Should I Quit My Job to Go Full Time into Real Estate Investing

Should I Quit My Job to Go Full Time into Real Estate Investing?

As I write this in 2016, real estate investing is hot. Amateurism is running amok, and every other person I talked to is either in real estate investing or wants to be. And, in this environment, I hear this question often – should I quit my job to go full time into real estate investing? Let us examine this, because the answer is not void of nuance…

2 Truths about Quitting Your Job to be a Real Estate Investor

Let me begin by saying that regardless of what other rationale may be applicable to this discussion, two truths are evident.

First, if you like your job, and if showing up at the office every morning makes your heart sing, then why would you quit? Life is so short, guys. We are here on borrowed time. The essence of it all is to make every minute count, and we do that by enjoying what we do and who we do it with. So, if your job gives you pleasure, who cares what other logic there may or may not be. Keep doing what you love!

Secondly, you owe it to yourself to honestly underwrite your trajectory. If you are working in order to arrive at a certain financial position in life, then you have to ask yourself the question – if I stay in my job, and continue doing what I’ve been doing, will I arrive at the place I want to be?

This is very blunt indeed, but it’s honest. If it’s important to you to arrive at your definition of financial nirvana, then you have to come to terms relative to whether your job can in the end do the trick. If not, perhaps leaving and starting over full time in real estate investing, or something else, is a thing to consider…

With that said, let’s discuss things a bit more in-depth…

Financial Safety and Security as a Full-Time Real Estate Investor

So, for starters, let’s just say that it likely isn’t the best idea to have someone write your pay-checks. Some of you might say that I am a pessimist, but I think I am a realist. The notion of assigning control over my family’s financial security to someone else just seems illogical to me. But, this argument is so tired that we don’t need to dwell on this…but I hope you dwell on it.

A bit more focused argument would be to say that financial security is, at least in part, a function of diversified revenue streams. This is to say that while a $10,000 paycheck every month is nice, ten paychecks of $1,000 each are safer, and here’s why:

First, the mode of earning which results in 10 paychecks each month virtually guarantees a lower tax liability, which means you get to keep more of what you earn. Which in tern means that you don’t necessarily have to earn as much as someone else. On second thought, though, as long as you’re at it, why not earn more than someone else, but pay less tax than some else, right?!

We can have further discussion around this in another article, if you wish. For now,  more important is the reality that diversified income offers a significant amount of safety and resilience, which is unattainable otherwise.

Indeed, you can afford to lose SOME of your income – you just can’t afford to lose all of it at once. You can afford to experience a slowdown in 3,4,5, or even 6 out of the ten $1,000 revenue streams and still be able to pay all of your bills, and buy time to figure out how to either grow the remaining revenue streams, or replace the ones that went bad.

Financial Safety and Security of a W2 Job

On the other hand, the reality of a W2 paycheck is that it’s either all there, or it’s all gone – there’s nothing in the middle. Experiencing a slowdown in this case is necessarily catastrophic. Again, W2 income is either all there, or it’s all gone. And when it’s gone you’ve got no revenue coming in, and you are scrambling to replace not some, but all of your income…

People have often accused me of not being safe by not having a job. You know something – if I really thought that having a job was safer, I’d do it. But, the reality is that while I don’t necessarily know month to month what my income will be, I do know that I will have some income! This is great news for me, and it’s not something that most W2 employees can say about their income…

And, something else I am always sure of, which nobody earning W2 income can brag about, is that because I control how I spend my time, I am able to do the kind of things that on one hand further diversify my revenues, and on the other hand grow them!

Success Ceiling and Scalability

You see, operating on the “diversified income” side of the earning equation necessarily means that what we are doing is building systems. Guys, there are a lot of moving parts in what it takes to make money, and without strong systems, it is not possible. W2 income you are getting from your job is a testimony to that – what you are, is a piece of some else’s system. You are the reason why their system is sustainable and scalable. And without you their system would break down.

The distinction to understand is that whoever controls that system you are plugging away in benefits from stable income, because it’s not them needing to show up to do the work – it’s you. And if you don’t show up, someone else will – talk about safety… Additionally, all they have to do to make more money is to grow their system, and they do that by hiring another you 🙂

In this scenario, they win, you lose. They have safety and capacity to grow indefinitely, while the only system you can rely on is you – you are the system, and there is only so much you can do to earn more money in the 24 hours we are all given…

What I am focusing on doing differently is that instead of being a piece in someone else’s system, I chose to build my own systems. And, a necessary side-effect of this is that my revenue streams are much more scalable, which means that my growth ceiling is not predetermined.

You see, once it’s stabilized, running a system takes a lot less effort and time than working in someone else’s system. This means that I have the time to design and implement as many systems as I want.

Diversified revenue streams are simply the result of multiple systems running at the same time!

Financing of Real Estate

Well, all of that is fine and dandy, but let us be a bit more pragmatic for a minute. Yes – real estate can facilitate great systems. A rental house is what -it’s a system in a box, and once you figure out how to buy this system, and how to effectively and efficiently manage it, you can have as many as is necessary.

And now that you know this, I think you might be thinking – yep, I should leave my job and go into real estate investing full time…

There is one issue to keep in mind – financing. Most of us don’t have cash to be able to buy rentals without debt. Indeed, most of us might have enough for the down-payment, but need to use leverage for the rest…Or, of you are like me, you might be able to buy with nothing down at all.

But, something to keep in mind is that achieving conventional financing is much easier if you can show W2 income, and this means that if you are new, you might be best-served to keep your job until you grow large enough so that you don’t have to rely on conventional financing. How large is a topic for another day, but for now let me leave you with the following:

  1. W2 income forces you to spend time working in someone else’s system, which is unsafe.
  2. W2 income robs you of the time to develop your own systems
  3. But, W2 income can facilitate financing of rentals which would otherwise be much more difficult


For these reasons, unless you absolutely hate your job; unless it’s an absolutely dead-end job which earns next to nothing today and is unlikely to do any better ever, perhaps you should consider sticking it out and allowing your job to facilitate financing of real estate.

Remember this, however, your job is a necessary evil at best. Do not get comfortable living on W2 income. Save as much as you can, and invest!


  • Peggy Reply

    This is a good reminder of the usefulness of the W2. However, as someone that has been laid off half a dozen times in the past two decades and with a pending surgery laying ahead of me, I cannot count on another W2 job. I must transition from the W2 income and over to creating my own income stream. Thanks for the article Ben!

    • Ben Reply

      Peggy, the way you just put it, this W2 thing reminded me of an abusive relationship. You’re getting screwed, and yet you go back. I am not sure if this is funny or sad, but it’s America…

  • Jim Braun Reply

    Ben I liked your post. My job is dead end and low pay and no benefits and boring to boot.
    To me real estate is exciting and fun. It does have problems but I have control in fixing them.
    In a w2 you do what the boss says period.

    • Ben Reply

      Yes, there are hardships on all sides of this equation. But, at least we have control over our own lives…

  • Niko Molina Reply

    Sticking out on the W2 life for the time being for the exact reason that corresponds with #3!!

    • Ben Reply

      But, what specifically are you doing to enter the game, Niko?

  • Jesse Holshouser Reply

    For me, the goal is to build enough income through real estate to be able to comfortably quit my job, but my W-2 job is a tool I have to use to get there. I’m only 23 and still enjoying my work, so I want to build a rental portfolio with 10k+ a month before taking that step. I think that’s comfortably achievable by 30 years old. I certainly don’t need 10k a month to live comfortably, but if for some reason between now and then I lose my job, or absolutely hate it, I could leave much sooner. It’s all about security and having that freedom of choice.

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