Entrepreneur Insomnia: 12 Things to Try When You Keep Waking up at Night

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Waking Up in the Middle of the Night is NOT Fun

It was 1am and I was sleeping just fine, and then I got up to use the bathroom and it happened….

….entrepreneur insomnia.

I got back in bed, thought I could totally fall back asleep…but I was awake pretty much from that point on.

The thoughts just started flowing:

  • “I should totally use this kind of audience for X client’s next Facebook ad”
  • “THAT topic would be a killer blog post”
  • “Wait – did I actually send that email, or is in just sitting my drafts folder?!”
  • “It’s been 13 hours and we haven’t gotten a single Facebook lead. WHYYYY?!”
  • “Am I sharing enough to help people on Hustle to Startup? Maybe I should change my approach.”
  • “Ohhh, another good blog post idea.”
  • “Okay, now it’s 2am, only 2 hours until I have to get up anyway. I should just get up now and start writing.”
  • “NO stay in bed. You can’t work efficiently if you’re exhausted you idiot.”

And on….and on….and on…..

If you’ve been to this site before, you know that I wake up extremely early– i.e. 4am on most days.

3 or 3:30am rolled around and I must have fallen back asleep, only to be awoken by my alarm at 4:00am.

“Oh no, please no…..”

And I reset my alarm to go off at 4:30am….

If you know me, you know that I do this about 0.05% of the time – AKA it’s very RARE.

But I was exhausted. And I was recording a podcast with Jeff Sauer later that day so I knew I needed sleep. I mean, he’s interviewed the likes of Rand Fishkin, Oli Gardner and so many other awesome search marketers…I’m nowhere near that category, so this was kind of an important day.

I was EXTREMELY thankful that I am my own boss that next morning, because I totally took a nap from 8:30am to 10:30am. :O

Safe to say that was not the best sleep I’ve ever had, and it’s not the first (or the last time) it will happen. But I’ve decided I need to find some kind of solution to this. Here are the strategies I’m going to use to try and mitigate this from happening in the future.

1. NOT look at my phone at least 30 minutes before bed.

I have this tendency to scroll Twitter or Instagram right up until I close my eyes to go to sleep. I’m pretty sure this is a common thing, but I need to stop doing it.

Plus I have this inkling that wifi or bluetooth or something causes harmful side effects, so that doesn’t help.

The only downside to this one is that if I wake up in the middle of the night and have great ideas, or reminders floating around, I have nowhere to put them. Which leads me to number 2…

2. Leave a Notebook On My End Table

Sure, I’ll have to squint to try and write down anything in the dark, but I’m sure I can figure it out.

Like I mentioned above, there are SO many things that go on in my head right before, or during, sleep that I need somewhere to put them all.

3. Read Fiction or Memoirs Before Bed

I am NOT a fan of fiction – I love diving into business and personal finance books, it’s just not my thing to read “stories.” But I’m going to give this whole fiction thing a try. I used to love reading books like Tuesdays with Morrie or The Lovely Bones when I was in college.

But then I kind of stopped reading, and it wasn’t until about 5 years ago that I started up again. Since then it’s all been self-help, personal finance, and business. I’m not kidding. ALL of the books I read fell within those 3 categories.

So I’m going to give this fiction and memoir thing a try again. After all, if my mind is racing with business ideas in the middle of the night, it probably doesn’t help to be reading about that stuff before bed.

If you have any suggestions, feel free to pass them along! 🙂

4. Turn Off or “Hide” Those Blue and Green LEDs

The light that comes from the nightlight in the hallway – or green light coming from the alarm clock are seemingly so small, but in a dark room they can really affect the balance. I’ve been sleeping with the door closed the last few nights, and that’s helped. I also decided to put a sock over my alarm clock last night (good enough!).

Another tip is that even if you have your phone on silent, flip it over so if it lights up in the middle of the night, you aren’t getting distracted if you happen to be half-awake.

5. Brain Dump at Least Once a Week

I love the act of doing a brain dump. It might have a weird name, but if you’ve never heard of this, essentially you open up a blank document on your computer – or get out a fresh sheet of paper – and then you just started making lists of everything in your head.

