Reading this with just 11 days until my 38th birthday, and I’ve finally decided to make the leap into full-time digital nomad life. I tested it during the pandemic and felt more alive and accomplished than ever—but I clung to the security of my corporate job and comfort zone.
Now? I’m scared as hell—but I know this leap is necessary.
Appreciate this post, Dan. The timing couldn’t be better.
Wow, first off, massive respect for making that leap. That kind of fear usually means you’re headed in the right direction. I’m 25, but I’ve been reflecting a lot lately on how scary yet essential these inflection points are.
As someone who recently hit 31, I can attest to a lot of these things, in myself and my friends. Especially in the ”1%” field or what I think of in terms of the Shawshank quote ”get busy living, or get busy dying”.
Please, please, please: get busy living, because if you don’t, you’ll by default be dying. A slow, unnoticable death by a thousand fears, regrets, coulda-shoulda-wouldas. Some of my friends have woken up to this, others have not.
Don’t be too hard on yourselves, allow failure into your life, but do not identify with the failure. Your company failed, you succeeded in learning how NOT to run a company.
Allow yourself to find what you are good at, work on it and passion will follow.
This is powerful. That Shawshank line always hits, and your reminder about not identifying with failure really stuck with me. I’m 25 and just starting to notice how easy it is to sleepwalk through your 20s if you’re not careful.
I recently jotted down a list of “25 things I’m starting to understand” , small truths I’ve picked up while trying to figure out what getting busy living actually looks like at this age. Might resonate:
I remember setting the goal of earning 100k in a year and while that was more than double what I was already earning... my mind got to work figuring out how I would go about the task.
At the end of the year my income totalled 140k which was mind blowing to me.
Love this, it’s wild how setting a number flips the brain into creative overdrive. That mindset shift alone is something I’m just starting to grasp.
I’m 25 and wrote a piece recently about the things I’m starting to understand, not just about goals and money, but how identity, fear, and clarity shape everything. You might dig it:
Felt this. That pressure to “figure it all out” in your 20s can be paralyzing, but reframing it as a setup phase instead of a failure hits different. I’ve been leaning into that same mindset lately: explore, mess up, reflect, repeat.
I actually just wrote something along those lines, a piece called “25 Things I’m Starting to Understand” from the perspective of being 25 and deep in that process. My Substack, Present & Progressing, is all about documenting growth, creativity, and identity in real time, might resonate:
Dan...another genius article. Thank you for saying, "You don't need to be perfect, but realize that most people never make a conscious decision in their lives." For me, 20-30 was a wonderful, wild, messed-up, dangerous, and liberating time. I celebrated another birthday yesterday. I now have 50 years of wisdom on top of the time you discuss here. Thinking for myself and stepping out of the matrix into 100% on me choices was right for me. One precious life. That's all we get.
I’m glad so many people saw merit and wisdom in this article but I didn’t. I think there a lot of nuance in what people have the access to do in their youth or in any part of their life. Quality of life is determined by the person living it, not some idea of what others think.
Some of your points are valid for anyone regardless of age.
It’s always interesting to see people say “you should do x by this age” or my favorite line is “they want you to be infertile”.
Truly none of this is so disconcerting that those who aren’t doing this will be mad unless they regret not doing this and had the chance to do so.
I just wish that people would tell people to be unafraid to do what’s best for you and to learn what’s best for you and your goals and not all this “advice”.
Totally get where you’re coming from, not everyone has the same runway, resources, or starting point. I think the loudest advice often misses that nuance.
I’m 25 and just wrote a piece that leans more into reflection than prescription, called “25 Things I’m Starting to Understand.” It’s less “do this” and more “here’s what I’m learning, imperfectly, in real time.”
If you’re into honest, evolving perspectives over rigid advice, it might resonate:
Love that, this is the kind of message that stays with you long after you read it. I’m 25 and recently wrote something along those lines, called “25 Things I’m Starting to Understand.” It’s a reflection on growth, identity, and learning to navigate life in your 20s, might be a good complement for younger folks just starting to figure it out.
Years ago, when I was at the brink of my quarterlife crisis and burnout, I gathered up all my courage to create a 25 by 25 list. A compilation of all things I wanted to achieve that made me feel insane and psychotic.
