Organizational tips from top tech CEOs

Tim Cook (Apple CEO), Jeff Bezos (Amazon CEO), and Jack Dorsey (Twitter founder and CEO) are some of the biggest names in business. It’s likely that their products touch your life every day. With such a tremendous amount of responsibility, how do these titans stay organized and on top of everything they need to do?

Late last year, TIME magazine published a look at how high-profile tech CEOs stay organized. I love articles like this since a peek at such high-level organization and productivity is rare…and often surprisingly simple. The following are my favorite insights from the article.

Jack Dorsey gives each day a theme. Mondays are for management tasks, Tuesdays for focusing on products, and so on. I’ve set aside a day for administration type work, but never thought of giving each weekday a theme and, therefore, a focus.

Meanwhile, Marissa Mayer (president and CEO of Yahoo) looks to the impromptu moments that happen between meetings and scheduled get-togethers to spark meaningful ideas. “Some of the best decisions and insights come from hallway and cafeteria discussions, meeting new people, and impromptu team meetings,” she wrote to her employees in 2013.

Facebook CEO Mark Zuckerberg embraces the power of creating goals for himself. In 2010, for example, he set out to learn Mandarin Chinese. Just four years later, he stunned an audience at China’s Tsinghua University by conducting a 30-minute interview entirely in their native language.

Finally, Wendy Lea, CEO of Get Satisfaction, makes a point to empty her mind and spend time on reflection. “I take 15 minutes every morning for contemplation and to empty my mind. I take a bag full of thoughts I need cleared and each morning I pick one out, read it, and send it down the river near my house.”

I love this one as it seems we spend less and less time in quiet reflection, processing the day’s activities, lessons and challenges. It’s so easy to succumb to the temptation to fill every quiet moment with a smartphone or an app that there’s no time to let your mind work on what needs attention. I’m going to adopt this practice and intentionally make myself stop, reflect, and process each day.

Video game soundtracks for productivity

I’ve found a unlikely source of music to listen to while I’m at work: video games.

The relationship between music and productivity has been demonstrated in several studies. For example, one study has suggested that music increases productivity when workers are engaged in repetitive tasks, while another demonstrated that music has a positive effect on a person’s emotional state and can help with self-motivation.

Tempo and style can affect your productivity, too. If I’m cleaning a room or doing yard work, I want something with a fast tempo, typically rock. It’s easier to feel energized with invigorating music. It’s different when I’m working quietly at my desk, however, and that’s when I listen to video game soundtracks.

When doing quiet work at my desk, I must listen to instrumental music. Lyrics are too distracting because I end up singing along and not getting any work done. Modern video games (not old-school ones like Pac-Man) have lengthy soundtracks and are exactly what I’m looking to listen to. Yes, classical music is also a great choice, but not the only choice. There following are the game soundtracks I love to listen to while doing thoughtful work:

Lost Cities is a card game designed by Reiner Knizia. A version for iPhone and iPad was released a few years ago and it has a fantastic soundtrack (available here from iTunes). It’s like music from a fantasy movie.

Monument Valley is an award-wining game for iPhone and Android. It’s very pretty and so is its soundtrack. I’d describe it as atmospheric and certainly more abstract than that of Lost Cities. This is the album I listen to first thing in the morning with headphones. It really gets me in the mood to work.

Sword and Sworcery is a pixelated beauty of a puzzle game that I quite enjoy. Its soundtrack is just as quirky as the game itself. If bass, drums, and filtered synthesizers are your thing, this is the soundtrack for you. Just like the others, it’s all instrumental to get in the zone and work.

Organize goals with the SELF Journal

There are numerous tools on the market to help you organize your goals, and I’ve recently began to use one that might also interest you: The SELF Journal. This little notebook is something I backed on Kickstarter back in 2015. After receiving my journal in December, I used it to successfully plan and implement a new season of my podcast. The experience was so positive, I’ve decided to share it with you.

Are you setting goals effectively?

The problem with goal setting is that many people do it in a way that doesn’t help them to achieve their goals. Many set unrealistic goals (run a marathon next weekend without any training), underestimate completion time, or fail to review progress.

