"Feeling" is entirely subjective. I have a weird relationship with money -- terrible fear of ending up on a park bench, while still wanting All The Things -- and so I never actually felt like I was "getting ahead." I just realized at about 45 that I was ahead and needed to let go of all of the angst and drama.
There were several points along the way when I thought I had it made. I couldn't believe it when I got my first job at $57K -- my mom had never made more than about $30K in her life! And then I started and realized I needed to pay my mortgage and car loan and save for the future and wondered how I'd ever do it -- and I felt more vulnerable than ever, because that year was the first big legal market crash, and I realized that I was on the hook for the condo mortgage even if I lost my job.
When I got married, I totally thought I had it made -- $180K/yr DINKs! We bought a townhouse and had decent new-ish paid-for cars and took a honeymoon in Greece, and I couldn't even conceive of that amount of money. But after about a year I was looking at the houses in the same development and realizing we couldn't afford them even at our salary, and reading Conde Nast traveler about people paying $350/nt at some fancy resort and realizing we couldn't afford that, and wondered how people ever were able to afford that sort of thing. Plus the commute and hours were killing me, and I couldn't figure out how to balance that with wanting to have a kid.
When we moved to CO was probably the best -- had enough money to ski periodically and buy my own equipment, though still didn't understand how people could afford to buy a place on the mountain. Built our dream house and was blissfully happy with it and couldn't believe I could own something like that. But then the job went away and we had to sell and move, and carrying two mortgages for a year brought me back to that horrible vulnerability I had felt early on.
When we moved back to the east coast and I made partner I again thought I had it made. But the extra income was more than offset by the higher COL and ridiculous daycare expenses, especially after we added #2, not to mention a major home renovation.
I should note that this whole time, we were maxing out our 401(k)s and saving significantly beyond that. But as long as I continued to focus on what I didn't have and kept inflating my lifestyle, I never felt like I was making progress. Even when we hit $1M invested, it was a letdown, because that still wasn't enough to support the lifestyle we had come to expect.
After about 20 years I finally started to get my head on straight. I loosened up and agreed to take a big vacation when DH got double vacation one year, and that experience made me realize that I was being really stupid to worry so much when I could afford to do something like that. I started building my stoicism muscles more and focusing on how little I needed vs. how much I wanted. I was really driven by being poor as a kid, and by losing the CO house, but when I realized that between savings and cutbacks, I would never have to lose this house even if both jobs went into the shitter, it was like a light bulb went off and the stress went away. We also chose to live in a neighborhood here where are salaries are well above average, so I am not surrounded by conspicuous consumption every day -- and I no longer read those magazines that make me feel worse instead of better.
This is a very long way of saying that my "feelings" about getting ahead were very powerful, but also very divorced from reality. If you want to be happy and content sooner than I managed, start working on ignoring what other people have and building your own resilience and stoicism muscles, so you grow the confidence in yourself to know that you will able to handle whatever comes.
