Thanks for sharing, being real and inspiring Chris! First small risk is now by making first comment for you here on your post as I write from Cornwall in the U.K. Right then. Risk taking for me in 2025 - writing! Every day. And starting my own Substack 🙀🙌✨💖 enjoy travels!
Thanks Chris. This year I’m going to finish my psychology degree, I fact I will in 3 weeks. My risk will be looking for a new job after 20 years in the same field in people management.
Your post could not be any more timely for me. Just this morning I was thinking about art and what I really want to get out of it (not for selling, just for me). I have put off learning figure drawing/painting for YEARS, mainly with the excuse that I don't want to draw/paint humans. Except that's not entirely true - I DO want to include figures in my creations at times. But the thought of learning the process literally makes my heart race. So I wrote in my journal: "What about learning this makes you so nervous? Why are you scared?" I'm contemplating this at the moment, while also remembering inspiration from many others that if something scares you, it probably means you need to do it.
So, my real risk seems to be I need to learn figure drawing and painting. It thrills and terrifies me! And I don't plan on telling anyone - just keeping it close to me and will work on it quietly. It's better to try than to regret it later (so I am telling myself!).
This is sooo cool! You're inspiring me to sign up for some kinda artsy class too. I haven't taken one in years and I miss that weekly chunk of time to be creative in community.
Love this! My life has been full of risks and I don't plan on stopping!
Actually speaking of traveling... I decided while working on my goal spreadsheet that I would in fact try to get to every country (before 65, although that was just an arbitrary number) which means I should travel to 5 new ones each year. Just booked Finland and Estonia for March. While I've traveled extensively because of my career, right now, traveling seems like more of a risk because I have a much less stable income, but never, never once have I ever regretted spending money on travel. So here I go.
"What's the risk I'll take this year/month/week/afternoon?" feels like a potent question I need to add to my thinking right now.
Your examples make me reflect on the subjectivity of risk - i.e., what qualifies as risky is partly a function of what you particularly fear or have to lose. Picking up and moving from Boston area to Chicagoland at 28 didn't feel like a risk to me, despite not knowing anyone here - I'd secured a well-paid job in my field with a respected company in my industry, and after my military upbringing, starting completely fresh in a place where I had no connections was familiar and something I had the skills to do. But making that move sounded incredibly risky to my New England acquaintances, even the most urbane of which had never lived outside the suburb in which they'd been born.
At the same point in time, inviting an established friend to hang out felt incredibly risky to me because of a rather specific type of rejection-averse social anxiety that I suffered from for years. I'm glad I made myself take that risk over and over again, because it really did cure me of that problem.
Nice post Chris. The risk I'm thinking about is taking a university class in data science this year. As a writer, the idea of developing more technical skills is a bit of a jump, but I'm excited about it!
I do enjoy reading your posts one of the things I would like to take a risk on is volunteering to read your articles ahead of time to point out spelling errors. It is risk-averse not risk adverse.
I am currently a software developer and attention to detail is very important to me. Also, for quite some time now, I have wanted to write a novel myself. It isn't that I am risk-averse it is that I don't believe in myself. I've taken many risks in life, not the least of which was having four children.
Thank you for inspiring me to take more risks at the age of 55!
I love this idea of writing a novel for you. It’ll use 100% of your brain, passion and research abilities. I think you’ll grow as a person and once finished, you’ll feel tremendous satisfaction checking this box. Maybe you can pretend every month is November—nanowrimo? I just might have to steal your idea and contemplate a novel of my own so I can deep research a subject that interests me.
Whoa, Chris! So much news! My risk? Writing the book about my incredible grandparents and their trip to Alaska! I look forward to catching up with you IRL. Have fun in Singapore, which I recall was HOT AS HELL!
Chris, I quote you at least once a month "ideas are great ideas with action are better" from your book the $100 Start Up. Sometimes the idea with action might be a risk but I would say not taking that risk comes at a higher cost!? I still continue with my side hustle as it's great doing something arty for my mental health while making $1000 a month. I have the links to my side hustle school episodes on my email signature. Last year I skied in Canada, snorkeled with turtles with my wife in the Cook Islands and did a road trip through Idaho, Montana and Wyoming so I could fly fish the Snake River in Jackson Hole WY with a friend, a lifetime objective. All of last years adventures were travelling with and often staying with friends to keep the cost reasonable and stay connected. Ngã mihi Martin
Chris, your rainstorm story immediately reminded me of when I lived for a year on a little Micronesian island, and the drenching, extraordinarily sheeting rain that would fall, sometimes suddenly. More than once I was caught on the little scooters we drove there, and soaked head to toe. (Living on a tiny island was one of the risks I took.)
