TravelCon 2018: On Longevity, Building Community, and the Art of Pivoting in the Travel Industry

The last time I attended and invested in a travel blogging conference was 2012. I know – seven years ago. Back then there was only TBEX, the Travel Blogging Exchange. Attending once was helpful, but it still left me with a sense of uncertainty when I returned home. What’s next? What to do with all this content and knowledge I have on Caribbean destinations? Is it worth continuing this travel photography and blogging thing?

I was on the brink – one of many we have as entrepreneurs – of deciding whether to continue or whether to switch paths.

And then I saw an email in my inbox from one of my blog readers – it reminds now of the power of community, one of the topics at TravelCon. She was alerting me to an ad from Moon Guides, searching for the next Moon Belize author. The requirements were that you had to be a travel writer with at least five clips, as well as someone who loves and knows the destination and returns often. Six years have passed since I read the email and applied.


Guidebook writing came into my life and completely took over, more than any other work I’d done. All of my time at first, and all of my focus went to my new edition of Moon Belize. I gave it my all – for one reason. And that reason wasn’t money (we all know there’s not much to be made from traditional guidebooks). My goals were credibility and experience. I knew the value of authoring a travel guidebook: becoming a top expert in your destination while being funded to do so, and establishing myself as Belize expert before travel editors (because let’s face it you don’t get selected if you’re not a good writer) and before my peers.

I remember asking a Lonely Planet author back then, as well as a Moon author (both men) for advice on whether guidebooks were worthy assignments. The rapid, negative feedback was overwhelming – in a nutshell, don’t bother! But I took it with a grain of salt because they were focused on money after over 10 years of experience, when I know that in the process, writing those books did help advance their careers even if it didn’t make them rich.

So I embraced the sacrifice. I decided to trust my gut; this was a fit for me at that stage. Besides, I wasn’t a privileged white male who could just talk my way into travel writing assignments from big magazines, or magically stand out in editor’s inboxes with few bylines. (Ironically, one of those authors I’d contacted later returned to guidebook writing. Proof that advice is good, but you should always listen to your own voice.)

After Belize came the offer to write and illustrate Moon Dominican Republic from scratch. It was a no-brainer: the DR had, and still has, the fastest growing tourism economy in the Caribbean. Here was my chance to reveal the “other” DR, beyond Punta Cana (which by the way, is a TINY percentage of the country). My chance to become the #1 English-speaking travel writer on the DR, and use the Spanish I’d studied for decades.

“Building a business is not about thinking short term. It’s not about grinding it out. Or being on a hamster wheel. It’s about having a vision.” – Nomadic Matt, Keynote at TravelCon

For those seven to eight years then, I was consumed with building my name, my writing and photography, my experience in the Caribbean region. With the little time and funds I spared, I attended travel writing and photography conferences and workshops like Book Passage, and Travel Classics. I had almost no time to follow friends’ daily posts on social media (anyone who does guidebooks can tell you how crazy life is once you take one on) and even less time for conferences or a social, family life.

But the gigs and the editors followed, as I’d hoped. They found me either online or through referrals from my peers (Belize – Oh you should contact Lily. DR? Absolutely. Jamaica? I know a writer and photographer). I became more widely published, wrote articles, online guides, marketing copy, and learned how to pitch effectively.

“Find fresh water where there aren’t other boats. Competition is for losers.” – Ryan Holiday, Opening Keynote at TravelCon 2018


Nomadic Matt hosting his first-ever annual TravelCon in Austin this month.

Since last year, I’ve felt ready to re-enter the world of travel blogging conferences. It’s an important part of the industry, and I could finally afford to make the time and invest. So when Nomadic Matt reached out and invited me to lead a photo walk for the first edition of his conference, TravelCon, this month, the timing was perfect. We’d never met, but my friend Lola Akerstrom had recommended my work. Being familiar with Matt’s work and successes, I knew it was a great opportunity.

With my photo walk students on the colorful, “Dirty 6” side of Austin.

Beyond the super fun experience of leading a photo walk – sharing my best tricks on how to shoot a place in a way that tells a story – TravelCon made me reflect back on my entire journey.

