My startup Yore Oyster recently launched a new publication called How I Travel. It's a look at the world's most interesting travelers through the lens of their most interesting travel possessions. We dig deep into why our featured travelers do what they do, what they wouldn't leave home without, and how travel has helped them to grow. If you haven't already seen it, check it out here.

Of course, branding this new entity as something that could both stand alone as a publication and also fit into the wider Yore Oyster portfolio was a big priority for me. So one afternoon, just hours after the first How I Travel photo shoot was held with pro YouTuber Sean Lee, I felt the creative surge to tackle the branding.

I should preface all this by saying that, though I'm comfortable calling myself an entrepreneur, flight hacker, marketer, writer, photographer, and more, I'm not a designer. So when I sat down to create the branding for How I Travel, I set out a few requirements to keep my thinking focused:

1. Scalability. Yes, of course I would be using vectors, but I mean scalable from a usability and a business perspective. Whatever I created for a logo had to be extremely versatile across different media and also conducive to the scaling of the resulting business.
2. Use of language. How I Travel is a great name that evokes a vivid depiction of what the site is about. I'd use this to my advantage by incorporating linguistics into the logo design.
3. Connection to Yore Oyster branding. While the brands should be recognizable on their own, I wanted to maintain a connection to the parent entity, Yore Oyster. This pairing helps the two to grow together and sets the stage nicely for an entire family of travel products all under the same umbrella.

With these parameters in mind, I reflected on two major things I did right when doing the Yore Oyster branding:

First, it's been remarkably helpful to have a circular logo; it's extremely versatile, and I never need to worry about it not fitting well or looking good on a particular type of media. So right off the top I decided that, while the new logo may not have perfectly equal X x Y dimensions, I wouldn't allow one dimension to exceed the other by more than 25%. That would give me the versatility I've enjoyed with Yore Oyster, while still leaving design options relatively open.

The second thing I did right with the Yore Oyster logo was choosing a single-hue, white-contrasting color scheme. I chose #f16464 as the color for Yore Oyster because it's fun to look at and I wanted to stay away from the blues that seem to dominate every other website. (I was probably also subconsciously influenced by Airbnb's color scheme, since they use #ff5a5f, a very similar shade of pink.) That said, for How I Travel I decided to use the same color scheme of Yore Oyster pink with white. An added bonus to doing this is that the more variables I can keep the same across all of my websites (in this case, button and link text colors), the more I can use a global stylesheet to make sweeping changes across each of them by changing a single line of code. Awesome. With these two things in mind, I jumped into Illustrator and started trying things out.

How I Travel is both an investigation and a celebration of the world's most interesting travelers, so I first thought that having a circle to represent the globe would be fitting as part of the logo. But when I started messing around and looking at other companies that have used the circle for the same purpose, I couldn't help but feel that the visual metaphor was overused. And as I thought more about how I see How I Travel growing in the months and years to come, it became crystal clear to me that a more accurate, lesser-used comparison was much better suited to our needs: the unification of the six inhabited continents. From the outside, it appears as though the continents are all remarkably different, but it's only someone who has traveled widely that is able to appreciate the stunning similarities between all six. The six sides of the hexagon became my representation of each of the six continents, and it's the perfect foundation for the How I Travel logo.

Once I'd decided upon the hexagon, a few more decisions surfaced: Would I put something inside the hexagon or leave it empty? And if I would fill it, what should go inside? It would be difficult to fit the words How I Travel inside without putting it on two separate lines, and I'd already taken a liking to the no-spaces-single-line look of HOWITRAVEL, so I needed something smaller.

This is where I started thinking linguistically. The letters "HIT" jump off the page for me when I see the words How I Travel, but I just couldn't find a good way to make them work. In acronym form, they're aggressive and unwelcoming, so I decided to take a more creative approach: I created all of them out of the same three shapes. With a slight slant for visual appeal, here's the result:

As you can see, the most visible letter is the H. However, if you rotate it just 90 degrees, that H becomes a very distinct I. And if you drop the bottom parallelogram from the I, a T emerges. I really like the concept of being able to draw additional meaning out of the logo with a bit more effort, so this fit really well with what I wanted.

But after I looked at it for a few minutes and set this new "hybrid letter" into different settings, I realized something was amiss; in my attempts to make the symbolism a bit less subtle, I had detracted from the strength of the centerpiece, the H. I decided that clarity trumps symbolism, so I changed the opacities from 100%, 50%, and 75% respectively to 100%, 75% and 100%. Things are much cleaner now.

