Jobs are still awesome.
I wrote that back in 2014, and if anything, I believe it more now than I did then. Not because I love jobs – I don’t by the way – but because I’ve now lived through what happens when things stop working.
Not in theory, not in a podcast, not in someone else’s story. I mean when the market actually freezes and the deals disappear.
Should you quit your job to go all-in on real estate?
Short answer: That’s how people blow up.
“Burn your ships” sounds great right up until the moment the market shuts down.
Keeping my job is what got me through 2008 and COVID without forcing bad deals just to survive.
When you don’t need a deal, you make better decisions.
When you do, you don’t.
A job buys you time. And in this business, time is everything.
You Don’t Control the Market
When I first got into real estate, I literally didn’t know anything about it.
Like many people, I was pulled in by the need to DO SOMETHING – ANYTHING to survive.
And once I jumped in I started hearing the same pitch from the gurus: quit your job, go all in, make more than you ever imagined.
To be fair, sometimes that works.
But what nobody tells you is that real estate, or any side gig for that matter, isn’t a straight climb. It’s cyclical. And every cycle eventually turns.
I got a front-row seat to that in 2008. Before things broke, the market felt normal, meaning active, predictable, even forgiving. Deals were there if you looked for them.
Then it stopped. Not slowed down. Stopped.
Financing dried up, buyers vanished, and anything that looked solid on Monday could be dead by Wednesday. Ask me how I know.
If you were depending on real estate as your only source of income, it wasn’t just stressful. It was a problem.
Survival Beats Skill in a Downturn
What I noticed then, and what stuck with me, was that survival didn’t go to the smartest or the most aggressive. It went to the people who could stay in the game long enough for things to recover.
And that came down to one thing: whether or not they had income coming in.
That lesson came back around in 2020. Different cause, same effect.
COVID hit and the market seized. Sellers paused. Buyers pulled back. Everything slowed while people waited to see what would happen next.
I’d already seen that movie before.
The difference this time wasn’t that I had some special insight. It was that I still had a job.
The Job Removes Bad Decisions
That job did exactly what it was supposed to do. It paid the bills. It removed the pressure. It gave me space to think instead of react.
Most importantly, it kept me from making bad decisions out of fear.
Because fear is expensive.
When you need a deal to survive, you stop being selective. You stretch on price. You justify things that don’t make sense. You take on risk you normally wouldn’t touch.
That’s how people get hurt in this business—not because they’re careless, but because they’re cornered.
Why “Burn the Ships” Sounds Better Than It Works
This is where the “burn your ships” idea starts to fall apart.
It’s a compelling story. It sounds decisive, even heroic. But it assumes that effort alone determines the outcome. That if you remove the safety net, you’ll figure it out.
Sometimes that’s true. Other times, the market doesn’t care how motivated you are.
The Cortez story gets used a lot in this context. Burn the ships, remove retreat, force commitment. That worked in 1519.
But Cortez didn’t have a mortgage.
He didn’t have kids to worry about, medical bills, or the kind of responsibilities most people carry now.
Applying that mindset directly to modern life isn’t bold – it’s often careless if you have a family to support.
The Real Advantage: Time
What a job actually provides, especially early on, is time.
Time to learn the business without panic. Time to make mistakes without consequences that ripple into the rest of your life. Time to pass on bad deals and wait for good ones.
And in real estate, that ability to wait is everything.
The money isn’t made in doing more deals. It’s made in doing the right ones.
Where People Blow It
Of course, there’s a tradeoff. Building a business while working a job is hard. It’s nights, weekends, and early mornings. It’s being tired more often than you’d like.
And this is where people start to blur the lines.
I’ve seen plenty of examples of that. People using their work email for their side business. Taking calls during work hours. Running comps on company time. Printing contracts on the office printer.
It feels small in the moment, like you’re just squeezing a little extra productivity out of the day.
But it catches up to you.
And when it does, you lose the very thing that was giving you stability.
The Job Is the Engine
If you’re going to do both, you have to keep them separate.
Your job isn’t the enemy. It’s the engine that funds everything else.
That paycheck is what gives you margin for error. It’s what allows you to think long-term instead of reacting to whatever is in front of you.
Looking Back (With More Data Now)
Looking back, I’m glad I didn’t go all in too early.
Maybe it would have worked. Maybe it wouldn’t have.
I don’t know. Hindsight isn’t always 20-20.
But I’ve seen enough cycles now to know how easily things can turn. I’ve seen good operators get absolutely crushed because they were overextended when the market shifted.
Not because they didn’t know what they were doing, but because they didn’t have room to absorb the hit.
Looking Forward (Because It Will Happen Again)
There will be another disruption. There always is.
Think about it. Jimmy Carter’s crippling stagflation, the dot com crash, 9/11, the financial crash, and COVID. Each roughly 10 years apart.
I don’t know when it will happen, and neither does anyone else. But when it does, the same pattern will play out.
Deals will slow. Buyers will hesitate. Lending will tighten. And the people who can afford to wait will have the advantage.
That’s the Game
This isn’t about playing small. It’s not about being safe.
It’s about being durable.
Because the people who last in this business aren’t the ones who move the fastest. They’re the ones who stay in the game long enough to benefit when conditions improve.
Final Thought
So no – I still don’t think you should burn your ships.
Not because you’re not capable.
But because you don’t need to.
You don’t need drama. You don’t need pressure. You don’t need to back yourself into a corner.
You need income, patience, discipline, and time.
The rest takes care of itself.
Dennis Fassett has been investing in residential real estate since 2004 while working full-time in corporate roles. His experience spans multiple downturns, including 2008 and COVID, shaping a practical, no-hype approach focused on staying solvent when markets turn.
