Saturday, March 14, 2015

Waking Up In the Middle of the Night - Stress Relief for Entrepreneurs: Watch Star Trek and do Yoga

Recently, I was having lunch with an entrepreneur friend, who was back in Silicon Valley from Russia, and we were discussing the recently released Russian edition of my book, Zen Entrepreneurship, which he had seen with its Russian title,  Biznes v poze lotosa, which  translates roughly to “business in the lotus position”.
At some point in the conversation, he asked me what techniques – meditation, Yoga or otherwise I might recommend for him, because he found himself “waking up in the middle of the night” worrying about his business.  His business issues were even making their way into his dreams, he said.  Was there some way to prevent this?
My first reaction was of recognition. This has happened to me often, and I’ve heard many other entrepreneurs say the same thing over the years. it occurred to me that this must be very common for most business owners — whether you’re self employed, running a small business, or running a startup that has raised millions of dollars.
It is very hard to “disconnect” from the business, particularly during stressful times. In fact, it might be more surprising if you are running a startup and not worrying about the startup in the middle of the night. This article is about some of the causes and ways to deal with entrepreneurial stress, from both western and eastern perspectives.

The really hard thing about startups

I’ve often said that startups are hard, but this doesn’t mean that they are hard work. The thing that makes startups hard is not the amount of hours you have to put in — it’s that you really can’t avoid “taking your work” home with you.
This seems to be true whether your startup is suffering from not having enough money (like many bootstrapped startups) or if you’ve raised millions of dollars in VC or angel funds. In the case of CEOs who have investors, there’s nothing like the sobering realization that they put all that money into you with a certain set of expectations, and those expectations are not being met (since most startups have over optimistic business plans, most startups don’t make their initial numbers).
Even startups that succeed will often flail around for a while before they hit their second (or third) wind. It’s during times like these that stress that’s been building up little by little can suddenly start to feel like an un-liftable weight on your shoulders.
This is compounded by what I call the “self-confidence problem”. Entrepreneurs tend to be people who believe in their own capabilities — and that might have been true in school, where how much they learned was usually a function of how many hours they put in, or even in their previous job, where they were evaluated for a promotion based on their own contributions in relation to other employees.
If something requires hard work, figures the would-be entrepreneur, I can handle that. This usually leads to the belief that working harder can make you more successful. That might be true generally, but when it comes to startups in particular, while putting in long hours is usually necessary, it’s also not sufficient for success. The thing that can be frustrating for so many entrepreneurs is that, sometimes whether a startup succeeds or not is not always under their direct control.
There are plenty of startups where the founders work their tails off, but that don’t make it. There are a million things that can go wrong — you could hit the market too early (or too late), funding which was easy to come by in a boom market suddenly dries up and you find your ship aground prematurely. On the flip side, I’ve seen successful entrepreneurs who had great successful exits because the market was hot, but whose companies would have otherwise failed as stand-alone entities had they come even a year earlier or a year later.

Why Startups are Harder than MIT: What Could Go Wrong

To solidify this point, I’d say that I worked much harder in terms of number of hours spent when I was a student at MIT than I did at most of my startups. Pulling all nighters, usually because a problems set was due the next morning, or cramming for exams, was common-place. The thing is, even though I was working hard, I don’t think I was ever as stressed out at MIT as I have been in my various startups. OK, I might not always have gotten straight A’s, but I knew that as long as I put in the time, I could get a decent grade.
In a startup, rarely is the result a simple matter of how hard you work (or surprisingly, how much money you spend). Things always have a way of going differently than you expect. If you are the founder/CEO this usually means you’re waking up int he middle of the night worried about some thing or another that either has gone wrong, or could go wrong
What could go wrong? Plenty.
Your first major customer cancels an order. The round of funding you were counting on doesn’t come through. Apple (or Facebook or Google) kicks you out of the app store, which was responsible for 100% of your sales. A co-founder has already vested their stock and suddenly quits. A recently hired, much anticipated, star hire isn’t what you expected, or maybe a long-time super-valuable employee decides to leave for a competitor. You miss your projections, not by a little bit, but by more than a million dollars! Or maybe, a recently-fired employee sneaks into your office and steals your laptop, a fact you only know because the police came in and got the surveillance footage from your landlord, and you have to decide whether to press charges.
Yes all of those things have happened. And that’s just in startups that I have personally been involved with. I’m sure there’s a whole world of startups out there with problems that I’ve never encountered.
Whew! No wonder it’s hard not to be stressed out as an entrepreneur.

