Here’s my immediate goal: to write an easy-to-read article about the downsides of planning.
The correct thing to do is to gather my facts and the points I want to make, organise them. Come to that, given that this is my personal blog, I should fit the whole thing into my priorities for this week.
Instead, here I am, just writing it. Which is how I do more things than we’re told is good.
And starting with a diversion about personality tests. If you’ve ever taken one of these, you’ll notice that one of the “dimensions” they want to measure is your “openness”, and this is something that a lot of people misinterpret.
“I’m really open-minded!” they’ll say, as the results tell them they score low on that dimension. But it’s more useful to think about it as decisiveness if you score low — people who are very “open” like to leave things open, not decide, wait and see, keep a few options on the go, wonder if something new or better might come up. Decisive people hate that, and want to be able to call things settled, even if they have to change later.
Having taken a few of these tests while at work, my experience is that decisive people are heavily represented in business life. It’s what tends to be rewarded in structured situations. The same applies to life advice, consultancy, self-help and the vast array of things around us telling us all the time what we can do better.
Decisiveness is just a personality preference
Like being left-handed, being very open is not a question of right or wrong, better or worse, it’s just a preference. In many situations decisive people feel that open people need fixing, but then introverts will tell you that extroverts treat them that way too. There is nothing about the world that makes openness inferior in itself, just, at most, that the human world is organised by people who decide things.
Planning amounts to deciding what we want the future to look like. It is a tool, useful where such future-shaping decisions are practical and desirable.
Where do you see yourself in five years?
This is a cliché of a job interview question. Mocked a lot, these days, for good reason. A majority of us don’t think of our lives in that way.
Some do, and they tend to be the people held up as examples. The sportsperson who dreamed of being the best in the world and single-mindedly made it happen. The founder who sacrificed everything to make their vision of a world-conquering business come true. The politician who did get to the position where they could change the country.
The question to ask before accepting these figures as models is whether we actually want their version of success. Many of us assume we do, because we’re meant to.
Do you want one thing enough to do without everything else? Can you pin your future happiness on it, succeed or fail? Only you know. But if you’re not that fussed, there’s not much point aspiring to live that way.
The future is a landscape, not a road
The journey is a popular metaphor for life. We’ve been there, we’re here now, and we have to go forwards. That makes it tempting to assume we need a destination and measure our progress.
If I take where I am now, though, I can imagine I’m on a hill. Spread out ahead is a landscape. In this “journey” way of thinking, I can focus on the detail and look for where I most want to be. Or I can delight in the sheer range of possibility. One approach makes me look for the best road, the other emphasises the surroundings. For the decisive, the landscape is the backdrop to their road; for the open, the road is what takes them through the landscape.
For some of us, life is more joyful with a sense of possibility. You’ll know if that’s you. And if that’s the case, what will make us happy is choosing paths rich in possibility, not focusing on a goal.
What difference does it make, practically? Well, staying with the map metaphor, we don’t look for the route to somewhere, we assess which direction is nicer. We think back over the places we’ve travelled through that we liked, and head for wherever looks like it has more like that. Especially on the way.
Back in reality, we choose according to what each choice makes possible or impossible, not according to a defined end. For me, I didn’t go to university after school partly because it felt restricting to me, having to decide a subject and stick with it. Later, after some years at work, I studied for a degree because I knew enough by then to want the directions I knew it could open up for me. At eighteen, it felt like closing too many roads ahead, and at thirty it felt like opening them up. If I’d dreamt of being a doctor or lawyer, that wouldn’t have worked, but I didn’t have a dream.
You don’t need a dream
People sometimes say they envy their dogs, happy living in the moment. And then carry on feeling guilty because they’re not making enough progress … towards what? We don’t all have a singular vision for the future, and it’s artificial to impose one.
If you can imagine a lot of potential futures in which you’d be happy, you’re already rich in a very important way. Don’t let anyone make you decide which exact one of those is THE one unless you need to. Or feel guilty because you haven’t.
The trick, for us, is to live in a way that maximises those potential futures across all of them. And this is where I argue that planning is counter-productive.
Richard Feynman, the influential scientist, spoke of “favourite problems”. These were not things he actively worked at answering. He parked them, as things that he would like to answer, that should be answered, but he didn’t choose any of them. He researched, and worked on whatever seemed promising, and regularly considered his list of favourite problems to see if anything that had come up shed light on any of them. He chose lines of investigation that might be promising across various of them, assuming there were deep things in common that might not be obvious.
Steve Jobs, on returning to Apple with the company almost bankrupt, performed what amounted to drastic surgery, but when asked what he intended to do positively said that something would come up. He knew that tech and business has tides and cycles, and that there would be something to catch, and picked music and the iPod when things aligned around that. Which led to the iPhone.
This way of thinking is not aimless. It’s aware.
Rather than being focused on a particular future, and working on steps to make that future a reality, this mindset is much more in the moment.
It holds values and ideals, hopes and fears, and measures them against what is around. Whatever boosts most of the things we hope for and guards against what we dread, that’s what we pick. And because we don’t have one goal and a plan to get there, we can be more aware. We can spread our “luck surface area”.
What’s more, we can enjoy the present. If everything around is a possibility, if we’re accustomed to looking at all our circumstances not as obstacles but as potential, life feels more meaningful in itself, not just as a waypoint on the way to somewhere.
My career, for example, is more careering than a wayward car. I did graphic design, accountancy, construction management, sales, photography, lab testing, product design, procurement … and then settled into business system software. At each point, I was working on what felt important at the time, without knowing what it might lead to, but there were common threads of making things, analysing things, creating processes. Most of those things involved increasingly elaborate spreadsheets over time. And when a line of work I hadn’t known existed fell into my lap, I had the skills and could recognise something that suited me and run with it. I can’t imagine how I might have got to where I am knowing only what I knew as a teenager, but here I am and happy.
And still constantly looking to see whether there’s a line of business that might take me in another great direction. Who knows what might turn up?
So, no planning?
Now, one thing I’ve learnt from personality testing is that I max out on openness (which makes me infuriating for managers, apparently – we open people are fine with other attitudes, but decisive types really want to decide what’s best and impose it). So I rule out nothing, ever. And certainly I don’t rule out planning.
If, on my journey, I meet a swamp, planning how to get round or across it is sensible.
If there are a lot of potential futures in which we’d need more space in our house, and a lot of potential futures in which we’d be sorry we’d used all our savings, we might settle on adding a conservatory to the house. We wouldn’t get very far waiting for something to occur which somehow gave us more space without us taking positive action. And once we’d decided to add a conservatory, that becomes a goal, and planning is completely appropriate and downright necessary. We need to narrow down the potential future state and sort out how we get there.
As a business owner, responsible for client projects, I wouldn’t get far without planning … though I am more likely than most to suggest the “range of possible futures” approach.
Planning is great. Planning is necessary, at the appropriate scale.
Unless planning in itself makes you happy, planning shouldn’t run your life, and it shouldn’t be your life. Your life is your life.
If your life is going well, enjoy it, and pay extra attention to whatever is likely to lead to more enjoyment.
If your life is going badly … consider what things around you have the most potential to help, start there, and see if they lead to things that help with the next step.
If you’re desperate or have an all-consuming dream, by all means make a plan. You may need one, and I won’t ever tell you otherwise.
For some of us, it isn’t the way, and that’s fine.
And this is what an essay without a plan looks like. It could probably be better, but here we are anyway, which is a lot like life.