This year, by hook or crook—or with the help of crooks—I'm going to publish my memoir of my truly lunatic near-40-years correspondence with the Jack Daniel's distillery. The draft is written but as you know, that's a far winding mile to actually publishing. Thanks for the post!
My big risk for this year is releasing a book. I hope to have it available for purchase by the end of this year. Currently working on converting it into an ebook that I can send to beta readers.
Writing memoir is soo tough. I mean sometimes I can be absolutely great, freeing, healing, but then other times, you're just in the muck of it and just reliving without knowing how to relive better or gentler or in ways that won't just rip you apart again. Be easy on yourself through the process!
Not sure what risk I’ll take yet, but I’d definitely like to figure out how to have someone on my very technologically unskilled podcast OR guest on someone else’s (which may be safer tech-wise). I’d just like to put myself out there to talk about being a decluttering expert & helping those with ADHD like me.
Last year, I challenged myself to do 3 public speaking events. I gave 4 presentations & am now looking to do more. That’s a win! 🏆
Reading this in the quiet morning hours and realizing: some of the most beautiful chapters of my life began with a tiny whisper—“Just try.”
I moved to a new city on a gut feeling once. Said yes to a mentorship I wasn’t sure I was ready for. Wrote a book I thought no one would care about. Each time, I risked looking foolish. Each time, I came out changed.
Right now, my small risk is putting more of my truth out there—through writing, art, voice. Not trying to be perfect. Just honest.
Thanks for reminding me that uncertainty is often just the front door to the good stuff.
Thanks for sharing, being real and inspiring Chris! First small risk is now by making first comment for you here on your post as I write from Cornwall in the U.K. Right then. Risk taking for me in 2025 - writing! Every day. And starting my own Substack 🙀🙌✨💖 enjoy travels!
I love that! Excited for your Substack; please share when you get it up and running. (You too, Natália Pompom.)
Hi, Karen! I also want to start a substack this year as my risk-taking endeavour! Good luck to us both 🤞
No risk no reward
Thanks Chris. This year I’m going to finish my psychology degree, I fact I will in 3 weeks. My risk will be looking for a new job after 20 years in the same field in people management.
Good luck!!
Hi Chris - Happy New Year!
Your post could not be any more timely for me. Just this morning I was thinking about art and what I really want to get out of it (not for selling, just for me). I have put off learning figure drawing/painting for YEARS, mainly with the excuse that I don't want to draw/paint humans. Except that's not entirely true - I DO want to include figures in my creations at times. But the thought of learning the process literally makes my heart race. So I wrote in my journal: "What about learning this makes you so nervous? Why are you scared?" I'm contemplating this at the moment, while also remembering inspiration from many others that if something scares you, it probably means you need to do it.
So, my real risk seems to be I need to learn figure drawing and painting. It thrills and terrifies me! And I don't plan on telling anyone - just keeping it close to me and will work on it quietly. It's better to try than to regret it later (so I am telling myself!).
This is sooo cool! You're inspiring me to sign up for some kinda artsy class too. I haven't taken one in years and I miss that weekly chunk of time to be creative in community.
Go for it!
Love this! My life has been full of risks and I don't plan on stopping!
Actually speaking of traveling... I decided while working on my goal spreadsheet that I would in fact try to get to every country (before 65, although that was just an arbitrary number) which means I should travel to 5 new ones each year. Just booked Finland and Estonia for March. While I've traveled extensively because of my career, right now, traveling seems like more of a risk because I have a much less stable income, but never, never once have I ever regretted spending money on travel. So here I go.
Thank you for writing this! I have always viewed myself as fearful until my early 60's.
Now I am starting to realize that I have taken many risks!
I always hated the advice, “Do it scared”.
But I realized, that is exactly how I have led my life.
I just don't like to plan it ahead of time.
I'll have to work on that, now!
"What's the risk I'll take this year/month/week/afternoon?" feels like a potent question I need to add to my thinking right now.
Your examples make me reflect on the subjectivity of risk - i.e., what qualifies as risky is partly a function of what you particularly fear or have to lose. Picking up and moving from Boston area to Chicagoland at 28 didn't feel like a risk to me, despite not knowing anyone here - I'd secured a well-paid job in my field with a respected company in my industry, and after my military upbringing, starting completely fresh in a place where I had no connections was familiar and something I had the skills to do. But making that move sounded incredibly risky to my New England acquaintances, even the most urbane of which had never lived outside the suburb in which they'd been born.
