There are some people in the world who support you and there are others who want to hold you back. I believe I am in the former group, but there are some people I know who are in the latter.
When dating someone who feels less successful than you, I feel like no matter how much I want to achieve, I hold back. I don't want to be too successful in anything because it creates friction. I work hard and reap the rewards. I don't mind if another reaps the rewards, too (whether, or not, they work). And if you can't share with the ones you love, then what's the point?
Of course, I'm happy when the other person does something that makes him/her happy (this didn’t include sitting around and drinking with “friends”). And, I support the other person and push him/her towards being a better person with some contacts or tips; it's beneficial for them.
Sadly, the outcome wasn’t always positive. This is especially true when you’re with someone who is very insecure and doesn’t want to have others around who are more successful than they are. It’s a constant reminder of how insignificant and inconsequential they feel and are.
Whatever the reason are for being this way (a coddling upbringing and “friends” who are just as delusional) are beside the point.
After the dissolution of this kind of relationship, I came to a conclusion: I could either continue on my life path, or do something different. For once, I took the road less travelled and I created something I’ve wanted and never had before. It took a lot more work than I expected, but at least I can say I accomplished something. I didn’t expect anything to be handed to me.
Now, I have my own business. And, I did this without having someone hold me back because of their insecurities. The only thing I need now is to have someone who will support me and push me to go to the next level.