I want to be a great dad.

Not just today, but every day until I die.

I want to be present and available, loving and supportive, caring and kind. I want to meet our son where he is and show up every time.

I want to forgive and be forgiven. I want him to know that our bond is sacred. That it’s secure and safe.

I want to cheer his biggest celebrations and support his terrible lows. Life’s beautiful in that way.

I want to show up in one of the most vulnerable times in a person’s life, when his child arrives.

I want him to know that he’s not alone and that he never will be, even after I’m gone.

I want him to know that his dad is always here, in his heart. Carried until his end.

Craig
21 June 2026

To my future self,

I gotta say something out loud. I have to say it because I don’t want to hear it. Because it’s easy to hide in it.

You’re going to suck.
You’re going to fail.
It will hurt more than you can imagine.

Feel that?

That’s what you’re afraid of. That feeling right there. That emptiness in your heart, the stuck throat. That’s what you’re afraid of.

You’re going to suck.
You’re going to fail.
It will hurt more than you can imagine.

This is holding you back. This is keeping you small.

You’re going to suck.
You’re going to fail.
It will hurt more than you can imagine.

As soon as you can accept this, it becomes easy. There’s no need for courage if you know you can suck, fail, and hurt. These are three of an infinite number of outcomes.

Accept that you’re going to suck.
Accept that you’re going to fail.
Accept that it will hurt more than you can imagine.

Accept that you’ll fully experience this shittiness.

Now, get on with your life.

Craig
15 June 2026

Congratulations, our son just graduated! I imagine you’re on the cusp of something big. Not the typical things like how to get ready for college or how to say goodbye as friends depart.

No, it’s something more fundamental. A choice his mom and I didn’t have to make.

Where’s home?

He has two right now. That’s divorce. His mom and I do our best to make it feel fluid. But now he has the choice. Where does he want to go during breaks? I don’t know where I, nor his mom, will be. Can we still make him a home?

I need to detach from the sense that these walls make it home. This green couch and our twin beds are comfortable, but temporary. I need to create some other version with him in a thoughtful, kind-hearted way.

I suspect these walls will change one day. I hope that lovely people enter our lives. People with whom we want to share space.

I need to create an invitation. An invitation that transcends space and fills our hearts.

That’s home.

I’m starting now.

Craig
7 June 2026

I’m the guy who knows what needs to be done. I pick a destination and run. I never question it.

I’ve done some incredible things.

I think I’m finally ready to admit that I have no idea what I’m doing.

Looking forward, the best I can do is set an intention and work my tail off. For example, I’m writing these letters in the hope that they’ll be valuable, but I have no idea if it’s worth it. I’m dedicating my precious life to this dream that may or may not come true.

The only thing I know to be true is that I need to keep moving my feet, as fast as I can, even though I don’t know where I’m going.

I used to think the plan is the most important thing. But now, I know that it’s just going to fall apart the moment I take a step. Now, I know it’s better to just start becoming that person I want to be instead of spending another second thinking about whether or not it’s worth it.

I have no idea what I’m doing. I don’t know if I ever will.

My hope is that one day you’ll look back at this letter and think, “yeah, that’s a good way to live life.”

Craig
1 June 2026

I don’t know when, but there will be a day when you have enough.

Enough money, enough time, enough of an activity.

Enough is the reward. It is the fruit of who we are.

Like a car on the interstate, we tend to blow past enough.

But don’t make that mistake again.

Pause. Feel it.

Make a nest.

Be enough.

Craig
24 May 2026

So you’re lonely. It’s not a question. It’s a fact.

Take a deep breath. Let it out. Lonely.

Feel into it. Feel the loneliness. Wherever you’re sitting, just feel it.

Feel that longing for someone who isn’t here.

Feel that desire to be seen and cherished. The want to know someone.

Touch it. Experience it. You’re lonely.

You wish it wasn’t this way. You wish things were easier. You wish you weren’t alone. But you are, and that’s ok.

We’ve been here before.

There’s power here in feeling lonely. Touch it. Befriend it.

I’m sure your mind is racing, “What am I going to do?” Don’t run away.

Just be.

Lonely.

You’re not the only one.

Even if there’s no one around, you’re part of something bigger. Your presence on this earth is part of a whole.

