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Entrepreneurial Insomnia: How to Shut Off Your Brain When You Can’t Stop Thinking

Entrepreneurial Insomnia: How to Shut Off Your Brain When You Can’t Stop Thinking

There’s a topic I can count on 100% of my clients to bring up at least once during my tenure as their therapist: Sleep and insomnia.

Entrepreneurs tend to suck at it. We pat ourselves on the back when we quit the 9-to-5. It feels great, but comes with nasty side effects that kick in around 11pm – running your own business is stressful.

Maybe you lie awake with a million ideas spinning around your skull. Maybe you doze off and jolt awake, desperately trying to make yourself not forget some important detail. Or, maybe you’re just worried and you go to bed thinking dark thoughts about your business future.

Self employment and good sleep is NOT a mutually exclusive choice you have to make. This article breaks down everything you need to simultaneously captain your own ship and get a fantastic night’s rest. 

You may not realize just how important sleep is

The gung-ho hack-all-night attitude of startup culture isn’t a smart one.

I’ve overheard macho entrepreneurs in NYC coffee shops proudly one upping one another over who’s slept less. Meanwhile, some famous entrepreneurs run insane experiments on themselves with the explicit goal of radically cutting down their eight hours.

Even if you’re not actively attempting to limit your sleep, you’re probably not sleeping as well as you should be.

Dr. Charles Czeisler, a Harvard sleep researcher, has proven that getting four hours of sleep for five nights in a row has a similar impact on memory, attention, and thinking-speed as being legally intoxicated.

Though Dr Czeisler’s study results may not conform to a standard curve, it’s fairly safe to assume that even a little less than adequate sleep, repeated nightly, will eventually result in the kind of ineffectiveness you might expect after a lunchtime beer or two.

Which is all to say: Sleep is really important for the kind of mental function you need as an entrepreneur. You might be able to “get by” with less than ideal, but it means you’re working hard… not smart. 

9 tips on how to sleep smart and work better than ever

1. Re-evaluate your relationship with caffeine 

If this wonder drug is your preferred entrepreneurial productivity tool, it could be massively contributing to insomnia issues. Even if you’re not drinking coffee in the afternoons and evenings (if you are, stop), the withdrawal symptoms you experience while you’re sleeping at night can result in teeth grinding and all kinds of nasties.

And if you’re waking up with a need-coffee-NOW headache, your sleep quality isn’t as good as it could be. If you want a productivity fix without the caffeine, check out Commit Action.

2. Check what you’re eating before bed 

I can’t not mention this, even though I’m supposed to be psychologically focused. If you’re eating high sugar foods before bed, you’re going to give yourself a sugar rush that’ll mean you toss and turn longer than you should be. Cut the sugary snacks and try good-fats and protein (hard boiled eggs work great) if you need to eat near bed time.

Emotional state (sleep included) is far more connected to nutrition than any of us like to admit.

3. Leave the iPhone in another room

Smartphones are simultaneously the best ever and worst things to happen to our productivity. Just because you can check email and basically every component of your business as you’re dozing off doesn’t mean you should. Doing so is likely to activate several conditioned responses in the Pavlovian sense. Best case, you’ll start having great ideas to implement tomorrow. Worst case, you’ll start stressing out about whatever bad news your company is wrestling with right now.

Solution: Keep your smartphone’s charger plugged in, in another room. Switch it off.

4Find a way to record last minute “OMG-DO-NOT-FORGET-THIS” thoughts

You’re an entrepreneur, so you’re juggling about 150 ideas of things you should and could be doing to make your business better. Naturally, your unconscious mind is going to throw up “reminders” in the form of bed time epiphanies. And, these will be some of the best ideas you ever have.

The secret is to keep a notebook beside your bed. When you can’t sleep because of good idea overload, just write stuff down until there’s literally nothing on your mind that isn’t on the page. Works for anxiety-inducing ideas too.

5. Wind down before bed 

Transitioning from furious emailing straight to bed is stupid. “Sleep” and “Business” are two very different train tracks and your unconscious mind needs time and space to switch between the two. For the sake of your business’s bottom line, you need to schedule 2 hours or more of work-free relaxation before bed.

