Raise Your Head Before You’re Dead

We waste years because we cannot waste hours.” – Shane Parrish


Every founder of every startup that ever got anywhere is first and foremost a doer. This is because step number one is to get things off the ground, by yourself.


Doers are pretty bad at not doing and just observing from afar. Seeing and analyzing the forest instead of one single tree. Zooming out.


My co-founder and I spent two years in crazy doing-mode: selling, building, hiring, and raising. We did it well, except that we never zoomed out quite far enough to observe that we were solving the wrong problem.


Only Missing What Matters


It is very possible to make positive progress every single day and still drive your company off a cliff. Product-market fit, culture, momentum, financials, team alignment, and motivation can all seem perfectly fine from a day-to-day lens and bad when you pull your head up and see that cliff.


Let’s talk about 3 of these.


Product-market fit. A good team can build a product, sell it, satisfy customers, and never reach product-market fit. Only by zooming out can you see the real trends: Pulling teeth for every sale? Customizing the entire product for every customer? Users only kind of like you? We were there for 2 years.


Momentum. Making some progress every day is good. Or is it really? It’s necessary to take a step back to understand whether your progress is meaningful. Is it fast enough or is it too slow? Is it accelerating or decelerating? Is it accelerating at a high enough rate? Even a slow walk appears fast when you’re staring at your feet.


Team Alignment. It is incredible how people can work together, on the same things, every day, and still diverge in different directions. Only by zooming other people out can you understand where they are actually headed, be shocked, and recalibrate.


How can we see these trends earlier and more clearly?


Zooming Out


Cameras zoom out instantly, for humans it’s a little harder but still a learnable skill.


The first step is to become a slacker: Going on a random walk? Just sitting there doing nothing? Can I really ignore that fire over there? Yes, yes, and yes.


You must become comfortable with “wasting time.” Doing nothing but pondering and reflecting.


Then more tactically:

  • Trust your people. To get away from the weeds you need to trust your people to handle the weeds and bring important things up to the surface. Let go a bit and see what happens

  • Take walks. Walks, especially in nature, get your mind to drift just the right amount to see more of the larger picture. I like to combine them with writing as walks surface vague things and writing crystallizes them. If you don’t like walks, I still recommend having some dedicated physical space and time for just thinking without doing

  • Planning/offsite Meetings. Teams who think that they don’t need an offsite always need one urgently. Start at the highest level and don’t get tactical too fast. Spend time on reflection, challenges, dreams, and big picture stuff primarily

  • Boards and fundraising. I used to dislike boards and hated fundraising. Now I cherish them as an opportunity to get the perspective of very smart people who look at a ton of companies and only care about the big picture

  • Talk. Speak to friends, your family, and other founders. They don’t care about the nitty-gritty and will naturally pull you out of the weeds. My wife always sees the most important trends in my startup way before I do

This is quite personal so experiment to find what works for you.


Zoom Out ASAP


Signs that you should zoom out right away:

  • Falling behind your goals. Goals tell you how you’re doing. When you start falling behind, do not explain it away. Take a deep breath, zoom out, and get a clear view of where you are. Data, in general, is a useful high-level health monitor

  • Unhappiness. When two or more people around you are becoming demotivated, it’s often a sign of some negative trend that you’re not seeing yet

  • Complacency. There is no business-as-usual in startups. If it starts feeling that way then you’ve got a problem coming around the corner

  • Questions. Ask these questions frequently: What is our top priority? How are we doing right now? What is our biggest challenge? What are you seeing that I’m not seeing? If the questions surprise you or feel off then it’s time to zoom out

  • Gut. Our gut often knows things before our conscious mind does. When something doesn’t sit right with you, take a minute, and listen attentively to what it has to say



Raise your head, zoom out, and drive your company to its destination.