Warning: Some of these methods are dangerous & may cause negative repercussions in your life — they may also make you wildly successful.

If you’d prefer to watch the video instead:

I’ve had high expectations for myself my entire life.

Sometimes, higher than my level of discipline, or ability to follow through when it comes to goals that I’ve set for myself.

And while some productivity tricks have been helpful for getting me over the hump, I knew I needed something more… powerful… to keep me working towards my goals and stop laziness and procrastination from winning.

I went looking for seriously effective methods for accomplishing goals and what I found was powerful and dangerous. I’ve compiled them into the guide you’re about to read.

This is the Dark Productivity Playbook.

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Negative Incentives

Positive incentives are for children and type-A overachievers.

If you have issues following through on goals you’ve set, you need something outside of yourself to keep you on track when your lazy ass decides to play Xbox instead of write a newsletter.

(That last part might be a bit of self-reflection…)

Negative incentives are the pinnacle of Dark Productivity.

In order to do the impossible and tackle huge goals, you need to make it so that the pain of failure is far greater than the pain of the work required to succeed.

Inaction is a slow death and there is usually no immediate consequence for slacking off and not pushing yourself hard to achieve your goals. Most people regret not achieving their goals or not following their dreams very late in life. Laying on their deathbed wishing that they would have done more or tried harder.

With negative incentives, you can speed up the “Pain of inaction” and give yourself a tangible reason not to fail. Here are a few examples:

Financial Punishment

The most basic, yet effective, method in the Dark Productivity Playbook is financial punishment.

If I told you that you had to write a 100-page book in an hour or you’d lose $20, you probably wouldn’t end up writing that book.

But if I said to you that you had to write a 100-page book in an hour or I’m taking every single dollar in your bank account, you’d write faster than you ever thought possible.

This is what websites like StickK and Beeminder are designed to do.

Set a goal, make a commitment, and set your punishment for not following through. (For bonus motivation points, commit to donating the money you lose to a charity you disagree with.)

And no, this doesn’t mean you have to stake your life savings to trick your work ethic into going warp-speed, you only need to make the pain of failure worse than the pain of the work required to succeed. I’ve used this strategy in the past and sometimes it only takes a little bit of money on the line for me to get my ass in gear.

This method is pretty effective but there are other things that can stop your progress…

Embarrassment, Pride, and Ego

One of the main reasons we fail to achieve our goals, especially audacious ones, is fear.

Fear of failure, fear of success, fear of pain, death, humiliation, and judgment — stop us from doing what we are truly capable of... But there is an antidote to this.

Our psyches are very fragile in the face of attacks on the ego.

Essentially, you’ll feel shitty when people think you’re a loser whether it’s true or not. Luckily you can use this to your advantage and set up situations that make it very hard for fear to stop you from accomplishing your goals.

I started learning how to skateboard 2 years ago and I’ve always been terrified of dropping in on a quarter pipe.

I stood at the top of that ramp so many times. Again and again, I would get scared and have to slide down on my ass in self-defeating embarrassment.

In life, you need something to FORCE yourself down that ramp…

So I invited my girlfriend to the skatepark to record me while I dropped in for the first time. Essentially forcing me to commit… or have my ego shattered by doing the slide-of-shame in front of the woman I love.

While it still took at least 5 full minutes of me standing at the top adjusting my skateboard, I overcame my fear and dropped in.

You can leverage your insecurities and get yourself to do things that you never thought were possible (no matter how clumsy or uncoordinated you are...).

But if you want to get really crazy with it, you can go even further…

Public Commitment

One surefire way to get you moving on your goals is to stake your reputation on it…

I’ve wanted to consistently make video content for years and have failed so many times. I tweeted this commitment to uploading a video every week for the rest of the year and right now, if I break that promise I’ll have to pay close to $1,000 and my failure will be very public.

This doesn’t just put a financial incentive on you, but something about the possibility of other people hoping for your failure gives you an underdog complex that allows you to follow through even when you're struggling with willpower and motivation.

Betting on yourself is cool. But proving wrong the people who are betting against you is even cooler.

Full disclosure… I failed that challenge 4 weeks in. But in that time I made 4 videos that I was proud of instead of making 0. And to those of you who I still owe money: I won’t forget you.

You can follow me on Twitter here for more potentially lucrative failures.

Memento Mori

Let’s say that NASA announced that a giant asteroid was headed for Earth and all life on this planet would be extinguished in just over 2 weeks…

What would you do?

What about if the asteroid was going to hit in one year? 10 years? 50 years?

This “asteroid” IS coming.

We all act like we weren’t given a death sentence the day we came into this life and in turn, forget to act with the urgency a gift this amazing demands.

Time is ticking down to the moment when the proverbial asteroid will hit and erase our consciousness from this world. While grim, it’s a powerful reminder that we should never allow a thing to be undone or a dream to be unchased.

Memento Mori is a Latin phrase that means “remember that you will die.”

It’s a reminder of our mortality, which can help us break the cycle of laziness and procrastination. The finitude of life makes things more valuable and should give you the urgency to live a life that you would be proud of. This life is borrowed and we do not get to pick when we have to return it.

Before you’re gone, push yourself, realize your potential, and do cool shit that you would be proud of. Remind yourself of this every day.

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Thanks so much for reading another issue of The Jailbreak!

Til next time, Nomads. ✌️

- Jack Ross

Chat with me directly by replying to this email, follow me on Twitter for regular updates, and subscribe to my YouTube channel for travel vlogs, tips, and insights on unlocking freedom in the digital age. ❤️

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