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I’ve always dreamed about hitting the road, traveling full-time, and seeing what the world has to offer. But like most people, my dreams come with a set of challenges. For me, it’s not a lack of desire or curiosity—it’s the practical stuff that keeps me grounded: finances, fear, and logistics.
These are real obstacles, but I’m working through them step by step. Here’s what’s holding me back and how I’m tackling each challenge head-on.
Tackling Financial Hurdles
Debt Obligations
Let’s start with the big one: debt. I have some financial obligations that need attention before I can fully embrace life on the road. That’s why I’ve committed to using Dave Ramsey’s snowball method to pay it off. If you’re not familiar, it’s simple—start by paying off your smallest debts first, then roll those payments into the next one. It’s all about building momentum, and it works.
Right now, I’m on track to be debt-free in less than five years. That might seem like a long time, but progress feels good, and it’s keeping me motivated. Once that’s off my plate, I’ll have more financial freedom to focus on travel.
Building an Emergency Fund
Another priority is building an emergency fund. My goal is to save one year’s worth of expenses—about $42,000. It sounds like a lot, but I’m breaking it down into manageable chunks. I’m using rental income from my four-unit apartment building, stock trading, and freelance income to fund this account.
Having this cushion will give me peace of mind if something unexpected comes up while I’m traveling, like RV repairs or medical expenses. If you’re thinking about doing something similar, I recommend starting with a smaller goal—maybe three months of expenses—and building from there.
Stabilizing My Rental Property
Owning a rental property is a great way to generate passive income, but it’s not exactly “set it and forget it.” My property needs to be fully stabilized before I can hand it off to my property manager and hit the road. This means making sure everything is in good shape—repairs are handled, tenants are happy, and systems are running smoothly.
I’m focusing on:
- Preventative maintenance: Taking care of things like plumbing and HVAC systems now so I don’t have to worry about them later.
- Finding a reliable property manager: I already have some prospective candidates, but I’m spending extra time to make sure they’re equipped to handle any issues while I’m away.
If you own a rental property, I can’t stress enough how important it is to invest in the right people and systems. It’ll save you stress in the long run.
Conquering Fear of the Unknown
Fear is sneaky. It creeps in with questions like, “What if this doesn’t work?” or “What if something goes wrong?” For me, the fear of leaving behind stability and stepping into the unknown has been one of the hardest hurdles to overcome.
The way I see it, fear will always be there—it’s how you deal with it that matters. Here’s what’s helping me:
- Planning for worst-case scenarios: Knowing I have an emergency fund and a plan for dealing with unexpected events makes fear more manageable.
- Learning from others: Reading blogs and watching videos from people who’ve done this before reminds me that it’s possible.
- Reframing fear as part of the adventure: The unknown can be scary, but it’s also where the magic happens.
If fear is holding you back, try writing down what you’re afraid of. Then, come up with a plan for how you’d handle each situation. It’s amazing how much lighter things feel when you have a strategy in place.
Managing Logistics and Planning
The logistics of long-term travel can feel overwhelming, especially when you’re just starting to plan. There’s so much to think about—budgets, itineraries, work schedules—and it’s easy to get stuck in the “what if” phase.
Here’s how I’m breaking it down:
- Budgeting: I’ve calculated my monthly travel expenses (around $3,500) and matched them against my income streams. This gives me a clear picture of what’s doable.
- Using the right tools: Apps like Trello help me organize tasks, and budgeting apps like Credit Karma keep my finances in check.
- Starting small: I’m planning shorter trips first to test my setup and make adjustments before committing to full-time travel.
If you’re struggling with logistics, my advice is to focus on one thing at a time. You don’t have to figure out everything right away.
Progress, Not Perfection
One thing I’ve learned is that progress matters more than perfection. Paying off debt, building savings, and stabilizing my property are all long-term goals, but each step I take gets me closer to the life I want.
It’s not always easy, but I remind myself that every small win counts. Whether it’s paying off another credit card, seeing my emergency fund grow, or handling a tricky property repair, these milestones keep me motivated.
Tips for Overcoming Your Own Obstacles
If you’re facing challenges that feel like roadblocks, here are some actionable steps to get started:
- Identify your biggest hurdle: Is it money, fear, or something else? Write it down and get specific.
- Make a plan: Break the problem into smaller steps you can tackle one at a time.
- Celebrate progress: Even small wins are worth acknowledging—they add up.
- Ask for help: Whether it’s hiring a property manager or reading financial advice, don’t be afraid to lean on resources.
- Take action: The sooner you start, the closer you’ll get to your goal.
Final Thoughts
The road to traveling full-time isn’t without its challenges, but the good news is that every obstacle has a solution. For me, it’s about tackling debt, saving for emergencies, stabilizing my property, and addressing fear with a solid plan.
If you’re feeling stuck, remember that progress doesn’t have to be perfect. Start where you are, take small steps, and don’t lose sight of what you’re working toward. Every little bit gets you closer to living the life you want.
