What to Do When You’re Stuck

3 September 2019 by Phillip Johnston • Last updated 24 July 2023

Projects don’t always go well. We encounter many road bumps and errors along the way. There are always one or two major problems that suddenly appear and threaten to sink the ship. These problems can seem to drag on forever. We check our work, try every possible thing we can think of, and then resort to trying random things after that. No matter what, the problem won’t yield. But you know a solution is out there, it always is, so you keep searching, even while a sense of dread builds up inside.

When we are in this kind of situation, it can feel hopeless. We can’t provide a schedule to a client’s or manager’s looming or already past deadline. We feel the weight of the project resting upon our shoulders. Benevolent people want to ask how it’s going and offer encouragement, which only emphasizes the importance of our work and the impact the delay is having.

I know this first-hand. At the time of writing this article, I have been stuck on the same problem for over a week, with probably 60 hours spent actively investigating it. We must resolve the problem somehow, or else the project will be a complete failure for us and for our clients. We also don’t have unlimited time to solve the problem. Eventually, the clock will run out and the project will be terminated.

I started thinking about how I generally overcome this type of problem, and I noted these strategies:

1. Detachment
2. Break Down the Problem
3. Take Care of Yourself
4. Review Your Debugging Process
5. Inject Novel Ideas
6. Throw it Out and Start Over

Detachment

Before attempting anything else, we need to detach ourselves from the problem. Step away. We can grant ourselves a break and a reset. We want to get to a place where we can take a new perspective on our problem. This step is critical, and the longer you’ve been wrestling with the problem the harder it will be.

It doesn’t matter how you acquire a measure of detachment. There are many approaches, and you must find something that works for you:

• Go for a walk
• Exercise
• Listen to music
• Take a nap
• Call someone you enjoy talking to
• Cook something special
• Slowly make a pot of tea
• Play a game

This step seems small, but it is crucial. I quoted the stoic philosopher Seneca in our article, How I Schedule My Day as a Consultant, and it is worth repeating here:

We need to give our brain a rest. We’ve become emotionally invested in the problem, and our emotions (especially frustration) are clouding our thinking. We want to let go of our feelings about the problem. We need to let go of what we’ve already tried to do. Those attempts didn’t work. We can’t keep attacking the problem from the same point if we want to move past it. We’re stuck.

Our goal in achieving detachment from the problem is to re-enable clear thinking and to make our minds receptive to new ideas.

Sometimes all we need for a breakthrough is fresh air and separation from the problem. Even if we don’t find a solution during a break, a relaxed and detached perspective is necessary for clearing up our thinking and making progress on the problem. Former US Navy Seal Jocko Willink puts it succinctly:

Detach. Step back. Clear mind. Assess.

— Jocko Willink (@jockowillink) November 27, 2017

Break Down the Problem

Sometimes we feel stuck because of the sheer enormity of the task ahead of us.

Often, problems feel enormous because they are not well defined. Simply decomposing an enormous problem or task into smaller steps is enough to get you unstuck. When it’s clear what the next step is, and what comes after that, you can work through each in sequence until the task is complete.

This strategy also relies on building momentum. When a number of clear, small steps are laid out before you, it becomes easy to knock out one after the other. This builds momentum, which will help carry you through difficult sticking points. Inertia can keep you stuck if you attempt to dive into a large problem without sufficient momentum.

Take Care of Yourself

With persistent and difficult problems, I’ve noticed a tendency to fall into a trap: I stop taking care of myself.

We can’t forget to rest. Tricky problems lead to long working hours, poor eating habits, over-caffeination, and sitting too long. These actions will cloud our minds, slow our thoughts, and make us less effective.

Take frequent breaks. Don’t work too late. Go for a walk every two hours. Don’t skip meals. Make sure you are eating healthy food at your preferred mealtimes. Make sure you are staying well hydrated. Don’t drink extra coffee. Get plenty of rest at night (extra, ideally, because your brain is working hard).

Taking care of yourself is crucial for maintaining detachment and clear thinking. It’s true that the problem is weighing on you, and that the team is waiting on you, which are both hard to deal with. But if you don’t take the time to take care of yourself, you are reducing your effectiveness and prolonging the path to resolution, thus hurting the entire team.

Review Your Debugging Process

With tricky problems, we can easily fall into a trap of random debugging. We become frustrated and start running all sorts of random experiments, often bundling multiple changes into a single test run. Eventually, we end up feeling like we’re repeating the same tests, but we’re not exactly sure anymore.

When we find ourselves in this situation, we need to step back and revert to a proper debugging process. We should be working methodically, in small steps, testing hypotheses, and noting down the details and results of each experiment. Attempt one thing at a time, observe the outcome, and write both down in a debugging log. The goal is to find the critical variables and to rule out those areas of investigation that have no impact on the problem.

