Digital vs. Paper To-Do Lists

Photo by Trent Erwin on Unsplash

I suspect that there is a correlation between the type of person someone is and the way they keep track of their to-dos. The most organized person you know is probably that way for a reason–they keep track of everything they do in an orderly fashion that perfectly integrates with their life. The least organized person you know might keep track of their to-dos in their email inbox and on scraps of paper buried on their desk, countertops, and the back seat of their car.

There is no right or wrong way to handle a to-do list. Rather there is but it is on an individual basis. There is the right way for you to handle your to-do list and the right way for me to handle my to-do list.

I just haven’t found the right to-do list method for me yet.

Like a lot of people interested in increasing productivity, I sometimes get distracted by blog articles (not unlike this one) that explore ways to do more in less time. Because the sheer variety and volume of things that each of us has to do would require a million monkey typing on a million typewriters to cover, blog posts often focus on the lower hanging fruit of how best to keep track of all the things we have to do. This is one of those.

Digital to-do lists are inherently stressful particularly if you are always connected.

The not uncommon issue I have is that I am overwhelmed by the number of things I have to do. It is manageable on days where I am able to focus and check items off of my to-do list. It can be suffocating on days where interruptions are coming at me left and right and it seems as if my business and personal life are conspiring against me. On those days no matter what I do I cannot seem to get anything done–certainly nothing of substance–and my stress level increases which manifests itself in negative ways.

What furthers the stress is the fact that I am tracking my to-dos in so many places. Currently, I have them in:

  • Asana
  • Trello
  • Jira
  • Evernote
  • Gmail inbox
  • Outlook inbox
  • Outlook Tasks
  • Two notebooks
  • My head

I’m not fully utilizing Getting Things Done but I am pretty good about getting things I need to do out of my head and into a to-do list so the last place (my head) does not store that many things. However, the rest of them always seem to be filled to the brim.

Lately, it has occurred to me that the number of to-do lists I have is not my only problem. I am beginning to think that the medium for them is part of the problem as well as that digital to-do lists are inherently stressful particularly if you are always connected. Perhaps the medium in which you do your work (and which you communicate) is best kept separate from where you record your tasks and thoughts.

Due to this thought process, I am going to read the book on Bullet Journaling and give it a try. I am not going to be able to fully escape some of my to-do lists (give up email? Not a chance!) but my hope is that the bullet journalling process forces me to organize my to-dos better, and more importantly, prioritize them better–which is the true challenge when it comes to juggling multiple lists.

Ultimately I imagine there is a balance in managing tasks between digital and offline methods. I suspect that I’ll use a digital catch-all (maybe I’ll revisit the way I use Evernote) along with an offline to-do list. If I can reduce the number of places that to-dos are stored, as well as do a better job of identifying what is a task versus what is an idea, then I imagine I’ll reduce my stress and reclaim some of the focus that is lost with context switching and the feeling of to-do list dread.

Principles by Ray Dalio

(This is one of a series of posts about productivity books and the lessons I took from them. The series is: Getting Things Done, A Sense of Urgency, The ONE Thing, and Principles.)

Cover of Principles by Ray Dalio

This book, Principles by Ray Dalio, has to be one of the most recommended business books of the last decade. Even before it was released in book form (it existed as a shorter, downloadable PDF on the Bridgewater website for years) I would hear business and entrepreneurial podcasters recommend it as often as they would How to Win Friends and Influence People, Mastering the Rockefeller Habits, Getting Things Done, and the more recent The ONE Thing. Having read it I now understand why. Principles is a hard (and long) read but that is because it is packed densely with actionable insights.

Where other books get their point across in a chapter and then pad the rest of the book rehashing the point in various ways, Principles covers a wide range of topics over its nearly six hundred pages. The subjects include, but are far from limited to, relationships, happiness, productivity, project management, people management, career development, goals, success, and investing. Dalio weaves what could easily be a series of self-help books into a single one using the theme of principles.

“Principles are fundamental truths that serve as the foundations for behavior that gets you what you want out of life. They can be applied again and again in similar situations to help you achieve your goals.”

