Thomas Lea’s, The 2000 Yard Stare. Image via Wikipedia

There’s an old West Point quote that goes something like: The best laid battle plans are tossed out the window when the first shot gets fired.

Startups are the same. Pretty much every new venture I’ve been involved with has gone through incredibly challenging “near death” experiences.

While we may not be facing real gun fire, the stress levels endured by an entrepreneur when launching a new startup (or any new product initiative) have been found to be similar to soldiers in combat, in terms of sustained duration and debilitating impact on decision making.

We’ve all faced challenging and difficult times when many things are going wrong at the same time. Sometimes you’re hit with an unforeseen dip in traffic or revenues, with real consequences for the hard-working people on your payroll. Perhaps you lose a major business partnership. Or a new competitor starts eating your lunch. Your co-founder starts to go broke. You think: It can’t get any worse.

And then, of course, it does. Your CTO leaves for a new job at Amazon.

Soon, you can’t sleep at night. You lose weight. You act like a jerk to loved ones.

These, my friends, are “the sh*t times.”

What do you do? There are several mitigating strategies for how to get through these challenging situations.

jonspopull21. First, get out of your own way.

Your ability to think clearly and solve problems rationally is drastically reduced by anxiety, nervousness, and/or feelings of helplessness. Cognitive scientists have found that anxious students taking an exam have fewer cognitive resources to apply towards problem-solving when their worries draw on their working memory, the mental space where we manipulate facts and ideas.

I often find that when there is a giant pileup of work problems, there’s a thick layer of “worry” that adds cognitive weight. How do you solve this? I try to “get out of my own way” with the following 3 methods:

a) Learn to recognize and guard against your own negative thought loops. If you find yourself returning to the same negative loop repeatedly (he said/she said, it’ll never work, etc.) break the pattern with this small exercise as soon as the loop begins. Count down by even numbers from 100 to 1 as you count up by odd numbers from 1 to 100, alternating by twos. It sounds a bit corny, but it really does work as you’ll free your mind from “the loops” to think more creatively and constructively. At the very least you will improve your mental agility.  One of the calmest, most even-keeled startup CEOs I work with as an investor, Lisa Maki of pokitdok.com, routinely uses this to guard against wasting mental cycles on negative thoughts. (Sorry Lisa if I outed you on your secret!)

b) Write stuff down. Sounds simple, but writing down all the things I worry about in the form of a to-do list helps. This is obviously not a genius insight, nor does the mere act of writing problems down solve them in any way. But the exercise of quantifying the problems has a pleasantly surprising effect in reducing the day-to-day cognitive burden. It diminishes the layer of worry.

c) Fake it ’til you make it. There’s an old finishing school trick where they instructed young women to smile a lot to put on an appearance of happiness, which was supposed to actually cause happiness. It turns out this actually works. Scientists have found that if you change the external physicality, your internal thought processes will follow. So stand tall if you want to feel more confident.  Smile when you want to be more positive.

Jonathan Sposato

2. Use the ‘M-O-R-E’ approach to eliminate the easiest problem first.

When there are multiple problems at once, it’s easy to feel immobilized. But not all problems are created equal. Business problems tend to have the following four attributes that differentiate themselves from each other, and thus easier to prioritize.

  • They either bleed you money at a faster rate than some others.  (M for money)
  • They reduce your optionality down the road.  You lose choices if you don’t act fast. (O for options)
  • They have highly difficult ‘personnel’ or relationship consequences if you act.  (R for relationship)
  • Lastly, regardless of the issue, some problems are simply much easier to solve than others. You can get them off the table sooner (E for easy)

While your own mileage may vary, I tend to attack my problems in always the same order once I’ve sorted them.

a)  I do all the E’s — the easy things — first.

jonspopullGetting rid of all the easy problems first immediately reduces the complexity of your ‘decision surface.’  It’s like a how a hard drive runs faster after being defragged.  If you reduce your overall cognitive burden, the perspective you have on remaining issues (even thornier ones) gets more focused and decision-making is of higher quality. In most cases, getting rid of all the E’s alone is enough to make me feel much less overwhelmed.  Even if I am left with three more big hairy problems, it is still three compared with seven or eight other things. (Variant of rule #1:  Where you have overlap between E and another letter, E overrides. Conquer that problem first.

b) Next, tackle the O’s.

