Preparing Yourself for the Organization of the Future

I recently wrote an article about some of the organizational structures of the future and I thought a good follow-up might focus on what you can do to prepare yourself for this upcoming reality. If the organizations of the future (and many of them now) are going to rely on self-organization, holacracy, and other (non)structures that result in high autonomy then what is the optimal employee of the future going to look like?

To thrive in this kind of environment it’s going to take deliberate effort.

Let’s get even more specific:

1. Get comfy with the idea that you aren’t always going to have a clear idea of what the future looks like.

The world moves quickly. Companies form and dissolve. Teams coalesce and break apart as needed. What you did last week is unlikely to be exactly what you'll be doing this week. In a bygone era stability was a key characteristic of a good job. Now, not so much. The only thing that's going to be stable is (hopefully) your ability to deal with instability. Let go of your carefully laid career plans and cultivate the ability to see opportunities for development and advancement because they are likely to emerge when you least expect it.

2. Which means you’ll have to get good at defining your work on a regular basis.

The key task of the knowledge worker is figuring out what the actual work is to be done. You can't just show up to work and expect a pile of widgets waiting to be cranked. For you and everyone else working in the knowledge economy the first task is to figure out what your "widgets" are today and what "cranking" even looks like. Merlin Mann once described email as a place you go to help you figure out who you're supposed to be today. Until you get good at clearly cutting through the vast tsunami of information hitting you at all times it'll be hard to figure out what you're even supposed to be doing to get your job done, let alone doing your job to an exemplary level.

3. Train yourself to shut out distractions even when your environment isn’t conducive to focusing.

Open offices are all the rage and I don't see them disappearing any time soon. That kind of arrangement can be great for team coordination but it also makes it much harder to shut out the world and truly focus on what needs to get done. I firmly believe the ability to focus is slowly being eradicated from our society -- meaning those who do develop their ability to focus are going to become a rarer and thus more valuable asset to any team they are part of. Start a mindfulness practice, start practicing single-tasking while working, do whatever you need to do to master your mind in all environments, but particularly distracting ones.

4. Relish the opportunity to do difficult things because it’s the only way to become indispensable.

The way to become indispensable is to do things a.) nobody else can do, and b.) nobody else wants to do. To do the things nobody else can do you have to be better at something (ideally something important) than most of the other people in your organization. For that to happen, you need to develop your skills and abilities. That happens by consistently seeking opportunities that push you slightly outside your comfort zone. A truly stress-free work life is also a growth-free work life. In a world where the employer/employee contract is more like a short term alignment of interests and not the 40+ years of dedication of yesteryear it behooves you to make sure your skills and abilities are on a constant upward trajectory.

5. Learn how to take care of yourself outside of work because the lines between work and vacation, the workday and the weekend, “on” and “off” will become blurrier.

This problem already exists and like the rise of open offices I don't see it changing any time soon. Obviously, expectations around making yourself available outside of normal business hours varies by organization. However, in even the most progressive companies many people fall to an internal desire to never truly relax and to always keep one foot in the office. This is a recipe for burnout. You have to be at the top of your game every day to not be left behind by the rapid changes your industry, company, and team are facing. True rejuvenation and recovery (mental and physical) are up to you to do well.

The organizational structures of the future value autonomy but with autonomy comes great responsibility. When external structure is removed by the organization the onus is on you to create your own internal structures that allow you to thrive. What's that going to look like?

Photo by Peyri Herrera

The List #18

This special weekday edition of The List is brought to you by relaxation, rejuvenation, the letter R, and the complete lack of will to do anything remotely looking like work over the weekend.

Why You Should be Paid For Commitment, Not Hours or Results - 99U

This strikes me as terrible. Am I wrong? I'm much more interested in being compensated for what I can do and what I produce -- not how committed I am to an organization. Yuck.

The Cult of Busy - Medium

Busy busy busy busy.

I've made it a personal point to not respond with the word "busy" when people ask me how I'm doing. It's a cop out answer and it shuts down a conversation.

Why We're Building All Tomorrows - Medium

I've done a little bit of consulting with this company and they are working on some great stuff. They just released an app called Emojiary which is a nice mix of quirky emoji-based journal writing and experience sampling method/Quantified Self personal development. You should definitely check it out.

How to Build More Flow into Your Work Day - Entheos

This is my second entheos class and this time it's all about how to tweak the way you work and think to help you experience greater flow during your work day.

Photo by honbliss

Workologism #4: Write Emails Outside of Your Email Client

Email is a junction where information comes in and information goes out. It is not a café where you just hang out all day and see what happens.

I'll often keep a list of the emails I need to write in my task management system so I can open a text editor and just crank out my responses without having to look at what's already in my inbox or what might come in while I'm writing. When I'm done drafting all the emails in my text editor I'll open up my email client and copy/paste the messages over and send them on their way.

Photo by Ryan Blanding

The Key to Self-Leadership: Don't Break Promises

You can probably think of a leader who inspired you in some way. For many it's a great boss, a teacher, or maybe a coach. In the world of work, working for a great leader can make a potentially boring or thankless job into something more meaningful (and a bad leader can take something that should be awesome and just absolutely ruin it).

As an independent worker, there are fewer ways for good (or bad) leadership to impact your work life. Obviously you don't have a boss, supervisor, or some kind of inspiring CEO to give meaning to your work. Instead, leadership of you falls into your own lap. You are simultaneously a leader and a follower and at that point, you have to ask yourself, "Do I find myself an inspiring leader? Am I a leader that I should/would follow?"

I've been thinking a lot about questions like this because I've recently been so focused on school and work I've let my physical and mental health (i.e. meditation) slide for several months. I'm certainly working hard and getting some great stuff finished but in the back of the mind I find myself being disappointed in myself. By not doing the things I know I need to do to feel like I'm living my life driven by my values I feel like I'm letting myself down. I'm definitely not inspiring myself to something greater, that's for sure. At the end of the day I want to be able to look at the sum total of my decisions in all realms of my life and be able to admire myself. When I'm consistently breaking commitments to myself to get into better shape or take my meditation practice more seriously it's hard to take myself seriously.

How do you be the type of person you would follow?

It probably varies from person to person just as every leader and follower are unique individuals. For me, I know the main thing I need to be doing on a regular basis in order to be the type of person I would happily follow is:

"Don't break promises."

