Category Archives: Bad Experiences

Sustainable file system hygiene

“Does anyone have good tips/tricks for file structures? I keep losing track of my projects.”

I hear this question or a variation of it frequently. Just got asked today during a skill share session I was in with the other OpenNews Fellows so I thought I’d write this up.

It is very easy to generate data (whatever form that data comes in — photos, project files, databases, notes, etc) so data accumulates rapidly. No matter how systematic you are about putting it somewhere, your context will change or the volume of data will exceed your ability to keep it under control.

It’s a challenge for everyone whatever their occupation or workflow so how do we deal with it? Here’s my solution:

  • Projects
  • References
  • Archives

Let me elaborate.

First, what problem are you solving? The central question is not “How do I keep stuff organized?” it is “How do I find this later?”, so your goal is findability above all else.

Rule #1: Everything needs a place. If you don’t have a place for things to go, they will go wherever and you won’t find it later.

Second, your data deluge problem is cross-platform and ubiquitous so you need to solve the issue for that scope, not just for one platform or device. It’s not just how you nest and name folders on your laptop but also how you organize things on Dropbox, Google Drive and so on.

Rule #2: The system is inherent to YOU, not the place where things are, it just gets mirrored there. It needs to be abstract and simple so it can be applied wherever you go and wherever your things might be. Over and over again.

Third, we are talking digital things so presume a file system will be involved and acknowledge that a file system is a constrained hierarchy which forces a certain set of decisions to be made.

(Yes, you can always search, great, but you also want to know where stuff lives so you can put more stuff like it along with it. Also don’t minimize your natural desire to want to browse because you will want to do that too.)

Rule #3: It’s a file system and hierarchy is inherently insufficient because categories evolve in meaning over time. Deal with it.

Your system is going to evolve over time so more important than what is the system, is how are you going to respond to the change over time. I have 5 active projects now but what will happen when two of the projects end? What and when do I back things up? And so on. Also:

Rule #4: Hygiene is about maintaining a healthy state. Only you can tell if the state of things is not healthy or going downhill. It’s also up to you to put the time to get things back to shape before it falls into a complete state of disarray.

Ok, back to the solution:

  • Projects
  • References
  • Archives

This is no surprise to anyone who has practiced Getting Things Done, but even if you haven’t, this is a sufficiently good place to start. Why does this work?

  1. Too much nesting is bad (for your own recall and because some backup reasons – some systems really choke with 8+ levels)
  2. Too much scanning is bad (for your own speed/efficiency, long list of projects you are not really working on won’t help you find things quickly)
  3. Trash/distractions are bad (also for your own speed/efficiency), but random stuff will accumulate. You don’t necessarily get to put things where they belong as you are working with them, but you have to at some point.


Whatever you are actively working on. Be descriptive. One folder per project. Anything that involves more than a step that has a supporting set of data/files needs to live in there.

“But I have 100 projects!” That’s not an organization problem, that’s a lack of priority problem. “But I don’t like mixing personal and professional!” ok, create those two folders and then put your projects in them – but remember, the more nesting/complexity, less likely to stay functioning and healthy.

Usage frequency: You will use what’s in this daily or every few days until you are done with the project.


This is a library; things you need to consult on a regular basis or review periodically. They don’t need to be cluttering your projects but need to be accessible and readily available. I have a copy of all my important IDs and docs in folder here. Also all my purchased fonts live here.

For example, when I finish a professional project, I move it to a folder in references called /Portfolio. I know that when it comes time to update my resume, LinkedIn profile or website, I can review this folder for the history of what I’ve worked on since the last update.

Usage frequency: Occasional or on recurring basis in service of active projects.


I put all my backups on the archive folder of my home computer. I back up my various devices to that location as well. Periodically I check my computer’s download folder and move any software to a /software downloads folder in there should I ever need a previous version of an app. I put all my photos here. I have albums I publish to places and such, but every photo taken is put away here.

Usage frequency: Rarely if ever. This only exists for an eventuality but also helps you get rid of stuff from Projects and References that is not that important to your day to day but you don’t want to get rid of.

Over time when I check that References/Portfolio/ folder I find projects that I have no interest in ever talking about again so I move them to archive. If I ever needed to read my graduation thesis ever again, this is where I can go get it (Chances: 0.000001%).

Rule #0: A sustainable file system hygiene depends as much on your workflow maintaining the system as the organization of the files themselves.

(It’s last to make a point, but really, it’s the first rule in importance and impact)

If you focus on organizing, you can go down a rabbit hole of eternal taxonomization that will not stand the test of time because when you are trying to find a thing your focus is on the thing itself.

