Should unreliable dreams be discouraged?

https://www.bing.com/images/create?FORM=GENILP

Impossible is word in a fool's dictionary. If my friend has their heart set on achieving something very difficult I would be the last one to ever discourage them. We learn from our mistakes.

Here's an illustration:
Henry was determined to become a millionaire before he turned twenty-one. He came from a high school educated middle class family with no special social, political or economic connections. Just salaried workers. Both parent worked.

But Henry was determined. While still in secondary school as soon as he got his driver's license he convinced his father to buy him a pick up truck. Henry started a landscaping business. Hired his high school buddies and was getting contracts from apartment complexes.

The money was rolling in. His grades in school were good, above average. He decided to buy a vacation resort property in the next county. He poured funds into developing it and went in over his head in debt. The property was repossessed by the bank and Henry had to declare bankruptcy. Was he unhappy about what happened? Of course. Would I have discouraged him from his efforts? Never. He learned some valuable lessons. And later became very successful in computer programming.

A while back I asked a friend what I should do? Leave my high paying job to try something completely different or stay. He said, "I'm going to tell you something my father told me, 'Whatever decision you make is the right decision because you made it.'"

link to contest: https://steemit.com/hive-150487/@boylikegirl.club/h5v6vzz6a17