I’ve been sitting here for the past 15 minutes writing and re-writing the opening sentence to this post. At first, it sounding something like this:

Deciding is hard, precisely because there are no perfect decisions.

But this didn’t sound right. I didn’t want to jump straight into the primary thesis of the post. I needed something to lead in with, so I changed it to this:

Decision making is an emotionally draining process…

Again, no dice. Too obvious, I felt bored just typing it. I ran through 3 or 4 other variations then realised what was missing. I needed an anecdote to lead in with. A couple of ideas came to mind, but nothing seemed to fit the situation well enough. Eventually, I just started typing:

I’ve been sitting here for the past 15 minutes writing and re-writing the opening sentence…

It seemed fitting, considering the subject of the post.

Why is decision making so hard for us? The reason is that deciding inherently involves removing all other possibilities. The etymology of the word, after all, is from the Latin “to cut off”:

Decide late 14 century., “to settle a dispute,” from old-French decider, from Latin decidere “to decide, determine,” literally “to cut off”

(source)

As the result of social conditioning and our evolutionary psychology, our minds are wired to look for dichotomies in the world. We understand and process the world in terms of the “black and white”: good and bad, right and wrong, us and them, etc.

But the world isn’t like this. The world is inherently constructed of the in-betweens, the shades of gray, the non-binary probabilities.

When we make decisions we want to be “right,” whatever that means in the context of the current situation. But therein lies the problem: most decisions are made on partial information. Especially when it comes to the big decisions such as those to do with work, relationships and life, there is no guarantee that one decision will be right (let alone any real definition of what is right).

Another problem is that the outside world expects us to be consistent. Those who frequently change their minds or express uncertainty in the face of their decision making are seen as weak, lacking confidence or not having leadership capability.

So frequently we “un-decide.” Un-deciding isn’t just not making a decision: it’s not making a decision but acting like we have. Un-deciding is when instead of drawing a line in the sand and taking action, we go and ask our boss “if it’s alright.” Instead of being decisive and taking responsibility for the outcome, we defer responsibility to a higher power.

We do this because deciding is hard. Deciding involves disappointing people who don’t agree with us. It means putting in hard work with no guarantee of a pay-day. It means maybe turning out to be wrong.

But not deciding is worse. When we put off making decisions, we live half-heartedly and without conviction. We convince other people and (worse yet) sometimes ourselves that we’re being productive and working towards goals when, in reality, we’re not doing anything.

Deciding means taking responsibility and having the courage to confront being wrong, and it’s the only way to move yourself, your organisation and the human race forwards.

Can you decide?

I live for novelty. Mental curiosity about the world and other people is built into us, and is the root from which all creativity, art and innovation grows. It adds depth and texture to our lives, and should be embraced at all opportunities.

Of course novelty and interest isn’t something we need to passively wait for until it is thrust onto our laps. We can (and should) be proactive about it, seeking it out as often as we can.

Russell Davies article How to be Interesting from 2006 provides a great list of actionable items you can use today to start introducing more novelty into your life today:

1. Take at least one picture everyday. Post it to flickr.
2. Start a blog. Write at least one sentence every week.
3. Keep a scrapbook.
4. Every week, read a magazine you’ve never read before.
5. Once a month interview someone for 20 minutes, work out how to make them interesting. Podcast it.
6. Collect something.
7. Once a week sit in a coffee-shop or cafe for an hour and listen to other people’s conversations. Take notes.
8. Every month write 50 words about one piece of visual art, one piece of writing, one piece of music and one piece of film or TV. Do other art forms if you can. Blog about it.
9. Make something.
10. Read.

(Source: russelldavies.typepad.com)

Start-up sage, engineer and overall swell guy Paul Graham wrote a great article entitled “How to Lose Time and Money.” In it, he draws the similarity between losing money in bad investments and losing time in busy work (unenjoyable activities you partake in to make yourself feel ‘busy,’ even though the tasks create no real value).

His main point is that our self-correcting mental “alarms” don’t go off when we invest money poorly, because we’re not spending the money in a self-indulgent way. Because investing doesn’t provide an instant reward in the way, for example, buying a Ferrari might, we somehow manage to convince ourselves that we’re doing the right thing, even if the investment is a bad one. It’s the twisted logic of: “it hurts so it must be good for us.”

