Why You Should Never Start With Your Most Difficult Task

(And What You Should Do Instead)

Years ago, I heard a motivational speaker encourage his audience to “eat that frog.” The line has a long history. And it makes sense: Stop procrastinating and just do the thing you fear. Once you do that, everything else is easy.

While that may be helpful in overcoming procrastination, it’s exactly backwards for big goals and projects. Instead, you should tackle your easiest task first.

Start with the Easiest Task First

When I wrote Living Forward with my friend Daniel Harkavy, we spent two days together talking through the content of the book. We determined that the book should consist of ten chapters.

Because I had written several books before, I volunteered to write the first draft of the manuscript. When I sat down to actually start writing, I did what I always do when writing a book-length manuscript: I started with the easiest chapter first.

Once I completed that, I moved to the next easiest chapter, then the next, and the next. After twenty-nine days, I had completed nine chapters. The only chapter left was the big, hairy one I had dreaded at the beginning of the project.

Initially, I was afraid to write it. In fact, I wasn’t sure I could. But by the time I had finished nine chapters, I was confident I could. That chapter was the only thing standing between me and finishing the book. I literally wrote it in one day.

Embrace the Comfort Zone

In my course, 5 Days to Your Best Year Ever, I teach people that you can set your goals in one of three zones:

1. The Comfort Zone
2. The Discomfort Zone
3. The Delusional Zone

I then argue you should set them in the Discomfort Zone, where you experience some level of fear, uncertainty, and doubt. Why? Because these are the goals that prove to be the most compelling over time. This is also where all the really good stuff happens.

I then explain that you should avoid the Comfort Zone as well as the Delusional Zone. Both are counter productive when it comes to setting goals.

However, the way to tackle a goal that is in the Discomfort Zone—one that makes you feel fear, uncertainty, and doubt—is to start with a task that is in the Comfort Zone. Why?

3 Reasons to Go from Easy to Hard

There are at least three reasons I find it helpful to top-load my task list with easy items.

1. Motion. The first step on any project is usually the toughest. But when you start with the easy steps, you lower the threshold for taking action. This is how you trick your brain into starting.

2. Emotion. Getting some quick-wins boosts your mood. According to researchers Francesca Gino and Bradley Staats,

[F]inishing immediate, mundane tasks actually improves your ability to tackle tougher, important things. Your brain releases dopamine when you achieve goals. And since dopamine improves attention, memory, and motivation, even achieving a small goal can result in a positive feedback loop that makes you more motivated to work harder going forward.

That’s exactly what happens for me. My excitement level actually goes up as I work.

1. Momentum. Getting started and feeling good about your progress means it’s easy to build momentum—just like I did with my manuscript. Gino and Staats say checking items off your list frees up mental and emotional energy to focus on other projects. You might also find the tough items get easier as you go.

The opposite is also true. When you start with the hardest projects first, you can drain your mental and emotional energy. Now you’re lagging—and still looking a handful of small jobs on your to-do list. Now the easy looks hard. It’s a momentum killer.

This is how I personally attack any big project or goal. I start with a task so small and so easy I can’t fail. I then use that as a foundation to progressively take on more difficult tasks.

I even approach my daily to-do list this way. I start with the easiest task first, then move to the next easiest, and then finish with the hardest.

You have to be careful you are not using this as a way to procrastinate (which is the real message behind the eat-that-frog advice). But assuming you aren’t, it’s a great way to defeat fear, and achieve some really big outcomes.