The Ambition Trap: Why We Don’t Prioritize (and How to Do Better)

After last week’s post about to-do lists, I started to notice a pattern - not just in my own work, but in the conversations that followed.

Most of us know the difference between what’s urgent and what’s important. We don’t treat every task equally. But if we’re honest, we rarely spend enough time truly prioritizing.

And it’s not because we’re lazy or disengaged. In fact, it’s usually the opposite. We’re ambitious, optimistic, and want to believe we can do it all. That ambition creates a quiet optimism gap: the belief that just a bit more effort will make the list manageable. The reality is, as our optimism rises, so does our tendency to say yes - to tasks, requests, new projects, or quick “just a minute” pings.

When Ambition Crowds Out Priority

It’s easy for reactive work to fill our days. The emails, pings, and last-minute asks that feel urgent - sometimes only because someone else says they are. Before you know it, the week’s real priorities have slipped quietly to the bottom of the list.

I’ve come to trust a simple protocol: if something is truly urgent, my phone rings. Everything else can wait, be scheduled, or simply cool off for a while.

Rethinking Progress: Beyond the Checklist

Over the past few months, I’ve been experimenting with a few new habits.

• Setting firmer boundaries on reactive work (batching and time-boxing busywork where possible).
• Carving out protected space for strategic thinking - even if it’s just a single deep session each week.
• Measuring progress less by how many tasks I complete, and more by whether I made space for better decisions.

Second-Order Impact

The impact of our work is often a second-order effect. A week that looks productive - lots of boxes ticked - might not actually create momentum. Sometimes, the best work only becomes visible later, when a better decision, a new approach, or a bit of creative risk starts to pay off.

Daniel Kahneman’s Thinking, Fast and Slow reminds me that quick answers and fast thinking usually reinforce the status quo. Rory Sutherland ’s Alchemy suggests that the biggest breakthroughs come from stepping back and letting yourself think differently - even illogically at times.

Improvement Needs Safety - Not Just Discipline

But here’s what I’m still questioning: Can we really improve our approach to to-do lists and prioritization in a vacuum? It’s one thing to read about new protocols or productivity hacks, but real change is much harder when you’re surrounded by old habits and unspoken expectations.

For me, the most meaningful shifts have come not just from personal discipline, but from the company I keep. Having a trusted peer - a “work husband” or someone who truly gets how you work - makes it safer to say no, to experiment with new routines, or to call out when reactive work is taking over.

Psychological safety isn’t just a buzzword; it’s the foundation that allows us to test new ways of working without fear of judgement. Sometimes, you need that ally - someone who encourages reflection, supports boundaries, and reminds you it’s okay to protect space for deeper work.

Reflection Isn’t a Luxury - It’s the Real Work

Just like most of the heavy lifting happens Monday to Thursday, Friday requires its own kind of discipline - the discipline to pause and critically reflect. It’s the time to step back and ask: What have I actually achieved at work this week? Did I show up for date night? How many times did I make it to the gym?

All of these things - work, relationships, health - are signals that combine to show us where our performance can be tweaked, and where there’s space to grow.

Arguably, this kind of reflection has to happen at work, during the eight hours that are under the most pressure. When those hours are intentional, the eight hours of “social” life run more smoothly, and the eight hours of sleep come easier - because you know you’re performing across the board.

What Works for You?

I’m still learning and iterating. How do you build the discipline to reflect - not just at work, but across all parts of life? What rituals or questions help you spot where to grow next?

If this resonates, or if you’ve found your own way to balance ambition and priorities, I’d love to hear your perspective below.

#Leadership #Productivity #ThinkingSlow #WorkCulture #WorkLifeIntegration