You may think that time management is something that only uptight business people need to worry about. You'd be wrong to assume this. It doesn't matter what your career or vocation is. You could be an elite athlete, an aspiring musician, a stay at home mother, your problem is still the same -- the days are long, the years are short, and if you don't consciously navigate towards your goals they simply won't happen.

Now it's true that the best laid plans change all the time. But the exercise of planning still helps you get where you are trying to go. In fact, a good planning system is all about course adjustments.

The danger of not periodically reviewing what you are doing is that you can spend years working in the wrong career, or staying in the wrong relationship, simply because you have no system that allows you to periodically reflect and hone your focus. I have friends who are guilty of this (by their own admission). The reality is that most people don't think regularly on a long term horizon, which is why it is such a life advantage to do so. It's easy to move forward by inertia alone.

People who set realistic goals and track progress towards them also have the side effect of being happier and more optimistic about life than people who don't.1

Ok, so on to the planning system:

Once every 90 days I write up a set of goals up on a whiteboard. I might take a whole day on a weekend to consider them. If my goal relates to getting some travel in, I'll figure out which friends or places would make the most sense to visit. If it involves working on a new prototype for a hardware project, I'll do some research and figure out what would make sense to attack over a 90 day period. I take the time to appropriately research the goals before I set them.

Over the course of 90 days, I circle the ones I'm currently focused on, and check off the ones I've completed. At the end of 90 days, I take a picture of the board, erase everything, and start from scratch. That's it. It's a simple system.

This sounds really unnecessary... I don't need to be so formal about it, and anyway I don't have trouble remembering my goals.

Good luck with that. Our memories suffer from distortion. Without some kind of interval based system, it's easy to stretch out time periods for goals indefinitely. The idea here is that it's better to fix time and flex scope than vice versa. Also, having a more formal system keeps you accountable and let's you plan holistically so you can get crazy travel stuff in AND get that professional certification. Finally, most people's intentions aren't 100% stable over a 90 day period. Writing down your goals helps you refocus.

Why a whiteboard?

I've tried keeping this on a computer, or on paper... These don't work for me at least. I lose interest in them. There is something about passively walking by a board on a wall and physically seeing carefully set goals that creates a kind of 'animal spirits' motivation to get them done. It's the difference between a photo stored on your computer somewhere and a photo hung up on your wall.

Why 90 days?

When I first started formally setting and tracking goals, I started with 2 week intervals. Later I tried 1 week intervals. Later I tried setting goals for each day. None of these worked for me. I find that when I shorten the time interval too much, the ambition of my goals shrink dramatically. It gets worse the smaller the interval.

Goals should be about achieving major life ambitions, like running a marathon. In a 90 period you can make significant progress on almost any major life goal (or realize after putting in real effort that maybe it's not a worthy ambition after all).

When I planned on shorter intervals, things like doing laundry made its way onto my list, which isn't the sort of thing I'm trying to track with this system.

It's true that large projects slip one day at a time, and for some people there is value in tracking progress at the day to day level. But I personally found that the time and overhead involved in tracking goals every day wasn't really worth it. Your mileage may vary though, try out different intervals and see what works for you.

What sort of goals do you set?

Anything and everything goes on this list. Objectives for my company. Trips to visit friends. Running events. Reading lists. You name it.

What happens if you don't finish stuff on your list?

Nothing happens. I just try to get better about creating a more realistic list next time. When I first started, I was pretty bad at estimating what I could actually get done in 90 days. I've since gotten much better.

If I still want to finish goals that I didn't get to, I'll just put them in my list for the following quarter. Sometimes though, I'll realize that they maybe were not worth working on at all and discard them.
Each quarter should be starting from a blank slate and considering what's important.

This sounds stressful... What about just having fun?

I used to be much more stressed out when I didn't do this, because I was worse about juggling my existing responsibilities, my future ambitions, and doing stuff for fun. It's relaxing for me to know that I've already thought through everything - both responsibilities and the fun stuff.

So on your spare time, you pick a goal from your quarterly list and work on it to the exclusion of everything else?

Yeah, mostly. I have some slack if I want to do other stuff, but mostly I try to focus. Remember that I have recreational stuff on here too.