Obviously, breaking promises and commitments to other people is a bad thing and nobody who regularly does that is going to be a credible leader. However, I'm more interested in the idea of not breaking promises to myself. This is the metric that is more important than whether or not I keep my word to other people because at a certain level there is a social expectation to not screw other people over which helps keep me (and really, everyone) somewhat in line. Crass but true. When it comes to keeping promises to myself, however, nobody but me knows whether or not I do it. It's between me and myself and that's it.

When I'm not keeping promises to myself it means I'm not making smart decisions about how I exercise, about how I eat, about meditation and keeping up my hobbies and other interests. I know the types of things I need to do to feel healthy and happy. When I don't do them even when I have every intention of doing so I'm sending the message to myself that I can't be trusted. I think that lack of trust chips away at the sense that I know what's best for me and that I should work hard to meet the goals I set for myself. 

Why should I follow a guy who can't even keep promises to himself?

For that reason I'm going to try a little weeklong experiment where I focus on doing all my *non-work* habits extremely consistently (for the purpose of this experiment that means daily exercise, daily meditation, and daily journaling). My hypothesis is that by putting more attention on these intentions I have for myself that help support my self-identity as a physically fit, mindful, and deliberately conscious person will spillover into my effectiveness when it comes to writing, coaching, and everything else that makes up my work life. Taking care of these commitments is a signal to myself that I can be relied upon to do the things that I know I need to do to be healthy and happy.

In a nutshell, the foundation of leadership is respect and the foundation of self-leadership is self-respect.

Photo by GrowWear

The List #17

This week I'm sharing a few of my favorite new podcasts and websites that I've added to my information rotation. It's pretty rare for me to actually add (and keep) a new podcast into my listening routine and it's almost as rare for me to add a new website to my RSS reader so I figured the fact that these have made the cut is worth a mention.

Dive into these over the weekend and I don't think you'll be disappointed.

1. Hello Internet

Not only has this podcast broke into the ranks of my regularly listened to shows, it has cracked the top 3 in terms of my all-time favorite shows. The "two dudes talking" genre of podcast is quickly becoming my favorite style and the two dudes talking in this podcast don't disappoint. They're both professional YouTubers (they make videos for a living -- not something root-related) and have great rapport. It helps that one of the guy, CGP Grey, appears to be my personality doppelgänger in a disturbing number of ways.

2. Slate's Working

It has been a big couple of weeks for new and excellent podcasts. This one features an interview with someone from a different profession every week about the details of what they do all day. I absolutely love hearing about the daily routines and habits of people in professions that I know nothing about. Start with the episode about the pastor -- it's great stuff.

3. ISO50

Tycho creates some of my favorite electronic music and it's safe to say his tunes have driven much of my work over the past couple of years. This is his music and design blog where I've stumbled across more visually and auditory beautiful pieces of art than I can believe. Throw this in your RSS reader and you'll be dripped enough great instrumental electronic music over time to keep all your productivity playlists fresh and interesting. Case in point, I've listened to this song obsessively since first seeing it on this blog.

4. 5 Intriguing Things

I unsubscribe from 95% of the email newsletters I subscribe to. This one has made the cut. Basically Alexis Madrigal emails you a list of 5 links with short summaries on an incredibly broad set of topics. The underlying feature is that they are somehow intriguing. I would say I probably add 1-2 items to my Instapaper queue from this newsletter every day. Not a bad hit rate, really.

I'm not bold enough to place this in the actual list, but I've recently started a podcast called The File Drawer and if you like psychology and/or the "two dudes talking" genre of podcast then I'd love if you checked it out. The first episode is published and we are going to be releasing on a weekly schedule.

Photo by Nicholas Lundgaard

The Role of the Individual in the Organization of the Future

I was recently introduced to the work of Undercurrent, an organizational design consulting firm that is really pushing against the edges of how we think about optimally functioning organizations. I’m going to do my best to summarize some of their overarching thoughts, but if you’re really interested you should go straighttothesources.

Organizational Structure for a New Era

In a nutshell, Undercurrent is a proponent of the idea that the most responsive and nimble organizations also tend to be the most effective. Given the speed and power of technology and communication in the world today organizational structures that dominated in the 70’s and 80’s are not the same types of structures that will dominate today and in the future. Instead of creating tall hierarchical structures with clear chains of command and the titles and job responsibilities that accompany a hierarchy, many successful companies are choosing a much “flatter" and in many ways, complex, structure.

Holacracy, agile squads, and self-organizing teams are all the rage and many would argue it's for good reason. With these structures (or really, the lack thereof) companies can be quicker to respond to economic pressures and opportunities. It’s easy to see how this would work for Silicon Valley tech startups but Undercurrent would argue that even well-established companies in less high-tech industries could benefit from moving toward less hierarchy, less structure, and more self-organization.

All of this is fascinating.

Independent Work and Workers

I’ve taken organizational theory and organizational development classes in my PhD coursework and I’ve enjoyed all of them. This talk of structure and overall organizational decision making is incredibly interesting to me and I know quite a bit about it — but it’s also not my bread and butter.

My bread and butter actually has almost nothing to do with people who work in organizations and yet, I think my research interests align incredibly well with the organizational structure movement Undercurrent is promoting. There are questions pounding away at my head as I think about this changing nature of work and organizational life are: What implications does all this have at an individual level? How do you develop (or hire) people who thrive (not just survive) in highly autonomous, uncertain, and ambiguous work situations?

As many of you already know, my research is currently focused on independent workers — freelancers, micro-entrepreneurs, and contract workers. People who start their own thing and keep it deliberately small (for a myriad of reasons). At this moment, I’m particularly interested in the developable skills of self-leadership and self-management for this group of people. Being able to self-lead and self-manage when you work on your own are utterly vital skills to have. Given a lot of the economic indicators and statistics that I’ve seen, I think the growth of independent work is inevitable and already a movement that has been very much set in motion. However, I know that the future of work is never going to be everybody running their own freelance careers or starting independent businesses. Organizations aren’t going away — but I think the way that we’ve thought of organizations for a long time, is.

