How to Build a Land Business That Actually Gives You Freedom

How to Build a Land Business That Actually Gives You Freedom 

By Jill DeWit 

A lot of people say they want freedom. They want more time, more money, more flexibility, and a life that doesn’t feel like it’s owned by a calendar they didn’t design. 

But what most people really mean is: “I want freedom… without accidentally buying myself another job.” 

That’s the trap. You’ve probably seen it happen—someone buys a small business, starts a “side hustle,” or invests in something that sounds exciting, and then two years later they’re working harder than they ever did at their W2. They didn’t buy freedom. They bought responsibility… with no exit plan. 

So let’s talk about how to build a land business that actually gives you freedom—real freedom, in the ways that matter. 

And yes, we’re going to talk about land investing online too, because if you want freedom in today’s world, the ability to operate from anywhere isn’t optional—it’s the whole point. 

Freedom isn’t just money—it’s control 

When people hear “freedom,” they usually think financial freedom first. That makes sense—money removes pressure. It solves problems. It gives you options. 

But I think freedom is broader than that. Freedom can mean you’re not tied to an office. Freedom can mean you can be anywhere you want and still operate your business. Freedom can mean you control your schedule instead of someone else controlling it for you. Freedom can mean you wake up and decide you’re going to work today—or not—because you’ve built a business that doesn’t fall apart when you step away. 

That’s what we’re talking about here: building a land business that supports your life, not one that consumes it. 

Step one: be honest about whether you actually want freedom 

This might sound strange, but it’s one of the most important parts of this whole conversation. 

Not everyone truly wants freedom—even if they think they do. 

Some people need structure to be productive. They need someone telling them where to be, what to do, and when it’s due. They might hate their job… but they function well inside the container that job creates. 

And then they get a blank slate. 

They sit down with an empty calendar and complete control over their time, and it’s suddenly terrifying. It’s like every day is Saturday… and they don’t know how to turn Saturday into progress. 

If you’re building a land business, you have to be willing to create your own structure. You have to be willing to decide: “This is what I’m doing today, and I’m doing it whether I feel like it or not.” That’s the difference between wanting freedom and being able to handle it. 

So the first question isn’t “Can land investing work?” The first question is: Can you manage yourself? 

The Land Academy model is built for location freedom 

One of the reasons land investing has always been so attractive to us is because you can do it from anywhere. 

We’ve proven that in every way possible. We’ve worked from other states. We’ve worked from other countries. I remember distinctly logging in from Paris years ago and reviewing listings and photos with our team like I was sitting in an office. We’ve done deals while traveling. We’ve done deals living in an RV. We’ve done deals while spending months on a boat. 

That’s not luck. That’s design. 

A land business gives you freedom when you build it around deals that don’t require you to physically show up. We’re not letting contractors into houses. We’re not managing remodel timelines. We’re not tied to properties “around the corner.” The entire model is built around buying and selling land in markets that work, with processes that can be handled remotely. 

That’s what makes land investing online such a powerful path for people who want the ability to live and work anywhere. 

The part people don’t want to hear: you’re going to work hard at the beginning 

Freedom is earned on the front end. 

If you’re serious about building a pipeline and getting traction, there’s a season where you’re going to work 10–12 hour days. Not forever. Not because it’s glamorous. But because you’re building the machine. 

You’re learning the business owner learning curve. You’re creating a system. You’re filling a pipeline. You’re building confidence by doing the uncomfortable things repeatedly until they become normal. 

And this is where people get it twisted: they expect it to feel easy right away, because the business is simple. But simple doesn’t mean effortless. 

If you apply yourself for a couple years—really apply yourself—you can end up with a business where you have consistent deal flow, consistent income, and the kind of flexibility most people only talk about. 

The business owner learning curve is real—and it changes everything 

There’s a moment that happens when you’ve been “doing the work” long enough where it stops feeling like you’re constantly bracing for impact. 

You suddenly realize you’re not fragile. You can handle problems. You can handle a surprise. You can handle something not going perfectly. 

That confidence isn’t something you read about. You earn it. 

