2×4: An Interview With Brett Terpstra

2×4: One series that examines two topics, creativity and productivity, by asking those who make things on the web the same four questions on both subjects.

There is a day in every Apple geek’s life that leaves a permanent mark; it’s a day we all remember. It’s a moment in time where things change, and get better. Tasks that once seemed complicated become easier. You discover new tools that make your work on and for the web more efficient.

That day is the day you discover Brett Terpstra.

To discover Brett is to want to learn more about what you can make for your Mac. You start going down rabbit holes that you never imagined yourself going down. For the uninitiated, Brett is the developer of Marked, the Senior Dev at AOL, he is a frequent blogger on both his own site and TUAW and as Brett it himself said, “I create elegant solutions to complex problems.” He also creates exceptionally useful tools such as nvALT and helpful resources such as his library of TextExpander tools. Brett is generous with his time and his creations and even though those of us who are not deeply technical will occasionally find ourselves in over our heads, his creations are useful for all levels of geek, including all of us productivity and “lifehack types.

Without any further ado, here’s an inside look at how Brett Terpstra manages to do in a week what many of us would find to be impossible in a lifetime.

Have you always considered yourself a creative person?

Not really, but not for lack of desire.

My younger brother is an amazing artist; even his toddler scribbles were always fridge-worthy. In my single-digit years, I was a bit competitive and constantly assured myself I was just as creative as he was. It wasn’t true, at least not in the fine arts disciplines, but I maintained a shaky confidence for a while.

In a parallel story, my father brought home a PC Jr. when I was six. I started experimenting in Logo and BASIC and solving Kings Quest games. I didn’t realize at the time that these were creative pursuits.

After coming to terms with the fact that drawing and painting were not my fortes, I pursued my technical interests. I built my own PCs, started a BBS and continued programming. I also acquired a used Tascam 4-track, a keyboard and an acoustic guitar and began piling up cassettes full of compositions. Once again, I didn’t really piece together the connection between all of these things.

I went to college at the University of Minnesota for Computer Science, failed Calc 2 and–for some reason– decided to try art school. I went to the Minneapolis College of Art and Design for a BA in Interactive Multimedia. It was there that I finally came to understand that my technical and creative sides were tightly intertwined; I realized I’d been creative all along.

What mediums and inspirations do you gravitate toward to realize your creative goals?

Computers. My peers often espouse starting on paper, but my creative flow is much smoother when I have a keyboard and trackpad in front of me. I brainstorm in digital mind maps, record in DAWs, outline and build solutions in text editors and design in vector and photo-editing applications. I know that more analog mediums are better for some people, but they don’t click for me the way that digital solutions do.

If you had to point to one thing, what specific posts or creations are you most proud of and why?

I think an app I wrote in 2006 called MoodBlast would be my pride and joy. MoodBlast was a way to update 6 of the most popular micro-blogging services simultaneously from a HUD you could pop up with a keyboard shortcut. Everyone’s forgotten about it by now, but it was the attention that it received that made me start thinking that some things that came easily to me were less obvious to others. It may not have been the best work of my life, but it was a turning point in my awareness of my own capabilities (and limitations, but that’s another story).

Any suggestions for those who feel they may not be creative enough to unlock their inner artist?

I think the takeaway from my own story is that you might not be creative in the areas you initially want to be, but by examining the things you are good at (or at least drawn to), you might find that you’re already creative— and exceptional. Embrace those talents and constantly explore and develop them. All creativity comes back to solving a problem, whether it’s putting ideas on paper or canvas, making physical objects do something useful or beautiful or making bits and bytes ease a workflow???.

Can you describe your current personal and professional responsibilities?

I head up the team of developers behind tech blogs including Engadget, The Unofficial Apple Weblog and Joystiq. I work mostly on front-end code and design, and provide a communication bridge between the platform developers and my team. I also develop and support Marked and other Mac applications in my “spare” time.

How do you go about balancing the personal, professional and digital?

I ran my own business for a few years, freelanced for a bit and have worked from home for quite a while now. The one thing I’ve learned is that areas of responsibility need clear time divisions. I won’t say I’m the best at it, or that I always honor the time slots I set for myself, but when there’s no geographic division between home, work and play, I need specific times–and often physical spaces–to keep things separate. Failing to do so typically leads to an imbalance for me. I’m good at quitting my day job around five, but when it comes to the rest of the day I tend to be less precise. I have a very obsessive personality; I’ll stay up all night working on a project that I’ll often discard by morning. That was a waste of time I could (should) have spent with my family (my wife, our two dogs, three cats and a parrot) and a lack of sleep that will affect my productivity for at least the next 24 hours.

Creating obligations is sometimes the only way I enforce those separations. I hate flaking on promises, so making plans to be somewhere with someone is usually the motivation I need to stop what I’m doing and switch modes. Even if it’s just a plan to watch a movie in the living room with my wife, it’s usually enough to force that division.

