A Technique for Getting Unstuck When Working Alone

When you work alone you get stuck. Whether it be a hard problem, a heavy lunch, or just a bad interaction with resistance there are times when you find yourself in a rut and need to force your way out of it.

If there is one global law of productivity it is that of momentum: once you are working well, it is easier to keep going. Likewise, when you are in one of these ruts you have to spend extra energy to get going again.

I’d like to call out one simple technique that I used to keep momentum going and climb out of these holes: small, daily tasks.

One of these things is a secret.

This technique is simple: you have a handful of 5 – 10 minute tasks that you would love to do daily. If you get stuck, do 1-3 of these to get your mind back to making forward progress. These small tasks are not real breaks, but rather refreshers.

If I’m stuck on a hard problem I can take a break (with permission) and do 10 pushups, or go for a short walk, or meditate, or go read something. When I come back I no longer feel stuck since I was doing something, some forward motion. After the tasks are complete it is much easier to then shift the positive momentum back into the work that you need to get done.

This technique is different than the people who recommend you get up and run 10 miles and then write three pages, then work on your side project, then put another brick on the orphanage you are building.

Even on the worst of days you can find time to do a few of these. At the end of a sub-par day you can say “well at least I went for a walk and drank some water, plus those pushups”.

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

Reflection Frameworks

The week between Christmas and New Year’s Day is typically a change of pace for most people – even if they don’t go on vacation – and a socially acceptable time to reflect and make large changes in your life. I am intentional about goal-setting and have found that having a framework – a simple set of questions – to guide the reflections helps.

Here are a few ways to help you reflect on 2016 and plan for the new year.

Reflection Frameworks

#1 Todd Henry’s “Questions for 2017″

  • What do I want to experience?
  • Where do I want to go?
  • What do I want to learn?
  • How do I want to change?

#2 Agile Development Process Improvement Questions

  • What should we start doing?
  • What’s something new we should add?
  • What should we stop doing?
  • What’s something we’re doing that we don’t need to do anymore?
  • What should we continue doing?
  • What are we already doing that’s going well?

#3 “If I took it seriously” exercise

This is one I made up and use in my yearly retreats; for each role in your life (father, husband, employee, etc.) ask yourself:

What would it look like if I took this completely seriously?

This provides a good list of actions you can take to get a little better at each role, and it helps you focus and prioritize certain roles over others.

#5 Morning Journal Questions, but for the entire year.

Ask yourself the daily questions, but apply them to the entire year:

  • I am grateful for ____ [3 things].
  • What would make 2017 great? [3 things]
  • Three Amazing Things that happened in 2016. [3 things]
  • How could I have made 2016 better?

Finally, some extra inspiration and some humor about resolutions. Good luck!


Personal Pre-Mortems

If you are like me you can get into a mindset of negative thinking where you can poke holes in any potential project idea or action. After all, thinking of doomsday scenarios is a marketable skill when you actually take action to prevent them, but in our personal lives having this negative view is very bad for us. It makes us hesitate or not get started on an important project with an uncertain future. It makes us not surprised by failure or neutrality. If you expect the worst you will probably get it.

This same method of thinking can be a powerful ally, however, when used as a weapon.

Defensive Weapon

Think of an important project, relationship, or trajectory in your life. Now imagine the worst that can happen. I call this technique “pre-mortems” and it is not the most fun you will have today. Think of the following scenarios:

  • You are divorced
  • You are bankrupt
  • You have a terrible, but preventable, health issue
  • You have lost your job, and are suddenly unable to get another one in the same industry, geographic area, or market due to a damaged reputation.
  • All of your shoes have been replaced with pink crocs.

Now ask yourself this question: “How did this happen?” and list the reasons.

Well if I’m divorced it was probably because my wife and I stopped communicating, or stopped making sure that we spent time together and just focused too much on the kids, or maybe I got a wondering eye because of some unresolved problem, or because I stopped trying.

Well if I’ve got diabetes or cancer it might be because I order fried chicken from a car more times than I exercise most weeks. I guess that wouldn’t be a surprise.

If I’m bankrupt it is because I have become disabled and don’t have good coverage in that area. Since I’m the primary breadwinner and we have kids, my wife’s salary wouldn’t cover everything so we would have to lose the house.

If I can’t work in my field this is probably because some really bad scandal was slowly slipped into by a group of people encouraging or ignoring the warning signs.

If I only have pink crocs it is probably because I lost a bet of some form and am being forced to wear them as some sort of shame spectacle.

Now go and avoid those things, establish guardrails against those results, make contingency plans for those things:

  • I need to make sure I’m focusing and working on my marriage more.
  • I need to get better disability insurance.
  • I need to exercise, eat real food, and focus on my health.
  • I need to continue to avoid any financial or relational gray areas.
  • I should not bet on the New York Jets.

