Problem-Solving

You’re stuck.

Something isn’t working. You’ve tried the obvious things. You’re going in circles. The problem seems impossible.

Being stuck is universal. What differs is what you do about it.

This isn’t about having all the answers. It’s about having frameworks for finding answers - or at least for making progress when progress seems impossible.

Why we get stuck

Wrong problem. You’re solving a problem that isn’t the actual problem. You treat symptoms instead of causes. You assume you know what’s wrong without checking.

Missing information. You don’t have the data or knowledge you need. But you don’t know what you don’t know.

Too close to see. You’ve been staring at it so long you can’t see it fresh. Assumptions become invisible. Alternative approaches become unthinkable.

Emotional hijacking. Frustration, fear, or ego prevent clear thinking. You become attached to approaches that aren’t working.

Wrong tools. You’re using familiar tools that don’t fit this problem. When you have a hammer, everything looks like a nail.

General-purpose strategies

Define the actual problem

Before solving, make sure you’re solving the right thing.

Ask:

• What exactly is the problem? (Be specific)
• How do I know it’s a problem? (What’s the evidence?)
• Whose problem is it? (Maybe it’s not yours to solve)
• What would “solved” look like? (Define success)
• Is this the real problem or a symptom? (Dig deeper)

Many stuck situations dissolve when you realize you’ve been working on the wrong problem.

Break it down

Big problems are overwhelming. Small problems are solvable.

If you can’t solve the whole thing, what’s the smallest piece you can make progress on? Solve that. Then the next smallest piece.

Progress creates momentum. Momentum creates clarity.

Work backwards

Start with the end state and work backwards.

What would need to be true for the problem to be solved? What would need to happen before that? And before that?

Working backwards often reveals steps that are invisible when working forward.

Ask better questions

The quality of your questions determines the quality of your answers.

• Instead of “why won’t this work?” → “what would need to change for this to work?”
• Instead of “what should I do?” → “what are all my options?” (then evaluate)
• Instead of “is this right?” → “how would I know if this is right?”

Questions that open up possibilities beat questions that close them down.

Change your state

When stuck mentally, change something physical:

• Take a walk
• Sleep on it
• Do something completely unrelated
• Exercise
• Talk to someone about something else

This isn’t procrastination - it’s strategic incubation. Your subconscious continues working. Fresh eyes see fresh possibilities.

Seek outside perspectives

Your assumptions are invisible to you. They’re visible to others.

• Explain the problem to someone who knows nothing about it
• Ask people in different fields how they’d approach it
• Rubber duck debugging: explain it out loud (even to an inanimate object)

The act of explaining often reveals gaps in your thinking.

Question your constraints

Some constraints are real. Some are assumed.

“We can’t do X because…” But is that actually true? Or is it just how things have always been done?

Try: what if the constraints didn’t exist? What would you do? Sometimes this reveals that constraints can be removed or worked around.

Accept imperfect solutions

Perfectionism causes stuck. Sometimes “good enough” beats “perfect but never.”

• What’s the minimum viable solution?
• What would 80% of the benefit with 20% of the effort look like?
• Can you solve it partially and iterate?

Shipped beats theoretical.

Problem types and approaches

Different problems need different tools:

Analytical problems (clear right answers)

• Break into components
• Apply systematic methods
• Check your logic
• Verify with data

Creative problems (no clear right answer)

• Generate many options before evaluating
• Combine unexpected elements
• Remove constraints temporarily
• Prototype and iterate

People problems (involving humans)

• Understand different perspectives
• Focus on interests, not positions
• Communication often beats analysis
• Relationships matter more than logic

Wicked problems (complex, unclear, changing)

• Don’t expect to “solve” them - manage them
• Small experiments over big plans
• Embrace iteration
• Accept partial progress

When you’re truly stuck

If nothing is working:

1. Stop. Continued effort when stuck often makes things worse. Take a real break. Hours. Days.

2. Question the goal. Maybe you’re pursuing something you shouldn’t be. Is this goal still valid? Is it even your goal?

3. Accept uncertainty. Maybe this can’t be solved right now. Maybe you need to live with not knowing for a while.

4. Get help. Pride prevents asking. But other people have solved problems like yours. Find them.

5. Document what you’ve tried. Even if you don’t solve it now, future you (or someone else) will benefit from knowing what didn’t work.

A minimal problem-solving process

1. Define the problem clearly (what exactly is wrong?)
2. Break it into smaller pieces
3. Generate multiple options (don’t stop at the first idea)
4. Try the most promising one
5. If stuck, change something (perspective, state, approach)
6. Get outside input
7. Accept imperfect progress

Being stuck is temporary. It always has been. This too shall pass.

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Related: Decisions (choosing between options), First Principles (breaking down fundamentals), Uncertainty (living with not knowing)