Procrastination is the Silent Killer of Your Deepest Dreams

Getting what you want starts with the courage to define what you want…

Yesterday we talked about how the normal form of procrastination isn’t as bad as we think it is.

Yes, there’s some stress involved with always brushing up close to a deadline, but most procrastinators always seem to come through in the 11th hour.

But what if there is no 11th hour? What if there is no deadline to kick you into gear?

The answer is that you can procrastinate indefinitely, without even realizing you are doing so.

Dreams Go By

The horrifying thing about this subtle form of procrastination is that applies to matters of critical importance: your deepest dreams and desires.

Maybe you’ve always wanted to travel or to start a side hustle or to write the great American novel, and you’ve always assumed that you’ll get to it “someday.”

Right now there are immediate issues to take care of. Plus you’re not quite ready to start. You’re not exactly sure when you’ll be ready, but you’ll probably know when it happens, right?

One day everything will click and you will start living the life of your dreams.

Someday.

As Tim Ferriss says in the bestselling The 4-Hour Workweek:

“Someday” is a disease that will take your dreams to the grave with you.

Define the Dream

The first step that you’ll need to take to make sure that you don’t procrastinate on your dreams forever is to simply define what they are.

This seems so easy, but it isn’t. You’ll have a sense that by committing to one course of action, you are cutting yourself off from many other experiences.

This objection is actually 100% true, but misguided. By defining and pursuing a dream, you cut yourself off from many other paths that your life could have taken, but almost all of them were mediocre. If you go with the average strategy of reacting to the needs of the present without ever pursuing a brighter future of your choosing, you will get average results. If you want extraordinary results, define the most compelling future you can imagine and move toward it with all you’ve got.

The second reason it is hard to define your dreams is because as soon as you define them, you introduce the possibility of failure.

Like the last objection, this is 100% true. You might fail. Of course, you would also fail if you never defined and pursued your goal, but it wouldn’t feel like failure.

No matter how you look at it, going after your dreams might not work. But the converse is also true: it might work. Defining and pursuing your dreams is sure as heck more likely to work than hoping they happen by accident.

As Charles Duhigg, author of Habit once commented as a guest on The Art of Manliness podcast:

The most successful people are those who are best at identifying their deepest, most important goals.

Impose a Deadline

One of the problems with your dreams is that they don’t necessarily come with a deadline. To get started, you need to impose a deadline on yourself.

This may not be enough however.

In the case of an assignment at school and work, there are real consequences for missing a deadline. There are no consequences for missing a self-imposed deadline.

If you find that you needed the consequences, there are ways to give your self-imposed consequences teeth.

Give some money to a trusted friend. Just enough that it would sting to lose it, and then pick hot button issue that you feel passionately about. Let’s use abortion as an example. Tell your friend that if you meet your deadline, you get your money back. If you don’t, they must give it to an organization on the other end of the aisle.

So for instance, you tell your friend that you want to have a 50,000 word rough draft of your novel done by the end of the year. On December 31st if you turn in a 50,000 word manuscript, you get your money back. If there’s no manuscript or it’s shorter than 50,000 words, your money gets donated to either a pro-choice organization (if you’re pro-life) or a pro-life organization (if you’re pro choice).

Make sure you tie completion of the goal to an outcome you can control (e.g. finishing a manuscript), not one you can’t control (e.g. making a bestseller list).

If you feel pretty good about meeting a self-imposed deadline, you don’t need to go for any special tricks. But it’s worth remembering that these tricks will probably work if you need them. They work in school and at work.

The 10 Year Plan for a Remarkable Life

In 2017 I listened to an episode of the Tim Ferriss show that was extremely influential for me.

His guest was a graphic designer that I had never heard of named Debbie Millman who shared an exercise called the 10 Year Plan for a Remarkable Life.

The idea was to answer a simple series of questions about what your life will look like in 10 Years with the assumption that you won’t fail in turning your dreams into reality.

In other words, it’s a clever way to discover what you really want.

It also serves as your first deadline of sorts.

Humans tend to overestimate what we can accomplish in a day (ever decided to create a to-do list only to realize at the end of the day you had been overly ambitious?), but we tend to underestimate what we can accomplish over time with consistent effort.

The 10 year time frame gives enough time for you to accomplish significant things while being close enough to cause you to realize you need to get started working on them now.

Without the 10 Year Plan I would be at least 30 pounds heavier right now and would not have self-published a book on personal finance earlier this year.

It’s a powerful exercise.

To read more about is and see the questions that I actually answered, you can see the post that I wrote about it:

Memento Mori

We all know the final deadline that awaits us all.

Dumbledore once said that “to the well-organized mind, death is but the next great adventure.” That’s true, but he left off “to the well-organized mind, death is a powerful motivator to accomplish things while you still have time.”

Consider this haunting passage from the psychologist Mihaly Csikszentmihalyi in his book Flow:

As people move through life, passing from the hopeful ignorance of youth into sobering adulthood, they sooner or later face an increasingly nagging question: “Is this all there is?” Childhood can be painful, adolescence confusing, but for most people, behind it all there is the expectation that after one grows up, things will get better. During the years of early adulthood the future still looks promising, the hope remains that one’s goals will be realized. But inevitably the bathroom mirror shows the first white hairs, and confirms the fact that those extra pounds are not about to leave; inevitably eyesight begins to fail and mysterious pains begin to shoot through the body. Like waiters in a restaurant starting to place breakfast settings on the surrounding tables while one is still having dinner, these intimations of mortality plainly communicate the message: Your time is up, it’s time to move on. When this happens, few people are ready. “Wait a minute, this can’t be happening to me. I haven’t even begun to live. Where’s all that money I was supposed to have made? Where are all the good times I was going to have?”

Death is coming for you whether you pursue worthwhile goals or not. You’ll be much more likely to meet death with no regrets if you really took your shot at your dreams.

One of the most powerful quotes I ever heard came from the folk singer Harry Chapin, my favorite musician in my early childhood (link to audio):

My grandfather was a painter. He died at age eighty-eight, he illustrated Robert Frost’s first two books of poetry, and he was looking at me and he said, “Harry, there’s two kinds of tired. There’s good tired and there’s bad tired.” He said, “Ironically enough, bad tired can be a day that you won. But you won other people’s battles, you lived other people’s days, other people’s agendas, other people’s dreams. And when it’s all over, there was very little you in there. And when you hit the hay at night, somehow you toss and turn; you don’t settle easy. It’s that good tired, ironically enough, can be a day that you lost, but you don’t even have to tell yourself because you knew you fought your battles, you chased your dreams, you lived your days and when you hit the hay at night, you settle easy, you sleep the sleep of the just and you say ‘take me away’”. He said, “Harry, all my life I wanted to be a painter and I painted; God, I would have loved to have been more successful, but I painted and I painted and I’m good tired and they can take me away.”

I don’t know whether I’ll achieve my 10 Year Plan or not. I hope I will, I believe I will, but I don’t know that I will. What I do know is that in 10 years I’ll be good tired, and I’ll take it.

The rest is just gravy.

In the words of Andy Dufresne from The Shawshank Redemption:

I guess it comes down to a simple choice, really. Get busy living or get busy dying.

In light of the passages from Mihaly Csikszentmihalyi and Harry Chapin, I would suggest that to “get busy living” means to live in such a way that you are prepared to meet death.

Dying is a default feature of being alive, living is a choice to do something with life, to create order out of chaos, and to leave a piece of yourself behind.

This is the eighth in a series based on my article 30 Lessons About Life You Should Learn Before Turning 30. Shoutout to Dr. Christine Bradstreet 🌴 for the idea to turn the post into an in-depth series.