Now take a deep breath – none of these has happened; you still have time. During the life of a project you can apply this same mode of thinking – 60% into a software development project I can sit down and say: “OK this project is late – why?” and list three actions I could take to avoid the most common failure scenarios.

Offensive Weapon

For new projects, you can use the same method without depressing yourself. Let’s imagine something that you want to do but you keep putting it off or convincing yourself that you can’t do it. We all hear a voice that tells us “it won’t work out”, “you will fail and people will see”, “you aren’t good enough”, “your pink crocs are so dumb”, etc.

Maybe you want to write a book, try a new career path, take some time off of work to drive across the country, or audition for American Idol. Pick something you really want to do that you have talked yourself out of a few times.

Let’s listen to the inner voice, really listen for a minute. Give the little hater its chance to make a speech.

OK if you start this project and it fails, then you will have wasted $30,000, which means you would need to sell your crappy car and maybe live with your parents for awhile. As a twenty-eight-year-old man. If you are living with your parents it wouldn’t exactly be a secret, so that would be really embarrassing. Everybody that thought that you had it together would realize that you didn’t, so it would actually erode my reputation in a way that would be hard to crawl out of. From there – living in a basement – it would be really hard to recover emotionally. But I guess since you are not that special it would be what you deserve for trying to be.

Now filter out the emotions, insults, and judgments and just think of the real consequences of failure for your project. Split out how they would make you feel for a moment and just think logistically:

  • I would lose a lot of money
  • I would be spending time on something that didn’t work out, when I could have been doing other things
  • I would trade some of my reputation

Now make some plans to guard against these things being as bad – ways that you can hedge or counter these things – and list them.

  • I would lose some money, but I won’t touch a one-month emergency fund. If I got to the point that I touched this I would get a job at Starbucks. I look great in green.
  • Yes, there is an opportunity cost, but once I get started I would ignore this thought and really commit. Besides, anything else that I worked on would run into the same obstacles – I’ll be smart with the projects I pick to focus in on.
  • My reputation might get hurt, but I might also draw attention and respect for trying something bold – and perhaps I care about those people’s opinions more anyway. Besides, learning from failure means you have to actually fail sometimes.
  • Living with my parents would stink, but I wouldn’t have to do my own laundry. Plus my mom will not make fun of my pink crocs.

Now answer the inner critic with a detailed version of “So, what are you going to do about it?”:

I might fail and lose money, time, and face, but I would have really tried, and probably learned something. I would then be able to rebuild my life by taking a regular job and working to save like I have done so far in my life. Since I would have been following what I really wanted to do I wouldn’t regret it and wouldn’t feel “behind” in the years when I was re-establishing my financial stability. I would have failed doing what I want to do, rather than half-failing over the long-term doing something I didn’t care about.

Read some more about this technique at Business Insider and watch some other practical benefits to Pessimism.

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

Be A Digital Adult

Most of us reading this post are adults. We take care of those around us, hold down jobs, pay bills, shower daily and do other things that are considered mature. We avoid the struggles of children: petty conflict, biting others, and openly weeping when our bananas break.

But the world has changed and done so quickly. There are new skills to be learned, and if you don’t keep up you will continue to act like a child while those around you move forward and have to take care of your weak childish self.

Let’s learn how to be a Digital Adult – an adult in this new data-rich age run on technology:


Attention and Focus

  • Manage your email like your time is valuable. Manage all of your time as if you live in an attention economy. Don’t waste your life watching other live theirs.
  • Practice the ability to focus on actual work for long periods of time; what some call “Deep Work
  • Read things that people spent time making (like, I dunno, BOOKS), not crap like social media and celebrity gossip.

Accuracy of Information: News

You should read the news to know what is happening in the world, and not to be entertained. Read actual journalism, not things that are written as entertainment.  A good metric of this is: would the person who wrote this go to jail for a source? Also: was this “paper” around 15 years ago? Does this site seem always to print things that feel like conspiracy “we just can’t be ahead” theories?

Some things to read about this further:

Accuracy of Information: Healthcare

There is a lot of good information about our bodies and how they work online. Also, we can learn more about nutrition, fitness, and injury prevention than we have ever been able to in the past. But there are a lot of for-profit health “care” information sites that are just pushing their solution.

See the below slideshow and ask yourself if a site is driven by profit or public good.

Now, go and be an adult. Don’t let the big scary people trying to steal your allowance and energy stop you from playing and working.

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

Help with the Pomodoro Technique

The Pomodoro technique is a rare productivity tool: simple, powerful, and popular.

