Smart techniques for personal time management to make the most of your most limited resource.

As a general rule, nobody at Basecamp really knows where anyone else is at any given moment. Are they working? Dunno. Are they taking a break? Dunno. Are they at lunch? Dunno. Are they picking up their kid from school? Dunno. Don’t care.

The vast majority of the time, it just doesn’t matter. What matters is letting people design their own schedule around when they can do their best work.

This is not nearly as hard as it sounds. But it does require a shift in mindset. Away from “I have to call Jeff into a meeting now to get his take on this new feature idea” to “I’ll write up my feature idea for Jeff to check-out whenever he has some free time, and then, maybe, we can have a chat about it live later, if needed”.

If you’re constantly pulling people into things, then yeah, where they are right now matters. But if you prefer to let people consider something fully, and get back to you when when they’re ready, then it doesn’t matter where they are right now. We choose the latter.

Jason Fried

Realtime chat is a disruptive way to have a conversation. Slack is so well designed that it's become the easiest and fastest way to communicate, and therefore it has become the default place to start conversations. Making the easiest way to get someone's attention the most disruptive way to do so is inconsiderate.

“If you think about it, Airbnb is like a giant ship,” he says, holding up the napkin. “And as CEO I’m the captain of the ship. But I really have two jobs: The first job is, I have to worry about everything below the waterline; anything that can sink the ship.” He points to the scribbled line of waves that cuts the boat in half, and below that, two holes with water rushing in.

“Beyond that,” he continues, “I have to focus on two to three areas that I’m deeply passionate about—that aren’t below the waterline but that I focus on because I can add unique value, I’m truly passionate about them, and they can truly transform the company if they go well.” The three areas he’s picked: product, brand, and culture. “I’m pretty hands-on with those three,” he says. “And with the others I really try to empower leaders and get involved only when there are holes below the waterline.”

Leigh Gallagher

There’s been a lot written about the strategic focus of successful entrepreneurs. Eisenhower’s Matrix, Peter Drucker, and others.

I find Brian’s approach refreshing: follow your unique strengths, empower your team, and fix the problems that might sink you. His distinction of patching holes only below the water line is especially meaningful to me as I often pick the wrong problems to get personally invested in.

There are times when the world beneath you seems like a treadmill, and you just can't run fast enough to keep up. For every critical project you complete, three new ones show up. Your call-waiting dings twice during a brief call. The stack of "I need your input" memo's is deeper than you'll ever work through in reasonable time.

And while there are plenty of useful techniques for prioritizing, delegating, and staying effective, there are still moments where no system will work. It is, frankly, an impossible situation.

This has been my life for the last few months. My natural inclination is to raise my energy to keep up as best as I can. To push a bit harder, work longer, be more aggressive, and fight. As a result, my coach dubbed me the "crazy person" in the office. I have become so focused on my goals and aspirations, that I don't realize the side effects on the morale of my team and my family. I have become obsessed with keeping up with the promises on my desk, that I've dropped the ball on the implicit responsibilities that are part of having relationships with other people.

In a moment of clarity over the holidays, when the work came to a stop, I realized that it's best to use these moments to do SOMETHING great, rather than EVERYTHING poorly. I realize that decision comes at a cost of discouraging others, for they are also in the impossible situation and just looking for a little help themselves.

Last week I attended the Fourth Global Forum for Business as an Agent of World Benefit. One of the key topics was the implementation of Appreciative Inquiry, which really challenged the way I think about how I understand the value systems of my coworkers.

At its heart, AI is about the search for the best in people, their organizations, and the strengths-filled, opportunity-rich world around them. AI is not so much a shift in the methods and models of organizational change, but AI is a fundamental shift in the overall perspective taken throughout the entire change process to ‘see’ the wholeness of the human system and to “inquire” into that system’s strengths, possibilities, and successes.

