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Time Travel Pen Pals

I think we can agree that 2020 has been an interesting year for all of us.

Well…something just happened to me that made my year all the more surreal.

Over Thanksgiving break, I found a portal that allows for time travel.


Look, I know you’re not going to believe me but I’m going to explain, in detail, how this happened.

Two Days Ago…

I was looking through my filing cabinet when I came upon a letter that I wrote when I was 12 years old. I’ve posted it below for proof.

I was 12, imagining myself as a 36-year old, writing a letter to myself at 12-years old.

After finding this letter, I called my exhilarating model wife into the room and read it to her. We laughed at the idea of a square TV…or one that’s only 45″. We giggled at my youthful obsession with designer clothes while I now wear superhero t-shirts and jeans everyday. We also both found it hilarious how my love of comics has been so consistent throughout my life.

I decided to read it out loud a second time.

That’s when it happened.

The Portal Opened

green and purple abstract painting

There was an explosion of concentrated light about the size of a tennis ball. It was like a swirl of colors, mostly green and purple.

After the light exploded, it started to expand and there was a strange sound coming from the center of the portal. It sounded like this:

Next, a handwritten letter drifted out from the light and gently fell to the floor.

It was a note I’d written when I was 4. I read the letter, all the while the portal remained open.

Once I finished reading the letter, the portal started pulsing as if it were waiting for something.

I flipped over the note and wrote a reply on the back, folded it up, and sent it back through the portal.

Over the next hour, the portal remained open and I received several letters and notes from various points in my life. In each case, the portal remained open until I’d written back to myself.

I’d just become my own Time Travel Pen Pal.

After the last letter was sent back, the portal was closed. I don’t know if it will ever open again.

Below, I’ll share with you the letters I’d received from myself and what I’d written back to myself. In going through this process of writing back and forth with myself, I reflected on how the experiences of my life have shaped who I am today, and how grateful I am for my failures and heartbreaks.

Jeffrey, Age 4

The first letter I received was from when I was only 4 years old and it came with a photo.

My best friend is Hoppy and I love Superman. I’m going to Disney World soon. I can’t wait to see Mickey and Goofy. I want to get a dog but mom and dad both said no.


Dear Jeffrey,

I’m you, but much older…I’m 40 now! I’m happy to tell you that Hoppy is doing great. He is now watching over our daughter and making sure to keep her company. He told me to tell you hello. I’ve attached a picture.

Disney World is going to be great, but trust me when I tell you that you are going to love Disney SO much more when you’re my age. Just think about how much you love Star Wars and Superheroes.

Don’t be upset about the dog. You may not get a dog now, but in the future, you’re going to have two incredible dogs: Bailey and Emma. You will love them both so much and they’ll be worth the wait.

I know you think Superman is cool, but there are so many great superheroes to enjoy. Trust me, wait until you see how cool Spider-Man is.

In fact, one day you may even discover that you are a superhero.

Never lose that excitement or curiosity.



Jeff, Age 13

Dear future me,

All I want in this world is to be a professional basketball player. Please tell me, am I a Point Guard in the NBA?


Jeff, PG #13


I have good news and bad news. Let’s start with the “bad news,” you are not a professional basketball player.

Here’s the good news, there’s not a day in my life that I have regretted that fact. My/your career is an amazing journey.

Do NOT give up on your dream of being a professional basketball player. Do not give up on the dream that comes after that, nor should you give up on the dream after that. Your life will have so many ambitions and dreams. Follow that passion you have, for whatever is in your heart, because that is the path you must take to get where you are today. Trust me, you’ll love it when you get here.


Future You, Age 40

Jeff, Age 18

Dear Me,

Why did mom have to get into that accident? Why did that have to happen to her? Is she going to be ok? What am I going to do?

What is going to happen to me?

I feel like everything is out of control.



This is going to be one of the hardest things you will ever have to endure. Mom is going to make it through this, but she will never be the same. Stay positive, like you always are…Mom needs that and so do you. I know this feels awful right now and it is, but, from this tragedy you will learn so much: resilience, patience, compassion, and responsibility. Enduring this moment and all that will come from this will make you a stronger person. You are going to show your true colors by how you take care of Mom in your early twenties and throughout your thirties.

Use this experience as the fuel that drives you to appreciate every moment you have, because you never know how your life can change in an instant.



Age 25: Who am I going to be?

Dear future me,

Is this seriously the best life is going to be? I don’t want to be a server or bartender forever. I want to do something I care about. How is any partner going to take me seriously if I’m constantly living month-to-month? I cannot seem to get ahead, just catch up…and then fall behind again.