Brad Feld’s First Rule: You aren’t alone.

I was recently interviewing well known entrepreneur-turned VC Brad Feld for my upcoming book, Startup Myths, and I asked him what advice he’d have for entrepreneurs going through stressful times.  His first piece of advice was to remember that you are not alone.  Many, many people are going through the same thing with their startups, though they are not out talking about it.
Brad was one of the first in the startup/VC community to talk about depression and the role it’s played in his career.  I’ve seen that many entrepreneurs may find themselves sliding into “mini-depressions” when they’re trudging along and come across intractable problems that they just can’t or don’t want to deal with anymore. (if you haven’t read his blog, it’s at and worth a read).
Remembering you are not alone is a great first step.

This reminded me that when I was doing my very first startup in Cambridge, MA, we had a local group of CEOs of local startups that met every so often — I think it was once a month or so. I used to joke that this was “my CEO therapy” group.
The thing was, being able to talk about the things that were going wrong with a group of people who understand and are going through similar things can be therapeutic in and of itself.
I have to admit, sometimes I would come away feeling much better about my current crisis because someone in the group inevitably would be going through something much worse. For example, I remember once I worried about only have runway for a few months of salary left, when I realized that one of the other members of the group didn’t have enough money to make payroll this month!
This wasn’t some startup version of schadenfreude– rather it was the first step to putting things in perspective, which can lead to taking your own problems in stride and realizing that rarely is it “the end of the world”, even if it seems like it right now.
If you don’t have a support group like this, informally or formally, it might be worth looking into joining or creating one. I’m on my fifth startup, and you’d think by now I wouldn’t need other entrepreneurs who are going through similar things to commiserate with. You’d be wrong.
Can’t you just talk to you co founders, investors, or advisors?
Yes and no. I’ve found that even though investors, advisors, and co-founders can be sympathetic, they often don’t understand the stress that a founder/CEO is going through at the moment. Sometimes the thing that you really need to vent or complain about, the thing that’s causing you all this stress, is your investors, your advisor, or even your co-founder!

Western perspectives and Physiological effects of Stress

When I started to think about techniques that could help my Russian friend, I realized that we all have very different ways of getting and dealing with stress. Exercise, everyone will tell you, almost always helps with stress. I agree, but by itself it may not be enough.
There’s a good explanation of the western chemical viewpoint of momentary, flight or fight stress vs. the kind of chronic stress that entrepreneurs live with, in another article I read recently by entrepreneur Hana Abaza (
Since the human body is designed to deal with a stressful situation like a saber-tooth tiger, the chemicals that the body secretes during stressful times are meant to last as long as the “flight or fight” response lasts. Either you get away and survive or you stay and fight the tiger.
Abaza stresses that being in charge of a startup is more like “chronic” stress, and the physiological issues that it can cause. Coincidentally, she also talks about waking up in the middle of the night during her own startup experience 3 or 4 times a week.

