After sharing my 10-year letter earlier this week, I wanted to share how I actually went about writing it. The truth is, I didn’t sit down and write the letter all at once. It came together over the course of a couple of weeks.
Here’s the simple process I used.
1. Start with a few topics, not a full letter
The first thing I did was write down a handful of bullet points—just areas of life I thought my future self might talk about.
Things like:
• health
• relationships
• travel and experiences
• the podcast
• the kind of person I hope I’m becoming
I didn’t try to write the letter yet. I just let the list grow for about a week. Whenever something came to mind, I added it.
That gave me a rough map of what mattered most.
2. Write the entire letter by hand
Once I had those topics, I sat down and wrote the whole letter by hand.
No editing.
No second guessing.
Just stream-of-consciousness writing.
The goal wasn’t to make it perfect. It was simply to see what the future version of me might actually want to say. Writing by hand helped because it slowed me down and made the process feel more personal.
3. Let it sit
After finishing the handwritten letter, I didn’t touch it for a few days.
That break turned out to be really helpful. When I came back to it later, I could see it with a little more perspective. Some things felt more important. Other parts felt repetitive.
4. Rewrite it on the computer
Finally, I typed the letter on my computer. This wasn’t about changing the message—it was about clarifying it.
I removed some redundancy, tightened a few thoughts, and organized the sections so the ideas flowed better. The goal was simply to create a version I could read out loud without a lot of crossed-out lines or confusion.
But the heart of the letter stayed the same.
And speaking of reading it out loud—writing the letter was interesting, but reading it publicly on the podcast was something else entirely.
There’s something about hearing the words that makes them feel more real.
⸻
If you decide to try this exercise, my biggest advice is simple:
Don’t try to write the perfect letter. Just imagine the version of you living ten years from now sitting down across the table and talking honestly about the life you’ve built.
If you’re not sure where to start, try finishing this sentence:
“Dear me, thank you for…”
You might be surprised where it goes.
One other thing I highly recommend: once you’ve written your letter, share it with a close friend. Someone who knows you well, who can ask questions, push you a little deeper, and hold you accountable for the life you say you want to build.
If you do write one and feel comfortable sharing it, I’d love to read it. Feel free to send it along or share a few lines in the comments.
Some of the most powerful reflections come from simply taking the time to imagine what your future self might say.
I’ve heard about versions of this exercise for years.
You know the one: What would you tell your younger self? What would the future version of you say if you could sit down and have a conversation? It always sounded interesting, but also a little abstract—like something you’d hear at a conference or a corporate retreat. We’ve even mentioned the idea a few times on the podcast.
Recently, we decided to actually do it.
We sat down and wrote letters to ourselves from ten years in the future. Not advice from the past—but perspective from ahead. Writing it was harder than I expected. It forced me to think about what kind of life I actually want to be living a decade from now… and what the future version of me might thank me for or call me out on.
Reading the letter out loud was even scarier. But it was also surprisingly powerful.
We recorded ourselves reading these letters on the podcast. Hearing someone read a letter from their future self is a different experience than simply reading it.
Below is the exact letter I wrote and later read on the show. I haven’t changed a word.
_______________________
10 Year Letter to Self
Dear Rob,
I want to start this letter by Thanking You! Everything you have done up until this point and what you will do in the next 10 years has given me an incredible life. You should look back and be incredibly proud of what you have done. You should look forward with excitement for this next decade. You wouldn’t believe me if I told you everything that happens, but here are some of the things I am benefiting from today.
You and Tara continue to travel, but the experiences will become more diverse and distinctly unique from prior trips. Your “small” trips will be bigger than they were before, and your “big” trips will be significantly more diverse. While all your travel has shaped you in some way, this next decade of travel is going to be through a totally different lens. You enter it wiser and more open to growth than ever before. You know that list of 50 things to learn, well you finished it. It took us the whole decade, but you did complete all the items. While some were goofy, some were 1 and done, there are a number that I still enjoy doing today. Spanish was really helpful on the big motorcycle trip through South America.
I wish I could tell you that I am a male swimsuit model, but sad to say, I am not. I am however one of the healthiest and fittest over 60 year olds in our community. You will continue to do endurance events, and yes you finally buckle at WSER. FYI – we don’t get any faster, but we are still out there, doing it. I take the most pride in the stability of our healthy lifestyle and the fact that we don’t need any medications. Keep up with the strength training and get more consistent with Yoga. I need these in order to be active for the next 20 years!!! Speaking of health, the greatest growth has come in your mental health. What started that morning during Cocodona has continued and changed you for the best. It isn’t lip service anymore, I love myself. Thank you for putting in the work to get us here today. The conversations in my head are mostly positive now. I know, hard to believe, but it’s true. We have also mellowed out quite a bit, though I wish that had started earlier. While I still have that fuse, it is so much longer now that I rarely ever get angry.