What about stuff that comes up randomly during the 90 day period? You can't plan for everything...

Most of the time, the sorts of things that come up don't have any particular date attached to them. I might read an article about the Seattle tech scene and think to myself that I should really make a trip out there. So for stuff like this I make a note of it and keep it on the backburner. When the quarter ends, I look at my backburner list and also think about new things that I'd like to get done in 90 days. If whatever the thing is that comes up is really important, eventually it will get done. I have stuff from a year ago or so that I kept on my backburner, ignored for several quarters but am finally checking off now.

If stuff comes up that is time dependent, like a business opportunity or a music festival or something, I'm not overly rigid. Sometimes I'll drop what I'm doing for the opportunity. Most of the time I don't do that though.

How do you know which goals to set?

I don't. This is the hardest part, because 80% of my results come from maybe 20% of my goals. The 80/20 rule unfortunately only works in hindsight. Setting the right blend of ambitious and realistic goals is the hardest part.

Didn't you say there was no special system? Why is yours any better than anyone else's?

My system isn't better than anyone else's. But planning and executing a set of formal goals on some type of pre-defined interval system set is better than just winging it or going with the flow. I think the most effective people are good at ruthlessly focusing on just a few things for a long period of time.

Yeah, that's pretty much it, so get to work.

1 The How of Happiness - Sonia Lyubomirsky

There's a famous story from Stephen Covey's book, First Things First 1 that goes something like this:

A professor is giving a lecture to a class and holds up an empty bucket. He shows the bucket to the class and asks if it is full. The students, thinking this is some silly exercise, all chime in unison, "No."

He then gets out a bunch of large fist-sized rocks and drops them into the bucket one by one, until no more will fit inside the bucket. He asks, "Is the bucket full now?" "Yes" - chime the students.

The professor smiles; he pulls out a large jar of sand from underneath his desk and proceeds to pour it into the bucket. The tiny particles of sand fill the spaces in between the large rocks. The professor shakes around the bucket until the sand settles, and continues to pour the sand in until the sand is level with the top of the bucket. He asks again, "Is it full now?". Sensing that there is more to this, the students are silent. One student reluctantly says "Yes, the bucket is definitely full now."

The professor says nothing; this time he pulls out a jar of water from underneath his desk and slowly pours some of the water in to the bucket. At first the water pools up on the top, but it slowly seeps into the sand, filling in the tiny air pockets between the individual particles. He continue to pour water until finally a thin layer of water remains on top of the sand at the very top of the bucket. The students say nothing.

"What was the point of this exercise?" the professor asks.
"The bucket is never full!"
"You can always cram in more!"
"Don't be overconfident!"

"No, the point is that if you don't start with the large rocks, you'll never get them in."

The bucket is of course an analogy for life. And the large rocks are large goals or priorities. What Stephen Covey is saying is that you've got to prioritize the big stuff first or it will get drowned in all of the small, day to day things represented by sand and water.

But I think he only gets this analogy half right. I think the analogy is more like this...

We all start with an empty bucket in life, but from the moment we are born, like an hourglass, there is always sand trickling into the bucket. And unless you have a system for actively dealing with that sand, you'll soon get overwhelmed.

Assuming you live in a developed country, there are inescapable responsibilities that come up - things like paying bills, car maintenance, getting a medical and dental checkup each year, checking your insurance coverage every so often, etc. You don't necessarily have to do all of these things, but you will almost certainly regret not doing them after some time. Car maintenance is 'sand' up until the point when your car breaks down. Then it's a huge fist-sized rock. That dental checkup? What should have been a routine cleaning, became a cavity. The point is if you don't pre-emptively deal with the logistical crap that constantly trickles into your bucket, in most cases it will only consume more time and effort later.

So the way I think about it, it's best to have a system that constantly tosses the sand out of your bucket. Ideally, you've given some thought to what all of these logistical things you have to deal with are (as opposed to the truly insignificant things) and you've automated as much of this as you can. If you can do this, then you really free up your time and energy to focus on the large rocks.

That's my goal at least.

