The False Dream of a Clear Path

I have this fantastical daydream that I entertain often: I get a week (or weekend) to myself and I am able to do all the work, all the projects, all the catching up that I want to do. Sometimes I go on a trip to achieve this, or maybe a blizzard has me stuck in some hotel room in the Midwest with nothing but Wifi and a computer. Perhaps all regular work stops and I am able to work on what I want to work on without financial pressure.

This fantasy is fed by stories that I hear about artists and writers who move to little cabins in New England to focus. Annie Dillard did all her work in a one room shack in the backyard of some small lovely town near Seattle; Harper Lee was given enough money to work on To Kill a Mockingbird for one year.

Whatever your exact conditions for dream productivity let me fill you in: this is a terrible, false dream. No real work has been created under ideal conditions. In fact, the more important the work the more obstacles you will face.

Any who have attempted bold things has felt this. Try doing something timeless like raising children, starting a diet, trying to help others – you will meet resistance on all sides.

Rule of thumb: The more important a call or action is to our soul’s evolution, the Resistance we will feel toward pursuing it.
– Stephen Pressfield, The War of Art

We are all full of excuses and awful stories of sick children, serious personal injury, our common time and energy constraints, and unexpected family crisis.

But we shouldn’t be surprised, we should be joyful, because when you meet resistance, when you feel those distractions this is when you know that the work that you are doing is important.

Raising kids is a direct spit into the overriding rule of disorder in the universe, and we will feel it push against us.

When we have troubles, we must expect them, push through them, and win. For we are doing higher work, and we have our own forces and must call upon them.

The 5-minute Journal

Last year I bought, in some sort of moment of defeat against the capitalism of productivity tools, a product called The 5 Minute Journal after hearing a few people talk about it.

(Important note: since I bought it the creators have created the following video which would have made me not buy it if I had seen it before, probably due to my overwhelming jealousy. Who in Oden’s name gets to wake up like this?)

The product is meant to increase mindfulness and focus. The idea is pretty simple – you spend a few minutes answering the following every day:


I am grateful for ____ [3 things].

I am grateful for ____ [3 things].

What would make today great?  [3 things]

Daily affirmations.  I am… [2 blank lines]


3 Amazing Things that happened today… [3 things]

How could I have made today better?

2016-04-20 08.51.25

I bought the physical product and wrote in it, but they now have an iOS app.

Actual Science

The exact questions are based on positive psychology and the work of Dr. Martin Seligman (author of Authentic Happiness, Learned Optimism, and Flourish).  In his research, he has shown that remembering positive events, expressing gratitude, and focusing on our core strengths and help people climb out of depression.  I knew none of this when I bought this book; I simply heard Tim Ferris say it was cool and if you listen to enough Tim Ferris eventually you will try something he is trying.

My experience

First, I was surprised at how many times I forgot to do it at night. Apparently in the morning I have a very complex “getting started” ritual and an “end working” ritual, but no “going to bed ritual”. My getting started ritual always happens at my desk, but the good night ritual happens upstairs so I never saw the book to remind me to do something.

Once I established it as a habit it was very interesting to see what I put in there for goals and positive outlooks. An important detail to note is that during the time [sprint 2015] I was using it school ended for my kids, and both my wife and I tweaked our back (separately) and started going to physical therapy. It was at times very frustrating as health issues often are – I would feel better and then she would feel worse, and all the kids being around didn’t always help either of us rest.  It was a frustrating time and you can see this reflected in the journal. Rather than just being down about my back I would say things to it like “What would make a good day?” and I would put stuff like My back is the same, and my wife’s is a little better and I would have to say that to myself a few times – define the day-by-day by that criteria.  At the end of the day I would have to write that, in fact, our backs were the same or a little better and forced myself to define the day as a win.


I could see this tool helping you to change the way you think slowly over time, especially with large goals. If you are looking to get into college telling yourself a few more times a day will not hurt you and will help you stay focused on that goal. And the “end of the day” items were very interesting – you dream about things you are worried or anxious or have just thought about, so a positive reflection on your day is and effective routine before you go to bed. It simply works.

I struggled to know what to put in the “Daily Affirmations” box. Struggling to figure out what I would put there made me end up putting a goal in there “working towards X” or a reminder of a core strength “good at coming up with ideas”. I never knew that a small book could turn me into Stuart Smalley but here we were.


