Need Advice on Living a Little

Hello, I’m a 30-year-old male who grew up in a small community where a Great Depression money mindset was always encouraged. Over the last 10 years, I’ve poured myself into work, going from making almost nothing to being fairly comfortable financially. My father passed away from COVID three years ago without a will, and I was his only son. Managing his estate during my grief was incredibly challenging, but I somehow made it through. I haven’t touched my dad’s estate proceedings since, and I was surprised to learn that I had more retirement savings at 26 than my father had at 61. I placed $100k in a HYSA and invested the rest in a brokerage account. Recently, I received a lump sum of $75k from my grandmother’s estate, which I never expected due to 10 years of legal battles that I wasn’t involved in.

Here’s a look at my current financial situation:

  • Salary: $106k (pre-tax)
  • Brokerage: $258k
  • HYSA: $107k
  • Roth IRA: $38k
  • Work 401k: $22k
  • Emergency Fund (HYSA): $11k
  • Other Investments: $60k
  • Cash: $75k

Note: I’m halfway through a Master’s degree at an Ivy League school, which my employer is paying for.

I was considering buying a home until I met my girlfriend three years ago. We currently share rent on a 2b/2b apartment, each paying $1,000 per month. The topic of buying a home is difficult because she wants to build equity and is financially successful, but I have much more purchasing power. She doesn’t want to cover just 1/3rd of the cost, but I also don’t see the fairness in paying 2/3rd of a $500k+ down payment and mortgage. To me, it’s just math and numbers. I understand her desire to build wealth through real estate, but realistically, I would be the main driver of that investment.

Main Question: What would be a wise thing to do in my situation as someone who had no role models for career success or handling a large amount of assets? I’ve done well on my own before the inheritance, but now I’m wondering why I’ve never been on a vacation. I’m nervous about taking time away from work because I’m obsessed with proving my value and climbing the corporate ladder. I regret not spending more time with my dad in his last years because of this mindset, and it bothers me that I still struggle to take time off for myself.

I front-loaded my 20s into becoming the best version of myself professionally. I don’t regret it, but I’m starting to wonder if I’m even capable of slowing down mentally. I’ve only ever seen money go up and never down, coming from a place of survival. I remember nights where I went hungry because I had zero dollars in my account, and for many years, I never expected help from anyone.

Has anyone in a similar situation found resources that help in living a balanced life when you’re incredibly ambitious due to a stressful or traumatic youth? Thanks if you made it this far!