The Collision of Independent Work & New Organizational Structures

Working in one of these holocratic or highly responsive organizations is going to become more and more like being an independent worker. Autonomy is rampant. Ambiguity about job roles and tasks is a given. A general lack of structure about the how of work is substituted for a focus on the what. As life in organizations becomes more like independent work the skills I’ve begun to identify as being absolutely vital to independent workers, tolerance for ambiguity, self-leadership, self-management, self-awareness, growth mindset, “integrated personal development,” to name a few, are also the skills that anyone working in an organization of the future will need.

How do you develop the people you already have within your organization to be a better fit for this more dynamic, fluid, and uncertain environment? What can be done at the organization level to upgrade the skills of your people? To upgrade the frameworks they use to think about their role in the organization and what it means to do good work on a moment-to-moment basis? Looking outside the organization, how do you make sure you hire people who will be a good fit for this type of environment? How can you make sure you select the people with the highest probability to thrive in an environment that looks more and more like a buzzing and roiling ant hill than an orderly and logical military unit?

I have some ideas about answers to these questions and luckily they spur even more questions within me that seem ripe for empirical investigation. When I originally stepped down this path of indie work research I was a little bit worried that I was setting myself up for failure by focusing on too small a niche. Sure, there are a lot of independent workers in the world and the number seems to be growing, but more people work in organizations. What impact could I really hope to have when I was focusing on a minority of the working population? The work of Undercurrent (and I’m sure other organizations that I’m not aware of yet) has assuaged that fear for me. I now realize that to understand independent workers is to better understand highly autonomous workers regardless of whether they work for themselves, a start-up, or a Fortune 500 company just beginning to experiment with new ways of organizing.

Organizational structures are changing in such a way that requires you to get better. Is there anything more exciting?

Photo by John

The List #16

You're not here to read my excuses but I'm gonna lay some on you anyway. Crunch time on preparing a presentation and then delivering a presentation at the International Leadership Association last weekend, crunch time on getting my thesis proposal signed off, getting hired to do some teaching in the spring... yadda yadda. End result, sparse writing. Another end result, a new The List today because, let's face it, writing these are easy and makes me feel somewhat productive.

Onward!

1. The Printing Press, Literacy, and the Creation of a Secret Society of Adults

A really interesting theory about how television is essentially erasing the differences between adults and children. Probably overstated, but an interesting article nonetheless.

2. Elon Musk's Secret Weapon: A Beginner's Guide to First Principles

The idea of reasoning from first principles instead of analogy or basically boiling down everything to its most fundamental components and then going from there. In many ways, I think this is why I found (and still find) minimalism an interesting philosophy to explore. I've got the beginnings of an article written about applying first principles to our lives that I'm hoping to push out sometime next week.

3. The Art of the Finish: How to Go From Busy to Accomplished

If you're a subscriber to The Workologist Newsletter then you likely saw the article I wrote this month about how being really, really good at GTD can make it easy to do "fake work" most of the time. I've adopted the methodology in this article as of a couple weeks ago and so far it is working really well.

4. How to Be Excellent

This was a relatively crazy/surprising find. Bobby Robins is a professional hockey player who plays for the Boston Bruins (boo!) and is also a really, really good writer. His story is pretty interesting considering he made his NHL debut this year at the age of 32.

With my thesis proposal signed off I now need to start collecting data in the very near future. To aid in that effort, I'm creating a list of people who are potentially interested in participating. In the near future that would mean taking a short survey or two, possibly doing an interview if you're interested, and/or participating in a training program (again, only if you're interested). If you want to be kept in the loop with opportunities to participate in my research you can sign up here.

Photo by Edsel Little

Workologism #3: Use an End of Day Shutdown Routine

Fewer and fewer jobs have clear signals about when work is done for the day. For most of us, the work never really ends. For that reason I think it's really important to create some kind of routine that signals to yourself that the end of your day has happened and you can transition into non-work mode. Some ideas for inclusion in this routine include:

  • Spend a few minutes planning for tomorrow.

  • Clear off your desk and put all work materials away.

  • Spend a few minutes writing in your journal about the day.

  • Turn off your computer.

  • Do something to help you transition from work mentality to home mentality (read something unrelated to work, play a short video game, listen to some music, etc.)

The details don't matter as long as it helps you feel like you're making a transition from one part of your day (productive/work) to another part (not work/relaxing/home).

Photo by Nir.

Relaxation in Work

I recently received some flash cards that contain short quotes about GTD. I've been selecting one at random each week and posting it on the wall near my desk. A couple weeks ago I came across a card that read, “Your ability to generate power is directly proportional to your ability to relax.” GTD aficionados will recognize this concept from David Allen talking about martial arts and the ability of seemingly physically slight people to accomplish impressive feats of strength. This quote came to me at the right time because it seemed like my work life was quickly spiraling out of control to the point of pretty serious imbalance. I was feeling burnt out, run down, and generally exhausted from trying to move forward many projects and meet all the responsibilities I had accepted into my life.

The first time I read the quote it made me think about the importance of taking breaks and allowing myself to rejuvenate. This is important on both a micro and more macro scale. Small breaks throughout the day that allow me to recharge (ala Tony Schwarz and The Power of Full Engagement), having clearly delineated starting and ending points to my day, and even stepping away from work for days or weeks at a time. I was missing all of these components.

The more I reflected on the quote, however, the more I realized that it's actually about more than just taking time away from work to relax and recharge. It's also about the ability to relax while doing work. The state of mental relaxation doesn't have to be separate from the experience of actually being productive. In fact, true productivity may be inextricably connected to approaching work with a relaxed mindset.

I thought about what I'm like when I'm at my best and I realized I never feel like I'm rushing to complete tasks or even feeling heavily emotionally invested in what I'm doing. In fact, my biggest battles with procrastination usually take place when I care about the work I'm doing to such an extent that I can't bring myself to even begin because I care so much about the outcome. However, when I approach my work with a relaxed mindset I'm able to see the experience for what it is -- usually just sitting in a climate controlled room and moving my fingers across a keyboard. When I'm relaxed I can separate myself from the longer-term outcomes of a project and instead focus on the experience of just completing this next task.

For example, I'm currently writing a thesis proposal that is 30+ pages of highly researched and extremely academic writing. I've been working on it for nine months and it has gone through greater than 10 revisions. I care deeply about the subject I'm writing about and I want nothing more than for my advisor to be impressed with the caliber of my thinking and writing and for the research project to be successful. However, sometimes I can get stuck in a rut of not being able to bring myself to read through the next round of comments I receive from my advisor for weeks on end. I get too wound up in both thinking about how much time I've already spent on it and how much more time I have yet to spend. I'm not relaxed and thus I'm generating no power.

