At 50, I’ve been reflecting a lot on my life. Looking back at my 20-year-old and 30-year-old selves, I see so many moments where I could’ve made better choices. If I could go back, I’d share these 40 lessons—hard-earned truths and simple mindset shifts that would’ve changed everything. Here they are, with stories and examples to bring them to life.
1. Read the Right Books
I used to read books like How to Be the Best Employee—all about working harder and impressing my boss. But I ignored books that could’ve taught me about life, like Man’s Search for Meaning by Viktor Frankl, which showed me how to find purpose even in tough times. Read books that challenge your thinking, not just ones that make you a better worker. For example, reading The Alchemist at 20 could’ve inspired me to follow my dreams sooner instead of chasing a paycheck.
2. Think Long-Term
When I was 25, I took a job because it paid well—$500 more a month! But it was a dead-end role, and I stayed for five years, miserable. If I’d thought, Where do I want to be in 10 years?, I’d have chosen a job that built skills for my future, like learning to code or starting a side hustle. Always ask: Does this decision help my future self?
3. Confidence is Everything
At 28, I wanted to start a small photography business, but I thought I was not good enough. I let fear stop me. Years later, at 40, I finally did it—and it worked! Every success I’ve had came when I believed in myself, even when the odds were against me. Confidence isn’t about being perfect; it’s about believing you can figure it out.
4. Design Your Ideal Life First, Then Make Money From It
I used to think, I’ll make money first, then live the life I want. But that “someday” never came. At 38, I flipped it: I wanted freedom, so I started a freelance writing career. Now I work from a beach in Bali some days! Ask yourself: What life do I want? Then find a way to earn from it—even if it’s small at first.
5. Be Braver
At 22, I was fearless—I’d travel solo with $50 in my pocket. But by 30, I was scared of everything: quitting a bad job, asking for a raise, even talking to new people. My biggest regrets? Not the risks I took, but the ones I didn’t. Be brave. The worst that can happen is you learn something.
6. Friends Come and Go—And That’s Okay
I used to feel guilty when friendships faded. At 27, I clung to a toxic friend because we’d known each other since high school. But he drained my energy. Letting go was hard, but it freed me to focus on friends who truly mattered—like my buddy Sam, who’s been there through everything. It’s okay to let go of people who don’t fit your life anymore.
7. Understand Your Childhood to Understand Yourself
I grew up with a dad who was always working, so I thought success meant being busy 24/7. At 35, I realized that’s why I overworked myself to burnout. Once I understood that, I could change—I started saying no to extra projects and made time for myself. Look at your childhood without judgment. It’ll show you why you are the way you are.
8. Stop Living for Others’ Approval
For years, I chased promotions because I wanted my parents to say, We’re proud of you. But I was miserable in those roles. At 40, I started living for me—I moved to a small town, started gardening, and wrote a blog about it. Who are you when no one’s watching? That’s who you should be.
9. Cut Out Useless Socializing
At 29, I went to every networking event, collecting business cards like trophies. But I had no real connections. One day, I met a guy who ran a startup. Instead of just handing him my card, I offered to help with a project for free. That turned into a real partnership. Focus on being valuable, not just knowing “important” people.
10. Work Should Serve You, Not the Other Way Around
I took jobs for money—like a sales role I hated at 26. I learned nothing useful and quit after two years. Instead, I should’ve picked jobs that taught me skills, like marketing or design, that I could use later. Choose work that builds your future, not just your bank account.
11. Time is More Valuable Than You Think
At 30, I thought I had forever. Then my cousin passed away suddenly at 32. It hit me hard—life is unpredictable. Don’t waste years on things that don’t matter, like scrolling social media for hours or staying in a job you hate.
12. You’re in Charge of Your Life—No One Else
I used to wait for someone to “fix” my life—my boss to give me a raise, my partner to make me happy. But at 39, I realized: I have to make it happen. I ended a bad relationship, started therapy, and built a life I love. Want something better? Go get it.
13. Know Yourself Deeply
At 33, I was always angry but didn’t know why. I started journaling and realized I was avoiding my dream of being a writer because I feared failure. Once I saw that, I could face it. Step outside your mind—ask, What do I really want? What am I scared of?
14. Start Before You Feel Ready
I waited until 41 to start my podcast because I wanted the “perfect” equipment. But when I finally started, with just my phone, it grew to 10,000 listeners in a year! The perfect moment doesn’t exist. Start now, even if you’re not ready.
15. Have a Clear Goal
At 25, I drifted—no plan, no direction. I’d work random jobs, spend my money, and wonder why I wasn’t getting anywhere. At 38, I set a goal: Own my own business in five years. I wrote it down, made a plan, and hit that goal. Write your goal. Say it out loud. Make it real.
