How I’m living, creating and making a killing without their permission.

Written by Cole Schafer


It’s Monday morning and it finally feels like summer here in Chicago. I’m sitting in a small coffee shop called Intelligentsia with my back to the window. The sound of passing cars and people offer a frenetic white noise that makes writing easy. Or, at least, easier.

I’ve lived in Chicago for three weeks and the prettiest words I’ve found to describe it are… Everyone seems to be running late to a party the rest of the universe knows nothing about.

Perhaps, Chicago is just a more extreme concentrated focus of humanity-at-large. But, I digress.

Anyway, today is noteworthy. That’s why I’m writing.

Honey Copy, my creative writing shop that works with brands on writing pretty words that sell whatever it is they’re selling, is booming. Just absolutely booming. And, I feel so wildly fortunate.

My newsletter, Sticky Notes, just hit 4,500 subscribers. My writing guide, How to sell like a Florida Snow Cone Vendor on the hottest day of the year, has done $17,227 in sales to date. And, I just started writing for a brand called Butterfly IQ that is changing the world.

(Oh, and I sent my book, One Minute, Please? off to my editors… but that’s a story for another day.)

I write all of this for two reasons…

For one, I can be pretty self-critical and at times working, living and creating as both a writer and entrepreneur can feel like I’m running in place –– writing this shit down is a good reminder that this isn’t the case.

And, two, I hope by sharing some of my modest success (in a not so modest way) that it gives me some small degree of credibility as I go on to share a life philosophy of mine that certainly isn’t normal.

While I can’t say my way of living will work for everyone, it has worked for me. And, I think as writers, all we can do is share our perspectives in the truest, rawest, most honest words possible.

So, here’s how I got to today.

Learning to live without their permission.

For most of my life, I followed the rules.

And, I don’t blame myself for doing so because it was nearly impossible not to.

The education system in the United States is very much designed to transform young people into obedient professionals that follow instructions, clock in and out on time and don’t ask questions.

For the most part, our education system still heavily aligns with that which was created during the industrial revolution. Factories needed obedient workers and so a curriculum was designed to produce obedient workers at scale.

In the twenty-first century, the scantron sheet is perhaps the best example of where this education system fails us.

Students are graded not on their ability to ideate original creative solutions to real-world problems but rather how well they can fill in the “right” bubbles.

That’s just absurdly ridiculous.

I remember right out of college going to work for an advertising agency in my hometown and feeling shell-shocked as I experienced how wildly different the real world is to the sort-of simulated world that is created for us in our schooling.

Everyone is taught extensively about “parallelograms”. Yet, still to this day, I can’t figure out a way to apply what I learned about parallelograms to tax season.

It truly is unfortunate there is no parallelogram season.

While I don’t want to say traditional education is total bullshit, I do think it needs a massive restructuring.

And, I feel very confident saying that if you are reading this right now, you are at a disadvantage in today’s world because of how you were tested, guided and disciplined during your education.

Now, back to my time at the advertising agency.

During my time working at the agency I mentioned earlier, I realized I had a knack for something called “copywriting”. Or, selling stuff with words.

While I was by no means the reincarnation of Ogilvy, I quickly saw that my prowess with the pen offered brands some serious value.

One day, I found out my boss billed clients quite a bit more than she was paying me hourly. Upon making this discovery, I put two and two together and realized if I went out on my own I might be able to bill just as much.

Now, if you were to ask the vast majority of people what to do in this situation… the traditional advice would be something along the lines of… “Be patient, you have to put in your time.”

Or, in not so many words… “Yeah, that’s shitty. But, it’s your first job. It’s part of it. It’s just the way the world works. Accept it.”

I did something different, though.

I quit.

During the day, I took a job at a construction company making around the same wage as I was at the agency. And, at night, I began cold-emailing hundreds of companies asking them to pay me $50/hour to write for them.

While to some, this might sound crazy, it wasn’t.

At the time, I was saving brands quite a bit of money working with me directly rather than an agency and I was setting myself up to make 5x what I had made at my previous job.

With that said, it wasn’t easy.

While a lot of the folks I had graduated with were off making great money working big fancy jobs in big cities, I was living with my parents, working construction during the day and building a floundering freelance writing business that would one day miraculously blossom into Honey Copy.

But, none of this mattered, because for the first time in my life, I had done something without their permission.

Or, in other words, without the permission of a parent, a teacher, a coach, a mentor, a friend or a boss.

Giving myself permission to do something rather than waiting for someone else to give me permission changed everything for me. It changed the trajectory of my career. It changed me fundamentally as a human-being. It, ultimately, changed my life.

But, enough about me.

Let’s talk about you.

I think that many times we follow what has already been done not because we’re incapable of leading ourselves but because it’s easier, it’s safer and it’s far more comfortable.

In addition, it’s what we have always known.

When you’re taught to raise your hand to ask permission to go to the restroom for over a decade of your life, it becomes both extremely difficult and uncomfortable to make big life decisions without asking the permission of others, first.

And, because of this, instead of making decisions that feel right to us, we make decisions that follow the norm… decisions that are socially acceptable.

Asking for permission is but a small piece of a much larger bullshit-filled cake that we’re all eating and that’s this misconception that there is a certain way all of us must live.

The greatest innovation killer (and dare I say happiness killer) is… “it’s always been done this way.”

If working with startups has taught me anything it’s that rarely (if ever) is the traditional way of doing things the best way, let alone the only way.

And, while I don’t encourage people to drop-out of college nor build a business nor go work for a startup… I do encourage people to give themselves permission to live the lives they want to live.

One of my favorite lines on this idea is by the late great computer scientist, Grace Hopper… “It’s easier to ask for forgiveness than it is to get permission.”

I think all of us, in our own lives, need to be doing more apologizing than asking. Because, from my experience, when you have the courage to act without asking, it works massively in your favor 99% of your time.

And, for the other 1% of the time…

Well, that’s what the word “sorry” is for.

By Cole Schafer.