How drawing changed this artist’s life and led to a $45K paid newsletter

Danny Gregory threw his art in the trash on his way out of the studio his mom and sister rented him for a month as a gift.

He’d been working in advertising for years. But people noticed he was always making stuff outside of his job. They sensed there was an artist in him.

But when Danny walked into that art studio for the first time, he felt mostly panic.

It was like you have a fantasy; then suddenly, it becomes a reality and nightmare. Because I had to confront the fact that I just had no idea what to do—and a month felt like a long time and also a short time.

On his first day in the studio, he walked into the empty space and sat on the floor. He journaled why he wasn’t sure what to do in this studio. He did one “not very good painting.”

It was a failure.

At least, that’s how he saw it then. But it turned out it wasn’t a failure at all.

Danny didn’t know then that eventually, something would be unleashed in him that would ignite his art-making in ways he couldn’t even imagine then, nor that it would one day turn into a successful creator business after he left his advertising career.

He also didn’t know then that art would play an important part in helping him through two unimaginable tragedies that were about to change his life forever.

“The world intruded and made me feel like I couldn’t do it.”

Danny loved making art as a kid, especially books. He carefully folded single pieces of paper to form tiny “books,” writing on the left pages and drawing on the right.

But when he got to high school, he stopped making art.

Ultimately, the world intruded and made me feel like I couldn’t do it. 

Before high school, Danny lived all over the world. His mom was born in Pakistan, he was born in England, and they lived in places like Israel and Australia. So when Danny came to the US for high school, he felt out of place.

It was a confusing time. 

I think when you’re in high school, you want to belong.

But in high school, art making is a clique.

Some people are jocks, then there are nerds, and art people. And I wasn’t sure what group to be in.

He didn’t know where he belonged. He dabbled in the groups but never felt like he fit anywhere. And even though he liked to draw, he concluded that being an artist wasn’t possible.

I felt like I couldn’t be an artist. I’m not gonna go to art school.  It felt like a really appealing and attractive road, but I just didn’t feel secure enough in it. 

The thing about art-making is I think you end up feeling so judged by the art you make and what other people think of it. And are you successful, and are you any good? And there’s always somebody who drew better than you.

So Danny left art behind, majored in political science, got a job in advertising, married a lovely woman named Patti, and had a son.

Every day, Danny woke up, said goodbye to Patti as she went to work, said goodbye to his son, who was with a babysitter, and went to his office in New York City.

On one of those days, when he and Patti were in their early 30s, and their son was nine months old, while Danny was working on location for a photo shoot, the police showed up and pulled him aside. “There’s been an accident,” they said.

All Danny remembers is that they said something about his wife’s leg, and then he went to the hospital.

His wife had been in a subway accident and was now paralyzed.

In one instant, everything about our life was different.

Patti focused most of her energy on healing and the logistics of learning how to live her life in a wheelchair. Danny helped where he could, but when he wasn’t busy caretaking, he found himself lost in the existential grief of it all.

He struggled to find grounding or beauty after such a traumatic event.

And then, one day, I just had this urge to draw. 

He started by drawing what was right in front of him, their medicine cabinet.

As he carefully copied outlines of orange-lidded medicine bottles into his sketchbook, something changed.

For the first time since the accident, Danny felt his breathing slow. His constant worry melted away. For a moment, he was in the moment. And for the first time in a long time, he saw that even pill bottles could be beautiful if you really stopped to look at them.

If you look at something and try to draw what you’re looking at, you are connected to reality. You’re right there in this moment. You’re looking, you’re seeing, and everything else kind of fades away.

So suddenly my feeling was, Okay, life is good. Which is something I hadn’t felt since the police had come to get me that day.

For the first time since he was a little kid, Danny remembered what it felt like to make art apart from judgment—his own and the world’s. He remembered what it felt like to make something just because.

I was drawing stuff around my house–an old shoe, a toilet, my dog sleeping, whatever it was. You start to realize everything is beautiful.

All these things add up, and make you feel full of possibility and hope. That was what I needed. 

He started drawing again. And then, he discovered the power of the internet.

“It became a community by accident.”

Danny’s first introduction to how the internet could change his life was in the mid ’90s, after his wife’s accident.

The internet was, as he says, “a different place than it is now,” and he struggled to find the information they needed about wheelchairs and how to help his wife rebuild her life.

But Danny kept searching and digging, saving all the helpful links he found.

Since he’d wished all of that information had been curated in one place, he decided to build his own website and share those links so other people could easily find them. He was always fascinated by the internet and thought creating a website sounded interesting.

He didn’t know if anyone would find the website, but they did.

So much so that a community formed around the content in the comments sections. As he explains it, there were a lot of people in wheelchairs on the internet in the early days, because for them the internet “was a way of getting around.”

In the comments section, people shared even more helpful information. And since many of them struggled to leave the house as freely, they enjoyed this alternate way to socialize and connect.

I ended up building a community around this thing, and it became a community by accident. 

Through that website, Danny accidentally learned how to build a community.

So when he started drawing and making art again, he decided to build a community on purpose to connect with other artists, especially those who did illustrated journaling like he was doing, recording life in sketchbook form. 