Listen. What do you hear? Maybe the birds. A humming refrigerator. A plane passing by.

Life.

That’s something.

Something to grab on to, something to step towards, something to experience. Alongside your loneliness.

Get up, move your body, step into the light.

Look. I mean, really look. Take in the face of a driver passing by. Were they singing?

Take in the smells on the breeze. Were they sweet?

Graciously share a smile and see if it’s returned.

See the beauty. See your part in this whole.

Then, when you’re ready, reach out and share. Share that you’re lonely and you want to connect.

This loneliness isn’t yours alone.

Pick up the phone, send a text, do whatever feels right in this moment to connect.

Because there is someone on the other end. There always will be, no matter who you are, where you are, or how you got here.

Craig
17 May 2026

Hi,

I want to talk about what I’m doing here.

You’re nearly twice my age. I chose 80 because it’s a nice round number and it’s way beyond anything I can comprehend right now.

I imagine you reading this at 80, not understanding that I can’t comprehend who you are. It’s because I’m naive. Or, maybe, because there are so many possibilities.

I look back at that 20-year-old version of myself, and I realize that kid has no idea what’s in store for him. The things that are coming are fascinating. All the travel and friendships. The careers that have taken him all over the globe. He hasn’t jumped out of that airplane!

The difference this time is that I’m more mature. That kid didn’t know that he didn’t know. Now, I do. I know I don’t know what’s coming. I show up and do my best every day. The difference is that I think I can influence it a little bit.

Not in big ways, but a little bit.

Like, I’m in a restaurant in Australia, and kangaroo is on the menu. Should I order it?

Of course, I should order it. What a story to tell! I’ll be telling people for the rest of my life that I tried kangaroo.

Here’s the crazy thing. I took our son and his mom to the zoo today. It’s Mother’s Day. Guess who I didn’t expect to see in Seattle? Somebody’s cousin who showed up on a plate three years ago and 7700 miles away.

That’s another experience I didn’t know I could have when I chose what to have for dinner in a foreign country.

I want to be your friend.

I want to carry you around in my heart, like I do all the people I love.

I want to get to know you. What you like and don’t like. How little or big a decision really is on a 40-year time horizon.

But there are huge implications in tiny decisions. Should I say yes or no to an invitation? I know you’re going to want me to say yes way more than I do.

So, that’s what I’m doing here.

I’m writing to you as a friend with the hope that we’ll get to know each other.

Talk soon,

Craig
10 May 2026

Hey,

I just accepted this new job. I start in two weeks and I’m writing to you so you don’t lose yourself.

Every day is spacious. You’re in control.

Our year off was glorious. We woke up without an agenda. We meandered until we found meaning. We did some awesome stuff.

Now, part of our agenda is set by work. You’re in control.

Don’t lose yourself. You’re a father, storyteller, writer, and entertainer. This is who we became and who you are. You get to practice and live this every day. Look for the tiny opportunities to practice your craft. These things show up in every meeting, every interaction, and every cherished moment.

Doing it all is hard, but it makes you happy. You may be tired. That’s ok. Take a short break. You’re building compounding habits. Every word you write is building your compounding machine.

Don’t strive for balance. That’s a fool’s game. Instead, look at the entire picture of who you’re becoming in all areas and choose which you will pursue right now. If you leaned too far on work this week, lean back to your creativity next.

You’re in control of your attention.

Ideally, you’re a better dad, writer, storyteller, worker, and entertainer than I am right now. Put in the time. Make that happen. If you didn’t, that’s okay. Now’s the time to double down. Now’s the time to figure it out. These things make you happy.

Remember, every day is spacious. You’re in control.

Craig
3 May 2026

Hi,

I’m writing to my 100-year-old self this time because there’s a thing going around called the Centenarian Olympics. A longevity doctor sees patients in their 80s who struggle to perform life functions like carrying groceries, getting up and down from the floor, and lifting a carry-on bag into an overhead compartment. These things become challenging as our muscle and bone strength decline. The decline is natural and starts as early as your 30s.

I want you to be able to get off the toilet, any toilet. Mom had one of those raised seats. I wonder what she felt like walking into a public bathroom at 60. Did she wonder if she’d be able to get up?