Another big hiccup is not having a plan. Let’s say you set a goal of organizing the garage, top to bottom. Simply saying, “I’m going to organize the garage this weekend,” isn’t enough and probably won’t work. The SELF Journal, aside from being well-made and attractive, features a built-in system for moving toward a goal effectively, day by day.

The SELF Journal method

When my journal arrived last December, I was ready to dive in. I had a project that needed a lot of time and attention, and the journal seemed like a perfect fit for helping me to achieve it. In a nutshell, the book uses these methods:

  1. You create a 13-week roadmap. Many poorly-crafted goals lack a distinct beginning, middle, and end. The SELF Journal helps you to create this timeline and write it down.
  2. A procrastination-busting calendar. You’re encouraged to fill every working time slot with a relevant activity. No, “just checking Twitter real quick” does not count.
  3. Prioritized planning. You’re meant to plan tomorrow’s tasks today, so you’re clear on what’s to be done in the morning.

There are two more aspects that I really like in the journal. The first is tracking and reflection. The journal provides space for you do reflect on your wins for the day and what you’ve learned. The wins emphasize the last aspect of the system — bookending your day with positive psychology — while the opportunity to record lessons learned informs future work.

The book’s morning routine emphasizes the preparation and work, while the evening routine highlights reflection.

I’ve been quite happy with it and I suspect others will also find it beneficial. Its current price is $31.99.

Eat that frog later?

“Eat a live frog first thing in the morning and nothing worse will happen to you the rest of the day.” — Mark Twain

The “frog” in the Mark Twain quote above has been adopted by the business community and productivity advocates to represent the one task or activity you’re least looking forward to completing over the course of your day. The idea being that once the unappealing task is done, the rest of the day is a breeze in comparison.

It’s an interesting idea for sure. But let’s consider a minor alteration: is there a benefit to eating the frog second, or even third?

In May 2011, the Harvard Business Review published an article entitled, “The Power of Small Wins.” In it, author Teresa Amabile describes something called The Progress Principle:

“Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work. And the more frequently people experience that sense of progress, the more likely they are to be creatively productive in the long run.”

Amabile and her colleagues conducted a study in which they asked people to record details of a “best day” and “worst day” at work, in terms of motivation. The results were interesting. The days labeled as a “best day” were those during which progress was made on a project:

“If a person is motivated and happy at the end of the workday, it’s a good bet that he or she made some progress. If the person drags out of the office disengaged and joyless, a setback is most likely to blame.”

I’ve noticed this tendency in myself. For that reason, I like to set myself up for early wins with one or two quickie successes early in the morning.

For example, if know I have to sit down at the computer and write a proposal, I might clear a few emails from my inbox first, tackle another small to-do item (like returning an object to a coworker), re-read an article related to my proposal, and then begin writing.

I find that if I clear a few easy items off of my “to-do” list, I experience some of the benefits described in the Progress Principle above, and I can use that momentum to tackle the big project of the day — the frog. A couple little successes can go a long way.

Up your keyboard shortcut game with TextExpander

A few years ago on Unclutterer, we made a couple suggestions for increasing your computing productivity with keyboard shortcuts. I’m a huge fan of this practice and suggest everyone spend less time with the mouse and more time learning the keyboard-based equivalents of the tasks you perform most often. But, if you’re really ready to ramp up your keyboard wizardry, look no further than a program called TextExpander ($49.95).

TextExpander is a Mac utility that lets you replace one string of text with another. And do not fret, Windows users, I have not left you users out in the cold. PhraseExpress (starting at $49.95) is fully compatible with TextExpander, and syncs shortcuts between the two.

Also, I shouldn’t have to state this outright, but I’m going to: I pay for this utility myself, it’s what I use, and I’m not being compensated in anyway to write this product recommendation. Phew, now that’s out of the way …

Why would you want to use a utility like TextExpander? The short answer is that it saves you a lot of typing. Let’s say you own a small business and must produce a boilerplate email to customers who write requesting certain information. The response is just three short paragraphs long, but the time spent writing it over and over adds up. TextExpander lets you define a brief string of text, say “.response”. We’ll call that the trigger snippet. When you type .response, it’s immediately replaced with the three-paragraph email.

