How to make decisions, stick with them, and be productive

The list of new technologies I want to learn about grows every day. My Amazon wish list contains hundreds of books on more than a dozen subjects, ranging from Machine Learning to Public Speaking. I have a spreadsheet with over 50 business ideas and associated research. Some I briefly started working on, only to abandon them a few weeks later and move on to the next shiny thing.

What the hell am I doing?

We live in a world of unlimited opportunity. But deciding how to spend our time is becoming increasingly difficult. There are so many choices. How do we pick the best one? Which metric do we use to define best?  And once we’ve made a decision, how can we follow through and avoid getting distracted? I often feel paralyzed. I am scared that whatever choice I make is suboptimal and may lead to misery down the road.

I’ve always admired people who can set their sight on a goal and follow through without getting distracted by other opportunities. I have a couple of friends who are like that. How are some people so incredibly productive? And why do some people feel empty even though they’ve achieved huge success? I figured that learning about human motivation may help me solve my problem. So that’s what I did and what this post is about.

I have’t found one answer that applies to all situations but I thought it would be good share what I’ve learned nonetheless. So this post is a collection of ideas and techniques that helped me become more motivated and productive. Not all of them may work for you. Everyone faces unique challenges after all.

Before diving into the practical stuff let’s try break down our problem. I think there are two subproblems:

  1. How do we decide what to spend our time on?
  2. Once we decided, how do we stick with our decision and become more productive?

Of course, these two problems are interrelated. Picking a project we’re passionate about may lead to increased productivity down the road. And knowing why we do something helps us sticking with it and ignore distractions. Still, I think it’s useful to consider these two question separately.

How do we decide what to spend our time on?

Don’t follow your passion

Successful people will tell you that they love what they do. There clearly is a correlation, but nobody has been able to prove a causation. Don’t confuse the two. In other words, these people didn’t go into deep introspection, figure out what they were passionate about, and then became successful because of that. They learned to love what they were doing. There’s a good chance that you are passionate about what you’re already good it. Because that’s the reason you became good at it in the first place.

Ben Horowitz recently gave a speech at Columbia University about this. Two points that stood out to me are that  passions hard to prioritize and that passions change. Are you more passionate about math or engineering? Are you more passionate about history or literature? What you’re passionate about now may not be the same thing you’re passionate about in 10 years.

In his book So Good They Can’t Ignore You Cal Newport, a computer science professor and the author of the popular Study Hacks blog, suggests looking are your strengths to figure out what you can offer to the world. What are you uniquely destined to do? Passion will be the side effect.

Follow Resistance

If you haven’t read Steven Pressfield’s The War of Art you should. Out of all the resources in this post it’s probably the one that has had the biggest impact on me. The basic idea is that a force called Resistance is trying to prevent us from doing meaningful things in our life. It’s not a scientifically rigorous theory, but a very helpful metaphor to think about human motivation.

Any act that rejects immediate gratification in favor of long-term growth, health, or integrity. Or, expressed another way, any act that derives from our higher nature instead of our lower. Any of these will elicit Resistance.

Goals that commonly evoke resistance include dieting, exercising, starting a business, and creative work like writing or drawing. Resistance is stronger the more meaningful the project is. That sucks, right? Nope, actually it’s great. It allows you to use resistance as a compass. The project you’re most scared about, the one that has been on your list forever, is probably the most fulfilling thing you can do.

I’ll talk a bit more about how Resistance manifests itself later in the post.

Be optimistic and have a bias towards action

When I read the biographies of successful people (Getting There: A Book of Mentors is a good resource) it stood out to me that many zig-zagged through their lives and made drastic career changes several times. It’s important to realize that the decisions you make are not set in stone. It’s usually impossible to determine the best path in advance. You’re better off making a well-informed decision quickly than to overanalyze the situation and do nothing. This is also known as Satisficing. Picking a strategy that achieves a minimum threshold of “goodness” often leads to better outcomes than spending a huge amount of time to finding optimal decision.

One thing to be aware of is that we tend to overestimate the potential downsides of our decisions because we’re naturally loss-averse. We’re  scared to lose our comfort and safety. In reality there are few career choices that will completely ruin your life. There’s almost always a way to recover. Look at upside opportunity instead of downside risk and be optimistic about uncertainty. If an opportunity has a lot of uncertainty (an entrepreneurial venture for example) you are certain to learn a lot from it, even if it doesn’t work out.

Inaction is often riskier than we think. A good example are supposedly stable jobs. They are stable until they aren’t. A market crash, legal dispute or shareholder issues can lead to layoffs that nobody expected. Relying on the stability of your job is riskier than continuously reinventing yourself (e.g. by developing skills currently in demand or switching jobs) and diversifying your activities.

Death

Most of us ignore death. It’s not something we typically think about. We act as if we are in this world forever. That just isn’t true. All of us will die eventually. Once we let death enter our life everything changes.

