Occasionally people ask for more detailed case studies of my productivity coaching, so I’m publishing these lightly polished notes from a talk I gave a few years ago. 

The following are real stories of people that I have permission to share under fake names.

Ariel

Ariel started to work with me near the end of her internship because she couldn’t get herself to work on the final project. She loved the work, but she’d procrastinated on starting the project for weeks. She described that the work was interesting, and she really enjoyed it when she did it earlier in the internship. However, nothing she tried could force herself to start work. And she didn’t know why. Why did she procrastinate so much on work she liked?

Since Ariel felt confused about what the issues even were, we tried a bunch of mini experiments. Would breaking the task down help? What about starting with a one-minute task so it didn’t feel so overwhelming? Maybe recording herself explaining a section, and transcribing that as a rough draft? 

Many of these experiments didn’t work. For example, financial penalties were a disaster. She still failed to do the task and felt worse about losing the money.

Which makes sense, as it turned out. As we discussed her goals and motivations, we found that Ariel really cared about this project. She wanted to do well, and she felt like to do well, she had to be able to sit down and write a good draft as the starting point. 

Except, she never felt ready to sit down to write a good draft. So she never started.

As she avoided the task, it loomed worse in her mind, until she couldn’t even think about it without feeling guilty. The pressure she was putting on herself paralyzed her. She felt like a failure because she couldn’t do this task as well as she had convinced herself was necessary.

So, one of the first layers we had to work with was perfectionism. Here, she had to work on internalizing the idea that she could iterate on her work. She could write a crappy first draft and come back several times to edit it until it was good. In fact, starting with a bad draft resulted in a better output than trying to start with a good draft.

We continued working together as she started a full-time job following the internship. As we continued peeling back layers, Ariel learned to sit with and manage anxiety. She worked on better productivity routines (such as setting lots of little deadlines instead of a few big ones) and getting rid of distractions (even putting her phone in a timed lock box so it didn’t distract her). She also got more comfortable asking for help and standing up for herself.

I saw her confidence blossom, but this process took a while -- and that’s normal. 

It can take a while to see progress when working through layers of maladaptive mindsets, inaccurate beliefs, and bad habits. Making progress is all the more difficult because often clients hold themselves up against unrealistic standards, so they feel bad about themselves even when they are improving. In these cases, it really helps to focus on progress over time.   

Pat

Now, many of the cases I work with are much simpler.

Pat worked in tech, but he wanted to transition to working on AI safety. In order to do that, he needed to self-study machine learning alongside his regular job. He was having a hard time staying motivated to study after work.

Pat came to me to increase his motivation, but talking with him, it became apparent that he didn’t have a clear plan. He didn’t know exactly what he needed to study, and that sapped his motivation before he could even try studying.

So, we started by having him put together a plan for what he thought he needed to learn. Then, he sanity checked that plan by talking to a couple people who worked at the orgs he was interested in.

That turned out to be immensely valuable. First, they told him that the list basically looked good, but about half of the things weren’t that important. So, he reduced what he needed to study by 50%, basically meaning he was learning the important content twice as fast.

Second, he started volunteering at one of the orgs. He ended up deciding to keep his regular job and continue volunteering on the side.

In Pat’s case, his desire to spend more time studying was a proxy for what he really cared about – making progress toward doing work he found meaningful. Setting clear goals, prioritizing only the most important tasks, and getting feedback early all helped him make much faster progress to that goal than he would have if he had just powered through more hours studying.

Phil

Phil started coaching as a senior studying computer science. He was preparing to start his master’s program. Except he hadn’t done that well in undergrad – he procrastinated chronically, started his assignments the night before they were due, and generally didn’t think he was prepared to get the most out of his master’s program. It was a make-or-break point. He was paying for this program, but he had to step up if he was going to make that investment worthwhile.

We started working on three main goals: daily planning, starting projects in advance, and implementing more effective learning strategies. However, over the first couple meetings, he only completed about half of the plans we made.

After setting the same goals a couple times, we discussed whether this was really the right approach. He really thought these were the goals he cared about - despite failing several times - so we agreed for him to try out financial commitments. If he didn’t complete the action item, he would pay a penalty. This seemed to help him get over the initial hump of trying out interventions.

During this process, we ran a bunch of experiments. With the goal of focusing better, some of his experiments included different work locations, organizing coworking groups, studying with his girlfriend, and penalties for individual tasks.

We had twelve calls over the span of four months reinforcing those key habits. He felt pretty happy with that progress, so we stopped coaching.

He returned a year and a half later. He’d done well in the master’s program and was working at a startup that he liked. However, he wasn’t getting as much done as he wanted. We set out to increase his productivity.

However, as we discussed why he wasn’t motivated, we found signs that maybe the job wasn’t a great fit for him. He liked the work but didn’t think the job was meaningful. He started exploring potential jobs and found some that felt very exciting.

However, in the process of choosing a specific goal to work towards, he noticed that it felt scary to think about changing. He liked his job and felt like he was learning a lot. Stepping into the unknown felt scary. Because of that fear, it had been easier not to really consider leaving in the first place. Instead, he could feel like he was making progress toward being more productive -- without having to face that decision directly.

This emotional hurdle was what he really needed to work past before he could make progress in his career. Last I heard from Phil, he had just started a new job he’s excited about and thinks could be really impactful.

Originally, Phil just needed to experiment. He needed to try a lot of things, with some accountability to help him follow through on them, to find the habits that would help him accomplish his goals. The second time, however, what originally seemed like a problem with not getting enough done, turned out to be an emotional hurdle that he needed to work around.

Conclusion

As you can see from these stories, productivity coaching covers a lot of ground. People frequently come to me with some version of “I want to get more done”, but the following process often includes experimenting, self-discovery, and zooming out to find the best path to accomplish their goals. It isn’t enough to just mindlessly apply a toolbox of productivity advice (however good the advice) – there isn’t a prescribed solution that will solve any particular problem. I know tips that often help, but a lot of the process is figuring out which strategies work for this particular person and situation.

I think this is also why it can be helpful to have a coach who works specifically with effective altruists. It gives me a shared mindset with my clients, so it’s easier for me to try to understand their perspective.