When you’re feeling overwhelmed at work, your instinct may be to knock out the easiest items on your to-do list just to feel productive—is that right? But that habit can quickly become a trap. In The CBT Workbook for Perfectionism, therapist Sharon Martin notes that “most people are inclined to do the easiest thing on their to-do list,” which is why the most meaningful—often most challenging—tasks stay undone.
We’ve all been there. You start the day checking a few emails, organizing your desktop, or scheduling meetings—all while avoiding the hard thing: that presentation, strategy document, or performance conversation you know will move the needle. The undone task stays in your head. You tell yourself you’ll get to it later. Yes, but the longer you delay, the heavier it feels, reinforcing a cycle of procrastination and overwhelm. You get into freeze mode and end the day feeling like you didn’t accomplish anything. It happens a lot—especially to multitaskers, according to my Time Management Quiz.
To break the cycle, Martin recommends a surprisingly simple solution: do the hardest thing first.
Why You Should Do The Hardest Thing First
When you start with what matters most, especially when it’s hard, you activate focus and build momentum. You also send a strong message to yourself: I can do difficult things. In a recent conversation with a coachee, she told me that being proactive by blocking time on her calendar for what matters most helped her feel more self-respect, and boosted her confidence.
Doing the hardest thing first thing in the morning is especially powerful if your power time, as I mentioned in my previous article, the period when your energy and focus are naturally at their peak, is early in the day. Research shows that cognitive resources are strongest in the morning. As Stanford health psychologist Kelly McGonigal explains it, your willpower weakens as the day progresses, as your energy gets “spent” on stress and self-control. But in the early hours, before meetings and admin work pile up, your mental energy is ready to help you dive into that big task. It’s the best time to make the most of your brain’s natural rhythm.
How To Make This Strategy Work For You
1) Identify your highest-impact task the night before.
What will make the biggest difference if done first? According to the Pareto Principle, 80% of your results come from 20% of your efforts. Focus on those tasks that may take just 20% of your day but drive real progress.
2) Timebox it.
Block off your power hour in your calendar and treat it as non-negotiable. You can reserve this time every day—or at least two or three times a week. People will get used to you being unavailable then. Timebox the specific “hard thing” you identified the night before and add it as a meeting with yourself. You can learn more about timeboxing in my latest book Timebox.
3) Avoid “warming up” with easy tasks.
You’ll be tempted to go back to your old habit of starting with emails or admin tasks. Catch yourself. Timebox those low-value tasks for later in the day—and honor the plan you created.
4) Focus on starting, not finishing.
Commit to just 10 minutes. If you get distracted, tell yourself, “Just 10 more.” It’s the act of starting that builds momentum.
5) Practice self-compassion.
Progress, not perfection, is the goal. If tomorrow you follow these steps and spend just 20 minutes on your hardest task—congratulate yourself! That’s real progress. Try 30 minutes next time.
Doing the hardest thing first isn’t about working harder. It’s about using your energy wisely, breaking the avoidance cycle, and giving yourself permission to move forward with the tasks that matter the most to you.