Ever since contemplating the quote that opened this article I've been trying to adjust the way I approach giant projects like this. I've been focused on 30-45 minutes blocks of work that in and of themselves do not seem terribly important. Instead of sitting down to "work on my thesis" and wrestling with all the feelings that evokes I sit down to work on "revising the first paragraph of the Introduction" or "rethink the logic supporting hypothesis 1." I don't get all hyped up when I break off a discrete chunk of a project -- I'm able to bring a relaxed mindset to what I'm doing and am thus able to generate more power (i.e. get more done) than I would otherwise.

It's a given that we could all probably use more time away from work, more true relaxation in our lives. While we're working toward that, let's see how much relaxation we can build into our working lives as well.

Photo by Retrofresh!

Workologism #2: Use a Morning Start Up Routine

The way you start your day can have a huge impact on how the rest of it goes. Don't leave it up to chance. Instead, create a checklist of 2-3 activities you know you should complete every morning to get your day started on the right foot. Some ideas include:

  • Spend 15-20 minutes working on an important task.

  • Make a plan for the day.

  • Write in a journal for a few minutes.

  • Exercise.

  • Meditate.

Things you probably don't want on that list:

  • Check email

  • Check social networks

Let's be honest, those are going to happen throughout the day no matter what. Focus on doing the things that make you feel productive, get meaningful work done, or help you develop as a person.

Photo by Ann Fisher

Learn to Focus to Stand Apart from the Crowd

One of the best ways to ensure your continued relevance and even enhanced prestige in anything is to be able to do something that most people can't do. I think it's a good habit to periodically look around yourself to see what skills seem to be in demand that many people are lacking. The most glaringly obvious one to me right now is the ability to truly and deeply focus on one thing. This skill, and that's what it is, a skill, seems to be fading from the personal arsenals of many people I know. I think it largely stems from a lack of adaptation as our world changes under the weight of incredible technological advancements.

The new norm is to multitask when working at the computer. The constant chime of notifications follow us from desktop to commute to personal time away from work as our phones, tablets, and computers become more mobile and ubiquitous. There's nothing inherently bad about information and there are plenty of reasons you may want to be constantly connected. I'm simply arguing that this reality is resulting in fewer and fewer people who can shut out these distractions and truly focus on something for a sustained period of time.

This starts to become important when you realize how much of the truly great work that exists from history and today relies on the ability to focus. Without focus we are constantly flitting across the surface of ideas and concepts -- never diving deep enough to figure out how they are, or may be, connected. Deep insight requires deep focus. Large projects with complex parts require us to shut out the world long enough to interact with information and ideas at a level that can only be reached with sustained focus.

Focus requires effort and it's incredibly difficult. It's easier to be distracted. It's easier to live and work on a more superficial level where the constant tug of distraction is a welcome respite from the hard work of thinking long and deep about challenging things. Luckily, there are two forces working in your favor if you choose to develop this ability. First, because it's so difficult there are less people willing to put in the hard work to get good at it -- making you more valuable and rare. Second, as you may have noticed from my choice of verbs a couple sentences ago, the ability to focus is something you can develop. It's something you can get better at with practice.

I've been spending the better part of the past few years trying to do exactly that. It's a long process and often results in frustration with how slowly I'm making progress. But like anything worth doing, the difficulty is justified.

Meditation and the development of mindfulness is always cited as a great way to develop the ability to focus, and I won't argue with that. My meditation practice, when I'm doing it consistently, is incredibly valuable. However, I think there are other ways you can train yourself to focus better so I'd rather share some of those lesser talked about ways:

  1. Listen to an album in complete solitude.

  2. Watch a movie with full concentration.

  3. Work with a paper and pen.

  4. Read with nothing but the content in front of you.

  5. Wash dishes by hand and in silence.

  6. Run without audio stimulation

Boring? Maybe. Do you have to do these things like this every single time? Of course not. If you don't normally listen, read, watch, or run like this, though, you'll quickly find that it can be very difficult to do these things with full focus. And that's the point. Try picking one of these things to do each week and take notice of what the experience is like. Build up your tolerance for focus over time by slowly adding additional time or activities to your "focus regimen."

You will be one of very few people who knows how to cut through the discord of distractions to bring your mental abilities fully to bear on tough problems. Kind of like when a professional body builder shows up at an average gym, you will be on a different level than most people -- and you will be noticed. Over time you can develop the reputation as the person who works with such deep focus that you can fly through work in half the time as most people and the solutions you come up with are deeper and creative than those who never learned to focus can develop.

It can be hard to predict what specific skills you'll need in the future but it's an incredibly safe bet to think the ability to focus will be at the center of any great work.

Photo by Sylvain Courant

Workologism #1: Multiple Types of Work, Multiple Locations

Have multiple types of work to do throughout the day and access to multiple locations? Try slightly shifting your work environment to stimulate your brain. A recent day of work for me looked like this:

  • Read newspaper and drink first cup of coffee while sitting outside.

  • Stand at my desk to do some administrative work and get organized for the day.

  • Move to outside bar/countertop and a tall chair for second cup of coffee and a couple hours of writing.

  • Respond to emails in recliner in the living room.

  • Move back to standing desk to do a couple coaching calls.

  • Take care of some business reading in hammock on back porch.

  • Go to office on campus to meet with student and do some academic writing.

  • Finish off the work day by doing some editing and more emails sitting at the kitchen table.

Your mileage may vary depending on the types of work you have to do but try expanding the various locations you're willing to work in throughout the day. No need to make massive location changes -- even just changing locations within your office or house may be enough to get your mind moving in novel ways. No reason to chain yourself to your desk if you aren't getting the level of productivity you think is possible.

Edit - Great minds think alike? Cal Newport just published an article with a similar idea he calls a "concentration circuit." Check it out!

Photo by me

A Coaching Case Study: The Challenges of Working From Home

One of the biggest obstacles to working with a coach is simply having no frame of reference for what working with a coach is like. It seems that the majority of my clients end up telling me they wish they had started earlier and that the actual process of working with a coach was not as scary or intimidating as they thought it was going to be. To that end, I'm going to start a series where I offer some case studies of real coaching engagements I've had with real people (with identifying information removed, obviously).

