32 Lessons Learnt in 32 Years of Not Having It All Figured Out

I used to think wisdom looked like certainty. Now I think it looks like hesitation, a pause before speaking, and the quiet knowing that there’s more to learn.

These are the lessons learnt not from books or TED talks, but from living – often the hard way.

Most didn’t arrive wrapped in clarity. They came slowly, through grey areas, quiet breakdowns, unexpected detours.

Some I’m still learning. Some I’ve tried to forget.

But all of them, in one way or another, shaped me.

Self-Growth & Mindset

1. Simple living is freedom, not lack.
The less you need, the freer you become. Freedom isn’t about having more – it’s about needing less.

2. You don’t need to “find yourself.”
You’re not a hidden treasure waiting to be discovered. You’re changing all the time. You just need to notice who you’re becoming.

3. Discipline matters more than motivation.
Motivation fades. It’s unreliable. But small, consistent steps? They build things. They carry you when the spark isn’t there.

4. Don’t wait to feel ready.
The most important things I’ve done, I started without confidence. Show up anyway. Let growth catch up with you.

5. Not everything needs a reaction.
Silence can be power. Not everyone deserves your energy, and not every comment needs an answer.

6. Learn to sit with discomfort.
Running from it just brings it back louder. Sit with it. Listen. Let it pass through without breaking you.

Money & Career

7. Financial freedom matters more than a high income.
You can earn well and still be trapped. Or you can earn simply and live on your terms. It’s not about the number – it’s about control.

8. Being broke isn’t shameful.
I was earning well, but gave most of my salary to help pay off family debts. When I suddenly lost my job, I had no savings. That’s when the shame creeps in – not because you're lazy, but because survival becomes a negotiation. We only realised how deep we were in when everyone was jobless, and depression hit us all at once. Had we faced the numbers earlier, we might’ve spared ourselves the long fall.

9. You can take a detour and still be on your path.
Careers aren’t straight lines. The detours – even the messy ones – often give you the skills you actually need.

10. Not every side hustle will save you.
But each one teaches you something. What you don’t want. What drains you. What you keep coming back to.

11. Working for your dream feels different.
It’s exhausting, yes. But even in the mess, there’s something grounding about building something that’s yours.

Relationships & Boundaries

12. Not all relationships are meant to last.
I’ve made fast, deep friendships in strange places – university, onboard – and watched them fade quietly with time and distance. That doesn’t mean they didn’t matter.

13. Friendship is about energy, not history.
It doesn’t matter how long you’ve known someone. If it drains you, it’s not working. If it uplifts you, it’s worth protecting.

14. Some people only appear when they need something.
It’s okay to step back. You don’t have to keep offering parts of yourself to people who treat you like a resource.

15. Family can love you and still hurt you.
You can hold both truths at once. Love doesn’t cancel out harm. And harm doesn’t mean you owe more of yourself.

16. Solitude is not failure.
Sometimes, the most necessary chapters are the quiet ones. The ones where you rebuild alone.

Society, Pressure & Expectations

17. Comparison clouds everything.
You can’t hear your own voice if you’re always tuned into someone else’s progress. Turn down the noise. Return to your pace.

18. Social media is a highlight reel.
You’re comparing someone’s curated moment to your full, unfiltered life. That’s not a fair fight.

19. You don’t owe anyone an explanation.
Not for your job title. Not for your relationship status. Not for the way you’re choosing to live.

20. Timelines are imaginary.
They’re made up. Life doesn’t care if you’re “behind.” You’re not late. You’re just moving differently.

21. External validation doesn’t last.
Even when you get the praise, the attention, the approval – it fades. The only voice that sticks around is your own. Make it kind.

Reality Checks

22. Life is hard.
There’s no way to pretty it up. Some days you’ll question everything. Some months will feel like survival. That doesn’t mean you’re doing it wrong.

23. Plans rarely go to plan.
The job, the degree, the timeline – it all shifts. What matters is not how close you stick to the plan, but how well you adapt when it falls apart.

24. Hustling without purpose is a fast track to burnout.
I used to pull extra hours during port days – no overtime, no recognition, just this invisible hope that working harder meant being seen. But burnout doesn’t arrive with warning signs. It’s just you, months later, exhausted and wondering why you can’t feel joy.

25. There’s often a silver lining – but not always right away.
Some things make sense later. Some never do. Let that be okay too.

Travel & Exposure

26. Travel when you can.
I only travelled when friends invited me. I always thought there’d be more chances. But when itineraries vanished, ship shifts changed, and borders closed, I realised how rare and fragile those windows actually were.

27. Seeing how others live is humbling.
Comfort can make you forget what’s essential. Exposure recalibrates you.

28. You don’t need luxury to feel alive.
A quiet walk in a new place, a conversation with a stranger, a sunrise. That’s enough.

Inner Peace & Balance

29. A peaceful life might look boring.
To others, it might seem uneventful, small. But peace is underrated. And it’s worth protecting.

30. Rest isn’t a reward.
You don’t need to earn it. You just need it. Don’t wait for permission.

Letting Go & Moving Forward

31. You’re allowed to change your mind.
About who you are, what you want, what you believe. Staying the same isn’t strength – it’s stagnation.

32. Nothing is permanent.
Not your struggles. Not your identity. Not the version of you who started reading this list.


 

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Joanne Tai

An adventurer, and former seafarer.

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