Doing well financially but can’t stop thinking about money

I just want to put this out there in case anyone can relate or has gone through something similar. I’m a 30M, and I feel like I can’t stop thinking about finances. I make about $115K, max out my HSA and Roth IRA, and my company doesn’t offer a 401(k) match. I have 10k student debt and my net worth is around 70k. We have incentive stock options, so I’ve been keeping some money liquid to buy those once we (hopefully) go public in the next couple of years. That’s why I’ve been holding off on contributing to my 401(k). I use YNAB to track my expenses and net worth, and I’m pretty disciplined about budgeting.

My partner makes around the same as I do, and we live in a medium-to-high cost of living city. We’re not living paycheck to paycheck, and I’m able to take vacations and generally feel comfortable. But even with all that, I constantly feel like it’s never enough — like I’m behind where I should be.

I’ve been into personal finance since high school. I’ve read all the books, tried all the side hustles — from options and stock trading to real estate wholesaling and even short-term rental arbitrage. Most of it didn’t really work out, except recently I’ve been doing pretty well using LEAP options in my Roth. Of course, the market’s been up lately, so it feels like everyone’s making money right now.

The thing is, this constant focus on finances and trying to figure out how to retire early or feel financially free is really taking a mental toll. I know I’m not struggling — it could definitely be worse — but I still can’t shake the feeling that I’m not doing enough. I hate the idea of just waiting for my money to compound when it feels like I should be actively doing more.

If my company’s IPO goes well, my stock options could be worth six figures. I’ve been debating whether to put that into real estate since it has so many tax advantages compared to just letting money sit in the market. But at the same time, I value the simplicity of stock investing, so I’m constantly weighing that tradeoff between simplicity and the potential upside of being more active.

For context: we rent, have no kids, and have one dog. We love the DINK lifestyle. I’m super analytical by nature — I get really deep into the details and sometimes lose sight of the big picture. I’ll catch myself obsessing over something like an extra 1–2% return and think about how much that could compound long-term. I know that mindset isn’t totally healthy.

Ideally, by 45 I’d love to have the flexibility to travel with my partner and not be tied down by work. Right now I work in financial reporting, and my busiest time is winter — which means I miss out on most of the stuff I actually enjoy that season. Maybe I’m asking for too much, or maybe I just feel like I deserve a bit more freedom. Not sure if that’s entitlement or just restlessness.

Looking back, I’ve been hyper-focused on money and finances for the past 15 years, and it’s taken up a huge amount of mental energy. Honestly, I worry that I’ll always think this way.

Anyone else feel like this?