The relevant information for this case is that I'm working with somebody who is transitioning from a traditional 9-to-5 office job to 4 days a week of telecommuting. He's having troubles making this transition to working from home dealing particularly with distraction, lack of productivity, and procrastination. He thought it was going to be an awesome change to his life but now he's wondering if he made a huge mistake.

Here is what our coaching process looked like:

  • Our first session was centered on building rapport and me learning as much as possible about the client. He filled out some paperwork ahead of time to help get me up to speed so we didn't have to spend a ton of time with background information.

  • In addition to building rapport, we spend most of the session talking about why he pushed for this change in work arrangement and what his vision was for how it would change his work and life. I left him with a homework assignment to complete before our next session which involved writing about what being a successful telecommuter might look and feel like to him.

  • In our second session we talked about his homework assignment and really solidified what he's shooting for. We then spent the rest of the time doing a values elicitation exercise to help him get super clear on his underlying values. Once his values were extremely clear to him we started the process of identifying where his current behaviors were falling short of the values he holds. We also identified where in his life and work his behaviors and values are aligned. We started creating a list as we ran out of time in the session. His homework was to finish creating the list.

  • We started the third session by looking at the list of mismatches between his values and his behaviors. I had him pick the one that seemed the most important. He homed in on the idea of a lack of discipline in the way he has treated his working from home even though Discipline is one of the values that emerged from his values elucidation. We started talking about the changes he would need to make to bring more discipline into his work. We brainstormed a bunch together and I asked him to pick just one to focus on for the next week. He decided that he wanted to try a Morning Start Up Routine that involves planning his upcoming day, writing in his journal, and completing 20 minutes of his most important work task before checking email or any social networks.

  • I sent him an email a couple days later to see how things are going and offer some support.

  • We started our fourth session talking about how the Morning Start Up Routine experiment went. He found a decent amount of success when he did the routine but forgot to do it a couple of days. We talked about how he can prevent himself from forgetting to do it in the future and he decided to add it as a recurring task on his calendar and he made a little note to stick to the bulletin board in his office. He decided to try adding on an End of Day Routine experiment and we talked about how he could best install that habit given what he learned from the Morning Start Up Routine experiment.

  • Moving into our fifth and final session he felt pretty good about the two experiments he had done so far. In order to make sure progress was going to continue after this final coaching engagement we spent most of the session creating a list of other experiments he can do to reduce the gaps between his daily behaviors and the values we elucidated in our second session. We spent some time talking about the order in which he should tackle these and how he will judge whether he was successful. This led us into a brief discussion about the importance of self-reflection and this prompted him to add the development of a self-reflection routine into his list of experiments.

  • We finished up the final coaching session with a virtual high five and the promise to check-in after a couple months to see how everything is going and possibly consider an additional "booster" coaching engagement if he feels it's necessary.

Coaching Toward Self-Development

Across five sessions he made serious progress on tackling the productivity issues that emerged from shifting into a telecommuting role and not being used to that style of work. Most importantly, he built his capacity to self-develop by going through the process of identifying mini-experiments he could conduct by himself and then coming to conclusions about whether or not they are improving his situation. Any good coach should be able to teach his or her clients how to continue coaching themselves after the coaching engagement is completed.

Hopefully that gives you a bit of a glimpse into what a potential coaching engagement with me actually looks like. Do you have any other questions about the process of coaching? Shoot me an email (samspurlin@gmail.com) or leave a comment.

Photo by Arlo Bates

The List #15

Welcome to another edition of The List. The List is a curated list of my favorite things from the past week. Articles, videos, podcasts -- the media always changes but the unifying characteristic is that I loved whatever I end up sharing.

1. Advanced Tricycling by Merlin Mann

I look forward to new Merlin Mann talks like most kids look forward to Christmas morning. I'm an unapologetic fan of what Merlin does and how he thinks about what doing great work looks like. This is his latest talk about what it means to get better at something and how to even know what you're supposed to be getting better at.

2. Looking at Productivity as a State of Mind by Sendhil Mullainanthan (NYT)

Factories imposed discipline. They enforced strict work hours. There were rules for when you could go home and for when you had to show up at the beginning of your shift. If you arrived late you could be locked out for the day. For workers being paid piece rates, this certainly got them up and at work on time. You can even see something similar with the assembly line. Those operations dictate a certain pace of work. Like a running partner, an assembly line enforces a certain speed.

As Professor Clark provocatively puts it: “Workers effectively hired capitalists to make them work harder. They lacked the self-control to achieve higher earnings on their own.”

A provocative and fascinating idea about the Industrial Revolution -- and I think it has merit. There's something to be said for the external pressures that force us to work hard and have discipline. When I talk to independent workers one of the things I hear most commonly is how difficult it is to be productive and do great work when working from home and/or for yourself.

It seems to me that the future of work is a matter of finding the balance between the oppressive yet highly productive paradigm of the Industrial Revolution-era factory and the incredibly autonomous yet completely structure-less la-la land of independent knowledge work. Building external pressure into your work day while also allowing for autonomy is a delicate and important balance.

3. Why I Just Asked My Students to Put Their Laptops Away by Clay Shirky (Medium)

If I ever teach in a college setting, I'm going to make this article required reading on day one. It's the best argument I've heard for why laptops should be put away during most college classes. I've always felt that it was important for students to be treated like adults and if we wanted to use our computers in class then we should be able to. However, Shirky makes some points that makes me realize it's more complex than that:

"The fact that hardware and software is being professionally designed to distract was the first thing that made me willing to require rather than merely suggest that students not use devices in class. There are some counter-moves in the industry right now — software that takes over your screen to hide distractions, software that prevents you from logging into certain sites or using the internet at all, phones with Do Not Disturb options — but at the moment these are rear-guard actions. The industry has committed itself to an arms race for my students’ attention, and if it’s me against Facebook and Apple, I lose."

And,

"Anyone distracted in class doesn’t just lose out on the content of the discussion, they create a sense of permission that opting out is OK, and, worse, a haze of second-hand distraction for their peers. In an environment like this, students need support for the better angels of their nature (or at least the more intellectual angels), and they need defenses against the powerful short-term incentives to put off complex, frustrating tasks. That support and those defenses don’t just happen, and they are not limited to the individual’s choices. They are provided by social structure, and that structure is disproportionately provided by the professor, especially during the first weeks of class."

