.
Same academy.
Same coaches.
And I fucking love it.
The guys I'm rolling with—the guys tapping me out and kicking my ass—are some of the same guys helping my five-year-old son learn.
I'll finish training and one of them might tell me how Nikko is doing.
Where he's improving.
Something he did well.
Something they're working on with him.
There's something deeply satisfying about that.
We're obviously at completely different places in our lives.
He's five.
I'm 58.
But in this one little corner of our lives, we're both students.
Both learning how to be uncomfortable.
Both learning how to lose.
Both learning how to come back.
And maybe someday he won't remember that his dad started jiu-jitsu at 57.
But I hope some part of the lesson sticks:
I'm not going to ask you to do the hard thing while I stand safely on the sidelines.
Getting your ass kicked
There's something beautifully honest about jiu-jitsu.
The mat doesn't really care who you think you are.
You can be successful in business.
You can have money.
You can be older.
You can have an impressive title.
None of it helps much when somebody has your arm in a kimura behind your back and you have no fucking idea how to get it out.
Tap.
Hand slap.
Fist bump.
Start again.
That's humbling.
And humility is uncomfortable.
But I think there's something healthy about voluntarily putting yourself in situations where you're not in control.
Where you don't know everything.
Where you're going to fail in front of other people.
Where progress happens slowly enough that you can't bullshit yourself about it.
Nikko gets versions of that too.
He loses.
He gets frustrated.
Sometimes he doesn't want to do something.
Sometimes something scares him.
My instinct as his father is often to make the discomfort disappear.
But I'm trying to catch myself.
Because discomfort isn't always a problem that needs solving.
Sometimes it's the actual lesson.
The confidence problem
I think we sometimes misunderstand confidence.
We try to give it to kids.
You're amazing.
You're so smart.
You're the best.
And there's nothing wrong with encouraging your kid.
But I'm not sure confidence can really be given.
I think it has to be accumulated.
You do something you didn't think you could do.
You struggle.
You figure something out.
You fail.
You try again.
Eventually your brain starts collecting evidence.
I've been here before.
I didn't know what to do then either.
I figured it out.
Maybe I can figure this out too.
That's confidence.
Not the belief that everything will go your way.
The belief that you'll probably be okay when it doesn't.
And I'm trying to teach Nikko that failing isn't the opposite of getting better.
It's part of getting better.
We used to say something similar in business all the time:
Fail early. Fail often.
Not because failing is the goal.
Because failure gives you information.
That didn't work.
Okay.
What did I learn?
What can I do differently?
Try again.
Get a little better.
Nikko doesn't always see it that way yet.
He's a little bit of a perfectionist. When he can't do something the way he wants to do it, he gets pissed.
And I recognize it immediately because I was the same kid.
I played competitive tennis and had a little bit of a McEnroe temper. I'd get pissed off and throw my racket when things weren't going the way I thought they should.
So now I'll watch Nikko getting frustrated with himself and sometimes I have to laugh.
There I am.
Just five years old again.
And what I'm trying to give him in those moments isn't the answer.
It's the space to keep trying.
Take your time.
It's okay.
Do it again.
Nobody's judging you.
Because most of the time, Melissa and I aren't judging him at all.
The person putting all that pressure on Nikko is Nikko.
Maybe part of my job is helping him learn early what took me a lot longer to understand:
You can fail at something without being a failure.
You can screw it up.
You can lose.
You can be terrible at something the first ten times you try it.
None of that says anything permanent about who you are.
It just tells you where you are right now.
Then:
Hand slap.
Fist bump.
Start again.
And if I remove every obstacle from Nikko's path because I love him, I might accidentally remove some of the experiences that teach him that.
That's a hard thing for a parent to sit with.
The world gets bigger
My father was a fisherman.
Some of my earliest memories of curiosity came from the water and from watching things like Jacques Cousteau and National Geographic.
There was this enormous world out there.
Oceans.
Animals.
Boats.
People living completely differently from us.
I wanted to see it.