If you don’t have a well-established debugging process you can revert to, I recommend reviewing Debugging: 9 Indispensable Rules. Here are the rules outlined in that book:

1. Understand the System
2. Make it Fail
3. Quit Thinking and Look
4. Divide and Conquer
5. Change One Thing at a Time
6. Keep an Audit Trail
7. Check the Plug
8. Get a Fresh View
9. If You Didn’t Fix it, It Ain’t Fixed

Inject Novel Ideas

We’re working on a persistent problem, and we’ve already exhausted all of the ideas we had for solving it. We’ve probably even tried random things to see if anything would make the problem budge. If you’re reading this article in the middle of such a problem, you might even think there are no ideas left for you to try.

This feeling is why it’s crucial to detach, make sure we’re taking proper care of ourselves, and re-establish a debugging process. Once we’ve restored our ability to think clearly and methodically, we need to infuse our mind with new ideas. There are a few different ways to do this:

1. Talk Out Your Problem
2. Consult the Oracle
3. Review Prompts

Talk Out Your Problem

One place to turn for novel ideas is another human, ideally one who is detached from the situation. Talk through the problem with people who might be familiar with what you are working on, as well as people who are completely outside of your field. In the best case, we might receive extremely helpful advice. Otherwise, simply having to explain the problem will often provide us with new ideas or point out holes in our understanding. People notice when we’re glossing over details, providing hand-wavy answers, or not able to answer questions. These are all areas we can explore further in our debugging efforts.

Sometimes another human isn’t available. In such situations, the common advice is to explain your problem to a rubber duck (or other inanimate object). The act of translating our thoughts into words will provide many of the benefits talking to another human can provide.

Consult the Oracle

Even after talking to our trusty companions, we may find that we’re still out of ideas. In such cases, I like to let my subconscious work for me through a method I call “consulting the oracle”. First, I state a clear question or problem statement either in writing or in my mind (this is not a yes/no question, but something open-ended). One the question is asked, I apply a random input and receive an answer. The answer often prompts my subconscious mind into thinking up something related to both the problem and answer. My goal is to take the problem in a new direction: the solution is probably going to be in a place I haven’t already looked.

The part of the process that is variable is the method we use for applying a random input and receiving an answer. My two favorite “oracles” are the _I Ching_and Brian Eno’s Oblique Strategies.

The I Ching is an ancient Chinese oracular text. You throw coins (or yarrow stalks) and generate a hexagram. The book provides an image, a judgment, and commentary on the symbol. The I Ching is often consulted when making decisions or trying to explore one’s internal state, but it also can provide effective approaches and triggers for solving problems.

Oblique Strategies is a set of cards created by Brian Eno in the 1970s. The cards offer guidelines and constraints to help artists (primarily musicians) work past creative blocks. Since the cards are designed for artists, not all of the strategies apply to a technical situation. Some, however, are powerful triggers that may cause you to reframe the problem completely. Using this deck, we can take two approaches. First is the strict approach: draw a card and follow it exactly. The second approach is to pull cards until we find one that resonates with us – our brains will give us a feeling of “hey, maybe that will work!” when we find a card that resonates. Follow that trail!

If you doubt the efficacy of consulting an oracle, I simply ask you to view this strategy from another perspective. The point is to provide a fresh take on our questions and to let our own minds provide the answers from our subconscious associations. We must receive new input in order for the brain to generate new output. That input doesn’t have to be reasonable, and it doesn’t have to be related to the problem. We are simply trying to jiggle our brains so they can change state and generate a new perspective.

Review Prompts

Rather than consulting an Oracle, you could simply review a list of prompts, hoping that one of them jiggers you to get unstuck. You might use the Oblique Strategies  for this, or you might work through these questions from Todd Henry’s Daily Creative:

Throw it Out and Start Over

If you remain stuck, sometimes the best decision is to throw out our previous attempt(s) to solve the problem and start over. This can be a painful and counter-intuitive process, especially with a looming deadline. But now we know a lot more than we did during the initial implementation. We can implement a second-pass solution more quickly, or at least in a better fashion than the first attempt.

My main concern with a problem that drags on too long is that the problem isn’t actually what (or where) we think it is. What if the problem is related to a small detail that is only tangentially related, or a detail that we have ignored completely in our investigations? We can scrap the idea and re-implement the same approach, or we can free ourselves to attempt an alternative approach. Through this process, we will either overcome the problem or confirm that the problem is as real as we think it is.

Still need help?

Sometimes, we keep our head about us and follow all of these guidelines, but we can’t get past the obstacle.

If you really can’t figure it out, give us a call – we’re detached from your problem and can bring in a new perspective. Plus, we love debugging and helping teams move past tricky and persistent problems.

Further Reading

• Oblique Strategies (consult the oracle online)
• Oblique Strategies on Amazon
• Wikipedia: Oblique Strategies
• I Ching
• Wikipedia: I Ching
• Rubber Duck Debugging
• Detaching For Clear Thinking – Jocko Willink and Leif Babin
• Debugging: 9 Indispensable Rules
• My Favorite Debugging Tip: Get Up and Take a Walk!
• Pareto Principle for Software
• How I Schedule My Day as a Consultant
• Schedule a Consultation

References

• Daily Creative by Todd Henry, 23 July entry