The Podcast is still going strong and you have a huge 10 year anniversary celebration. This is what you are meant to do. Be patient and keep going. Not only is this changing you, it is helping a generation live their best midlife. I can’t wait for you to read some of the letters that the audience sends to you. You can finally say you found your calling and you get to do it with one of your closest friends.
Now I have been saving the best for last.
I have the best relationships. We have friends located all over the world, some people you don’t even know yet. Please don’t change the path you are on today. You are developing deeper more connected relationships with your existing group. We laugh, oh do we laugh, have fun, travel and do crazy shit together still to this day. Some of them will join you on your big adventures in the next few years and you will get to experience things through their eyes. Make sure you tell them how much they mean to you while you can. We have also increased the quantity and quality of the time we spend with our family. Those relationships have grown and been transformed. Keep helping your parents take those big trips. The change of pace of these adventures is good for you and for them.
Finally, Tara.
Yes, she is still with you. Yes, you deserve her, but barely. Your relationship will see the most change over the next 10 years compared to everything in this letter. You don’t fall into a rut, you carve an entirely new path going forward. She continues to be our best friend, our closest confidant, and even bigger cheerleader. She needs to hear how much she means to you so much more than you currently communicate.
Start to tell her and show her this more often, PLEASE!
Rob, thank you for giving me this life that I have had, and that I get to have.
I Love You,
Rob
________________
When I finished writing this letter, one thing surprised me.
The future version of me didn’t talk much about accomplishments. It talked about health, relationships, curiosity, and the kind of person I hope I’m becoming.
That alone made the exercise worth doing.
Later this week I’ll share how I approached writing this letter and the questions that helped me get past the obvious answers and into something more meaningful.
Until then, try this:
If the version of you living ten years from now could say one sentence to you today… what do you think it would be?
This episode of Midlife Circus meant a lot to me. Writing a letter from my future self back to today turned out to be a powerful exercise—honest, a little uncomfortable, and surprisingly emotional. Below is the letter I wrote to myself from ten years in the future. If it sparks something for you, I’d love to see your own 10-year letter in the comments too—only if you’re comfortable sharing. (The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most)
----------------
Hey Buddy,
I’m writing to you from ten years down the road. I’m 63 now, and you’re 53 as you’re reading this. It may not feel dramatic, but you’re standing at the front edge of a meaningful shift in life.
When I look back, what stands out most is how much you stayed focused on relationships, even as things were changing around you.
The boys grew up fast. Moving from being “dad” to something more like a guide, a sounding board, and eventually a peer wasn’t easy. You didn’t always know what the right move was, and that bothered you at times. But you stayed present. You listened. You didn’t force things. And because of that, the relationships you have with them today are strong, honest, and still evolving. That matters more than you probably realize right now.
You and Carolyn also stepped into the empty-nest chapter without trying to rush through it or pretend it wasn’t happening. You stayed curious together. You talked more. You let the relationship change instead of holding on to what it used to be. That openness created space—for new rhythms, new conversations, and a different kind of closeness.
Beyond your core family, you stayed connected. You didn’t let relationships with siblings, relatives, and longtime friends slide just because life was busy. You kept showing up. You made time. You shared experiences. Looking back, that consistency played a big role in what a healthy life actually looks like.
That word—healthy—turned out to be more than a theme. Back in 2026, you chose it as your word for the year, and without realizing it, you set the tone for the next ten. It became a filter for decisions, not a catchphrase.
Over time, you stopped measuring everything by outcomes and results. You became less critical—of yourself and of others. More present. Less rushed. That shift didn’t happen all at once, but you kept working at it, and it changed how you experienced day-to-day life.
Physically, you leaned in instead of pulling back. You respected your body, adjusted when setbacks showed up, and trusted its resilience. Because of that, you’re still doing the things you love—fly fishing, skiing, biking, golfing, exploring, and chasing adventures. You didn’t step away from movement or risk. You just got smarter about how you took care of yourself along the way.
There’s one more thing worth calling out.
Back in your mid-50s, you and Rob committed to building Midlife Circus. You didn’t know exactly what it would become, and that uncertainty was part of what made it work. The community kept growing, changing, and surprising you. It stayed alive because you stayed curious. Even now, it’s still evolving—still connecting people who are trying to figure out what midlife really looks like.
So here’s what I want you to remember—and what I’d tell myself again if I could:
After sharing my 10-year letter earlier this week, I wanted to share how I actually went about writing it. The truth is, I didn’t sit down and write the letter all at once. It came together over the course of a couple of weeks.
