So here I go.

I’ve got an obsession with learning new skills – from the practical (graphic design) to the seemingly useless (riding a unicycle). In the last year I’ve started to learn an unexpected “skill”. Emotions.

Those of you who know me personally know that I have this tough persona. I’ve had it for as long as I remember. Showing emotions is for the weak. In particular: showing “weak” emotions is for the weak. Showing sadness, pain, loneliness – that was out of the question.

Especially out of the question: crying in front of people. Or even admitting that I’ve ever cried at all. Before last night, I could count the number of people I’ve ever cried in front of on one hand. Women have to be especially careful about crying in the workplace. It’s a big career no-no.

About a year ago I started reading this book on Emotional Intelligence. I was interested in this because I’d read over and over again that EQ is a much greater predictor of career success than IQ. There were some tests in the beginning to score how emotionally intelligent you are, on four different dimensions. I scored extremely low on every single one.

I never finished the book. I only read two chapters:

One: stop treating your emotions as good or bad.
“It’s human nature to want to create two simple and easy piles of emotions: the good ones and the bad ones […] The downfall of attaching labels to your emotions is that judging your emotions keeps you from really understanding what it is that you are feeling. When you allow yourself to sit with an emotion and become fully aware of it, you can understand what is causing it.”

Two: lean into your discomfort
“Things you do not think about are off your radar for a reason: they sting when they surface. Avoiding this pain creates problems, because it is merely a short-term fix. You’ll never be able to manage yourself effectively if you ignore what you need to change. Rather than avoiding a feeling, your goal should be to move toward the emotion, into it, and eventually through it.”

So I started keeping track of all of my emotions in Day One. I’ve always got my phone on me, and whenever I felt anything, even if it was “bad,” I would lean into it, rather than suppress it. Write it down, work through it. I like to think of it as a scientific record of my emotional responses. I believe normal people call this a journal.

I started doing all this as a career-improvement move. But what I ended up getting out of it was much more valuable: a better understanding of who I am. To go through life feeling and experiencing, rather than suppressing and hiding behind a mask. I’ve still got a long way to go, but now that I’ve got a taste of what it’s like, I don’t intend on turning back.

A couple weeks ago, Amy and I started taking an acting class. This, too, I started doing because I thought it would improve my interpersonal skills, and thus help my career. This, too, has helped me in ways beyond what I could’ve imagined.

Our assignment last night was to recite a monologue that we’d found. I chose a piece that is personally relevant to what’s going through my life – a close family member of mine is fighting cancer right now.

I got up in front of the class, plopped down on the chair, opened the book, and started reciting. I didn’t think I would cry. But about one sentence in, I felt something in me break. And rather than fight the feeling of tears coming on, I just let them flow freely. Because here’s what I had: a safe environment where not only was it okay to cry, crying would mean for a “better performance.” So armed with that excuse to let it go, I did.

And when I looked up at my classmates while I was performing, there was no judgment in their faces. They were all as consumed by the moment as I was. It was hard for me to see through my own tears, but I think some of them had tears in their own eyes.

When I was done, I realized that crying in public turned out not to be such a big deal after all. I’d gotten to experience something new that was intense and beautiful. And, dare I say, it’s something that I’m even proud of. It’s something that a year ago, I would have been horrified and ashamed of.

Lean into life. When you have the choice between doing the scary thing or the safe thing, always do the scary thing.

Well, it definitely wasn’t at first. Simple solutions are almost always obvious once you see them. That’s why it’s so easy to take them for granted. But take a look at some of our earlier design concepts – some of which, frankly, I’m a little embarrassed about.

When we first thought about 520 or 90, we had this grand map idea in our head. That’s how existing solutions work, after all.