I'm nearly done. All I need to do now is add in the full name for uses in external media where the logo alone won't be enough to evoke brand recognition. In keeping with my earlier rule of maintaining a less than 1.25:1 aspect ratio, the only possible spots for the name are above and below the logo, and it looks much better below. I'll throw it under there in Lato font with some exaggerated letter spacing. Convert the text to outlines, make sure everything is aligned, and I'm all set!

Yes, the new opacity setup makes the T more difficult to distinguish, but I actually like that about it. Now, with a focus on H and I, the logo all of a sudden becomes something that can be used across many different How I sites of a similar purpose. The concept of getting to know interesting people is one that can (and should) be applied to a lot more verticals, so a simple color change of this logo and you've got yourself a completely new publication that's easily linked to the original. Here are two I wouldn't mind creating in the next 12 months.

I always like to see how other people create things, so I'm offering my raw design files to anyone who wants them. You'll need Adobe Illustrator to open them, but if you've got that, send me an email with the subject "How I Travel Logo Design Files" and I'll send them your way! Feel free to do whatever you want with them.

And if you haven't made it over to see these designs in action, go check out How I Travel now!

This is the end of what I had written back in September in the days leading up to How I Travel's launch. I planned to publish this post in the aftermath of releasing How I Travel, with its intended purpose twofold: one, to clarify the brand in my own mind, and two, to demonstrate my thought process in the moment. I like to do the former to ensure I fully understand my decisions when I make them, and the latter so that years down the road I'll understand the rationale behind those decisions just as well as I did when I made them.

But there was a problem: the more I worked with the logo above, the less I liked it. Some of the components of the logo, while symbolically sound, were aesthetically redundant. The use case for the logo - namely social media icons, website favicons, and other round real estate - were far from good displays of the horizontal typelogo. And the bold brand messaging that I wanted just wasn't there. So I made a change.

I was lying in the hammock outside my apartment in Boracay, Philippines. I had been messing around with different iterations of the logo, but none of them were what I wanted. I needed a fresh perspective, and it was very clear that that wasn't going to come internally. So I sent a message to the one person I knew would be able to help: my sister, Katelyn.

Katelyn, three years older than me, is a designer in Vancouver. She's worked on a lot of unique projects with different clients, not the least of which was the coloring and typography for my Wise Words line of greeting cards (I hired an illustrator from Italy to do the character designs). She asks the right questions before starting the work, something I'm notoriously bad at doing, and has a keen eye for logos, type, and branding.

Our conversation quickly gets more technical from here, but you get the idea. We chatted about my needs for a few minutes, and I sent her two things: the first half of this post to explain my rationale and thinking for the logo as it currently stands, and the accompanying Illustrator design file so she had somewhere to start. Here's what she emailed back the next day.

I added the bold in her last paragraph there to emphasize how quickly she whipped these designs together. I spent over ten hours trying to do the same work that she did in under 60 minutes, and my results were nil. Here's the accompanying design file that her email references:

And after a bit more discussion, we both agreed that the hexagon was superfluous. So she came back with this.

It's bold. It's meaningful. It's beautiful. And I love it.

This is exactly why I hired a designer.

But in so doing, I uncovered a logical gap in my thinking.

A lot of us aren't good at delegating out the things that are important to us. We need to feel in control of those things, even if it means that they will be done sub-par.

This is the definition of backwards thinking.

Yet the opposite of this thinking is to delegate out everything. To become a specialist.

And I certainly don't want that to happen to me.

What's more exciting: being the best in the world at a single thing, or being skilled in a great number of things?

Who's more engaging: someone who can speak about a single topic from now until forever, or someone who can jump between conversations with ease?

What's a bigger risk: putting all your eggs in a single basket (a single profession, location, or relationship is a good mental proxy here), or diversifying those eggs across many skills, places, and people?

I couldn't be happier that I hired a designer to get How I Travel in shape, but I'll always approach hiring external help with caution. Not because their work isn't worth the investment - if you assess and value them properly, they always will be - but to avoid becoming a specialist whose proficiency spans just a single vertical.

Sure, specialists will always have a place in the world.

But I can't imagine a less fulfilling way of living.

If you have a project or business you need a designer for, you can see Katelyn's portfolio and get in touch here.