20 Life Lessons I Wish I’d Learned In My Twenties

If only we could go back in a time machine with the knowledge we have now

life lessons for younger self

Youth is wasted on the young: George Bernard Shaw sure got that right.

If only you could go back and tell your 20-something self all those life gems you’ve gathered along the confusing road to this point.

Assuming I’d even listen – and that’s a mighty big assumption when you’re that age – here’s what I’d say.

1. Stop worrying about what other people think. They’re fumbling around just as much as you are, and no one is getting out alive.

2. Be prepared to fail, but don’t be too scared to try. You can always dust yourself off and try something new. People respect you more if you at least try – and you’ll respect yourself more too.

3. Stop being so serious and careful. That doesn’t mean you walk around looking for trouble, just let your guard down from time-to-time. People are fundamentally good, most of the time.

4. Be kind to others. You really do get back what you put out.

5. Floss – a lot. It’s less stressful visiting the dentist for a $200 six-month clean than forking out $7000 for two crowns and a bridge.

6. Don’t chase someone you like. I know it’s confusing when you hear stories about someone saying ‘oh, he/she wore me down’. But that’s probably not true. If they like you, it’ll never be too hard. If they don’t, there are others out there who will love you more.

7. People like confidence, in business or personal life. If it doesn’t come naturally, fake it until you make it.

8. Travel more. It will open your mind, and your heart.

9. Be less selfish. Do something every year for someone you don’t know, without ever  expecting anything back.

10. Get a rescue dog. Even if you don’t want kids, you need to feel what unconditional love feels like.

11. Wear sunscreen every day and moisturise. The sun will kill you if you abuse it, or at the very least age you way beyond your years.

12. Look after your health. Not in a must-quit-sugar-and-get-a-gym-membership way, but find a physical activity you love and be aware of what you put in your mouth.

13. Question everything. From the food you’re eating, to why you have to go on holiday with everyone else at the same time every year.

14. Tell your family that you love them. They won’t be here forever, and you’ll wish you had.

15. Don’t take on other’s negative energy – it wastes too much time and won’t get you anywhere. Someone cuts you off in traffic, let it go. Yelling and retaliating won’t change their behaviour, but the stress will shave minutes off your life.

16. Do it now; everything now. Don’t wait until tomorrow. You may think you have all the time in the world, but it DOESN’T last. Believe me now when I say a year in your 20s will feel like a week in your 50s.

17. That doesn’t mean you’re a doormat. Stand up to bullies, but pick your fights and know when to walk away.

18. Never go into credit card debt. Sure, have nice stuff, or a special outfit, if that’s your thing, but put most of your energy into fostering friendships and/or helping others.

19. Jealously is futile. Accept that others will do better than you, whether you like them or not.

20. Be smart with your money. It’ll make life so much easier when you’re made redundant, want to change career direction, or make that seachange.

What are your life lessons you’d impart on your 20-something self?


From sport, business, to general news and lifestyle, the co-founder of 50 So What has covered it all in more than 25 years in print, TV and digital media. When he's not working on the site, you can usually find him on a golf course, playing tennis, or on a flight across the ditch to catch-up with family and friends in his native New Zealand.


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