A Yogic View of Stress

Being a mystical as well as practical kind of guy, I believe it’s worth looking beyond just the chemicals to see how we get stressed out and what happens in our mind, body and our energy fields.
It’s pretty easy to see that each person is different and holds their stress differently, resulting in different physiological symptoms. Two people going through the same situation have a very different reaction to how “stressed out” they are.
As an example, I mentioned that I wasn’t really that stressed out at MIT as a student, but some other students took it very differently. Suddenly, not being the smartest person in the room hit at the very core of the valedictorian personality they’d built up over their entire lives up to that point — and this caused more than its fair share of angst, depression and worse.
Wilhelm Reich, who along with Carl Jung was one of Freud’s most esteemed disciples, believed that we hold accumulated stress in the fascia — the connective tissues in between our muscles and our bones. He came up with a therapy that involved learning to breathe as a way to “release” this accumulated stress, which had dramatic physiological results in many of his patients, and many consider him the the grandfather of body-oriented psychotherapy.
Surprisingly, this view coincides very well with the Yogic/Eastern view. From a Yogic point of view, this has to do with our individual personalities, our habitual thought-forms, our karmic tendencies. As we build up stress, we create and hold onto little deformations into our energy fields, called samskaras, which accumulate around our body in previously transparent sheaths called khosas.
Finding ways to relieve that psychological/energetic holding not only reduces stress, it lets go of some of the karmic traces we’ve accumulated, clearing up our energy field and our ability to see the situation clearly. I like to use the analogy of a muddy windshield — it blocks your view of what’s really happening. The clearer it gets, the more easily you can see what’s happening around you, and your role in it, and sometimes that’s enough to give us the perspective to get un-stressed.
In the Buddhist point of view, the ability to let go of all that is locked up in our minds (and by extension our bodies) is what eventually leads to enlightenment.
These samskaras are caused by our “grasping” and “aversion” — reactions we have to the situations we find ourselves in. As we hold these thoughts in both our mind and bodies, we have muddied up our system, leading to a lack of sleep and even dreaming about our problems. One reason we use the term “sleep like a baby”, is that babies haven’t accumulated enough “stress” or “samskaras” to disturb their sleep (at least in this lifetime).
In Tibetan Buddhist traditions, there are two kinds of karma: the “big karma” which might involve bad deeds like killing someone or cheating someone, and “little karma”, which are things that have made their way into our minds which we have a had a strong reaction to — exactly what causes the samskaras in Yogic traditions.
To resolve the “big karma” might require lifetimes of work. However, it’s the little “karmic traces” make their way into our dreams, particularly the ones that seem to be regurgitating things we had been worried about all day. So how do you release some of these karmic traces and reduce some of the stress?

