Planning and Fear

More of my time has been lost due to fear than poor productivity. I am a sucker for productivity hacks. If there is a tool or system that can squeeze a little more out of my day, I’m willing to try it. For a long time, this leads to a cycle. I would try something new for a while, run into a wall, discard it and repeat. I found myself discarding something and trying something new only to come back to the thing I had discarded. Usually with some renewed vigour that this time it would be different. I did this for a long time. Somewhere through this process, I noticed I was doing it. Why I was caught in this cycle turned out to be simple, in the most frustrating way. I ran in circles because doing fake work is easier than doing real work.

I first began to notice the pattern after reading Cal Newport’s Deep Work. It was some time in 2013, and I was a year or so into my PhD. Newport’s book helped me see that a great deal of the work I had done so far was shallow. Optimising code rather than solving research problems. If you looked into my office at the time, I would have looked productive. Days planned into neat, hourly blocks, a todo list being ticked off, Pomodoro timers ticking away. Day’s flew by, but I wasn’t moving anywhere important. Eventually, I started to notice. My first thought was that my day planning must be wrong. I dropped my daily routines and found new ones. They were fresh, and it felt different. That feeling sustained me until I ended up in the same position. I wish I could say it only happened once before I caught on. I got there in the end but not without wasting more time on the wrong thing.

The reality is that the world is full of things adjacent to real work. These nearby things feel like work. They take time and effort. They’re close enough to the actual work to feel like progress. Newport’s Deep Work was the first hint that maybe not all progress is a good use of time. It was easy to fill my day with shallow work. It felt like an accomplishment, but it wasn’t the real work. I needed to learn to cut through to the actual work. As Scott Young put it in his post, I needed to Do the Real Thing.

I took a long time to learn to move past the shallow work. Sitting down and taking an objective look at your output is hard. It likely falls into the category of deep work. A part of me knew. That part of me was happy in the illusion. To create an honest reflection of how I was spending my time was scary. I wrote down everything I wanted to achieve and everything I had done or had planned. I had to stare at the page and realise there wasn’t a clear link between them. Once it was on paper, it was clear. It was scary and demoralising. There were many points where I wanted to stop and find a new ‘hack’ instead. I knew, though, that if I wanted to get something important done, I had to be honest with myself.

Looking back over the time since 2013, I know I have fallen into the same pattern from time to time. Each time I do, I get a little more comfortable facing the hard truths. A little more comfortable admitting to myself when I am wasting time. A little more forgiving as well. I realise that what stops me is usually fear.

Fear is a strong driver or behaviour. It can stop us doing essential things. Several times when writing this, I have thought to myself “Elliot, what are you doing, you don’t need to write this”. From years of that same feeling, I know that it comes from a place of fear. A fear that what I write won’t resonate. A concern that I said something wrong. Pushing past that fear to carry on regardless has taken time to learn. I’m not always perfect at it, but I can look at those feelings and recognise them for what they are. Once I understand them, I can move past them.

These roadblock fears are often the easier ones to push through. They only appear when you are moving towards real work. Eventually, once I learned to spot these signs, I grew to like them. They were a sign that I was heading in the right direction. The same way that I get nervous before a pitch or talk. They’re a small reminder that something good is going to happen. Unfortunately, this is not the only way that fear can block progress. It has a more damaging and more subtle way to keep us from feeling uncomfortable.

The second form of fear shows up when we are planning. It’s the form that leads to cycles of productivity hacks and days full of shallow work. This form of fear doesn’t feel scary. It hides behind the excitement—the excitement of planning and productivity. Things I very much enjoy. It steers me in the wrong direction. It causes me to link a lack of progress to a failure in the system. This process can go on for a long time. Getting past it is not easy. It takes honest reflection—the type of reflection where you take a hard look at yourself. When self-reflection and productivity hacks are the choices at hand, it is no wonder I’ve picked the easy one so many times.

I have become better at this by learning and practising self-reflection. In practice, this is a combination of regular reviews and making choosing the real work simple. To help make choosing the real thing simple, keep a list—a list of things you are avoiding. I have a separate TODO list called ‘The Avoidance List’. I add items to it whenever they cross my mind. Things I know that I should be doing but aren’t. Then, when I come to plan, I make sure that is the first place I look. It is not an instant cure, but it means that when I plan, I’ve already done the hard work of choosing what’s important. Reflection comes in the form of looking back over my day or week and being honest with myself about what got done.

That doesn’t mean I try to spend every day working 24 hours at 100% capacity. Doing essential things and making use of every waking second are different goals. This idea was captured well in the post How to Be Great? Just Be Good, Repeatably. Younger me was obsessed with productivity because I felt it was the path to progress. More than that, I thought it was the only lever I could pull. I know now that it is one piece of a bigger system. Productivity on the wrong things is worse than being unproductive. It drains your energy without moving you forward. My current go-to model for this is from Greg McKewon’s book Essentialism. McKeown describes it as “The Disciplined Pursuit of Less”. It is easy to overlook the word disciplined in that description, but it is key to success. A single weekend of planning or a late-night productivity revolution isn’t the answer. They may provide a burst of action, but every time I have relied on these bursts, I am back to where I started before too long.

The best path to dispelling fear is putting in the time. In this case, it means making reflection a regular, almost constant activity. Every time I do it, I build an internal filter for fear-driven work. I get a little better at planning for the real things. Day by day, week by week, I learn to spot the important stuff. I learn to spot the cosy distractions and spend more of my time on the things that matter. I am planning for the fear so that fear doesn’t do the planning.

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