#120 | 30 Years on Earth: 11 Habits That Shaped My 20s
A collection of the best hidden gems, mental models, and frameworks from the world’s top thinkers; to help you become 1% better and live a happier life ❤️
Hello curious minds 🧠
Just reached my 30th year on earth this week! 🎉
I do like the good classic "30 lessons in 30 years" post. Honestly, I get it.. it’s a good way to reflect on the last decade. I will probably do one at some point but I want to spend more time thinking about it.
In the meantime, I thought another good way to look back on my 20s is by sharing the key habits that shaped who I am today; the ones that brought me so much joy and growth but also came with their own challenges.
Some habits made me more productive but they also made me a little too rigid. Others helped me plan for the future, but at times, they made me overthink things…
Regardless, I love my habits ❤️ Both the goods and the challenges :)
So, I hope you enjoy my habit list below and take whatever resonates with you. Maybe some will inspire you, or maybe you will just get a good laugh at my trial and error 😄
🚀 If you are new here…
Hi, I’m Ryan 👋🏼 I am passionate about lifestyle gamification 🎮, which it’s just a fancy way saying I approach life like a video game, designing my character intentionally, and strive to level up every day. I am obsesssssssss with learning things that can help me live a happy and fulfilling life.Every Sunday, through The Limitless Playbook newsletter, I share 1 actionable idea from the world's top thinkers 🎯
Oh, and fun fact: I am a PhD candidate in AI 👻 I am deeply interested in how AI can help us 10x the way we live, learn, and thrive; so expect me to share some cool AI tools, insights, and research 🤖
🧠 11 Habits That Shaped My 20s
I have experimented with a lot of habits in my 20s… some stuck, many didn’t. For this list, I am only focusing on the ones I have consistently followed for at least a year.
⚙️ Habit 1 and 2: Exercise + 5am (on avg.) Club (10+ years)
🍀 How the habit started?
These two habits are the first I built consciously when I was around 19 / 20. At the time, I was doing my year-long work placement while also studying for a qualification. And so my entire day was spent sitting, at work from 9 - 5 and then again in the evenings to study.
Within a month or two, I was out of shape and felt terrible. I knew I needed to change. I had played basketball for years and so being active was important to me.
The problem was no time…
Evenings were packed with studying, and I was too drained to work out afterward.
The only solution was to wake up earlier. And that’s how I started going to the gym in the mornings and joined the 5am Club.
🍀 How it has changed my life?
Gym and 5am club gave me a strong boost in confidence and self-belief. My body transformed fast as I went from barely working out to 5 - 6 times a week.
The 5am club meant I had “more time” throughout the day.
My day has three segments instead of two like most people:
5am - 8am (first segment)
8am - 6pm (second segment)
6pm - bedtime (third segment)
By waking up at 5am, I created an extra part of my day that most people don’t have and over time, that extra block allowed me to get ahead, whether it was working out, reading, or just thinking.
🍀 Do I still do the habit?
Yes… but not exactly the same way.
I will be working out for life. But the way I train has changed over the years; from bodybuilding and powerlifting to bouldering and climbing to now practicing Brazilian Jiu-Jitsu (BJJ).
If you don’t exercise at all, start with the gym.
If you have been training for a while, I highlight recommend martial arts, specifically BJJ, judo, or wrestling.
There’s nothing that feel more confident and reassuring than to walk around the world and into most rooms knowing that you can handle yourself against any physical confrontations.
In terms of the 5am club habit, I am not sure if I would strongly recommend it to anyone.
The real magic isn’t in waking up at 5am… it’s in how you use your time when you are awake. You are not actually getting “more” time. You are simply making better use of your time. By waking up early, you automatically shift your unproductive time at night to productive time in the morning (unless you are a night owl).
For me, I still love waking up in the early morning as I find it to be the best time to focus.. The world is quiet, there are no distractions, and I start the day feeling ahead. But I don’t push the 5am rule on myself anymore if that means sacrificing sleep. Sleep is a very important component to health.
Use the 5am club habit cautiously.
⚙️ Habit 3: Knowledge Management (7+ years)
🍀 How the habit started?
Back in 2018, when Notion was just a few years old, I stumbled across it during my productivity research. I have always loved organising things and learning new things but I never had a smart way to keep track of everything.
That’s when Notion comes in.
It wasn’t just a simple note-taking app. It was a user-friendly interface to what is basically relational databases in computer science. I realised Notion is a key tool to good knowledge management, which it’s an important meta-skills that’s a multiplier in many things in life.
I was so excited about it that I started introducing Notion to my friends. My common pitch was:
If you use Notion well, you can easily experience 2 - 10x your return on effort in whatever you do or learn.
🍀 How it has changed my life?