Tips for serious players: Start dimming the lights 45 mins before bed. Switch off all electronics at the 30 minute mark. Talk to your family. Read fiction.

6. Make your bed a dedicated sleep/sex temple

Do not desecrate your bed by using your laptop, watching TV or carrying out any other task besides those it was built for. Not even in the morning. If you’re really smart, you won’t even permit reading in bed.

The reasons aren’t even remotely spiritual. When you use your bed exclusively for sleep, you powerfully and deeply condition your mind to anticipate sleep when you find yourself there. In the same way police sirens evoke vague feelings of guilt in your heart, your bed will start to actually induce drowsiness. It’s Pavlov at work again.

If this strategy works too well, you might find yourself falling asleep at the penultimate moment of a hot date. Not to worry – simply utilize any number of other horizontal surfaces in your home and solidify your reputation as a fun loving individual.

7. 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.

It’s not a business expense that the tax man will understand, but a fantastic mattress will pay a productivity dividend that is undeniable. If you need to experience it to believe it, book a night at a Four Seasons – home of the world’s greatest mattress – and prepare to float away on cloud of sweet dreams and comfort. A firestorm of business achievement will follow. Don’t skimp on this stuff.

8. Schedule your day to allow for a bit of morning flexibility 

If you’re suffering from serious insomnia, this is an important one. Many people believe a rigid sleep schedule is important – that you must make yourself get up consistently, bright and early. However, if you’re wrestling with serious insomnia it’s likely that a good portion of the anxiety keeping you awake is centered on the fear that you won’t be well rested enough for that 8am appointment.

So for at least a few weeks, trial this: Avoid commitments earlier than 10 or 11am. Allow yourself a window to sleep in if you need to. Get out of the habit of stressing about having to wake up early, on top of worrying about whatever you’re worrying about. Once your sleep gets better, start setting your alarm earlier.

 9. Allow yourself to think.

Most people with a history of troubled sleep grow to be extremely hard on themselves when they hit the hay. Have you caught yourself groaning and cursing when you lie down and immediately explode with thoughts?

Chances are, you’ve probably lost track of what normal a normal falling asleep experience actually feels like. And you’re probably placing massive, unrealistic expectations on yourself. Duh, you’re an entrepreneur.

That’s why the final tip is to ease up on yourself. If you’ve got a bad track record of sleep, you’re probably getting unnecessarily angry at yourself far too quick. In a terrible spiral, your instant “not-another-shitty-night” realization is probably half the problem.

Instead of beating yourself up about thinking too much, do the opposite: Systematically think through your day, aiming to recall each and every detail.

You may find that you start thinking weird, unusual thoughts – this is because you’re on the edge of dreaming. Go with it – don’t worry that you aren’t getting to sleep – just allow your brain to do it’s thing.

If you entrepreneurial insomnia is crippling your ability to work smart and achieve your goals, you don’t need to put up with it. If you want to take serious action to resolve your sleep issues, in as little as four weeks, consider getting in touch to work with me directly.

Most business owners who struggle with sleep also struggle with productivity/procrastination issues. Don’t underestimate how intertwined these can be! Making a breakthrough with your day-to-day effectiveness is the best way to reduce the stress and anxiety that causes insomnia. I published a detailed video training platform on How to achieve superhuman productivity over at my other company Commit Action. It is 100% to download the entire program – click here to get everything.

What tactics do you use to knock yourself out at night? This list is far from complete, so share your thoughts in the comments…


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  1. Holy wow, this is one of your most brilliant, well-said articles ever. As a professional copywriter, here’s me, standing up and giving you some serious applause. (With cheers, whoops and hollers.)

    I’ve taken my sleep pretty seriously for years – mostly because I have so many issues with it. Teeth-grinding, check. (Big time. BIG time.) Bouts of insomnia, check. Nightmares, check. Crazy days where a bad night’s sleep creates jittery, hyped-up productivity – GREAT for the short term… but in the long-term, it’s detrimental and leaves me exhausted.

    And we both know that I can’t even function before my first cup of jet-fuel java hits my bloodstream.

