Dear iamone,

I was thinking about your situation… I don’t necessarily think that you lack self-love and self-esteem, and here is why: you didn’t feel bad about yourself when the supervisor at your previous job (which you quit) told you you performed poorly.

They thought I was horrible at what I do (I think that was very harsh; it takes time to build up your confidence and become skilled at some things)

That’s a healthy self-protection instinct: you rejected their harsh evaluation and treated yourself with kindness, telling yourself that “it takes time to build up your confidence and become skilled at some thing”. That’s not how someone with low self-esteem would react. A person with low self-esteem would take other people’s criticism to heart and start berating themselves. But not you – you rather dismissed their criticism and called them losers, rather than taking any of that criticism on yourself. That’s why I believe you don’t have a real problem with self-esteem.

At the same time, you do have a problem, because you do believe you are a “loser”. The reason you believe you are a loser is not because you believe you lack skills or talent, but because you haven’t reached the success you hoped for. Be it material success, or career success or relationship success. So I would like to explore your definition of success a bit more…

This is how you defined a perfect career (a part of your description of a perfect life):

you have a job in which you are able to use your best talents and which you find interesting and rewarding both intrinsically and extrinsically (pay).

The above would mean career success for you, right? Using your best talents in a job that you find interesting and fulfilling, and which pays well too.

At the same time, this is what you said about using your talents:

I haven’t been true to who I am and the gifts I’ve been given.

I really enjoy very little. My entire life has been focused on trying to achieve things that will make others see me as respectable or acceptable.

I paint paintings, but I think I do it to be able to say – Look! I’m a successful artist! rather than because I enjoy it.

There seems to be a conflict within you: on one hand, you would like to do something you enjoy and that would give you fulfillment (and be well paid). But on the other hand, your entire life has been focused on “trying to achieve things that will make others see me as respectable or acceptable”. You haven’t spent your life trying to develop your talents, but you have spent your life (so far) trying to impress everyone. Trying to get their approval and validation.

To me it seems like you’re sitting on two chairs. One is being true to yourself and following your passion (hoping that it would result in material success too). The other is chasing the money and what you deem a “respectable” career (being a lawyer or a doctor), but disregarding your heart’s desire. You are sitting on both chairs and you sort of fell in between them. The result: you have neither fulfillment nor money/career success.

If you want a chance at a “perfect life”, as you define it, I think you’d need to choose. And I think you’d need to choose your heart’s desire (to thy own self be true), regardless of what others will say or how ridiculous that desire might seem to some of the people….