A longtime lurker, I’m conflicted about even posting on here but wanted to get some advice and (constructive) feedback.

Background

I’m 36F and I worked in Big Tech for nearly a decade before becoming disillusioned and joining a higher ed program.

I’ve been into saving as much as I could before someone told me, “hey, that’s FI/RE!” (Pun absolutely intended.) I couldn’t have done this without considerable conversations with other similar-minded people, advisors, and my parents (I helped pay off their house with my first paycheck, but I can never truly pay them back).

My progress

Real Estate

* 960K townhome (paid off, currently rented)

* 700K single family (paid off, current primary)

Investment Accounts

* $765K in taxable accounts

* $700K in retirement accounts

Debt

* $0 (I am terrified of debt)

Annual Expenses

* $45K/yr (lean/normal for me) to 80K/yr (bougie for me)

Seeking advice on

1. Early retirement

I honestly never thought I’d have a tough time getting a job when I decided to go back to school. Ultimately, I’m trying to pivot into an adjacent career path to the one I had but recruiters see my YOE and can’t picture me in a more junior role. So I’m essentially having a tough time getting a demotion.

All that said, the past few years in my program have been like an experiment in early semi-retirement life, and it’s been surprisingly fine. My rental covers the majority of my expenses and I have some savings that I eat through maybe $5K/year. I’m highly frugal in my day-to-day and keep my expenses low but quality of life high.

I have no idea if I’m close to my number, but I’ve always assumed it’s around $5M, given my age. I suspect that if I don’t tip the boat too much (read: suddenly become unfrugal), I’m on track?

My biggest weaknesses seem to be vacancies or issues with my rental, and healthcare.

2. Relationships

I grew up in a family that encouraged sole preoccupation with education and discouraged relationships. As a result, I’ve not really been in a relationship or anything of that sort. My flirting skills are hopeless (once asked a guy if he needed help with his taxes, and, needless to say, it went nowhere). All of this is fixable, I believe, to an extent.

However, what concerns me is that, at this point in my life, a relationship feels like more of a hazard/risk than an asset. And I really want to disabuse myself of that notion.

It might be nice to have someone to grow old with, though I am certain I do not want children.

Thoughts on how to navigate relationships (as a noob) when you have a couple dollars in your pocket?

4. Estate Planning

If none of the relationship stuff pans out, who/what entity shall I leave my estate to? Other than my parents, I’m not particularly close to anyone in my family.

I’m curious if anyone has had to make a decision like this, or has any advice. Maybe give it all to my alma mater?

3. Giving yourself permission to spend on a luxury item

I struggle with this, albeit somewhat infrequently. My latest splurge purchase was a $70 Amazfit watch that came with 2 straps (my g-d, the excess!). I wouldn’t say I’m consumed with guilt, just an unignorable sense that there’s a better use for the money.

How do people get over this after being really practiced in frugality? Do you leave a budget for a couple splurges a year?