Or, let’s say you’re a developer who must use the same bits of code over and over. You can create a trigger snippet that’s replaced with the code in question, saving you time and reducing the likelihood of a typing error. As you use TextEpander you begin to realize its magic simplicity.

Today, I use TextExpander to:

  • Replace commonly misspelled words
  • Replace the surnames I often get wrong
  • Add a lengthy URL when I need to
  • Reduce the potential for human error when pasting complex code

TextExpander offers advanced features that make it even more useful. For example, you can opt to have it place your cursor at any point in the replacement text, which is great for those times when just one part will change. You can also turn it on or off in specific programs, so you don’t have to use it.

Struggling with keeping a journal

Two things I constantly fail at are keeping a journal and coffee.

I don’t like coffee. I simply dislike the taste. Oh, I’ll drink a cappa-frappa-pumpkin whatever with whipped cream and more calories than a bacon cheeseburger, but that’s not coffee. That’s a dessert masquerading as coffee. It’s the hot water filtered through ground beans that I just don’t like.

As someone who’s coffee-averse, I often feel like I’m missing out on a major social activity. People enjoy spending time together over a cup of coffee. Every few years I’ll try it again, hoping my tastes have changed, and every year the results are the same: I can’t finish one cup.

I have the same relationship with journaling.

I’ve read many articles and had several conversations with people, colleagues and those who’ve built careers around productivity and personal organization. They all say the same thing: It’s hugely beneficial to keep a journal. They’re not wrong, either.

A Huffington Post article earlier this year outlined 10 benefits of keeping a journal, including:

  1. Promotes progress toward goals
  2. Boosts memory and comprehension
  3. Strengthens one’s self-discipline

Academics agree, too. The University of Rochester Mental Health Center published an article on the practice of journaling and mental health, citing additional benefits. And writing down what you eat in your journal can even help you lose weight (if that’s something you want to do).

I believe in the benefits, yet there’s a disconnect. Each time I try to maintain a journal in earnest, I fizzle out.

Thinking the issue might be the tools, I’ve purchased very nice paper journals and top-rated software. I even got a special pen and designated a time of day for sitting down to record a journal entry. Despite these best efforts, a few things happened.

  1. I couldn’t think of anything worthwhile to say. “Drove the kids to ballet and soccer practice” is boring and, as far as I’m concerned, hardly worth putting in writing.
  2. I felt self-conscious, like a teenager keeping a diary.
  3. I decided to skip it because of either reason number one or two. Then I skipped another day, and another and soon enough I’m failing at journaling.

In many ways, a to-do list and calendar can be similar to a journal. They certainly record what I’m doing and my commitment levels. But it’s not the same. In fact, keeping a journal feels like one more thing cluttering up my to-do list.

Like so many things in life, keeping a journal requires motivation. So, if you maintain a journal, what keeps you motivated? Have any of you struggled to do the same, perhaps for similar reasons? Last, is it simply that journaling is not for me, and I should move on?

Perhaps we can discuss it over coffee.

A clean-slate office

Having recently started a new job, I’ve come into a real treat: a brand new workspace. A complete blank slate. It’s a rarity and a treat.

My first thought, of course, was to populate it with the tech and tools that I’ll need to get my work done. I started making a list when it dawned on me to stop, throw the list away and take an altogether different approach. Let experience dictate what I add. It’s been quite an eye-opening experience.

I started with the bare minimum: pens, some index cards, and a calendar. Big items like a computer and printer were supplied by my employer. Everything else I’ve added only when I’ve needed something.

First, I realized I needed my smartphone and a charging cable for it. Rather than schlep a charging cable back and forth every day between my home and office, I bought a cable to live at my desk. Next, once I knew for certain that wearing headphones was acceptable when working, I added a set of earbuds go my supplies. Nothing says, “Can’t talk, I’m working,” like a pair of headphones. Plus, I’m more productive and happy when listening to music.

(More on keeping wired earbuds under control.)

Next, I added software I wanted as I needed it. Unfortunately, there are strict policies on getting software approved for a corporate computer, so this process wasn’t instantaneous. Eventually, I received approval to to get all of the software I depend on, and they’re all browser-based cloud services. Namely:

Not only can I get to work with my preferred tools, all of my documents, preferences, etc. are in place.