The Map Design

Okay, where do I start with the usability problems we found with this. For most people that we first tested this on, it actually went OK. But if you look deeper, the design had a bunch of holes:

• What if someone makes their start and end taps on the same side of the water? Then they wouldn’t be crossing the bridge, which is the whole point of the app. We’d have to throw up some rude error message, or figure out how to disable half the map when it came time to make the second tap.
• Some people tapped on the 520 and 90 blue circles, expecting us to give a recommendation about the bridge.
• Some people wondered why the map wasn’t showing the current traffic on the roads.
• Then there’s the fat finger problem – users are not going to be completely accurate with their taps, and you shouldn’t expect them to. So, we’d have to provide some way to start over if people screwed up their tap. Meh.

The Quadrant Map Design
So we came up with an idea to solve the fat finger problem: divide the map into quadrants! Then the user just has to hit a region. You think this would test well?

It didn’t. It was horribly confusing. Once we finally abandoned our grand map vision, we tried a list.

The List Design

This one tested decently. People understood how to use it. But, look at it. It’s so cluttered. In good design, what isn’t there is just as important as what is.

Okay, so how about a less cluttered design? We wondered whether people would get the “enter a zip code” method:

The Zip Code Design

They didn’t. Not only is it a bunch of extra annoying taps to enter in a number, people don’t always know the zip code of where they’re coming from or going to, and it’s a rude design to expect them to.

The Final Design
In the end, we combined the best parts of the list view with the best parts of the zip code method.
Here’s the super rough mockup:

With some photoshopping, you get what’s in the app today:

The asked-for feature that we cut

There’s another feature we were considering for this screen. One that is frequently suggested to us by people we show the app to: location awareness.

Unfortunately, location detection is not instantaneous. It takes the phone a couple seconds. What if the user had selected one thing, and the GPS detected another? Would we just replace their selection without asking? Or pop up an error message asking which one they wanted to use? Yuck.

You know what’s not obvious? Cutting a feature because you just couldn’t get the UI right. But it’s exactly what we did. (It’s also what Dropbox did, and that’s why there’s only one dropbox folder.)

It wasn’t easy to make this call. As engineers, we’re naturally inclined to want to come up with smart solutions that take advantage of the latest technology. It kind of bruised our egos a bit, as if we were somehow now technically inferior for not using location awareness. But, our number one goal was to create a simple design. So, at least for this release, we cut it.

Related post: How we picked the logo for 520 or 90

I guess I’ve always been pretty competitive. Sometimes it means I completely miss the point of what I’m doing. I doubt I followed through with any of the resolutions that year – if I did, it was probably by accident.

So how do we fare as adults? What percentage of people would you guess actually stick with their resolutions all the way through the year? The answer: 10%.

But it’s not the high failure rate that I have a problem with. It’s that new year’s resolutions make us complacent in writing down and sharing our goals only once a year. Life moves too fast for that – just like life is too special for us to celebrate romance only on Valentine’s day, or count our blessings only on Thanksgiving.

One year is usually the wrong time frame for a goal. You’ll have more success if you go for either extreme: seriously commit to a long-term lifestyle change, or break down the goal into smaller achievable steps.

Here’s my personal example of breaking it down – my “holiday checklist.”

And here’s how I did:

Okay, I’m not suggesting you do it like this. As a close friend told me after seeing this (endearingly, I’m sure), “You have a problem.”

But here’s what I’m trying to get across: I found it helpful to write some goals down. All of them were achievable within a couple hours or days, but most of them are part of bigger, longer-term goals. I added some stuff to the list, and didn’t check off everything. But that’s okay. Circumstances change, and priorities do too – whether it’s the big stuff, like making more time for family, or the little stuff, like deciding not to finish that book because it wasn’t living up to the Amazon reviews.

So take the time to reflect often. Make goals frequently. Write them down somewhere you can see them. And then, perhaps most importantly of all: give up on some of them.

Related post: How we picked the logo for 520 or 90

Before seeing the final logo, have a peek behind three logo concepts for 520 or 90:

Concept 1: Road Sign

This was the logo we quickly put together during Startup Weekend. It’s pretty straightforward and does the job. The next two logo concepts are ones that I created after having more time to think through ideas.

