Before You Travel, Ask Yourself: Are You Really Ready for This?

Random snap of flowers I thought were really pretty.

Before you book that ticket, pack your bags, or start romanticizing your future Instagram captions, ask yourself: Am I truly willing to challenge myself? Because here’s the deal—travel isn’t just about sipping aesthetic drinks on a beach (though, yes, we love that). It’s about expectations vs. reality, setting yourself up for success (or failure), and the brutal truth that starting from zero often means maintaining zero longer than you think.

So before you dive headfirst into an adventure, let’s get real. Ask yourself these thought-provoking questions:

1. What’s the REAL reason I want to travel?

Is it because you genuinely want to explore, learn, and grow? Or are you just bored, running from responsibilities, or looking for an escape hatch from life? Travel won’t fix what you’re avoiding—it’ll just slap a different time zone on it.

I spent years running from reality. For a while, it worked—until I found myself back in the same story, just a different location. It wasn’t until I defined my goal, addressed my personal baggage, and acknowledged the need for change that I broke the cycle. Even now, this trip started as a vacation but turned into an escape. The difference? This time, I know exactly what I’m avoiding and what I need to do to keep moving forward.

2. Do I have an actual plan, or is my ‘plan’ just vibes?

Spontaneity is great! But there’s a fine line between being adventurous and being wildly unprepared. Are you budgeting properly? Do you know what happens if your funds dry up mid-trip? A dream without a plan is just a very expensive detour back home.

As a founding member of #TeamNoPlans, I get it. But even the most spontaneous travelers need a foundation. My approach? A loose plan with a destination, budget, and an escape route. If I hit a financial threshold, I know it’s time to turn back and regroup. Up until recently, I wasn’t the one making the plans—I relied on group trips or seasoned travelers. Even now, if I want to explore, I hire a guide. No shame in that. It’s a great way to get familiar with a place so you can wing it next time—or just fully enjoy the experience this time.

3. Am I setting myself up for success, or am I self-sabotaging?

Are your goals realistic? Or did you set the bar so high you’d need a jetpack to reach it? Expecting five-star experiences on a two-star budget? Reality will hit hard. Define what success looks like for YOU and set goals that don’t require miracles to achieve.

Knowing my travel needs helps me budget realistically. When I was younger, hostels were fine. Now, approaching 50, I want my own room and bathroom—but I also don’t need a luxury hotel where I feel underdressed in the lobby. I’m happier eating street food on a plastic chair than dining at an overpriced restaurant. Your travel style matters. Be honest with yourself about what you want so you can plan accordingly.

4. What happens if I don’t hit my goal in time?

Let’s say you planned to save $5,000 in six months, but month five rolls around with only $1,200 in the bank. What’s the move? Do you push your trip back? Adjust your destination? Sell everything and become a nomadic yoga instructor? (Tempting, but maybe not sustainable.)

When you’re starting from zero, it’s a marathon, not a sprint. If your timeline is tight, you’ll quickly find out whether your plan is realistic or just wishful thinking. If you want something bad enough, you’ll find a way—within reason. I still haven’t figured out how to get paid just for existing, but hey, some dreams are worth holding onto.

5. Can I handle the discomfort?

Travel isn’t always comfy. Delayed flights, questionable hostels, weird food mishaps, lost wallets—it’s all part of the game. Are you adaptable? Can you roll with the punches, or will every hiccup send you into existential crisis mode?

If you have an Excel spreadsheet for your itinerary, cool! But if you can’t handle deviations, you’re in for a rough ride. Flight delayed six hours? No problem—time to network, find a lounge pass, and snack my way through the wait. Things I can’t control: the flight. Things I can control: my response to it. Lesson learned? A certain credit card grants access to airport lounges, and once I’m employed again, I’m getting it.

6. If I’m starting from zero, am I ready to maintain zero?

Starting over sounds exhilarating until you realize it means actually starting over. No financial cushion. No backup plan. Just you, a suitcase, and the eternal quest for free WiFi. Can you handle living frugally until you reach your goal? If not, adjust your approach before you find yourself stress-Googling “how to make money fast overseas.”

Right now, many in my community are transitioning from traveling the U.S. in their RVs to selling everything and going abroad. I’m not stress-Googling yet—I’m mapping out the next decade (or lifetime). This trip might be a once-in-a-lifetime experience, but I’m returning home with the belief that it’s just the beginning.

7. What am I willing to sacrifice to make this happen?

Every ‘yes’ to travel is a ‘no’ to something else. Are you okay skipping daily lattes, cutting back on nights out, or picking up extra work shifts? Dreams cost money, and unless you’ve unlocked a billionaire cheat code, sacrifices are part of the process.

They’re the key to making this happen. Everything else is just a tool. My current tool? Warehouse work at a company we’ll call ‘Big A’ (because they don’t need free advertising unless they pay up). It’s brutal on my body, but it funds the dream until I find a better option. I’ve sacrificed comfort, but I’ve also sacrificed happiness too many times to live up to other people’s expectations. I don’t have all the answers. I don’t have a history of wealth or travel-savvy business ventures. I’m not an entrepreneur—I’m just stubborn. And I will see Singapore’s airport.

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Ready to Make It Happen? Here’s What to Do Next:

✔ Define Your ‘Why’ – Clarity fuels motivation.

✔ Make a Plan – Vibes alone won’t fund your trip.

✔ Budget Like a Boss – Track every dollar (even the ‘essential’ impulse buys).

✔ Stay Adaptable – Adjust goals, but don’t abandon them.

✔ Embrace the Challenge – If travel were always easy, everyone would do it.

Dream big, but plan smarter.

If you’re truly ready to challenge yourself, adventure is waiting—but only if you’re prepared to meet it halfway. Now, are you actually ready? Or do you just think you are? 😉