Everyone gets stuck. Whether it’s technical work, drudgery, or anything in between, tasks that stop you in your tracks can be frustrating and stressful. The effects can compound when it involves your superpower and expectations are high. While there’s no panacea, I’ve collected a few tricks to help me get back on track when I hit a wall.

Diagnose

My first trick is to ask why? Am I overwhelmed? Do I have analysis paralysis? Am I unmotivated? Is this an unsolved problem? Am I procrastinating? Is someone or something blocking me? Putting a name to the problem is the first step to getting unstuck: tactical solutions depend heavily on what’s the cause. If I’m overwhelmed I may try breaking the problem down into simpler parts; however, if I’m unmotivated this won’t help much.

After I’ve identified the apparent cause, the next trick is to again ask why? I’m overwhelmed, but why? Am I normally able to do similar tasks without issue? What’s changed? Be honest with yourself and try to pinpoint what specifically is holding you back. It can be concrete or nebulous. There’s no need to unleash your inner toddler’s unquenchable curiosity with endless rounds of “why?” Just get past a surface-level explanation.

Recently, I was working on a new blog post for work. I generally enjoy writing, and I was proud of the project I was writing about. I received great suggestions in the review of my first draft, however, I felt a bit stuck. The normal flow of words started slowing down to a trickle. I kept rereading the same passages, then the suggestions, and then the passages again. The changes were straightforward, and the bulk of the ideas were already present, so why was I having such a hard time editing?

After a bit of reflection I realized I was specifically having trouble writing about the non-technical parts of the project. But why? I had been so in the weeds implementing the model over the last quarter that I hadn’t had time to formulate my higher-level thoughts. Explaining what I implemented technically was a breeze. Framing and motivating the project were less fresh in my mind and
I just needed a bit of time to reflect and let my thoughts coalesce. With this small insight, I broke out of the rereading loop and felt unburdened.

There is a fine line here: we’re not robots and not everything has or needs a quick fix. If you often find the answer to “why?” is a lack of motivation, feeling overwhelmed, or exhaustion, this can be your body warning you something more serious is wrong. These are indicators of burnout, and you’ll need to be more purposeful with trying to change fundamentally how you interact with your work and role. Preventing burnout is beyond the scope of this post, but you can use this technique to periodically check-in with yourself.

Make a Plan

After I’ve root-caused the issue, my next trick is to make a plan. I’ve identified why I’m blocked, and now I just need to come up with a strategy to address the problem. Taking a step back to frame being stuck as a problem to be solved can help you break out of an impasse and attack the underlying issue from a new angle. Making a plan is easier than diving in because it’s just a stepping stone. We’re not directly working on the task that is causing us grief, we’re just brainstorming. Whether the plan is perfect or not, just compiling it can feel like progress and make the end goal feel a bit less insurmountable.

Depending on what you’re stuck on, the plan can be very simple or quite complex. In any case, it should be tailored to your answers to “why?” Stopping to think worked for my blog post edits, but it wouldn’t help much if I was stuck because I was anxious about other projects I knew were waiting. It’s important to remember that no plan is foolproof. You might have to change it, or even create a completely different one. Something that works for me might not work for you. Keep track of what does and doesn’t work, and develop your own personal runbook for common situations you find yourself stuck on.

For example, let’s imagine writing emails feels like pulling teeth. You’ve determined that it’s hard for you to figure out where to start – blank page syndrome. When you dig a bit deeper, you realize you often get distracted with Slack messages while deciding what to write. When you go back to the email, you feel guilty about still not starting it, and you know your other work is still waiting for you. You decide to make a plan:

• Mute Slack
• Start with unordered bullets of what you want to say
• Organize the bullets into an outline
• Fill in the details

If this works for you right away, great! Now you have a strategy you can reapply in the future. But it might not work, and that’s okay too! Figure out which parts worked and which did not, then adjust. Maybe when you muted Slack, your coworker walked over to your desk to ask you a question in person. You then adjust the plan to also put on headphones, signaling to others it’s focus time.

Making a plan can mean a lot of things, but here are a few general techniques I employ to make the process easier.

• Keep notes
  • Track your thoughts, questions, important links, to-do lists etc. This helps reduce your cognitive load, and you can leverage them as a jumping off point (avoiding blank page syndrome). I like Obsidian, but the best tool is the one you will use
• Decompose the problem
  • If the problem is too complex to solve head-on, break it down into simpler parts. This can be an iterative process. Start high-level and keep going until you feel like the sub-problems you’ve identified sound easy or straightforward.
• Sharpen your axe
  • Spend time thinking about the problem before jumping in. This is especially important for novel problems (or even just novel to you). This can mean ruminating alone, doing research, or rubber-ducking with a colleague. You’re affording yourself time to identify the most promising solutions without committing to the first thing that comes to mind.
• Focus
  • Know when you’re most productive and block off focus time. Move meetings, silence Slack, put on headphones. Give yourself the best chance to succeed by making it easier on yourself. Just because you’ve removed distractions doesn’t necessarily mean you’ll be productive: this is a habit you have to build.

Just Do It

The last trick I have is to just do it. Without being too glib, I often find the act of doing something much more freeing than doing nothing. When you’re staring at a problem unable to make progress, it’s easy to think of all the things that won’t work. When you start doing something, even if it’s wrong, you can focus on just the one thing you are doing now. You might have to delete all the code you just wrote, but you’ve still made progress. Hopefully you’ll even be able to keep some of what you created.

Diagnosing what makes a task hard, and crafting a plan to tackle it are great tools. But it’s also important not to get carried away. Don’t get lost in this meta-work just to procrastinate the underlying job. My inner perfectionist is often enticed by these less concrete steps. At some point I have to silence that voice, and just start drafting. If I know what I’m doing is not going to be the final product, there’s less pressure to get it right from the get-go. I can always iterate or revise.

The best laid plans of mice and men don’t ship. No plan will be perfect, and some things require getting your hands dirty before you realize what’s really going on. You can brainstorm new feature ideas for a model all day, but until you start playing with the data, you’ll be hard-pressed to know what’s going to work in practice. The act of doing is a learning process. Whether you solve the problem or not, you gain information and get one step closer to finishing the task.

For the most challenging problems, remember to pace yourself: not everything needs to be a grind. Take regular breaks, get a coffee, go for a walk. Find a natural stopping point, and write down whatever is in your head so you can pick up seamlessly from where you were. If you haven’t fully crafted a solution yet, consider working on something unrelated for a bit while you subconsciously process the problem at hand. If you’re finding it hard to concentrate or your thoughts are fuzzy, it’s probably a good time to set the problem aside for a bit.

Final Thoughts

Getting stuck is a natural part of work. Instead of letting it defeat you, use it as an opportunity to learn more about yourself. There’s no secret formula, but I’ve found that assessing the underlying issue, mapping out how to circumvent it, and then attempting to make progress are three pillars that help me break through.

Practice makes perfect. It will be hard at first to go through these steps, but it’s about making habits. Find what works for you and add it to your repertoire. By building up pattern recognition and applying past learnings, you’ll find that what used to be hard yesterday won’t be quite so bad tomorrow.