That Old Time Software

Not long ago I downloaded a new productivity application that recently emerged from a prolonged beta period. Finally, the 1.0 version had arrived, and I was eager to get my hands on it, play around with its features and see what it had to offer. But, for the life of me, I couldn’t figure out how to use it.

To be fair, this application, which shall remain nameless, had clearly been designed with great attention to detail. Its interface is not unattractive and its fit and finish is commendable; you wouldn’t be remiss in regarding it as a completely professional product.

However. I kept staring at it, and kept clicking on interface widgets and pushing buttons, but the more I explored, the less likely it seemed that I would ever really master it. I’m sure that its workflow makes sense, that with some investment in time, a user could realize some significant benefits from it. I just had a hard time thinking that one of those users would be me.

Too Much Is Not Enough

Ultimately I decided it was just too intricate a program for me to bother mastering. I have no wish to denigrate the many hours of dedicated, quality labor invested in its design and development by talented, well-meaning people, but I think I’m getting too old to learn anything more complex than the level of, say, ToDoist.

I no longer find the kind of satisfaction that I used to in laying the groundwork for better productivity, in acquiring complex tools and spending copious amounts of time learning them and setting them up in preparation for the productivity gains they promise to yield for me. I just want to get stuff done with simple, reliable tools and methods that are easily comprehended straight out of the box, and then go about my business. (So, no thank you to the tremendous waste of time that is GTD.)

But it’s not just me. I also think that we’re at a stage now where software interfaces just have to be more immediately intuitive than ever before, have to tell a story with extreme compactness and on first pass. There’s still a long way to go in raising the bar for good interfaces, but it’s much higher now even than where it sat at the end of the last century. In the intervening years, there have been too many good interfaces — still not enough in general, but enough to show us that software design can accomplish much more with much less.

End of an Era

And I guess that’s what left me so cold about that application I tried; it had all the trimmings of a modern Mac OS X or Windows Vista application, but its level of pointless complexity was so clearly from another, earlier era. The sheer number of controls available, and its apparently steep learning curve recalled for me a time when software purchases were planned and researched weeks ahead of time, and software itself was physically shipped in boxes with copious user manuals, and mastered over time with significant dedication and instruction.

Contrast that with how we’re experiencing much of the newer software being released at version 1.0 today: downloaded in an instant, installed at one’s leisure, flight tested and evaluated sometimes within just a few minutes before being carelessly discarded. Or, even more ruthlessly, oftentimes clicked to and experienced entirely within a browser; Web applications have tremendously abridged the opportunity window for all new software, whether it resides on the desktop or the network.

Much of this is not news to many readers, I’m sure. But sometimes, in the midst of change, it’s easy to overlook the fact that we’ve moved from one era to another. Maybe two years ago it would still have been passable to ship an application like that. Today, it’s puzzlingly anachronistic. In a few more years, it’ll just be completely unacceptable. Get ready.



  1. Great historical context, but todo lists can be accomplished with a plain text file. What do you think about software that is extremely powerful, say CAD or video editing software? Does all software need to cater to first use?

  2. Until video editing (or CAD) becomes as familiar as a text file specialist software will still offer enough of a benefit to justify the learning.

    These days people are starting to realise new productivity software will not necessarily help their workflow.

  3. I really like what you wrote here. I know what you mean, too.

    I think, too, part of what makes over-complicated software so unnecessary/intolerable is that there are way more options now than there once were. If one application or interface isn’t intuitive, I will go look for a better one before I decide to invest in learning a system that doesn’t make sense from the beginning.

    Thanks for writing your blog. I am a regular reader and really enjoy it.

  4. I understand this sentiment particularly regarding productivity software. It seems self defeating if it’s so time consuming to save time. I’ve tried several of these apps and found Omnifocus to fall into this trap. Things does not and I find this app good for my style of task management.

  5. I completely agree, Khoi, both in terms of interface and productivity. On the former, I wonder if we’re all spoiled by the ‘giant-text-box-and-label’ interface of so many web 2.0-era apps. I look at Windows programs (especially specialized statistics programs from college) I used to use and shudder. Command line? Fuggedaboutit.

    On GTD, I wish I could get into it. It seems like a really neat cult. But I’m okay with the ‘Write Sh*t Down’ system that Smallist posted about last year. That’s about the length of my attention spa

    Oh! New Facebook wall post!

  6. @Kris

    Not only is Things not 1.0 yet, it also doesn’t fit any part of Khoi’s description above (at least in my opinion). I have some guesses as to which app Khoi is referring to, and if I’m guessing correctly, I completely agree with what he’s saying.

  7. You’ve nailed it, Khoi. I think it’s somewhat unfortunate for people with very complex product ideas that would merit a paradigm shift before users can take advantage. But for a 1.0 version software needs to be obvious.