At the same point in time, inviting an established friend to hang out felt incredibly risky to me because of a rather specific type of rejection-averse social anxiety that I suffered from for years. I'm glad I made myself take that risk over and over again, because it really did cure me of that problem.
Nice post Chris. The risk I'm thinking about is taking a university class in data science this year. As a writer, the idea of developing more technical skills is a bit of a jump, but I'm excited about it!
I do enjoy reading your posts one of the things I would like to take a risk on is volunteering to read your articles ahead of time to point out spelling errors. It is risk-averse not risk adverse.
I am currently a software developer and attention to detail is very important to me. Also, for quite some time now, I have wanted to write a novel myself. It isn't that I am risk-averse it is that I don't believe in myself. I've taken many risks in life, not the least of which was having four children.
Thank you for inspiring me to take more risks at the age of 55!
Updated to risk-averse! Sorry, I guess I took too much of a risk on that one. 😆
I love this idea of writing a novel for you. It’ll use 100% of your brain, passion and research abilities. I think you’ll grow as a person and once finished, you’ll feel tremendous satisfaction checking this box. Maybe you can pretend every month is November—nanowrimo? I just might have to steal your idea and contemplate a novel of my own so I can deep research a subject that interests me.
Whoa, Chris! So much news! My risk? Writing the book about my incredible grandparents and their trip to Alaska! I look forward to catching up with you IRL. Have fun in Singapore, which I recall was HOT AS HELL!
Chris, I quote you at least once a month "ideas are great ideas with action are better" from your book the $100 Start Up. Sometimes the idea with action might be a risk but I would say not taking that risk comes at a higher cost!? I still continue with my side hustle as it's great doing something arty for my mental health while making $1000 a month. I have the links to my side hustle school episodes on my email signature. Last year I skied in Canada, snorkeled with turtles with my wife in the Cook Islands and did a road trip through Idaho, Montana and Wyoming so I could fly fish the Snake River in Jackson Hole WY with a friend, a lifetime objective. All of last years adventures were travelling with and often staying with friends to keep the cost reasonable and stay connected. Ngã mihi Martin
https://sidehustleschool.com/episode/812/
https://sidehustleschool.com/episode/1755/
Chris, your rainstorm story immediately reminded me of when I lived for a year on a little Micronesian island, and the drenching, extraordinarily sheeting rain that would fall, sometimes suddenly. More than once I was caught on the little scooters we drove there, and soaked head to toe. (Living on a tiny island was one of the risks I took.)
This year, by hook or crook—or with the help of crooks—I'm going to publish my memoir of my truly lunatic near-40-years correspondence with the Jack Daniel's distillery. The draft is written but as you know, that's a far winding mile to actually publishing. Thanks for the post!
My big risk for this year is releasing a book. I hope to have it available for purchase by the end of this year. Currently working on converting it into an ebook that I can send to beta readers.
Very exciting!
Taking an in person memoir class and writing about intensely personal things. Surprisingly daunting.
Writing memoir is soo tough. I mean sometimes I can be absolutely great, freeing, healing, but then other times, you're just in the muck of it and just reliving without knowing how to relive better or gentler or in ways that won't just rip you apart again. Be easy on yourself through the process!
Thanks again for the great article Chris!
Showing up in person
This ONE action has been so worthwhile from both a personal connection and professional opportunity perspectives!! ♥️
I go with a spirit of gratitude (I GET to be here 🙏), humility, curiosity and heart (who I am authenticly).
The heavens have opened and showered me with Amazing experiences more than once. Go Be Open and Yourself Serve/Be helpful and grateful
My advice :)
Not sure what risk I’ll take yet, but I’d definitely like to figure out how to have someone on my very technologically unskilled podcast OR guest on someone else’s (which may be safer tech-wise). I’d just like to put myself out there to talk about being a decluttering expert & helping those with ADHD like me.
Last year, I challenged myself to do 3 public speaking events. I gave 4 presentations & am now looking to do more. That’s a win! 🏆
❤️
Reading this in the quiet morning hours and realizing: some of the most beautiful chapters of my life began with a tiny whisper—“Just try.”
I moved to a new city on a gut feeling once. Said yes to a mentorship I wasn’t sure I was ready for. Wrote a book I thought no one would care about. Each time, I risked looking foolish. Each time, I came out changed.
Right now, my small risk is putting more of my truth out there—through writing, art, voice. Not trying to be perfect. Just honest.
Thanks for reminding me that uncertainty is often just the front door to the good stuff.