The "Oh Crap" Moment: How do you know how much you know?

I've generally found that the best solution to a problem is also the simplest. If the complexity of your solution starts to grow more than linearly as you work on it, if it starts to look like the only way to finish it is through brute-force labour, then I've found that backtracking to right before things start to get complicated usually yields an "aha!" moment. A simple, elegant solution will be easier to implement and maintain, more fun and satisfying to work on, and will most likely even solve the problem better.

You don't always have that luxury, of course - some problems don't necessarily have a simple solution. But for me, when things get complicated I take it as a sign that I've taken a wrong turn somewhere.

I'm not sure if this actually answers your question. ;)

That is generally along the lines of what happens when working on my own stuff . The real "Oh crap" moments come when I'm trying to figure out what someone else did.

The great news is that this same mental complexity trap will trip up 99% of your competition. If you can avoid it you have a significant advantage. Look to the grand master: Steve Jobs. Who else would have had the balls to make a beautiful little music player that did almost nothing but play music? The Microsoft Zune is what most people will do when they start off to make a music player and realize how much they could do.

The most difficult part about a simple solution is having the confidence to see it through. The ability to not feel ashamed or embarrassed when people ask "Why doesn't it have X?".

Inspiration from Steve Jobs, on what is essentially The WiFi Question:

NEWSWEEK: Microsoft has announced its new iPod competitor, Zune. It says that this device is all about building communities. Are you worried?

STEVE JOBS: In a word, no. I've seen the demonstrations on the Internet about how you can find another person using a Zune and give them a song they can play three times. It takes forever. By the time you've gone through all that, the girl's got up and left! You're much better off to take one of your earbuds out and put it in her ear. Then you're connected with about two feet of headphone cable.

More great stuff in this article: http://www.msnbc.msn.com/id/15262121/site/newsweek/

Mp3 players didnt have a lot of features when the iPod was launched, and I don't think a portable harddrive solution was particularly simple (engineering wise) at the time. The iPod won because it was portable and had a large capacity, mp3 players for many years were either one or the other even after the iPod shot to fame.

The other players didn't have a lot of features, but they had more, and they sure weren't simple. They had crappy playlist systems, lots of buttons, confusing interfaces, etc. When I said the iPod was simple I meant for the users, not the creators. It was surely a lot of hard work to create the iPod, but end result was a very simple product.

I look at the portability and large capacity as just two requirements for making the iPod simple. A product that "just works". Not holding enough music or fitting in your pocket is a usability problem that detracts from its simplicity.

The iPod had a 1.8" hard drive when all the competitive MP3 players had a 2.5" hard drive, making them twice as large. People seem to forget how much smaller the iPod was compared to all the other hard drive MP3 players, I think this is the real reason it won.

Yep thats what I'm saying. It wasn't interface or brand, at least not until later. For a very long time I don't think there was a single other player with the capacity of the iPod at a comparable size.

I've gotten completely lost following the competition who has been trying to solve the same problem. I've realized their take and solutions will be different from mine. What I do now is write down every day the problem in one simple sentence .. e.g. "I hate traveling and every wifi is password protected!" I keep working the solution, knowing it will grow in complexity because i have to deconstruct it in order to work toward simplifying it. I then create a solution using a three step function for myself and other users. This has been helping me, especially when I get overwhelmed in thinking about more features and functions.

Yes, I get these too. Pretty much every time I talk to someone who takes an interest in my startup, they raise some issue that I either hadn't thought of at all or hadn't thought about in the same way. That doesn't even cover the hacking-related 'oh crap' moments, but most of mine have been conceptual so far. It's to be expected: there are tens of startups in my space, I assume that some are technically better and many are worse.

As you point out, the hardest thing may not be the 'oh crap' moment but rather what conclusions you should draw from it, if any. In most cases I have elected to go simpler when in doubt. Other times I've decided to re-think various aspects of my project, but these are in the minority.

You've just stumbled onto the reason that big companies take some many more people and so much more time than startups to solve a given problem - they don't (and can't) allow themselves to ignore the extra information and its complicated byproducts. Nevertheless these cos invariably started out small by solving one significant problem in a great way while overlooking all those other dimensions. In short, try to evaluate whether the extra information is truly a significant part of the core problem you set out to solve. If it isn't, postpone the solution. If you succeed based on your core solution you can worry about it later, when you'll have plenty of time and money to do so.

Yes, I've noticed the same thing. My current idea is similar to several other start-ups. At times it seems like some companies could be competitors if only they changed their product offering a bit.

I think this is where the business/marketing side of the founders needs to kick in and be determined to differentiate and be better than what's out there.

It's all about providing value for a customer. You either need to provide a better value or have different customers. IMHO, a simpler version can be both good and bad.

Good, if you can start getting revenue and grow faster. Bad if it doesn't generate much revenue but slows you down with customer support and alerts your better funded competitors to your existence and plans.

I think you are dealing with analysis paralysis. I think you should develop an internal weighting system on extra information. remember nothing beats the information gleaned from your own experience. I cant remember where but I read somewhere that the plan is unimportant but the planning is invaluable. Dont keep a plan just keep on planning and implementing. Each new Oh Crap moment is just another input to the ever changing and improving planning implementing process. IMHO.

Maybe including names for the axes will made a better graph I guess Katty Sierra is happy when people use her style.

This may be a nice Creating Passionate Users post. ;)

better?

http://joshwand.com/files/ohcrap2.png

Yeah! Much better!

I'm a fan of Katty Sierra and always read her creating passionate users blog. It's so bad that she isn't posting anymore.

"I wonder if sometimes it's worth ignoring the extra information entirely, and solving a simpler version of the problem instead?"

Yes. Always.