25. The tattoos you didn’t get

– “I wish I’d paid good money for a poorly drawn cartoon of a fish which is native to a place I’ve never been to.” – No one, circa never.

24. Betting on yourself

– Your friends and colleagues want you to do well but never better than them. At the end of the day, it’s up to you to back your own ideas and dreams regardless of whether others are going to support you.

23. Quitting a job you hate

– There’s nothing more precious than time. More than three-quarters of your waking life can be spent at work and if you hate your job you probably spend the other quarter whining about it. If you can’t see yourself saying, “I miss working at X.Y.Z.” then Q.U.I.T.

22. Taking the leap and introducing yourself

– Worst case scenario you’ll be turned down, laughed at or ignored. Best case scenario…

21. Sharing what you’ve earned

– Remember that one time someone gave you valuable advice, made an introduction for you or lent you a dollar just to see you get up on your feet? The feeling they had when it paid off for you was invaluable. And you’ll never understand that feeling unless you try it yourself.

20. Walking away from social media

– As permanent as facebook appears today, and as rewarding as it feels to have your colleague’s friend’s babysitter double-tap your photo of home-made guacamole, there are always at least 3 infinitely better ways to spend your time.

19. Staying true to your values despite short-term appeal

– Don’t let someone talk you into “just one drink” when you’d planned to work out; and it’s just as important to ignore that “you up?” text from an old flame just because there’s nothing official with the girl you’re seeing.

18. Sitting in the shade

– Although your eyes will eventually deteriorate to a point where you can’t recognise your own feet, that’ll only happen well after your sun spots and wrinkles get big enough to see from a mirror at 20 paces. There is no sign of ageing that you’ll ever attribute to the sun exposure you didn’t get.

17. Questioning the validity of outdated rules

– One piece of advice worth taking with you, if no other: “Rules made by wise men should be broken by wise men”.

16. Complimenting your mother

– She’s the most important woman in your life for the majority of your life and she probably gets treated to the least amount of compliments. Besides, you probably have a testosterone-fuelled puberty to repent for.

15. Picking up a book

– Especially if it’s of the Orange and Creme (Penguin Books) variety.

14. Getting lost

– Being comfortable is a double-edged sword, slicing through both pain and progress. No matter how fond you are of watching those late night talk shows for their NYC appeal, you’ll never learn about the world while you’re stuck in the town you grew up in.

13. Making your own luck

– Sure, a local won the lottery and that could have been you. But if every other punter spent that dime on something else, there’s a statistically infinite chance that they’d be spending it on something more valuable.

12. Having an early night and an early morning plan

– You’ll thank us when you wake up tomorrow.

11. Listening to your grandparents

– If you could buy 70 years of wisdom for $3.50, would you? Then call one of your ancestors and draw out a story through a cup of coffee.

10. Ditching the liability for an asset

– Is a month’s saved salary the only thing standing between you and a smart investment in property, business, relocating or educating yourself? Sell something that’s depreciating (e.g. your car, furniture, watch, computer or smartphone) and you’ll be making a two-fold improvement to your life.

9. Buying a decent pair of shoes

– A single $600 pair of shoes is worth twenty $100 pairs.

8. Owning a tailored suit before you turn 30

– And make sure you stay that size the rest of your life.

7. Whittling your own yardstick

– There is always another level to everything and everyone. You can’t be the best at everything everyday but you can be better at one thing today than you were yesterday.

6. Always carrying a twenty

– Keep it folded in your front pocket and make sure you’re the first to tip, pay for coffee or appease a knife-happy mugger.

5. Buying a bottle of scotch the day your son is born

– And quietly look after that monument until he turns 18, moves out at 21, graduates from college, gets married or has a son of his own. Whilst the maturation process may have ended the day it was bottled, nothing tastes better than decades of delayed gratification shared with your prodigy.

4. Making a routine

– Work out a few things that make you either happier, healthier or wiser and pencil them in either every day, week or month.

3. Breaking a routine

– Morning coffees, nightly Netflix, weekly drinks with the lads. Sometimes it’s worth reminding yourself that: 1. some routines aren’t worth continuing; and 2. something completely new and challenging is only a decision away.

2. Get close to someone outside of your social, professional and/or cultural groups

– There is no better way to learn about the world than spending valuable time getting to know someone from another part of it.

1. Taking a breath

– Sure, running around like a bookie on race day can look productive. But slowing down, taking that breath and kicking the same goals without breaking a sweat is the mark of a true Gent & Scholar.

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25 Decisions You'll Never Regret
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