By Scotty Moe

Thirteen years ago, Erica and I got married and bought our first townhouse. I already knew I loved real estate and dreamed of owning rental properties. So after a year of living in that place and making some minor upgrades, we bought another townhouse and rented out the first one. That little "house hack" gave us a few hundred extra bucks a month. It worked so well that we ended up moving four times in six years, repeating the same strategy. That run eventually ended when I realized my pregnant wife might kill me if I made her move again. I like cash flow. I also like being alive.

Those early years planted a deep desire in me. I didn’t just want to become a full-time real estate investor. I wanted freedom to control my schedule, provide for my family, and create something with no cap on income or impact. I just didn’t know when or how I’d actually get there.

If you’re closing deals on nights and weekends and wondering when you can go all in, this one is for you.

When the Dream Got Real

In 2020, TJ and I had already partnered on a few real estate deals. But right as COVID hit, we decided to take a bigger swing and launch our own real estate company.

There was only one problem.

I couldn’t afford to quit my W-2 job.

Entrepreneurship is exciting. Overdraft fees are not.

At the time, I was working at a church in the small groups ministry. It was a great job with amazing people, but I could feel that my season of working for someone else was coming to a close.

Even so, the idea of walking away was terrifying. I had no clue if I could provide for Erica and our two kids while building something from scratch.

So I didn’t quit right away. Instead, I spent the next two and a half years burning the candle at both ends, working early mornings, late nights, and weekends, trying to figure out one thing:

"When will I be ready to leave my 9-to-5?"

Here’s what I learned, and what I believe you need to have in place if you’re asking the same question.

Most of what follows builds toward one number: your runway. That’s the amount of money you need to cover a full year of life with zero new deals closing. Mine was $120,000, and here’s how I got there.

6 Requirements for Quitting Your Day Job

1. Prove You Can Consistently Find Deals

Build a track record of flipping or buying rentals across different market conditions. Not just during a hot streak.

Ask yourself: can you still win when things get hard?

2021 and 2022 were strong years. Then 2023 and 2024 hit and the market stopped cooperating. If I had walked away in 2021 without a runway, my real estate career might have ended faster than TJ’s NFL career. That runway is the only reason I made it through two hard years still standing.

2. Track Your Spending Like Your Future Depends on It

Create a detailed monthly budget. Separate essential expenses from discretionary expenses. Then track every dollar.

Cut things you don’t need and learn to live below your means.

For me, that meant no more prepper purchases. I owned enough gear to outlast the collapse of society and not enough cash to outlast a bad summer. Priorities.

3. Budget for Health Insurance (And Then Cry About It)

Don’t guess. Go price out a real health insurance plan. Add that number to your "when I quit my job" budget.

Spoiler alert: it was astronomically higher than I expected.

I also looked into health sharing options like Christian Healthcare Ministries and Medi-Share, which are common among self-employed folks and often cheaper than traditional coverage.

4. Plan for Taxes

When you’re self-employed, you pay both sides of payroll tax. That’s 15.3% right off the top, plus your income tax.

So even if you earn the same amount you used to make at your W-2 job, you actually take home less.

The upside? There are plenty of deductions that will apply to you, such as home office, car mileage, and marketing spend. If you do real estate investing right, and have a good CPA, you’ll probably pay way less in taxes than most people with W-2 jobs. Legally, of course.

5. Build a 12-Month Runway

Make sure you can survive for a full year even if you don’t close a single new deal.

By the time I quit in 2022, my number was $120,000, which was roughly twelve months of my family’s actual expenses. Here’s how I got there:

• $60,000 emergency fund, enough to cover six months on its own

• $3,000 a month in rental cash flow, conservatively estimated, so $36,000 over a year

• $25,000 minimumfrom flips that were already in the pipeline

That’s $121,000. One full year of expenses covered without closing a single new deal.

6. Once the Runway Is Built, Run Like It’s Shorter

Here’s the part nobody warns you about.

The runway is not permission to relax. It’s a countdown clock. The day I quit, I had twelve months of cushion and zero excuses. That cushion existed so I could work without panic, not so I could coast. Every month that passed came off the clock, and the only way to add time back was to produce.

At a job, showing up is most of the battle. On your own, nobody notices if you show up. They only notice if you produce.

So build the runway. Then act like you don’t have one.

The Leap

In the end, it took two and a half years of working both my job and our real estate business before I felt ready.

When I finally quit, it was one of the most freeing moments of my life.

Don’t get me wrong. It’s still hard. I still live by the 12-month rule and keep a full runway in place.

And no, I still haven’t restocked the bunker. If society collapses in the next year, I’m going to be very annoyed about my timing.

But I wouldn’t trade this journey for anything.

If you’re stuck at a desk wondering when your time will come, just know this: it’s possible.

Build your runway first. Then jump with both feet. And hustle like it all depends on you.