Struggling the first time you try something new—whether in real estate investing or any part of life—can feel frustrating, but it’s actually a sign that you’re on the right path. In this video, I explore why we struggle, how it’s a natural part of learning, and the steps you can take to minimize setbacks while maximizing success. I share relatable stories, practical tips, and strategies to help you approach challenges with the right mindset and tools. If you’re ready to build momentum and turn struggle into success, this is for you.
For a complete guide on optimizing and scaling your real estate investments, download my Freedom Blueprint! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!
What if struggling, what if struggling, excuse me, what if struggling the first time is actually a sign that you’re on the right path? Let’s uncover how to turn that struggle into a success. Stay tuned until the end for my go-to strategy for having first-time success, even in the face of challenges.
Let’s talk about when we learn something for the first time or when we try to master something new. We’re going to struggle, and yet we forget that as adults. We don’t think it applies to us because we’ve already mastered so many things, and we’ve already learned so much. How could we possibly struggle with something new? And yet, we do.
If you know me, you know I have three young kids, and this year my oldest—my daughter—learned how to rollerblade. She had maybe roller-skated a couple of times before, and that was it. This year, she decided she really wanted to learn how to rollerblade. And of course, when we got her the rollerblades, we also got all the safety equipment: the knee pads, the elbow pads, the wrist guards—the whole thing. Because everyone knows that if you’re learning to rollerblade for the first time, you’re going to fall. That’s expected.
We got her the safety equipment so that when she fell, she wouldn’t get hurt. We know she’s going to fall. No one learns to rollerblade and becomes decent at it without falling. And yet, when we as adults go to learn something new for the first time, we don’t realize we’re going to fall. We don’t prepare for it, and we don’t think about how we can start safely or set ourselves up for success.
Struggle is part of the process. We’re going to fall metaphorically, and yet, what can we do to have our metaphorical wrist guards, elbow pads, and knee pads so that the falls don’t really hurt us? That way, we can learn from them, get better, and ultimately be successful. Struggling the first time we do something is natural. It can lead to growth and mastery if we approach it wisely.
Let’s talk about the challenges of trying something new in real estate investing and where I see many investors struggle. The first area is finances and accounting. Navigating budgets, taxes, and cash flow systems can be overwhelming the first time. Most people don’t feel comfortable with this in their everyday lives to begin with. For many, mental blocks around money come into play, like avoiding finances because you don’t want to face them. Then there are skill gaps, like budgeting, taxes, and cash flow forecasting, which are essential for real estate but aren’t part of most people’s personal lives. It’s easy to feel thrown into the deep end and struggle with this area.
The second struggle I often see is when people venture into long-distance real estate investing. It’s scary, and the fear of it keeps many people from trying—yet long-distance investing was transformational for me. It allowed me to tap into better markets and learn how to be a hands-off investor, leveraging systems instead of my own sweat equity. People often rely on proximity to make investing easier: swinging by properties, handling tasks themselves, or knowing the local market. Long-distance investing challenges you to step out of that comfort zone, and it can feel overwhelming at first.
Third, anytime you enter a new market or strategy, there’s going to be some struggle. If you’ve mastered long-term single-family rentals and decide to break into RV parks, for example, you’re going to stumble. Things won’t work the same way, and that’s natural. It’s okay to not perform as well in a new market or strategy as you did in the old one because you haven’t mastered it yet.
So why does struggle happen? First, it’s a lack of experience. You don’t yet have the knowledge or wisdom to draw upon because it’s your first time. Second, unrealistic expectations set you up for frustration. Like learning to rollerblade, if you don’t anticipate falling, you’re unprepared. Adults tend to think they’ll get things right on the first try, but when we don’t, it can feel jarring. Third, the absence of support systems can make struggles harder. When we don’t prepare for struggles, we don’t seek out mentors, tools, or resources to help us bridge knowledge gaps.
So what can you do to maximize success the first time you try something new? First, start small. Think of this as your minimum viable product—your proof of concept. If I’m moving from single-family homes into RV parks, I’m not going to buy a huge RV park as my first deal. I’ll dip my toe into the shallow end, start small, and learn from mistakes on a smaller scale before scaling up.
Second, seek resources like mentorship, coaching, or education. If I’m exploring RV parks, I’ll find an expert—whether through a podcast, a course, or a Facebook group—to learn from their experience and bridge my knowledge gaps.
Third, invest in research and preparation. Real estate investors tend to be decisive, “high-D” types who want to jump in. I get it—I’m like that too. But sometimes it’s valuable to pause, take a breath, and do the research to set yourself up for success.
Fourth, ask yourself, what’s the worst that could happen? Write it out. List the worst-case scenarios and assess their probability. This helps you manage unrealistic fears and prepare for realistic risks. If you’re overly optimistic, it keeps you grounded; if you’re fearful, it helps you take action. I also recommend using tools like ChatGPT to show you potential blind spots.
Now, my go-to strategy for success is to focus on one small win. Momentum is powerful. It builds confidence, skills, and results that compound over time. Like rolling a tiny snowball into a huge snowman, small wins grow into big wins if you keep building. When you start something new, focus on achieving one small win. Then build on that, one step at a time.
There will be challenges, missteps, and falls. But by focusing on small wins and taking it step by step, you’ll turn struggles into progress and those small victories into bigger successes.