He wrote his book Everyday Matters, about how he discovered drawing, and then created a community online around the idea, using Yahoo! Groups and the then-popular photo-sharing app Flikr.

That community grew to 5,000 people who shared over 150,000 images of their artwork together.

Danny wasn’t trying to start a business. He already had a steady job in advertising, where he was moving up the ladder to become a creative executive and winning many advertising awards.

I had no reason to go out and create a business. I had a successful job. 

Just like his passion for art, the community itself was valuable in and of itself. None of it needed to be monetized to be valuable.

But then his life turned upside down, again.

“Art made it easier for me.”

In 2010, while watering plants on the balcony of their eight-floor apartment, Danny’s wife Patti slipped and fell eight stories and died.

My life broke in a lot of ways. 

Their son Jack was now 15. After her first accident, there was a lot to do. After this one, there was, as Danny says, “a different kind of hole.”

So much of the first accident was, How will we manage our lives around this thing? I still had her there. 

When she died, I didn’t have that anymore. 

He was also now his son’s only parent, which became his focus.

But there was one more thing that was different about the immediate aftermath of this tragedy as compared to the first.

I had art. 

Due to immense grief, Danny couldn’t make art in the immediate aftermath of loss. But unlike the first time, the practice was there, not to mention the pens and the paper. This time it was waiting for him whenever he was ready.

Before Patti died, Danny had been in a phase where he was only drawing in black and white. A week after Patti died, he started drawing again–in color.

I did the brightest, most colorful stuff I’d ever done. 

Patti had been in the fashion business, he explains, and she loved color.

Making art helped me experience what I was going through instead of suppressing it or denying it. Art made it easier for me.

Once Danny fully realized the power art can have in and of itself, he couldn’t keep it to himself.

He wanted everyone to know what a difference it could make, and that impulse to share, just like he did with his website to help others in wheelchairs, led him to start a creator business that would grow to become more than he could’ve ever imagined.

“Maybe it’s time to finally go and see what else I can do.”

But Danny’s next leap didn’t start with a dream to become a creator.

He just knew that after 30 years in the advertising industry, he’d gone as far as he wanted to go in that world.

He’d risen the ranks and done award-winning work, but he’d also been creating, writing books, and blogging about the creative process on the side. He felt the advertising industry was slow to respond to the changing media and internet landscape.

I saw these great tools out there; now, there is the opportunity to have one-to-one conversations with people and sell in completely different ways, to tell your brand’s story.

I would push that in businesses I worked on, and people just didn’t get it. I was frustrated and bored in a new way. 

And I thought, maybe it’s time to now finally go and see what else I can do. 

Danny eventually remarried, to a woman named JJ (Jennifer James), and when she got a job in Los Angeles, he quit his big city advertising job and moved across the country. He was grateful for the escape, unsure if he’d have been able to avoid accepting another job offer in the advertising business had they stayed in Manhattan.

He didn’t know anyone in LA. But they had a house with a garage, which became Danny’s art studio.

I started painting for the first time. I was able to make stuff, and it was good.

But quitting his job and not knowing what was next was also unsettling.

I was anxious a lot about it. I didn’t know where to go. 

I had clung to security for so long. I really stepped off the cliff, and I had to trust that something would happen. 

If things went south, I could just crawl back with my tail between my legs and get another job in advertising.

He was grateful that he also had the resources to take some time to figure it out. He’d saved from his previous career, and now he didn’t need to rush into anything. For a time, he created in his garage and followed his curiosities.

Those curiosities led him to online courses. He’d seen people starting to create them, though in those days, most were either written-only or filmed with very poor-quality webcams.

As someone who’d produced Super Bowl commercials, Danny had a spark of an idea: what if you created an online course that looked like it could be on TV?

“A thing that we don’t think about with artists is also being a business person.”

Danny wanted to create something that was a mix between an online course and the Netflix docuseries Chef’s Table, which had just come out at the time.

The series deeply inspired Danny. Instead of a more traditional cooking show that teaches the audience how to make something, Chef’s Table was about how the chef was made.

There’s so much content around food but not much around art, even today. 

I wanted to tell the story of being an artist. Not just how to make art but how to be an artist. 

Danny also thought Chef’s Table did a good job of showing the full spectrum of what it really means to be a creator for a living.

A thing that we don’t think about with artists is also being a business person. It’s not just like, Oh I want to express myself. It’s also employees, rent, and managing things.  

I think that’s another thing that a lot of people don’t think about. That you’re going to have to learn a lot of skills that are beyond just your creative act: finding a platform, paying taxes…a million things nobody teaches you. 

My son went to art school, and they don’t teach you that stuff. They don’t teach you the practical aspects of an independent business person.

Danny wanted to create a course that merged the artistic and the practical and used documentary storytelling as a way to teach.

He partnered with someone also interested in creating something like this, and they created a one-off six-week online course where students would learn from a new artist virtually from their studio.

You would go to their studio, they would show you around and show you their materials. They would take some sketchbooks off the shelf, take you through them, and then tell you some stories like this is how I started, this is what I was l like when I was young, and here’s my progress.

