15 Best Ways to Wreck Your Twenties (and beyond!)


Why not ruin your twenties?

Want to wreck your twenties and way beyond? Here are the 15 best ways to do it.

1. Let fear win. Always. Follow it wherever it stops you. Never do anything you’re scared of. If it’s a reach, if there’s a chance it might not work, why do it? You might fail. Better to never know and always wonder, right?

2. Compare, compare, compare. You can never compare enough, especially on social media. Scroll, and scroll, and scroll. Let everyone’s success smother you like an electric blanket turned up on high in August. Obsessive Comparison Disorder doesn’t work in moderation.

3. Stay in that exact place where you know how to handle everything. Sure you might be miserable, but at least you’re comfortable in it.

4. Be the best critic and cynic you can be. Be like the cafeteria leader in high school, mocking anyone and anybody who is trying something. Be the wrecking ball to everyone’s first building blocks. Crush them before they can create. That way you can feel better about everything you’re not creating.

5. Don’t tell anyone where you’re going. Don’t ask for help. Do it all by yourself. As I write in 101 Questions You Need to Asking in Your Twenties, we have to stop struggling to make it appear like you’re not struggling. Life is a heavy load sometimes. We all need people there right next to us, helping us from getting crushed.

6. Buy, spend, and pay for things you can’t pay for. Because why wait, right?

7. Burn bridges like you’re behind enemy lines in WWII. Burn all the bridges so there’s no chance of escape when you get in a tight pinch. You don’t like something or someone, yell it at extreme octaves across social media. Throw shade. Throw gasoline. Light the match. Repeat.

8. Stop reading good books. Just read the daily glut of infotainment headlines about everything going wrong. Stop learning real stuff. Everything you need to know about life you’ve surely learned by 21-years-old.

9. Follow all the trends. Chase after them like a two-year-old sprinting after bubbles. Sure, they’re all going to pop sometime soon, but why not skin your knees a thousand times falling after them.

10. Don’t ask yourself any hard questions. Just put your head down and keep going in the direction you don’t want to go. When you retire in your 70s or 80s, I guess then you can ask yourself what you want to do with your life. Go through transitions and crisis as fast as possible so that you don’t have to think about where they are taking you.

11. Be wildly erratic and amazingly arrogant.

“Success in your 20s and 30s is about consistency, humility, and many other unsexy words that won’t make the Twentysomething Hallmark Collection.” – 101 Questions You Need to Ask in Your Twenties

Don’t commit and work through the struggle. Just bounce from one thing to another like a rubber ball on a slab of cement.


12. Get yours. Always get yours. Don’t worry about theirs. Especially if you’re thinking about marriage. That relationship especially better serve you and your desires 110%, right?

13. Fail, then keep calling yourself a failure.

14. Never give yourself any time or space to think. Whenever silence creeps into your day, fill it as fast as possible with your phone. Don’t avoid distractions. Live for them.

15. Keep thinking that at 29-years-old, you’ll have it all figured out. Or at 35-years-old. Or 65-years-old. We’re never supposed to have it all figured out. And the people who think they do, are in for the biggest surprise of them all.

1 Comment

  1. Just another twentysomething

    I didn’t even know I needed this but I did. I’ve been consuming your books, blogs and work like caffeine. Thank you so much for doing what you’re doing because you did succeed to guide someone through their worst.

    Just another content admirer across unimaginable latitudes and longitudes.


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