If you're a professor, I'd love to hear what your take is on this article and your own policy for computers in class. If you're a student, this article might make you think about your computer usage in a new light as well.

Photo by Katherine Lim

There Are Some Things $100 Million Can't Buy

Months ago there were a spate of articles in the Wall Street Journal about Mohamed El-Erian leaving his position as CEO of Pimco, one of the world's largest financial companies. I had never heard of him and I had only recently started reading the WSJ so I didn't really know Pimco, either. I do remember being struck by how surprised everyone seemed and how there was obviously something going on behind the scenes. Most people chalked it up to a clash of personalities between El-Erian and Pimco's co-founder Bill Gross and everything seemed to go quiet for a couple months.

A couple weeks ago El-Erian surfaced again and the full picture behind his departure is a little bit clearer:

About a year ago, I asked my daughter several times to do something -- brush her teeth, I think it was -- with no success. I reminded her that it was not so long ago that she would have immediately responded, and I wouldn't have had to ask her multiple times; she would have known from my tone of voice that i was serious.

She asked me to wait a minute, went to her room and came back with a piece of paper. It was a list that she had compiled of her important events and activities that I had missed due to work commitments.

Talk about a wake-up call.

Now he works as an economic adviser with Allianz and work takes up about 50% of his time.

From my perspective, this looks a lot like why many people choose to go into independent work. Granted, El-Erian is not a typical independent worker considering he made roughly $100 million last year. It's obviously easier (if not easier, at least more financially viable) for him to scale back his work hours and spend more time with his family.

On a very simple level, this is great evidence of what deliberate decision-making about work can look like. Regardless of our level in an organization or our income we can choose to think about what matters the most in our lives and then take steps to make decisions that support those values. The beautiful part is that this looks different for everyone. The only similarity that I'm pushing is the commitment to being deliberate about the course of action taken instead of locking into a groove and plowing away, heads down, for 40 years without taking a second to look around or ask some reflective questions.

What's the smallest step you can take to make your work more meaningful?

What's the smallest step you can take to make your work more enjoyable?

We can't all make $100 million a year or be CEOs of huge financial firms but we can all make deliberate decisions - even tiny ones - that better align our work, lives, and values.

Photo by Fortune Live Media

Creating a Sense of Progress

One of the biggest challenges for any kind of knowledge worker, especially for those who work independently, is feeling like you're never making any progress. When I was a teacher I very rarely felt like I was making any progress because I felt like I was on a treadmill of lesson prep and delivery. When I got to graduate school I quickly realized that the work never finished there either. No matter how caught up I thought I was, there's always something else I could/should be doing. Now that I have one foot in graduate school and one foot in my professional/entrepreneurial career, I'm realizing that sense of progress I've been craving and missing from before is still the same.

Occasionally, though, I'll get a glimpse of what it feels like to truly make progress. I'll have a big week and knock off two or three meaty and substantial projects. It'll feel like I have actually covered some ground -- that I've moved from point A to a distant point B and it feels incredible. For that reason, I've been trying to pay closer to attention to how I can build more progress into my work.

First, progress is simply the sensation of moving forward on meaningful projects. It's not simply doing a lot of stuff, it's doing a lot of the right stuff. It's the sensation that arises when you realize you're actually closing the gap between reality and your goals. It's being able to look at the ground you've covered so far and making a realistic prediction about when you might be able to finish something.

Second, developing a sense of progress is vital to experiencing flow in your work. In his research Csikszentmihalyi identified three prerequisites to experiencing flow: having a high skill/challenge ratio, having clear goals, and having clear feedback. The combination of having clear goals and clear feedback is also called progress. Without it you don't know if you're heading in the right direction and you're never able to fully lose yourself in the task at hand because you'll be too preoccupied.

Without a sense of progress it's a given that there will be no flow. You will also lose motivation. You will be frustrated. You will push yourself closer and closer to burnout.

Luckily, there are some things you can do to help create a sense of progress as a highly autonomous worker dealing with data, information, and knowledge instead of widgets to be cranked. Here are a handful of my favorites.

1. Work Logs: Looking back at what you accomplished at the end of a period of time and making some kind of record of it is a great way to cultivate a sense of progress. You could close out your day by taking 5-10 minutes and writing out what you did. I actually really like to do this on a monthly basis by asking myself, "What notable things did I do this month?" It's very cool to be able to look back at 12 months of entries and see a complete list of all the things I did that I felt were notable.

2. Keeping a Shipped List: When you finish something substantial don't just cross it off your list and let it slip into the depths of your memory! Slap that bad boy on a "shipped list" and keep it somewhere prominent! I like to keep part of my whiteboard reserved for a list of the major projects I've shipped in the past 2-3 months. It feels good to look at it and see how much I've accomplished.

3. Setting Clear Goals: Like I mentioned when writing about flow earlier, having clear goals is a key component of getting a sense of progress. Goals can operate at multiple different levels, but there are two types of goals I tend to set that I think have the biggest impact on my sense of progress; daily and weekly. Weekly goals are set during my Weekly Review and are usually 1-3 large/medium things I want to accomplish over the work week. Daily goals are the 2-3 things I should accomplish on that specific day to feel like I did what I set out to do. Force yourself to make your goals specific, measurable, attainable, relevant, and time-bound (SMART, yo!).

4. Using Checklists: Checklists are a relatively new addition to my workflow but I'm really digging the sense of progress they give me. I wrote more about them here but in a nutshell checklists help me offload the chore of remembering the specific things I know I have to do in order to have a good day/week/month. As an added bonus (and particularly relevant for creating a sense of progress) checking items off a checklist is supremely satisfying and a great way to feel like you're making progress.

If you have other ways you build a sense of progress into an otherwise progress-less work life I'd love to hear about your strategies in the comments!

Photo by Brent Daley

The List #14

Happiest of Fridays!

I'm going to kick off this week's The List by being a presumptuous ass and linking to my own article. I had the privilege of having my third article published at 99U. It's about this idea I've been obsessing about for awhile and is really hard to write about coherently. Basically, what does it mean to work with dignity? I'm impressed they decided to run it because it's not necessarily the type of article that's likely to go viral but I think the ideas behind it are really important. It would mean a lot to me if you checked it out.