Another thing that is obvious but made me feel good is that at the end of the day it served as a way to remember good things that happened. One of my implicit life goals is to hold my temper and be patient with my children. They do not share this goal, but I found myself simply writing down “did not yell at kids” or “good day with kids” or “0 tantrums from anyone” day after day and realized that things were going pretty well. And reminding yourself that things are overall going pretty well is a very powerful idea.  And the real revelation with this journal is that there were times when I wrote things I never would have expected like “nice sunset tonight”.

Personal Retreats

Every year I take a weekend to myself and go on a personal retreat. This tradition started years ago when I took a sick day from work and rode my bike from Atlanta to Alabama and back.  When I returned I felt like I had been on vacation for weeks: my energy and spirit were renewed and I was overflowing with ideas (and my legs were sore as hell).  The hours of mindless riding had given me time to think.

I decided to make it a tradition. Over the years, the activities have grown less physical but the core purpose remains the same:

  • Get away from typical activities
  • Get quiet
  • Think about my long-term goals across areas of my life
  • Generate ideas

I type up the following questions before the retreat:

For my roles (father / husband / employee / human being, etc.):

  • Am I headed in the right direction?
  • What could I be doing better?
  • What should I stop doing?
  • If I took my role as (insert role) more seriously, what would I change?
  • If I was to be judged only by one role which would I want it to be and what next steps would I make to how I act in that role now?

I ask myself these questions (and type up a few short answers) before the retreat, and then I just try not to think and let my mind relax and wander. I have found that the insight and relaxation that comes from these retreats to be invaluable. I considered this tradition a personal quirk that flows from my natural inclination to be an introverted-ideation-thinker-type, so I was surprised to hear about the book The Zen Founder’s Guide to Founder Retreats.

The book discusses a “founder” retreat although its advice isn’t specific to startup founders. This little book contains some great advice that I agree with from my retreat experience:

Start the retreat out doing nothing to get the worries of the day away and shift your mindset to relax a bit more. Unplug very aggressively – this is a “time-in” not a “time-out” from work, but not the day-to-day. 

My first retreat not-on-a-bike I found myself “catching up on work” which limited my success. The time away should be planned as a notification-less time as much as possible.  The book recommends using pen and paper (what are those?) for the planning and note-taking to enforce this.

Reflect on your past growth and successes as well as planning for the future.

The book guides you through some reflection questions around optimizing your business and personal development viewed through your past.  My natural tendency is to focus on areas of improvement which steers things negatively; this focused reflection reminds you of strengths.

Avoid making decisions when you are low-energy.

This really isn’t retreat-specific advice but is just good life advice.  The book uses the acronym: HALT (don’t make a decision when Hungry, Angry, Lonely, or Tired) They also mention avoiding big decisions when Vengeful, Irritated, or Ashamed.  No word on what you should do when Forgetful.

Ask Big Scary Questions.

Retreats are a great way to step back and ask scary questions such as “Am I in the right career field?“, “Should I quit my job and go pro with my juggling?” and “Can my marriage be saved what with all the fighting about juggling?

The book goes over this very well and points out that retreats are the best time to ask these questions but don’t put pressure on yourself to have an answer by the end of the retreat; the point is to examine it under the positive conditions of the retreat to help the final decision-making process.

Overall I loved this quick read and recommend it and taking personal retreats (even if they are just an afternoon) to anyone with any serious responsibility.  Check out The Zen Founder Guide to Founder Retreats on Gumroad.

Obsession with Tools

Last year I wrote, but I also wasted a lot of time not writing. I read more and wrote a book while procrastinating writing another one.  Looking back I can see a good deal of fake work performed – work that did not move the ball forward but felt like work – and one specific case of this type was an over-obsession with tools.

With great shame I present the following screenshot from my present day machine:

I also used 750 words and Draft and played around with any new writing tool I hear about (latest: The Most Dangerous Writing App).

11 tools to type? Why did I do this?

Because it felt like work – it felt like I was a professional – and so I gave myself a break.  I would get ideas for the book or work so I did need a way to capture these quickly and easily, and Evernote was a solid solution for this.  It would be nice to have a tool that easily stored the chapters and allowed exporting to Kindle, etc.  But these items distracted me from the core work of writing the book.

At the end of the day, you don’t need that many tools to really work.  After I was cranking away my toolset got real simple:

  • Plain text or markdown stored on Dropbox.
  • Evernote for idea captures.

That’s it.  The real tool isn’t some software or hardware it is time.