I want you to be able to do whatever you want to do when you’re 100. I imagine you playing on the floor with our great-grandkids, living alone, and being able to say yes without hesitation.

So, I’m changing my habits. This year at 42, I started lifting weights. I got a 50lb kettlebell from Walmart that I pick up a few times per week. I’m glad I started because I’m getting stronger. I realize I’d be stuck if I didn’t start lifting heavy things. I don’t ever want you to be stuck. That’s a nightmare.

I never thought I would do this, but I started taking creatine and protein shakes to build muscle. It’s that important to me.

I know all this muscle will go away in the fullness of time. I want to keep it as long as I can. I’ve been so fortunate to come from strong Dutch stock. Grandaddy and Dad are strong. Grandma walked every morning through her 80s. She knew she had to keep it up.

I had this friend Joe from Boston. We met when he was in his 70s. We walked miles together from Harvard along the Charles River to his home. We ran across the street before the light turned green. There was no thought of tripping or imbalance. My friend Jim hiked the Two Moors Trail across England last year at 78. Dad came to Australia with us. That was a long flight.

I want that for you.

I never want your body to fail you. Well, maybe one day, but I want that to be the last.

I started these habits. I can’t imagine doing anything for 40 years, but I have a hunch that’s exactly what I’m going to do. That’s what I need to do to give you the best chance to live a full and healthy life.

I have this funny thought that right now, I’m the most fit and beautiful that I ever will be. It’s silly, but I think that can be true tomorrow, like it is today. Then the day after that and every day until we meet.

I hope you’re well,

Craig

Hey. Gosh, I hope I’m doing this right.

I’ve been thinking about my son for the past few months, and I feel like I’m finally ready to write to you.

Who am I gonna be in 40 years? The best example in my life is grandma.

My college was about a mile from Grandma’s house. She just turned 73 the week I started my freshman year. She had lived a full, beautiful life. And she was there for me.

I left home at 18 and didn’t really go back.

Not for any particular reason, it’s just how it was. You go to college, maybe for the summer, but you really try to get work wherever work is. I spent those, those 4 years of college living on campus, but much of it was with Grandma.

She was such a lively woman from ages 73 to 77. I’d be lucky to have her energy. I’m doing what I can now to make sure you have that kind of energy.

She’s my inspiration and my hope for myself, which is you.

My son just started high school, and he’s doing great. I’m convinced he’s an extrovert. He’s really leaning into his extroversion this year. It’s a beautiful thing to see, but it means that he’s gone much more than he was in middle school and before.

He’s interested in hanging out on video chats with his friends. They call it the group chat of life, which is a wonderful name for eight teenage boys trying to make sense of the world.

He’ll talk for hours with his friends.

He started dating this year. He wants to be with his girlfriend as much as possible. I get it. It’s all part of it, but a little part of me is leaving.

I get him half time, and this time away means we’re together even less. I’m not complaining, just seeing that his progress means letting go. It means our time together is finite and precious.

I try to do big things, like I try to have his friend Dylan spend the night, or take trips all over the world. He’s been to four continents so far. I hope to visit Africa and South America in the coming years. It’s not important to him, but it’s important to me that he experience how other people live.

I support anything that he wants to do. I think he knows that even though he doesn’t ask for much.

One of my favorite things is kicking the soccer ball with him. Last night was Friday. We snuck onto the field at Miller Park before the women’s lacross game started at 7:45. I know it won’t be so easy in a few years.

Part of me just loves sitting on this green couch that we bought together. I’m on the right. He’s on the left. We don’t have to talk or anything. It’s just nice being together.

I look over at him, and I’m grateful.

I don’t know if you’ll remember these particular Friday nights sitting on the couch. Something in me wants you to remember what it’s like, to get the details of me sitting at my desk with this letter. The green couch at my back, the overhead lights, the smell of a sink half-full of dishes waiting for the laundry timer to go off.

This is where I am, and I’m hopeful that wherever you are, whoever you are, you remember.

I hope that you look back and feel a warm heart when you think about this green couch which is probably long gone. I you remember our son, sitting together, and being present.

I hope he knows all these years later that I’m here for him.

Craig
19 Apr 2026