Which Habits Should I Focus On? - Charles Duhigg

This is a great article from the guy who wrote the book on habits. It answers one of the most common questions clients of mine often have in a really articulate and intelligent way. If you're interested in habit change and are wondering where to start you could do much worse than checking out this article.

Silicon Valley's Contract Worker Problem - New York Magazine

The more I read about the sharing economy and services like Uber, TaskRabbit, and other platforms for "independent work" the more I'm realizing this isn't what I mean by independent work. Independent work deliberately chosen for the benefits one gains from working in this fashion is not the same thing as working for these various platforms as an independent contractor so these companies can get away with not paying benefits and the other responsibilities of having employees. I need to develop my thinking on this further but its articles like this that are causing me to pause and think.

What are the best things you read this week?

Photo by Nicolo Paternoster

Digital vs. Analog: The Battle of Productivity Systems

A couple weeks ago I was honored to be mentioned on an episode of Mac Power Users about task management. Listening to David and Katie talk about task management systems got me thinking about how my system has evolved over time. One of the most common questions I hear from people who are interested in developing some sort of system to manage their work is whether they should go analog (paper, pencil, notebooks, folders, etc.) or digital (software, paperless, tablets, phones, etc.).

There's a certain concreteness, a solidity, to using an analog system. Shuffling papers, arranging notes, and actually manipulating physical material can be a great way to make your system feel more alive and personal. On the other hand, going digital means being able to handle more information more efficiently and being able to always have the entirety of your system close at hand. I used to agonize whether I'd be better off going full-digital or full-analog until I realized that was a stupid false dichotomy. I could, and should, do both.

The ultimate goal of any productivity or work management system should be tied to completing the work itself, not the details of how it's managed. Getting organized is a step on the path to doing meaningful work as well as living an overall more deliberate life. There are no style points to be won for sexy systems, no competitions for who can manage the most information, or who can have the cleanest all-digital or all-analog system. Liberating myself from the mindset that I had to choose one over the other allowed me to take the best from both worlds and craft a system that is intimately tied to the ways I like to think and work.

The Digital

My digital system allows me to capture information at will and with a minimum of effort or friction. It allows me to manage the influx of information that we all seem to have to deal with in a constantly connected world and a work life that never really seems to turn off. The digital components of my system include:

  • Capturing photos with my iPhone that are automatically sent to Evernote via IFTTT (receipts, reminders, paper notes, etc.).

  • Capturing thoughts, next actions, and ideas with the Things iOS app.

  • Using Evernote as a "digital filing cabinet" for storing all archived project materials as well as active reference material.

  • Using Gmail, archiving all emails, and trusting my ability to find anything I might need from my past with some simple searches.

  • Using Things to manage all my active and deferred projects, next actions, and someday/maybe ideas.

  • Using Fantastical to manage my calendar on my computer, iPhone, and iPad.

  • Using Dropbox to store active project documents (which are moved to Evernote once completed).

The digital component of my system allows me to be highly mobile and trust that I can do my work wherever I happen to be. The somewhat ephemeral nature of digital information also allows me to not worry about how much stuff I'm throwing at my system as it's easy to filter and search for what I need. If I were using a paper list to keep track of all my next actions I may be more hesitant to add something minor to it. By using Things I don't feel that hesitancy which allows me to be much more complete with the capture component of my organizational system.

The Analog

The characteristics that make my digital system awesome are also what makes it insufficient for a truly complete organizational system. Since it's so easy to throw a lot of information at it and store it in a simple way I have a ton of information in it. Having to look at my entire system every time I need to make a decision about what to do next would be an extremely draining system. That's one reason I've evolved the analog component of my system.

  • I create a daily index card that has my hard landscape responsibilities (primarily appointments and meetings with their requisite pre-work) written on it. At the start of the day I will also add 2-3 goals for what I want to accomplish today. This notecard is then clipped to the cover of the notebook I carry with me throughout the day.

  • I have a black notebook with perforated pages that I use to take notes throughout the day. At the end of the day I tear out the pages I used and throw them in my physical inbox for processing.

  • My physical inbox is the landing strip for all the physical pieces of information that come into my life. I'll empty the papers from my bag into it at the end of the day, snail mail, and any other physical items I need to process. The inbox gets processed every other day or so.

  • I have a black box with a handful of manila folders for storing my physical reference files. If I can I'll scan something and add it to Evernote but if it's something I feel like I should keep a physical copy of it goes in this box.

  • My whiteboard is attached to the wall next to my desk and it's where I keep some weekly, monthly, and longer term goals listed. I also use sticky tack to mount my pre-made daily index cards during my weekly review. I'll also use it for my first round of mind mapping when planning an article or other project (this article started as a mind map on my whiteboard).

  • I'm experimenting with keeping reusable paper checklists for daily, weekly, and monthly activities I know I want/need to complete. The monthly and weekly checklists are tacked to my whiteboard whereas the daily one usually just sits on my desk or is clipped to my notebook.

The analog component of my system allows me to focus in on a much smaller time frame. I'm able to see my daily goals and simply focus on those instead of having to constantly live inside my relatively massive digital system. It's kind of like going to the bank. I know I have more money than I actually need for the week or day in there so instead of carrying around my entire life savings I just withdraw what I need on a regular basis. My digital system is my bank with the entirety of my information living in it and I withdraw what I need into my analog system on a regular basis.

The linchpin to this system has always been my weekly review. With the weekly review installed into my routine I know that I can let go of my larger system and just focus on getting work done for seven days at a time. Regardless of what has changed in my life or the new information that has been thrown at me, I know I'll take a step back and reassess every week. This frees me up to not use mental cycles constantly thinking about the changes in my life or worrying about what I might be missing -- I know I'll take a look at the whole system soon enough.

If I had a straight analog system I'd worry that I wasn't keeping a truly complete collection of everything I have to do. If I had a straight digital system I'd be distracted by the sheer immensity of the information living in the system. By embracing both I've been able to create something that melds together the best of both.

Photos by Jens Schott Knudsenand Jenni C

The List #13

Since last week's List was a special positive-psychology edition a few of the articles I'm sharing this week are a little bit older. Doesn't mean they aren't awesome, though.

I also want to start casting my net a little bit wider when it comes to what I read on a regular basis so don't hesitate to share some of your favorite sources of reading in the comments or via Twitter.