All of the time I spent evaluating tools I should have instead been establishing a daily ritual of writing.  That habit, once established (even 15 minutes a day) trumps any gain in productivity by a tool.  Feedback from that process (such as “it would be nice to tag things easily for searching” or “I wish I could export this to PDF and print easily”) should have driven tool purchases and not things like “this one looks cool” (OmmWriter) or “I think I need this one to really be a writer” (Grammarly).




You Need a Don’t Do List

Most people agree that a “to do list” is a great way to track work tasks whether it be shopping lists or work lists or people that you need to tickle this week. But for most workers, especially those that work from home, you also need a Don’t Do List.

This is a simple list of behaviors that you know can ruin your workday. In addition to the obvious things like ‘Watch TV’ or ‘Open up without a plan’ there are some more subtle ‘don’t do’ items that you need to identify and make a plan to avoid.

But first let’s list the relatively obvious ones for a telecommuter:

Don’t Do:

  • Watch TV during the workday (even at lunch)
  • Play video games.
  • Browse reddit,,,,
  • Snack when you aren’t hungry.
  • Check your email. (Stop and acknowledge that checking email is essentially saying “I want more work and stress now”)

Now the more subtle emotional ones:

Don’t Do:

  • Get discouraged.
  • Prefer fake work.
  • Avoid the really hard important tasks.
  • Respond too quickly to an email that frustrated you.
  • Panic.

Everyone’s personal don’t do list is different and will shift over time. There was a time when I could work and listen to podcasts but then I realized it got to be too distracting, so it moved from my bag of tricks into my don’t do list.

Some items you can’t avoid doing altogether but have to manage as ongoing tensions. One of these for me is distractions caused by my family. I know that each day at least once I will be taken away from my normal level of concentration (that of a tiger watching the zookeeper put the string on a piece of raw beef) by some noise of a kid picking the lock to my office to use my printer or a kid throwing mud at my office window.

So my “don’t do” list is simply to not let this stuff bother me. I mitigate this risk with my attitude.  All other items I simply put in a box to do be done later; I don’t do them so that I can get the real work done consistently.


I’m writing a book about successfully working from home; click here if you want to know when it is complete.

Fake Work

We have all been there – you are busy all day but as the day ends you still haven’t done The One Thing that you really should have finished today. What were you doing all day? Fake work. You fell into the trap of fake work.

From Paul Graham’s post on Self Indulgence:

And yet I’ve definitely had days when I might as well have sat in front of a TV all day—days at the end of which, if I asked myself what I got done that day, the answer would have been: basically, nothing. I feel bad after these days too, but nothing like as bad as I’d feel if I spent the whole day on the sofa watching TV. If I spent a whole day watching TV I’d feel like I was descending into perdition. But the same alarms don’t go off on the days when I get nothing done, because I’m doing stuff that seems, superficially, like real work. Dealing with email, for example. You do it sitting at a desk. It’s not fun. So it must be work.

Characteristics of Fake Work

  • It’s easier than real work (this is why we prefer it)
  • It isn’t obvious to people that you are doing it (fake work is rarely publishable / shippable)
  • It doesn’t pass the following gauntlet of tests:
    1. If I did this all day how would I feel at the end of the day? Does it feel good in the short-term only?
    2. Can I justify it to a coworker? (“Well these files need to be organized by color name in Spanish so that we can get to them rapidamente next time”)
    3. Is this defensive or offensive?

Some examples

  • Your computer says it needs to restart, and you restart it shortly after. “When it restarts I might as well see if any apps need updating as well on my phone”.
  • You know the hotkey for your “get new email” in your email client. (I mean really)
  • Organizing your todo list.
  • Refactoring code is non-complex ways.
  • Trying out a new writing application or messing around with new fonts.
  • Organizing your email.
  • Reading blog posts, especially those mildly related to The Important Task That Must Be Done.
  • Over-formatting presentations, spreadsheets, etc.
  • Cleaning your office.


There are times that you need to read blog posts or clean your office. In fact one of my favorite productivity hacks is to do *something* when I’m feeling procrastination creeping up on me. I will intentionally clean my office as a break with the intention of returning to full strength afterwards. The trick is to not let doing *something* ruin doing the *one most important thing* that must be done.

Final Note

The main issue with fake work is that you could be working on the right things in the wrong place. Do you care about the problem? Are you digging in the right place? This is a complex personal question, but make sure you have an answer.

I’m writing a book about successfully working from home; click here if you want to know when it is complete.

