9 simple rules I wish I knew before my first solo trip

Stepping onto a plane alone for the first time felt like jumping into a cold lake—shocking, bracing, unforgettable.

I’d planned routes, downloaded maps, and still spent my first night eating crackers on a hostel bunk wondering what on earth I’d done.

The good news? You learn fast when you’re on your own. The better news? You don’t have to learn the hard way.

Here are nine rules I wish someone had handed me before that first solo leap.

1. Plan the skeleton, not the skin

“The map is not the territory,” as Alfred Korzybski once noted—and he’s right.

Your plan should be a flexible outline, not a rigid script. Book the first two nights, sketch the “musts,” and leave space for the good stuff you can’t predict.

I used to cram itineraries like I was speed-running a video game. Then a local tipped me off to a tiny vegan pop-up in Lisbon that only opened on odd days if the surf was calm. No guidebook could have planned that. Give yourself permission to say yes to the unplannable.

Keep a simple system: one anchor (lodging), one aim (experience), and one option (backup) per day.

That’s enough structure to prevent chaos and enough slack to meet serendipity halfway.

2. Pack to carry, not to check

If your bag makes you sweat, you packed your fear. Solo travel rewards agility—running for a train, climbing hostel stairs, squeezing into a tuk-tuk. Aim for a single carry-on and a daypack. If it won’t fit, it stays home.

I pack a “one-week capsule” even for a month: quick-dry basics, one nicer outfit, one warm layer, one rain shell, and running shoes that double as walking shoes.

Toiletries? Solid bar versions wherever possible. Tech? Phone, charger, universal adapter, earbuds. That’s it.

Every extra item is a tax on your attention. Keep your hands free for coffee, maps, and high-fives from strangers.

3. Safety is a habit, not a gadget

Safety isn’t a secret money can buy—it’s a set of routines. I do a five-minute “situational reset” each time I enter a new area: scan exits, sense the vibe, clock a landmark, check phone battery. Then I move with purpose.

I register my lodging address in my notes (offline), share my live location with one person I trust, and set a recurring “check-in” reminder that I physically tap “done” on each night. If I don’t tap it, my contact pings me. Simple beats fancy.

One more habit: learn how to say “excuse me,” “no,” and “help” in the local language. You’ll use the first constantly; the second rarely; the third, hopefully never—but having them ready calms your nervous system.

4. Your mindset makes the weather

Before my first solo trip, my brain ran disaster simulations like it was auditioning for a thriller. Then I realized something: we suffer more often in imagination than in reality.

Notice the story you’re telling yourself when plans shift.

Flight delayed? That’s not a failure; it’s a bonus chapter. Restaurant closed? Not rejection; redirection.

You can’t control the forecast, but you can carry your own microclimate.

A practical trick: name your “trip intention” in a single verb—notice, connect, learn, wander. Then when decisions pile up, pick the option that serves that verb. It keeps you anchored when your inner narrator gets dramatic.

A note on a book that helped: I’ve mentioned Rudá Iandê’s work before, and I recently finished his new book, Laughing in the Face of Chaos: A Politically Incorrect Shamanic Guide for Modern Life. The timing was perfect.

On the road, little frictions can spiral into self-judgment, and his insights cut through that. One line I underlined for this very reason: “When we let go of the need to be perfect, we free ourselves to live fully—embracing the mess, complexity, and richness of a life that's delightfully real.”

The book inspired me to treat missteps as material, not mistakes, and it made my travels feel more like an experiment than a test. If you’re heading into your first solo adventure, his perspective on authenticity over perfection pairs beautifully with a flexible itinerary.

5. Learn to eat alone without your phone

This one felt awkward at first. Sitting at a table for one with a glowing screen is the default escape hatch. Resist it—at least for the first ten minutes. Order. Look around. Smell the kitchen. Make eye contact with the server. Say yes when they suggest “the thing they just made.”

Some of my best conversations started because I wasn’t buried in a feed. The barista in Porto who drew a tiny octopus in my latte foam. The vendor in Taipei who taught me the word for “crisp” while I fumbled with coins. Solo doesn’t have to mean solitary.

If you do want a book or article, pick something that matches your intention. I like to bring a slim paperback that fits a jacket pocket. Meal times become mini-retreats rather than scroll breaks.

6. Talk to strangers like a local-in-training

I’ve mentioned this before, but the difference between a tourist and a temporary local is curiosity.

