The basics up until now:

• Education: Five years of undergrad and three years of graduate school. First two years of college was paid for by sports. I transferred to a school closer to home, quit playing ball, and changed my major. I had some academic scholarships at my second school but took loans to cover the difference. Grad school was largely paid for via assistantship, but some living expenses covered each year with loans. I left education with $45k of student loans.
• First job (age 24-27): $42k and suffering in a shit town in a shit state. I drove a hand-me-down Camry that broke down every few months, but at least I didn't have a car payment. I was blowing cash at bars, putting things here and there on credit. I made contributions to retirement though and paid each month on my student loans. I didn't miss payments when I was carrying credit. At that time, an emergency costing $1000 would have absolutely throw me for a loop. I did not keep savings and would often spend down to my last dime the night before my paycheck would hit. I have no idea where my money went. In retrospect, my mid-20s were pretty rowdy and I wasn't living a lifestyle based on the future.
• Age 27: My dad dies around my 27th birthday, leaving around $80k life insurance, which felt huge at the time. I worked with a financial advisor and landed on a "bucket" strategy. One bucket was "life changes" (put $17k toward a brand-new Honda Fit leaving me with a very low monthly payment and took a couple months off work to find a new job in a bigger city; I spent about $4k total to move once I found a job). Second bucket was "debt" (I paid off around $30k of student loans, leaving me about $10k at the time to continue to resolve on my own consistent with a 10-year payoff plan). Third bucket was "savings" (I maxed Roth contributions for the next 3 years and set aside a chunk for "something else down the road").
• Second job (age 27-30): $58k but now I'm on the east coast, and I'm still creating my own suffering. I moved into a house that I (in retrospect) couldn't afford. Same ol' shit with me: I'm still blowing cash at bars, fast fashion, and splurging on too many little trips a year to catch this concert or join this friend, etc. Still sometimes putting things on credit. I open the second bedroom in my house as an Airbnb and things start leveling out with a little extra income. I'm still making retirement contributions though, and I have the rolling contributions set aside from my windfall into my Roth. I'm paying car insurance, and car and student loans payments, but they are both pretty small. I'm still living paycheck to paycheck and an emergency costing $1000 would have thrown me for a loop. After two years in the house I couldn't afford, and with some affection building for my east coast city, I purchased a house in 2019 just before my 31st birthday. It's a great house but has sat on the market for six months due to known foundation issues and a seriously dated kitchen, so I receive "seller help" for closing costs on a $130k mortgage and immediately throw the $25k I had set aside to fix the foundation and remodel the kitchen. My realtor says it's a savvy purchase -- I got a great deal on a house that had fixable issues. My cash on hand made possible what others could not swing. Thanks dad.
• Age 31: The Pandemic hits and I am laid off. I receive a severance of about $8k, and I'm with the bulk of Americans receiving quite a bit of unemployment and stimulus money. I coincidentally sobered up in January of 2020, so not only is everything shut down and spending overall drops dramatically but the main instigator of spending (my drinking, which windfalls into eating out, losing/breaking shit, other problem behaviors that require money to fix) has fallen away. For the first time in my life, ironically during unemployment, I consistently have a comma in my bank account. I'm off work for about five months. I did a ton of hiking and camping. I'm laying low and it's a beautiful time in my life -- I know myself for the first time in sobriety, and I don't feel pressed to get right back to work. I work with a recruiter to re-enter the workforce in the fall, and it pays off.
• Third job: (age 31-current): Started at $95k, currently at $104k, fully remote from the start. After a few paychecks, I'm breathing. I begin aggressively paying off debt with my jump in salary (I financed the kitchen appliances and had some left on my car, student loans, and some consumer credit). I rent my house out for a year in 2021 to live my grandmother who is struggling to find regular home care during the pandemic. Rent coming in and low living expenses while providing care are providing more and more space. There is still consistently a comma in my bank account. I figure out how to use an FSA, and I resume contributions to my Roth. I'm saving for retirement at 9%. Grandma headed to a home as things progress beyond me and I did the digital nomad thing for a few months to kill time until the one-year lease is up on my house. I get back home in 2022 and I immediately remodel the basement (partially financed construction) into a finished apartment. Within 3 months, I'm making $1k a month from a roommate. There's a catch here during this time: from 2020-2022, I'm dating someone who is not working, and we enmesh quickly during the pandemic. She was laid off early in the pandemic (worked retail) and just lived on unemployment, even after the big stuff dried up. Eventually her unemployment totally dried up, and she bounced around menial jobs for a few months -- a cafe, a gym, a boutique. I essentially carried us both at times, and she never fully contributed to living expenses. This wasn't the right person for me and retrospectively, my support of her caused a lot of resentment between us. I can't go back in time but looking back...I gave too much in that situation.
• Currently: I've been making good money for several years, and the cumulative impact on savings and emotional health are tangible. I've been living alone for over a year now, consistently having the extra rent from the basement apartment coming in. I've received merit raises each year, and last year I won a company award that came with a cash prize. I still have some debt related to home improvements (financed roof repair at 0%, to be paid off before offer period ends). I also have the very tail end of my student loans to resolve. I have savings -- enough to write a check to resolve plumbing or electrical here and there -- but not enough to pay cash for whatever major house repair needs to happen next (for example, I need to upgrade the electrical in my 100 yrs. old home and the full job done right is gonna be around $7k). Knowing that I am saving though, via retirement contributions and having cash in a separate account that doesn't count toward what I can spend in a month, is incredible. I'm still sober. I buy new camping gear when I need it and I say yes to trips and can pay my share up front. I don't stress when I split the bill with a friend and their plate cost more than mine.
• Looking ahead: I'm dating someone who finishes law school in May. She has a job lined up for August and her earning potential is high. We've been escalating slowly and despite my lingering debts, I feel confident in our conversations about finances. I'm about to be 36 and I still feel behind, but on paper...I'm not drowning. I could resolve these 0% interest credit balances, I just don't. We just started couples counseling as we look ahead to joining households after she finishes school. I never thought I would be in a situation where my HHI would pass the $200k ceiling but it looks to be on the horizon. I never dated people like her in my 20s, and my most recent ex...I thought that's how life would go for me, that I would always need to assume that I would be the one making the money.

Thanks for reading this far, if you have. My net worth is inching toward $100k, the bulk of that being in my retirement accounts and the Roth IRA. I have the option to sell my home or rent it out when she and I combine, and I'm still on the fence. After paying what's left on the mortgage, I would net around $100k. I have it listed for rent online at $2k a month and am getting bites. I don't have to decide now. Like I said, I'm hitting my stride, and it's been a decade in the making. I'm grateful my young, dumb, drunk self never messed with my retirement elections. Despite my relationship with my father while he was alive (complicated) and the tragedy of his death, he continues to care for me. $80k isn't a huge amount of money for someone's life to be distilled down to, but it was instrumental in my arrival here. I am not rich yet. I'm barely a high earner. I'm just on my way...