Do the Thing You’ll Wish You Had Done

Leave fewer regrets by taking small steps, day-by-day
February 4, 2021 Updated: February 4, 2021

How many times have you looked back and regretted things you wanted to do but never did?

If you’re anything like me, it’s probably more than you’d like to admit. I have a did-not-do regret list a mile long. Some things are relatively trivial, others quite significant.

  • I wish I had worked harder to excel as a college athlete.

  • I wish I had traveled more during my 20s.

  • I wish (and still do) that I was better at staying in touch with family and friends.

  • I wish I hadn’t waited so long to move with my family to the place we now call home.

  • I wish I hadn’t taken on so much student debt during law school.

Every year, as the calendar turns from December to January, I tend to mull over what I did and did not do in the year prior. It may not be the right way to view things, but the “did not do” portion tends to hold more significance. The things I wanted to do but never moved forward on loom larger.

For example, there is a book I want to write—I’ve been talking about it forever—but other than an outline I made little progress on it. Granted, I did write two books last year during quarantine, but not THE book I’ve been meaning to write. There is clearly some form of resistance (almost certainly self-constructed resistance) that’s stopping me from making progress.

And guess what: The book I didn’t write holds more space in my mind than the two I did.

I think, “If I had just devoted a bit of consistent time and effort, I could have at least written a few chapters by now.” And that’s undoubtedly true. And so I regret.

I know I’m not alone in this. In fact, research shows that more people regret things they didn’t do than the things they did, even if things they did turned out badly. This makes sense, since we can’t go back in time and do things we dreamed of doing but didn’t. We’re left only to imagine how life would be different today if we had.

Here’s the good news: We can learn from our mistakes and ward off future regrets by taking action now.

But that begs the question: What action to take?

You may have a hope, a dream, a goal that is audacious. Perhaps you want to write a book, start a business, or lead an untethered, nomadic lifestyle. The enormity of the goal makes it feel overwhelming and you don’t even know how to start.

I’ve felt this way many times in my life. Overwhelm was a constant state for me early in my career as a young lawyer in a large law firm.

I remember plenty of moments sitting at a conference room table with documents piled high around me and Thai-food styrofoam containers strewn about. Too often, I had no idea how to even begin tackling what was in front of me.

As I progressed in my career, I learned to look at my projects like a puzzle. When you’re doing a puzzle, you need to find the corners first. Once you find the corners, the puzzle takes shape. Then you can start clicking the other pieces into place.

When you think of a project (or any ambitious objective) in its entirety, it’s overwhelming. It’s hard to know how to start. You need to break it down into its component parts.

There’s a logical starting point for every project and that starting point helps clarify what else needs to get done and how to get it done. For example, if you’re writing a book, don’t try to start by writing the first chapter. First create the table of contents, and then jot down a few bullet points covering what you’ll say in each chapter. This will feel more manageable, create some positive momentum, and give you a logical outline for the book.

See how this works? When you’re overwhelmed, start with the corners and take it piece by piece.

Also, take it day-by-day. Regardless of what you’re working on, you’ll make little progress if you’re counting on episodic intervals of intense activity. Instead, chip away at it every day and watch the compounding returns on your effort stack up. You can do anything, just not all at once.

But you need to start. Preferably today. Otherwise, you’ll regret it.

Jay Harrington is an author, lawyer-turned-entrepreneur, and runs a northern Michigan-inspired lifestyle brand called Life and Whim.  He lives with his wife and three young girls in a small town and writes about living a purposeful, outdoor-oriented life.