I grew up fairly poor. Not because my parents didn't make money, but because they didn't want to spend it on their kids. Everything in my life was as cheap as possible for them. They wouldn't spend money on us unless they absolutely had to, and if they did, they'd get us the cheapest crap they could find.
In college, I had a decent job and scholarships, but I took out student loans anyways to cover all my expenses so that if I lost my job I'd still be able to go to school. Well, I never lost my job, and ended up just spending all that money. I had never been spoiled and decided to spoil myself. After I graduated, I was making $48,000 per year and felt rich beyond belief. A couple years later my wife graduated with her masters and together we were making over $100,000. DINK's! (Double Income No Kids). It was fun. We bought whatever we wanted. We would get credit card statements in the mail that had to be sent in large envelopes because there were too many pages to fold. We would usually pay most of it off, but never paid anything additional towards the student loans. The student loans just seemed too large to worry about. Probably about $65,000 in loans between the two of us. We rolled our credit card balances around on various 0% offers we would get in the mail, so never paid interest on the money. I was always worried one day we wouldn't get another offer before the introductory rate ended.
When we were 24 we got married, then bought a house. We made enough to cover the bills and didn't get too much further in debt, but we spent pretty much everything we made. We "had" to furnish the new house and eventually "needed" new cars. That was probably the lowest my net worth ever was.
I knew we weren't making the right choices, but it was hard to stop. We took trips to Disney (wife never got to go there growing up), we went to the beach, on cruises, etc. In 2006 my wife got pregnant and we realized we had to stop acting like children. I got my wife involved with the finances and she took over the book keeping. She is great with numbers, but when we realized what we were bringing in vs what we owed, it was a wakeup call. I will never forget one night waking up to find her crying because she was so worried about money. We both vowed to do the right thing going forwards. We committed ourselves to paying off bills and debt and we stuck to it.
We worked our freaking asses off for years. We lived well beneath our means for years, and we still do. We eventually paid all our debts off, and are debt free. It's a liberating feeling and I'm so glad we were both on board for it. I regretted the time and money that was wasted in those early years, but at the same time it was funny to see the world with my new wife. I wish we'd been a little wiser about some spending, but honestly there are other things I wished we'd spent more on. Like our wedding, we didn't have an open bar and didn't invite as many people as we could have because we were worried about the cost. It was high for us, but it's the kind of thing you can't go back and re-do. I wish we'd done more in that respect.