Staying Productive: Take Real Breaks and Keep away from Ace of Base

My productivity tip of the day is pretty simple and exists in two parts:

Take real breaks; and always know when you are on a break.

Know when you are on a break

If you are building a chair its pretty obvious when you aren’t building the chair. Like if you look down and you aren’t in your workshop or near any wood then you probably are taking a break.

On a computer it isn’t that obvious. You can be working along and suddenly find yourself on the Wikipedia page for Ace of Base and not remember what brought you there. You were tired or hit a wall of fear or doubt or boredom and just opened up your web browser. You were on a mental break unintentionally. Instead plan your breaks ahead of time and push through these times. Use Pomodoro or whatever flavor of GTD or focus techniques that you like to keep working when you are working.

Take a Real Break

Well then what’s a real break?

The goal of a break is for you to not work for a bit and come back fresh to work more after.  Its a small investment for clarity and endurance.

A real break:

  1. Is away from the computer screen (or the loom if you work with a loom)
  2. In some way takes your mind away from the immediate.
  3. Occupies your mind in some other way.
  4. Is of a length where you can come back and keep working easily.

Away from computer screen

Your eyes get tired, your liver gets tired, everything gets tired. Time away from the screen resolves this quickly.  (Not the liver part)

Takes your mind away from immediate

I would not recommend thinking of work-related things as taking a break. Reading a technical blog while you take a break from computer programming is not as good as reading a magazine or skeet-shooting on your break. Do something different.

Occupies your mind

There is this myth that you can “veg-out” in front of the TV to unwind, but this does not really work. Working on your own is all about maintaining a productive momentum so I would recommend doing something with your mind (like reading or a puzzle or equivalent) or completely not using your mind like walking or taking a shower rather than doing something passive like TV watching.

Is of the right length

This varies per person, time of day, and moon cycle but for me this is typically 10 – 30 minutes.

With those criteria here are some examples of bad breaks:

  • Building a barn. (takes too long even with help from the other villagers)
  • Going to see all the Twilight movies. (too long; also they must be terrible)
  • Opening up a new tab and randomly growing reddit or equivalent. (does not actively engage your mind, is at computer)
  • Watching YouTube videos at random. (at computer, soul-crushing)
  • Getting into fights about stuff over the Internet. (at computer, does not occupy your mind)

Here are some example of good breaks:

  • Going for a walk.
  • Washing all the dishes in the sink.
  • Drawing a small picture of a tree with a money in it. The monkey has a telescope and is looking at you.
  • Smoking a cigarette. (unfortunately)
  • Brewing and then drinking tea.

My personal favorite technique

I am literate.


My personal favorite break technique is to read one “American-style” short story. These are typically 20 pages long and establish a character or idea in that length. They take about 30 minutes to read and completely take your mind away from whatever you are doing. I read them away from my computer but near it (sometimes it is necessary for me to keep headphones on in case there is an emergency). This technique clears all my requirements above and has lead me to read all sorts of great stories. By the time I’m done I am “back”, my mind and eyes are rested, and I am ready to work.

*I know that the term “veg-out” means act-like-a-vegetable and not move, but it blocks the term from being used when you eat a huge salad.  Barbecue Ribs don’t move either, it should be “Rib-out” because they don’t move and you don’t move after them.

I’m writing a book about successfully working from home; click here if you want to know when it is complete.

Sacred Space: Building the Energy of your Home Office

In a previous entry I mentioned that you should have certain infrastructure readily-available when you work from home. After I wrote it this idea kept bouncing around my head that is a lot more important: how you treat your home office.

What you don’t do in your home office and what you don’t have in there matters more. You can’t just pull up a fold-up chair to a coffee table and get real work done over the long-term from home. You have to create a Sacred Space.


To pull off working alone and to build anything of any real value you should treat yourself as a professional and respect your work for its intrinsic value. Take it seriously and build a space that shows this attitude.

Don’t eat at your desk. Don’t browse YouTube aimlessly at your desk. Take a break at a separate desk or computer; the space for work is for work only. Don’t allow your kids into your office unless they are there to make something. When they make something put it up on the wall. The smell, energy, and feel of the place is that of doing stuff, making stuff. It helps your muscle memory when a space is always used for the same purpose.

This of course means that you probably won’t be sitting at your desk for 8 hours a day. The time you aren’t working you shouldn’t be in there. Run your online errands elsewhere; check your news elsewhere.