Here’s the simple process I used.
1. Start with a few topics, not a full letter
The first thing I did was write down a handful of bullet points—just areas of life I thought my future self might talk about.
Things like:
• health
• relationships
• travel and experiences
• the podcast
• the kind of person I hope I’m becoming
I didn’t try to write the letter yet. I just let the list grow for about a week. Whenever something came to mind, I added it.
That gave me a rough map of what mattered most.
2. Write the entire letter by hand
Once I had those topics, I sat down and wrote the whole letter by hand.
No editing.
No second guessing.
Just stream-of-consciousness writing.
The goal wasn’t to make it perfect. It was simply to see what the future version of me might actually want to say. Writing by hand helped because it slowed me down and made the process feel more personal.
3. Let it sit
After finishing the handwritten letter, I didn’t touch it for a few days.
That break turned out to be really helpful. When I came back to it later, I could see it with a little more perspective. Some things felt more important. Other parts felt repetitive.
4. Rewrite it on the computer
Finally, I typed the letter on my computer. This wasn’t about changing the message—it was about clarifying it.
I removed some redundancy, tightened a few thoughts, and organized the sections so the ideas flowed better. The goal was simply to create a version I could read out loud without a lot of crossed-out lines or confusion.
But the heart of the letter stayed the same.
And speaking of reading it out loud—writing the letter was interesting, but reading it publicly on the podcast was something else entirely.
There’s something about hearing the words that makes them feel more real.
⸻
If you decide to try this exercise, my biggest advice is simple:
Don’t try to write the perfect letter. Just imagine the version of you living ten years from now sitting down across the table and talking honestly about the life you’ve built.
If you’re not sure where to start, try finishing this sentence:
“Dear me, thank you for…”
You might be surprised where it goes.
One other thing I highly recommend: once you’ve written your letter, share it with a close friend. Someone who knows you well, who can ask questions, push you a little deeper, and hold you accountable for the life you say you want to build.
If you do write one and feel comfortable sharing it, I’d love to read it. Feel free to send it along or share a few lines in the comments.
Some of the most powerful reflections come from simply taking the time to imagine what your future self might say.
A Letter From My Future Self (10 Years From Now)
I’ve heard about versions of this exercise for years.
You know the one: What would you tell your younger self? What would the future version of you say if you could sit down and have a conversation? It always sounded interesting, but also a little abstract—like something you’d hear at a conference or a corporate retreat. We’ve even mentioned the idea a few times on the podcast.
Recently, we decided to actually do it.
We sat down and wrote letters to ourselves from ten years in the future. Not advice from the past—but perspective from ahead. Writing it was harder than I expected. It forced me to think about what kind of life I actually want to be living a decade from now… and what the future version of me might thank me for or call me out on.
Reading the letter out loud was even scarier. But it was also surprisingly powerful.
We recorded ourselves reading these letters on the podcast. Hearing someone read a letter from their future self is a different experience than simply reading it.
Below is the exact letter I wrote and later read on the show. I haven’t changed a word.
_______________________
10 Year Letter to Self
Dear Rob,
I want to start this letter by Thanking You! Everything you have done up until this point and what you will do in the next 10 years has given me an incredible life. You should look back and be incredibly proud of what you have done. You should look forward with excitement for this next decade. You wouldn’t believe me if I told you everything that happens, but here are some of the things I am benefiting from today.
You and Tara continue to travel, but the experiences will become more diverse and distinctly unique from prior trips. Your “small” trips will be bigger than they were before, and your “big” trips will be significantly more diverse. While all your travel has shaped you in some way, this next decade of travel is going to be through a totally different lens. You enter it wiser and more open to growth than ever before. You know that list of 50 things to learn, well you finished it. It took us the whole decade, but you did complete all the items. While some were goofy, some were 1 and done, there are a number that I still enjoy doing today. Spanish was really helpful on the big motorcycle trip through South America.
I wish I could tell you that I am a male swimsuit model, but sad to say, I am not. I am however one of the healthiest and fittest over 60 year olds in our community. You will continue to do endurance events, and yes you finally buckle at WSER. FYI – we don’t get any faster, but we are still out there, doing it. I take the most pride in the stability of our healthy lifestyle and the fact that we don’t need any medications. Keep up with the strength training and get more consistent with Yoga. I need these in order to be active for the next 20 years!!! Speaking of health, the greatest growth has come in your mental health. What started that morning during Cocodona has continued and changed you for the best. It isn’t lip service anymore, I love myself. Thank you for putting in the work to get us here today. The conversations in my head are mostly positive now. I know, hard to believe, but it’s true. We have also mellowed out quite a bit, though I wish that had started earlier. While I still have that fuse, it is so much longer now that I rarely ever get angry.
