10 Ways I Deal With My Own Procrastination

It’s important I address several things first before I really start into the meat of this article.

First, when I tweet about this post many people will respond, “I’ll read it…later” or some variation of that.

That’s a funny joke. I get it.

Second, while I was writing this post, I procrastinated pretty heavily. No surprise.

And what was even better, I employed almost all of the techniques below to get over the procrastination and still be very productive.

In fact, one of the techniques I mention below is to start in the middle.

It’s worth mentioning then that the words I am writing now I am writing after already finishing the article.

So here are the 10 things you should do to make your life more productive via procrastination.

Plan B

Make a list right now of 10 things you can do that will make you feel “productive.”

If you ever feel like you are procrastinating, then just go down the list and do the tiniest thing you can do for each item on the list.

For instance, if I am procrastinating writing on a book I can take a break and start sending emails to potential podcast guests.

I procrastinated on writing this post. So I even responded to emails from six months ago (that I procrastinated on responding to then).

Do you know what? The respondents appreciated it and I kept those business connections alive.

I also read parts of a book to prepare for a podcast next week.

Or it doesn’t even have to be something related to “business productivity.” I can exercise, for instance. That will probably improve my ability to focus better in the long run.


If you feel procrastination is becoming a habit, then take a step back and change your life.

Whenever I’ve been deeply unhappy in my life, I play games. I play games ALL DAY.

Games are actually good for you in general. They make you strive to improve. They improve various brain functions (spatial reasoning, problem solving, etc). They improve your ability to deal with failure (since often you will lose) and learn from your mistakes (if you study what you did wrong in lost games).

But games can also be escapist. When I’ve been unhappy in relationships or in a job, I play games all day long.

I was afraid to get married in my first marriage. I was scared I was too young.

20 minutes before I was supposed to be at my own wedding, I was at my office and hadn’t changed yet.

I was playing one minute chess (each side takes one minute, if one player runs out of time before the game is over, then he loses) against the Swiss Chess Champion. I was winning. I figured, “I can’t stop doing this. I’m winning!”

That was bad.

Escapist gaming is no good.

One technique i do now to take a step back is:

no drinking

  • go to sleep around 9pm and wake up at 5am and get out of the house to read or write or walk.
  • try to do productive gaming instead of escapist gaming. As long as I focus on improvement, it will make me better able to focus on the task at hand.
  • OR, I try to play in some way. I recommend Charlie Hoehn ’s book on PLAY to see how he used it to decrease his anxiety and become more productive.


The word of the month for me seems to be “experiment.”

Everywhere I look I seem to be reminded of the importance of this.

A great example is Chris Rock. He’s a funny guy. He goes on stage, does his act, and everyone laughs. Again and again.

But that’s not how he starts. He goes to “The Laugh Factory” in my home town of New Brunswick, NJ and takes some crumpled notes and just starts reading them out loud in his regular voice.

If people start to laugh on a joke, he knows he has something that can be developed. If people don’t laugh, he throws that joke away.

He experiments with 1000s of jokes before he has an hour of material that a year later he can use on an HBO special.

If I am working on a project that is stagnating and I don’t feel like working on it, I try to back up one step, try a different direction.

Experiment to see if this excites me more.

When I first started a company, we weren’t sure the best way to make a lot of money.

So we experimented. We made software to see who would buy it (nobody). We started a record label (we almost signed one act and then they disappeared). We thought about starting a database for people in the entertainment industry (then IMDB came along).

We thought about making an automatic website developer but it was a lot of work (think…Wordpress).

We even thought about making a tea company but we knew nothing about distribution.

But it wasn’t bad to experiment. Learning about each of these businesses gave me useful information.

For instance, ten years later the lessons learned from how to start a tea company was useful in making a fund of hedge funds (you send out your tea/money to distributors/other funds and once a month you collect information from everyone and compile the data. Similar risks occur in each business.)

The ways we explored making money on the Internet in 1996 helped in 2009 figure out what were the best things to invest in with the sharp rise of social media.

And even experimenting with a record label enabled us to land the job of doing the websites for many record labels (Loud, Bad Boy, Interscope, Jive, etc).

When I am less productive with writing now, I try to figure out how to experiment with the form a bit more. Or be creative in some other way. Then I consider it a good day.

While I was procrastinating on this article I wrote both the first and second draft on a children’s book, an experiment I have never done before.

Smaller Is Better

When I am procrastinating on a book I take a step back and STOP THINKING about the whole book. I just try to outline what I want to accomplish with the exact page I’m working on.

The process is:

  1. find a smaller task within the bigger task
  2. outline it
  3. set a mini-deadline for doing it.
  4. drink coffee
  5. DO

For instance, I procrastinated for a few days on this very post. And then I procrastinated this morning on it.

First, I did my “PLAN B” as described above.

I responded to some emails. I sent some thank-you emails. I comment on posts in various Facebook groups I’m a member of (including the “Choose Yourself” group).

Then I got into this post and I felt a bit overwhelmed (“DO I REALLY HAVE 10 THINGS?”).

Finally I said, “do one thing” – So I thought a little harder on all the times I’ve procrastinated (since the only good advice is ALWAYS autobiography) and remembered that I always break down big tasks into smaller ones and wrote this part (“smaller is better”).



Nothing to say here.

It’s just important to remember: anxiety will never solve tomorrow’s problems and will only steal away energy from today.

Surprise Myself

When I was talking to Derek Sivers on my podcast he mentioned a trick he does for TED talks. “Always surprise.”

I love that.


