Designing like an engineer is bad for business
Making great software is a huge challenge.
The challenge only gets harder for those that have to wear multiple hats because of constraints, self-imposed or otherwise.
As most readers of the blog know I act as the main designer and developer for Cashboard (shameless plug #10384). This situation arose from many factors, but the main one being I wanted to get the product up and running under my own power. I’ve seen too many projects fail and I didn’t want anyone to blame on this one but myself.
I tell most people I’m a designer first, but I program out of necessity. Anyone in the software engineering field knows this is usually a bad idea and results in a shit product, yet I believe I’m able to pull it off because I’m able to "switch modes" or "switch hats" most of the time.
I’m damn good at what I do, but I’m definitely not above the classic problem. I routinely have to catch myself "designing like an engineer" instead of designing as a user experience person. Case in point, Cashboard’s "Account Preferences" screen.
The old screen is shown below in all of it’s fucked up, cluttered, and confusing failure.
This particular screen was built over time. Sections were added as the product grew, and it shows.
The design made complete sense to the programmer side of my brain. Sections of the screen directly map to functions of the code. As it usually turns out in situations like this, it was the exact wrong way to approach the design of that screen.
Non-relevant information is shown which clutters the view and detracts from the goal at hand. Things aren’t logically grouped from a customer’s point of view, and worst yet the screen has an overall busy look that’s quite perplexing.
There are two forms on the page, with two buttons, and a link to update other relevant information on yet another screen. (yuck!)
Preferences Screen Remix
Finally fed up with the design I took it upon myself to give that screen a makeover. Putting on my designer hat I busted out the design documents necessary, re-assessed the goals of customers visiting that screen, and had a revelation.
Customers of the app visiting this screen just want to update their preferences. They don’t care that changing their currency is a different operation from setting their date formats or billing address on the back-end, and they shouldn’t have to.
As with most design breakthroughs, this one was sitting right in front of my face. The solution was plainly there, yet I was missing it up until now because I wasn’t paying attention.
The updated design eliminates unnecessary information presented from the first screen, brings the "billing address" fields into the mix, and consolidates the multiple forms into one.
The result is a much cleaner looking form that actually makes sense for the goals at hand and is pleasing to look at as well.
As someone once told me – it doesn’t cost a thing to pay attention, but not paying attention can cost you dearly. True words indeed.
Cashboard logo exploration
Here’s a group of logos I came up with during the recent Cashboard rebranding.
The final, accepted logos are at the top left. Losers were rejected for a variety of reasons, but I thought some people might enjoy seeing the thought process that goes into an effort like that.

Cashboard gets new-new branding
Sometimes I just can’t leave things alone. I refreshed the Cashboard brand a few weeks ago in preparation for an event I needed to attend. The results were OK, but nothing I was overjoyed with.
I’ve since taken the time to really update the brand. I believe the new look reflects the quality of service that we’re providing with Cashboard.