Of course, I never did achieve all 25 things in that list in that year. Some things I started and some I never tried at all.
Fast forward five years later, I realized I'd crossed off most things on that list, and would soon be working on the others.
Big goals don't always sound practical, but it is the passion of curiosity that brings you closer and closer each time you try.
This is such a refreshing take, the honesty about not hitting everything right away, but still making your way toward those goals over time, really resonates. That gap between intention and action can feel like failure in the moment, but looking back, it’s often where the quiet momentum lives.
I’m 25 now and just wrote a piece called “25 Things I’m Starting to Understand”, a mix of realizations around ambition, burnout, and the long game of becoming. It’s not about doing everything at once, but staying open and curious enough to keep going.
Powerful message — raw, unfiltered, and deeply necessary for those ready to hear it. There’s a lot of hard truth in here that most people spend years avoiding. Not everything will land for everyone, but that’s the point — this isn’t for the average. It’s for the few willing to take radical ownership of their lives. Respect for putting this out there.
Exactly this, it won’t land for everyone, but it’s not supposed to. Radical ownership isn’t comfortable, but it’s the only way forward if you’re serious about building a life that’s actually yours.
I’m 25 and have been writing about what it feels like to step into that process. Just dropped a piece called “25 Things I’m Starting to Understand”, not a blueprint, more like honest notes from someone mid-transformation. Might resonate with others walking the same path:
My goals have always been big right from when I was little,I never liked settling for less,to the extent that when ever I set a goal I am always scared of that goal but I work towards it
Yes! Sometimes all it takes is one post to flip the switch. Starting is the hardest part, but once you’re in motion, everything changes.
I’m 25 and just wrote a piece reflecting on the exact kind of shift you’re talking about, called “25 Things I’m Starting to Understand.” It’s a list of the small, messy, real things I’m learning while trying to figure life out in motion.
Recently I sat down with an old friend who's searching for more purpose in life.
He told me he thinks that after a certain threshold, money doesn't add to your life. Going out for nice dinners would get old, he said. Going on relaxing vacations would become boring.
In his mind, this was news to me, and a rebuttal to my goals of making millions of dollars.
I said that this is only true for people who aren't driven by a larger purpose than escaping wage slavery. If you think your goal is to work less so you can enjoy being lazy and eating food, then of course the achievement of making millions seems shallow and unsatisfying.
I realized then that someone who hasn't found any deeper spiritual calling simply cannot comprehend the many-layered reasoning for my lofty money goals. They're doomed to misinterpret me as being driven purely by status. They'll think I want money so I can just live in luxury and look cool.
It's hard for me not to see that as pathetic at this point.
I'm not going to spend any time justifying myself to people without meaningful goals. Even if I tried to explain the larger vision behind what I'm aiming at, they'll hear it through a filter and still think it's coming from the same motives that are driving them: Survival and status, and the negation of challenge.
Negation of challenge? That's the most absurd goal of all. Even a video game addict at least unconsciously knows that challenge is really what they want.
Sorry, I thought it seemed like you were making a sarcastic remark.
Yes, my spiritual calling and higher purpose creations could be further leveraged with substantial funding.
Purchasing property to actualize my vision of permaculture food forests, feeding the truly starving, and creating educational and healing resources for the hungry to learn to fish (metaphorically).
Reading this with just 11 days until my 38th birthday, and I’ve finally decided to make the leap into full-time digital nomad life. I tested it during the pandemic and felt more alive and accomplished than ever—but I clung to the security of my corporate job and comfort zone.
Now? I’m scared as hell—but I know this leap is necessary.
Appreciate this post, Dan. The timing couldn’t be better.
Wow, first off, massive respect for making that leap. That kind of fear usually means you’re headed in the right direction. I’m 25, but I’ve been reflecting a lot lately on how scary yet essential these inflection points are.
Just wrote down 25 things I’m starting to understand at this stage in life, not advice, more like field notes from the messy middle. A few might resonate with where you’re at now, especially around fear, identity, and momentum: https://open.substack.com/pub/presentandprogressing/p/25-things-im-starting-to-understand?r=5fso73&utm_medium=ios
Cheering you on as you step fully into that freedom ✌️
As someone who recently hit 31, I can attest to a lot of these things, in myself and my friends. Especially in the ”1%” field or what I think of in terms of the Shawshank quote ”get busy living, or get busy dying”.