Appreciative Inquiry: Organization Development and the Strengths Revolution. In Practicing Organization Development: A guide to leading change and transformation, William Rothwell, Roland Sullivan, and Jacqueline Stavros

The passing of my grandmother Joyce last week kicked off one of the worst weeks of my life. Her death was instantaneous, but unexpected. She felt no struggle, fear or pain. She just left. For her, a happy moment with her husband turned into an endless emptiness here on earth.

But for me and the rest of my family, our lives went from our daily routine to a tragedy we could barely contain. It didn’t feel so much like driving your car into a wall — even that gives you a few seconds of preparation — but more like waking up in the hospital not knowing what happened to put you there. My family and I aren’t wrestling with what happened in that moment that she died, we’re trying to figure out what happens next.

After a few days of anxious preparations, we had a funeral, buried her, and people went back to their homes to get back into the routine of their home lives.

For me, this idea is highly discomforting. Life isn’t the same anymore, and pretending it is just stresses me out. So, I left town to do some soul searching.

What I’ve Learned Through Reflection

Bear with me a bit, as I’m still processing all of this. It all happened just a few days ago.

I have one realization that keeps coming to mind as I reflect: “routine” doesn’t mean “comfortable.”

My life doesn’t feel routine while I’m living in it minute by minute. While I’m at work there’s an endless stream of growing pains, client challenges, systems to improve, sales obstacles and the like. I’m not working on a monotonous assembly line. Every day is new and challenging. I guess I thought that a routine would set-in once things were well oiled and smooth running. At that point, I believed I could use that newfound freedom to shake things up to get us to the next level.

Having a week to step back and process things, I realize how routine things actually are. Week after week, I help keep things in the current mode. I support people to do better work, but only within the boundaries of what our work currently is. This is routine, and I am a part of the grind.

Routine is the seed that grows complacency, which creates mediocrity. Perhaps I’ve already fallen back to mediocrity, and I didn’t even recognize it. It’s time for me to force a change in myself.

What To Do Next?

Honestly, I’m not sure exactly sure what happens next. I’m still trying to sort that out. But, I know that I’m not the same person I was a week ago. I know I’m less tolerant of perpetuating my routine. As a natural result, I feel some changes coming on:

  • I need to empower my team even more than I have, by encouraging them to solve their own problems so I have more space to expand the business.
  • I need to be even more vigilant with how I use my time. I must learn to say no to things which seem important, if they hold back larger opportunities.
  • Continue to support the tremendous team we have, with even more vigilance than before. Importantly, I need to stop coddling them as much as I do.

The fact that I was able to walk away in an instant, for over a week, and the company continues to thrive is a testament to the amazing people on my team and the company we have created together.

Right now I’m grieving. But when I come back, I'm going to downshift and punch the accelerator.

I'm an organized person. Actually, that's probably a massive understatement. I've obsessed over personal productivity for 15 years, and created systems to organize my rather chaotic life. Living messy is hard for me, and I constantly need to remind myself that often times, its my job to mess things up.

Here's the thing about valuable people. They always have too much to do. It's a simple case of cause and effect. When you are valuable to others, they want and need more of you. This doesn't scale. The more people learn to depend on you, the less able you are to help them.

As CEO, there's nothing more valuable than your time. Your time is your ability to help. It's why we say "thanks for your time" when someone serves you. Time is everything.

And so, to be valuable to many people, in a finite amount of time, things fall apart. It's physics, there's just no getting around it. You can't fit it all in. And so, we create a huge mess.

  • We are late to meetings, and not in the totally excusable 5 min "sorry for the traffic" late. Seriously late.
  • We drop the ball on promises. Things that really matter to real people you care about.
  • We make silly mistakes by taking shortcuts. Personally, I'm guilty of delegating things to my team without good expectations.

You're probably thinking that I'm a crazy person. With some better GTD coaching, better delegating, and great supporting staff this would be much more controllable, right? Surely executing more effectively would give you more time back, right? Not so. I've been deluding myself with this argument most of my career.

Here's the truth. Better productivity systems, organization and staff are critical tools, but they make you more productive. That means you can serve more people with your time, but it only overload your plate even more. You become more like a stunt car driver than a civilian driver. Barreling at high speeds, fast turns, unknown obstacles, and an occasional crash. When you drive fast, no matter how experienced, you make a mess.

