How to fix low self esteem?

M. asks: I like getting free stuff - how does self esteem play into it?

Who doesn't like getting free stuff? If you don't, there is something wrong with you. 

M. crafted her question very carefully. She is asking "how does self esteem play into it". Generally high self esteem is considered better than low self esteem. No one would worry about high self esteem. 

She probably just didn't want to ask directly if liking free stuff is connected to low self esteem. 

So the question actually asks: Is enjoying the "free stuff" has anything to do with low self esteem: Do I have low self esteem if I like free stuff?

I am not done yet taking apart this question. Actually mentioning of "enjoying free stuff" is a misdirection. The question itself points to a self esteem problem. The person asking this question is afraid being judged by others. People how are afraid of judgment usually have low self esteem.

Self esteem can be 

1. Low (adequate or inadequate) 

2. High (adequate or inadequate) 

The optimal is high and adequate. 

Self esteem is the price tag the person puts on him/herself. 

Just like with things, people can overprice, underprice or appropriately price themselves. 

The price tag on a person is connected to the resourcefulness. 

Someone with low self esteem can price himself either adequately (is not resourceful and has a realistic picture of it) or inadequately (has recourses but they are not considered or are discounted).

The same can happen with high self esteem. The person either prices himself correctly or is overpricing himself (has no resources but thinks of himself a lot). 

People who priced themselves incorrectly too low or too high, have a life full of emotional roller coaster. They feel that the price is not right and they constantly try to gage and adjust it by the reaction of others. If they are liked by others, the price mentally goes up until someone brings it painfully down. 

The people who are aware of their recourses and price them correctly have relatively stable mood. They are not moved much by opinions of others. 

The reasons for inadequate self-pricing can be different, from the inborn psychotype to the parental damage done wile upbringing. 

But independent from the reasons something can be done to fix it. 

One of the ways to fix low self esteem is to become a professional / an expert in some field. That will take time, but it is a sure way to get there. 

For example my geography knowledge is not good. But as my sister said once "She can afford not to know geography, she is a doctor". In that situation it was funny but the truth was there. You can hyper-compensate in one area and then you can slack in others.  

You can see many examples when people try to become experts in different areas, from law to Taro card reading. The more useful and respectful the area is the most certain is the way to the adequate increase in self esteem. 

Another way to fix the self esteem is to change the group. 

For example in schools or work places there is a certain group dynamic at play. 

Every group has a leader, several followers, the class clown. Most groups also have an opposition leader and a negotiator (who tries to keep peace between them). Most groups will have an outsider who is bullied. Sometimes there are also experts and wizards. 

The person with the lowest self esteem is the outsider. Working his way up, he can change groups and get in to the position of an expert or a wizard, dependent on his  interests and abilities. 

The expert knows something very well and is usually not bothered by the leader, especially if his knowledge is useful to the lieder.

The wizard is a variation of an expert. The wizard is an expert in weird stuff and sometimes scary stuff. He will also be left alone because weird is scary. 

When changing groups outsiders can never jump to the leader position. It is not natural for them. The easiest way to "advance" is to take a special spot of an expert or a wizard. 

For example, in school I was very shy. My grades were great, I almost never got any Bs. But my shyness made me a target of the group lieder. My self esteem was low and I was incorrectly pricing myself. To scare away the lieder and the followers who tried to bully me, I used foreign language (German) to put spells on those who bothered me. I made sure they know that I can put spells on them. I also learned card reading and palm reading and took the spot of the wizard. I was weird but useful and I was left alone and was not bullied. 

Later I thought that if I was born long time ago I would be a shaman. It later grew into the wish to become a doctor. Shamans, witches or wizards give you potions, doctors give you "potions" too - what is the difference? I am still a wizard. 

Getting back to the question: If liking free stuff and low self esteem are connected?

They are only connected on the level of fear of being judged by others. If you are afraid that others may perceive you as cheap, if their opinion bothers you, then yes, you have low self esteem. You price the opinion of others higher then your own. You are underpricing yourself and overpricing them.