That, and I just love looking better than the competition…
Paralysis by analysis
During my life as a user experience consultant I was brought on board multiple times to help redesign major enterprise software applications.
Most of the time companies bringing me on had never worked with a user experience professional and definitely didn’t know what to expect. All of them just "wanted the app to look better" or "be more user friendly". I can’t blame them. The majority of people in the user experience field don’t even know what to call themselves, let alone have a single definition of what they do. How could I expect people not in the field to know what they were getting? I quickly learned that educating the client was the largest part of any redesign effort.
I’d get in and take some time to understand the application. I’d do background work using personas and scenarios just like Alan Cooper taught me. I’d draw prototype sketches on enough paper to kill an entire tree. I’d get real and build HTML prototypes. All while my client was wondering when the pretty colors and graphics were going to be brought to the table.
...Then I’d recommend they change the entire damn thing from the ground up.
A variation of this scenario would always play itself out. Product managers would most often try to whittle down my ideas, taking selective parts they liked and sweep the major changes that were scary under the rug. Sound familiar to anyone out there?
History repeats itself
It’s a funny thing, being both the client and the consultant these days. I’m going through a design project on Cashboard that requires massive sweeping changes. Massive, scary changes just like the ones I used to propose to my clients. The type of changes that engineers would riot over because they required too much effort.
About 10% of the way through I found myself caught in a rut. I was facing numerous failing unit tests. I found myself not working on the project for a day or two at a time. I was second guessing my design decisions, even though I knew they were sound and necessary.
I was being paralyzed by fear.
The fear of breaking things. The fear of an overwhelming load of work that I saw no end to. The fear I saw in my client’s eyes back when I was a consultant.
It’s times like this that you must rededicate yourself to the effort in order to get it done. Nothing grows without painful change. Being a web app, Cashboard has the luxury of constant improvement. If I don’t nail an initial release I can always refine what I have as I go along. I can push new releases live every day – even if some customers get pissed in the meantime. This has been my motto from day 1 and it’s worked out great for myself, and others.
How does one rededicate themselves to such an effort?
For me, it’s the driving desire to put all of my competitors out of business. It’s the status report of how many paying customers I have today versus yesterday. It’s how much my monthly revenue has grown from $0 only a year ago to a level that can sustain my lifestyle comfortably. It’s the validation of my intelligence, drive, and hustle by being able to show off what I’ve done.
Being a self-motivated, self-run entrepreneur is a hard business and not for the faint of heart. But it can be done. I’m living proof.
Time to blast Pantera and smash out some coding. Until next time.
Where's my clone army?
I have a confession to make. I built Cashboard by myself.
Thats right. One person. Me.
Sure I’ve hired out small bits and pieces along the way. I’ve had wonderful contributions from trusted advisors and I’ve gleaned knowledge from trusted friends.
But all the blood, sweat, tears, design, code, and support emails? All mine.
I know some of you might be shocked to hear this. Especially when I throw the term "we" around so often.
I never saw this as misleading as Cashboard is the sum of its parts. The sum of ideas, concepts, advice, partnerships, and work from multiple people – even if it was myself who executed all of this to make it happen. I often take on the persona of my corporation because I think in that manner.
I’m blessed to have developed into an "exceptional generalist" who can do multiple things competently. Design, user experience, programming, SQL, marketing. I’m good at all of the above. I’m a one man wrecking crew. It might sound a bit self centered…who cares? It’s the truth.
I average perhaps 10 to 12 hours daily working on Cashboard…for the past year and a half. It’s worked extremely well…until now.
Cashboard is at a stage in its growth where I constantly need more time.
I can only drink so much hyphy juice or rockstar cans to power me before my heart explodes. There just aren’t enough hours in the day to do what I want.
I’ve come to a realization. I need a clone… (Fuck that) I need a clone army.
Finding the right people
Since cloning humans is frowned upon and we don’t have the technology for replicants yet I’m in a tough spot. I’ve quickly moved past my clone dreams to realize I need co-conspirators. It’s scary and exciting at the same time.
I’ve worked in all of the classic good and bad computer company situations. I was the 17 year old working at Hewlett Packard who lost his job because he stayed out late painting graffiti every night. I also was the 19 year old interviewing CS grads from Berkeley at a "dot com". That 25 year old user experience consultant who designed a brilliant product to see it die because of poor management? I’m all of those guys. I’ve seen the million ways to FAIL.
Up until a few months ago I would have told those war stories with a sad face.
I realize now that all of that just has prepared me for this latest chapter in my software life, and I’m pumped.
I’m not looking to instantly add a ton of people and make a bad choice. I have the luxury of time for now. There’s a few people I have in mind who I’ll be approaching when that time comes. Still, if you’re a technology fanatic, code Ruby on Rails like a bat out of hell, and have a drive as strong as mine I’d love to hear what you have to say.
Bulking up
Google lead me to a great article by Dharmesh Shah on the subject of finding a co-conspirator. It’s written for people exactly in my position. All it did was whet my appetite for more information.
Whenever I’m at a crossroads tackling a new challenge I always do the same thing. Grab a ton of books and immerse myself in the subject.

This should hold me for a week or so.
Watch out suckers, I’m coming for your customers.
Cashboard sponsors Rails Rumble 2008
We love Ruby on Rails at Subimage LLC. We know a lot of our customers love Rails as well, so we’re proud to announce that we’re sponsoring Rails Rumble 2008 by giving away free year-long Cashboard accounts to the winners.
The competition in their own words
Spend the weekend of October 18th and 19th with us, designing, developing, and deploying the micro application you’ve been dreaming about. And in case the launch isn’t enough reward in and of itself, our kind event sponsors have offered up a bunch of really kick ass prizes that the community will help award to the best new web properties.
Crack open those source code editors and get hacking people!
New Cashboard branding
Here’s a promotional business card I made for Cashboard a day ago.
It’s part of a larger rebranding effort which includes a site and application design refresh.
I love designing with letterforms.
Wish I had more time to design and could spend less time coding.
OS X Leopard and Cashboard, sitting in a tree
In the spirit of feeling (and being) productive, I’ve started tracking all the development hours I spend working on Cashboard. Up until now I’ve skipped it, estimating how long I spend working on it every month. It’s interesting to see exactly how much time it takes to get things accomplished, and keeps me motivated on those days I don’t feel like working. I also finally took the plunge and upgraded my development machine to Mac OS 10.5.4 yesterday. One of the great things in Leopard I’m enjoying so far is the web clip capability. It allows you to select any part of a web page, and use it as a desktop widget.
I’ve created a web clip widget to display all of my hours from inside Cashboard. It’s positioned right next to my Cashboard time tracking widget. Now I know how long I’ve worked, and I can keep tabs on how many more hours I need to put in for the rest of the day. Interesting feedback loop, if nothing else.
Updated Cashboard feature tour
Just spent the better part of the last two days working on this update to the Cashboard feature tour.
The old tour was long in the tooth, and did a horrible job of communicating why Cashboard is better than the myriad of invoicing software apps out there.
I’d imagine this new tour will spike registrations, and spark a renewed interest in the program.
Time will tell…



