Beg for forgiveness

There are two general approaches to doing things:

  1. Ask permission
  2. Beg for forgiveness

I’m here to tell you to do go with #2!

Asking for permission

Seems like a good idea, yea? The ol’ “why don’t we just check with legal,” or “let me make sure this wouldn’t upset anybody.” The problem with this route is if you look long enough, you will eventually find somebody who opposes the idea.

If the founders of Warby Parker, Uber, Airbnb, or any number of startups asked for permission, those businesses wouldn’t exist. Instead, they went for it, opting instead to beg for forgiveness. And thank goodness they did!

Begging for forgiveness

Instead of asking for permission, I say just go for it. Particularly when it comes to things that are clearly the Right Thing to Do. Want to email your users to ask what they think of your app but not sure if your Terms of Service allow it? Do it! Want to start a business and not sure the regulations? Give it a go!

A litmus test I like to use is, in the 0.001% case that someone did sue you or the police knocked on your door, would you feel comfortable justifying what you did? In most cases, if you’re doing the right thing, you’ll never need to beg for forgiveness anyway.

Example 1: Camp PALS

As a personal example, during my senior year of high school a few friends and I decided to start a summer camp. We were teenagers at the time and knew nothing about camp regulations. Had we went around asking for permission, the camp would probably not exist. Instead, we just went with it. We figured:

  1. Are we adding value to the universe? Yes.
  2. Are we going to get in trouble for this? Probably not.
  3. If we did, would we feel comfortable justifying our actions? Totally.

Good thing we did! 10+ years later and PALS is now a proper nonprofit operating dozens of camps & programs each year.

Example 2:

As another example, a friend and I started a drink delivery service during our senior year of college. Students could fill boxes of 20 drinks on our website and we’d deliver it to their door. We called it

Had we sought a food distribution license or asked UPenn if we could use their mark, we would never have gotten the business off the ground. Instead, we opted to go for it, operating the business out of our living room and double parking our saab wherever we could find a spot. We ended up selling 20,000+ drinks that school year and licensing the site to other schools. (I can share some interesting stats on what college students like to drink if anyone is curious!)

Incidentally, several years after graduating I got an email from Penn’s trademark enforcement people asking us to not use the name “Penn” and a variation on the school’s crest in our logo. We were happy to beg for forgiveness and oblige with the request at that point, as the business had shut down by that point :).

Okay, not always

Sometimes there are reasons to ask for permission — like in cases where someone could halt your progress later, e.g. an executive who needs to sign off on a launch. In those cases, get permission early. But in every other case, just go for it!

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