Having Entitlement Issues means we don't feel worthy or deserving of RECEIVING what we want and need~ which is a byproduct of poor self-worth. Allow me to explain . . .
You may feel okay about asserting yourself under certain circumstances, but not others. Fear of loss interferes with your ability to confront someone or assert for your needs. This issue can intrude on your interpersonal AND professional life, and keep you ensconced in a cycle of accepting neglect or abuse from others.
Entitlement issues have very deep roots that are buried in one's earliest life experiences, dating all the way back to infancy. If our mother wasn't emotionally stable/sound and equipped to love us well enough, we developed entitlement issues. If she didn't convey that we were precious and cherished by her, we grew into adults who are unsure about our true worth.
One who feels on ANY level (consciously or subconsciously) UNWORTHY of having what they need and want, has a hard time when someone takes advantage of or mistreats them. When they're forced to ASK for what they're owed by a friend, or when it seems essential to raise client fees or collect on services rendered, profound discomfort arises within.
At its core, this is reluctance to meet the needs of the self, is POOR self-worth. It's crucial to dismantle this adaptive reflex one learned in childhood, so a life far more rewarding and plentiful can be sought and embraced.
Along these same lines, people with entitlement issues have a deep-seated fear of JOY. They learned during childhood, that feelings of stability and happiness were extremely fleeting, and routinely followed by setback, disappointment or disaster.
If these individuals aren't constantly struggling to one degree or another, they become anxious. In a sense, they're always projecting ahead of themselves into the future (fast forwarding, I call it) to try and envision what terrible fate might befall them, so they can steel themselves emotionally against anticipated feelings of sadness, disappointment and devastation.
Feeling a little "too good," triggers an inner reflex that immediately alerts these folks to prepare for "the other shoe dropping." Those with with Anxiety Disorder and Panic Attacks have always had this automatic reflex at their baseline, since they were toddlers: "Always prepare for the worst~ that way, I can't be disappointed."
In childhood, this saved a lot of us from the pain of shock or surprise when something inevitably happened to foil our glee, so we incorporated it into our emotional repertoire, and have relied on it as a Survival Strategy, ever since.
The problem with this orientation though, is that what always holds true metaphysically is, "what we envision and give our attention to, we attract and manifest for ourselves."
Alas, that old saying, "Be careful what you wish for" isn't nearly as dangerous, as Be Careful What You Fear~ because sure enough, prophesy fulfillment is gonna kick in eventually, and you will have created EXACTLY what you've been expecting!
My Overcoming Anxiety course online, addresses this one particular issue (among many other anxiety triggers) in the most precise and comprehensive detail. WHY??
Because 'waiting for the other shoe to drop' anxiety is THE MOST COMMON anxiety trigger that exists for millions of folks all over the globe! It's precisely why far too many people perpetually keep true love, prosperity and happiness at arms length (out of fear)~ while they TELL themselves, "it's just due to fate or bad luck."