Define Success on Your Own Terms

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That if one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.

Henry David Thoreau

You probably remember Henry David Thoreau for his amazing literary works.

Chances are you haven’t heard of A Week on the Concord and Merrimack Rivers.1

In 1839, Thoreau and his brother John made a boat and hiking trip from Concord, Massachusetts to the White Mountains of New Hampshire. When John ended up passing away a short time later in 1842, Thoreau set out to recreate the trip in novel form.

The only problem? No one wanted to buy it.

Thoreau paid out of pocket for the first run of 1,000 books. Only 300 were sold leaving his publisher with a backlog of 700 books.

One might expect him to have felt disappointed with the book’s success. Quite the contrary. He expressed nothing but happiness having 700 books that he penned himself stacked high in his library. In his journal, he was quoted as saying:

I have now a library of nearly nine hundred volumes, over seven hundred of which I wrote myself. Is it not well that the author should behold the fruits of his labor? My works are piled up on one side of my chamber half as high as my head, my opera omnia. This is authorship; these are the work of my brain.

If Thoreau’s litmus test for success for his book had been “become a best-seller”, he would have felt dejected and demoralized after only selling a handful of books.

But, it wasn’t.

He defined success as something different. He was happy sharing this memory he had with his brother, John. He was happy just putting the “works of his brain” out for everyone to see.

Chasing More

Jon Goodman has a freedom number. It’s $2,600 2.

That’s the amount of money that Jon has to bring in every month to be happy and do the things he loves to do. How much do you need?

I’m going to go out on a limb and guess that you probably don’t have a freedom number at all. Perhaps you have an idea in mind but you don’t have a goal set in stone.

Instead, most of us are following the herd mentality and chasing “more”.

$2,600 a month would be great, but you know what would be better? $3,000.

I absolutely love my three bedroom house, but I can’t wait to get a bigger one.

The problem here isn’t necessarily the pursuit of more. Rather, it’s the delay of enjoyment in the current moment. If you’re constantly chasing more, you’re setting yourself up to consistently be disappointed with what you have right now.

The Solution

Routinely define success on your own terms. If you don’t define what success means to you, you’ll constantly be chasing what it means to other people.

Instead, every month, sit down and make a list of what you would need to be happy. Then, identify how that’s different from where you are right now. The difference between those two points becomes your action plan.

Here are some things that made it onto my success list:

I am happy if:

  • I’m sharing something that I feel has value
  • I’m constantly pushing myself to have new experiences
  • I have enough money to pay the bills and eat a few nice dinners each month with my lovely (almost) wife (I have a firm number in mind)

Once you have those items laid out, any efforts that don’t directly translate into those items are wasted energy.

The best part? You’ll find that many of these items are actionable right now. In my particular case, I started to write regularly and publish work here. Charlotte and I started planning a trip to somewhere we’ve never been.

Defining your own view of success is a clarity exercise that helps direct your action to what really matters instead of chasing something that matters to everyone else.


1. A big thanks to Maria Popova of Brain Pickings for sharing Thoreau’s story here and sparking this idea. This book has also been republished numerous times so you may have heard of it. The point is that it was a “failure” for Thoreau at the time. 

2. Jon shared this in a Facebook update on his page here. He’s a really smart dude. I would highly recommend following along.

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