How can you go from a day job you don’t like to doing work you enjoy?

How can you start your own business?

How can you achieve the life you want?

You have two options:

  1. Quit right now, try to do everything you want all at once, and hope it works out, or
  2. Overlap.

When you overlap, you don’t immediately quit your day job. You use the day job as a foundation to cover your bills while you do something else on the side. Eventually, you’ll let go of the day job, but only when what you want to do can support you entirely on its own.

To prove that this process works, here’s how I unintentionally overlapped for years until I realized the power and potential of overlapping.

The Window Cleaner

The window was forty feet up, and we weren’t sure how we were going to get to it. The house near the lake had three stories, and the window we wanted to reach was at the very top.

“We’ll have to use the thirty-two.”

Our thirty-two-foot ladder was always strapped to the truck, but we rarely ever used it. No, we weren’t robbing the place. We were window cleaners, and most residential jobs with two-story houses required no more than a twenty-four-foot ladder.

The thirty-two would get us to the edge of the top roof. But once we got there, the highest window was another ten feet up.

“We could bring the four up with us. I’ll hold it for you.”

“I—I don’t know,” I said.

I knew the four-foot ladder would work. I also knew it meant I’d have to stand on the very top part that says “DO NOT STAND ON!”

My partner assured me he’d hold the base of the smaller ladder and it would be fine. But I knew he would be at the top of the thirty-two-foot ladder himself.

This seemed like a bad idea. Being a teenager, I decided we should do it.

I can’t even tell you how I got there, but the next thing I knew, I was standing on the four-foot ladder near the edge of the roof of a three-story building. I leaned over and extended my arm as far as it would go to wipe off the last few drops of water from the corner of the window.

“Woah!” said my friend, struggling to keep the ladder still.

I shot him a threatening look.

At this point, I started to rethink things. Not just our precarious position, but all of my life and career choices that had led up to this moment.

Window washing was an exhilarating, adventurous, memorable, dangerous, sweaty, grueling job. The people you worked with were like family. That’s how we thought of each other anyway, because if you’re going to die . . . you want to be around family.

Fortunately, I didn’t die. We somehow made it out alive, as we always did, but I wasn’t keen on continuing to roll the dice.

The Computer Repairman

The band I was in at the time decided to go full time, and I figured this was as good a time as any to quit the window-cleaning job. I played piano and guitar in the band as we toured for a few months.

After returning from the tour, we quickly realized we’d each need to find supplementary income to support ourselves.

I decided to start a computer repair business. I was still in high school at the time. I had friends and neighbors who constantly complained about their computers and problems they couldn’t fix. Sure, I knew how to fix most problems, but, more importantly, I also had the willingness, drive, and determination to figure out how to fix any problem I didn’t know how to fix.

There was no problem I couldn’t fix—it was simply a matter of research. I applied myself to each and every problem I encountered and went until I solved every single one, even if it meant taking a client’s computer home and staying up all night to figure out how to solve the problem.

I started out severely undercutting the competition in terms of price. While the big repair companies charged exorbitant rates, I had a modest fee and even performed on-site service at no extra charge in my local area. Everyone was so grateful—guilted, even—that they regularly tipped me. It didn’t take long to realize I was undercharging.

I doubled my rates. At this point, I was out of high school and spent the majority of my time working. Not a single client complained about the price. I was amazed and overjoyed because I felt like I was making great money. I look back with the knowledge I have now and immediately recognize the fact that I should have charged even more. (If not even a single client out of hundreds complains, you’re charging too little.)

One repair job I did was in a neighborhood that sent out a regular newsletter. This newsletter contained service recommendations from the residents. Anytime someone felt like a contractor or company did a great job, they recommended them in the bi-weekly newsletter.

I started getting lots of calls. I was doing three, four, sometimes five or more jobs a day—and the vast majority of them were in the same neighborhood! This meant my job sites were often only a few streets apart. I’d struck a gold mine. Every great job I did landed me another spot in the next newsletter. I’d practically earned a permanent feature without paying a single cent in advertising. The neighborhood was primarily comprised of older, wealthy residents who were more than happy to throw money at a trustworthy young man recommended by someone they knew.

