Mini Blog Post 6: Stop pressing the Try Harder button

I recently had a productivity coaching session, and at the end we agreed on a few actions points that I’d do by the next session. But, come the next session, these had completely slipped my mind. These suggestions were good ideas, and I had no issue with implementing them, the problem was just that they completely slipped my mind! (We then spent the second session debugging my ability to actually follow action points, and this was pretty successful!)

I think the error I made there is a really common one when planning, and one I observe often in myself and others. Often I’ll hear a cool book recommendation, offer to meet up with someone some time, hear about a new productivity technique, notice an example sheet deadline looming. But I consistently fail to action upon this. So this post is about what exactly went wrong, and the main solution I’ve found to this problem!

Planning, as I define it, is about ensuring that the future goes the way I currently want it to. And the error I made was that, implicitly, I was trying to make the future go the way I currently wanted it to. That by committing to do things, and wanting to them, and just applying effort, things would happen. And the end result of this was that I totally forgot about it. Or sometimes, that I vaguely remembered the commitment or idea, and felt some guilt about it, but it never felt urgent or my highest priority. And every time I thought about the task, I resolved to Try Harder, and felt a stronger sense of motivation, but this never translated into action. I call this error Pressing the Try Harder button, and it’s characterised by feelings of guilt, obligation, motivation and optimism.

This is a classic case of failing to Be Deliberate. It feels good to try hard at something, it feels important and virtuous, and it’s easy to think that trying hard is what matters. But ultimately, trying hard is just a means to an end - my goal is to ensure that the task happens. If I can get it done in half the effort, or get somebody else to do it, that’s awesome! Because my true goal is the result. And pressing the Try Harder button is not an effective way of achieving the goal - you can tell, because it so often fails!

A good litmus test for whether you’re pressing the Try Harder button: Imagine it’s 2 weeks from now, and you never got round to doing the task. Are you surprised that this happened? Often my intuitions are well-calibrated when I phrase the question like this - on some level I know that I procrastinate on things and forget them all the time.

But just noticing yourself pushing the Try Harder button isn’t enough - you need to do something stronger to change this. You need to find strategies that actually work. This is pretty personal, and much easier said than done! But it can be done. Look for common trends, strategies that have worked for you in the past, and things that you can repurpose.

Strategies that work for me:

• Scaffold systems - meta-systems that I check regularly

  • Calendars

  • Trello (my to-do list) - especially future reminders that result in an email

  • Getting friends to check in with me

• Do it now, not later. Set a 5 minute timer, and see if you can finish the task. Or at least make a start!

  • You can get a surprising amount done in 5 minutes! (Say, writing a third of a blog post)

  • Often the bottleneck is that getting started takes a bit of energy. Doing something for 5 minutes can take much less energy, and I find that timers help me focus a lot

• Make things concrete - often tasks feel overwhelming and fuzzy, so you put them off. Can you break it down into a concrete next action? Something that can be done in under 5 minutes?

• Schedule time for it - often the bottleneck is that it doesn’t feel urgent - I care about the task getting done, but I always have something seemingly-higher-priority to do

  • This is terrible, because in the long-run I always have something that seems short-term higher priority, and I never make time for my long-term goals

  • So if I make time in my calendar for it, and make it feel important that I stick to these, that’s valuable

  • I find focusmate.com valuable for carving out an hour for a specific task

• Add it to a queue

  • Ie a to-do list

  • I find Trello great for this - on Desktop I can add a new card from anywhere with CTRL+ALT+SPACE, it makes it really low friction

  • Important: It’s not enough to just add it to a list - the other half of a good to-do list system is having a regular time to process the list!

    • Having an eg weekly routine for this is important - a routine doesn’t involve decisions, it can just happen automatically. While if I just say “I’ll make time for it”, that’s pushing the Try Harder button!

• Accountability

  • Message a friend saying that I commit to this task

  • Extreme: Give a friend some money, and tell them to only give it back when the task is done

These are just the strategies that work for me - I’d love to hear what works for others, and expect it vary a lot between people. The message I want you to take from this post is just to notice when you next push the Try Harder button. And ask yourself: “am I just being virtuous and trying? Or am I trying to change what my future self actually does?”