    The steps you outline here are areas I’ve worked on. I ditched my very good bed in favor of a very expensive and much better bed. I’ve started eating supper earlier, because – yep – a late supper brings on a host of problems. I’ve never used my bedroom for anything other than sleep (*cough* and sex), thank god, but you’re absolutely right… there’s so much more I could be doing to eliminate the sleep issues that crop up constantly.

    I’m printing out this article, talking it over with my spouse and posting it to my fridge as an ever-present motivator.

    Because I love sleeping – and I love the money I make when I sleep great. ‘Nuff said.

    1. Hey James! Feels damn good to know you’re hanging this one up on the fridge 🙂

      I know you’ll never take action on the first item on this list – you need your rocket fuel after all – but you should be able to get good mileage out of the others.

  2. Awesome Post.

    I’ve just finished re-reading The Power of the Subconscious Mind by Dr. Joseph Murphy who talks greatly to the importance of sleep and particularly the thoughts we tell our conscious mind before we enter into sleep where our Subconscious (which creates realities) is very much still talking/awake. He gives great tips/tricks to improve our mind.

    Again great post and I’ve def. suffered this entrepreneurial curse.

    1. Hey Mike, I’m glad you dig this one. This is a great addition to – the internal dialogue before bed is something we should all be paying more attention to. Thanks for contributing!

    2. Great article. I think I can do something with this. The teeth grinding from caffeine withdrawal was a huge ‘eye-opener’ ! I can switch to decaffienated for after the first cup. Also thanks Mike Kawula for that book recommendation. I will read that. If it’s to do with brain power I want to know about it.

  3. Bravo, Peter, and Amen, James!

    You point out the Red-Bull swilling elephant in the room.

    A wise doctor mentor told me once that doctors should never skimp on the quality and comfort of their beds or their shoes (speaking one macho sleep-deprived profession to another).

    And you CAN improve your business success by “sleeping around.” Hotels with signature beds allow a meaningful test drive of each mattress brand. Yes, most of those beds are custom made for the hotel chain … but the chain often sells their bed on their corporate website. When you wake up feeling like a million bucks, it’s priceless. Here are some additions to your excellent plug for Four Seasons, but their are many more…

    Starwood Hotels = Heavenly Beds (Simmons BeautyRest)
    Raddison hotels = Sleep Number Beds in specific rooms
    Marriott hotels = Jamison foam mattress beds
    Carlyle Suites = Tempurpedic

    Sleep tight!

    1. Wow Cory, thanks for weighing in with these fantastic tips! Who knew you were such a mattress expert?! This is terrific. Next time I buy a new mattress, I’m going to do a tour 😀

  4. I think a lot of people try to force themselves into a sleep pattern that is not natural for them. I go to be around three or four and sleep six hours. No alarm clock unless I have an early engagement, and I try to avoid those the best I can. My opinion: if you’re a person who experiences the most energy and the best results during the evening, that is the time you should put into the things that are most important to you.

    The only way I am able to go to sleep without the hassle of thoughts running through my mind is to go to bed totally exhausted. I fall asleep like a five year old kid in the back seat of a car after a fifteen hour day at disneyland. Thats the only thing that works truly and repeatedly for me.

    Paint me nonconformist if you will… please.


    1. Wait so you have to go to disneyland to get a good night’s sleep???

      Getting physical exercise during the day is a big part of this for sure – it helps to quiet the mind if the body needs rest.

      1. That was a simile, but sure, I should definitely get into the exercise thing. Given that so many of the self employed work so many hours, does exercise come up as often as a lack of sleep? As long as I’m driving this sideways, do you recommend or discuss mediation? Just curious.

        1. Generally, if an entrepreneur can’t find time to do exercise because they’re “too busy”, they’re not working as smart as they could be. Exercise is such a powerful force multiplier for a business owner making big decisions, it’s stupid to ignore it.

          Typically, the more casual garden-variety insomniac will not exercise. It’s no coincidence.

          Meditation (I read it as Meditation the first time – haha) is not something I’m an authority on by many means. It may well find itself as a topic here in the blog someday.

  5. Hey Peter,
    Man tip #4, recording the “do not forget this thought”, really hit the spot. I recently wasn’t able to sleep for 2 nights, because I had all these thoughts spinning through my mind. I’m going to start leaving a notebook by my side just in case those nights come again so that I can unload all those ideas. Thanks for the help!