The O’s tend to be next because losing optionality down the road is effectively the same as losing money or other resources.  A good example of an ‘O’ recently came up when one of my portfolio companies was trying to raise a bridge round.  From a strictly timing perspective, they were in a grey zone of being between their first angel round and their series A scheduled for 9 months later.  They therefore had a choice between simply reopening their previous round, or to consider it a new interim round with a new valuation.  There were numerous technical and financial differences between the two options and the company and its board members struggled at length with the tradeoffs.  But, at the end of the day, one option allowed for much greater optionality down the road.  It allowed the greatest number of current and new investors to participate, and it also set a stronger precedent for the imminent series A. Resolving that problem first as the “higher order bit,” allowed everything else to fall into place (who’s investing, how much, amount raised, process, even which law firm to use.)

3. Eat the elephant one bite at a time.

In our current age, we’ve truly velocitized to instantaneous results. Unfortunately, many thorny problems require a series of incremental changes over time before they reach ideal state. As Lord Chesterfield said: “I recommend to you to take care of the minutes, for the hours will take care of themselves.”

Take one day at a time and maximize every business development opportunity, conversation, chance meeting and idea to the best of your ability, no matter how small. Staying focused on what you can do right now will have the double benefit of moving the problem forward, as well as increasing your own sense of traction.

Remember, this too shall pass with time. More wisdom here from Lisa Maki: Think of all the things in life (marriage, mountain climbing, birth, raising children) that wouldn’t be possible if we just gave up when the going got tough.  Only you can know if it’s time to stop.  If you believe in your vision, see a path you can evolve and have a team that’s excited to show up each day to work on it with you, don’t let anyone else tell you it’s over.

jonspopull34.  Know that EVERYONE goes through the sh*t, especially the greats.

Well, anyone who’s ever done something great, because that entails risk and bravery. Until recently I honestly had no idea Elon Musk had gone through so many personal and financial woes in 2008-2010 before he emerged as the current titan of green energy, green cars, and space travel that he is today.

Just like most everyone, I had assumed successful entrepreneurs always led a charmed life, never breaking a sweat.  But, the reality of it was, that in 2008 he was quickly running out of money across ALL THREE of his core businesses.  He ran into regulatory issues.  His rockets blew up.  Henrik Fisker allegedly stole his car designs.  He was going through a nasty divorce.  And, to top it all off, the worst financial crisis in history hit in 2008, which prohibited him from raising the necessary capital to salvage his companies.

But when the chips are completely down, great entrepreneurs always find ways to pull through.  Musk secured outside contracts one-by-one (NASA for SpaceX, Mercedes for Tesla).  He put in more of his own cash and thus transferred confidence to other investors to do the same.  He made hard choices to right-size his operations to run leaner.  He focused his team on resolving the highest mission critical bugs.  And he even found new love.

So, yeah, even Musk goes thru the sh*t times.  Everyone goes through them.  Even a bonehead like me goes through them every time I do a new startup. So, know this: You’re not alone.

So the next time you find yourself facing impossible challenges: Do everything possible to ‘get out of your own way:’ Prioritize ‘MORE:’ Have patience in knowing that the thorniest problems can take time to resolve; and finally know that pretty much everyone who has done something great has been in the same boat.

Good luck!

Startup Jedi is a regular column by GeekWire Chairman Jonathan Sposato. A Microsoft veteran, he served as CEO of Picnik and Phatbits, both of which were acquired by Google. PreviouslyStartup Jedi: 3 phrases every VC or angel wants to hear during a pitch

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  • http://twitter.com/nparekh00 Nikesh Parekh

    Nice post Jonathan. I think a lot of people forget how hard running and working at a start-up can be when they have some success or see others having incredible success (like FaceBook). Very few start-ups are straight up to the right. Most have lots of ups & downs, until hard work and perseverance find the spark.

  • dollared

    Terrible, terrible choice of picture to accompany this post. Comparing being leader of a startup in today’s America does not compare in any way to the experiences of a soldier in WWII. It is an insult to people who put their lives at risk for us to compare the two, even implicitly.

    • http://www.facebook.com/fitclimb Ali Alami

      This is one of the most best posts I’ve read on GeekWire. I disagree with dollared, before you start
      making assumptions about what’s insulting to veterans you might ask a few. I served 8 years (never experienced
      combat). The values and experience
      gained in service mirrored many of the principles Jonathan mentioned. If it wasn’t for my AF experience, like
      learning to bounce back, having confidence, be resilient, not giving up,
      finding creative solutions, etc… I would’ve quit a long time ago and our
      startup wouldn’t have made it out of the shit.
      Yes it doesn’t compare to real combat but that doesn’t mean you can’t
      use the same principles to get yourself out of the shit and use combat imagery
      to get your point across (what Hollywood does all the time in action movies).

    • http://www.facebook.com/profile.php?id=94500172 Kyle Kesterson

      In a talk I gave about shit hitting the fan, I used an image of an atomic explosion. Would you argue that it too is a terrible choice, given that if you were to dissect the reality of it, it’s absolutely horrific? Or can you agree that it is a strong visual metaphor to drive a point home? Or would you prefer an image of actual feces on fan blades being flung all over the walls?