Please, please, please: get busy living, because if you don’t, you’ll by default be dying. A slow, unnoticable death by a thousand fears, regrets, coulda-shoulda-wouldas. Some of my friends have woken up to this, others have not.
Don’t be too hard on yourselves, allow failure into your life, but do not identify with the failure. Your company failed, you succeeded in learning how NOT to run a company.
Allow yourself to find what you are good at, work on it and passion will follow.
This is powerful. That Shawshank line always hits, and your reminder about not identifying with failure really stuck with me. I’m 25 and just starting to notice how easy it is to sleepwalk through your 20s if you’re not careful.
I recently jotted down a list of “25 things I’m starting to understand” , small truths I’ve picked up while trying to figure out what getting busy living actually looks like at this age. Might resonate:
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Appreciate you sharing your perspective!
I can testify to the big goals aim.
I remember setting the goal of earning 100k in a year and while that was more than double what I was already earning... my mind got to work figuring out how I would go about the task.
At the end of the year my income totalled 140k which was mind blowing to me.
It's time to set some bigger ones.
Awesome letter as always chief 👌
Love this, it’s wild how setting a number flips the brain into creative overdrive. That mindset shift alone is something I’m just starting to grasp.
I’m 25 and wrote a piece recently about the things I’m starting to understand, not just about goals and money, but how identity, fear, and clarity shape everything. You might dig it:
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Here’s to even bigger goals 🔥
I'm in my 20s and this took so much pressure off “figuring it all out”.
Makes me want to explore, mess up, and build slow, knowing it’s all part of the setup, not the failure.
Felt this. That pressure to “figure it all out” in your 20s can be paralyzing, but reframing it as a setup phase instead of a failure hits different. I’ve been leaning into that same mindset lately: explore, mess up, reflect, repeat.
I actually just wrote something along those lines, a piece called “25 Things I’m Starting to Understand” from the perspective of being 25 and deep in that process. My Substack, Present & Progressing, is all about documenting growth, creativity, and identity in real time, might resonate:
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Glad to know others are on this path too. Keep going!
Dan...another genius article. Thank you for saying, "You don't need to be perfect, but realize that most people never make a conscious decision in their lives." For me, 20-30 was a wonderful, wild, messed-up, dangerous, and liberating time. I celebrated another birthday yesterday. I now have 50 years of wisdom on top of the time you discuss here. Thinking for myself and stepping out of the matrix into 100% on me choices was right for me. One precious life. That's all we get.
I’m glad so many people saw merit and wisdom in this article but I didn’t. I think there a lot of nuance in what people have the access to do in their youth or in any part of their life. Quality of life is determined by the person living it, not some idea of what others think.
Some of your points are valid for anyone regardless of age.
It’s always interesting to see people say “you should do x by this age” or my favorite line is “they want you to be infertile”.
Truly none of this is so disconcerting that those who aren’t doing this will be mad unless they regret not doing this and had the chance to do so.
I just wish that people would tell people to be unafraid to do what’s best for you and to learn what’s best for you and your goals and not all this “advice”.
Most people saw hope in it.
And hope is the hardest drug to quit.
True
Totally get where you’re coming from, not everyone has the same runway, resources, or starting point. I think the loudest advice often misses that nuance.
I’m 25 and just wrote a piece that leans more into reflection than prescription, called “25 Things I’m Starting to Understand.” It’s less “do this” and more “here’s what I’m learning, imperfectly, in real time.”
If you’re into honest, evolving perspectives over rigid advice, it might resonate:
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Appreciate your take, we need more of this kind of balance in the conversation! 😄
Wise as ever Dan.
Some people need a wake-up call, including myself from time to time.
Spot on again Dan! This is one post I will share with my children.
Love that, this is the kind of message that stays with you long after you read it. I’m 25 and recently wrote something along those lines, called “25 Things I’m Starting to Understand.” It’s a reflection on growth, identity, and learning to navigate life in your 20s, might be a good complement for younger folks just starting to figure it out.
