Regaining Control of Your Sleep Life...From a (Recovering) Insomniac Entrepreneur

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Entrepreneurship goes hand-in-hand with a lot of things. Determination. Dreaming big. An embrace of failure and risk. And, in my personal experience: insomnia. 

I’ve found this is especially true for the creators and side hustlers I know. Night is often when you can get uninterrupted work done, especially if you’ve got a day job. Once you’ve been in the groove for a few hours, it’s very hard to turn off. The endless to-do lists. And the rollercoaster of excitement and dejection that go along with running a business make it especially hard for your brain to shut down. I worked long hours as a securities lawyer early in my career, and loved it. But, I never had trouble leaving things at the office…until I started building my own business.  

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All of which is to say: while I’m encouraged to see so many people turning to entrepreneurship and the creator economy over the last few years, I also know first-hand that this is a path that can bring sleep challenges. That’s why I’m interested in sharing my own journey here. I may not be an expert. But I am a creator and entrepreneur who has wrestled with insomnia while scaling our company to hundreds of employees and tens of thousands of users. And though I still have the occasional sleepless night, I can say with certainty my sleep is better than it’s ever been. Here’s how I corrected course (…mostly).

From thriving night owl to struggling and sleep-deprived

I think I’ve always naturally been a night owl. I was someone who thrived on the late nights of college — it wouldn’t be unusual to find me at the library, cracking my textbook at 4:00 am. Even as I was developing my first online LSAT course, it wasn’t that tough to pull long hours after my day job to get work done.

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But as my entrepreneurial ventures transformed into a full-fledged business, my schedule started to shift. I had stuff I had to get up for in the morning, people who needed me to be present and engaged at 6:00 am meetings and early morning flights to catch. Then my kids came along, and that added another layer of responsibility to my morning schedule. Suffice to say, I knew that all-nighters were no longer an option. But by that point, it was extremely challenging to shift my habits and wiring.

I’d lie awake, watching the clock, growing more and more alarmed. By morning, I’d be exhausted and depleted. It wasn’t just uncomfortable to be under-slept. It was impacting my ability to do my job. Countless studies back this up: when we lack sleep, we’re less equipped to process information, use logic, spot errors…or even drive safely.

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Relationships suffer as well. Sleep deprivation makes moderating emotions challenging, and it’s almost impossible to build connections and respond thoughtfully (instead of emotionally). More than once, I had to apologize to the leadership team after a morning where I just wasn’t being myself. It was no way to run a business…or live a life.

Finally taking sleeping seriously

Over the years, I’ve learned both why sleep matters (Why We Sleep by Matthew Walker is a must-read) and how to conquer those nights when it seems unachievable.

My biggest revelation: acceptance comes first.

Sleepless nights are going to happen, and learning to be okay with that is so much more comfortable than fighting it. In the early days of my company, I’d be stressed about money, about product-market fit and about feedback from our customers. My mind would be spinning so much that even if I hopped into bed at 11:00 pm, I’d find myself still wide awake at 2:00 am. 

But eventually, I realized that stressing about drifting off was never going to help me get in the zone. So I started just accepting that it would be a low-sleep night. Hopping out of bed for a walk (yes, even at 3:00 am) or reading a book, and trying again in a few hours. (I tried watching a movie sometimes as well, but that generally made it worse.)

Once I found acceptance, I was able to finally begin taking more active steps to address the root causes of the issue. While books and research helped (I’d also recommend Boundless by Ben Greenfield, or Dave Asprey’s Super Human), I truly have my kids to thank here. Routine plays a powerful role in getting a good night’s sleep — and having kids forced me to abandon my hectic nighttime schedule and institute a regular routine. Over the months and years, the nightly ritual of bath-pajamas-story has helped set my own internal clock to wind down. I even have an alarm that goes off a couple of hours before bed, to remind me to start getting in the zone.

That’s expanded to other critical interventions (though I’m of course not saying this will work for everyone). I’ve got an 8:00 pm cut-off for eating; I avoid caffeine after noon; I’ve cut out alcoholic drinks in the evenings. In the bedroom, I’ve blocked out even the tiniest sources of light to make sure it’s as dark as can be. None of this is really rocket science, nor is it a panacea — but, collectively, these approaches have made a real difference.

This is only the tip of the iceberg. There’s a whole range of more elaborate biohacks out there for those seeking further interventions. For example, though it sounds a little extreme, I’ve found that cold plunges in the evening help relax my whole system. And, they regulate my core body temperature so I’m in the right physical state for drifting off comfortably.

The payoff of putting sleep first

I’ll be honest: it’s rare that I have a day that I do everything just right. But most days, I do most of these things. And when I am tossing and turning, I can at least pinpoint what I did — like drinking a double Americano at 3:00 pm. Having that insight and these tools to reach for when I really need to get serious about clocking some shut-eye has paid off big-time.

For instance, when we were going public as a company. I was staring down a months-long stretch of back-to-back 12-hour days packed with meetings and an investor roadshow. Because I was equipped with the right toolkit to optimize sleep, I was able to get the right amount of rest to come to work ready to go.

In the end, I can honestly say that knowing how to get a good night’s sleep has made me a better entrepreneur. And not just in the sense that I’m more creative or productive: it’s also dramatically improved my relationships with my wife, kids, colleagues, partners, team members, users and investors. With a good foundation of sleep, I’m equipped to grapple with the inevitable (and healthy!) conflicts that arise during the day in the most productive way possible. Passionate debate is one of our core values, so to be able to have the cognitive function, patience and empathy to dig into the issues in a results-oriented way is a huge payoff for me.

For creators and entrepreneurs, I’ll offer one final insight. Getting a better night’s sleep also comes down to cultivating a healthier relationship with your business. Learning how to unplug, how to retain perspective and how to sustain some semblance of work-life balance will better equip you to wind down and turn your whirring brain off at night. While easier said than done, it’s this kind of outlook that sustains you over the long haul. All-nighters and furious sprints might work at first. But a business built to last requires the sustained and focused energy that only a good night’s sleep can bring. 

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