I Quit My Six-Figure Tech Job to Sell Real Estate in San Diego (Here’s Why)

20,000 hours.

That’s roughly how long I spent working a 9-5 in the corporate world. Almost a decade across four tech startups, and in February 2026 I finally quit — without a clean plan, without a backup offer, and honestly without much regret.

Here’s how I got there.

The thing nobody tells you about a comfortable salary

The times I’ve been “content enough” at a job were never really about the work itself. It was always about the margin around it – finishing early enough to get outside, working out before my day started, playing beach volleyball or tennis before sunset. Physical activity and creative outlets are non-negotiable for me. When I had those things, I could tolerate a lot. When I didn’t, everything felt harder than it needed to be.

At one point the restlessness got bad enough that I enrolled in an interior architecture and design program at UCLA Extension – night classes online, staying up late on projects for about nine months – until it became too much on top of a full time job. I still wanted a social life. But it tells you something that I was willing to try.

The pattern across every job was the same: start excited, learn fast, hit a wall. Add bureaucracy, office politics, feeling underutilized – and I’d mentally check out while still showing up every day. I loved the people I worked with, but at the end of the day you’re still executing someone else’s vision with someone else’s rules. I don’t think I was ever really built to be an employee.

Here’s the part that kept me stuck though: I had benefits, a 401K I was maxing out, PTO, and in the last couple of years I was making close to $200K. Even when I wasn’t happy, there was always a voice saying – this is enough, this funds your life, just keep going.

And it did fund my life. The travel, the apartment, the freedom to explore. I’m genuinely grateful for all of it. But somewhere along the way I’d buried the entrepreneurial itch I’d always had, convincing myself the paycheck was worth it.

I’d had a glimpse of what the alternative felt like back in 2021 when I was writing my SF Gal blog. Fun, creative, fulfilling in a way most of my jobs never were. But I was early in my career, building stability, and it felt too risky. So I let it go and kept going.

The Moment I Stopped Running on Autopilot

By early 2026 I was going into the office three days a week. The commute was eating my workout time, I had no energy left for the things that keep me sane, and my cats were noticeably sad I was barely home – half joking, but also not. The job wasn’t stimulating, and I could feel it affecting my overall wellbeing in a way I couldn’t keep brushing off.

I still wasn’t sure about going all in on real estate – I’d started working toward my CA license a few months earlier but was barely making progress while juggling everything else. So I took a solo trip to Guatemala to clear my head. When I got back, I somehow found myself deep into a take-home assignment for a job interview – hours of work, presentation due the next morning – when my boyfriend looked at me and asked: why do you want this particular job so bad?

I didn’t have a good answer. And that was the answer.

I was on autopilot. Doing what I was “supposed” to do – protect the paycheck, follow the path, post the new role on LinkedIn like everyone else. That one question snapped me out of it. I didn’t want to keep going down that road, even knowing how lucrative it could be. A job that costs you your joy isn’t a good deal no matter what it pays.

Why real estate felt like the right next chapter

My entire career had been in business development, partnerships, and strategic sales – building relationships, identifying opportunities, negotiating and closing large deals and contracts, and being the person clients and partners trusted to get things across the finish line. The more I sat with it, the more obvious it became: everything I’d spent nearly a decade getting good at translates directly into real estate. The negotiating, the relationship building, being a trusted resource, closing — it’s all there. And for the first time, I get to do it entirely on my own terms.

There’s also something about the work itself that genuinely matters to me. Buying a home is the biggest financial decision most people will ever make. Being the person someone trusts to guide them through that is not something I take lightly. It’s honestly the same reason I started this blog – I want to be the friend who helps you make the leap, whether that’s moving to a new city or buying your first home.

For the first time in a long time I feel like I’m exactly where I’m supposed to be. And the fact that it scares me a little? That’s how I know it’s right.

TL;DR: Don’t let a comfortable lifestyle keep you from building one you actually want. The safe route has its place – but so does the leap. I’ll report back in a couple years. 😊

Thinking about moving to San Diego?

I’ve been in your shoes — researching from afar, trying to figure out if it’s actually as good as everyone says, going down a Reddit rabbit hole looking for legitimate stories from real people. I documented my entire move from San Francisco to San Diego — the neighborhoods I considered, cost of living, social life, and everything I wish I’d known before I went. If you’re seriously considering it, start there.

Why I Moved from San Francisco to San Diego

And if you’re already here and thinking about buying – or just want to talk through what that looks like – that’s exactly what I do now. My DMs are always open (@karenxding)!