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How-To Guarantee a Nightmare Filled Sleep

November 15, 2007 by Ben Yoskovitz

bloodshot eye

Who doesn’t enjoy the thought of tossing and turning all night in fits of restlessness brought on by nightmares? Woohoo!

The secret is this: Work right until the moment you go to bed.

It’s really as simple as that. Work, work, and work some more. When you’re exhausted, go straight to bed (don’t pass GO!) and try to sleep. I can guarantee a night filled with nightmares.

The nightmares will almost certainly be work related:

  • Your boss turning into a mutant killer.
  • Forgetting your entire presentation while standing naked in front of a crowd that’s throw garbage at you.
  • Unfinished tasks and to-do lists running through your mind over and over and over and over, driving you insane.
  • Losing out on a big client or project because you forgot to do something.

The possibilities are endless. And unpleasant.

Lately, this has been happening to me all too often, brought on by an immense amount of work and increasing pressure. Ah, the joys of stress!

Die work-life balance! Die! Die!

Such is often, unfortunately, the mantra of the startup entrepreneur (or the freelancer) that’s trying to do everything at once and build up something immensely successful. It’s a shame, but it’s often reality.

I would never suggest you stop working at night. As nice as it would be not to have to do so, it’s simply a reality of life. Instead, here are my suggestions:

  1. Do a brain dump. Just before you’re going to stop working and about to collapse, do a brain dump of things to remember, and accomplish the following day. Throw it on a piece of paper. Spit it out. Just get it out of your head. It serves as a “closing point” for the day’s efforts, even though so much is left unfinished. (Brain dumping at the beginning of the week might help too.)
  2. Take time off. After the brain dump don’t hop right into bed. Take at least 15-30 minutes off to do something mindless – watch a bit of TV (preferably not something like the Exorcist) or read a magazine. Find something that’ll get you to laugh…because laughing is a great way to relax and take your mind off things. Or go for a little bit of inspiration. You don’t want to think, you want to be distracted. And it’s OK to get distracted, you won’t forget anything for the next day, because you did the brain dump.

No one wants nightmares (far as I know), but jumping from your keyboard to your pillow without pausing for a moment and consciously preparing yourself for the best possible sleep will lead to all kinds of nightmarish trouble.

photo by The Tidal Rabbit

Filed Under: Personal Development

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Ben Yoskovitz

Founding Partner at Highline Beta, a hybrid venture studio and VC firm that works with large, ambitious companies to identify new areas of opportunity through internal and external innovation.

Previously I was VP Product at VarageSale and GoInstant (acq. $CRM), and Founding Partner at Year One Labs.

Angel investments include: Breather, Spoiler Alert, SendWithUs and others.

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