Planning for the year ahead Jan 10, 2016 - 1 Comment

Last year, I set 12 goals for myself in 2015. That was a lot of different stuff to focus on, and I learned a lot from that experience. This year, I’m taking a different approach by setting a few broad objectives, building habits that feed into those objectives, and applying some of the advice I’ve gathered on this process over the year.

Broad Objectives

Rather than many different specific goals, I’m focusing on a smaller group of broader objectives, similar to OKRs. The intent here is to draw a sketch of where I want to go and cultivate the behaviours that will get me there.

Why not goals? Because goals suck - they’re rigid, unchanging and your default state is being incomplete. Habits, on the other hand, are flexible and make you focus on the process, the here and now, allowing you to appreciate the journey. 

The comparison between habits and goals is similar to the concept of optionality from Antifragile. Goals are teleological, “the illusion that you know exactly where you are going”. The book compares the teleological tourist to the optional wanderer, who “makes a decision at every step to revise his schedule, so he can imbibe things based on new information … the flâneur [wanderer] is not a prisoner of a plan”. One of my main learnings from setting goals last year was that they were rigid, and required constant revision. Without revision, they became irrelevant and much easier to ignore.

I’m modelling my approach after the wanderer, only providing general directions:

    1. Be connected to people
    2. Be active and healthy
    3. Enjoy mornings
    4. Read to lead
    5. Don’t be an asshole
    6. Be intentional with how I spend my time
    7. Learn to tell stories and write

Many of these are interconnected - being connected to people is part of not being an asshole; reading to lead is part of being intentional with my time - and they’re all focused on improving my overall quality of life. The one thing these goals aren’t, is SMART, that benchmark method of setting goals. These aren’t specific, directly measurable, etc. And that’s very much intentional. They’re directional goals with habits, and they use behaviours that feed into them. 

Feeder Habits

My approach this year will be to keep these high-level goals as reference points, but break them down into smaller habits that I can focus on day-to-day, and feed into my overall goals.

Lets take the example of being active and healthy. That’s the truest expression of what I’m looking to accomplish, and I don’t want to compromise on that. But in order for it to be attainable, and to get my brain to buy in, I’m going to have to break it down into a smaller, more attainable representation.

One part of being active and healthy is exercising more. The full-blown habit would be exercising for an hour, 5 days a week. The small feeder habit that I can build is one exercise every day. By itself, that’s not going to transform my life, but it’s creating a habit around regular exercise, which is the most important thing. I’m focusing on the foundation of a long term shift to bring exercise into my life. It will be far easier to increase to an hour every day if I’m already making space in my life for the habit.

The approach here is modelled after Tiny Habits by BJ Fogg, and Leo Babauta’s explanation of the method, both of which I highly recommend looking into. The Tiny Habits model takes this feeder habit idea a step further, suggesting that the habits should be broken down as small as possible. In this case, my exercise goal could be broken down into doing a single push up each day. I don't want to go quite that small scale, but it's an extremely handy tool to have at your disposal for the more difficult habits.

Tipping Points

The idea of small feeder habits also connects to the idea of tipping points. The point where your brain shifts from being pessimistic and making excuses (“that’s way too hard”, “just watch tv instead”) to being bought in and motivated to complete the behaviour you’ve set out to accomplish. 

This tipping point is called the Zeigarnik Effect as outlined by Mikael Cho. The Zeigarnik Effect is that quirk of the brain that hates leaving something unaccomplished, like when you have three pages left in a book and just have to push through to the end.

By starting the behaviour in some small way, you signal to your brain that it’s unfinished, pushing your mind to complete it. Just starting is often not enough, as you’ll find that there are particular points in the process where your brain makes the shift. For example, looks at all the small steps in a habit like working out. Pack a gym bag, go to the gym, change, put on shoes, stretch, etc. Just packing a gym bag is likely not enough to trigger the tipping point. But putting on your shoes may do the trick! Putting on your running shoes can send the signal to your brain that this is happening, and it needs to keep pushing until it’s complete. 

When you’re looking at a new habit, break the process into it’s individual parts and look for the point where your internal dialogue shifts to “let’s do this!”.

Build on Success

Another advantage of the Tiny Habits approach is that it helps you start small and build on success. I want to avoid what happened last year, where my attention was so divided that I never truly focused on any one goal. 

"Building a single habit at a time and focusing all my energy on it until it’s truly an ingrained behaviour is the best way I’ve found for solidifying a habit and ensuring I’ll be able to stick with it even when I’m not feeling great” - Belle Cooper

The intention is to narrow my focus to specific actions that feed into my larger goals, and use these tiny habits as a foundation. Start small, and build on success. When I’m comfortable with a habit, then I’ll start looking at new ones that I want to add without worrying about the established habits falling to the side.