Eighty percent of the problems I encountered were identical. I had processes in place to virtually automate the repair of the most common problems to the point of boredom. I had to pretend to look busy in these cool, fancy, air-conditioned homes while sitting in a comfortable chair. It was so easy, I could have done it in my sleep. I’d often come home with hundreds of dollars in cash just from a few hours of work.

I knew I would never again work for anyone else for the rest of my life. I decided to stop pursuing a computer science degree and focus on my business instead.

A lot of these older rich people I worked for had their own businesses. I soon found myself shifting from doing only residential work to including more commercial work. Once I started servicing more businesses, jobs become even more lucrative. No longer did I have to go all the way out to one residence to repair a single device. I could visit an office and service half a dozen machines on a network and make even better money in less time. The referrals I got from businesses were, of course, other businesses, which led to more of the same work.

Starting the computer repair company taught me so much. Diving in head first, I learned a ton about business very quickly. I learned how to handle my accounting, deal with local and federal taxes, work with clients, write proposals, send invoices, price my services, and so much more. Most importantly, I learned the power of word of mouth. This was the beginning of my foray into business.

The Web Designer

My clients started asking if I also built custom websites. I had built websites in my spare time—personal projects and websites for friends—but never for professionals. Not one to back down from a challenge, I said “Yes” and set out to learn on the job. References from a few friends for whom I’d done freelance work in the past were enough to land me my first web development project. I gradually expanded my portfolio and started to get more and more website projects. This was my first official overlap. From 9:00 a.m to 5:00 p.m., I traveled across town and repaired computers. On my nights and weekends, I designed and coded websites.

The more websites I built, the more I enjoyed it. It got to the point where I was receiving so many website job requests that I had to turn most of them down.

A tremendous number of job requests were coming in, but I had nowhere near enough capacity to take them on in only my nights and weekends. I was already working sixteen to eighteen hours a day.

I needed help.

I called up a buddy who worked as a developer at a local firm to ask if he wanted to start a web design firm together. He said yes, and three months later we started the firm. Right around this time, I married Laci, my girlfriend of four years and now wife, and we moved into an apartment together. My business partner and I decided to split the cost of another apartment right across the hall from the unit I lived in to work out of as our office. My commute was about eight steps.

Meanwhile, the computer repair business (my “day job”) was as busy as ever! I knew the web firm was going to require most of my time if it was going to succeed. I couldn’t keep running the computer repair business at full capacity on my own, so I hired an employee. I spent a week or two training him, and then he took over all of my jobs. I spent one hour each day handling the scheduling and accounting for the computer repair business and spent the rest of my day at the web firm.

The computer repair business was going well, but it wasn’t growing. I wasn’t able to dedicate any more time to it. Had I been able to focus on it, I could have hired more technicians, advertised, scaled it, and it would have been an asset to me, but I knew I was never going to dedicate the time. A year into starting the web firm, I sold the computer repair business to my employee.

The web firm was now my full-time day job and my full focus. Once again, word-of-mouth referrals were our greatest source of new jobs. Our work came almost exclusively from one highly networked group of clients that kept referring us. There wasn’t much variation in the type of projects we were doing, but they paid well enough, so we didn’t complain.

I continued to work an average of ten hours a day at the firm, five days a week, but now my nights and weekends were free. I no longer did computer repair, and web design completely paid the bills.

During the day, I designed user interfaces and ran the business side of things at the firm, but what was I going to do on my nights and weekends?

The Hand Letterer

I checked my inbox one morning, and, to my surprise, a well-known designer I’d never met before had sent me a message out of the blue to let me know he was going to be in town. He’d found me online by searching for designers in the city he planned to visit—my city. He asked if I wanted to get coffee.

