34 Lessons From 34 Years of Building, Breaking, and Becoming
I turned 34 last Saturday. There was no big celebration—just a quiet lunch with my wife, a long walk, and some reflection.
If I could sit down with my younger self, this is what I’d tell him. Not the motivational poster version, but the real, earned stuff—the things I had to unlearn, re-learn, and still remind myself of every day.
Here are 34 lessons from 34 years.
You can’t brute-force your way through confusion. When you know what matters, energy flows where it should. Clarity saves you from burning out on the wrong things.
You can earn back money, but not energy. Guard it. Invest it in people, projects, and habits that give more than they take.
You’re not always unmotivated—you’re tired, overstimulated, or disconnected. Fix your inputs before blaming willpower.
Rushing creates friction. Friction causes mistakes. Take the time to do it right once, instead of redoing it twice.
Anyone can act fast under pressure. Few can stay calm. When you’re calm, you see clearly. And clarity always wins.
Good habits, relationships, and reputation—they all multiply over time. The same goes for bad habits, toxic relationships, and a negative reputation. Be careful what you let compound.
Success isn’t about intensity; it’s about consistency. And consistency comes from sustainable systems. Trust the process long enough, and it will start working for you.
Who you are is what you do repeatedly. Every small habit is a vote for the person you’re becoming.
Motivation fades. Systems don’t. Build routines that carry you when your mood won’t. What you do when no one is watching counts.
You can’t feel thankful and envious at the same time. Focus on your lane; your timing is yours.
It’s not cars, watches, or vacation reels—it’s freedom, peace of mind, and time to choose what matters.
The more you strip away, the clearer you see what actually matters. Enough is a moving target—define it early.
Stop waiting to “find” your purpose. Move. Do things. Purpose shows up once you start creating momentum.
Don’t fix ten things when one messy root cause is the issue. Clean the system before adding complexity.
Say no when it matters. Confront the truth early. Do what’s difficult now to make life easier later.
Running fast in the wrong direction gets you lost quicker. Always know your north before you sprint.
Advice is useful, but not absolute. Useful ones are either very broad or extremely specific. Learn from others, then decide what actually fits your situation.
You can’t be in growth mode all the time. There’s a season to push, a season to rest, and a season to rebuild.
You’re not being lazy when you rest—you’re recharging. Even machines need downtime. You need plateaus to grow.
Track what matters, even loosely. Awareness alone changes behavior.
Being busy isn’t the same as being efficient. And being efficient is different from being effective. Ask: Is this moving the needle, or just keeping me occupied?
When your work matches your values, you stop fighting yourself. And when it hits the sweet spot between challenges and skills, flow comes naturally.
Your best ideas show up when your brain finally gets quiet. Don’t rush to fill every empty moment.
Experience doesn’t teach—reflection does. Take time to pause and extract the lesson.
The moment you think you know everything, you stop growing. Stay curious, stay humble, stay alive.
You’re supposed to suck in the beginning. Awkwardness is a sign you’re stretching your limits.
Willpower is weak compared to design. Design your environment. Develop your defaults. Make good choices easy and bad ones hard.
You can’t fake self-belief forever. Stack small wins until your brain has proof you can do hard things.
You only have so much time and energy—use tools, people, and systems that extend both. Learn to build engines that keep running even when you’re not pushing.
Plans and models help—but life doesn’t follow blueprints. Stay flexible and adjust when reality changes.
Mastery starts with obedience and ends with originality. It's called Geidō. You earn the right to break rules by first understanding them.
How you start your day shapes how you think. Don’t let noise hijack your focus before you even begin.
Preparation makes you ready, but luck makes you visible. Keep showing up—you never know which day will click.
Don’t just accept what happens—use it. Every event can be fuel if you choose to turn it into growth.

Dean (it's me!) writes about productivity, psychology, and money on this blog. Professionally, he consults SaaS and ecommerce startups on growth. He also run a DTC ecommerce brand in the SEA region. Learn more

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