When designing a feature for a website, for example, I typically recommend 3-6 options before choosing a “winner.” When designing a whole system of features, it’s helpful to at least think of one alternative. Sometimes the obvious answer wins, most of the time it doesn’t, and all of the time you’re better off for having thought deeply about a problem before jumping to conclusions.

There are a few reasons why you might generate lots of design ideas before settling on one:

1. Generating many ideas forces you to get your ideas out of your head and onto the some paper. At the very least, this will help you understand what you are thinking.
2. If you’re working with others, generating ideas will help to flesh out exactly what the “obvious” answer is. (Hint: it typically isn’t the same for everyone.)
3. You’re bound to think of some really cool solutions when you’re forced to think hard about a design problem. You’ll impress yourself with your creativity. Sure, some of your concepts will be less feasible than others, but that’s ok. Just generate, and worry about implementation later (though not too much later).
4. It’s a fun process, and I’m all for fun at work.

Lots of ideas, on paper

A few tips & tricks

• Just get ideas out, don’t judge them - Trust me, at some point you’ll feel a strong urge to think something like, “naaaw, that idea will never work…”. Get over it, and while you’re at it, stop being so negative. Just get the ideas on paper, and leave all the judgement to your future self.
• Don’t think every idea has to be hugely different, just focus on little changes - Maybe you won’t generate whole new ways of thinking about your topic, but will think of a million little tweaks you could try. That works! Just go with it.
• If it becomes really difficult, stop - This should go without saying in many avenues of life. Seriously though, if you can’t think of any more concepts, you’re done. This does not, however, give you license to quit early. Sometime concept generation takes a little practice.
• Don’t worry if your sketches are more like scratches - As long as you understand them, it doesn’t matter one bit.
• Use a 6-up template to guide your designs (PDF download) - This 6-up is from Leah Buley and it’s straightforward enough. Print one out and give it a try.

Have fun generating!

Taken from Groupon - Who is this?

Who the heck is that woman? And why is she the face of an icon? Answer: Why not? Most people probably never question this image, but it adds a level of “interestingness” to the page. My bet is that it’s just a picture of someone who works at Groupon…or perhaps it’s Rapunzel. We may never know.

Happy Birthday, joshe!

However, there are so many glaring mistakes in this email, it’s hard to choose where to start. How about this, I’ll start with two simple questions:

1. Who sent this email?
2. Why was this email sent?

The first question is relatively hard to answer. I’m not sure I’m aware of a person or group named, “Personal Finance, Personal Budget and Budget Tool Forums - Mint.com.” So, is Mint.com sending me a birthday reminder? Is it from their forum? Is it from an internal group at Intuit (the owners of Mint.com)?

Let’s ignore the first question, and just assume the email came from Mint.com, the entire company. Now we have to deal with the second question: Why was this email sent? There is no content that I couldn’t have lived without in order to continue to have a good relationship with Mint.com. In fact, there’s a bunch of bad content in the email: First, today is not my birthday. This note came a cool 2 weeks early. Actually, this message is post-marked with a 2009 send date…so it’s 50 weeks late. Second, they called me “joshe.” That’s not even my real name. I just can’t think of a single reason I should receive this message.

So now I’m assuming the email was sent in error. And now that I’m thinking that Mint.com has made an error, I’m left to wonder what kind of other errors they could be making with my personal finance data.

Folks, my message here is simple: be careful with the emails you send out on behalf of your company. Email seems cheap, or even free, but every email you send has a cost to your users. Don’t send out birthday reminders. Don’t send value-less messages that have no calls to action. Oh, and please choose a sent-from name that makes sense to people outside your organization.

Thanks.

The point here is not to make yourself look stupid, rather, it’s to get at a basic understanding of how the world works from another person’s perspective. With regard to the example above, I’ve heard lots of responses to the “What do you mean by ‘fast’?” question. For some people, especially those with a technical background, “fast” means that pages appear quickly when you’re clicking around on a site. For other people it means that you’ve got some problems with your workflow. These people feel silly clicking all over your site to get things done, especially in comparison to those new cool Web 2.0 sites they’ve used.

So if you have a feeling in your gut that you don’t understand where someone is coming from, don’t be afraid to ask a “stupid” question. Get back to basics, it’ll help you see the world through the eyes of another.

Look at each decision you’ve made, and simply ask, ‘Why?’“

Links should be blue, you’ll decide. Next action: Why?

Each time we use the word MagicTouch in a headline, it should be followed by an ® symbol. Next action: Why?

A client will say to you, “I think it will look better if this text is center justified, rather than left aligned.” Next action: Why?

Stopping to ask why? will force you and others to think about the actual intended use of a feature. It will push you to think about user behavior, instead of random decisions. And most of all, it will teach you that you actually believe in what you’ve designed, because you’ll know you’ve thought it through. If at any point you can’t answer the Why? intelligently, you’ll know you have some rethinking and potentially redesigning to do.