16. Find Your “Why”
For years, I just existed—work, eat, sleep, repeat. At 37, I asked myself, What makes me feel alive? The answer was travel. So I saved up, quit my job, and backpacked through Europe. Find your “why”—it’s what makes life worth living.
17. Stop Living for Others’ Expectations
My parents wanted me to be a lawyer, so I studied law at 22. I hated it and dropped out after a year. Now I’m a freelance designer, and I’ve never been happier. Don’t let others’ opinions control your life. It’s yours to live.
18. You Can’t Change People—Choose Wisely
At 29, I dated someone who partied too much. I thought I could “fix” her. Three years later, I was exhausted, and we broke up. People don’t change unless they want to. Pick the right people—friends, partners, coworkers—from the start.
19. Give Yourself Time to Think
I used to be so busy I never stopped to think. At 36, I started taking walks with no phone—just me and my thoughts. That’s when I got the idea to start my own business. Schedule quiet time. Your best ideas come when you’re still.
20. Find Mentors
At 31, I wanted to learn photography but struggled alone for years. At 39, I met a pro photographer who taught me in six months what took me years to figure out. Find someone who’s done what you want to do—they’ll save you time.
21. Learn Money’s Three Rules
- Make it: At 28, I learned graphic design—a real skill that got me freelance gigs.
- Keep it: I stopped buying dumb stuff like $200 sneakers I didn’t need.
- Spend it wisely: I used my money to travel instead of buying a fancy car. Money is freedom—use it to build the life you want.
22. Spot Fake News
At 35, I believed a viral post about a “miracle” investment. I lost $2,000. Now I double-check everything, especially online. In the AI era, misinformation is everywhere. Question what you read.
23. It’s Never Too Late
At 40, I moved to Spain and started over. I learned the language, made new friends, and built a business. Age is just a number. You can always start fresh.
24. Location Changes Everything
At 32, I lived in a small town with no opportunities. I felt stuck. At 38, I moved to a big city, and suddenly I had clients, friends, and ideas. Where you live matters. If you’re not growing, consider a change.
25. Dress Like the Person You Want to Be
At 27, I dressed like a slob and wondered why no one took me seriously. At 35, I started wearing sharp clothes, and people treated me differently—better jobs, more respect. People judge fast. Look the part.
26. Decide Fast, Act Faster
At 30, I overthought starting a blog for a year. By the time I did, someone else had already taken my idea and built an audience. Don’t overthink. Done is better than perfect.
27. Stop Obsessing Over Politics and News
I used to watch the news every day, stressing about things I couldn’t control. At 39, I stopped. I focused on my life—my health, my work, my family. Most news doesn’t affect you. Focus on what you do.
28. Protect Your Mental Health
At 34, I burned out—couldn’t sleep, always anxious. I started therapy and went for walks in nature. It saved me. Don’t let stress steal your life. Find what brings you peace.
29. Your Life is #1
At 31, I worked 80-hour weeks for a promotion. I got it—but I also got sick and missed my sister’s wedding. No job is worth your health. Put yourself first.
30. Work Backwards
At 37, I wanted to be a writer. I worked backward: Step 1: Publish a book. Step 2: Write every day. Step 3: Take a writing course. It gave me a clear path. Start with your goal, then plan the steps.
31. Never Depend on Others for Success
At 29, I waited for my boss to promote me. He didn’t. At 36, I started my own business and never looked back. Don’t wait for someone else to give you what you want. Create your own luck.
32. Stay Present
I used to dwell on past mistakes or worry about the future. A quote from Zeng Guofan changed me: “What’s done is done. The future isn’t here yet. Focus on now.” When I started living in the moment, I found peace.
33. Embrace AI Now
At 40, I started using AI tools for my business—writing, designing, even brainstorming. It’s like the internet in the ‘90s: if you ignore it, you’ll fall behind. Learn AI now—it’ll make your life easier.
34. Research Big Decisions
At 26, I bought a car without researching, and overpaid by $3,000. Now I research everything: jobs, investments, even vacations. Don’t rush. Ask questions, study, then act.
35. Understand Human Nature
People act from self-interest, love, or fear. At 32, my boss promised me a raise but never gave it—he feared losing his budget. Once I saw that, I stopped taking it personally and found a better job. Understanding people makes life simpler.
36. Learn the Industry Before the Skill
At 33, I wanted to open a café because I loved coffee. But I didn’t study the business—permits, costs, competition. I failed in a year. Learn the industry first, then the skill.
Final Thoughts
If I could tell my younger self one thing, it’d be: You have more power than you think. Stop waiting. Start now. These lessons aren’t just for me—they’re for anyone who wants to live better. Which ones resonate with you? What would you tell your younger self?