I am in my mid 30's and have achieved quite a bit so far - I own one company with about 30 employees, recently sold another for a large financial gain, and am the prime investor in 5 other companies. And yes, I lift. But I am miserable.

I attach a lot of value to my financial success, which I know is not healthy. I am currently reading the Feeling Good Handbook, and next up is Six Pillars of Self-Esteem. Usually, my list of goals for the year is long and detailed; this year I have two: 1 - Meditate Daily; 2 - Get Happy. I picked these two goals because I have realized that I seek so much validation from others that it makes me want to puke. I recently ended a LTR because I wasn't happy; it wasn't until after it ended that I realized that I am not happy with myself or accepting of myself. I read through my journals from the last 2 years and I really feel bad for that guy, because most of the entries are me yelling at myself for not hitting my big habits/goals each and every day. I constantly catch myself talking about me and my accomplishments and dreams on dates, and rarely make it "about her". One date told me afterwards that she couldn't even get a word in; I have no recollection of it. So,obviously, I'm trying to fix this, but also I'm kind of scared to fix it because what if it ruins my edge?

Anyways, my question is this: When a woman asks what I do for a living, I clam up. I get a ton of anxiety and feel embarrassed; I say "Well, I do a few things..." followed by rambling and rambling about investing, my industry, etc etc. How can I give an answer that is confident and not long-winded? How do I talk about myself in a way that doesn't seek validation? Also, outside of those two books and meditation, how can I start loving myself more?