I think that curiosity shaped a lot of my life.
And Melissa and I are trying, consciously or not, to expose Nikko to the same idea.
Not necessarily the same things.
But the idea that the world is big.
We live around the ocean.
His mom is a yoga teacher and a freediver.
We surf.
We paddle.
We snorkel.
We watch nature documentaries and science and people doing things that seem almost impossible.
Sometimes we'll watch parkour or some crazy Red Bull video and Nikko's eyes get huge.
I love that.
Because before you voluntarily do hard things, you have to imagine that something interesting might exist on the other side of them.
And that's something I'm trying to help him understand, even if he's probably too young for me to explain it this way yet:
Where there's discomfort, there's often opportunity.
Not always.
Fear exists for a reason. Sometimes being scared is your brain telling you, Don't do that stupid shit.
But sometimes fear is simply telling you:
I've never been here before.
I don't know if I can do this.
And I've learned that those moments are worth paying attention to.
The waves look a little bigger than you're used to.
You're walking into a new school where you don't know anybody.
You're trying something and you're afraid you're going to suck at it.
Part of you wants to turn around and go back to what's familiar.
And maybe sometimes that's exactly what you should do.
But sometimes there's another question worth asking:
What's on the other side of this?
Maybe you paddle out and realize you can handle a wave that scared you from shore.
Maybe you walk into the new school scared and eventually make a friend.
Maybe you try the thing you're terrible at and discover something you love.
Maybe nothing dramatic happens at all.
But your world gets a little bigger.
That's what I want Nikko to begin recognizing.
Being scared doesn't mean you're weak.
And being uncomfortable doesn't necessarily mean you're going the wrong way.
Sometimes it's the opposite.
Sometimes discomfort is the doorway.
You don't have to kick it down.
You don't have to pretend you're not scared.
You just have to decide whether it's worth walking through.
Because every once in a while, the thing on the other side isn't just something you accomplished.
It's a slightly bigger version of yourself.
Curiosity pulls you toward discomfort.
Adventure requires it.
You don't have to raise a kid to jump off cliffs or cross oceans.
But I do want to raise one who looks at the edge of what he knows and thinks:
I wonder what's over there.
Captain your own ship
This connects to something else I've always believed.
Agency matters.
Melissa and I lived in St. Petersburg, Florida, for a couple of years when Nikko was little. We were about a block from the Gulfport Marina, and at one point we both started taking sailing lessons.
We got pretty serious about the idea.
We were looking at buying a big sailboat—something around 45 feet—and imagining what life might look like if we actually did it.
And strangely enough, sailing became part of the allure of moving to Puerto Rico.
From Florida, Puerto Rico was somewhere you'd spend a couple of weeks sailing to.
But if we lived in Puerto Rico, we could spend those same two weeks sailing from it.
Ten different islands.
Each one maybe a day's sail from the next.
Wake up.
Check the weather.
Raise the sails.
See where you end up.
I still buy Nikko maps of the Caribbean and joke with him that someday we're going to disappear for a year or two.
Sail.
Surf.
Sail.
Dive.
Sail.
Eat.
Fish.
Look for treasure.
Sail some more.
Maybe we actually do it someday.
I hope we do.
Because sailing is a pretty good metaphor for the way I hope he learns to approach life.
You're the captain.
But you're definitely not in control.
You're at the mercy of the wind.
The ocean.
The weather.
Storms.
Currents.
Things underneath you that you can't even see.
You don't get to tell the wind which direction to blow just because you've decided where you want to go.
But you aren't powerless either.
You learn to read it.
You adjust the sails.
You change course.
Sometimes you wait.
Sometimes you turn around.
Sometimes you find another island.
I've spent a lot of my life as an entrepreneur—building things, trying things, succeeding at some and failing at others.
And one of the things I hope Nikko eventually understands is that he has more ability to steer his life than he sometimes thinks.
Not total control.
Letter No. 1 was basically an argument against that idea.
The ocean is still the ocean.
But you do get to steer.
You can learn.
You can change direction.
