These ideas came out of a recent discussion on actually trying at Citadel, Boston's Less Wrong house.

What does "Actually Trying" mean?

Actually Trying means applying the combination of effort and optimization power needed to accomplish a difficult but feasible goal. The effort and optimization power are both necessary.

Failure Modes that can Resemble Actually Trying

Pretending to try

Pretending to try means doing things that superficially resemble actually trying but are missing a key piece. You could, for example, make a plan related to your goal and diligently carry it out but never stop to notice that the plan was optimized for convenience or sounding good or gaming a measurement rather than achieving the goal. Alternatively, you could have a truly great plan and put effort into carrying it out until it gets difficult.

Trying to Try

Trying to try is when you throw a lot of time and perhaps mental anguish at a task but not actually do the task. Writer's block is the classic example of this.

Sphexing

Sphexing is the act of carrying out a plan or behavior repeatedly despite it not working.

The Two Modes Model of Actually Trying

Actually Trying requires a combination of optimization power and effort, but each of those is done with a very different way of thinking, so it's helpful to do the two separately. In the first way of thinking, Optimizing Mode, you think hard about the problem you are trying to solve, develop a plan, look carefully at whether it's actually well-suited to solving the problem (as opposed to pretending to try) and perhaps Murphy-jitsu it. In Executing Mode, you carry out the plan.

Executing Mode breaks down when you reach an obstacle that you either don't know how to overcome or where the solution is something you don't want to do. In my personal experience, this is where things tend to get derailed. There are a few ways to respond to this situation:

Return to Optimizing Mode to figure out how to overcome the obstacle / improve your plan (good),
Ask for help / consult a relevant expert (good),
Take a break, which could lead to a eureka moment, lead to Optimizing Mode or lead to derailing (ok),
Sphex (bad),
Derail / procrastinate (bad), or
Punt / give up (ok if the obstacle is insurmountable).

The key is to respond constructively to obstacles. This usually means getting back to Optimizing Mode, either directly or after a break. The failure modes here are derailing immediately, a "break" that turns into a derailment, and sphexing. In our discussion, we shared a few techniques we had used to get back to Optimizing Mode. These techniques tended to focus on some combination of removing the temptation to derail, providing a reminder to optimize, and changing mental state.

Getting Back to Optimizing Mode

Context switches are often helpful here. Because for many people, work and procrastination both tend to be computer-based activities, it is both easy and tempting to switch to a time-wasting activity immediately upon hitting an obstacle. Stepping away from the computer takes away the immediate distraction and depending on what you do away from the computer, helps you either think about the problem or change your mental state. Depending on what sort of mood I'm in, I sometimes step away from the computer with a pen and paper to write down my thoughts (thinking about the problem), or I may step away to replenish my supply of water and/or caffeine (changing my mental state). Other people in the discussion said they found going for a walk or getting more strenuous exercise to be helpful when they needed a break. Strenuous exercise has the additional advantage of having very low risk of turning into a longer-than-intended break.

The danger with breaks is that they can turn into derailment. Open-ended breaks ("I'll just browse Reddit for five minutes") have a tendency to expand, so it's best to avoid them in favor of things with more definite endings. The other common say for breaks to turn into derailment is to return from a break and go to something non-productive. I have had some success with attaching a sticky-note to my monitor reminding me what to do when I return to my computer. I have also found that if the note makes clear what problem I need to solve also makes me less likely to sphex when I return to my computer.

In the week or so since the discussion that inspired this post, I have found that asking myself "what would Actually Trying look like right now?" This has helped me stay on track when I have encountered difficult problems at work.