Iâve written three different strategies for problems that never got solved this year alone. Well-researched. Clear recommendations. Leadership agreed they were good plans. Nothing happened. The problems eventually exploded anyway, and I got to be the guy who said: âI told you so.â Turns out thatâs not a win.
You can have all the right ideas, but without execution theyâre worthless. Being the person who predicted the disaster doesnât matter if you didnât prevent it.
The trap of planning
Smart people love planning. It feels productive. You can demonstrate your understanding of the problem, show technical depth, align stakeholders. Writing a good strategy doc is genuinely satisfying.
But planning is comfortable in a way that execution isnât. Plans donât break production. Plans donât require difficult conversations. Plans donât force you to make tradeoffs in real time.
Iâve watched engineers (including myself) spend weeks perfecting a migration strategy while the legacy system gets more entrenched every day. By the time the plan is âready,â the moment has passed. The problem is bigger, the stakeholders have moved on, or someone else shipped a partial solution thatâs now the new baseline.
Iâve fallen into this trap enough times to recognize the pattern now.
What Iâm doing differently
When I see a problem now, I ask: whatâs the smallest thing I can do this week to move the needle?
Not the perfect solution. Not the comprehensive strategy. The smallest concrete action that reduces the problem or proves the approach.
For technical debt: donât write the migration plan, migrate one service. For process issues: donât propose a new workflow, run a pilot with your team. For architectural concerns: donât design the full system, build a prototype that validates the core assumption.
This feels riskier. Youâre showing incomplete work, making decisions without full information, potentially building something that gets thrown away. But incomplete progress beats complete plans.
You can iterate on working code. You canât iterate on a plan that never ships.
The uncomfortable truth
Being right doesnât matter if youâre late. Your strategy is only as good as your ability to execute it before the window closes.
âI knew this was going to happen, we should have done Xâ isnât the flex I used to think it was. Itâs evidence that I saw the problem and didnât act.
Execution beats prediction. Start smaller, move faster, and make the impact before the moment passes.