Over coffee, we ended up talking about hand lettering. Drawing letters by hand allows you to create unique artwork that would not be possible using only fonts. I used to doodle on my homework and in middle school I would often spend more time writing the lesson name in fancy letters than I would spend doing the actual homework. It wasn’t until years later I discovered typography and lettering and learned that there were names for various fascinations with letters.

This designer said, “If you enjoy hand lettering, just start creating. It doesn’t have to turn into a job or something you make money from. Just start creating.”

This was the first time someone encouraged me to pursue something because I enjoyed it. Sure, I’d always wanted to do work I enjoyed, but I was under the impression that it was allowed only if you could somehow make money. It didn’t even occur to me that I could do something solely because I enjoyed it.

On my nights and weekends outside of my work at the web firm, I started creating hand lettering. For six to eight hours a day outside of my ten-hour day job, I would draw letters. Every single evening, without fail, you could find me at my desk drawing. I drew every weekday night and all day on the weekends. I didn’t watch movies, I didn’t watch shows, I didn’t play games, I didn’t go out with friends, I didn’t read books—I did nothing else in the evenings except draw.

Whenever I finished a piece that I liked, I posted it online. I did this for two years, and no one really noticed. That was okay because I wasn’t doing it for anyone but myself. I enjoyed the act of drawing. It was never about fame or recognition.

After showing up every day for two years, it was almost as if a light switch turned on. It seemed as though people had suddenly noticed my work! Suddenly, people cared. After two years of showing up daily without fail, people began asking, “Can you design a logo for me? Can I get prints or T-shirts of your work?” I was blown away.

Instead of spending my nights and weekends creating for myself, I shifted to doing custom commissions for money. Since I had my day job, all the money I made was extra. I didn’t need the money to pay bills, so I saved every bit of cash I made from client work.

When I had enough money saved, I invested in a large run of custom T-shirts featuring my most popular design. The T-shirt sold out. Then it sold out again. It continued selling out. The investments I’d made during my nights and weekends for two years were paying off.

By this point, we’d been running the web firm for three years. Every year, we entered into a slow season with client work around the holidays. Running your own business is tough. When there’s a lot of work, things are great, but you have to be ready for inevitable dry spells.

We were very big on staying professional and taking on only the right type of clients. We decided from the beginning that we were not going to compromise our values. There was no way we would ever make it as a long-term business if we compromised our standards. We needed to be selective with the clients we accepted. If things ended up not working out, we would move on to something else. We weren’t willing to work with the wrong type of client just for the money.

It wasn’t easy. In fact, we ended up paying the price for our standards. When we entered into a dry spell during our third year, my partner said he was going to apply for a full-time job because he had to pay his bills. I told him I completely understood.

The Graphic Designer

At the web firm, we also did branding in addition to web design. This meant whenever my hand-lettering work on the side brought in logo design jobs, I’d say, “Right this way: I work at a web firm where we can handle your branding or logo design.”

Design was my specialty at the firm, so it was my responsibility to do any and all design work. This meant I would get half of the money from the logo design job because it was a partnership and we split the profits. That’s how it works and I knew that going in. I respected it, always referred any potential clients, and cheerfully did the work for half the money under the name of the firm. When my partner decided to get a full-time job elsewhere, we hibernated the firm. This meant I was now able to effectively make twice the money for logo designs while charging the same rate because I was working on my own instead of in a partnership.

I learned a lot from running the web firm for three years. I learned that you have to treat partnerships like a marriage. I learned that professionalism is costly—it is always worth it, but you have to be willing to pay the ultimate price. You have to be willing to say “No” even if you’re desperate. We may have hibernated the firm, but we didn’t lose our dignity. I learned that when you start a business, you’re going to end up spending twenty percent of your time actually doing the thing you love and eighty percent of your time running the business. I never did so little design work as I did running a web design firm.

Don’t start a business unless you love business. I had no clue about this going in. Fortunately for me, I fell in love with business.