Concept 2: Or Bars

The two bars in the middle look like the double yellow line on roads. Those of you with some programming knowledge might also recognize the two bars to be the “or” logical operator, ||. True, only a small percentage of the general population would pick up on that. But with Microsoft, Amazon, Boeing, Google, Facebook, etc… in the Seattle area, a significant fraction of Seattle commuters are engineers.

Concept 3: Traffic Light

Here, the zeros and Os are arranged to form a traffic light.

Final Logo

The road sign logo (concept 1) did the job but wasn’t particularly special or interesting, so it came down to the other two.

The traffic light logo (concept 3) got mixed reception from the 520 or 90 team. Some loved it, others didn’t. It’s got a bit of a “coffee shop” vibe to it though, which is definitely not what we’re going for. There is also something distinctly feminine about it. Consider our target Seattle customer is probably predominately male, that’s not a good thing.

The or bars (concept 2), on the other hand, fit the “look” we were going for and was right for our target audience. Plus, the engineers on the 520 or 90 team just loved it.

I made some tweaks to the typography, choosing the Museo Slab typeface because it looked good with the double bars. I also added some texture to the background to make it reminiscent of the asphalt on a road.

And voila, there you have it!

Friday night: A bunch of people pitch ideas for startups. People self-select into groups to work on the best ideas.
Saturday and Sunday: Code, design, argue, eat pizza, stress out, write business plans, code more…
Sunday night: Demo what you built and explain how your startup will make money

Last weekend I went to Startup Weekend Seattle and joined the team 520or90.com. Seattleites who commute across Lake Washington (tons of Microsofties and UW students, among others) can take one of two bridges to get across: 520 or I-90. But with traffic being unpredictable, they never know which one is faster. And with the 520 tolls coming in December, cost really starts to become a factor. 520or90 will tell you which bridge is faster and which is cheaper – and by how much – so you can make the call.

Here is what for me were the best and worst parts of the weekend:

THE BEST
1. An awesome team

I’ve been in plenty of dysfunctional teams with a lot of politicking, hidden agendas, ego wars… thank goodness this wasn’t one of them. Don’t get me wrong – we had plenty of disagreements and debates over the weekend, but we all had the same goal: build this web app by Sunday afternoon. The organizers warn you at the beginning of startup weekend not to have a team of all developers (functional but ugly demos) or business folk (nothing gets built). We were lucky enough to have a good balance – with 4 developers, 3 business/strategy people, and 1 designer (me).

2. The Post-It Note style of Project Management

We kept track of all our tasks on this whiteboard in post-it notes, divided into 3 columns: To Do, In Progress, and Done. It’s always tricky in any project to figure out just the right amount of process – not enough and things are chaotic, too much and you end up inflexible and wasting time. We hit the sweet spot with this post-it board, which is an agile technique that Gabe, our team leader, taught us.

Every 2-4 hours, our team would get our noses out from the computer and do a “stand up” – spend 30 seconds talking about what we’ve been working on and moving post-its to track our progress. Throughout the weekend, the post-its slowly migrated their way across the board.

The big unexpected side effect of this post-it board for me was how big of a morale boost it was. The most memorable part of the weekend for me was a particularly good stand-up we had on Saturday afternoon where we just moved a ton of stuff across the board to the “done” column. We just all started spontaneously cheering, probably to the annoyance of the 100+ people around us trying to work.

3. Three rounds of UI design iteration before noon
My day job is at Microsoft, where we spend the big bucks on recruiting people for usability studies, getting our builds just right, and spending hours watching people under the microscope. It’s all very scientific – it also takes forever.

Usability testing doesn’t have to be expensive or time-consuming though. You actually only need to test with 5 people to catch most usability issues.

