When I see my direction of motivation towards working or relationships or for that matter even meditation is the want to feel proud of myself. Why do we need to feel proud of ourselves? Can we overcome that need?
Also want to know if this is related to emotional insecurity
The motivation behind the need to feel proud of yourself has it's roots in a lack of self-worth and confidence.
Lack of self-confidence can be made up of several different aspects like: guilt, anger turned inward, unrealistic expectations of perfection, false sense of humility, fear of change or making mistakes, depression etc. Depression can actually also be a result of a lack of self-confidence. '
The damage can actually be found in your ego. The ego is an identity fabricated in the mind by past events. For example your birth name, skin color, nationality, sex, or anything that deals with past experiences which reaffirms the identity of who you are. In Buddhism, there are terms such as "antidotes" which are used to cure delusions associated with general or specific sufferings. For example, anger can be cured with patience and love. Anxiety can be cured with acceptance and wisdom. Self-worth can be cured by loving-kindness and wisdom.
Loving-kindness, also known as Metta, is a practice to accept and love others and ourselves unconditionally. Typically Metta is practiced through a meditation which usually uses a mantra such as,
May you be happy. May you be well. May you be safe. May you be peaceful and at ease.
Other methods may include visualizations such as a radiating red or white auras from the heart symbolizing love. Meditation is important but more importantly is service. It takes the attention off yourself and puts it onto others. This is the quickest way for developing Metta in yourself while putting it into practice.
Next, you need to develop wisdom. Studying sutras, listening to Dharma talks, and reading books on the subject is a fantastic way to gain knowledge. Knowledge will help you systematically but it won't necessarily develop wisdom. By doing meditations such as "Zazen", you will gradually see through the ego the same way you would see through a desert mirage. Eventually by seeing through the ego it will wither away completely leaving you at peace.
Being proud is a natural consequence of certain thought patterns rooted in craving, i.e., when there is craving there is self conceiving in some cases and some cases when there is self conceiving can lead to being proud. [Tanhā Jālinī Sutta, (Vicarita) Tanha Sutta]
To overcome feeling proud you should be aware when you evaluate yourself higher and be equanimous in face of pleasant sensation that follow. To develop wisdom you have to be aware of the arising and passing nature or impermanent nature of what is experienced. To fully eradicate the roots so this does not arise again, you should know the whole sphere of sensation or phenomenas which you can sense and your perceiving the experience and positive, negative or neutral and the pleasant, unpleasant and neutral sensations that follow. [Pahāna Sutta, Avijja Pahana Sutta 2]
The practical aspects is better learned by doing a formal course. You can search for a suitable course location at: https://www.dhamma.org/en/index, http://www.internationalmeditationcentre.org/global/index.html
I think it is pretty good explained here
If one regards himself superior or equal or inferior by reason of the body that is impermanent, painful and subject to change, what else is it than not seeing reality? Or if one regards himself superior or equal or inferior by reason of feelings, perceptions, volitions or consciousness, what else is it than not seeing reality? If one does not regard himself superior or equal or inferior by reason of the body, the feelings, perceptions, volitions or consciousness what else is it than seeing reality? - SN 22.49