For me, it was never about using Notion. It was about developing a good system to manage knowledge.
My knowledge management system helps me:
Remember what matters from the 200+ books I have read
A place to connect ideas from the different things I have read
Surface key relevant insights at the time I need it the most
It made learning feel worth it because I wasn’t just consuming information.. I was actually thinking about how future Ryan can easily access those information when he needs to.
This habit is what finally got me to read consistently.
🍀 Do I still do the habit?
100%. And it’s only getting more useful.
You can now easily layer AI on top of your personal knowledge base, making it even easier to find, recall, and apply what you have learned.
Personal knowledge management is becoming more important as it acts as the foundation source of which AI can expand upon.
⚙️ Habit 4: Lifestyle Gamification (9+ years)
🍀 How the habit started?
This habit has always come naturally to me… I just didn’t have a clear system for it in the beginning.
Then Notion came along (you will start to see how many things was made possible with tools like Notion)
At first, I was using it for knowledge management. But very quickly, I realised it could do much more. It could help me design my life or what I like to call Lifestyle Gamification.
Before Notion, I was already doing this in a loose way but with it, I started creating structured systems; systems to connect my vision to my daily actions. At one point, I was spending more time building these systems than actually using them 🙈 But over time, things settled, and my system became something I could rely on every day.
🍀 How it has changed my life?
What’s the best way to put this…
You know how when you start a project, people tell you to set SMART goals? Now imagine having a macro view of all your SMART goals; how they connect, how they move you toward a vision, and how they work together like puzzle pieces.
That’s what Lifestyle Gamification did for me.
I have a clear connection between my long-term vision and my daily actions.
Every project and every task had a purpose.
I was able to move fast because I was very clear where I am going and how I am getting there.
🍀 Do I still do the habit?
Absolutely.
This is one of the most personal and powerful habits I have. It’s my secret weapon; something I do naturally and use tools to make even better.
Over the years, my Notion setup has evolved. It started of complex and heavy but now I have simplified it using the 80/20 rule. My current setup is just my vision palace, my knowledge library (second brain), and my action list (using the calendar timeboxing habit).
This habit isn’t for everyone, but for me, it makes life exciting and full of purpose.
⚙️ Habit 5: Reflection (7+ years)
🍀 How the habit started?
My productivity journey started with a book: The 12 Week Year by Brian P. Moran and Michael Lennington. If you want to get more done in less time, I highly recommend it. The biggest lesson I took from it is:
Reflection is the key to fast progress.
Some people call this the “scientist mindset”; constantly testing, adjusting, and improving.
The whole “10,000 hours to become an expert” is flawed. Doing 10,000 hours of the same thing won’t make you great. 10,000 hours of doing + reflection is what makes you become better. Reflection is the key part.
Oh you made decision X. Did it work out? If not, why?
Oh you tried a new habit. Do you actually like it? If not, what’s missing?
🍀 How it has changed my life?
Reflection is what makes progress feel like a superpower.
It’s how I went achieved V6 / V7 in bouldering within 6 months.
It’s how I speed up learning, focusing on what really matters.
It’s how I learn what I want (and don’t want) in a life partner.
I believe we all want to be happy. But figuring out what actually makes you happy is a both an easy and difficult question to answer. The only way to know is to try things, reflect, and adjust.
Right now, my reflection process happens weekly, quarterly, and annually. And because of it, I have become more self-aware in every area of my life.
🍀 Do I still do the habit?
If you reflect often, the cost of wrong decisions becomes smaller.
1000% YES.
Action is working hard.
Reflection is working smart.
You need both.
Reflection is the seed for change; to move towards the direction of living a happier life. Each reflection comes with a decision; a decision to become better.
And for me, that makes reflection a priceless habit.
⚙️ Habit 6: AI (7+ years)
🍀 How the habit come about?
It came from Habit 5 💡
After finishing my year-long work placement in finance, I had a realisation…
I wasn’t excited about it…
I asked myself: Is this it?
I reflected on the whole year.. to search for moments that actually excite me.
One moment stood out.
It was when I used VBA to automate an internal process, cutting the time it took by over 80%!
That’s when I knew (and remembered).
I loved building things, especially things that improve human ability.
But there was one problem: my Economics degree didn’t teach me how to build. So, I made a bold decision.
I quit my graduate job.
Moved back home.
And in November 2017, I coded 12 hours a day, every single day.
By the end of the month, I had spend 360 hours of coding. I did everything... courses, projects, blogging to track progress, you name it.
It was during this time that I discovered and fell in love with Natural Language Processing (NLP).
Why NLP? My thinking was simple.
The world is built on language (text); books, articles, conversations, even videos and podcasts can be converted into text. I love learning, and I realised that if I got good at teaching machines to understand human language, I could build something that helps me (and others) learn faster.