I was overlapping again—only this time, it wasn’t an intentional overlap. I hadn’t actually been aiming to do hand lettering full time; it just sort of happened. I found myself without a day job and left with a passion that was already making money. We were already sending out physical products every day and people were still asking me for work, so I figured I should give it a try and attempt to make a living as a hand-lettering artist.

Learning is something I’m very passionate about. If you aspire to one thing, let it be learning to learn. When you love to learn, nothing is unattainable for you. My love for learning randomly led me to spend several weeks researching licensing. I can’t tell you why I did it, but I felt compelled to expand my knowledge. I read articles, bought books, and watched videos all about licensing.

In the next three months, I landed three contracts that utilized my newfound licensing knowledge. I may have dropped out of college, but I made a point of continuously furthering my education—and it paid off.

Many designers transfer full ownership of the work to the client. This is typical with most boilerplate contracts people use. However, these boilerplates underutilize the full power of licensing. By more thoroughly understanding the terms, I was able to craft custom contracts that enabled me to retain the ownership and permit selective usage rights for a fee.

I landed a contract doing work for the city of Las Vegas. When I sent the proposal, my quote included not only compensation for the design work but also specific rights for each design, limited to specific usage cases, and multiplied by the number of months the design was to be used. This resulted in a five-figure quote where I would have previously quoted something much lower due to my limited understanding.

I felt nervous. I sent the proposal anyway. The client didn’t even blink at the number. They told me they would forward it to their payment processing department right away.

When you learn how to speak the language of business with businesspeople, they snap right into business mode. It’s when you sound like you don’t know what you’re doing that companies will take advantage of you. When you’re good at what you do and you back that with confidence and a willingness to adhere to your standards, your terms, and your contract, the right companies will respect you. They expect that kind of confidence and competence from a professional.

In my first year doing freelance hand-lettering work full time and selling my own physical products, I made six figures. It was more than I’d ever made at any job or running any of my previous companies.

I was making great money, charging great rates, working with big names, and shipping physical products every single day all across the world.

But as well as things were going, I was ignoring the elephant in the room.

The Course Creator

Around this time, I received a lot of messages from people asking how to get started with hand lettering. At first, I answered them. One by one, I replied to every single person and shared any tips I knew. Eventually, five people were emailing me a day. I decided that instead of personally answering hundreds of emails, I would make a guide.

I wrote a ten-step introductory lettering guide to answer the most common questions and put it up on my website. Within a year, two hundred thousand people had read the guide! This clearly showed there was greater interest than I realized. The guide was such a massive hit, I knew I needed to produce a course to go more in depth.

I spent the next six months working eighteen hours a day on client work. I worked extremely hard and saved up enough money to quit client work and live off of my savings for six months.

During those six months, I immersed myself in the world of marketing. Once again, I was furthering my own education.

I recognized I had an advantage. Yes, I’d spent nine thousand hours by this point practicing hand lettering, but I also came from a unique perspective. Whereas most artists were teaching people how to draw letters, my background was in business. I knew how to work with clients, price with confidence, and write design and licensing contracts. I was doing this full time.

That’s when it hit me: I would teach people how to make a living as a hand-lettering artist.

What greater disconnect is there than the one between art and business? It’s incredibly rare for artists to have good business sense. It’s equally rare for the people who have a thorough understanding of business to be remarkable artists.

My unique advantage was that I was a master at both. The intersection between art and business was my sweet spot.

I was not clouded by the “starving artist” mentality that plagued the art world. I knew the value of my work and I knew how to work with clients and make money. I needed to share this ability. I needed to help other artists overcome their feelings of the imposter syndrome and their fears of being called a “sellout” by their peers if they ever broke the mold.

Most courses in the hand lettering and art spaces were very cheap, but I had something to share that most artists did not: business experience. I wasn’t just teaching people how to draw letters, I was creating a fifty-lesson master class on how to make a living as a hand-lettering artist. Half of it was teaching the technical drawing skills; the other half was teaching the business knowledge needed to succeed in the real world. The course included everything from pricing to attracting clients, writing contracts, understanding licensing, presenting proposals, and more.

