I'm 39. Here are huge red flags I wish I knew in my 20s:

96 views Sep 30, 2025 ~2 min read

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I'm 39.

Here are huge red flags I wish I knew in my 20s:

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1. Describing hard work as "hustle culture." Only losers with small goals think this. Real work doesn't feel like work.

2. Buying luxury crap to impress nobodies. Shallow people care about Lambos. Smart people just care about personal freedom.

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3. Staying stuck in perpetual poverty. You can't save your way to wealth. The answer is just to make more money by upgrading your skills. 

4. Drinking alcohol on weeknights. Kills brain cells and causes hangovers. It'll suck away all your energy. Grow up.

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5. Staying out after 10 PM. Nothing good happens then. It's just fights, drunk people, and seedy behavior. 

6. Embracing hook up culture. Getting laid with all different partners gets boring. Grow up and choose one partner. Then start a family.

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7. Publishing a book to call yourself an "author." It doesn't give you credibility. And without an existing audience nobody is buying your book. 

Most people write books for themselves, not the reader, so they make no sales.

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Basing your entire career around passive income. Real income requires active work. Passive = lazy mofo

Choosing careers with lottery-style odds of success. Musician, actor, author, painter. Grow up. Treat these as hobbies. 

Buying heaps of investment properties using debt. All it takes is one 2008-style recession & you're f*cked.

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11. Wanting to retire at 65. This is just delayed gratification in disguise. Live the good life now.

12. Thinking that being passionate is enough. It's not. You need high intensity which means you must be obsessed.

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13. Working a cubicle job. There's zero creativity or imagination. And you get told what to do. Start there, then build a one-person business. 

14. Refusing to embrace uncertainty. Growth always feels uncomfortable. If you don't choose it you end up with regrets.

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15. Staying stuck in indecision. "Ready" is not a feeling or moment in time. It's a decision. Decide. 

16. Turning everything into a joke. Humor is often a mask to avoid saying what you think. Less joking around, more saying the truth.

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Always choosing easy goals. Hard goals are where fulfillment is found.

Not having habits backed by an operating system. A goal without a system is just a p0rn fantasy

Being in love with politics. Solves nothing. Politicians take the job for the perks. And most of them take bribes in a legal way.

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Being unkind to strangers. Shows a lack of discipline and a big ego in disguise. You never know who that stranger you spoke down to is.

Living for the weekend and holidays. Happy people don't do this. They love the work they do.

Thinking AI is a trend or even a scam. It's loser mentality. AI is like the internet. It's changing everything. Embrace it.

The biggest green flag is choosing to be personally responsible for your income.

You can make as much money as you want.

Here are some options for you: timdenning.com/100k-xc/

I'm 39. Here are huge red flags I wish I knew in my 20s:

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