Trip Boss Evolution – from Palm to iPhone, a behind-the-scenes look at the design process

Recently we released phase 1 of Trip Boss travel manager for iPhone. We've been working towards its release since the AppStore opened 2-1/2 years ago in 2008. Although we released other iOS apps prior to Trip Boss, with each app we learned something new that we could use in Trip Boss. Full time focus on Trip Boss took about 7 months and we expect another 3-4 months to release the remaining phases, or “modules”. In comparison, Trip Boss for the PalmOS, the initial release, took over a year to write. Some of the subsequent additions and enhancements (such as itinerary) took another year each to release. This post will show you some of the history behind Trip Boss' design and some of the insight behind the design decisions for the iOS release.

Trip Boss main screenshot

Conceiving Trip Boss

Trip Boss was conceived from a family travel log that my family used when we were kids. In a wire-bound, lined notebook, we kept track of mileage, expenses, kept a journal, recorded and rated where we stayed and what we visited. My mom used the old logs for vacation planning each year. We did a lot of repeat road trips from Michigan to Seattle, as we had family in Seattle. The books were a great tool for keeping track of things, reflecting on the fun we had, and for planning new trips. The concept was ideal to take to the electronic level.

Brief Development History

Trip Boss was first released on the PalmOS platform in November 2004 for the Tungsten PDA and Treo smartphones. We had low res, black and white graphics, but high functionality. We quickly released an update that included hi res color graphics (the beginning of the “eye candy era”). We took the log book concept and added many features so it could be also used for business purposes. The original release did not include a fully featured itinerary nor a packing list, but these major features were released in 2.0 and 3.0 respectively. We also added our first wireless data access in 3.0 via our mobile travel website, Version 4.0 is our re-creation of Trip Boss for the the iOS platform and was released November 2010. The first edition for iPhone includes expenses and budget. The stand-alone tip and currency calculators are also part of this initial package. Subsequent modules will be released as add-ons via modest in-app purchase.

Trip Boss low-res (B&W and color) graphics on a Palm PDA:

Trip Boss first release screenshot   Trip Boss color release screenshot

Trip Boss hi res graphics on a Palm Treo:

Trip Boss 3.0 expenses screenshot   Trip Boss 3.0 itinerary screenshot

The Background Graphics

The Palm version had many hardware limitations—from file sizes, to performance issues, to color palette, to resolution constraints. When you download the iPhone version of Trip Boss, the most obvious change is the graphics. Gone is the plain white background. In its place we've crafted various stunning travel-related images. Nearly all of photos were crafted in-house, cropped and processed to provide a subtle, yet pleasing background image. While only a small number were selected for the final product, over 300 images were processed so we could find just the right images for the app. We hope to add more in upcoming releases and modules, as long as performance isn't compromised and file size constraints can be met.

The Tables

Our goal was to create a familiar iPhone interface—the table views—yet give them a bit of flair. The end result is transparent rows, edges subtly rounded, to give a glassy effect. We used alternating rows of grey and blue, to help the user visually differentiate row data. We used grouped tables in the data entry areas to keep similar data together; the goal was to not overwhelm the user with the quantity of data collection that was possible. We wanted to make sure the user could easily find the entry point for the data he wished to log, but also not be limited by only a few fields. The end result is a clear interface for entry, plus an easily understandable view for data display, while maintaining an elegant look and feel.

Trip Boss 4.0 expenses on an iPhone4:

Trip Boss Expenses screenshot

The Travel Icons

In addition to the text descriptions, we wanted to create a pleasing set of recognizable travel icons, from a bed for lodging, to an airplane for air travel, to binoculars for sightseeing, to a pretzel to indicate a snack. Each of the 50+ icons have been hand-drawn in both retina and 3G resolutions. Keen attention to detail has been paid, from visible salt on the pretzel, to shadows and reflections on the shuttle van, to the postmark on the postage stamp. Each row begins with an icon, for visual recognition of the data.

lodging icon  pretzel icon  shuttle icon  postage icon


Throughout Trip Boss, we added in little feature enhancements. One feature people have clamored for is the ability to view the status of the submitted expense reports across trips. After deliberation, we decided to do this graphically with traffic-light colored orbs. On the expense summary screen, users can view all status at a glance. Status can be changed from within the Trip Details, or via a shortcut by tapping on the orb itself.

expense status screenshot

The budget status view mirrors the expense status, but with its own graphic. Because Trip Boss is both a business an a personal travel log, we created two graphics, selected in the settings. We have a piggy bank that empties as the budget is spent (and he also starts to frown) and we have a wallet that slowly empties of its bills. Both the expense and budget status screens can be viewed by selecting “Expenses” or “Budgets” from the Trip Boss home screen.

piggybank  wallet

Another area where we paid a lot of attention to design and detail was in the tip calculator. The tip calculator is designed to look like an actual printed carbon receipt, sitting on a restaurant tablecloth. Our goal was to leave nothing standard in the app--even the keypad has been styled according to the overall Trip Boss theme. All these little "surprises" are included throughout, to make the experience more enjoyable for the user.

tip calculator screenshot

Data Entry

Data entry on a mobile device is both crucial and cumbersome. Expenses are incurred while mobile, but time is short for detailed entry. The goal of Trip Boss was to allow for quick entry, when in a hurry, but also allow for ample details, which can optionally be added later. The latest technology provides for plenty of opportunity for data entry improvement. In this version of Trip Boss, we have a “Get Location” feature, so you do not have to enter the address manually. The date/time is automatically recorded when an expense is entered. Real-time currency rates are updated wirelessly, so expenses can be accurately converted into the home currency (yet reported “raw” as needed for expense reporting). In addition, Trip Boss has a “photo receipt” feature. Just take a quick photo of your receipt to either enter the data later, or submit the receipts with your expense report.

In addition to all the technology, each main expense category has been customized for logical data fields. For example, for fuel expenses, users can enter gallons (or liters & UK gal—everything is international), price/gal, or total cost and the remaining fields are calculated. For lodging, the number of nights and occupants can be recorded. The meal entry is accomplished via a built-in tip & split calculator (also available for use separately, outside an expense entry). Each main category can be further defined with sub-types. Enter as much or as little data as you wish; enter as convenient.

Just the beginning

The expenses and budget module of Trip Boss is the cornerstone, but it's just the beginning. We plan to release greatly-expanded individual modules to cover all the travel functions of its Palm OS predecessor. These modules will be released for a modest in-app purchase from within the current release. This way, each module will be able to talk to the rest of the modules. Users can choose only the modules they want or need. Our goal is for the Trip Boss application to be a complete set of travel management tools for your mobile iOS device.

We hope this post has provided you insight on how Trip Boss has been conceived and designed behind-the-scenes. You can find additional screenshots and descriptions on our website or view and purchase Trip Boss from the iTunes AppStore.

Reviews and ratings are also very much appreciated. We love feedback, so please feel free to contact us for help, or with your feature suggestions and comments.

UPDATE: Trip Boss now comes in four flavors: Trip Boss Expense & Budget travel manager, Trip Boss Itinerary manager, A Journal for Trip Boss, and Trip Boss travel manager, Itinerary, Expense & Budget. Pick one app to start, then add each module via in-app purchase to customize to your travel needs.