Even though other people were selling cheap art classes on how to draw letters, I came in and successfully priced my course at ten or twenty times higher than the market rate. I was able to sell a multi-hundred-dollar course because my value proposition supported it. I wasn’t just teaching people how to draw; I was teaching them how to make a living as an artist—that’s a huge differentiator.

During the six months I took off from client work to build the course, I got my hands on as many training materials on marketing as I could find. Not a spare moment went by when I was not learning. I read books and articles, watched videos, and listened to audio programs—even while brushing my teeth or taking a shower. For half a year leading up to the launch of my course, I absorbed everything I could about marketing. I learned about pricing, positioning, and copywriting, which helped me promote and market my course in a way that made competition irrelevant.

I spent the first three months alone writing, designing, and illustrating the announcement page. This page was very long with lots of illustrations. It talked about the course as if it were already finished. By the time you read down to the bottom of the page, you were excited and ready to buy. However, when you reached the bottom, the course wasn’t available for purchase. Instead, there was a sign-up form. You could enter your contact information to be notified of the course launch. Half a year later, I had a list of fifteen thousand people interested in the course. Of course, not all of them became customers, but all I needed was 1 or 2 percent of them to convert—and that’s exactly what happened. Several hundred people spent several hundred dollars on the course.

Within three days of launching, I made six figures. The first ten thousand dollars came within thirty minutes of launching the course.

When a hand-lettering artist makes six figures in three days, it gets people’s attention. On the outside, it seemed like this all happened quickly, but people gloss over the part of the story where I showed up every day for two years and didn’t see any results. That’s the part that must be underscored. Success takes showing up every day for years. Nine thousand hours doesn’t happen in a year or two; it happens over a long period of time. Everyone sees the overnight success, but they don’t see the years of work that go into making it happen.

My experience building websites for a living made designing my own lettering website easy. The months I spent reading and learning about marketing enabled me to position the course correctly. Remember the band I was in? My experience with the band contributed to my ability to set up microphones and process my own great-sounding audio. All of the teaching, speaking, video, and illustration experience I had from past projects and jobs all came in handy. For instance, I recorded dozens of training videos for a product we sold at the web firm years back, which gave me a head start when producing my own curriculum. I even composed my own musical intro track for the course. No experience was wasted.

You may be pursuing something right now that ends up not being the thing you do forever. It can seem like you wasted your time, but nothing could be further from the truth. Everything you learn at each stage of your journey will find its way back in one way or another into a future project. Skills, insights, ideas, and perspectives you gain along the way will often resurface in useful ways later in life.

The next year, I decided to add twenty-five more lessons to my hand-lettering course. When I produced the first course, it was just me. I set up the equipment, recorded the video and audio, produced the lessons, and edited everything myself. But by this time, a year later, I had a team—including a dedicated video guy. Our video equipment was also a lot better. In addition to adding 50 percent more material, I also wanted to increase the overall quality, so we reproduced the entire course from scratch.

Once again, I built up buzz, marketed, and launched the new version of the course. This time it made six figures in the first twenty-six hours. I had successfully systematized six-figure course launches.

I could have kept freelancing and making six figures a year with client work. I could have kept making an additional six figures with my course every year. Physical products continued to sell every single day we were shipping items all over the world. I could have kept making a great living for myself these three ways, and there would have been nothing wrong with that. But I’d found a new passion.

The Teacher

While I’d made over half-a-million dollars doing client work and selling products, I found greater joy in helping others. It wasn’t even about the hand lettering for me. I was already making good money for myself and I had a great life, but nothing fulfilled me quite like hearing a student, reader, listener, or a viewer say that I’d changed their life. Receiving a message from someone saying that I’d helped them succeed and made the impossible seem possible gave me a high unlike any other. The ability to change someone’s life, help them get out of a job they hate, and start a business that gives them freedom is one of the greatest joys I’ve experienced.