    I think this is why desktop apps aren’t overall doing too well–the barrier of adoption (and, heck, just having to install something) doesn’t appeal to people when other apps just take minutes.

    On the other hand, I don’t know that this trend really helps people. The more intuitive a tool, the more people use it the way they always have…which often isn’t the most timely. Watch a dozen people use, say, Microsoft Word and you’ll see a world of difference in their performance…and that’s because the least intuitive ways to use it are often the most productive ones.

    That is, if everyone would RTFM they’d be better off. If tools had shortcuts and pushed the envelope then people would be better off, even with the learning curve. But for version 1.0 we just don’t want that, for better or worse.

  8. This post hits home on so many levels. None that I can really share with you all, but I very much appreciate this post. ‘Too Much is Not Enough’ is on point.

  9. I wholeheartedly agree. There is no time to learn a completely new way of working with an application, unless you absolutely have to.

    In fact, that’s why I love Things so much, and couldn’t work with the other big to-do application.

  10. Right on Khoi, this has been a growing frustration of mine over the last few years as well. As addicted as I admittedly am to the exploration of new software, what wins me over is little or no learning curve, every time. It’s why I’ve continually tried and failed to become a follower of GTD, given it up, and returned to writing to-do lists with a pencil in my Moleskine; why I use Textmate to write outlines instead of OmniOutliner, and so on.

    It’s difficult for companiesat least as far as they are concerned to restrict their software’s feature list rather than extend it. People will rarely, if ever, complain about anything being *too* easy to use, and ‘undercomplicating’ is an important step toward creating software that’s immediately welcoming.

  11. Great job, Khoi – right on point. And people should pay attention to your focus on todo lists… a good todo list is just as important as an email program these days, and most people don’t know which one to choose.

    This is why I wrote an entire chapter on todo lists in my book and created a tool that is (imho) just what you ask for: easy and simple enough for anyone to use immediately yet with the depth to endure as one’s todo list for years:

  12. I use a productivity app that recently reached 1.0 and is kinda complicated in a GTD way, and I really love it. Especially now that it syncs with my iPhone. I guess I like structure and rules, and I figured out how to make it match my style. I especially like the recurring tasks, which can be keyed from either the start date or the completed date. The ability to save views, so I can ask it for a list of everything I finished at work last week for example. It also lets me keep my work and home life neatly divided. It does some stuff I don’t need but maybe there is somebody somewhere who loves that part.

  13. I’d make one nuanced point here; it’s about more than simplicity and ‘doing more with less.’ There’s no reason why software can’t grow/enhance/augment its interface as a user becomes more sophisticated. Many users may happily remain in a simple, functional world, while others may wish to extend it to new stuff — Firefox + plugins is not a perfect example, but it’s one model for starting with a baseline and growing over time.

    That’s all to say: It’s about learning — in the Stewart Brand sense of the word. As with architecture, it’s nice to build a structure that meets a specific need at a specific point in time, but it’s even better to ensure that this structure can adapt to the evolving needs of its inhabitants over time.

    To Khoi’s point, whatever you do with your building, you want to make sure that as many people as possible like what they see when they first walk in the door.

  14. Has anyone else used Remember The Milk?

    I love this web app for to-do lists (and it works offline thanks to Google gears – Yes!!).

    It’s easy enough to start using right on the first pass — just login and start making lists.

    But, for those who want it (like me), you can then start adding in a range of very flexible tools (prioritizing, dating, tagging, smart lists…) to personalize it — IF YOU WANT.

    I have no connection to the company, but having suffered through so many unhelpful and overly complex tools, I feel motivated to praise the ones I like!

  15. I have given up trying new software, it’s too often a huge time-suck. It’s not surprising to read Koi’s ‘why bother’ reaction. Think about all the great new web apps and software that gets released week after week on an unsuspecting public. Usually with a limited (if any) design and user testing budget.

    OK actually for productivity I just use Google Docs. Nice and simple. Kinda old school meets new school.

  16. I use it, I bought both the desktop and the phone versions.

    I think a perfectly good software company, actually an excellent one, was ill advised, I think consultants led them down a particular path and they lost sight of something.

    I use it daily. I get better at it each week, understanding it I mean. But I’ll never love it. I thought I might love Things but I couldn’t be arsed learning another one.

    I kinda love TaskPaper which requires no learning. it’s perfect for just straight lists and you can add multiple tags to items so they can cross projects and contexts, But I need the sync… so I stick with that particular product.

  17. Oh, and snarky posts aside, I do agree with your post. I used to endlessly try to make sure all my gadgets were synched and would agonize over what task-management software really rode the pony. Alas, I have gone back to my stone-age ways and use a handy paper planner.

    Something that would be amusing is to compile a list of visual cues that make app/website hopelessly old-school. Like the blue, underlined links and flash intro screens that take ten minutes to load. It’s kinda the feeling you get when someone quite elderly calls the internet the internets.

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