Kick back with a cup of joe this weekend and enjoy some of my favorite articles from across the web.

America, Say Goodbye to the Era of Big Work - LA Times

I know this website does not appeal exclusively to independent workers -- and that's perfectly awesome. I'm interested in the idea of meaningful and engaging work regardless of the specific context. However, I do have a soft spot for articles about the growth of independent work as it is directly related to my academic/research interests.

The Strange and Curious Tale of the Last True Hermit - GQ

This is just one of the most interesting articles I've read in awhile. Fascinating story about a guy who lived in the wilderness for an insanely long time. There's something about the need for solitude somewhere in here as well. But mostly it's just a really interesting story.

Reboot or Die Trying - Outside

I'm a sucker for stories about people doing things to take deliberate control over the role technology plays in our lives. Between this and the Distraction Free iPhone article (which inspired one of my articles from earlier this week).

John Cage on the Necessity of Boredom - Cal Newport

I feel like every time Cal writes something on his site I end up sharing it here. Obviously, I'm a bit of a fan of the stuff Cal does and how he writes about it. This is a super short one, but it's a great reminder for anyone trying to do creative and meaningful work.

“If something is boring after two minutes, try it for four. If still boring, then eight. Then sixteen. Then thirty-two. Eventually one discovers that it is not boring at all.”

Photo by Jason Thompson

Write an Article About Checklists; Check

My weekly planning process is constantly evolving as the demands of my world change along with my understanding of how I can be at my best. I recently came to the somewhat obvious realization that there is a certain percentage of my work/life that happens every single day, every week, and every month. These items are a combination of mundane administration, meaningful work, and aspirational intentions. When these things happen at a pre-determined regular interval I know I'm much more likely to feel better about my work and life.

I decided to use this realization to more systematically plan and manage my days/weeks/months. The first step was to simply brainstorm the items that I know need to happen regularly in order for me to feel good about what I'm doing. Thinking about what I have to do on a daily basis to keep my life running I came up with this list (all lists in this article are slightly edited to censor confidential information):

  • Read Wall Street Journal

  • Make bed

  • Take vitamin

  • Meditate

  • Exercise

  • Write in journal

  • Read for enjoyment

Mundane? Yes. However, these are the tasks I know I need to complete every day in order to not feel like I'm slacking in some regard. Obviously that's not everything I need to accomplish in a day. It's more like the bedrock on which more meaningful/important/urgent tasks are situated.

Similarly, there are a handful of things I know I need to accomplish every normal work week in order to meet my current life and work responsibilities:

  • Do some bulk cooking or make sure I still have enough leftovers for quick/easy lunch and dinners.

  • Read through all the academic articles I set aside for this week's reading.

  • Draft two articles for The Workologist (plus a link post on Friday)

  • Complete all my teaching assistant responsibilities (go to my office hour, read for the upcoming week of classes, go to the classes, respond to student emails, submit time sheets)

  • Complete 10 hours on [consulting project I'm contracted to work on 10 hours a week].

  • Do my Weekly Review

  • Go to my weekly hockey game.

  • Finish the week's issue of The Economist.

  • Record [podcast I'm currently piloting with a friend].

  • Have Outlier Consulting Group meeting with Jeff.

These two lists contain, at the very last, the starting points for high functioning days and weeks. Doing some of these things is pretty automatic but some of them require more conscious thought. These tasks are very important and are a key aspect of me feeling good about how I'm doing but at the same time they don't really represent the work that other people are expecting from me. I need to do these things but the quicker and more efficiently I can do them the more time I'll have to work on other things. Putting them on easy to access checklists makes sure I'm not forgetting anything and lets me focus all my energy on getting them done efficiently without having to also remember what they all are or if I'm forgetting anything.

Finally, on a monthly basis I need to complete the following:

  • Write/publish The Workologist newsletter.

  • Complete 2-3 hours of focused business development activities.

  • Draft and record en*theos class.

  • Draft and submit [monthly freelance article].

  • Conduct monthly review.

The other work that exists in my life is either a semi-weekly project/task, a discrete/one-off project, or brand new information that either becomes something I have to do on a recurring basis (daily, weekly, semi-weekly, or monthly) or a one-off task/project.

By thinking about my work with this framework of recurring/discrete projects I'm gaining much more clarity about what should be a constant in my life and what I need to be more deliberate about creating time to work on. It's helping me figure out how to use my time more efficiently and allowing me to be more conscious about what I can actually feasibly accomplish. When I sit down to plan my day/week/month I can start by looking at my checklist and figuring out when I'm going to get these tasks done. The more efficient I get at these ongoing maintenance tasks the more time I'll have to complete all those projects that aren't recurring -- which happens to be the vast majority of the work I have to do. This method is helping me make sure I'm always doing those things that have the largest impact on my sense of well-being while still getting all my work finished.

Like my Weekly Review template, I expect these lists to evolve over time as my circumstances change. Even looking at them now I'm feeling like there are some more aspirational things I can add to them. For now I'm going to keep them nice and simple and if they become extremely easy to finish I'll consider adding new components to them. The important thing is to be okay with changing them over time because otherwise they will cease being relevant and I'll stop using them.

How to Build Checklists Into Your Planning

The first step is to spend some time figuring out what you need to do on a daily basis in order to feel like you're doing a good job in your work/life. Jot it all down on an index card, laminate it with some packing tape, and now you have a daily checklist you can write on with a dry erase marker and carry with you. Do the same thing with the tasks you know you need (or want) to complete on a weekly basis. Again, laminate it and then display it where you'll see it regularly. Do it again with your monthly tasks/projects. Finally, create a list of all the projects you're currently working on that have some sort of "done" state.

The recurring daily/weekly/monthly checklists are made up of tasks that you'll never stop doing -- at least not any time soon (I may stop feeling like I need to read 4-5 academic articles every week but that won't be for years down the road). The list of discrete projects is what you'll pull from to fill in the time around your recurring daily/weekly/monthly tasks. Over time you'll check these projects off the list and add new ones. Determining what to work on at any given time or which of these discrete projects should be prioritized is outside the scope of this article, but using this technique to get a handle on everything you need to do on a daily, weekly, monthly basis will make sure you're moving forward everything you've deemed as important without letting maintenance activities fall by the wayside while you focus on "real work" and vice versa.

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Photo by Palo