This passion led me to pursue a PhD in Knowledge Graphs & NLP later on.
In December 2017, I applied for jobs and masters degree in Computer Science. In the same month, I…
✅ Got a job offer at a startup to start immediately.
✅ Got into Imperial College London for an MSc in Computing (starting Oct 2018).
✅ Already secured a graduate tech offer for September 2018 (deferred to September 2019).
That’s how my tech career began.
🍀 How it has changed my life?
I am happier, more fulfilled, and more empowered.
Most of the time, my work feels like play. It’s what I had do in my spare time anyway. It feels like I found one of my real-life video games.
Building things aligns perfectly with who I am. That means I wake up excited, which is something not everyone gets to say about their work.
Another huge upside with coding is freedom & flexibility. Because of coding, I can work remotely and from anywhere in the world; something that’s not possible in many professions.
And for that, I feel very grateful.
🍀 Do I still believe in the habit / carry on with the habit?
Yes, as long as it helps me build things.
I love building things and coding is just a tool that helps me do it.
With AI and large language models (LLMs) evolving, some people wonder if AI will replace coding?
I don’t think so.
Coding will change, and the role of AI engineers will shift, but it will still be in demand… probably even more so than ever. Because as AI advances, we need more people who know how to integrate it into industries, businesses, and everyday life.
⚙️ Habit 7: Writing (5+ years)
🍀 How the habit come about?
As a kid, I always loved the idea of starting my own blog website :) but the habit never really stuck.
That’s until November 2017.
When I switched to computer science, I wanted a place to document my learning journey; to track my progress, take notes, and showcase my projects.
So, I launched a blog website called UnsupervisedLearning… because, well, I was learning with no supervision 😄
But once I started my job in December 2017, the writing stopped. I was too focused on coding.
Fast forward to December 2019, during my year-end reflection, I realised that I was learning and coding every single day, but there was no way to showcase it.
At the time, I was about to start applying for PhD, and I thought: Why not track my learning journey while preparing for PhD applications?
So in 2020, I started NLP365, a growth project where I blog about NLP every single day for 365 days (or 366, since it was a leap year). That blog ended up being the key driver behind my PhD offer and multiple job offers that more than doubled my salary at the time.
Since 2021, I have been writing this newsletter you are reading now. It’s gone through a few rebrands, but the core theme has always been the same:
🧬 Share the best ideas, mental models, and insights from the world’s top thinkers; so we can apply them and live a happier, more fulfilling life.
🍀 How it has changed my life?
Writing has done three things for me:
It forces me to slow down — I read a lot of books, but writing makes me revisit them, process them properly, and take away key lessons I want to remember
It helps me understand things better — Explaining something in writing forces me to clarify my own thoughts
It helps me develop and refine ideas — Some of my best insights have come from writing them down and fleshing them out
In 2024, I even started writing for DataCamp, giving my AI-related writing a home. Looking back, none of this would have happened if I hadn’t made writing a consistent habit.
🍀 Do I still believe in the habit / carry on with the habit?
Absolutely.
Writing helps you think better.
For me, writing is also about leaving a record; a way for my future self (and maybe even my future family) to look back and see how I thought, what I believed, and what I was learning at different points in life.
That’s why I am passionate about content creation in general: writing, YouTube, podcasts… because these things don’t disappear. They live on as a time capsule for the future.
So hello my future kid 😊 If you are reading this, just know that right now, I am going through a challenging time. You can ask me more about it but the fact that you are reading this means I have conquered the challenge. Also, your mum is currently lying next to me in bed, happily snacking on raisins and cranberry as I am writing this… ❤️
Also your mum wants me to add that she’s not just snacking but reading the Cognitive Behaviour Therapy book by Judith Beck; to become an amazing therapist that I know she will become 🧠
⚙️ Habit 8: Reading (5+ years)
🍀 How the habit come about?
Not going to lie, I get funny feeling with non-fiction books. Every book is so exciting to me because it represents a new way of thinking that could literally change who you are!
But I had a problem.
Like many people, I thought to myself: What’s the point of reading so many books if a) I don’t remember them? and b) I don’t have a way to find the key insights when I need them?
That all changed when I started using Notion for knowledge management.
With Notion, I can track ideas, revisit key lessons, and actually apply what I have learned.
Fast forward to today, I have read 150+ books, with 50+ re-reads, averaging 50+ books per year for the last four years.
🍀 How it has changed my life?
Reading has completely changed how I see the world.
I have read books on entrepreneurship, productivity, life design, relationships, psychology, therapy, product management, philosophy, health, diet, finance, and others.
What I love most about reading is that it broadens my thinking beyond just business, technology, and AI.