The moment a person learns he’s got terminal cancer, a profound shift takes place in his psyche. At one stroke in the doctor’s office he becomes aware of what really matters to him. Things that sixty seconds earlier had seemed all-important suddenly appear meaningless, while people and concerns that he had till then dismissed at once take on supreme importance. What about that gift he had for music? What became of the passion he once felt to work with the sick and the homeless? Why do these unlived lives return now with such power and poignancy?

Steve jobs shares a similar experience in his graduation speech at Stanford. Remembering that he’ll be dead soon helped him forget about external expectation, pride, and fear of embarrassment, and figure out what’s important to him. One of the biggest regrets of the dying is “I wish I’d had the courage to live a life true to myself, not the life others expected of me”. Regularly thinking about death is a useful technique that may help us get closer to that.

How do we stick with our decisions and become more productive?

Label Your Enemy

Resistance (as described in the War of Art) manifests itself in many forms: Self-doubt, fear of public evaluation, rationalization, or fantasizing about the outcome of your decisions. My personal favorite is rationalization:

Rationalization is Resistance’s right-hand man. Its job is to keep us from feeling the shame we would feel if we truly faced what cowards we are for not doing our work.

Simply understanding what forms of resistance we experience is helpful. Next time you experience any of the above try to identify and label it. This is also known as affect labeling and has long been used in meditation to manage negative emotions. By noticing “I am rationalizing my behavior right now” you may just be able to get rid of your feeling. Actually noticing a specific feeling when it arises is difficult, often you’re just “swept away” by it, but you get better at it with practice.

Time Blocking and Pomodoro

Time blocking is a technique that has had a huge impact on my productivity. The basic idea is that you divide your day into fixed chunks of time and assign tasks to them. During each block you work on nothing else but the task at hand. If you finish your task early you can work on a secondary task. If you don’t finish within the allotted time you can reschedule your existing blocks or continue tomorrow. It’s important that you evaluate your day based on how well you adhere to your blocks, not based on how many tasks you finish. Cal Newport describes this technique in more detail on bis blog. A side effect of time blocking is that it helps you build habits by using the same block structure every day.

Directly related to time blocking is Parkinson’s Law:

Work expands so as to fill the time available for its completion.

By assigning work to discrete time slots you are forcing yourself to be more productive and cut down on unnecessary actions.

If you have trouble staying focused for a full-time block you can break it down into 25-minute intervals with little breaks in between. These are also known as Pomodoros.

Mastery

Autonomy, Mastery and Purpose. According to Daniel Pink’s Drive these are the three pillars of intrinsic motivation. Most of us already have autonomy and I talked about purpose in the first part of this post. But what about Mastery?

Mastery is the feeling of progression, the feeling that your skills are improving. In video games Mastery often takes on the form of levels, ranks or better items. It’s one element that makes games so addictive. But how do we implement this in our own lives?

In order to gain a sense of mastery from your actions you need to set measurable goals. I like to use Google’s OKR system for this. (Okay it wasn’t invented by Google but at least they made it popular). OKR stands for Objectives and Key Results. An objective is something like “Lose 10 pounds” and its associated key results could be “Go to the gym 15 times for at least one hour” and “Run a total of 50 miles”. Key Results are always fully quantifiable.

An important characteristic of OKRs is that they are ambitious. Achieving 60 to 70% of an Objective at the end of a period is what you’re aiming for.

If you get 100%, you’re not crushing it, you’re sandbagging.

I use a spreadsheet to manage my personal OKRs. I review and update their progress once a week and create new OKRs at the end of each month. The OKRs feed directly into my time blocking schedule. Every time block is related to a Key Result.

Building Habits

According to Power of Habit up to 40% of our waking life may be dictated by habits. During these times we’re on autopilot. Habits are hard to change. This is both good and bad. Once you’ve created a habit of going to the gym every day it’s difficult to break it. But when you’re in the middle of doing your work and somehow end up on Facebook without realizing it, that’s a habit too.

Habits are made up of a cue/trigger, behavior and reward. The reward satisfies some kind of craving you have. It could be hunger, the need for socialization, or boredom. To get rid of a bad habit you can use the following procedure:

  1. Identify the behavior, e.g. visiting Facebook. This is the easiest part because it’s usually obvious.
  2. Experiment with various rewards to figure out your craving. What if you went for a walk instead? What if you listened to music for a few minutes? Does that satisfy you?
  3. Try to identify the cue. It could be location, time, emotional state, other people, preceding action or something else.
  4. Make a new plan based on your cue and try to replace your habit. E.g. “At 3pm listen to music for 5 minutes.” Write it down and follow your plan when you experience the cue next time.

Mindfulness

Regular meditation practice can help with various aspects of productivity. It can help you stay focused for longer periods of time. It will also help you to identify feelings and thoughts (e.g. rationalization) you may not notice otherwise. If you’re looking for an easy way to get started with meditation I recommend the Headspace app.

If you made it this far, thanks for reading. What are your favorite techniques for staying motivated and productive?