It’s nice to start new and not have any software or equipment cluttering up my work. Instead of assuming I’ll need something, waiting until I actually need it has kept things to an appreciated minimum.

Of course, you don’t have to accept a new job to approach your office or workspace with a clean slate. Take a week or two and notice what you use and what you don’t. Write down what you need but don’t have, and finally observe what you have but never use. Then make adjustments. You just might end up with a tidier, more efficient and more productive work space.

Defining technology and increasing your productivity

Recently, my 10-year-old son reminded me that technology doesn’t have to be a collection of wires and software, but can be the simplest of devices and still wonderfully productive.

His teacher asked him to write about his favorite subject. He chose science, and broke his writing project into a few aspects of scientific study, including technology, which he defined as “a tool to help you do things better.”

“Well,” I thought, “that’s right.”

Years ago, when I worked as an IT director and had many computers — and computer users — it was quite the task to keep all my work and equipment all organized. It was around that time I discovered David Seah, a designer who often writes about his efforts to become more productive online. He makes lots of cool paper-based productivity tools, including the delightful Task Order Up sheets, which I used religiously. (And Erin loves the sticky version of his Emergent Task Planner, too.)

They were inspired by the order tickets you might see in a deli or restaurant where short-order cooks whip up pancakes, chowder, and slabs of meatloaf on a regular basis. Each sheet represents a single project, with fields for the project’s title and all of the actions that must be completed before the project can me marked as “done.”

There are also fields for marking down the amount of time you’ve spent on a given project, time spent on each action step, and the date. Best of all, they look like the tickets from a deli counter, so you can line them up at your desk and then pull then down as each “order” is completed. Dave even recommends using an order check rail for added authenticity.

Of course you can just use index cards if you like, but I believe that the tools we use can be useful, attractive AND fun. Technology really is any tool that helps you do things better.

Turn your brain off and get to sleep

Unclutterer reader Jade recently wrote to us describing her biggest organizing challenge:

But my biggest issue is getting to bed earlier. I know sleep is important, and when I get enough I am amazingly productive. The problem is getting enough. Not easy to go to bed early when you are a natural night owl waking up at 5 am for work … No, I’m not getting a new job, I love it too much to do that. But the sleep deprivation is killing me.

I get home and I’m too exhausted to do anything, until bedtime, and then by brain won’t shut off!

Meanwhile, Lynn shared a similar concern:

Also I’m also a night owl and don’t get enough sleep which causes me to feel tired and not want to tidy up.

Here’s a problem with having a brain in your skull: human minds are like motors. A motor that loves to run and run and resists shutting down. My wife and I have both dealt with this problem of our minds wanting to go, go, go. We’re in bed, trying to fall asleep, but the motor keeps running and trying to process the week’s school activities, bills, work, and so on. It can be very aggravating.

My first piece of advice is to build some wind-down time into your evening. I’m a night owl (it’s 9:00 p.m. as I type this) and as such I feel productive and energetic after the sun sets. I know this means if I don’t take steps to help me get to sleep, I’ll be up until at least 11:00 p.m., if not later. Knowing my personality, I start my wind-down routine around 9:30 or 10:00 p.m. I’ll read a bit or do another task that requires little thought. This gives me time to slow down.

I also have a nighttime routine. I started this after remembering back when my kids were babies. We got them ready for bed the same way every night: bath, stories, bed. This gave them time to wind down and the process itself helped their bodies and minds shift into sleep mode. I do the same with myself and it works: get changed, brush teeth, find clothes for the morning, and read by my little reading lamp. Same thing, every night if possible.

A few years ago I adopted a productivity routine that had a nice side effect of helping me get to sleep. Namely, before I leave my desk at the end of the day, I write down the things I must accomplish the next day. I like the organization, and my brain likes knowing that these important things have been parked where I’ll see them in the morning.

Lastly, here’s a trick I learned while studying as a college student: your bed isn’t the place for work. When I was in the dorm, space was at a premium and I’d often end up doing homework on my bed. That wasn’t a good idea, as I started to associate that area with work, when the bed is for sleep. Sit on the couch with your laptop, not your bed, if you want to be comfortable.