Design your space

Your office should be highly-functional but pleasant. You should be in  direct control of noise and interruptions as much as possible (door that shuts is a minimum, steel door that shuts is better, sound-dampening room with a parachute catapult for quick exits is ideal).

Your office should be treated seriously but it should be a place that you want to spend time. Work is hard sometimes. When you look up from your computer to think  you should enjoy the fact that you don’t have to look at sad greyish-brown-really-man-oh-man cubicle walls or generic ‘art’ and the smell of sad coffee stains soaked into the walls of a typical office space. Put up some Teenage Mutant Ninja Turtle posters. Have toys, write something on your wall. Buy some ZenPencils posters. Have something that you want to look at; change it often.

As an illustration of this concept the below are some videos of professionals showing the rules of their spaces:

Casey Neistat: Red Boxes

Tom Sachs: Sacred Space

I’m writing a book about successfully working from home; click here if you want to know when it is complete.

Work Life Harmony & Resistance

We recently did a home refactoring project to make it better fit our family as it exists now with some new requirements (two kids and one work from home Dad more than originally anticipated).

The core idea was to create a completely separate work space for me that could operate independently from the family life while still be near it – sort of like a small guest house. We considered: soundproofing my office, moving it upstairs, shifting some rooms and wall configurations to allow secret access to a bathroom, and building an astronaut helmet for me so that I was in a quieter space and away from our 87 children aka entropy amplifiers.

At the last minute I decided against it – not because of price or effort or how disruptive it would be. I chose to leave my office as it is now because the reality of working from home for this long is that I’m no longer trying to strike a work/home balance or separation but instead a work/home harmony.

All these terms are completely overloaded. In a job interview people always ask about work/home/life “balance” and whether a company supports it. The idea is that if you have balance in your work vs. home life you won’t miss your family’s important events. No last minute weekend work or 90 hours a week expectations. The marker of whether or not you have work/life balance is whether your significant other* sort of hates your boss. In reality the work side typically wins in this “balance” anyway:

Every one of us has learned how to send emails on Sunday night. But how many of us know how to go a movie on Monday afternoon. You’ve unbalanced your life without balancing it with someone else. – Ricardo Semler

The old success model was that the wealthy could completely separate work from home. Subway ride to Manhattan, secretary to manage work errands, home life miles away. Or constant business travel – first class around the world away from home cashing big checks and eating buttery dinners at steakhouses with people you don’t really know.

The new success model is to have work come to you rather than you travel to work. In the most boring scenario you work from home and you are near your family. A more exciting version is that you take your family with you and travel around the world working. An even more exciting version is that you work blind-folded using only an old Android tablet whilst riding a bull as you dodge bullets and manage to install a Java update without ruining your computer as your kids cheer you on from galloping recently-broken wild horses as your wife sprays shotgun fire at your enemies.

I don’t want separation of who I am into different arenas. I want my work life to be an extension of who I am just as my family life is – something to be proud of and work very hard at and fill with humor and love and creativity. I want my kid’s creativity to spill into my work life and my work to be understood by them.  I would love to have a small desk in my office where my kids could do their homework; my ideal coworking space would be me and my family, a $4,000 espresso machine, and a barista that speaks in the voice of Shredder from TMNT.

I don’t have all the answers on how to accomplish the sort of deeply-focused highly organized work that my job requires while in the same house with my kids, but I know that I can’t avoid the problem to solve it.

In The War of Art Pressfield talks about resistance – the idea that any good work will be worked against by outside forces. It’s quite a spiritual idea to some and to others is a physical manifestation of our need to procrastinate on the important things. In any event in my work life I’ve found that the more I gain control over my working parameters the more resistance I face.

Imagine this: the absolute ideal for getting a lot of work done is to have a private island accessible only by your boat that is stocked with food and water and clothes freshly cleaned and dropped daily via helicopter.  Your Internet connection is wicked fast but only allows sites relevant to your work; the temperature is perfect inside and out; your devices do not need charging; your bills are paid, Wild Berry Skittles grow from the ground like weeds, etc.  You are freed from all things but the work.  Any person who has worked alone knows that this scenario would, after a few days or weeks, find us waxing that boat or organizing the driftwood or climbing the palm trees rather than working.  We are not made for these isolation chamber existences and such deep unwavering focus and our minds object and we face resistance.

So we have to build-in and control our resistance. And given the choice between any other distraction and my family I’ll take my family every time.

* Or cat or lizard.