Hi inspirationneeded,

While you continue your conversation on this thread, you may want to give a try at Bach flower remedies for things you described below.

“I’ve always found it hard to open up to people, probably originating from my childhood and having to “hide” the real me and fearing criticism or judgement.”

“But the darkness of depression, lack of self esteem, lack of confidence and loneliness still hangs on.”
“Any alternative strategies?”

From your post it looks like you are ‘Agrimony’ and ‘Larch’ type of personalities. Nothing wrong in you but they are just referred as personality types.
Agrimony
Helps you communicate your true feelings rather than hide them behind a cheerful face

Larch
Instills a greater sense of self-esteem when you feel inferior, fear failure or lack confidence

If any of these ring any bells and relate to you then you may want to identify more from the below link as only you are the best judge of yourself.

http://www.bachflower.com/bach-flower-remedy-questionnaire/

Once you have identified your personality type write them down, and then I strongly recommend you to go to their detailed descriptions in the below links, especially Agrimony and Larch (or any additional ones that you may have identified)
Agrimony
http://www.bachflower.org/agrimony.htm
http://mudraguide.com/bach-flower-remedies-agrimony-a-smile-plastered.html

Larch
http://www.bachflower.org/larch.htm
http://mudraguide.com/bach-flower-remedies-larch-and-an-inferiority-complex.html

Of course you are going to find out more but as a side note, if you are feeling shy and timid then you may also want to check the two detailed description links mentioned above for Mimulus as well (Brings courage and calm to face things that frighten or worry you, also aids the shy and timid, scared to speak in public)

Surely 100% of what is written on any particular personality type may not match with you but you can pick the closest possible.

Please take the time and patience to fully read the above links/pages. Don’t make any decision on them yet and if you are keen on those then please feel free to write back with your findings if you think they relate to you. In the mean time you can also find out more about ‘Bach flower remedies’ on the web to see if they suit your interests.

Regards,
VJ