Ask specific, low-stakes questions: “Where do you get coffee around here?” “What would you order if you were me?” “Is there a street most people miss?”

The quickest way to puncture your assumptions is to put yourself in the path of ordinary, generous people. Practical starter kit: learn hello/please/thank you, numbers to 10, and “I’m learning—can you speak slowly?”

When you show effort, folks meet you more than halfway. And if you’re vegan like me, memorize a short script about what you eat and don’t eat. It turns “No cheese?” from a hurdle into a conversation.

7. Budget is freedom, not restriction

Money anxiety can stalk you across time zones. Solve it with a simple structure you can follow on autopilot. I create three buckets: fixed (lodging and transport), daily float (food, local transit, small attractions), and fun (treats, tours, surprises).

I pre-load the daily float on a travel-friendly card and keep the fun bucket in cash so I can literally see it shrinking. It makes choices easier and guilt-free.

I also keep a “non-negotiable floor” for sleep and safety—if I have to pay a bit more to stay in a better-lit area or skip a midnight bus, I do without debate. That small rule has saved me far more than it cost.

Two pro tips: pick one souvenir theme (postcards, small prints, spices) to avoid buying a suitcase worth of “just because” items, and track only once per day so you don’t spend the whole trip as your own accountant.

8. Systems beat willpower on the road

You don’t rise to the level of your goals; you fall to the level of your systems.

If you want to journal, make it a bedtime ritual with a two-sentence minimum. If you want to run, sleep in your gear and pick a loop near your stay. If you want to read more, set a 10-page rule with your morning coffee.

My system for staying plant-based while traveling is simple: map one nearby market, one bakery, and one fully vegan spot within walking distance of each new bed. Then I screenshot their hours. Breakfast handled, snacks handled, treat handled. Decision fatigue drops. Energy rises.

Here again, Rudá Iandê’s lens helped. His insights on listening to the body landed while I was deciding whether to push through a packed day or slow down. The book inspired me to treat physical signals as data, not interruptions—especially when traveling.

He reminds us that emotions are messengers, not enemies; on the road that might show up as a “nope” that keeps you from the late-night detour you don’t actually want, or a sudden “yes” that leads to the rooftop concert you’ll never forget.

9. Keep the ending in mind from the start

Trips don’t really end when the plane lands—you carry them home. So design the re-entry. A zero-commitments first night back. A simple meal waiting in your freezer. A note to your future self in your calendar: “Unpack. Laundry. Download photos. Text the people you met.”

I also keep a tiny “debrief” page in my notes with three lines: Next time bring…, do more of…, do less of…. It’s unglamorous and incredibly useful. The next trip starts smoother because the last trip taught you something.

And one more thing: write a quick message to someone who helped you—barista, host, new friend. Gratitude is a bookmark you’ll be glad you placed.

Final notes

A first solo trip is mostly a conversation with your own expectations. You’ll find out what you cling to and what you can drop. You’ll discover that discomfort tends to peak right before delight.

And you’ll realize how many parts of the world are set up, not to trap you, but to welcome you.

To borrow a final nudge from psychology, confidence often follows action, not the other way around. Self-efficacy grows through mastery experiences—small wins that prove to you that you can handle what comes next.

The first time you navigate a foreign metro, order dinner in another language, or adjust calmly to a curveball, you’re building a kind of inner passport you can carry everywhere.

If you’re looking for a companion to that inner work, I’ll say this plainly: I’ve mentioned Rudá Iandê before, and his new book—Laughing in the Face of Chaos: A Politically Incorrect Shamanic Guide for Modern Life—was a timely guide for me as I prepped for another solo journey.

One passage I copied into my notes was this: “Fear walks beside us from our first breath to our last, and in its presence, we are united with every other human being.” There’s a comfort in that on a night train or a new street at dusk.

The book inspired me to treat fear as a traveling companion with something to say, not a monster to outrun—and that single shift made me braver and kinder with myself on the road.

So plan the skeleton. Pack light. Practice safety like a ritual. Eat with your eyes up. Ask better questions. Budget for joy. Build simple systems. And land softly when you return.

The rest? That’s the skin you’ll grow on the road. And if you want a grounded, slightly rebellious map for the inner parts of that journey, Rudá Iandê’s Laughing in the Face of Chaos is a worthy place to start.