What tools and techniques do you find yourself counting on to get through your workload?

I use plain text for a lot of what I do, from writing to note-taking to programming. I even use plain text for certain task management purposes (TaskPaper), but I rely on OmniFocus to handle my overall daily todos. My text editor is the tool that gets the most use on any given day. That’s always been TextMate, but I’m really starting to love Sublime Text 2 as well. When writing, I usually use Byword and always work in Markdown.

My own applications are often designed to fill a specific need in my own workflow, so a good portion of my toolset is of my own design. nvALT (a fork of the incredible Notational Velocity) is in constant use and all of my projects rely on notes and lists stored within it. Marked is a major part of my writing workflow. Launchbar and FastScripts, along with a slew of my own AppleScripts and shell scripts, fill in the missing holes. Working without these tools is slow and tedious for me.

As far as techniques go, I’m a fan of the Pomodoro technique. I find it works well with my need for allotted times for specific tasks, and it provides the structure I find important in my time management. A grid to work within. I don’t use it religiously, but whenever I sense the need for it, I pull up a Pomodoro timer (usually on my iPhone).

What is the best starting point for the unproductive amongst us, who are looking to get more organized?

Outlining and planning is important, but it doesn’t really produce anything. I always think it’s going to be the best way to get rolling on a large project, but it’s a “fiddling” stage. I’m not advising against it, just don’t depend on it to help you actually begin accomplishing the work part. The most important step for me is writing the first paragraph, coding that first function, drawing the first lines on a blank page. Then things start to fall into place. For me, outlining and mapping can eventually become an avoidance of actual work.

I’d attribute most of my own productivity to being fortunate enough to get paid for doing what I love, and often having the flexibility to work on what I’m in the mood for at any given moment. That’s a luxury that I don’t think many people have. If you have the option, though, allow yourself to work on what you feel most motivated to accomplish right now. It’s far easier than concentrating on a task while thinking about another project entirely.

Michael Schechter is a Mac geek who rambles about how technology impacts our productivity, our creativity and our lives. You can connect with him over on his blog or as @MSchechter on Twitter.

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2×4: An Interview With Brett Kelly

2×4: One series that examines two topics, creativity and productivity, by asking those who make things on the web the same four questions on both subjects.

We all want to change our circumstances; we want to make more money or get a better job. For most of us, it’s simply a fantasy, something we’ll imagine ourselves doing, something we may even try for, but more likely than not, it’s something that will never happen. Why? We don’t do what it takes to make that happen. Brett Kelly of Bridging The Nerd Gap made that happen when he got his job at Evernote.

Many of us sit around and scheme. We try to find any easy route to improve our circumstances. What most of us don’t do: the work. We don’t do what it takes to get ourselves noticed and get in the door. Brett did. Brett wrote the user guide that was missing, Evernote Essentials. It was downloaded 12,000 times and caught the attention of the team at Evernote so much so that they hired Brett full-time to write and maintain their user documentation. It was a chain of events that enabled Brett’s wife to be a full-time mother, empowered him to work from home and helped them get to a place where Brett was no longer working two jobs (or when he is, it is now in pursuit of his own projects).

Brett’s story is more than a bit of hard work or a spot of good luck; it wasn’t just about writing the right book at the right time. It’s about consistently looking for ways to make things that matter and delivering the goods. Evernote Essentials is a great resource and the site he created to support it, “Bridging The Nerd Gap” is consistently a useful site. Brett is a hell of a writer, especially for those of us who enjoy our Mac geekery. He brings the goods, but he is also grounded in a way that is rare amidst us Apple and GTD fanatics. Look no further than his recent take on minimalist writing apps. Where most of us get excited and exuberant, Brett finds clarity and makes sense.

Without further ado, here’s a look at how Brett Kelly consistently does what it takes to make things happen.

Have you always considered yourself a creative person?

No, not really. Though, when I was growing up, “creative” was a word used to describe poets, musicians and sculptors. I’ve enjoyed writing in some form or another going back to high school, but it wasn’t until many (many) years later that I saw it as a creative pursuit on par with the other, more obviously “artsy” endeavors I mentioned a second ago. Now, I would say that I’m certainly a creative person, but I don’t necessarily think that makes me terribly unique. The lesser-sung outlets for creativity, I think, are things like problem-solving. My six-year-old son isn’t going to be writing sonnets anytime soon, but he can certainly figure out a way to eat the last cookie without technically breaking the rules.

What mediums and inspirations do you gravitate toward to realize your creative goals?

My creative expression can be wrapped up in precisely two gerunds: writing and programming. I can’t paint, draw or play a musical instrument. I deal in words and characters (the kind you access via the Shift key, not the kind you develop as a novelist) because the parameters are fairly well understood and agreed-upon, particularly when talking about software. All the creativity in the world isn’t going to save you if your program doesn’t compile or generates three screenfuls of error messages. You’re working in a known universe. I like it that way. English is arguably quite similar, though there’s definitely more flexibility. When I’m writing, my goal is to say something that the reader can understand. If I fail at that, then it’s time to re-examine the execution a bit and figure out where things went south.