I knew the principles that contributed to my success in a small niche like hand lettering applied much more broadly than just to artists. I started sharing everything I knew. I shared all of the details of the production, marketing, and launch on my twice-a-week show. I shared my approach to business, and it resonated with people in all kinds of different industries. I kept showing up two times a week and teaching everything I knew. I gave it all away. Before I knew it, the show had millions of downloads.

I found a passion for helping others do whatever they loved and make a living from it. I knew I could grow my lettering business to a million dollars, but to me, that was thinking small. The message I had to share could impact many more people. As much as I enjoyed creating art, the impact of teaching people business was undeniable, and the results were addicting.

I was overlapping again.

Lettering was paying the bills, but I wanted to teach people business. I thought lettering was going to be the thing I did forever. I’d spent nine thousand hours practicing. Wouldn’t it all be a waste if I left that behind? Who would trust a hand-lettering artist trying to teach business? Was the fact that I made six figures in a few days—twice—enough of a track record? What about the millions of downloads? What about all of the success stories and testimonials? Would it all be enough proof that I knew what I was doing?

I had the imposter syndrome.

I thought lettering was going to hold me back. For the longest time, I feared that people would never take me seriously in the business world because I was known as an artist.

Then I realized this was the greatest boon I could have asked for. My success with client work, products, and teaching in the art world was the perfect case study. I found out there are a lot of people trying to teach others how to make money. Most of these people had no track record. The only way they’d ever made their money was by teaching others to make money. This recursion makes most people feel uneasy. What I thought was holding me back from being taken seriously as a businessperson was actually the very thing that gave me credibility: I wasn’t just teaching people how to make money; I had actually done it myself. Before I ever started teaching other people how to make money, I’d put in nearly a decade of work in the trenches.

I branched out to teach other skills I’d learned. I taught a course on copywriting and sales. I taught a course on pricing. I started recording shows on team-building, systems, and delegation. I didn’t start out with hundreds of topics in mind. I had no idea how much I had to share. I just started with a commitment to show up every day and write. I’d record and teach what I knew. As I produced more and more shows, the amount of messages I started getting from people increased. I was having life-changing conversations with people, but they were only happening one-on-one, which meant no one else was able to benefit from the value in these conversations.

“What if I could bring all of these people together?” I wondered.

The Community Organizer

The seanwes community was born. Hundreds of people joined. The membership system was primarily online, but members also started meeting up in their own cities across the world. We hosted some of our own meet-ups in major cities across the country, dozens of members showed up each time, and the conversations were nothing short of incredible. Meet-ups that were supposed to last an hour or two ended up going ten hours. People just didn’t want to leave. They formed lifelong friendships. They experienced breakthroughs in their businesses. At this point, we realized we needed something bigger. Meet-ups were great, but they were limited.

Enter the seanwes conference. We decided to put on our own flagship event. Once a year, people now come from across the world to gather in one physical space to learn and deepen relationships with other business owners.

This is where my vision for seanwes solidified. I didn’t start out from the beginning with some grand vision. Looking back, it’s tempting to rewrite history in a way that sounds good. We like to create perfect stories by tweaking reality. In my case, I was writing daily for years and sharing the journey as I went. There’s a public, written track record. I can’t rewrite history. When I look back on everything, it’s clear that I had no idea where this was all going. Had I not been iterating in public, it would be easy to retell the story and say I set out to build the next great entrepreneurial learning community from the beginning—that I knew seanwes would be the place to go if you wanted to build and grow an audience-driven business.

The truth is I didn’t know. I stumbled my way into it. It doesn’t sound glamorous to say it that way, but I think there is value in telling it like it is. It means you don’t have to have everything all figured out from the beginning. You don’t have to feel paralyzed or afraid of taking the wrong first step. There is no wrong first step. Every step you take is forward progress.

The next thing you pick almost certainly isn’t going to be the thing you do for the rest of your life, and that’s okay.

You’re always overlapping.

The goal of this book is to help you overlap purposefully.