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Category: Lessons Learned

The Global eSIM That Wasn’t Quite Global

Posted on by Roberta Hill

I have become very fond of eSIMs. After years of hunting for SIM kiosks in airports, squinting at tiny plastic cards, and wondering if the plan I just bought would last three days or three minutes, eSIMs feel like a small miracle. Install it once, travel anywhere, and your phone simply works. That’s the promise anyway. And most of the time it does. For the past couple of years, I’ve been using the Discover Global plan from Airalo. It currently advertises coverage in 130+ countries, which is extremely appealing if you bounce between continents as much as I do. But…

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You Can’t Go Back. And Sometimes, You Shouldn’t.

Posted on by Roberta Hill

I have always believed in returning. Not in the sentimental, “let’s recreate that perfect sunset from 1987” kind of way. That’s a fool’s errand. I mean returning with curiosity. Returning knowing the café has changed hands, the museum has added a wing, and the once-empty square now has a gelato line that rivals airport security. Returning not to duplicate, but to discover what time has done. If you go back looking for the same experience, you will be disappointed. If you go back looking for something different, the possibilities are endless. And yet. There are places you cannot return to….

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A Short Course in Canadian Winter Physics

Posted on by Roberta Hill

I’ve learned that when people say they want to visit Canada in winter, what they usually mean is pictures. Snow on rooftops. Snowflakes drifting politely downward. Snow that looks very Instagram-compliant. What they don’t realize is that snow here has a personality. And that personality is: I’ve been here longer than you. Three things snow never tells visitors—and Canadians never explain. If you’re coming north in winter, there are three things you need to understand. Not tips. Not suggestions. Laws of nature The first is walking. We need to talk about walking on snow, especially the kind that looks perfectly…

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Passport Stories – Not about stamps but about the mistakes

Posted on by Roberta Hill

When we think of passports, we often think of the stamps we used to collect. Little rectangles of proof that we’d been somewhere else. What we don’t picture are airport counters, side rooms, or quiet sentences that begin with, “I’m sorry, but…” The Passport You Meant to Bring Even careful travellers get this wrong. My mother once left her new passport safely at home so it wouldn’t be stolen… and travelled with the expired one instead. At the airport, there was a polite pause, followed by my father becoming quietly incandescent. A notary was summoned. An affidavit was signed confirming…

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An Honest Report From the Bonus Content Department

Posted on by Roberta Hill

I’ve learned something mildly humbling, slightly irritating, and oddly freeing about the people who read me. They are not here for my digital products. This is awkward, because I love making them. Checklists, prompts, planners, toolkits, clever little systems with tidy names—these are my happy place. I enjoy thinking through problems and turning them into something useful, downloadable, and mildly bossy. It feels productive. It feels professional. It feels like something one should be doing if one is a Serious Creator on the Internet. My readers, however, appear largely unmoved. They don’t light up when I mention a new bonus….

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Hack vs Tip: A Completely Unnecessary Distinction

Posted on by Roberta Hill

I’ve come to believe that the difference between a travel hack and a travel tip has very little to do with usefulness and everything to do with personality. A tip says, “Arrive early for immigration.”A hack says, “THIS ONE TRICK BORDER AGENTS DON’T WANT YOU TO KNOW.”Same advice. Different blood pressure. A tip is something you remember because it makes sense and works.A hack is something you screenshot, forget, and then rediscover three months later at 2 a.m. while doom-scrolling. Here’s my working definition, for what it’s worth: Label What It Really Means Tip Practical advice learned through repetition, mistakes,…

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The Trouble With Age, Experience, and Other Convenient Myths

Posted on by Roberta Hill

Age doesn’t automatically give you experience or wisdom. I’ve never really bought into that idea, neat as it sounds stitched on a pillow. I’ve always believed that if you’re going to make a big mistake, you should make it while you’re young. That’s when the consequences sting, but don’t scar. You learn, you recalibrate, you move on slightly wiser and a lot more alert. My first proper scam happened in my early twenties, in Greece. I was taken for sixty dollars. That doesn’t sound like much now, but at the time it felt enormous. Sixty dollars was meals, bus tickets,…

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I’ve Hated the Law of Attraction for 25 Years

Posted on by Roberta Hill

Here’s Why—and Why Today’s Travel Advice Smacks of It I’ve disliked the law of attraction for a good twenty-five years. Long before it had hashtags. Long before it was repackaged as mindset coaching, abundance culture, or “energy-led living.” I didn’t hate it because it was optimistic. I hated it because it quietly blamed people for circumstances they didn’t choose. And lately, I’ve realized why so much modern travel advice irritates me in the same way. It carries the same scent.Different language. Same logic. The Original Problem: Blame Disguised as Empowerment The law of attraction always sounded generous on the surface….

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How Travel Taught Me to Read the News Differently

Posted on by Roberta Hill

It has been a tough week globally. Being informed no longer feels like a civic duty. It feels like endurance training. Staying Awake Without Staying Agitated There was a time when staying informed meant the morning paper, a radio bulletin on the hour, and the comforting sense that the world could wait until tomorrow. Now the world refreshes itself every six seconds, usually in ALL CAPS, and somehow expects you to care deeply about everything, all at once, before your coffee cools. I’ve learned—slowly, imperfectly—that awareness does not require constant exposure. You can stay engaged with what’s happening in the…

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The Places I Still Mourn

Posted on by Roberta Hill

If I say them out loud, it isn’t casually. It isn’t for provocation. It’s because silence can start to feel like misrepresentation. Hong Kong I loved visiting Hong Kong for its velocity, the choreography of streets, the vertical drama, and the way life moved with purpose. I had hoped to go back for a proper visit. But now there is a tension I won’t unfeel. The political weight in the air, the sense of being watched more than welcomed, the carefulness in conversation. That self-censorship would alter the texture of the trip. China China has always loomed large for me:…

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