Intentional Mess Making

You don't always get the luxury of executing the projects in front of you. Rather, its your job to decide what initiatives need to happen. You are a strategist.

And so, you can really shake things up in your organization. You come up with a new idea and toss it to the team to catch. They aren't always ready. After all, you didn't have time to comprehensively prepare them for this project, did you?

As long as you pick these moments wisely, the team will grow stronger and the company more valuable with each mess they inherit.

So, what do we do?

There are a few things we can do:

  1. Never give up your pursuit of productivity. This is not a reason to stop trying to organize. Remember, these systems do make you more productive.
  2. Hire and work with a great assistant. Delegate the mess. Empower them to find the most important content for you.
  3. Most importantly, surrender to the mess. Don't let it stress you out. Stress will kill you, literally. We need you, so stay calm.

How do you decide if you should trust someone? Do you trust by default, or does someone have to earn your trust? What factors go into that decision?

What if I told you that this way of thinking, that you can consciously decide who to trust, is one of the most damaging aspects of your professional mind?

In the book Thinking Fast and Slow, Daniel Kahneman explains the two mental systems that control our mind:

The subconscious mind is the part of the mind we don't directly control. It takes input in the form of experiences and observations and guides us to survive. Our subconscious doesn't understand language, and manifests itself as feelings.

Conversely, the conscious mind is used for analysis, reasoning language and systematic thinking. It's who you are talking to in your inner dialog.

Furthermore, it's important to understand that the conscious mind can easily influence the subconscious mind, and eventually overpower it.

A pathological liar will eventually believe their own lies. At first they know they are lying. They choose their lies consciously. But overtime, their conscious mind overpowers their subconscious, and the truth is repressed. They believe their own lies, and live their life out of alignment with reality.

The same is true about trust, and I have a dangerous habit that I need to work on. When I sit in front of someone that I subconsciously do not trust, I ask myself why I don't trust them. I deconstruct my history with that person. I look to understand the intentions behind their actions. In my head is a fictional representation of who I want them to be, and I consciously find supporting arguments to defend that position.

This is classic overthinking. My subconscious has a much more honest understanding of that person, but my conscious mind overpowers it. Much like the pathological liar who believes his own lies, I trick myself into trusting someone I shouldn't. The truth is repressed, until reality comes crashing back.

My perception of reality will never be more true than actual reality. To fix this bad habit I must learn to always feed my subconscious truthfully and listen more closely to my gut instinct.

Using the Cynefin framework can help executives sense which context they are in so that they can not only make better decisions but also avoid the problems that arise when their preferred management style causes them to make mistakes.

The Cynefin Framework is a very interesting model for leaders who need to evaluate the effectiveness of their leadership styles in complex situations.

Dave Snowden's Cynefin blog explores many case studies of the framework in action, but I think you'll find the video and link below to be a great place to start.

One of the keys to effective executive productivity is to manage tasks and map them to predefined outcomes. Over ten years of working various productivity systems, I got quite good at handling things that were expected of me and kept my projects moving forward. But about six months ago I had an epiphany that changed all that.

My epiphany was that most of the tasks I track were things that I was asked to do, and only a few were things I thought were valuable. Meaning, I was quite good at helping other people move forward with their agendas but weaker at managing my projects.

To fix this, I needed to think more about the results than the actions. By making a list of the outcomes I am trying to create, it becomes easier to see what todo’s are important to me, and which are not.

To do this, I use an excellent list manager called The Hit List by Karelia Software.

App  Screenshot

Manage Tasks with The Hit List

For the last ten years, I’ve been a notorious task list switcher. I’ve probably used every product available on the Mac/iOS platform. Notably, I used OmniFocus for most of the last eight years.

As a minimalist, I’ve found The Hit List provides the perfect environment to both plan projects as well as accomplish tasks. The killer feature is its smart lists, which are saved queries like iTunes smart playlists. Sounds nerdy, but it’s a powerful concept.

