The story behind Tripper by Sandra Henriques

The story behind Tripper by Sandra Henriques

In a nutshell, I was born in 1978 (I’m a “xennial,” that glitch of a generation between Generation X and Millennials) on S. Miguel Island. A few days later, I flew back to my home island, Flores.

My birth certificate shows S. Miguel as my island of birth, but the truth is Flores is my island of origin. It’s where I grew up and where I lived until I was 17. When people ask me where I’m from (the red hair and almost-American accent when I speak English rules me out as Portuguese), I answer, “I’m from the Azores” because it’s easier for me to sum it up like that.

Between 2004 (when I finished College) and 2013, I worked a series of odd jobs, which led me to a somewhat comfortable position in a multinational company (from 2007 to 2013). Although I don’t like to mix the blog with my corporate past, one only exists because of the other.

I always wrote. I don’t think it’s easy or an anyone-can-do-it skill. Writing is emotional, and it has been like that since my very amateur short stories at age 10. 

During that short-lived corporate career, a trainer once asked my group during a training session what we would be doing if we could choose another job. Without thinking, I replied, travel writing.

That was in 2011, and to this day, I have no idea why that came out. I wasn’t traveling that much or yearning to. I wasn’t reading any travel-related books. I was definitely not aware of the new era of travel blogging.

Let’s just say that a series of disappointments at work led me to acknowledge I was at the wrong place and that “hating to be told what to do” was probably more than a personality trait.

In the spring of 2013, I was determined to leave the company but had no clue where to go from there. Buying a domain and a theme seemed like an affordable investment to get started. Picking up on that urge to become a travel writer, the obvious next step seemed to start a travel blog.

Yes, I know how that sounds. The entry bar is so low that anyone with a computer and an Internet connection can do it, right? True. But most of those fail six months after going live. Some hang on for almost a year. That’s fine. Just because something is easy to start doesn’t mean it’s less valuable or easy to maintain.

Like in any industry, there is good, and there’s bad.

But back to the story behind the blog and my decision to take the leap of faith into travel blogging.

I was suggested the name Tripper: it’s a synonym for traveler. It’s also an adjective for myself, as I trip a lot. I get distracted and shuffle my feet when walking. Or maybe my mind is always rushing, and my feet have trouble keeping up. Whatever the physical reason, my father would often tell me, “Sandra, lift your feet” throughout my life since I learned to walk.

Tripper is me, and I am Tripper (corny, right?). Tripper started as my online writing portfolio (and still is) and grew to become my independent creative outlet. I write in English because I believed I’d reach more people this way. I also have loads more fun writing about travel in English than I do in Portuguese.

When I launched Tripper in 2014 (officially), I struggled to write an “About” page. I wanted the blog to have my voice, but I didn’t want to be the center of the story. The problem with that was that in June 2014, I hadn’t yet found my voice, nor my blogging style, nor the topics I was passionate about. 

I had no technical skills. My previous blogging experience had been some amateur endeavors on Blogspot, LiveJournal, and WordPress — free templates, endless rants, blurry photos of day-to-day life. You know? Those years when Facebook and Instagram weren’t around yet?

Between 2014 and 2016, I must have changed my bio a hundred times. Was I a travel blogger? A travel writer? A travel influencer? No. I was none of those things, and maybe I was all of those things.

The blogging community was prolific in throwing advice at newbies like me, with one or two affiliate links thrown in for good measure. And I thought I had to be all of those things. Eventually, I felt every day that I had failed at all of them significantly.

Let me assure you that failure tastes bitter. What if the leap I took at the end of 2013 from a steady corporate job I hated into freelance writing was a mistake? Gosh, I didn’t want to be another one of those “quit your job to travel” people because, quite frankly, at the end of 2015, I wasn’t traveling that much (outside of Portugal at least). I felt like a fraud by travel blogging standards.

On the other hand, I was starting to get some work as a freelance ghostwriter (sometimes it was travel-related, sometimes it was not). In mid-2016, I was invited to freelance for Lonely Planet as a Lisbon Local.

Other cool clients and publications followed, and I felt I had finally broken through into freelance travel writing. Yet, I looked at my blog, and I was nowhere near the success I was (allegedly) supposed to have achieved by then.

What was the reason for “failing miserably” as a travel blogger? I was following everyone else’s path instead of my own. Quite obvious, right? Well, from the outside, it is. 

I wanted to stand so much out of the crowd that I called Tripper a blog on “cultural tourism to offbeat destinations.”

That was a little closer to my heart and my traveling style (if there is such a thing). Still, the content didn’t quite reflect it — places like BarcelonaDubai, and Bangkok weren’t exactly offbeat. I struggled to make my past and future content fit that tagline. 

What followed could have been a case of being at the right place at the right time, but I see it as simply grabbing an opportunity.

My two homes, Lisbon and the Azores began to rise in popularity as tourist destinations in 2016. There was very little content about them, apart from institutional websites such as tourism boards. The little content that was out there about them was one-sided (and, short-sighted too, most of the time).

Tired of seeing typos like “Barrio Alto” instead of Bairro Alto or reading other bloggers talk about “hidden gems” in popular neighborhoods like Chiado, I tackled Lisbon first. 

Writing as a local for visitors gave me leverage: I got to show them a Lisbon they didn’t know existed while preserving the privacy of residents (who were already feeling the first effects of overtourism in Lisbon).

Writing about the Azores came naturally, and I used the content to close an information gap that’s not new: articles about S. Miguel (one island) pretending to be the whole of the Azores (one archipelago).

But, I didn’t want to be *that* blog that writes about specific locations, partly because blogging is not my primary source of income. So I didn’t want to be stuck with something that would be time-consuming.

2017 was the year for sustainable tourism. I watched dozens of bloggers change their taglines to include “sustainable” or begin to write SEO-based posts (for non-bloggers, that’s a blog post written around search results on Google) on the topic, even if they had no authority or expertise in the matter.

I, too, had changed my tagline at the end of 2016, and Tripper had become “the sustainable cultural tourism blog,” but not because of a fad. People who worked in the sustainable tourism industry welcomed that tagline with awe and affection. Still, I knew I was limiting my audience to a tiny niche.

Business-wise, it might have been a bad call for a full-time blogger. The writer in me, though, was thrilled. There it was: my voice, the topics I was passionate about, all of my creative energy.

As a traveler, I don’t have the illusion that you can see a destination as it’s supposed to be seen. Even I’ve stepped into many tourist traps in the past, thinking I was experiencing something unique and typical. Travel is an experience. Period. You affect your destination, and it affects you.         

Tripper might have been born at the end of 2013 in a hotel in Bangkok, but it came full circle in those first weeks of 2017. For the first time, my content calendar made sense. I had ideas faster than I could write about them. I actually felt happy about traveling again because I’d find a story to tell anywhere I went.

Tripper is my creative outlet and where you can come for content on the three things I’m passionate about when traveling (regardless of where I’m traveling to):

  • Minimizing your negative impact on tourism destinations
  • Supporting small, local businesses
  • Discovering local culture