The same could be said for how we choose to spend our time. Check out this quote from him below (emphasis mine):

The most dangerous way to lose time is not to spend it having fun, but to spend it doing fake work. When you spend time having fun, you know you’re being self-indulgent. Alarms start to go off fairly quickly…

… But the same alarms don’t go off on the days when I get nothing done, because I’m doing stuff that seems, superficially, like real work. Dealing with email, for example. You do it sitting at a desk. It’s not fun. So it must be work.

This kind of thinking is a false heuristic. It’s a mental shortcut that makes it easier for us to form an opinion, but simplifies reality in the process. Correctly formed heuristics are incredibly important: they enable us to make complex decisions quickly while achieving (on average) the best possible outcome.

On the other hand, heuristics that lead to net-negative outcomes on average can be said to be “false,” and should be avoided at all costs. While both forms of heuristics simplify reality, the core difference between them is in the details they omit in this simplification. True heuristics simplify away the inconsequential; false heuristics simplify away the essential.

The dangerous thing about this particular example (like the bad investment analogue) is that we expend resources (time, money) and also experience a negative outcome (feeling overworked, being poorer). If we’d chosen better tasks / investments to spend our time / money on, we’d still spend the same amount of resources but would experience a positive outcome. We’re still “walking the same distance,” but the path we choose will lead us either to riches or ruins.

(Source: paulgraham.com)

For most people there is no clear and distinct path towards fulfilment. Of course this isn’t always the case – some people are lucky enough to fall into the life that suits them early. But for the overwhelming majority, it’s up to us to search out and discover or cut our own path through the world.

There is an incomprehensibly large number of different possible paths that we could take. Jobs that we could go for, people that we could meet, cities that we could visit or live in… It can be completely overwhelming trying to pick between them.

From what I can tell from my short time on this planet, it seems like there are three criteria that we should use when making long-term lifestyle choices.

1. Interest

Some things are just unnaturally interesting to us. We might pick up an instrument one day and just become totally enthralled with it, without having any experience or knowledge about it. Or we might pick a book off the shelf while browsing the library and end up spending an hour reading about a topic we’ve never encountered. Interest is a signal that something resonates with our personality.

2. Bliss

AKA pleasure. A lot of the time, if doing something makes you “happy,” there is some deeper reason. This isn’t true all of the time, of course – taking drugs is an excellent antithesis to this point. But think about donating to or working for charity – the majority of people who take part in charitable activities say they feel happy afterwards. Bliss implies that we’re doing something aligned with our world view.

3. Intuition

Sometimes something just feels right. I don’t believe in the supernatural, so I don’t think intuition is in any way related to “infinite intelligence” or “god” as many imply. Instead it seems that the brain is responsible for these “gut feelings,” which occur as the result of the rapid synthesis of disparate pieces information by subconscious thought processes.

There is an important addendum to this philosophy: reaching out for these things in the long-term might mean doing things in the short-term that contradict them. Want to become a doctor? You’re probably going to have to put up with years of boring lectures. The same holds for becoming a musician and having to perform tens of thousands of hours of practice. The important thing is to keep coming back to these criteria and making sure they still hold overall, despite short-term boredom, unhappiness or discomfort.

There’s already been a lot said about Steve Jobs following his death a few days ago. I would never entertain the belief that I have anything insightful or useful to add to the torrent of incredibly moving tributes released by celebrities, industry experts and friends over the past few days, so I’ll keep this short.

Personally I’d never been an explicit Mac or Jobs worshipper. I always admired what Jobs had done in terms of building such a successful company while maintaining such stringent idealism about the quality and marketing of Apple products. But it wasn’t until his passing on Wednesday that it struck me just how much of an inspiration he had been – directly and indirectly – to anyone trying to cut an unconventional path through the world.

It’s been passed around the Internet millions of times prior to and after his death, but his Stanford address is the perfect example of this. One of the most powerful, and (at least to me) meaningful sections of his speech:

“… all external expectations, all pride, all fear of embarrassment or failure, these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already NAKED. There is NO REASON NOT to follow your heart. Your time is limited so don’t waste it living someone else’s life.”

We’re all on borrowed time, the clock is ticking. Very soon we, along with everyone we know, will disappear. The spark of our thought will slowly dissipate, all will fade to black and our bodies will return to the dust. The worst thing that can happen to you, death, is inevitable.

In the context of this truth, you have absolutely nothing to fear. You’re already completely naked. Nothing can help you – but then nothing can hurt you either.

You’re all-in, whether you want to be or not. But the real question: are you playing like you’re all-in?

Thank you Steve. You’ll be missed.