Why Retiring Early (Probably) Won’t Make You Happy

Dividends Forever
2 min readAug 17, 2022

Imagine waking up early with no obligations for the day. What would you do? Hike? Paint a painting? Read a great novel? Learn to play a musical instrument?

Realistically, you’d probably end up wasting the day.

I visited my parents in Iowa this month, and one interesting thing about the state is how many locals inherit farmland and rent it out.

These properties cash flow tens of thousands of dollars in passive income each year, and a huge number of Iowans do not work because their rental checks cover all living expenses.

So what do people do instead?

Drink beer. Putter around the house. Watch Netflix.

Iron sharpens iron. Zero adversity with infinite free-time leads to nothing.

Why You Need Limitations

Remember in school when you’d have a one-week deadline to submit a project?

Most people started the assignment the night before it was due.

When you have infinite free time and no fixed schedule, all those cool things you want to do never get done.

There’s no urgency and nothing at stake.

The people I’ve met who “retire early” — in the classical sense where retirement means all your time is leisure time — do absolutely nothing of interest. They have no adversity or push-back, so they turn simple errands like a trip to the post office into all-day events.

In contrast, people who live with intention set measurable goals and issue self-imposed deadlines.

If you want to have full control over your time, you need to be disciplined.

Otherwise your newfound freedom quickly devolves into watching action movies at 9:30 on a Tuesday morning or taking three hours to go grocery shopping.

Disclaimer: This article is for entertainment purposes only. It is not financial advice, always do your own research.

Dividends Forever

Providing you with detailed insights into long-term, buy-and-hold dividend investment opportunities.