One final note: If this becomes a persistent problem, talk to your doctor or perhaps a specialist in behavioral sleep medicine. The above advice is obviously for the common human motor of a brain.

Struggles with GTD and possible solutions

Unclutterer reader MrsMack recently wrote to us describing her biggest organizing challenge:

My … struggle is with the GTD method. I’ve read the book and I think it could work really well for me, but the required cleared-schedule, back-to-back two days to get started is so intimidating and too overwhelming. I don’t have the liberty to turn my life off for two days to work without interruption. How can I ease into this?

I first discovered David Allen’s book Getting Things Done: The Art of Stress-Free Productivity when I was an IT Director at a residential school. That was a crazy job, as I was supporting about 80 computers, a network and more, including heading up the help desk for there school’s 100 employees. It was easy to feel overwhelmed and I often did. Fortunately, I discovered David Allen’s method.

Adopting it in earnest took a lot of work, not just in my own behavior but in the materials I was using. I felt it was worth the effort, but I also realized how much effort was involved. Processing everything in my work life to get “clean and clear” took days. Personally, I recommend taking time off and completing the work as he suggests. I found it saved me time and frustration over the longterm. However, I know this isn’t realistic for everyone.

If you genuinely don’t have two days to dedicate to this process, the following are the alternatives I suggest:

Pick the area that’s most in need of attention and focus on it for as long as you can (two hours? four?). You might have enough time to get your desk/work area and your work projects “clean and clear.” Then simply “GTD” (if I may use it as a verb) that aspect of your life. This will reduce the overwhelmed feeling and get you comfortable with the system, so that when you’re ready to tackle the next area, like that pesky garage, you’ll be an experienced machine.

I do believe in David Allen’s method, especially in the very real feeling of being on top of everything that comes from getting “clean and clear.” I also realize that GTD is not the best fit for everyone. With that in mind, here are several alternative methods you might find interesting or appealing.

Leo Babauta’s Zen to Done system. Leo created his Zen method specifically to address what he sees as “…the five problems many people have with GTD,” namely:

  1. GTD is a big change of habits
  2. GTD doesn’t focus enough on doing
  3. GTD is too unstructured for many people
  4. GTD tries to do too much
  5. GTD doesn’t focus enough on goals

If any of those five issues are ones you’re having with GTD, maybe Zen to Done is an alternative that could work for you.

Another program is Asian Efficiency’s Agile Results. I’m not super familiar with this method, but it’s been popping up on my radar off and on for a while now. Like Leo’s Zen to Done, Agile Results is more goal-focused than process focused.

While working on this article, I reached out to my buddy Mike Vardy of the website Productivityist. His “theming” method is quite compelling. To begin, look at what he calls the certainties in your week. For example, on Sunday, there will be no interruptions and the family will be home. On Monday through Friday, the kids are away, and on Saturday, the family is home. With those certainties identified, he creates themes based on the results:

Sunday: No interruptions, family-home
Monday: Administrative Work
Tuesday: Kids at daycare, wife at work
Wednesday: Daddy Duty
Thursday: Meetings/Offsite Work
Friday: Kids at daycare, wife home
Saturday: No interruptions, family-home

The final step is to “lock down,” as Mike puts it, the remaining days. His final themed schedule looks like this:

Sunday: Creative Day (Writing)
Monday: Administrative Work
Tuesday: Creative Day (Writing/Recording)
Wednesday: Daddy Duty
Thursday: Meetings/Offsite Work
Friday: Creative Day (Writing/Recording)
Saturday: Family Day

It’s clever, and a part of a larger method of his Now Year formula. His alternate method might work for you.

Getting on top of everything can be a chore, but it’s well worth the effort irrespective of what method you ultimately decide to adopt.

Using batch processing for your professional social media accounts

Years ago, I learned a lesson from ProBlogger that has helped me effectively and efficiently use Twitter for my work. The lesson is part productivity, part organization, and perfect for Unclutterer: working in batches.