This concept should be applied outside the world of design, as well. When you come to a decision, it’s never a bad idea to test it out with a well thought out Why?

In the end, it’s all about finding purpose. In everything, find purpose.

And with that message, I would like to share the news that I have decided to move on from ThoughtWorks. My time here has been tremendous and purposeful, but it is time for me to go try something new. If you read my blog via ThoughtBlogs, I invite you to subscribe to my RSS feed, because it likely won’t be displayed here much longer. Thanks, ThoughtWorks. I’ll miss you.

As I consumed the popular media, I began to think about the more pedestrian views out there. It is important to understand what the everyman thinks, even if one does not agree with him or her (and I certainly do not agree with many of the opinions out there). After all, it is only by understanding others’ points of view that we will ever get ourselves out of these international confrontations. Peace comes when people understand and interact with one another.

A great place to get at peoples’ opinions is the popular new communication tool: Twitter. Twitter allows users to post messages, opinions, and thoughts 140 characters at a time. Each post is a tiny glance at a person’s thought. If you’re not a member yet, you should give Twitter a try. It’s quite fun and addictive.

So, as I set out to glance at what people were saying about the situation in the Middle East via Twitter, I decided to build a tool that would help with this task. And so I did just that, with TwiddleEast.

Here's what TwiddleEast looks like

TwiddleEast allows you to quickly glance at what people on Twitter are saying about a few of the Middle Eastern countries in the news today.

Check it out, and I’d love to hear if it is helpful to you. If there is anything I can do to make TwiddleEast better, don’t hesitate to let me know, and while you’re at it: follow me or TwiddleEast on Twitter.

This afternoon I was convinced that it was time to get out. Time to persevere (against a zero-degree temperature) and try, at least a little, to get something done. So I packed my side bag and headed out to the gym. That’s when I met my hurdle: digging out the car.

I started the activity the way I normally do: by starting up the engine (because if it’s too cold for that to happen, then there’s no point in the rest) and blasting the defroster. I then brushed and scraped the car, and checked the tires to make sure they were in a good position to free themselves. Everything looked fine, and as I waited for my windshield to fully defrost I thought positively about how I would get out of my spot. I pictured the car rocking gently back and forth and then, almost comically, jumping out of its spot and onto the nice, soft, well-plowed street.

The ease of my vision was not to be in real life. I rocked my car plenty, but managed to get myself stuck and re-stuck three times. Yes, that’s right, I said three times. Each time I ran into my apartment building and grabbed the steel-headed shovel, ran back outside and cleared as much ice as I could away from the wheels. And each time I found myself stuck again, only to repeat the whole process.

Finally, in frustration, I decided to give up. This was enough of a workout for the day. Shoveling snow is not as easy as it may sound. You have to realize that that soft snowy powder that you may be picturing eventually turns into big, heavy boulders of ice and hard rocks. (This is why there are many heart attacks during winter…people forget how difficult it is to shovel snow.) As I surveyed where my car lay, I realized I was blocking an alleyway. So not only was I stuck and ready to give up, but I also had to do something to get myself unstuck.

Luckily, a nice man from the next apartment over had seen my struggle and came outside to offer a hand. After a bit of pushing he was unable to free me from the predicament. We talked about strategy for a few minutes, and then another man showed up. “Easy on the gas, real easy,” he said. Another couple of heaves and ten seconds later my car was free.

When I returned home a bit later after a drive to cool my insides down I found a nice parking spot that should be a bit easier to get out of. As I approached my apartment I spotted a car with its wheels spinning. With the driver accelerating, I pushed the car out of its spot. A few minutes later when I ran to my car to pick up the forgotten shovel, I spotted the man I had pushed out helping yet another stranger. As I passed he waved and said thanks, and I relayed my story of just an hour earlier. We laughed it off and shared a, “yup, it’s finally really winter again” moment.

This is what it’s like to live in Chicago. It’s a city that’s tough as it is soft. It’s a place where people push past and look out for each other. A place where we don’t interact much in the winter, but when it’s needed, people are glad to lend a hand.

This is where I live and despite the tough parts, I love when the gentle, helpful side of this city emerges. It’s like no other place I’ve lived.

And all you people are the heroes I’ve known
We’re staring off the edge into the unknown
We are not there yet, but we cannot go home
So we cry and we sing
Yeah I remember everything

How for once in our lives
We saw what we wanted and took a bite.
We picked the fruit from the tree, and it was ripe.
And it was ripe, and it was ripe, and it was ripe.”

- Ben Lee, “Ripe”

If you’re American, get out there and vote today. It’s your civic duty. We’re all counting on you. Thanks.