  6. Excercise is a big one. I found when I was on holidays this year I slept badly, I think it was because I wasn’t riding every day as I’m used to.
    That tip about morning sleep is a fabulous one. If you lie awake from 3 as I often do and then drop off to sleep at 530 you spend too much time stressing about not sleeping before you have to wake up at 6 …
    Also I have learnt to embrace my sleep patterns and not get stressed about them. I sleep for 4 – 5 hours and then wake up. So now I just relax, play Solitaire (because it’s more calming (boring!) than reading my novel which can be counter productive! and then switch off. Lo and behold, I sleep.

  7. Great post. Don’t foolishly underestimate the importance of sleep to your health. When you get old and you have sleeping disorders because of years of poor sleep habits, and their accompanying debilitating effects on your mental and physical health, you’d gladly give back all that money you made for better health. Trust me. Think long term and enjoy your life….

  8. Thank you for the tips – very practical ideas that I will be testing out tonight. Especially writing down your thoughts, my mind races around like a trapped fly at night.

    Sleep makes a huge difference, but I found getting up really early after a good nights sleep is extra powerful. I once managed to get into a routine of sleeping from 9pm until 5.30am, the work I got done was immense, things that took all day suddenly took half and hour. The problem is it’s just not practical to keep this routine because at the weekend I like to stay up late.

  9. A tip someone gave me long ago: “You can’t control the time you go to sleep as well as you can control the time you get up. So don’t worry about going to sleep earlier. Set your alarm at whatever time you want to get up and let your go to sleep time iron itself out.” That being said, I do believe some people are day people and others are night people.

  10. I have no problem in falling asleep but I generally wake up for a pee break at about 3.30 and my brain cell lights up and two hours pass before I fall asleep again. I’ve tried all of your remedies before without much success. The only thing I don’t do is exercise much and I’m going to try that. I think that a lack of sleep and exercise contributes to weight gain and poor health

  11. Glad I am not alone in the middle-of-the-night sleep break. I tend to fall asleep at 10 or 1030 every night but consistently wake up between 2 or 3am and have a full blown 2-hour stress fest. Luckily my business tends to be an 11-7 or 12-8 kind of day and I have the luxury of going back to sleep most mornings. I think this drives my new husband a little crazy though and I tend to skip our 6am spin classes and opt for (many times unsuccessfully) a later workout. Exercise absolutely is essential…as are all of my business tasks, and sleep!

    Writing a list in the night of everything I need to do and follow-up on is a life saver. If it’s on paper it’s off the brain.

    1. Hey Christine!

      I recently learned of a great strategy for resolving the middle-of-the-night wake up issue from Tim Ferris. Apparently it’s often the result of blood sugar dropping while we sleep – causing weird things to happen in our nervous system that promote wakefulness. I’m butchering the explanation, but here’s the solution:

      A table spoon of raw honey, made into a warm drink with two tablespoons of apple cider vinegar. The sugars in the honey give our blood what it needs for the night and you sleep like a baby. Try it!

      FYI this isn’t pure witch doctoring… Tim quotes some fairly serious scientific source.

  12. Wow. So on point. I’m 27. Just recently started my own business working from home. I cannot manage to get any sleep. Seriously. It’s not human. My brain will not turn off resulting migraines. Recently was told by the dentist that he can tell I’m grinding my teeth. Well, a few weeks later I broke two back teeth from grinding!! Also my vision has declined. I’m assuming this is also related. The stress of owning and running a business is def not for the weak. I love what I do. I just wish I didn’t out so much pressure on myself.

  13. Awesome job, 10 weapons to battle insomnia (10 being the honey in a warm drink)
    You must sleep well knowing you’ve helped thousands of people sleep well. Good work fella.

  14. My experience is from being a 20 year old entrepreneur experiencing sleep problems related to racing thoughts and high functioning thinking power causing an endless, seemingly unstoppable stream of highly productive thoughts just before I go to bed. Despite how marvellous it is to experience such mental performance, I would much rather it be as soon as I get up in the morning than interrupting my night. For me I’ve noticed conscious stress management and prediction is a vital component of dealing with sleeping issues as too much stress leads to increased cortisol levels and adrenaline which contributes to difficulty sleeping. In reality stress is a difficult thing to eliminate from our daily lives when we don’t fully control it. We can however consciously acknowledge the stress and then our subconscious works on lessening the effect of it.

