If you spend a lot of money on an extravagance or do something else which may trigger external judgement, then you don't have to focus on what kind of milestone this may or may not be.  Instead, consider what this course of action symbolizes in your life and whether you're okay with it.  When was the point at which you began to nurture the mindset of self-acceptance?  Maybe you've never learned? When did you decide to learn it's fine to do certain things at certain times?

Raising self-awareness involves asking questions about why you decide some decisions are evil or negative or undermining who you are.   What is your underlying motive for self-criticism?  This is the predominent question.  You may have arrived at a pivotal turning point in your life.  This has nothing to do with finances, and everything to do with your self-view and understanding of the world.  Your mindset is the critical thing which decides on the value of comfort or discomfort.

Step back and reflect on your general view of education and learning.  Do you see these specific initiatives as generally a positive or negative thing?  Do you sense you deserve good things in life? If not, then underlying explanations you discover will teach you about your judgement and why you may hold yourself back from more fulfilling people, situations and events.  Learning to accept life with all its ups and downs means you learn to accept yourself and not be ashamed of anything.  You learn not to regret past choices either. 

Challenge yourself to disregard any experiences, objects or perceptions you believe to be bad.  Ignore reasons why other people want you to think you experience quiet desperation.  Shift your thoughts and educate yourself to alter experiences.  How? The transformation will happen when you're ready.  If only part of you is ready to evolve, another part of you will still hold you back. It's all or nothing.

You can learn to see everything as having potential to empower you and cause events to unfold as if through you.  You can evolve to believe that you're effective, productive, talented and useful even when you didn't feel this way before.  You never really get a firm grasp on right and wrong because your attitude defines the fine line.  Learn not to prevent your own effective action.   Choose instead to learn how you can make positive changes in yourself and inpire them in other people.