It’s like learning to dock a boat. You can watch videos, talk to experts, and study for a long time—but at some point, you have to do it. You’re going to mess it up. You’re going to bump into things. You’re going to learn what weather changes. You’re going to learn what happens when conditions aren’t perfect. 

Land investing is the same. You’re going to misjudge a situation. You’re going to price wrong at least once. You’re going to have a seller who’s confusing. You’re going to have a deal that takes longer than you thought. You’re going to have moments where you feel like you should already “know this.” 

And you have to cut yourself slack. 

Because if you hold yourself to the standard of doing it right the first time, you’ll be disappointed forever. Progress comes from repetition. Confidence comes from doing the thing 100 times—imperfectly at first—until you get good. 

The real secret: focus on the freedom you’re building, not the discomfort you’re in 

If you want to stay in this long enough to win, you need to keep your eyes on what’s on the other side of the early grind. 

When you’re in the setup phase, it’s easy to get frustrated by details. You can get annoyed at the learning curve. You can get overwhelmed by all the moving parts. 

But what helps is focusing on the outcome: the freedom you’re building. 

A couple years of doing deals—building skill, building pipeline, learning how to handle whatever comes up—can create a situation where you’ve got steady income coming in every month and the ability to actually choose how you spend your time. 

That’s the trade: effort up front for freedom later. 

Freedom looks different for everyone—and you need to define yours 

This is where most people skip the most important step. 

You need to decide what freedom means to you. 

For some people, freedom is purely financial. They want enough cash and investments generating interest income so they can live on that and never “have to” work again. 

For other people, freedom is creative. They want to build something because it’s an expression of who they are. They want to create an experience, a product, a restaurant, a brand—because that’s their version of a meaningful life. 

And for others, freedom is geographic. It’s waking up and saying, “I don’t feel like doing this today. I want to go somewhere else.” It’s being able to travel, relocate, or build your life without asking permission. 

None of these are wrong. But you have to name yours. 

Take a day and write it down. Not vague. Specific. What does your ideal week look like? Where are you living? Who are you with? How do you spend your mornings? What are you no longer forced to do? What kind of work—if any—still feels fulfilling? 

If you don’t define it, you can’t build toward it. 

Goal setting: the math is supposed to lead the decision 

Once you define freedom, you need to set goals that match it. 

That includes financial goals. Some people want to pay off debt. Some want to replace their income. Some want to retire early. Some want to create “freedom money” that gives them options. 

This is where we use tools like the Equity Planner—because goals aren’t just wishful thinking. They’re numbers. And numbers can be reverse-engineered. 

If you know what you want, you can work backwards. You can build a plan that tells you how many deals you need, what your average profit needs to be, and what actions need to happen weekly to stay on track. 

This is where land investing online becomes especially powerful—because you’re not limited to what’s in your backyard. You can build toward your goals by selecting markets that fit your numbers, your lifestyle, and your time. 

The plan is what creates freedom—because it removes randomness 

It’s easy to say, “I want freedom.” 

It’s much harder to design a business that delivers it. 

A real plan answers questions like: 

• What kind of deals align with my lifestyle? 

• Do I want deals that require me to be physically present? 

• Do I want to keep it simple with remote land flips? 

• Do I want to scale using funding so I can do more and bigger deals? 

• Do I want “boots on the ground” support so I’m not tied to location? 

For us, that plan has always included a few simple principles. 

First, we chose deals that didn’t require us to be physically present. Second, when something did require physical presence, it wasn’t us—it was trusted people we put in place. Third, we structured our business so it could operate while we were traveling, on a boat, or anywhere with a reliable internet connection. 

This is what turns land investing into freedom instead of a life sentence. 

If you want freedom, build a business that can move with you 

A land business gives you freedom when it’s built with intention. It’s not automatic. It’s designed. 

You define what freedom means. You set goals that match it. You create a plan that turns those goals into actions. Then you commit to the early work long enough to build confidence and pipeline. 

And if you’re willing to do that, you can create a business that doesn’t just pay you—it gives you your life back. 

That’s the real promise of land investing online: not that it’s effortless, but that it’s possible to build something that works anywhere… because it’s built to.