1 I'm paraphrasing this story. The book is terrible by the way, don't buy it.

I've noticed that over a long period of time, the people that seem to get the farthest in life are the ones best able to remove the clutter and distractions of daily living, and focus at an insane level on just a few key things. 2

So how does one focus? And what are the right things to focus on?

The first question is the easier of the two to answer: Get a system in place. I've experimented with a lot of different systems... from Getting Things Done, to the 4 Hour Workweek, Personal Kanban, Pomodori Technique, etc. I've personally found that no one system works best, and that you ultimately need to blend together what works for you. My key takeaways from all of this reading:

1) Keep tasks separate from your calendar, your calendar is sacred.

2) Task lists can be short-term (today) as well as long-term (over many months or years). I get the best mileage out of planning when I think long-term, since almost no one else does it.

3) Have a separate filing system for archiving information that you may need to retrieve later. Don't mix unactionable reference information with tasks, and don't mix tasks with your calendar.

On some sort of regular interval, I plan and review goals that my calendar, task list, and archived information are all aligned to support. I use different intervals for different sorts of goals. For life related goals, I plan in 90 day intervals. For startup stuff, I plan in 30 day intervals and also in 1 week intervals. You get the idea. The important thing is to set the goals, and keep a scorecard for the interval. And most importantly to think about how you can improve for the next interval.

The second question is much harder to answer... What to focus on?

Unless you take a fairly deliberate approach to answering this question, I think you are bound to waste a lot of time on low value tasks. The 80/20 rule is no answer to this question, because in my humble opinion, it only works in hindsight.

In Thinking Fast and Slow, Kahneman talks a lot about systematic biases in our daily actions that we are simply unaware of. We make all sorts of bad decisions when we allow our intuition (System 1) to guide our decision-making, and perform moderately better when we take our time and think deliberately (System 2). So the one thing definitely not do is to trust your intuition when it comes to answering this question.

So what should you do?

My best answer at this time is to identify Intended Outcomes for your bucket list of goals and then weight them. An Intended Outcome is a concept from Tony Ulwick's excellent book What Customer's Want and there a great white paper on the concept here.3

For example, one intended outcome that I have for this quarter under my larger goal of fitness is to run an average of at least x2.5/wk and complete a couple 10Ks. My intended outcomes are actionable, with a fairly clear criteria of success or failure in most instances. I've weighted this approximately 10 points (out of 100) for the quarter. If I'd weighted fitness higher, I might try to run x4/wk and do a couple races in the 10 mile range.

I'm paraphrasing a bit, but Kahneman makes the excellent point that without deliberation, we tend to routinely overweight small value actions, and underweight high value actions. By a lot.

The following is a table from his book. At the very low end, you'll notice a 1% possibility gets weighted as a 5.5. At the high end, a 95% possibility gets weighted at a 79.3.

For focus and time management, this a waste. Last year around this time for example, I was studying to get a few project management certifications. At the time I felt that it was very important to complete these certifications and probably let them take up a theoretical 20 points of effort. In retrospect, if I had carried out the weighting exercise, I probably would have given them 5 points. Looking back now, I probably overweighted this goal's importance to me by a factor of 4 because I went with my intuition. It wasn't clear to me what I was sacrificing by allowing this goal to absorb so much of my time.

We do best when we weight possibilities exactly what they are worth.

Is this a perfect system? No. It's definitely not. For example, even when you deliberate on a goal, how can you be sure that you are weighting it correctly? To some extent it's still a guess, but there are some things you can do to improve your weighting further in cases where it really matters.4

And planning like this definitely takes up a large chunk of time every few months, so it's important not to go overboard. But it's even worse to waste time on the wrong goals. So focus.

1 One of the best books I've read in a long time by the way.

2 You never really know though... Everyone is running a different race, and things are not always as they seem.

3 An Intended Outcome is a concept from product development. When you are planning features for a product, rather than thinking in terms of the solution, think from the customer's perspective about what they really want or need. So for example, when a customer buys a drill bit, they're not really buying a drill bit... They're buying a 1/8th inch hole in their wall.

4 Talk to other people that have currently achieved what you are thinking about doing in the future. Are they happy with their outcomes now? Get an average of 3 data points at least.