Is it really possible to quit your job and live off the income from a real estate investing business?

I mean, seriously… whether you're flipping land, flipping houses, wholesaling houses, or buying rental properties, you must admit, it's a legitimate question.

Back when I was getting started, I used to wonder about this all the time.

I remember having this constant inner dialogue with myself,

“I know others have made enough with this business to quit their job, but can I really do it?”

“Will I ever feel financially secure enough to do this full time? Am I just kidding myself here?”

“The real successful people got there in 18 months, but I'm still not there after 3+ years. Is this ever going to happen for me??”

You see, my journey to financial independence wasn't exactly fast.

I started my first real estate business in 2008, and it wasn't until 2016 that I FINALLY felt comfortable enough to quit my job and focus on real estate full-time.

It's not that I couldn't have done it sooner, but I'm someone who worries, overanalyzes, and overthinks decisions of this magnitude. I need to have several contingency plans in place before I do something as monumental as quitting the J.O.B.

RELATED: Six Months After Quitting My Job – Here Are My Honest Thoughts.

Even though I knew that on paper, it was technically possible for my real estate business to be a fully sustainable, self-supporting business, there was a LONG period where I had my doubts, and I wondered if all my attempts to make money in real estate would ever lead to an actual freedom from a job.

Full-Time Investing Is a Big Leap

Starting a real estate business and going full-time is a big deal, and there are a lot of obstacles that need to be overcome to get over this hurdle.

Part of what makes it such a perplexing (and scary) decision is that there are a lot of different paths that can be taken.

There isn't a one-size-fits-all formula. Every person has to fight different battles as they're figuring this out.

With that in mind, we've collected several case studies from people who made it. I hope you'll see a little bit of yourself in the stories below because if you have the drive and desire for autonomy and financial freedom, you probably share something in common with each of these folks.

1. How Brett Snodgrass Built a House Wholesaling Empire.

If anyone has ample experience with the issues of investing in real estate full-time, it's Brett Snodgrass of Simple Wholesaling.

In this interview, Jaren drills down to find many answers to the questions we all have about living this kind of lifestyle.

Can you quit your job, survive and thrive with a real estate investing business? How are you supposed to manage your finances and pay for your overhead expenses while also paying yourself? How do debt and taxes factor into the overall picture? What are the biggest challenges with this kind of business and lifestyle?

2. Going From 0 to 10 Deals per Month (and quitting his job) in 18 Months

Willie Goldberg is one of those guys who didn't sit around and wait for years before quitting his job. He took the leap of faith on his first direct mail campaign, and within 18 months, he was able to transition to full-time land investing and generate $12,000 in monthly cash flow.

It doesn't always happen this quickly, but Willie's story is a great example of what can happen with a clear goal in mind and a willingness to work hard (and smart) to pursue the dream.

We actually did another, more in-depth interview with Willie on episode 39 of the REtipster Podcast, where he shared a lot more insights on how his business works and how he made the transition.

3. David fired his boss to invest in land full-time. Here's how he did it…

David VanSteenkiste is someone who jumped into the land business and took it seriously from the very beginning. With the benefit of experience from working with houses, he understood the challenges of real estate.

Part of David's story involves a partnership, which is an interesting component to think about, especially with the potential it has to grow your business faster and reach your freedom number sooner rather than later. If you're in the land flipping business and you want to grow it to the point where you have total autonomy over your life (or even if you’re considering jumping into the land investing game as a beginner), David is a great example of what’s possible when you take this business seriously and take action on building your financial freedom.

Check out the show notes from this interview with David on episode 36 of the REtipster Podcast. You can also check out David's website at Mile High Rural Land.

4. Self-Employment Tips from a Self-Employed Financial Advisor

The challenges of self-employment aren't exclusive to real estate investors. Everyone has to overcome some big obstacles to earn this kind of financial freedom.

In this interview, I chatted with my college buddy Chris Wiesehan about what it took for him to become a full-time financial advisor. Given Chris' expertise, he also shares some of his guidance and suggestions for how someone can leap from a day job to pursuing their actual dream in a financially prudent way.

Want to learn more about Chris? Check out his website at CJW Capital.

5. From Full-Time Employee to Full-Time Entrepreneur

While we're on the topic, I thought I'd share this interview as well. Shortly after I quit my job in 2016, my friend Sharon Vornholt was nice enough to sit down at record an interview for her podcast about what my experience was like.

To see more details on what my experience was like, check out this blog post.

Different Paths for Everyone

Remember, there is no cookie-cutter approach to quitting your job.

It's also possible (even preferable) to continue working your job even though your business is making enough to support you. There are a lot of stories of folks who have generated more than a full-time income from their business while working it on the site – but they continued to stick with their job until they were ready to leave.

• 003: Finding Your Groove As A Land Investor. Interview w/ Karl James
• 006: Callie Build a Full-Time Income in 11 Months. Here's How She Did It
• 010: How Jaren Barnes Changed His Life With One Land Deal
• 013: This Is What Happened When Greg Took Action

Have you leaped full-time self-employment? Do you have any tips or suggestions you'd like to share with the REtipster community? Let us know your thoughts in the forum!