An example of this would be the goal “Be active and healthy”. If I try that all at once, I can guarantee you it will fail. Instead, I can focus on specific areas of this goal one at a time, starting with a single exercise and flossing, then adding 15 minutes of exercise and mindfulness, then adding regular walks, and so on. If you stop and think about it, it’s odd that we would ever approach things in the all-or-nothing attitude of resolutions. “I’m going to be active and healthy starting now by doing 15 new things”. Good luck! Build on success - the habits don’t lead to a new life, they are your new life.

Habit Stacking

One of the most impactful pieces of advice I’ve come across for building habits is the idea of stacking new habits on existing ones. I first came across it from Belle Cooper (to whom I owe much of my understanding around habits), and then a detailed explanation by James Clear which introduced the idea of synaptic pruning. 

The core of the idea is that our brains have strong, existing paths for habits we currently practice. For example, if I play the piano every day, my brain will have strong paths for that habit, but weak ones for a habit I’m building like exercising. In order to be more successful with new habits then, leverage the strong connections by using existing habits as triggers.

For example, if I want to build the habit of exercising, I can stack it onto my morning coffee. Before my coffee or while it’s brewing, do one exercise. I’ve begun sketching out what this will look like for each of my habits, beginning with my existing daily habits and then matching those that I want to develop. The goal is to leverage these habits, making them act as springboards for the new ones I want to build. The opposite would be the equivalent of starting cold turkey.

Tracking Progress

Throughout the year, I’ll be tracking my progress as I build these habits. Right now I’m using HabitBull for Android (though I’d love to use Momentum, unfortunately iOS only) which is essentially a habit tracker based on Jerry Seinfeld’s “don’t break the chain” approach. The app does a few key things for me.

  • It tracks your streak, which is helpful for not going too long without sticking to the habit.
  • It has timed reminders, so I can get a reminder when it’s most applicable.
  • It gives me some accountability, if only to myself. “I forget” or “my notebook is too far” isn’t an excuse.

There are a bunch of similar apps out there, and in my experience it really doesn’t matter which you choose. The main reason I went with HabitBull is that it’s flexible, basic, and doesn’t limit the number of things you can track. The important thing is that you’re tracking your progress and being prompted to do each habit.

Why is tracking this information important? For me, it does two things. First, it forces it to the top of my mind and forces me to be intentional. Tracking has a low cognitive load once it’s set up (just a tap of your phone) and sparks intentional thinking. Second, it not only helps me stay accountable, but also motivates me. It feels good to tick off another day. It feels even better to tick off your 20th day in a row. And once you get to that point, you’ll have the mental drive to not break the streak.


Tracking is also helpful for the last part of this approach, regular reflection. Last year I shortened my feedback cycle from a year (regular resolutions) to 90 days. Well, it turns out that 90 days still doesn’t work, at least while building new habits. The mental energy to get back into the right mindset alone was enough to prevent me from sitting down to reflect sometimes.

Knowing this, and with the idea of stacking in mind, I’m shifting to monthly reviews. A habit that I’ve already built is an hour each Sunday night blocked off as “Plan the week”. Each month after one of these, I’m going to spend time reflecting on my progress. Ideally, I’ll already be in the right mindset, have time blocked off, and have a good idea of what I wanted to do that month.

I don’t have a structure in mind for the monthly review, so I’m sure it will change over time. Roughly, here are some things that I think will be helpful to look at (source of inspiration for these here and here).

  • Biggest wins/best moments?
  • Biggest learnings?
  • Status of tracked habits?
  • Main habit to focus on next month?
  • Any changes to existing habits?

The goal is to have a sense of how I’m progressing, insights on what I need to change going forward, and aspirations for the future. A good mix of positive reinforcement and pushing myself. Personally, I’m a results-oriented person, so laying out my progress in concrete terms is a big motivator for me, and helps me build a mental model of how I’m doing.


The setup and thought behind this approach took a fair bit of time, but so far the habits themselves haven’t required a lot of me. In the last four days (granted, without the stress of work) I’ve been able to maintain all of my habits and often exceed them with little effort. It’s put me in a more positive mindset, which will hopefully lead to good results in a month. I won’t be publishing my monthly reviews, as it leads to some self-censoring, but I will be writing about them on my own and may publish any lessons learned. If you end up trying any of this, I'd love to hear about your experience!