The Podcast is still going strong and you have a huge 10 year anniversary celebration. This is what you are meant to do. Be patient and keep going. Not only is this changing you, it is helping a generation live their best midlife. I can’t wait for you to read some of the letters that the audience sends to you. You can finally say you found your calling and you get to do it with one of your closest friends.
Now I have been saving the best for last.
I have the best relationships. We have friends located all over the world, some people you don’t even know yet. Please don’t change the path you are on today. You are developing deeper more connected relationships with your existing group. We laugh, oh do we laugh, have fun, travel and do crazy shit together still to this day. Some of them will join you on your big adventures in the next few years and you will get to experience things through their eyes. Make sure you tell them how much they mean to you while you can. We have also increased the quantity and quality of the time we spend with our family. Those relationships have grown and been transformed. Keep helping your parents take those big trips. The change of pace of these adventures is good for you and for them.
Finally, Tara.
Yes, she is still with you. Yes, you deserve her, but barely. Your relationship will see the most change over the next 10 years compared to everything in this letter. You don’t fall into a rut, you carve an entirely new path going forward. She continues to be our best friend, our closest confidant, and even bigger cheerleader. She needs to hear how much she means to you so much more than you currently communicate.
Start to tell her and show her this more often, PLEASE!
Rob, thank you for giving me this life that I have had, and that I get to have.
I Love You,
Rob
________________
When I finished writing this letter, one thing surprised me.
The future version of me didn’t talk much about accomplishments. It talked about health, relationships, curiosity, and the kind of person I hope I’m becoming.
That alone made the exercise worth doing.
Later this week I’ll share how I approached writing this letter and the questions that helped me get past the obvious answers and into something more meaningful.
Until then, try this:
If the version of you living ten years from now could say one sentence to you today… what do you think it would be?
Thanks for reading,
rob
This episode of Midlife Circus meant a lot to me. Writing a letter from my future self back to today turned out to be a powerful exercise—honest, a little uncomfortable, and surprisingly emotional. Below is the letter I wrote to myself from ten years in the future. If it sparks something for you, I’d love to see your own 10-year letter in the comments too—only if you’re comfortable sharing. (The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most)
----------------
Hey Buddy,
I’m writing to you from ten years down the road. I’m 63 now, and you’re 53 as you’re reading this. It may not feel dramatic, but you’re standing at the front edge of a meaningful shift in life.
When I look back, what stands out most is how much you stayed focused on relationships, even as things were changing around you.
The boys grew up fast. Moving from being “dad” to something more like a guide, a sounding board, and eventually a peer wasn’t easy. You didn’t always know what the right move was, and that bothered you at times. But you stayed present. You listened. You didn’t force things. And because of that, the relationships you have with them today are strong, honest, and still evolving. That matters more than you probably realize right now.
You and Carolyn also stepped into the empty-nest chapter without trying to rush through it or pretend it wasn’t happening. You stayed curious together. You talked more. You let the relationship change instead of holding on to what it used to be. That openness created space—for new rhythms, new conversations, and a different kind of closeness.
Beyond your core family, you stayed connected. You didn’t let relationships with siblings, relatives, and longtime friends slide just because life was busy. You kept showing up. You made time. You shared experiences. Looking back, that consistency played a big role in what a healthy life actually looks like.
That word—healthy—turned out to be more than a theme. Back in 2026, you chose it as your word for the year, and without realizing it, you set the tone for the next ten. It became a filter for decisions, not a catchphrase.
Over time, you stopped measuring everything by outcomes and results. You became less critical—of yourself and of others. More present. Less rushed. That shift didn’t happen all at once, but you kept working at it, and it changed how you experienced day-to-day life.
Physically, you leaned in instead of pulling back. You respected your body, adjusted when setbacks showed up, and trusted its resilience. Because of that, you’re still doing the things you love—fly fishing, skiing, biking, golfing, exploring, and chasing adventures. You didn’t step away from movement or risk. You just got smarter about how you took care of yourself along the way.
There’s one more thing worth calling out.
Back in your mid-50s, you and Rob committed to building Midlife Circus. You didn’t know exactly what it would become, and that uncertainty was part of what made it work. The community kept growing, changing, and surprising you. It stayed alive because you stayed curious. Even now, it’s still evolving—still connecting people who are trying to figure out what midlife really looks like.
So here’s what I want you to remember—and what I’d tell myself again if I could:
Stay present.
Take care of the body you want to keep using.
Invest in relationships.
And stay open to what’s next.
You’re doing better than you think.
I love you!