The Perils of Positivity

I often hear that startup founders need to have a kind of unreasonable positivity in order to succeed. The belief that this impossible thing will work carries you through the pain and obstacles to finally achieve success, or something like that.

I think this is total fucking bullshit.

I mean, yes – you need to believe the thing will work. There are going to be ridiculous obstacles in your way, and the most likely outcome is failure. But so often, I see people espousing this, “I have to be confident it’ll all work out!” and there’s two ways I see that play out, one alright, one terrible:

Way 1: I look at the thing we’re trying to do and with clear eyes, dive into the potential problems. I may not have all the answers, but I dive deeply enough that I can understand the relative risks involved, and make a clear assessment of whether we’re likely to be able to overcome those obstacles, tackle them in risk priority order, and make things work. It looks daunting, but I understand it as well as I can, and believe we can get through it, even if it’s not clear exactly how yet.

Way 1 isn’t terrible, and if you’re in a startup, it’s what you have to do. But a shocking number of people interpret this call to positivity in a different way.

Way 2: I look at the end goal of the thing I want to achieve and visualize that we’ll get there. I don’t really need to think about the obstacles in the way, because I know we’ll be able to achieve the end result. Over the course of development so far, we’ve run into a bunch of problems, but they’ve always worked themselves out, and so I know that if we just keep at it, we’ll get to the end goal. I just need to stay positive.

Which, when I write it like that, sounds really stupid. But a surprising number of people in positions of power over the course of my career have mistaken “positivity” for “lack of diligence and awareness”.

And that goes for at least two things. First, they’re not diligent about actually understanding the obstacles, in number or scope, in front of them. Second, they don’t understand how those obstacles were actually dealt with during development – who struggled with them, who overcame them, how, or at what cost. So they also don’t understand what it’s taken so far to get to where they are.

When you have a problem with a startup, someone fixes the problem. It may not be you – hell, often it’s better if it’s not you – but nothing ever, ever, ever “resolves on its own”. And holy shit, the number of times I’ve heard these positive people say “It just works out,” or “The problem just goes away,” makes me want to stab a lot of folks. Nothing “just works out”. Nothing “just goes away”. Someone makes it happen. Someone dives into the complex problem, builds understanding, attacks the weaknesses, and figures it out. What you’re saying when you say the problem “just works out,” is really “I have no idea how it worked out, who put in the work to make it happen, but I don’t really care to give people the credit they deserve.”

And yeah – I’ve often been in the situation where I’m solving critical, urgent, difficult problems and then had someone above me say, “Yeah, these problems just work themselves out! Amazing!”

“Positivity” isn’t something you inject into the process. Positivity is a symptom of trust, understanding, and hard work. Running into a room full of bears with your hands over your eyes yelling, “I believe it’ll all just work out!” is a surefire recipe for being eaten by bears. And that’s the correct god damned outcome for you if that’s your approach.

You want positivity, look at your problems. Assume that no problem will ever solve itself. Figure out who is doing the work to solve the problems, figure out who should be working on them if no one is already. Give them the time and resources they need to take a solid stab at figuring it out, and the credit the ever-loving shit out of them if they make it happen.

As a leader, some folks think that “the buck stops with me,” means “I can take all the credit for everything,” because I’m ultimately responsible. And sure, to some degree that’s technically true. But it’s a really counterproductive, ego-centric, and … well, childish approach to things. A good leader takes no credit. They give away all the accolades for success. They take all the blame for failures. Because leaders get too much by default. People remember Steve Jobs, but Steve Jobs didn’t resuscitate Apple or invent the iPhone on his own. Leaders get too much credit. It’s their job to give as much of that credit away to the people on their team who made things happen.

But that starts with being aware of who’s making things happen. So if you think positivity is that problems just go away on their own, you’re failing as a leader and you’re failing at your job.

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