You can build something.
You can leave something that isn't working.
You can start again.
You can become better at things.
You can captain your own ship.
That doesn't mean the sea cooperates.
It means you learn how to sail.
And you don't learn that tied to the dock.
Growth or atrophy
There seems to be a basic rule in life:
Things that aren't challenged tend to weaken.
Muscles.
Skills.
Relationships.
Curiosity.
Maybe courage too.
At 58, I can feel the temptation to make life more comfortable.
I've earned some comfort.
I've done some shit.
Why not make things easier?
And to some extent, sure.
I'm not interested in manufacturing hardship just to prove something.
But I also don't want comfort to quietly become the organizing principle of my life.
Because comfort has a funny way of shrinking the world.
You stop doing things because they're inconvenient.
Then because they're difficult.
Then because you're not good at them.
Then because you might look stupid.
Eventually your life can become very comfortable and very small.
I don't want that for Nikko.
And I don't want it for myself.
The tricky part
The difficult thing about parenting is knowing when to step in.
There are moments when your kid genuinely needs you.
There are moments when he needs protection.
There are moments when the right thing to say is:
I've got you.
And there are other moments when love might mean standing a few feet away and letting him struggle.
Try again.
Figure it out.
Stay with it.
I'm right here.
That's the balance I'm trying to understand.
Not toughness for the sake of toughness.
Not some bullshit idea that kids need to suffer in order to become men.
And not removing every sharp edge from life either.
Security and challenge.
Roots and wings.
A safe place to return to and enough freedom to wander away from it.
Maybe that's what I'm trying to give him.
What he might remember
There's another reason I've been thinking about all of this.
I'm 58.
Nikko is five.
Nobody knows how much time they get.
Hopefully I've got another thirty or forty years and someday he's tired of hearing me talk about this shit.
But maybe I don't.
My father had almost fifty years to show me who he was.
And even then, so much of what I learned about him came indirectly.
Stories on boats.
His friends telling me things he'd done before I was around.
People laughing about some ridiculous adventure.
Little pieces of a man that I assembled over time.
That's part of why I'm writing these letters.
Maybe Nikko reads them someday.
Maybe when he's fifteen he thinks they're stupid.
Maybe at twenty-five something in one of them suddenly makes sense.
And maybe someday he's a father himself, looking at his own kid and trying to figure out some version of the same things I'm trying to figure out now.
Maybe then he sees the line a little more clearly.
The great-grandfather who died when his grandfather was thirteen.
The grandfather from the Bronx who showed his love mostly through what he did.
His dad, who kept some of that and tried to do a few things differently.
And then him.
Figuring out what he wants to carry forward and what he wants to change.
That's part of what I hope these letters give him.
Not answers.
Just a record of what I was thinking while we were actually living it.
The things we tried to teach him.
The example we tried to set.
The things we probably got wrong.
And hopefully enough room for him to make his own mistakes and figure out the rest for himself.
Maybe when he's a father he'll understand what the hell I was thinking when he was five.
Well, this is what I was thinking.
I loved you enough to want you to feel completely safe.
And I loved you enough to know I couldn't keep you there.
Try this
Do something you're not good at.
Not because you need another hobby.
Not because you're trying to optimize yourself.
Just put yourself back in the position of being a beginner.
Take the class.
Paddle out.
Walk into the gym.
Learn the instrument.
Try the thing you've been avoiding because you might suck at it.
And pay attention to what happens inside you when you're uncomfortable.
Do you immediately want out?
Do you get frustrated?
Do you make excuses?
Do you compare yourself to people who've been doing it for years?
Or can you stay there for a while?
Can you suck at something and come back tomorrow?
Because maybe getting comfortable being uncomfortable doesn't mean learning to enjoy discomfort.
Maybe it means learning that discomfort isn't a reason to stop.
And if you're raising kids, maybe there's another question worth sitting with:
Am I protecting them from danger—or protecting them from discomfort?
Those aren't the same thing.
I'm still figuring out the difference.
— Rob