      Lighten up and contribute to the content of the article.

  • Stanley Shaw

    Illustration credit, please.


    • johnhcook

      That was my mistake. Apologies for not properly captioning. I’ve now done that and hyperlinked the image to the wikipedia page. Thanks again.

  • http://www.facebook.com/vqnguyen2 Viet Q. Nguyen

    Awesome post – and spot on, Jonathan.

    Stanford professor, Robert Sapolsky, has done some great work in the area of stress/anxiety research. Stress hormones like cortisol can shoot through the roof when you’re faced with uncertainty (one of the reasons why artillery shelling is so terrifying). My sense is that the more uncertainties get piled into a decision-making matrix, the faster collective anxieties start spiking. By tackling those easy priorities first and shortening your time horizon for uncertain factors, you reduce that cognitive load and are able to think more clearly.

  • pete

    “You think: It can’t get any worse.

    And then, of course, it does. Your CTO leaves for a new job at Amazon.”

    – Too true; this exact thing happened to us. Jeff Bezos is getting his money’s worth from our former CTO, but we wound up with another strong CTO. If you’re doing something worthwhile, it has momentum that carries you through tough times.

  • bla bla bla

    If all of these Seattle startup veterans put as much effort into their actual companies as they put into writing these aimless and rambling articles, Seattle may had a Google or two already.

    • http://www.facebook.com/profile.php?id=94500172 Kyle Kesterson

      I see 4 things result from a post like this, 3 of which are tied closely together.

      1) “I’ve never heard this before.” GREAT!
      There is a newer entrepreneur who is experiencing or will experience much of what Jonathan laid out, and find more value in reading this, than say, another funding or acquisition story.

      2) “I have heard this before.” GREAT!
      As mentioned directly in the article, it serves to let a struggling entrepreneur know that they aren’t alone, which is extremely powerful in reducing the weight on their shoulders. In fact, I’d like to see more and more entrepreneurs raise their hands and say “hey, me too”, especially those who exhibit more success than failure. The more we can have a discussion around failure and struggle, the better off we’ll all be.

      3) “I’m living it now.” GREAT!
      Similar to the previous, but if you’re experiencing the lowest lows now and can find others with a shared experience and empathy, it gives you a reason to connect, and a possible resource to helping overcome some of your struggles.

      4) “I’m contradicting myself”
      How much time and energy is spent reading articles, getting upset by them, and commenting negatively? If this article positively affects at least one person in a meaningful way, it was a complete success. Besides, many holes can be poked into your logic, but that’s a different response entirely.

  • Jon Poland

    This was helpful. Thank you. I especially liked the tackle the easy problems first suggestion. I always thought that the ‘put the rocks in the glass before you pour in the sand’ trick was hokey.

  • http://kickstand.typepad.com jordanmitchell

    Great post, Jonathan.
    A couple things I used to do to reduce stress in my startup (especially during the 2008 meltdown!) was:
    – Recognize what you can and can’t control, and focus your attention on the former. The latter you can only worry about, which isn’t productive.
    – Expect the sh*t to come. It’s going to happen, so think about it every day and try to figure out when it’s going to happen, what it’ll look like, what to do about it, and how you can potentially avoid it. You’ll be right only some of the time but at least you are more mentally prepared for it, and you might even be ready for it.

  • http://www.facebook.com/mark.jessup.3 Mark Jessup

    I swear this is 100% true: this week has been one of the toughest weeks I’ve had in the last two years with my company. Today, this morning, I was actually starting to think, “Man, is this worth it? It’s like a constant siege with tiny little victories.” (Maybe not that last part verbatim.) Point is, I read that headline, it drew me in, and as much as any advice it gave (which is good, although a lot of the stuff I’ve intuited through experience over the years) the basic tenet of Jonathan’s post was a much needed arm-chuck. I know there’s a certain taboo among entrepreneurs that we should never show anything other than complete conviction and total bravado—but just between us—isn’t it nice to know that the secret, nagging doubt and fears that occasionally pop-up and chase you around the playground at night are part of what everyone goes through?
    Thanks for the post, John. It made a difference::

    • http://www.facebook.com/people/Jonathan-Sposato/786250122 Jonathan Sposato

      mark that is super heartening to hear. in full disclosure as i wrote the piece i felt; ‘there’s probably a lot here most entrepreneurs (most assuredly much smarter than i) have already intuited for themselves, so i hope this adds a modicum of value. but hearing a first hand account of how this was a bit of a positive tipping factor for you mark, in turn made my day : )

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