The bigger problem is, I have no idea what I even want to do anymore. Pro basketball didn’t workout. Filmmaker didn’t work out. Photographer didn’t work out. Personal Chef didn’t work out. I’ve lost my passion. I feel as though I’m doomed to work a job that I hate. I despise my lack of motivation but not nearly as much as my lack of direction or lack of skills.

Who the hell am I going to be, because this isn’t cutting it!



I know you aren’t going to want to hear this, but all of this, will wind up being good for you. I know it sucks right now, I was there. Remember that week where we survived in ginger snaps and water because we couldn’t afford any food? I still tell that story and it reminds me of my ability to deal with life as it comes. The hardships you’re currently enduring and that feeling of being lost and without purpose, are the context that make it so satisfying once you figure out who you want to be.

None of the things you’ve “failed” at were wasted time. Each is part of who you are. Each contribute to your overall set of skills. Your unique blend of knowledge will be extraordinarily valuable in the future.

  • Your love of basketball will help you to harness a competitive spirit and will give you a foundation for understanding strategy.
  • Your background and education in film will help you understand the structure of stories and give you greater media literacy moving into an age of unprecedented information overload where truth is under constant assault.
  • Your work as a photographer will give you a strong foundation in digital media from your work building websites, editing photographs, and working across multiple graphic design platforms.
  • Finally, your work as a personal chef is going to make your wife and her family exceptionally happy. The kitchen will be where you retreat to in order to clear your mind and relax.

Never think that anything you’ve done in your life is wasted. There are lessons and there is value in all of your experiences, even the negative ones.

If you don’t like where you are…make a change. Take bold action. That’s what I did.

Remember that this is all part of the process. Trust the process.



P.S. “Trust the Process” will make much more sense later, once you decide to be a 76ers fan instead of a Knicks fan…which you will do, by the way.

Jeff, Age 34

I’m an emotional mess right now. I can’t focus on anything.

My marriage fell apart and I didn’t even see it coming. Now I need to move out.

I hate looking for apartments. It’s depressing. Any place I’ve found that I would like to move into is too expensive, so I’m left moving into a crappy, small apartment…just me and my dog. Me against the world.

I want my clients to love me but I feel too lost and scattered to serve them. My brain is working against me. It’s like a tiny voice in the back of my head pulling levers and derailing the confident side of me. It doesn’t help that I feel crippled by debt, all of the time.

I miss being in love, I miss having someone to care for, and someone to care for me. I miss the attention, I miss having someone to lay my head on.

I’m a little lonely, a little overwhelmed, a little apathetic, a little stressed out. I feel a bit self conscious, and a bit down about whether or not I can accomplish the things I’m setting out to do.

I just feel overwhelmed by everything. I barely want to get out of bed to take on the day. It’s too heavy.

All I want to know is: Am I going to be ok?




Oh man, it feels like just yesterday that I was sitting there writing this journal entry. I remember talking to Dad on my way back to our new apartment—that you’ll soon move into—and collapsing on the kitchen floor crying from the depths of our soul. The pain you are experiencing right now is not something you will likely forget. These are times where our stress and anguish are at an all time high.

It’s only been 6 years but I can assure you, so much has changed.

You are right, at the time that you wrote this, it is just you and Emma, and aren’t we lucky to have her? Our sweet Emma will keep us company and love us unconditionally when we’re happy and when we’re sad. She’ll keep us grounded and she’ll get us out of the house. Don’t overlook how important that dog is in our story. Cherish her goofy moments and make sure she knows how much you appreciate her.

I know you feel lonely now, but in about a year, you will meet the love of your life. She is someone who will “get you” and love you for exactly who you are. I’m not exaggerating when I tell you it is a fairy tale love story. You even get married by a unicorn officiant. I’d link you the article but obviously you wouldn’t be able to see it as it hasn’t come out yet. But, here’s a picture…

You have a baby girl now. She’s perfect. The moment she is born will hit you in the chest like nothing you’ve ever felt before. It will feel like your heart cannot take anymore and is on the verge of exploding out of your chest. But it can take more, and it does…every single day.

You, your wife, your daughter, and Emma all live in a house, in your favorite neighborhood in Philly. That means no more apartment searching.

A mere 6 years later, and your career feels nothing like it did as you wrote this journal entry. Your dreams of being a Superhero as a child are now a reality as your brand revolves entirely around super-heroism, and using your powers to make a better, kinder, safer, and more equitable world. Instead of chasing opportunities, all of your hard work over the last decade has made things much less difficult. You are going to love what you do just a short 6 years later.

Jeff, the truth is, you’re not going to be ok.

You’re going to be great.

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