I’ve made several career transitions—physiotherapist to physiotherapy lecturer to academic researcher to head of department to school leadership. You’d think it gets easier but it doesn’t (at least, not for me). Each time I face these kinds of shifts, I still catch myself stuck on the same overwhelming question: “How do I make this transition work?” And each time, I have similar feelings. The frustration of “reading up” endlessly without much more clarity. Obsessing over the question of whether the move is right; right for me, right for my partner, right for the moment. It’s the paralysis that arises when you know you should be moving but can’t figure out which direction.

The question is the problem

Here’s what I’ve learned through multiple rounds of this: you’re not the problem. The question you’re asking is the problem.

Maybe you’re in a similar situation at the moment. “How do I progress in my career?” feels appropriately ambitious. It signals you’re taking your future seriously. But that question is really asking you to solve for technical skills AND industry positioning AND network building AND organisational politics AND personal brand AND negotiation strategy all at once. You can’t research your way through that—not because you’re not capable, but because you’re trying to answer six different questions as if they were one.

Which is why you feel stuck. You’re gathering information but can’t make it cohere into action. The paralysis isn’t a personal failing. It’s what happens when you try to solve a multi-variable problem with a single question.

Making problems tractable

Here’s what changed for me: I stopped asking “How do I become a leader?” and started asking smaller questions. “What do academic leaders actually do day-to-day?” That’s answerable—I could observe, ask, map it out in a week. “Which parts of that role align with work I already find energising?” Also answerable through honest reflection and conversation.

The technical term for this is tractability—breaking complex problems into components you can actually get your head around. Not oversimplifying the complexity, but making it something you can investigate systematically, where each small answer builds into broader understanding.

After mapping what leaders actually do, I realised that a lot of the role involves skills I was already using but never thought to frame as ‘leadership’. That’s different information than “I need five years of training.” After identifying which aspects energise me, I realised the path I was considering would involve work I actively dislike and that I’d need to figure out how to resolve that. That’s also immediately useful information, and I only discovered it by asking questions I could actually answer.

How to break down big questions

The same trap shows up across many, everyday complex decisions, and recognising the pattern helps you spot it in your own thinking.

Take school choice. “What’s the right school for my child?” asks about academic approach AND social environment AND logistics AND future opportunities AND commuting time simultaneously. You’ve got twelve school websites open, three recommendation threads saved, notes from four parents—and still find it hard to move forward. That’s not because you haven’t done enough. It’s because the question bundles too many variables into one idea.

However, “Which schools support children who learn through doing rather than listening?” That’s answerable through visiting classrooms and asking specific questions about teaching approach. “What’s realistic for our commute given my work schedule?” You can map that in a few minutes. “Where would she find children with similar interests?” You can investigate through trial days and conversations with current parents. Different questions, different methods, but each one moves you forward through a process of aggregating small data points into something concrete.

Or take business decisions. “Should I start this business?” bundles market viability, financial risk, skill gaps, and personal fulfilment into one overwhelming question that generates months of research without resolution. But you can answer “Is there demand for this service in my area?” through interviews with local community members. You can answer “What would I need to learn to deliver it professionally?” by analysing competitors and talking to people doing similar work. You can answer “Can I manage financially for six months without steady income?” by running the actual numbers.

Each component question is specific enough to investigate, and the answers accumulate into genuine understanding of your situation.

Why simple questions work

Problem decomposition is the process of breaking complex questions into component questions you can actually answer. It feels reductive because big questions feel appropriately serious. But those comprehensive questions are almost guaranteed to paralyse you.

On the other hand, answerable questions let you make progress where each answer contributes a small part towards your wider understanding. The big picture emerges from investigating components, not from staring at the whole thing.

Next time you catch yourself stuck on a question that’s making you feel incompetent or paralysed, write it down. Then ask: “What are the different variables I’m trying to solve for simultaneously?” List them. You’ll probably find more distinct questions hiding inside.

Pick the most answerable one. Investigate it properly. Then the next. Your understanding builds from specific answers, not from comprehensive questions. That’s not a limitation—it’s how complex understanding actually gets developed.