“Better to ask for forgiveness than permission” is one of the timeless truisms of Silicon Valley. Within the tech-set, this is probably the most well-known piece of advice for the Silicon Valley “way” of doing things. But it is so important that it is worth diving into and exploring for those who haven’t been exposed to this wisdom, as well as emphasizing its importance for those who understand it in theory but haven’t yet developed the strength to apply it.
Before we dive in, let’s also point out Mark Zuckerberg’s famous startup philosophy because it is really a restatement of the same point, “move fast and break things.” Many other chapters talk about specific ways to remove time-wasting activities (thus being the converse way to go about moving faster) and “break things” is really another way of saying you can ask for forgiveness. You ask forgiveness only after you break something.
The reason why this isn’t conventional wisdom, outside of Silicon Valley, is that people by human nature tend to not like to break things. Additionally, most work incentives are structured so that the punishment of breaking things is greater than the reward of what you get (even just emotionally) if things go well.
The arguments on the other side are compelling to all with a Silicon Valley worldview (and a Silicon Valley incentive structure.) What it boils down to, in short, is: to get anything done, you will have to step on toes. And by “anything,” I literally mean “anything” (well “anything non-trivial”) And “stepping on toes” is just the euphemism for breaking things—it’s the smallest thing you can break.
On the smallest scale: you want to write something? You’ll break the editorial standard because you didn’t use the same punctuation style as per the style guide (maybe you’re British and put periods and full stops outside the quote, not inside.)
On a larger scale: you will push through and pressure others to go along with initiatives that some other people just don’t want to happen.
No matter how big or small, toes will get stepped and things will get broken. You have to accept that as the reality of trying to make things happen.
And the reason why the non-Silicon Valley world doesn’t follow this philosophy is that in most industries, “making stuff happen” is of secondary importance behind “preserving the status quo.” And that’s even too common in Silicon Valley as well.
If you’re going to adopt this philosophy, there are a few ways to make it a bit easier to do.
One is to warn people that you may break things: both in general, and then at each specific point or turn. Things that are broken, when the breakage is expected, is better than when it’s broken by surprise. And you can even paint it, preemptively, as a positive, “Hey, I’m working on X, Y, Z, and I know there’s a risk that Q or R can go wrong, so I’m working on minimizing that.”
Do you see what I did in that wording? I implemented the guidance from the other chapter about articulating risk factors, but more than that: I not only warned the other them that something may break, but I articulated what may break (Q and R) and reaffirmed to them that I’m on top of it.
And that minor phrasing actually turns out to be an important point. Breaking is bad, but approach it as part of your job, so you have to just let everyone know what is likely to break, be as prepared as you can be, and be on top of the communication around it.
Breaking things, in other words, is the symbol of having responsibility. If you want to grow, you need to take on responsibility. If you take on responsibility, you need to accept the fact that breaking things isn’t an “if” but a “when,” “what,” and “how.” And the “who” is easy to answer: you, should you choose to take on the responsibility yourself.