They would also say, here are some lessons I’ve learned and some things you should do. And then, they would sit down and make a piece of art. And so there would be a demonstration and a piece of homework.

At this point, Danny had been building his audience for over 15 years. When he started working on the course, he also blogged about it. So when they launched the $99 course, 1,800 people signed up.

It was only supposed to be a one-off thing. But he quickly realized it could be more if he wanted it to be. People were clearly hungry for this kind of instruction, storytelling, and artistic community.

So Danny and his partner created a second class. And then another, and then another, and Sketchbook Skool was born.

By 2014, it was Danny’s full-time job. Soon his wife JJ also joined, and it became a vibrant company, growing over the years to have hundreds of classes a year, 200K+ YouTube subscribers, and popular live events.

He was thrilled with this new career, but being a professional creator was also overwhelming.

“There are always new platforms.”

Danny loved working for himself, but he also couldn’t shake this new feeling, this “constant sense that there’s always more to do.”

There are always new platforms. New opportunities. New people telling you you should tweak this, and you should tweak that. There are ups and downs, and things that you thought were working well now don’t work as well.

Things are constantly disrupted. There’s a billion things you can do, and my eyes are always bigger than my stomach.

When deciding what to focus on, especially because it’s important to him to still protect time to create his own art, he asks himself one question.

Coming back to strategy is really important, which is to say: Yes, you can, but should you?

Social media, in particular, dangles metrics in front of you all the time: this many views, this many likes, this many followers. What does that actually do for your business? 

I think it’s important to stop and say, is this gonna convert to anything that’s a meaningful metric? 

You can have these things, but there are only so many hours in the day.

Having an email list has always been a part of his strategy, but as Sketchbook Skool grew and Danny found he wanted to create a space for just himself as an artist again, like his old blogging and community days, he switched his newsletter to Kit to make that connection and write directly to people again.

What I liked about Kit was it was developed by creative people. I had been blogging for all these years but I didn’t feel like I owned my list.

I felt like I was always doing it on somebody else’s platform. I liked the idea of newsletters and that was where I wanted to put my effort. 

Danny writes his essays on Kit and sends them out as newsletters, and then turns those essays into YouTube videos by reading his essays on camera. He says those videos have become successful lead magnets that drive free and paid subscribers, as well as book and course buyers.

The newsletter is at the core of cementing relationships that become transactions over time.

Danny’s email list on Kit has grown to more than 20,000 subscribers. His paid newsletter has made $45K+ to date, and he’s selling his latest book through Kit Commerce.

“Okay, so I’m not good enough.”

Danny also gets 100+ weekly email replies to the essays he sends out, and he’s grateful for the opportunity to have such a direct connection with his audience again.

It’s easy to get seduced by how many subscribers you have or those other metrics. But it’s the human one-to-one things that make it worth doing.

Now you don’t need to go through galleries or art schools. You can make art, find an audience, and share it directly. 

Although the increased access doesn’t change the sense of hierarchy still often applied to art, the kind Danny says he started to sense even as a kid.

There comes a point where you start to sense hierarchy: “He’s better at it,” or “He’s really talented,” or “You’re not that good at it.” 

In college, Danny wanted to take a creative writing class offered at his school that you had to apply for to get in. Danny applied, but he didn’t get in.

And so I was like, okay, so I’m not good enough to get into the class. And that was it. 

And by “it,” he means that was the end of his writing dreams.

He figured if he wasn’t good enough to get into the class, he would never be good enough to get a literary agent, the only way it seemed feasible at the time to become a writer. So Danny figured he’d never be good enough.

But when Danny first started sketching after his wife’s subway accident, it also unlocked the part of him that had wanted to take that writing class all those years ago. To date, he’s written 13 books with thousands of 5-star reviews.

For Danny, writing, creating, and sharing those books has been a dream come true, especially when he thinks about the kid he used to be, folding a single sheet of paper over and over to form a tiny book.

But what drives Danny most as a creator is his deep hope that in his work, people find a spark to create their own work.

My goal has not been to be somebody who makes art that people buy, but to be somebody who gives people an awareness of the power of art making and how that’s a power we all have. 

And while he deeply believes in the power art has apart from monetization, he’s also grateful for how the internet makes it possible for more artists who want to make a living with their work to have the opportunity.

He also believes it’s never too late to start creating and that professional creators already making a living with courses or podcasts, or some other income stream, could also consider adding more art into their lives, either as a meditative practice or even as another income stream in some way, if they want it to be. Because as he puts it:

 I think you can find an audience for anything.

It may not be a huge audience, but it may be a really deep and dedicated audience. So I say focus on what you really like doing. 

And if you do it well, then there will be people who find you.

But if you try too much to do what is trendy, what is tested, what is popular, I think you’re less likely to get to that place. 

You may not make as much money, perhaps, as somebody who’s done all the data crunching, but you’ll be fulfilled in other ways, and you’ll continue doing it for longer because it means something to you.

You can connect with Danny on YouTube , subscribe to his email list, or learn more at dannygregory.com.