    For me on occasions writing down my thoughts whilst simultaneously applying meta cognition has been effective however this can take a while depending on the individual as for me I can write forever. I never stop thinking. Here exercise helps massively as can Trauma Release Exercises which when practised reduces your propensity for adversely reacting to stress, therefore aiding sleep. Entrepreneurs can seriously benefit from Yoga – the muscle strength training, resiliency and sense of balance and symbiosis one gets, the techniques applied in practising meditation – controlling thoughts, having greater awareness of thoughts and the technique of acknowledging thoughts and allowing them to freely pass through once resolved.

    For entrepreneurs reaching and maintaining optimal performance is achieved by creating balance in your whole self by listening to your body’s needs thus staying grounded, being in tune with your body and mind by meditating and Yoga and making adjustments proactively. When imbalances occur we get ill. So for sleep by depriving yourself you could, ceteris paribus, set yourself up for high blood pressure, chronic conditions etc. As Peter has said work ‘Smart’ not ‘Hard’, similarly working towards SMART short and long term goals will ensure you live a long and fruitful life. I accept there are costs and benefits sadly to every decision we make in life so it entirely depends on your goals. But remember even with seemingly unrealistic goals, creative problem solving can make them realistic.

  15. This article was spot on. I’m naturally in my head anyway. Starting this business has just exacerbated the situation. I’ve been up since 2am. I will eventually go into a second wave of sleep.

    I’ve done meditation, which helps. I need to get an exercise routine together. Work my body, so my brain has no choice but to rest. I only schedule meetings between 10am-2pm. That’s when I’m at my peak. I will definitely try the warm drink, ACV and honey

  16. I call it twilighting I just but my mind think as you said and go into a dream like thing what do I sleep or not I rest but I call it twilighting

  17. Something that works well for me, and also goes along with point number 4 of this post, is putting together tomorrow’s to-do list the previous night. I lay out all my “Don’t Forget to Do These” thoughts put together a somewhat flexible schedule as well. Helps me sleep MUCH easier.

  18. Brother,I can’t sleep at nights.. Is getting worse. I’m a college student. I also have sinus problem, but I do go to bed at mostly 11. Plzz suggest any method’s to overcome this insomnia.

  19. Hm thats a really interesting point about using the bed for nothing but sleep.

    I practically live in my room/bed. Maybe time to kick this habit.

  20. I’m only fifteen, but already an entrepreneur, I’ve been struggling with sleep as long as I can remember, and I want to thank you so much, you wrote this whole article and I’m assuming you don’t even have issues with this. Thank you so f#cking much.

  21. I have no issue in nodding off yet I by and large wake up for a pee break at about 3.30 and my mind cell illuminates and two hours go before I nod off once more. I’ve attempted the majority of your cures before absent much achievement. The main thing I don’t do is practice much and I’m going to attempt that. I feel that an absence of rest and exercise adds to weight increase and weakness

  22. Thanks, Peter!!

    Here’s my opinion related to managing sleep time and quality:

    1. The quality of your sleep is actually more important than quantity

    Studies have suggested that we actually only need a 1.5-hour REM sleep each day. The thing is, many of us sleep for 7 or 8 hours a day, but most of it is non-REM sleep and don’t actually reach 90 minutes of REM sleep. As a result, they feel tired during the day. There are many tools, wearables, and apps that can help you achieve this, from Apple Watch to apps like Runtastic Sleep Cycle, and so on. These tools will wake you up with an alarm when you sleep the lightest (within your designated time frame, of course), and so even when you only have 4-hours of sleep, you won’t feel tired.

    2. Schedule a full day of rest each week

    Not only for sleeping, but assign at least one day where you totally rest your body and mind each week, no matter how busy you are. Have a full 8-hour sleep for this day, and don’t spend this day partying, drinking, or other non-resting activities. This is where you can totally recharge your energy, and so you can feel energized for the week after.

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