Principles by Ray Dalio

What Ray Dalio has done is establish a set of principles by which he runs his life and business. Think of them as a set of guidelines that he has developed over time that govern how he handles any decision he has to make. In business (and in life) there are situations that come up more than once such as when and who to hire, when and who to fire, what goals should be pursued, what projects to greenlight, and, particularly for Bridgewater, whether or not to make an investment. Dalio has spent his professional career documenting his thinking about each of these decisions and creating systems and processes to help. When he is faced with those decisions now he spends less time pondering each decision as he sticks the relevant details into his decision matrix and is confident that his system will guide him to the correct decision.

He thinks of the world as a set of machines where with a given set of inputs being fed into the machine you can expect a certain set of outputs. The global economy is one machine made up of billions of smaller machines (national economies, corporations, departments within corporations, teams with departments, your personal job functions). It can be hard to improve on systems when you are knee-deep in the mud so he recommends taking a higher-level (30,000 foot) view which allows you more objectivity.

In order for him to gather the data he uses to build the machine in his control there are two things he espouses in order to achieve that:

  1. Be radically open-minded
  2. Be radically transparent

There is little to no gray area with those. They are core principles by which he lives his life and by which his business operates. They affect all of his relationships and, due to them, they provide him with the information he needs to guide himself and his business in ways that help him achieve his goals.

“Idea Meritocracy = Radical Truth + Radical Transparency + Believability-Weighted Decision Making.”

Principles by Ray Dalio

Another core tenet of his business is that it operates as an idea meritocracy. That ensures that the best ideas are used regardless of who in the organization comes up with them. However, while all ideas can have merit they do need to be weighted based on expertise. Anyone can have them but when making decisions you need to weigh the opinion of the subject-matter expert more heavily.

Dalio also discusses identifying patterns as part of a higher-level view of your life and business:

“Higher-level thinking gives you the ability to study and influence the cause-effect relationships at play in your life and use them to get the outcomes you want.”

Principles by Ray Dalio

When looking at something from a distance using the higher-level viewing exercise you begin to see the patterns that show what each machines’ output is. You can use those patterns as data points for formulating tests to improve your machines’ outputs. 

To extend the thought process of improving outcomes Dalio provides a framework for identifying what problems are causing bad outcomes. Usually what you identify as the cause is actually a symptom of the root cause which you have to dig deeper for. The process is somewhat similar to the Five Whys. An example might be the problem of unhappy customers. The problem might be with the quality of service your company provides or maybe the marketing or sales team has misrepresented what the service is and leads to your clients having expectations about the service that differ from what the service team thought they were providing. If the sales time is identified as where this disconnect is happening is it because their training did not adequately prepare them or is it because their pay structure incentivizes them to be less than completely truthful? This exercise provides some hard truths about systemic problems in organizations that, if they are not addressed, will have large repercussions over time.

In order to combat those problems one needs to have the best people and he spends a lot of time talking about the importance of culture and finding the best people:

“Managers will often take the people who work in their organization as a given and try to make the organization work well with them. That’s backward. Instead, they should imagine the best organization and then make sure the right people are chosen for it.”

Principles by Ray Dalio

A lot of books provide actionable advice on improving your life or business. Principles does that as well (almost too much advice as there is so much to digest) but, while those other books might provide you with insights that you can start putting into action today, much of the takeaways from the book will take months, years, and maybe decades to fully implement. He spent forty years or more building his decision-making framework and creating systems to gather the data that goes into them. This book points you in the right direction but leaves the hard work up to you.

While I think anyone would benefit from reading Principles I think those that will get the most value out of it are those that are in a corporate environment or entrepreneurs who have had some success and are past the bootstrapping stage of their business. A lot of the inefficiencies and relationships that the book addresses are ones that become increasingly common as a business scales. The solopreneur struggling to get their first customers could probably put off reading this book for a bit and instead pick up a book that will help them with their marketing or closing deals.

To reiterate, there is something for everyone in this book and I have been recommending it to colleagues constantly since I started reading it. Dalio has laid out a powerful framework that I’m thinking about almost every day. At the book’s core is something we all should aspire to:

“Make your passion and your work one and the same and do it with people you want to be with.”

Principles by Ray Dalio

The downside to Getting Things Done

Photo by nikko macaspac on Unsplash

This morning I had a thought that I found a little sad. In my life pre-entrepreneurship there would be mornings where I would wake up and think, “I’d like to finish that book I’ve been reading.” That would be my goal for the day and it would be a successful day if I spent it lying on the couch and ultimately reading the last page and closing the book for good.

I don’t have those days anymore.