There were three main recurring themes throughout the keynote presentations, the workshops and discussions: growing an everlasting business, establishing your community, and learning to pivot.  

The JW Marriott Austin was a great spot for the conference and a great place to rest.

Indeed, I knew all too well: success doesn’t happen overnight. It took me nearly 10 years, but I created my niche and built a reputation for writing about cultural and sustainable travel in the Caribbean. And since last year, I’ve pivoted into another area of the industry: strategizing and producing editorial and destination content for tourism boards and associations.

For instance, I’m the current editor in chief for Destination Belize Magazine 2018-2019, Belize’s #1 visitor publication, about to be released in October. I’m also writing new content exclusively for the Dominican Republic’s Tourism Board since last year. These two long-term clients have kept me occupied and gainfully remunerated, aside from my freelance writing assignments. It’s been a great lesson in diversifying.

It’s clear that none of this growth would have happened without persistence, time, sweat, hours of writing, hours of honing my expertise in the Caribbean, and yes – the guidebooks, as well as my community of peers, and my blog.

A shot I captured to show the importance of unique perspectives when shooting a place.


So what’s next? At TravelCon, listening to keynotes from Ryan Holiday and Nomadic Matt in particular, I realized that it’s time to really figure out and plan my next pivot. Perhaps produce my own products and lead workshops. The photo walk reminded me that I enjoy teaching and inspiring others.

I’ve also had at least three book ideas over the last couple of years, and it’s time to start pushing those out. It’s all about growing bigger and working smarter, learning more, reading more, attending more valuable conferences to learn from peers, and finding those next-level partnerships.

As Nomadic Matt said, it’s about doing the type of work that feeds your soul, and not about pursuing the latest fad.  

I was inspired by how active Austin’s residents are.


Living in the Caribbean (currently in the DR, and before that, Jamaica and Belize), while still publishing in US outlets means that I’m often away from my peers. Social media, email, and Skype conversations are often my sole links. Being at TravelCon reminded me how important it is to be surrounded by your colleagues, old and new – for exchanging ideas, receiving or giving support and advice, and cheering each other on.

I was so thrilled to see my amazing sister friend, supporter, and mentor Lola Akinmade Akerstrom after at least five years or so (thanks for the shout out to my work in your presentation on making money from your travel photography).                       

I don’t have enough words to describe what an inspiration she’s been since I started on this path, especially as one of the few African female travel photographers in this travel industry, like myself (East and West, represent!). From our first coffee meeting in Silver Spring in 2008 to the present day, she’s been a super mentor. And by the way, it’s not a given to have a mentor, for us writers/photographers of color (but that’s an entirely different post).

It was wonderful to meet other peers and successful bloggers I’ve known online for so long, like Oneika the Traveller, Chelle Roberts of Brown Girls Fly, Ernest White of Fly Brother, Andrea Rees of Wandering iPhone whose work I knew (and realized this at the conference), and Jill Browne whose feedback on my posts has given me much food for thought. The conference had a diverse speaker line up – refreshing to say the least – as well as a meet up for bloggers of color. To the bloggers of color who were regulars at these often non-diverse blogging conferences, thank you for sticking through them and speaking up over the years on the lack of diversity at blogging conferences. It’s definitely made a difference.

As for the photo walk I led, it was a great experience in teaching again. Despite two solid downpours, my students were super focused and excited to learn.


Tomorrow, I’m heading to the most important annual conference for the Caribbean region: SOTIC or State of the Industry Conference, hosted by the Caribbean Tourism Organization and this year, The Bahamas.

SOTIC brings together Caribbean-focused travel journalists, both on the trade and consumer sides, as well as stakeholders, and tourism boards to address important and interesting topics affecting the region’s present and future.

I’m honored to have been invited to attend by Bahamas Tourism.

Follow my updates from Nassau and around The Bahamas using #SOTIC2018.

Lastly, a big thanks to Nomadic Matt for an inspiring TravelCon, to Austin for keeping it super weird, to the JW Marriott for being an awesome host hotel and to the travel blogging community for being such an energizing, inspiring bunch.

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