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If you read Quitter , this is not surprising to you. I had made a backward career move—because I wrecked my job at Home Depot—and ended up working at After Hours. Though at first blush that sounds like a ladies dance establishment, I assure you it was not, though given my green belt in Kenpo I could probably be a bouncer if I had the time.
    After Hours was actually a formalwear company that specialized in rental tuxedos. If you’re playing along at home, I went from being one of the copy chiefs at a multibillion-dollar national brand to writing product copy trying to convince teenagers to rent my pants for the prom. Like a boss.
    During my less-than-lustrous career at After Hours, I decided to start an ad agency. I’d worked at a small agency before and thought, How hard can it be? So I started one with a guy I knew from church. We got a whole bunch of business cards printed with our logo that kind of looked like the ThunderCats, registered our business, and went looking for a client.
    We had huge aspirations. We were going to be a massive agency with hundreds of clients, a dream mirrored by our need to order thousands of business cards. Next step? Get someone to pay us to do whatever it is we thought we were capable of doing.
    Our first client was a church in Charlotte, North Carolina. My dad’s a pastor, so I understood the mechanics of that world. We were able to convince an incredibly kind woman at the church that our new company could build them a top-notch website. We put together an impressive proposal, and we agreed to build the site for around $30,000.
    The church, showing wisdom, didn’t pay us the entire amount up-front and only gave us an initial payment of about $12,000.
    Then we got to work. I built a crazy site map, trying to make sense of the thousands of disconnected web pages this church had. The youth department had built their own site; the senior adults had their own section; everyone who had access to a computer had seemingly added a page to this tangled mess. I did my best to make sense of it and then turned over the project to my partner.
    That last paragraph makes me sound like a good guy.
    The truth is, I bailed on the project. I walked away and left him completely in the lurch. It was a train wreck, and I thought that maybe my partner could magically make sense of it.
    Months into the project, a few realities about my present circumstances started to catch up with me: I didn’t know how to run a business. I had never built a website before. Neither my partner nor I had any web developing skills.
    After many sweaty nights, we decided to pull the plug and refund the church their remaining money. (Some had been spent on a third-party design firm we had hired to fix reality number 3.)
    In the meantime, my partner moved with his family to another state, and I waited patiently for the whole situation to fade into the sunset of my life. But like a zombie who continues to crawl after you without legs, that thing was not going away easily.
    The church had not received their refund check. My partner had sole control of the money. I called him over and over again and didn’t get a response. I started to hate his voicemail greeting, which played John Mayer’s song “Waiting on the World to Change.” I wanted to punch John Mayer in the face.
    Finally I got through to him and he agreed to overnight the money.
    Two days later, I got a voicemail while at my day job: “Hi Jon, this is Sara! Hope you’re having a good day. The check you sent us bounced. Please give me a call back.”
    Cue vomit.
    The check we had sent—to the church my grandmother had attended for thirty years—bounced.
    The money was gone. The account was empty. My partner had spent it.
    How had this happened? It’s painfully simple. I broke my own rule: I wasn’t brutally realistic about my present and was wildly unrealistic about my future.
    I got the second part right. I crushed that part! I had big, crazy, unrealistic dreams