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Dan’s post definitely feels like one to pass on!
Mediocrity is so normalized that I am suffocating.
This is such a wonderful piece.
Years ago, when I was at the brink of my quarterlife crisis and burnout, I gathered up all my courage to create a 25 by 25 list. A compilation of all things I wanted to achieve that made me feel insane and psychotic.
Of course, I never did achieve all 25 things in that list in that year. Some things I started and some I never tried at all.
Fast forward five years later, I realized I'd crossed off most things on that list, and would soon be working on the others.
Big goals don't always sound practical, but it is the passion of curiosity that brings you closer and closer each time you try.
This is such a refreshing take, the honesty about not hitting everything right away, but still making your way toward those goals over time, really resonates. That gap between intention and action can feel like failure in the moment, but looking back, it’s often where the quiet momentum lives.
I’m 25 now and just wrote a piece called “25 Things I’m Starting to Understand”, a mix of realizations around ambition, burnout, and the long game of becoming. It’s not about doing everything at once, but staying open and curious enough to keep going.
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Your 25 by 25 list sounds like it gave you way more than a checklist 😄🙌🏻
Powerful message — raw, unfiltered, and deeply necessary for those ready to hear it. There’s a lot of hard truth in here that most people spend years avoiding. Not everything will land for everyone, but that’s the point — this isn’t for the average. It’s for the few willing to take radical ownership of their lives. Respect for putting this out there.
Exactly this, it won’t land for everyone, but it’s not supposed to. Radical ownership isn’t comfortable, but it’s the only way forward if you’re serious about building a life that’s actually yours.
I’m 25 and have been writing about what it feels like to step into that process. Just dropped a piece called “25 Things I’m Starting to Understand”, not a blueprint, more like honest notes from someone mid-transformation. Might resonate with others walking the same path:
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Appreciate voices like yours calling it like it is!
My goals have always been big right from when I was little,I never liked settling for less,to the extent that when ever I set a goal I am always scared of that goal but I work towards it
I can't believe this - this is my sign to start!!
Yes! Sometimes all it takes is one post to flip the switch. Starting is the hardest part, but once you’re in motion, everything changes.
I’m 25 and just wrote a piece reflecting on the exact kind of shift you’re talking about, called “25 Things I’m Starting to Understand.” It’s a list of the small, messy, real things I’m learning while trying to figure life out in motion.
https://presentandprogressing.substack.com/p/25-things-im-starting-to-understand
Rooting for you, go build something great!
Recently I sat down with an old friend who's searching for more purpose in life.
He told me he thinks that after a certain threshold, money doesn't add to your life. Going out for nice dinners would get old, he said. Going on relaxing vacations would become boring.
In his mind, this was news to me, and a rebuttal to my goals of making millions of dollars.
I said that this is only true for people who aren't driven by a larger purpose than escaping wage slavery. If you think your goal is to work less so you can enjoy being lazy and eating food, then of course the achievement of making millions seems shallow and unsatisfying.
I realized then that someone who hasn't found any deeper spiritual calling simply cannot comprehend the many-layered reasoning for my lofty money goals. They're doomed to misinterpret me as being driven purely by status. They'll think I want money so I can just live in luxury and look cool.
It's hard for me not to see that as pathetic at this point.
I'm not going to spend any time justifying myself to people without meaningful goals. Even if I tried to explain the larger vision behind what I'm aiming at, they'll hear it through a filter and still think it's coming from the same motives that are driving them: Survival and status, and the negation of challenge.
Negation of challenge? That's the most absurd goal of all. Even a video game addict at least unconsciously knows that challenge is really what they want.
Your spiritual calling let you to the achievement of making millions?
^ See, already we have someone trying to bait me into justifying it! 😁
How so? It was a clarifying question.
Sorry, I thought it seemed like you were making a sarcastic remark.
Yes, my spiritual calling and higher purpose creations could be further leveraged with substantial funding.
Purchasing property to actualize my vision of permaculture food forests, feeding the truly starving, and creating educational and healing resources for the hungry to learn to fish (metaphorically).
Loved this one.
Thank you for such incredible wisdom. It was so lovely reading this and you spoke straight to me. I really like the content you put out.