May 13

Should You Ask for Permission or Seek Forgiveness?

I’ve seen this saying bandied about a lot: “Don’t ask for permission. Ask for forgiveness, instead.” It seems to be a culturally lit and, dare I say, a Silicon-valley-appropriate phrase (especially when there’s VC money involved.) Half-kidding!

In all seriousness, though, the saying is well-intentioned and has its heart in the right place. Without realizing it, we put our most vivid dreams on the back burner because we wait for permission that may never come.  

When R Sheinberg lost his well-paying but insanely draining job as an investment banker after the 2008 financial meltdown, he had a couple of choices before him. Either pursue other similar jobs in finance while taking a pay cut or pivot to start a risky business in the industry he always dreamed of being a part of—fine wines. He chose the latter.

Sheinberg used the layoff from his finance job as a permission slip to start a business importing fine wines from Europe.

Why did Sheinberg wait until he was laid off from a job he found unfulfilling to start one he was passionate about? Beyond the usual explanations of financial security and risk tolerance, there’s a much more fundamental reason why, like Sheinberg, we shelve our dream careers, interests, and hobbies: we feel the need to ask for permission. From whom? Everyone, I guess.

And for that, we can thank nurture, not nature.

The trouble with adulting

Being an adult is like folding a fitted sheet. (Internet wisdom.)

I couldn’t wait to be an adult when I was a child. I wouldn’t have homework, I could come and go at my will, AND I’d have a car and money at my disposal. What’s not to like about that? But then I became an adult and was bummed to find out it wasn’t all that it was hyped up to be.

It did not take long for me to realize that adult lives aren’t free. At all. Every step is a permission-seeking venture.

When you apply to a college, you are essentially asking the admissions officer, “Am I good enough for you? Will you permit me in?” And the saga continues through jobs as you chart your career trajectory. Every performance appraisal session is a plea: you showcase how you’ve done your part; now, please, can they give you a raise and/or a promotion?

It doesn’t stop there, though. You ask for permission to be a friend or belong to a social network (offline and online). And so on.

Nature v Nurture

But we weren’t born this way. If you’re a parent or have been around toddlers, you’ll know. Little kids don’t seek permission. From the time they jump out of bed until they pass out at night, toddler life is just a series of experiments to see how far their curiosity will take them.

This mom’s tweet about her child describes toddlerhood perfectly.

Get off the table. Stay away from the trash. Stop licking old pizza. Don’t play in the litter. -Me, talking to my 2yo, not my cat. Salty Mermaid (@Jenn_H_Scott) February 27, 2016

Over time, though, we learn not to put our fingers into power sockets. Or shove peas up our noses. Because our parents and other responsible adults around us tell us not to. Or, to be honest, getting an electric shock or feeling your nose burn aren’t pleasant sensations.

In the process, we learn about fear and uncertainty.

And then, subconsciously, just like that, we start to imbibe the permission mindset—we begin to ask for permission (or approval) to do just about anything.

Here’s the problem with waiting for permission. You could be waiting all your life, and it may never come.

The road less traveled

Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference. Robert Frost, The Road Not Taken.

When Alex Honnold free soloed (climbed alone, without ropes or assistance) Zion Canyon’s Moonlight Buttress in 2008 and then the imposing 3000-ft vertical cliff, El Capitan in Yosemite, in 2017, the world was astounded. Described as one of the most incredible athletic feats ever, Honnold did something no one had attempted before him. In fact, no one even thought it was possible to free solo up El Capitan.

In his opinion piece, author Daniel Duane writes that while what Honnold did is extremely dangerous and may even seem outrageous to most, he was born with unique neural and physical gifts. This, combined with a lifelong dedication to honing his talent, propelled Honnold to the top. Duane describes Honnold’s El Capitan climb as “a performance so far beyond our current understanding of our physical and mental potential that it provokes a pleasurable sensation of mystified awe.”

Honnold didn’t just shock and awe alpine-climbing enthusiasts. He made humanity pause and consider this one question: “What if I could …?”

What does it mean to ask for permission?

We may be putting off dream projects because (unwittingly) we are waiting for someone to give us permission.

Asking for permission may be hard to recognize because, like a chameleon, it can camouflage itself in many ways. Here are some:

Identifying the problem is half the solution.

1. Not wanting to upset the applecart

Sometimes we put off our vision for the world because we don’t want to challenge conventional wisdom and upset the apple cart.

We, humans, are a social species. Evolutionarily our very survival has depended on us belonging to a group. So, people-pleasing is a part of our psyche.

But it can be much harder to please people or get backers when you’re attempting to be creative or innovative.

How can you seek approval from someone who doesn’t even understand where you want to go? It’s like asking someone to value a Russian-language copy of Dostoevsky’s Crime and Punishment when they do not read or write Russian. To them, it’s probably just another book.

2. Well-meaning curfews

Surprisingly, and somewhat annoyingly, sometimes it’s your well-wishers who deny you permission when you’re about to start on a new venture.

The resistance usually comes from a place of good intention and sounds something like this:

“The internet is an insanely competitive space, and while I’d like your new business to succeed, statistically, there’s a low probability of that happening. Instead, why don’t you find a good, stable job that pays benefits and insurance?”

Whether you are a wannabe writer, an aspiring musician, a budding Etsy artist (yes, there is such a thing), dream of being a digital nomad, or <insert your own adventure here>; you are likely to encounter pushback.

3. Impostor syndrome

Not sure about the Force, but the resistance is usually with us, or to be more precise, within us.

A key reason we ask for permission is that we inherently doubt our own capabilities. Impostor syndrome and self-doubt are like twin toddlers. You think you’ve quieted them down to nap time, but the second you try to do something, they’re up again, wanting your attention.

Self-doubt is really just another way of asking yourself for permission to do something (and the answer is usually no.)

Then again, sometimes you do need to ask for permission

The obvious needs to be stated.

 “Don’t ask for permission. Ask for forgiveness instead” isn’t a blanket rule for all situations. Take stealing or murder, for instance. Or, when rebellious teens take this saying as gospel.

Princeton professor Samuel Hynes in his book The Growing Seasons: An American Boyhood Before the War, says this of rebellious kids he encountered in his childhood.

They were just against: against parents, teachers, cops, preachers, scoutmasters, school principals; against all signs that said DO NOT and KEEP OUT; against fences and walls and ropes at the beach; against everything that spoke for authority. If you were against everything, then you were free.

So, just to be clear, I’m not recommending that kind of against.

“May I?”’s are equally important in our lives, especially when it’s the right, polite, human thing to do.

Ask for permission before you interrupt a conversation, or borrow your neighbor’s lawnmower, or put your family home up as collateral for a risky business venture. In short, whenever you put another person’s time, property, or life at risk, it’s prudent to ask for permission.


Stephen King was a gas station attendant living in a trailer when he finished his first novel Carrie and sent it to thirty publishers. He got thirty rejection letters. He persisted and went on to become one of the best-selling authors of the century.

King reminisced in a National Book Awards ceremony,

If my wife had suggested to me even with love and kindness and gentleness rather than her more common wit and good-natured sarcasm that the time had come to put my dreams away and support my family, I would have done that with no complaint… If she had suggested that you can’t buy a loaf of bread or a tube of toothpaste with rejection slips, I would have gone out and found a part-time job.

It would be nice to have other people bet on you. And, if they don’t, it’s disappointing but understandable.

But, to not bet on yourself? That would be a travesty. Life’s too short for that.

If there’s one takeaway from this article, it’s this: ask yourself, “What if I could …?” Then reflect on why you haven’t. Are you simply waiting for someone to give you permission?



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