How I Configure The Hit List for Maximum Productivity

I’ve tried a variety of setups, but this one has stuck with me. It’s very basic and feeds my minimalist nature. The objective is to help me plan by thinking about and reviewing my desired results, and then view the tasks in a Stephen Covey Important/Urgent matrix.

There are a few basic guidelines that make the system work. If you follow these guidelines, the software does all the hard work for you.

  • Results are created as tasks at the top of the hierarchy, and tasks are sub-tasks underneath. Results are not actionable in themselves, and so we give them a tag of `result` as a way to filter them out of our actionable lists
  • Tasks given a priority of 1-3 are considered “Important”. You can use the 1-3 value to make some more significant than others.
  • Tasks given a priority of 4 or higher, or no priority at all, are considered “Not Important.”
  • Tasks with a Due Date in the next three days are considered “Urgent.”
  • Tasks with a Due Date more than three days in the future, or no Due Date at all, are considered “Not Urgent.”

How to Configure the Software

Here’s how I setup my projects:

Sidebar Setup

The purple folders are “smart folders.” We won’t be adding items directly to those lists. Rather, the items from our projects will show up here automatically based on how we configure those folders.

Notice that I keep all my projects in the “Projects” folder (collapsed above), organized in lists however you’d like. That structure is entirely up to you.

I keep any future projects I don’t want to worry about in the “On Hold” folder. The actionable lists we are about to create will filter these out of view.

Smart Lists

We’re going to create five smart lists. These smart lists will automatically look into your project lists, and show you items that match the query we create.

  • Outcomes: Shows all of our active tasks which are tagged with `result`. This is a handy way to keep those expected outcomes at the top of your mind.
  • Important and Urgent: This is your “on fire” list. Things which need attention right now, and the outcome is valuable. Generally, you want to avoid letting things show up here, as they cause anxiety and stress.
  • Important, but not Urgent: These are valuable items which aren’t blowing up in your face. If my system is working well, I work from this list almost exclusively.
  • Urgent, but not Important: This is a list of things that are nagging you right now, but add little value to your intended results. Consider delegating or deleting these items.
  • Not Urgent or Important: Get rid of these items. They consume your time and attention.

The Hit List manual has great documentation on how to setup your own smart lists, so I won’t show you how the software itself works. However, I will show you the exact queries I use in my own setup. I’ll explain the first one in detail, and then the others should be obvious.

Note: As of the time of this writing, on the Mac app supports creating smart lists. You can use them on any device once created, but the Mac app itself is required to create them.

Create a Test Project

To make sure you have everything setup correctly, create yourself a “Test Project” which has this content:

Test Project

As we create our smart lists, you can check the results to make sure the correct items are showing up. For each of the Important/Urgent lists, you should see only the single task that matches. In the Outcomes list, you should see the top result task, and it’s sub-tasks.

For example, once you’ve created the “Important and Urgent” smart list, it should have only have 1 item from the test project in it, the task labeled “Urgent and Important”.

Urgent, but not Important

Lets start by creating the “Urgent, but not Important” list, as its one of the more complex.

Create a new Smart list with the name above. Setup the query like this: (Note, you’ll need to use the option key to add the sub-rules)

Urgent Not Important

Here’s how this works:

  1. The first set of rules filters tasks down to just those which are due in the next 3 days, or overdue
  2. The second rule hides anything which is in the “On Hold” folder.
  3. The third rule filters out any tasks which we have tagged as `Result`
  4. The last rules filter to only tasks which are low priority, or don’t have a priority set.

You can follow this direction to create the remaining smart lists using the following settings.

Important and Urgent

Important And Urgent

Important, but not Urgent

Important Not Urgent

Not Urgent or Important

Not Urgent Not Important


Outcomes Setup

Productivity Books in my Library

13 Things Mentally Strong People Don't Do by: Amy Morin
A Year with Peter Drucker by: Joseph A. Maciariello
The Essential Drucker by: Peter F. Drucker
Eat That Frog! by: Brian Tracy

More Productivity Books