Years ago when I first started working by myself, I used the technique to train my mind to focus for longer periods of time; my previous job had so many interruptions I was wired for only ten minute periods of actual work. I organized my day into Pomodoros of longer and longer length to increase my endurance. It was not fun, but it worked.

While I don’t use it every day anymore, I do find myself using it to kickstart myself when things get hard. Typically, when I return from lunch I’ll set a timer to warm everything back up.

Even though the technique is dead-simple it does have some common problems for practical use at work; here is what I hear from people who have tried to use it:

I get interrupted too much at work; I can’t exactly ignore the phone.

Please don’t use Pomodoro if you are a 911 operator.

Otherwise, if you have a job where you have to respond to interruptions with great urgency then you may have to lower the “robustness” of your use of the technique, but it can still help you make the most of the time you aren’t interrupted. In this case, it might make sense to try to lower the Pomodoro time (to less than 20 minutes) so you feel yourself completing them.

For the rest of us we probably just think we have to respond when we don’t. We have been trained to respond to instant messages immediately much like we have all been trained to answer a ringing phone even if someone is right in front of us. These tasks might feel urgent, but are not typically important. If the message isn’t an emergency then ignore it or tell them “I’ll get back to you in 12 minutes”. Once you do this enough you will establish a reputation for being attentive when you do speak with someone.

To help with this you can of course simply communicate that you are using the Pomodoro Technique to get stuff done and therefore might be a bit delayed in responding to IMs. There are also ways to integrate popular messaging tools with Pomodoro tools so you can passively communicate “Do not Disturb” semantics.

If you really never have time for deep work sessions, I’d recommend just creating yourself one time for it, and to use Pomodoro only in that time:  This will keep your endurance up and allow you to keep your ‘focus muscles’ ready for those rare times when you get a few hours to work.

The 5-minute breaks are so dumb. I just check my email or look at the web – what a waste. (Or – the 5 minute breaks aren’t long enough to get a cup of coffee)

You might not be taking effective short breaks, or effective long breaks.

It is tricky because 5 minutes is hardly any time at all to some deep thinkers and too much time for the NADD among us. This will need to be closely managed at a personal level. The idea is to clear your head during the work enough that you are essentially catching your breath a bit but not getting fully out of work mode (that is what the longer breaks are for). Think “stop pedaling during a bike race as you round a large corner” rather than “get a cup of coffee and a doughnut” or “go walk the dog”. I typically stand up, squat, look out the window, take some big deep breaths then freestyle rap for a bit (you know the standard combination) and then sort of let my mind be blank and suddenly the 5 minutes is up and I sit back down.

I don’t want to stop every 25 minutes, once I get going I want to keep going.

Pomodoro doesn’t force 25 minutes as the timeframe – it is just a wise default amount of time. You can increase, as I did and many do, the amount of time for each block of work as it better fits the type of work that you do and your ability to focus. I increased from 25 minutes to 45 minutes with longer breaks; make sure these stay in a sane proportion or you will miss out of some of the benefits of the technique. You control the joystick – if you feel like you can keep going then the timer going off can simply be a reminder to stand up or rest your eyes or some other simple break. The point is long-term endurance rather than exact compliance to a technique.

This puts too much structure in my day man, I need to just ‘feel it’. I’m not a robot; I work when inspiration strikes.

This is true you are a unique snowflake – everyone knows it. Pomodoro works for multiple reasons:

  • It makes you stay in your chair.
  • Because it forces you to catalog all your interruptions it makes you focus on how much you interrupt yourself.
  • It is a form of mental interval training which is a great way to improve your focus and mental endurance.

I agree that doing it as prescribed all day is sort of nuts; I certainly don’t do this. This said, sometimes you have to turn into a robot for awhile to gain the advantages above. And to return to the objection about inspiration – let’s agree that the “work when you feel it” is clear bullshit. All people who have accomplished large works have done it by having a worker mentality that to you might look like a robot. I can’t say it better than Pablo:

La inspiración existe, pero tiene que encontrarte trabajando.

Inspiration exists but it has to find you working.

– pablo picasso

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

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.

Anyone who has attempted bold things has felt this. Try doing something timeless like raising children, starting a diet, trying to help others and 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, the 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, Seligman details “Positive Psychology” which has shown that remembering positive events, expressing gratitude, and focusing on core strengths can 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 Tim Ferris enough you will buy something.

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 [Spring 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. This period was tough 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. You can see this impatience reflected in the journal, but the question format forced me to think smaller about it.

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 night 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 the before-bed ritual 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 let me see the wins. And reminding yourself that things are overall going pretty well is a very powerful idea. 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 YouTube.com 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, espn.com, velonews.com, youtube.com, whatever-your-addiction-is.com
  • 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.