The inspiration part is easy: people who are better craftspeople than I am. Thanks to the Internet, you can hardly swing a dead eCat without hitting somebody who is a hell of a lot better than you at just about everything. Having ready access to the works of my heroes—both writers and programmers—is like looking out toward what I may become one day, if I work hard and take every opportunity to improve.

If you had to point to one thing, what specific posts or creations are you most proud of and why?

I guess I’d have to say my eBook Evernote Essentials is my current front-runner for the achievement of which I’m most proud. This is mostly because it’s far and away the longest single work I’ve ever produced and, well, it’s earned me some money. Plus, lots of people really like it, which helps.

Any suggestions for those who feel they may not be creative enough to unlock their inner artist?

Creativity isn’t about being able to paint or write or make music; it happens every day on a much smaller, less glamorous level. When I discover that I can use a binder clip to hold my iOS charging cable firmly to my desk, that’s creativity applied to problem solving (except people don’t usually use the world “creativity”).

You’re a unique little snowflake of a person that’s walking around having had different experiences than everybody else. These experiences combined with your personality give you a particular take on any number of problems or topics. After all, a butcher’s apprentice is going to be a very different hunting partner than a taxidermy student. Use your specific brain and emotional makeup to take a look at existing situations/problems and see if you don’t have different spin on it (because that’s exactly what creativity is — a different spin on the stuff we all see/feel/use).

Can you describe your current personal and professional responsibilities?

By day, I’m the Technical Communications Manager for a startup called Evernote. The title is a little ambiguous, but my duties include generating user documentation and doing a bit of programming—some things for the web, some internal tools. If you’ve ever used the Evernote Knowledge Base, you’ve probably read words that I’ve written.

Personally, I’m the undeserving husband to my first wife and we have two great kids. I also write a blog called Bridging the Nerd Gap where I talk about all sorts of different things, mostly relating in some way to technology or productivity. I also co-host a weekly podcast with my good buddy Myke Hurley called Cooking with Brett and Myke where he and I talk about anything and everything that happens to tickle our fancy on a given day. Lastly, I’m the one-man show behind my little ebook business where I handle everything from marketing, customer support, product development and—most importantly—the office coffee equipment.

I’ve got other self-imposed responsibilities in the form of unannounced projects and such, but those are the biggies.

How do you go about balancing the personal, professional and digital?

This is one area where I could definitely use some work, but I’ve got a reasonably good handle on things. Every day I eat a quick breakfast with my family before walking down the hall to work (I work at home). I don’t usually take a real lunch break, but having taken a couple of strategic breaks to hug my wife and kids, who are also usually at home, I knock off around dinner time and have dinner with the family, followed by family hang-out time until my kids go to bed a couple hours later. Then, I’ll either spend time writing, reading or working on something. I’ve got far more ideas than I have time to execute on them, though, and that’s hard.

The more tactical parts where I need help involve getting to bed at a reasonable hour and doing a better job “defining my work” (to borrow an expression from David Allen). I’m routinely bitten in the ass by a poorly defined project or task, so I’m trying to make fewer mistakes there and spend less time tuning my task manager (which will lead to knocking more tasks out in the time I’ve got and not crawling into bed at 1:30am).

What tools and techniques do you find yourself counting on to get through your workload?

I’m a big proponent of GTD. We’ve had a rocky relationship in the past, but it’s definitely how I like to roll. The best part about it, I think, is that it makes it possible to move everything forward, even if it’s only a little bit.

As far as tools, you’ll almost always find me in one of these applications: OmniFocus for tasks on my Macs and iOS devices, Evernote for all sorts of different things, Vim for writing code and prose and Apple’s Mail. Without OmniFocus and Evernote, I’d probably be 40 pounds heavier, single and in therapy.

What is the best starting point for the unproductive amongst us, who are looking to get more organized?

I’ve probably bought more copies of David Allen’s Getting Things Done for desperate friends than I care to remember, but that’s what I tell just about everybody to do. Yeah, I know it’s become cliché and lots and lots of people won’t shut up about it, but it’s really such a great antidote for the stressed out everyman (or “everylady”, if that’s a thing).

Tactically, do what David Allen calls a “mental sweep”; essentially, sit down with a big stack of paper and a pen and completely empty your head of every single thing that’s got your attention, one item per sheet. You can read his seminal book for more info on what to do after this, but the point is that your brain is really good at solving problems and creating things, but it positively sucks at holding information such that it can be called back up on command.

If I’m ever feeling overwhelmed, I’ll sit down and do exactly this mental sweep activity until I’ve cleared everything out of my brain and it can relax.

Michael Schechter is a Mac geek who rambles about how technology impacts our productivity, our creativity and our lives. You can connect with him over on his blog or as @MSchechter on Twitter.

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