I get asked this question quite a bit and frankly it’s a pretty standard question to ask a startup CEO. People ask it, I suppose, as a way to peer into the CEO brain. As part of my CEO advising work I’ve periodically asked a similar question which goes like this: “So, what issue caused you to wake-up at 3 in the morning with a sweaty forehead this week?”. Generally speaking, here’s how I answer the “what keeps you up at night?” question these days.
First off, the biggest culprit for keeping me up at night is everything. Given the nature of the job, with so many moving parts needing to be juggled simultaneously, the startup CEO brain whirls at full speed 24 hours a day, 7 days a week, 365 days a year. You constantly think about some aspect of the company and it’s usually some area that isn’t working as perfectly as you’d like it to. There’s a useful metaphor— and every startup CEO knows it — that your company is like a chain and you’re only as good as your weakest link (or links). The problem is you constantly think your company is nothing but weak links when, in reality, it’s loaded with many strong links. It’s just that the startup CEO mindset goes so easily to the dark side:
Your business planning process is in shambles — it feels light years from becoming the finely tuned operation you want it to be for your team;
One of your board members made an introduction that you haven’t followed up on (damn it!), or they have tossed out an idea that doesn’t exactly fit into your near term roadmap so you’re trying to figure out how to most eloquently tell them that (double damn it!);
Someone on your executive team is trying to work through some “people challenges” within their own team and they’re looking for guidance from you;
One of your sales team members just relayed news that a competitor is talking trash about your company and that this competitor continues to misrepresent to potential customers what your product or service actually does;
Oh s#&t, our office move needs to take place in three weeks;
Your head of engineering keeps telling you the company’s not investing enough in infrastructure, web services architecture, security, getting rid of all your “tech debt”, or some other critical part of your platform. Oh, by the way, she/he tells you none of these investments will directly increase your revenue or profits, but emphatically warns that if you don’t greenlight these investments you’re simply signing the company up for a cliff dive down the road.
Yep, the list goes on and on. None of these items on their own is insurmountable, and over time you get better and better at prioritizing across never ending laundry lists of priorities like these. However, thanks to the special wiring of the human brain this “to do” list scrolls endlessly through your mind like credits at the end of movie. For better or worse, the CEO brain fixates on all the real (or perceived) weak links in your company’s chain, and there’s always what feels like a dozen or more that need to be fixed, improved, or “figured out” as a result. Clearly, a full night’s sleep falls to the bottom of your to do list every evening.
The second reason startup CEOs live sleep deprived is because they fear the “fatal flaw” that constantly lurks around the corner, waiting to deal a death blow to the company. My definition of “entrepreneur” is anyone who leads an effort to build an organization that isn’t guaranteed to succeed. More specifically, entrepreneurs — and notably startup CEOs — lead companies whose probability of success is quite low. And when you layer on top of these long odds the responsibility the leader feels on behalf of their team, family, and investors, it’s no wonder CEOs barely get any shut eye. They can’t help but continually tick through the dire list of ways that their company might be impaled. Just about every night one of these horrible events bubbles to the front of your prefrontal cortex, literally sending you into a downward spiral imagining how this one issue might bring the whole company crashing down. Your subconscious brain loves to convince you in the middle of the night that there’s no way you’ll hit your revenue goal, your user engagement goal, or any of the most critical goals necessary to raise your next round of capital.
A final culprit of CEO insomnia stems from the all-consuming nature of the job and the related guilt that ensues when you realize how poorly you treat your significant other and how unlikely it will be that you win this year’s “Parent of the Year” award. For sure, nobody misses more of their kids’ school events, cancels more date nights with their partner, does less work around the house, or checks-in less frequently with family and friends than a CEO in the throes of trying to scale a startup company. Yep, you pretty much feel like a loser on the friends and family circuit.
So let’s recap. What keeps a startup CEO awake at night? That’s (1) everything, (2) the never ending fear of the fatal flaw that might kill your company, and (3) massive guilt for being a lame partner, mom, dad, son, daughter, brother, sister, uncle, aunt, or friend. Great, now that you know why you can’t sleep, what are some potential remedies?
Quit being a CEO. Okay, not a realistic option I know, but I had to throw it out there because it just might help you get more sleep.
Melatonin. I wouldn’t recommend going beyond this organic option to other sleep aids like sleeping pills, but adding something natural to your evening ritual that your body already produces might be helpful.
Breathe and write down what is going on with your business. When you do this you’ll realize that (a) you have way fewer weak links than your reptilian brain is trying to convince you of and (b) nothing going on right now in your business will kill you tomorrow, which means you and your team can devise a plan of attack for the road ahead. I encourage CEOs to create a framework that allows them to manually draw or list all the moving parts in their business so they can easily identify high order bits and heighten their focus in that direction. Remember, in the scheme of what’s ahead for your company, today is literally ground zero or day one.
Eat healthy, move, and meditate. If you want more naturally produced serotonin flowing through your body, eating well to support its production in your gut while moving and meditating to help it flourish in your brain represent important time investments for a CEO to carve out.
Build a great team and give them the ownership and latitude they need to to remove bottlenecks and weak links. They may get a little less sleep as a result, but the only way to scale your business is to most efficiently map strengths, skills, and knowledge to where they should be applied. Ultimately, by doing this well you’ll all actually get the sleep you need.
Make time for family and for you. One of the strategies I used (and still do out of habit today) when my daughters were young was to get up early on weekends to get stuff done at a local cafe so that I got home when they were waking up. This allowed me to spend full Saturdays and Sundays with my kids. Also, schedule diligently your date nights with your partner and be sure to make it to your kids’ school events and games. Finally, figure out something that recharges you personally — running, writing, kayaking, painting, playing guitar, ballroom dancing, watching college football and drinking beer, whatever! — and make sure that activity gets on your schedule each week. [One side note on the guilt that comes with missing time with your kids. Know that if you’re doing this job while they’re in elementary school and beyond they’re actually benefitting from observing you as a role model. They get to see how important it is to be committed to something one’s passionate about, how to work with people to achieve something great, and how to stick your neck out there and take a leap when there really is no safety net waiting below.]
Finally, determine what you can control — and what you can’t control — and remind yourself that there’s only so much you can control. Figure out what matters most (your plan, product, people, partners, promo, P&L, or powder e.g. raising money) at any given time and do your best staying focused on those links in the chain. Support and empower your team to utilize their talents so you collectively build the business you all envision, and so you all get the sleep you need to stay productive, positive, and healthy.
Originally published on Medium on February 9, 2018. This Substack version is maintained as the canonical archive.