OP . I can understand how a run-in like that can make you feel inferior to this loser-cum-executive guy. Don't be fooled by the suit and expensive car, he might be a PA or EA sent out to fuel up the boss' car! People mixed up in drugs (not saying he still is) often became world-class liars, very believable and convincing. But if he was for real, then good on him! So nice to hear of someone turning around their lives for the better.
It really saddens me to hear that young Mums don't feel they've accomplished anything. I'm with Shoopuf & Clementine. The priviledge and joy of motherhood far exceeds any material things and stuff money can buy.
Old school acquaintances on my FB would consider my DH & I to be living it up. Me in an executive job with regular overseas trips, DH with his own successful company, built our dream home, drive new cars, go to concerts, have weekends away, etc. But they don't see our struggle to start a family. To them we look like a childless-by-choice couple with time & money to do anything we want. It wouldn't surprise me at all if they thought we were selfish show-offs. Yet I would walk out the front door with nothing but the clothes on my back if there was a guaranteed child in my future.
Study, careers and money can come at any time, it is not too late for you to set and achieve life goals. My DH didn't start his company until he was 34. Until then he worked in pretty menial jobs, and at times multiple jobs. My ILs struggled all their lives and finally bought their first investment property when FIL was 60. Now he is 72 and they are very comfortable in their retirement.
Please don't think you have nothing to offer your family & that you've done nothing with your life. You only have to look at your kids to know that isn't true . I hope you can find a sense of satisfaction in being a Mum for now, and use this incident as a trigger to start looking at your options career-wise.