What I Learned From My Twenties
As I turn thirty, I reflect on the lessons and insights gained during my twenties—a decade of rapid development, experimentation, and self-discovery.
I turn thirty tomorrow. As yet another decade rolls to an end, I find myself looking back and wondering: what lessons has it taught? For me, this is a question worthy of pause and reflection. What follows is my attempt at articulating insights I have at thirty that I didn't have at twenty.
1. Learning the Fundamentals
According to The Defining Decade, our twenties hold the potential for rapid development. This is one of two developmental phases everyone goes through (the other is during infancy). Now is the time to start learning about the world, not by twiddling about with hallucinated hypotheses, but rather by interacting with the world directly to get some valuable feedback. Maybe this means taking more risks, as we gradually let go of inhibitions learned previously. The more feedback we get, the better we can model how the world works. Gradually, reckless risk-taking becomes calculated risk-taking.
Certain fundamentals deserve our attention early, because the sooner we tend to them the more intelligently we can use the limited resource of time. For example:
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Learning about the underpinnings of wealth-creation can help us jump earlier onto the compound interest bandwagon.
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Expanding our inter-personal and intra-personal intelligences can help us create and sustain healthier long-term relationships.
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Maintaining our bodies is a habit best developed early. In my twenties I thought I could justify a decade of indulgence because my body did not complain at the time—but it doesn't work like that. The debts pile up and compound too. The last thing anyone wants is to reach the gates of their thirties only to be greeted by an insurmountable pile of health debt.
2. Learning by way of experimentation
Once I dove into curiosity-driven inquiry, I inadvertently began to level-up:
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I took improv and standup comedy lessons (I even ended up doing a comedy set) which made me realize I actually like being around people.
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I set forth into the vast, intimidating world of dating, persevered, and eventually met my partner of five years.
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I attempted a startup making wearable devices to track form during workouts - and left a year and a half later once I realized I was missing important industry experience.
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I chose to—consciously—bungee jump off a 200ft high cliff over a spring lagoon, falling for about eight seconds, three of which were in free fall. Doing so brought me confidence that I can let go when I need to.
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I made it through a ten-day silent meditation course, and walked out with extraordinary tools to explore my awareness.
Even the range of music I listen to expanded. I'm not phenomenal at any of these endeavours, but I know enough to not be in unconscious ignorance.
3. Forging alliances with the right therapist
It's possible to make it on our own, but working alongside others has the advantage that we grow quicker. People who are close to us in some ways reflect us to ourselves; the way they react to us (and why) carries information about our behaviour.
Now take this information, put it on steroids, and now we have what a good therapist can do for us. Not only does such an individual understand better than most people how the human mind works, but thanks to interactions with dozens of personalities across a large segment of the population, they also have reams of case studies pertaining to life choices and how they played out.
I've had profound realizations after hearing my therapist rephrase the language I use to present problems, and juxtapose them with how others solved it. It takes some trial and error to find the right therapist, but it's worth the find. I don't go to a therapist because I feel there's something wrong with my mind; I go so I can learn how it works.
4. Reframing the past
The more we observe our actions and the more actions that we observe, the more we start becoming aware of the causality in our lives. In my adolescence I had difficulty opening up because I was bullied as a child; when no one came to help, I attributed this to a lack of self worth. As a teenager I was overweight, which had social consequences. My parents were obsessed with my grades—so much so that I feared not being top of the class.
My twenties brought a more mature lens on the basis of which I could begin to reframe my past. If I hadn't been bullied, I wouldn't have known what an abuse of power feels like. Being overweight inspired me to learn the fundamentals of movement, prompting me to invest in a professional trainer. And my parents' persistence with my grades paved my way into one of the finest engineering schools in North America.
In our twenties we start to identify the sources of our habit patterns. Gradually, we delineate our voice amidst the din of a million other voices. We begin to understand that personality can be designed—so we need not remain stuck in the habit patterns of the past. This is liberating to discover.
5. Cultivating a support network
At twenty, I was determined to get by on my own. I would keep to myself and rarely open up. Had you met me then, you would've noticed the heavily furrowed eyebrows and the missing grin. It wasn't until I risked vulnerability and ventured into the unknown that I was acquainted with 'my tribe'. When the going gets tough, and that weight in my stomach just won't go, it helps to know I'm not in this alone. A support system is just that: a system that supports you when you need it - and laying the groundwork for this requires a considerable up-front investment.
The challenge is that support systems are bidirectional. If I want someone to be there for me during tough times, I have to be there for them when they're having tough times. This can be taxing, especially if we're not in a good place ourselves. But it's worth the investment; having a robust support system is like having a safety net.
6. Becoming comfortable with discomfort
I've learned that growth and comfort are mutually exclusive. The activities that have contributed most to my development have been uncomfortable. Standing up on stage to do standup comedy. Sitting in silence for ten days straight. Starting a business. Moving to a new country. Asking someone out on a date.
The pattern is consistent: the more uncomfortable something feels, the more it's likely to contribute to my growth. This doesn't mean I should seek discomfort for its own sake, but rather that I should be willing to step outside my comfort zone when I sense an opportunity for growth.
What's interesting is that things that once felt impossibly uncomfortable become routine with practice. The discomfort doesn't disappear entirely, but my tolerance for it increases. This gives me confidence that I can handle whatever life throws at me.
7. The importance of systems over goals
Goals are important for setting direction, but systems are what get you there. I used to be very goal-oriented: I want to lose X pounds, make Y dollars, achieve Z by this date. But I've learned that focusing on systems—the daily habits and processes—is more effective than focusing on outcomes.
Instead of "I want to lose 20 pounds," it's "I will go to the gym three times a week." Instead of "I want to write a book," it's "I will write 500 words every morning." The goals provide direction, but the systems provide progress.
This shift in thinking has made me more process-oriented and less attached to specific outcomes. Paradoxically, this has made me more successful at achieving the outcomes I want.
These lessons didn't come all at once, and I certainly didn't learn them without making plenty of mistakes along the way. But that's the beauty of the twenties—it's a decade for experimentation, for taking risks, for figuring out who you are and who you want to become.
As I enter my thirties, I'm grateful for the lessons my twenties taught me. They've given me a foundation to build upon and the confidence to continue growing and exploring in the decade ahead.