Way back in 2008, blogger Darren Rowse wrote about the benefits of organizing your outstanding tasks into similar batches, and then addressing each batch individually:

In my understanding of the term ‘batch processing’ it was always used to describe systems (usually computerized ones) where data was collected together for a period of time before it was processed. Instead of doing every small ‘job’ as it arrived jobs were ‘queued’ or collected until the computer was ready to process them all at once. This meant that the computer could do these ‘batches’ of jobs all at once when it would otherwise be idle.

Darren started to batch outstanding tasks — writing, processing email, social bookmarking and so on — and found that getting these done in a burst of energy freed up time for other, more taxing activities later. Today, I use that advice to great effect while tweeting for Apple World Today.

I’m in charge of the Twitter account at Apple World Today (among other things). To provide an interesting experience for our followers, I’ve created a list of daily themed tweets, as well as a schedule for when they’ll be published. Over the weekend, I sit down and write what will be our tweets for the week. Getting this done ahead of time frees me up to concentrate on the myriad other things I have to do and, I’ll be honest, it feels so good knowing this task is done.

The following is the theme schedule I follow:

  • Monday: Funny stuff to start the week off right. Amusing photos, videos, etc.
  • Tuesday: Behind the scenes. A look at what my colleagues and I are working on, like articles in progress.
  • Wednesday: Informative or surprising tweets. Quickie how-to tweets or tips that are 140 characters long, or little tips that people can use right away. People love these, and they take the most thought from me.
  • Thursday: Retweet interesting content from followers and share relevant industry news.
  • Friday: A look at our work culture. Unlike on Wednesdays, Friday posts focus on my colleagues and I as people. You’ll see us with our dogs (or cats), at the cafe and so on.

Even if you don’t tweet as part of your job, batch processing tasks can be an extremely effective way to organize your tasks. However, those of us with “Twitter” on our job descriptions will certainly benefit from devising a formal schedule and “batching” time to sit and write the week’s tweets. You’ll get time to formally sit and consider how you’re using social media, you’ll free up time for other tasks during the week, and you can practice your organizing skills, too. As Michael Scott would say, that’s a win/win/win situation.

Sleep and productivity

Yesterday, Jacki Hollywood Brown’s article explored the relationship between music and productivity. Today, I want to continue with another productivity booster, which has been called the “third pillar of health,” sleep.

The relationship between sleep and productivity seems obvious: adequate sleep means you’ll have enough energy and focus for the coming day. While that’s true, there is much more to it than that.

A 1999 study discussed at 2013’s Corporate Sleep Health Summit demonstrates that a lack of sleep can affect not only productivity, but innovation. After losing just one night’s sleep, subjects experienced “…particular impairment to tasks requiring flexible thinking and the updating of plans in the light of new information.” While most people don’t regularly lose an entire night’s sleep, consider that many driven business people and entrepreneurs wear their four and five hours of sleep like a badge of honor.

Meanwhile, a BBC study suggests that deep sleep “makes room” in your brain for the next day. “One of the main things the brain is doing [during deep sleep] is moving memories from short-term storage into long-term storage,” the study claims, “allowing us more short-term memory space for the next day. If you don’t get adequate deep sleep then these memories will be lost.” Ever forget some crucial information for that big meeting? An extra hour of sleep could be the remedy.

Now that I’ve described just some of the benefits of a restful night’s sleep, I want to point out some technology that will help you hit the hay.

Sleepy Fan ($1.99, iPhone). When I was a kid, I spent summer nights falling asleep to the sound of a large box fan, not unlike this one. I fell in love with is steady hum, and today I use the Sleepy Fan app in its place. It offers three fan types to choose from, and even lets you adjust the sound itself.

The FitBit has a feature that lets you track your sleep. When paired with a smartphone app, it lets you view data on your previous night’s rest, including restful moments and when you were fidgeting.

The Philips Wake-up Light is a nice alternative for those who dislike being jarred awake by a screeching alarm. Over a period of 30 minutes, the Wake-up Light gradually brightens itself from dark to a custom illumination level (up to 250 lux) and provides pleasant audio.

You can get a good night’s sleep, listen to music appropriate to your task at hand, and enjoy a satisfyingly productive day.