When You’re Scared to Do a Deal: A Three-Step Approach to Overcoming Fear in Real Estate

We’ve all been there—comfortable with routines, familiar habits, and the predictable patterns of daily life. Whether it’s using the same toothpaste every morning or interacting with the same people at work, we find comfort in the familiar. But what happens when we’re presented with a new challenge—like diving into real estate investing for the first time? That’s where fear creeps in.

This post explores how fear can impact your decision to make real estate deals and how education, preparation, and execution can help you push through that fear. Let’s dive in!


Why Does Fear Hold Us Back?

Fear often stems from change and uncertainty. Even though a new opportunity might be beneficial, we hesitate because the unknown is intimidating. Real estate investing can evoke similar anxieties—especially if you’re making your first deal. We’re conditioned to expect regular paychecks from traditional jobs, but investing introduces different risks and rewards. Accepting these new dynamics can feel overwhelming at first.

So how do you move past the fear? Johnoson Crutchfield, host of Grab the Map, suggests a three-step approach: education, preparation, and execution.


Step 1: Get Educated to Reduce Fear

The first step in overcoming fear is learning everything you can about what scares you. Understanding the ins and outs of real estate investment helps shrink the fear of the unknown.

  • How to Get Educated:
    • Attend real estate courses or join a mastermind.
    • Work alongside experienced investors to get hands-on experience.
    • Invest in mentorship or structured programs that align with your goals.
    • Follow resources like Grab the Map Education to stay up to date.

“Education costs something—whether it’s time, money, or relationships. But the knowledge you gain is essential.” – Johnoson Crutchfield

John emphasizes the importance of getting quality education. A client he worked with spent a year learning about multifamily real estate, from financing to property management, before finally taking the leap.


Step 2: Prepare with a Clear Plan

Once educated, the next step is preparation. Fear often lingers when we don’t have a solid plan in place. That’s why setting clear criteria for the types of deals you want to pursue can boost your confidence.

  • Create Your Plan:
    • Set investment boundaries (e.g., property type, market, renovation scope).
    • Build contingency strategies, like securing a line of credit or maintaining cash reserves.
    • Establish a roadmap for managing your first project—whether it’s flipping a home or renting to tenants.

John recalls a missed opportunity involving a 60-unit multifamily property. He knew the deal was good but lacked the preparation to act on it. That experience became a lesson: Without a plan, fear can block progress, and opportunities may slip away.


Step 3: Execute Despite the Fear

Even with education and preparation, fear doesn’t magically disappear. The final step is to push forward and execute your plan. Taking action builds the confidence you need to keep moving forward.

  • Overcome Fear Through Action:
    • Start small if necessary—purchase a modest rental or do a basic flip.
    • Accept that mistakes may happen, and treat them as learning experiences.
    • Remember: The first deal is always the hardest, but each subsequent deal builds momentum.

John shares a story about a hesitant investor who had analyzed multiple deals but struggled to commit. With encouragement, he closed on his first property. Another investor took the opposite approach—jumping into three deals in six months. Both paths led to growth, but the common denominator was action.

“Sometimes you just have to jump in the water and start swimming.” – Johnoson Crutchfield


Conclusion: Don’t Just Look at the Map, Grab It

Fear is a natural part of doing something new. However, by educating yourself, preparing thoroughly, and executing your plan, you can overcome that fear and take meaningful steps toward your real estate goals. The process isn’t always smooth, but every step you take strengthens your ability to manage future challenges.

If you’re ready to push past your fear and start investing, check out Grab the Map Education for more resources and support. Remember: Don’t just look at the map—grab it and start your journey today!


This post provides valuable insights into overcoming fear and turning it into action—whether you’re pursuing your first deal or looking to scale your real estate investments.

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