So it was pretty exhilarating for me to mock stuff up, immediately run around with my teammate Latika ambushing people to try out the prototype, observing usability issues, and mocking up another version immediately. We moved fast – doing three rounds of this before noon on Saturday. By the third time, we were happy with the design.

THE WORST
1. The food
I didn’t realize how spoiled I had gotten on my diet of “real” food – meat, fruit, veggies, and (mostly) whole grains, until I spent a weekend eating Startup Weekend food – pizza, pasta, chips and salsa… bleh. I can’t really blame the organizers for ordering this stuff – it’s cheap and most people didn’t seem to mind it. But processed food like all those white carbs are terrible for you. Definitely not the fuel you want to be running on for an event like this.

2. Pitches that have no point
There’s a reason you hear this startup advice everywhere: start by pitching the problem, not the solution. Despite the advice of the organizers, too many of the pitches started with “we are building X.” If you want to pitch successfully, try this format instead: “Y is a problem, here’s why it matters, and here’s how X will fix it.”

3. Designing under a time crunch
I can sit in my apartment happily pushing pixels, leisurely enjoying the view, and listening to Chopin all day long. Not so with Startup Weekend. Every minute I spend designing is one less minute the developer has to implement the design. Talk about pressure. Great design takes a relentless attention to the little nit-picky things. But at Startup Weekend, every design decision became a design-time tradeoff. One thing I learned from this weekend is I definitely need more practice designing under a time crunch.

Final Thoughts
Overall, I had a blast this weekend. The 520or90 team got a functional demo in time for Sunday afternoon. We still have some bugs to iron out before we’re ready to go public, but we’re all really excited because it’s been getting some local buzz.

I’ve always found it interesting how ideas and designs came to be, so I’ll walk you through how I created this logo.

There were a couple things Alex thought the logo could reflect: fun and playful, games, game development, Seattle, and community. As a logo designer, you don’t want to represent all of these concepts. Many of the strongest logos emphasize only one concept: it’s powerful because it’s memorable.

Initial Sketches

I start off with some brainstorming and loose sketches, keeping things open and not ruling out any ideas yet.

Once I got this far, I made a digital version and sent it to Alex.

Showing the Logo to the Client

When I show the first logo concept(s) to the client, I like to leave color out of it since I want the client to evaluate the logo based on the concept and not get distracted by colors.

The feedback from Alex was that this looked too bottom heavy. It’s always nice to have a fresh pair of eyes on the design, and I can see what he is talking about. Together we brainstorm some ways to overcome this.

More rounds of iteration

I spent some time playing with the tetris pieces and come up with a straight rectangular and irregular design. The tetris element of the first design seems to get lost – it starts to look more like a brick wall. So, I recommend the irregular design, which Alex agrees with. At this point I also start playing around with some colors.

Final Logo
The final step is to add some type to the logo. To complement the tetris blocks of the logo, I chose a font with bold, thick lines – Furore. The font also has a techy arcade game look to it.

The original name of SGC was “Seattle Games Cooperative.” It’s a bit of a mouthful and when laid out in typography, the “Cooperative” tended to overwhelm “Seattle Games.” Discussing this with Alex, we decided to shorten the name to “Seattle Games Co-Op,” which looks stronger.

A Few Final Thoughts

I was concerned that this design would be too busy – it’s a lot going on for a logo. For a corporate logo, this isn’t the kind of design I’d suggest. However, since it’s for a casual group, the playful style works for SGC.

Another concern I had was that it wouldn’t scale well to small thumbnail sizes which people would be seeing on Facebook, Twitter, etc.

In the thumbnail version, you can’t really make out the tetris pieces anymore, but most importantly the SGC part of the logo is loud and clear.

In the end, I was happy that the logo is unique and memorable, incorporating gaming in a creative way.

If you’re interested in logo design yourself, you should check out Logo Design Love. It’s the best book I’ve found about logo design, and it’s a quick read.