These can be personal thoughts, business, work, family, ANYTHING. The idea here is to get all of those thoughts you keep having out of your head so your brain doesn’t have to keep reminding you of them. It’s a very powerful exercise to do if you’ve never done a brain dump.

Mine usually end up being 2-3 pages long, but I honestly haven’t done one since I quit my day job in June of last year. :O

I’m adding this to my calendar now. Here it is:

brain dump calendar reminder

If I didn’t add the “REQUIRED” part I’d probably allow myself to skip it. But it’s important, so I’m going to try and keep the habit.

6. Buy a Better Quality Bed

This one is something I’ve been against for a while, we have a great bed, why fix something if it isn’t broken? But reading this article by Peter Shallard made me question why I was so against it.

“Invest in quality equipment. You’re an entrepreneur, so your time is precious. Not only are you spending a third of your life in bed, the quality of your experience there determines your bottom-line output the rest of the day. So optimize your experience.” – Peter Shallard

Well that makes a whole lot of sense! He’s right, and so is my girlfriend. She’s been mentioning this for a little while, time I started listening 🙂

7. Drink Chia/Spirulina Earlier in the Evening

Okay, I’m about to let my hipster flag fly – I drink a concoction of chia seeds and spirulina/chlorella every night before bed. Yes, it looks like I dunked my cup in a dirty green lake and started drinking it.

It was disgusting at first for me, but I’ve grown to love it. It helps with pulling heavy metals out of your body, and really helps make my mind feel more clear (yes, this is extremely ironic, I know).

ANYWAY – I usually drink this about 20-30 minutes before bed. I always tell myself I need to drink it earlier, but never end up doing that. Well now I’ve set a phone reminder (oh the almighty reminders app) because I cannot afford to be waking up at 1 am to run to the bathroom and repeat this “no sleep” cycle again.

For those of you non-hipsters, replace the chia drink with water, and try not to drink a lot of it before bed.

Other Ideas I’ll Try in the Future:

8. Meditation

I’ve tried this before and have not had success in going more than a few days in a row. Headspace was a great tool, but I just couldn’t get past day 4 or 5.

9. Exercising More Regularly

This one is something I may end up doing sooner, but need to find a better schedule. Many people say they sleep better when they work out at night, but I always end up laying in bed wide awake if I workout after 6pm or so.

But exercise is such a great way to not only get rid of extra energy, but also to help you think more clearly and get those pesky thoughts out of your mind (before 1am rolls around).

10. Not Drinking Coffee after 3pm

I usually don’t do this one, but occasionally I want something other than water and enjoy coffee a lot so I give in. But apparently there is a link between coffee late in the day and grinding your teeth at night – which I’ve been told that I do. Whoops!

11. The Chilipad

This is a pad you put under your sheets that keeps your side of the bed at a constant temperature and apparently helps you fall right asleep. It’s kind of pricey so I’ll probably hold off a bit longer on this one, but it looks pretty cool! (pun intended).

chiliPAD Cube 3.0
  • ME and WE Zones
  • Cooling and Heating Mattress Pad
  • Individual Temperature Control
  • Great Sleep Enhancement
  • Wireless Remote Integration (Single (75" L x 30" W)

12. Another Hipster Type Drink

This one isn’t as crazy as the chia and spirulina drink, but still seems a little out there. Here is the recipe:

  • 2 Tablespoons of Apple Cider Vinegar
  • 1 tablespoon of raw honey
  • Mix it together in a glass of warm water
  • Drink it before bed!

Apparently it helps keep blood sugar consistent throughout the night.

Tim Ferriss and Chase Jarvis discuss this and the Chilipad here:


I may be great at waking up early, but I’ve got a LOT to learn about staying asleep every night. What tips work for you that I missed? Are you going to try any of these?

1 thought on “Entrepreneur Insomnia: 12 Things to Try When You Keep Waking up at Night”

  1. I’m going to do something I haven’t done in years — comment on a blog post! I was going to text you, but then I had so much fun writing a “diary style” post yesterday that I thought I’d keep it in 2011 over here too. 🙂

    MY SUGGESTION: When you know, really know, that you’re not going to get back to sleep, roll with it. Get out of bed, do the work, write the blog posts, check to see if you sent that email, then let yourself go back to sleep. I did that once, and made a killer opt in at 2am. Had to nap at 2pm, but you know… #bossthings. 🙂


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