The methodology of Getting Things Done has been great overall for me. In particular:

  1. Putting everything on paper (or in Asana) rather than storing in my brain
  2. Do it, delegate it, or defer it.

I never struggle to remember things anymore because I have a system in place that ensures I never forget anything.

However, omniscience is also a curse. Knowing everything you need to do is a weight unto itself and does not lend itself to spontaneity, creativity, or relaxation. It has put me into a state of feeling that I need to be doing the most productive thing with every minute of my day with no time for recharging.

I dread those morning emails from Asana reminding me of my seemingly never-ending task list.

Asana morning email

An even bigger issue than the fact that I never wake up with a day where I have nothing to do is the fact that it seems as if every day I wake needing to do more than I could possibly do. My list never gets shorter! My morning emails from Asana typically greet me with a subject line of, “You have 37 tasks due…”. Great. Just great. Never does that number drop below 36 and I think they stop counting at 50.

Let’s look at the GTD ethos of doing it, delegating it, or deferring it and revisit my list. I count seven things I can do in less than five minutes each. Let’s get those done and trim the list down to 30.

Some of these tasks are ones that I have been putting off for years and never get around to completing. Here is one I created on 5/20/17 and have since rescheduled 15 times. It is something I would still like to do someday but is not pressing (hence why I’ve put it off so many times) so I’m just going defer it indefinitely by removing the due date completely and marking for later which will keep it off of my “Today” list and off of my morning task reminder emails.

Asana rescheduling tasks

A few of these other tasks are ones that are a bit more urgent but also not ones that I need to address today. Those are getting deferred until next week or later.

What is missing from my bag of productivity tricks is delegation. I’m a one-man band at the moment and don’t have someone sitting next to me to delegate to (thankfully as the room would be a bit cramped). Until I have a (virtual) assistant I need to get better about utilizing online services such as Fiverr for accomplishing some of the simpler tasks that crop up. I had success with it a few years ago but, at some point, I started feeling as if I didn’t even have the time to write up a task and stopped using it. That has to change in order to make my busy life work.

Down to 14 tasks to do today (in Asana–let’s not talk about the lists in Trello, Jira, Evernote, and my notebook). The day is half over so I won’t get to them all but things are looking up.

So, the problem is not with Getting Things Done but with me putting too much on my plate and not being able to get it all done. Secondarily, I need to modify the Getting Things Done methodology just a bit and make a clearer distinction between ideas and tasks. Just because an idea forms in my brain (and thus needs to be jotted down) does not mean it should be added to the task list and assigned a date for completion. Those can easily be cards in Trello or notes in Evernote without a date constraint.

I am feeling more spontaneous already.

10 Productivity Tips From Hacker News

Photo by Guillaume Briard on Unsplash

“Suck it up. Stop reading blogs, stop reading HN, stop making excuses. Start working. There are no tips that will break you out of it – just self discipline.” – krschultz

This is the Nike approach to procrastination and productivity (“Just do it”). I like that the advice pulls no punches but I believe it will falter for most people in that it doesn’t reduce big projects down into small, manageable steps. Productivity is as much, if not more so, about state of mind as it is use of time.

“Work on only one thing.” – edw519

Trying to get many things done at once leads to not getting anything done in the amount of time it should take. Irrefutable logic. Additionally, and I think this is particularly important for entrepreneurs, a finished project creates value for your business while you work on the next project. For example you have two projects. Project A will take three weeks to finish and project B will take two weeks to finish. No matter what you are going to be spending five weeks getting both of the projects finished but if you work on and finish project A then it is going to be delivering value (e.g. content that adds leads to the top of your funnel, a new feature that will reduce churn, etc.) while you work the next two weeks on project B.

“Get enough sleep.” – Mz

Sacrificing sleep to meet a deadline is something that a lot of us have done countless times. For me personally I find that those late hours are at 25%-50% as productive as my morning hours the next day on a full night’s rest. So it often makes sense for me to throw in the towel in the evening and start fresh. Additionally, lack of sleep has a cumulative effect (as any young parent will tell you) so too many sleepless nights in a row will have an outsized negative effect on your productivity.

As a corollary to this, identify where in the day your most productive hours tend to be and block those off on your calendar if you can. Use the other parts for the day for the phone calls, meetings, email, etc.