The file system really should reflects your workflow. Your workflow needs to include a) put things in one of those places b) put the right things in the right places c) move things between those places as the context changes and they evolve/change status d) give all the orphans a home when you come across them (and if there isn’t one, the trash is where it needs to go).

If you do this across all your various systems you will find that findability improves but you also become ruthless about what’s occupying your attention and as long as you use the same pattern over and over, and periodically restore the pattern when it starts to deteriorate, you can stay on top of things.


Yesterday I presented at the DMI Seattle conference and I bombed. As Scott wisely points out: “Everyone is polite and tells [speakers] they were great, even when they bombed.” You know when you bomb. [edit] In truth, it was not horrible, but it was not great either. I haven’t received any feedback so it is also hard to tell. My point is, if you feel it didn’t go well, no amount of reassurance will convince you otherwise. [/edit]

I was meant to give a talk sharing my story growing the UXD practice at Comcast for the past many years. I was excited to do this because I felt it could be useful to new managers and because it would help me be diligent about reflecting on that journey, which I wanted to do but had had difficulty committing to. Also, the timing was perfect. So what went wrong?

Bad choices all around

Things that contributed to the failed presentation:

* I was sick and feeling quite ill. 
I contracted a powerful stomach bug from something iffy I ate the night before. Cold sweats and trembling do not inspire confidence in your audience. I had also been on a panel the prior day and had already set an expectation with the audience on what my delivery style and energy level were. I could not live up to my normal. 

* I was intensely tired.
Because I was actively fighting the stomach bug all night long, I was unable to sleep and felt like my brain was in a haze. I was prepared and know the topic deeply, but I had a really difficult time recalling the order in which I had decided to expose the material and which specific points I wanted to make. The cues in my notes triggered nothing. It felt like having memory hiccups. Also, when I am excessively tired, English, my second language, doesn’t flow as well from my lips and I unknowingly omit words mid-sentence. I can’t hear it as it happens, but I know that must have happened.

* I took on unnecessary technical risks.
I prepared my presentation using OpenOffice and on my Dell Mini laptop. It was great for preparing but proved a poor choice when the projector refused to recognize my computer and the presentation would not display appropriately on PowerPoint on the computer I borrowed. All this happened 30 minutes before the presentation. I should not have experimented with non-standard technology since the visual aid was important, but not testing in advance in the final delivery space and setup is, always, a huge mistake (and I know better). Also, I did not have a plan B. Unnecessary anxiety piled on at the worst of times.

* I didn’t synthesize the story well.
This presentation did help me reflect on this journey as I wanted. I was able to gain perspective on the story in a way I had not seen it before. Unfortunately, I diverged too widely in analysis and ended up with less time to synthesize what I found into a cohesive story. I was sufficiently happy with where things were and it would still have been ok if the above factors had not added up, but they did, so the outcome was mediocre when contrasted with what I knew could have been done. Had I worked more on reducing it further to its essence, I could have managed the other issues better.

* Timing was disrupted.
Never allow external arbitrary inputs to break your planned delivery rhythm. Editing and being more concise in language on the fly are very doable, but only when you are feeling very comfortable in the flow of the presentation. I wasn’t comfortable, obviously, so when I was asked to wrap it up, I couldn’t figure out how and conclusion was completely derailed, which made the story seem like it did not have a real end.

I can’t have a do-over, so I’m going to re-craft this presentation and look for opportunities to give this talk elsewhere to see if I can tell the story I actually wanted to tell.

The point of no return

Things I am good at:

  • Framing problems of all kinds
  • Making sense of complex and unstable situations & circumstances
  • Seeing the potential in other people and helping them succeed
  • Things I am bad at:

  • Expressing my emotions and feelings
  • Distinguishing what I want to do versus what I think should do
  • Allowing people to be my friends
  • I am not good at expressing my feelings. Oddly, I am good at reading other people’s feelings. It’s hard to reconcile how the two are possible in the same person, but I have years of data (aka experience and stories) to prove this. I have been particularly excellent at applying this professionally and have found the ability to distinguish subtle emotions key to solving problems and helping people.

    For a long time I subscribed to the very limiting (and limited) perspective that emotions and feelings made people less adept to do what they needed to do. Almost every situation or problem I have encountered in my life I have tried to reduce to a logical problem. By framing something as a problem, you immediately set yourself up for success because problems have solutions. However, I have come to learn that not all things are solvable. More importantly, not all things require a solution. I only learned this when I came to realize how unsuccessful I had been at solving my own “problems”.

    When you learn something significant about yourself you have four choices:

    1. Deny it
    2. Ignore it
    3. Sublimate it
    4. Address it.

    I am great at doing #2 and quite excellent at #3. I don’t know why that’s how I respond to things but at least I’ve come to accept that is true since learning it. I am able to do #1, but I have a strong desire to learn about the world and myself so it doesn’t happen as frequently. The reality is that only #4 is a healthy viable option.