For me, reading non-fiction isn’t about just gathering random knowledge.. it’s about learning what I need to learn to live a happier, more fulfilling life.
🍀 Do I still believe in the habit / carry on with the habit?
YES!
I see this habit the same way I see exercise; it’s something I’ll never stop doing.
One thing I have been working on behind the scene is the One Hundred Book Index; a personal collection of the 100 best books I have ever read across different topics. These are the books I want to revisit over and over again and the ones I had encourage my kids to read one day.
To build this list, I need to keep reading. If I assume only 10% of the books I read will make the cut, I will need to read at least 1,000 books… and honestly, even that percentage might be too high.
But that’s the beautiful part about reading: you never know which book will change your life until you pick it up!
⚙️ Habit 9: Calendar Timeboxing (3+ years)
🍀 How the habit come about?
As I moved away from complex setups toward a more minimalist approach, I only included the things that has worked well for me
One of the habits that worked well is Calendar Timeboxing.
The idea is simple. Treat your calendar like a to-do list. But instead of just writing down tasks, you schedule exactly when you will do them. This is called "execution intention", and it makes a huge difference.
When you timebox tasks…
You will know exactly when you will work on them.
You will know the capacity of your day before it starts.
You will get things done faster because there’s a set time for it.
🍀 How it has changed my life?
This one habit has increased my daily productivity the most. My daily action system has boiled down to just calendar timeboxing.
Going back to action is work hard and reflection is work smart.. my daily action is solely supported by my calendar timeboxing.
🍀 Do I still believe in the habit / carry on with the habit?
Yes, for now. I have been doing this consistently for 3+ years now and it has been working wonderfully. I don’t see a reason to change it up. At least until I discover a better way of doing things.
⚙️ Habit 10: Mental Health / Therapy (3+ years)
🍀 How the habit come about?
When I was 27, I went through a tough breakup. It left me confused. I didn’t fully understand what had happened or why I felt the way I did.
So, like any problem, I turned to books for answers.
I read around 15+ relationship books, searching for clarity. Then I finally found one book that made it clicked for me: How to Do the Work by Dr. Nicole LePera.
It was hands-down one of the best books I have ever read on relationships, therapy, and self-healing.
At the same time, I decided to start therapy and life coaching. Since then, I have done one-on-one therapy, group therapy, and explored different therapy styles.
🍀 How it has changed my life?
Therapy took my habit of reflection to a whole new level.
For me, a good therapist or coach doesn’t just listen; they challenge you, guide you, and help you see things from a completely different perspective.
This is especially true when you are exploring how your childhood has shaped who you are today.
The truth is, we all get stuck in our own stories. But a therapist who truly understands you can help you break free from limiting beliefs, see alternative perspectives, and explore paths you wouldn’t have found on your own.
I am very grateful that I found a therapist I connected with early on — it made all the difference.
🍀 Do I still believe in the habit / carry on with the habit?
Yes x1000.
There’s a saying: "Everyone needs therapy—it’s just a matter of whether they realize it yet".
Think about it:
You wouldn’t wait until you are unhealthy or out of shape to start exercising...
The same goes for mental health.
Sadly, many people (and couples) only seek help when things get really bad. But therapy isn’t just about fixing problems; it’s about prevention, it’s about staying mentally strong, it’s about being emotionally aware, and more.
You exercise to stay fit.
You do therapy to stay mentally healthy.
Take care of your mind the way you take care of your body ❤️
⚙️ Habit 11: Curiosity of The World and Life (10+ years)
🍀 How the habit come about?
Honestly, I don’t know.
This is just who I am.
To learn is to be curious in the first place. And my curiosity has been very high from the beginning. And I am, again, grateful for it.
I am not curious about everything… only about things I find useful to live a happy life.
I want to learn how to live a happy, freaking cool, and story-worthy life.
I want to explore what the world has to offer.
I want to become someone who can protect and provide for the people I love.
I like the idea of becoming a renaissance man but for life; learning everything I need to know to become the best version of myself and create a life that’s worth remembering.
🍀 How it has changed my life?
This habit is the root of everything.
Every other habit I have mentioned above: reading, writing, fitness, therapy, productivity… all came from this deep curiosity about how to live better.
🍀 Do I still believe in the habit / carry on with the habit?
This is who I am and probably who I will always be.
I don’t know how to teach curiosity to someone else. But I do know that protecting my own curiosity is one of the most important things I can do.
It’s one of the greatest gifts my parents have given me, and I hope to hold onto it for a lifetime. ❤️
I am always curious about what others are passionate about and what they are currently working on. Hit reply and share what’s been keeping you busy these days. I would love to learn!
With love,
Ryan O. 🎮
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