Photo by rawpixel on Unsplash

“Find a team partner – and you will be cornered to start “get things done”. Otherwise, you can’t keep show up everyday without any progress.” – hwijaya

Having an accountability partner is a great practice for staying on track. Commiting to a deadline and telling someone else about it is a powerful method for driving focus and accomplishing the task in front of you. For entrepreneurs mastermind groups are often recommended and there are numerous ways to accomplish this in a corporation including what the commenter suggested.

“I write things down. I set micro-deadlines. I force myself to move on after the deadline, or if I really need to finish it, set another deadline.” – snikolov

Writing things down is the key to Getting Things Done. Get everything that is not the current task in front of you out of your head and on paper. This helps keep your mind from wandering and holding onto distracting thoughts.

“Once a week, take something you’re doing ad hoc and systematize it, or take something you’ve systemized and measure it, or take something you’ve measured and improve it, or take something you’ve improved and automate it.” – patio11

Creating processes and automating repetitive tasks is a hit on your short-term productivity but an investment towards long-term productivity and ultimately your success. This permanently takes something off your plate (note there is some time required to maintain upkeep as all processes will change over time) and opens up time every week to invest elsewhere.

Photo by Abigail Keenan on Unsplash

“Walk – Any time I am feeling distracted or stressed I take a walk outside. It reboots my mind and I come back refreshed. If something was eluding me before the walk it typically reveals itself quickly after returning from the walk.” – endswapper

This is something that I did daily for five years when I lived in a climate where I could do it year round without putting on a parka. I still try to do it as much as the weather and my schedule allow. When I get back to my desk I am much more prepared to tackle my ONE thing.

For some a mediation break might work as well but getting the fresh air and a bit of exercise really worked for me.

“What helps the most for me is just closing out all other applications, chats, and browser tabs and not reopening anything else until I’m finished with work.” – apolymatth

I’m pretty terrible about opening tabs and then not closing them for sometimes a month or two. The problem with this is that they are a continual reminder of things undone. Those chip away at your focus just like those ideas in the back of your head and things you need to remember day to day.

One thing I try to do (and still need to be better about) is taking each open browser tab at the end of the day and creating a task for it in Asana. That way I can schedule reading those webpages along with all of my other tasks. If they aren’t applicable to what I need to accomplish the next day then I’ll schedule them for next week, next month, or possibly even just close and forget them.

“Shut off social media. Kill the noise. (FB, Twitter, Snapchat, HN, $SOCIAL_MEDIA_NETWORK)” – akulbe

Social media is probably the biggest time sink of our generation. Sure it can lead to interesting new ideas and discussions but the reality is that it doesn’t make any positive material difference in your life. By making communication so simple it has lowered the level of what people share thus creating so much more noise. (If you are old enough you remember writing emails to groups of friends–or even letters–which took more effort to write. That meant you tended to not share the shape of the milk in your cappuccino or what you overheard on the bus in the morning. Still couldn’t avoid the politically motivated chain mails though.)

You would be amazed and how much time in the day is spent looking a social media feeds. Add those hours (yes, hours) up and picture what you could accomplish with that time!

Btw, for me Reddit is the killer that is not on that list.

“Love what you do. Productivity is easy when your heart is in it.” – orky56

When work doesn’t feel like work you are in a good place. This reduces the stress you feel about being productive and stress is a productivity killer. It is a vicious cycle that ensnares many employees and one that is hard to step out of. If you aren’t doing something you love you should be doing something else. (I know that is way easier said than done but you can start by mapping out a plan and taking baby steps. It might take a while–years even–but eventually you hopefully will get to a place where getting up and going to work is something you look forward to.)

Photo by Carl Heyerdahl from Unsplash and used under Creative Commons.

Productivity Powerups Course

Today I’m launching Productivity Powerups which is a free email course that will help you make the most of every hour of your day and help you achieve everything you aspire to. When you sign up you will receive one actionable strategy a day for ten days that you can implement to free yourself from the busy work that is holding you back and instead focus on the projects that will propel you forward both personally and professionally.

All this course requires is about three minutes of your day (so 30-minutes total) to read the emails. Some of the tactics laid out can be implemented immediately while others are habits that you will build over time. Time is only thing you cannot make more of so a small investment of it now will grow into personal and financial dividends that you benefit from for the rest of your life.

This course also marks a renewed focus in this blog on productivity. Our software’s goal is to save you time managing your business and our articles going forward aim to do the same.

Sign up today!