    The past three years have been particularly difficult for me because I decided I wanted to figure out why I am bad at the items I listed above and chose option #4 as the path to understanding what I found. I don’t recall being more frustrated, dissatisfied, helpless and exhausted in my life.

    In situations where objective problem-solving was the focus, I always perceived the expression of emotions and feelings as a weakness. It is much easier to solve a “problem” when you can discard what is “fuzzy” and that is precisely what emotions and feelings are. We may even have a shared understanding of what some of them mean, but because these things are by nature felt, the way I see it will never be the same as how you see it.

    About two years ago I found myself incredibly frustrated due to my inability to address the things I set out to address. At the time I did not realize it was, for the most part, because they were all feelings and emotions. I also was surprised to find that most of the things that seemed hard in this category were all things about myself. Everything that was about the world and other people seemed incredibly easy in comparison to how hard it was to solve the “problems” in my internal dialogue. When you are bad at expressing feelings and emotions, you lack the right level of appreciation for the types of issues you are trying to solve within yourself.

    Language is key. If you can’t express what something is, you can’t truly think about it. I literally had to start from scratch. What is anger? What is contentment? What is frustration? What is joy? I still suck at describing, even though I am better at spotting it. I will be eternally in debt to my wife who has always been incredibly patient with me in my awkward attempts to express my own emotions and figure out how to deal with these sort of things. It’s much easier to fight than to admit fault, to spin in frustration instead of making progress, to struggle and point at the wrong things as the source of issues than it is to get perspective and introspective enough to understand them fully.

    Being aware of who you are and what you do is a really hard thing. I think a lot of people take that for granted. I certainly felt that way and in choosing to address it have only found further frustration. But I believe in the long-term benefits I can rip from this. It certainly is a leap of faith.

    The point of no return is the point beyond which someone, or some group of people, must continue on their current course of action, either because turning back is physically impossible, or because to do so would be prohibitively expensive or dangerous. It is also used when the distance or effort required to get back would be greater than the remainder of the journey or task as yet undertaken. Wikipedia

    Allowing yourself to just experience a feeling or emotion and let it take it as far as it will take you is hard. That’s what made me think of the expression “point of no return”. If you allow it to just happen, you’ll come out the other side with something. It will never be the same because you can’t get back to where you were before, but you’ve learned and you are better for it.

    I decided to write this up today because I’m feeling angry. I’ve come to learn that this is not something that happens very frequently, and when it does I am really bad at realizing that’s the case. In order to experience it I figured writing about it would let me make the feeling last. I was right. I am angry at a bunch of different things. And the urge to respond to this feeling with some “solution” is overpowering. However, there is one important lesson I have learned in these past few years: If you are able to acknowledge the feeling or emotion, sit with it. Feel it. That’s the only way to learn how not to ignore and sublimate it. Also: no judgment. There is no good or bad feeling, there are just feelings. If you make a judgment call you can’t learn from it.

    I have about a hundred things I should be doing right now, but I’d lose a lot if I didn’t allow myself to feel the anger I am feeling. It’s a new emotion to my repertoire. Before I can learn what to do with it, I need to learn what it is. Clearly today my lesson is that anger is a constructive feeling because I sat down and allowed myself the introspection.


    This is a project I am really excited about and would like all my friends to check out. It’s called Holllaback and it is going to end street harassment. If you never thought about what street harassment means in the grand scheme of things, watch the video. Violence and discrimination start small, but have a big impact. Hollaback!

    Please donate today and help us make this happen.

    Your choice of words matters

    Yet another reason why designers and business folk talk past each other: people who are purposefully misleading to get attention.

    I came to this presentation from Google on their Quality Score measure because someone referred to it by saying “Quality Score is a measure of user experience”. It obviously peaked my interest because it is precisely the qualitative characteristic of user experience that makes it hard to measure.

    When you get to slide 4 you realize that Google knows better and defines Quality Score as “an automated measure of how relevant each of your keywords is to your ad text and to a user’s search query.”

    It has nothing to do with measuring users’ experiences with anything whatsoever. I realize it sounds naive to be cranky about attention-grabbing people but it baffles me that people do this: misuse the notion of user experience to mean anything at all that they want. It is such a coward move. Be bold, say what you want to say!

    More than that, I worry that people just have no clue what they are talking about. Because it that is the case, it is even more worrisome. If people engaged at this level of discussion (i.e.: what measures to use) don’t understand a basic thing such as what user experience means (at its most basic what PEOPLE experience when they INTERACT with something), then we’re all very far from being able to have progress in advancing the conversation about measuring success in the context of user experience.