Some Tips and Techniques From My Own Experience

My own personal mantra when I am stressed out in a startup is “Watch Star Trek, Walk by the Bay, and Do Yoga”.  These aren’t meant to be actual techniques (you might hate Star Trek, not live near the Bay, and find Yoga to be ridiculous), but rather three different ways that I approach dealing with stress.
  •        Taking walks in Nature.  There’s a little park in Mountain View, just down the road from my office, and only yards away from Google, that always helps me to deal with stressful situations.  It’s called Shoreline and there are paths that are near the San Francisco Bay, and when I’m walking I can see the mountains to the west (green, tree covered), the water of the bay, and the mountains to the east (which look more like the desert).  There is also a nice breeze coming in from the bay (OK it’s not always nice- sometimes it stinks lol).   The thing is, there’s something about gazing at mountains and feeling a breeze going through your body and energy field that has the effect of “loosening up” the things that you are holding – mentally, emotionally, and in your body.  What I’ve noticed is that even if I’m holding a lot of stuff in at the beginning of the walk, by the end my body is more relaxed and I’ve let go of some of the things that are bothering me.  You can find a place like this in your neighborhood.
  •       Watching Star Trek.  This usually gets a laugh when I tell people about it.  The truth is, that  I find we all have certain types of fiction that not only “take us away” from where we are, but somehow feed our soul.  For me it’s usually certain kinds of science fiction or fantasy.  For you it may be Sex and the City or Reality TV!  Well maybe not Reality TV, but you get the general idea.  Find something that you can watch that “feeds your soul”.   For me, watching Star Trek brings back memories of childhood and anticipation of great things in the future, and somehow links to something deep in my soul – maybe because I’m an explorer at heart.  Whatever it is, take an hour every day to watch an episode of a TV show that does it for you or read something that takes you into this kind of feeling. 
  •       Doing Yoga.  I’ve already mentioned Yoga. In fact, the original point of Yoga was to start to dissolve some of the samskaras that we are holding. Too often, in the west, Yoga and exercise are considered the same thing.  I had one Yoga teacher tell me that I'd probably be sore the next day.   She was right. I was not only sore the whole next day, which might work for some people, but didn’t work for me- that's not the kind of Yoga that helps me to release stress.  The key is to find Yoga which an allow you to do stretching and to release, a kind of meditation for the body which allows you to gently release the samskaras building up in your body and mind and energy field.  You’re not training to be a boxer or a weightlifter or a football player!  If your Yoga isn’t doing it for you, I’d be happy to recommend some DVDs or books that have the kind of Yoga.
  •       Meditation.  There are many studies showing that regular meditation has health benefits and leads to stress relief.  There are many different techniques of meditation, but at the heart you are trying to calm the mind and the tumultuous thoughts that we are all caught in the middle of. I think of us as one of those snow-globes that has been shaken up, thoughts are flying every which way and it’s difficult to see. A short meditation can do wonders for letting the snow settle down and get a clear view of what's happening. 
  •       Use Your Work As Meditation.  Being mindful at work can have wonders for not only your concentration but on your level of stress. Rather than worrying about “making payroll next month” (which may be a real problem that you have to deal with), when you are writing some code or doing a spreadsheet or having a meeting, focus your mind and attention on the task at hand.  I call this “using your work as meditation”.   Your mind will inevitably wander.  You bring it back. This is just like meditating but it is more about keeping your mind on what you are doing.  If you do this right, you won’t be thinking about the million things that “could go wrong” if your startup runs out of money next month.  You’ll be thinking about whatever task you are focused on. 
  •        Breathing exercises.  There are many breathing exercises that can help you to release that which we are holding – i.e. that which is causing us stress.  If you are finding yourself unable to sleep, doing a slow breathing exercise is a great way to get back to sleep – almost any rhythmical breathing exercise can work.  Here’s a simple one I learned recently:  breath in fully (even to places that you don’t normally breath into) expanding your lungs as much as you can, then breathe out fully, much longer than you normally would.  Repeat 10 times.  After 10 times, hold your breath for 20 seconds.  Then start the 10 breath cycle again. If you’re like me, somewhere in the 10 breaths, you’ll lose count of which breath you are on and end up asleep.  There are of course many different types of breathing exercises – breath of fire (not recommended for falling asleep), alternate nostril breathing, etc.
  •      Get a Massage.  Since stress is being held in the body, it's amazing how great you can feel after having some body work done.  This doesn't make your stress go away, but it does let you realize that there's something beyond the stress, so that when you start to feel it again, it ends up being a little less "all-encompassing".   

From an eastern point of view, stress isn’t purely a chemical thing, it is the result of our thoughts, emotions, and new “reactions” adding onto the accumulation of samskaras we have in the past (our “karmic traces”).   
Sometimes I like to think of being an entrepreneur as karma+  plan - i.e. we are accelerating our reactions and building up karmic traces with every stressful situation and our reactions to it, which is why we so often end up dreaming about our business problems.  This is why I believe entrepreneurs need techniques like Yoga and meditation even more than most people, because the stress that builds up  can make our lives hell and being off your game can have much more immediate consequences for an entrepreneur who's running a startup.
So, the next time you find yourself stressed out, take a deep breath. Remember you are not alone, and there are other startup CEOs going through what you’re going through. Then, do your own version of my personal mantra: Take a walk by the bay, watch Star Trek, or do Yoga!

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