The thing with procrastination is often I am bored with what I am doing. If something is not interesting to me, I have a hard time finishing it.

So I try and surprise myself. If it’s a writing project I try to think of the most outrageous thing that has happened to me recently and put it down on the page.

And when I put it down on the page I try to start with a word that is a surprise to me.

Like I might start a post, “But then I forgot to tell you about the time the police picked me up and forced me to stay at a motel at the edge of town.”

If you can surprise yourself, it’s a guarantee everyone else will be surprised.

Hopefully in a good way. The “but” “forgot” and “police” all bring in the elements I need. Now I have to unwind them to tell a story, which postpones the procrastination.

Start In the Middle

Starting a new project is often the hardest part.

So start in the middle so you don’t have to worry about the “official” start.

This reminds me of a Neil Gaiman graphic novel, “Black Orchid.” There’s a superhero, the Black Orchid, that “stars” in the comic book.

BUT, right in the first few pages she is shot and killed. And that’s it. She doesn’t come back.

What a genius thing. To kill the hero in the beginning. To create a pseudo-climax right in the first few pages. it’s almost like he started at the end.

I started this post with the list. Then I will go back and write the beginning.

And, by the way, the last line I wrote in this post was this one.

End In the Middle

Ernest Hemingway would anticipate his own procrastination when writing.

He would sometimes end a writing session while in the middle of a sentence, or paragraph. Then he would be more excited (and be more aware) of starting up again when he came back.

For instance, if you are a programmer, end right in the middle of an “IF” statement before putting in the “THEN” part.

[I just did the PLAN B technique again for the past ten minutes. Scheduled a lunch. Responded to one email and posted a few comments in the “Choose Yourself” FB group.]

Redefine the Project

This is similar to the breaking it down into smaller chunks EXCEPT…actually change the project so it is smaller.

When I was building the website, Stockpickr, which I eventually sold for significant money to thestreet.com, I launched with only a few features.

I had planned for many more. But it feels good to “launch” and I wanted that good feeling.

The same thing can happen now with other types of projects. For instance – books. The definition of a “book” used to be mandated by the big publishers and big bookstores, i.e. 200-250 pages and 60,000 – 70,000 words.

Now this is out the window. Amazon and the rise of self-publishing has thrown out the definition of what a book is. I was just looking in the Entrepreneurship category where my 270 page book, “Choose Yourself” is #2. I sweated over that book for years.

#1 in the category is a 24 page book probably written in a week. Power to him. He had a solid idea, he wrote it up, he published it, and now it’s #1 in the category. A person can do that every month and write 12 books in a year and make a living that way.

Another time I was moving into a house I had bought (the last one I will ever buy and has long since been sold).

The construction workers wanted six more months to work on it. I said, “no” and moved right in. They felt so awkward with me right there that they finished up in a week.

Was it completely finished? No. But then bit by bit I was able to hire people to finish what was needed.

Launch first, then finish.

[PLAN B again – I just made two idea lists: “10 things that I want to see virtual reality do” and “10 TV shows/movies that have ‘Choose Yourself’ characters in them].


If I’m making a list like this. Or writing a post. Or planning a project, I often get inspiration in the middle by reading.

I’ll go back and forth between inspirational books, informative, or well-written. One of them will inspire me back to what I’m doing.

I can never underestimate the ability to absorb someone else’s life by reading about it. I’m a vampire sucking out their knowledge and making my brain more powerful.

This morning, (in between the beginning of this post and right now), I read from “The Stranger” by Camus and “Better, Smarter, Faster” by Charles Duhigg (coming soon on the podcast).

Give Up

Not every project is meant to be finished.

The reason you might be procrastinating is because your body and mind might know that the project is simply no good but they have neglected to tell you that yet.

One time I started a company, built a site, and raised $500,000 for it. I’ve written about it before so won’t go into the details of the company.

But it was a bad idea. I woke up the day after raising the money and I was shaking. I literally didn’t want to get out of bed and start to work on the site.

All I keep thinking was, “this is a bad idea and a year from now I’m going to have to explain where all the money went to all of the investors.”

So I ate the cost I had already put into building the website, I wired back all of the money, and shut down the business.

There’s a cognitive bias called “The Sunken Cost Fallacy” that applies to procrastination.

When we put time (or money) into something, our brains feel like, “Ok, that’s it. Now I have to finish this.”

But it’s just not true. We don’t have to finish anything.

Often it’s good to take a step back and wait a long time (months or years) or simply give up.

This is why it’s good to have other projects on the burner as well. Always make sure that no one project will kill you if you procrastinate on it or take a several month break from it, or even not finish it at all.

In fact, it’s always good to have about five projects (no more and no less) going on at the same time. This gives you constant fuel as you go back and forth. You won’t create your way into a hole with just one project and you won’t feel overwhelmed with too many.

“Giving up” is often the most productive and efficient thing we can do in our lives to move onto the things that are more rewarding in the short amount of time we spend in this crack of light between two infinite darknesses.

I procrastinated a lot on this post. I procrastinate on everything. On all 18 of my books. On all 20 of the businesses I’ve started.

In fact, this post is the result of procrastination. I am actually working on a post: FAQ ON QUITTING YOUR JOB.

But I am procrastinating on that post by writing this post. This was my “PLAN B.”

Sometimes I procrastinate calling people back and then I end up feeling guilty and never calling them back.

And there are things I am mid-procrastination on right now that I might never finish.

Who cares?

When I die those projects will remain unfinished forever.

But when I die my kids and loved ones will be crying for other reasons.

Or not.

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