Learning to Swim (or “I Quit”)

I assume all of you have, by now, guessed what the "big life change" that I have been writing about since January is. It hasn't really been a secret for a while, but I wanted to at least keep it semi-secret until I had performed all of my research, due diligence, and prep-work, in case I had to make any changes to my plan. After a couple of delays for several reasons, I can finally officially reveal what this "big change" is.

On Monday, I quit my very comfortable job at what is, by all accounts, an excellent law firm to become an entrepreneur/writer. "Holy shit, are you nuts?" Well, Mom and Dad, maybe I am. I thought that I would go through my thought processes on here, not really to "make the case" for my decision, but rather to try to provide some guidance for those that are attempting to do the same.

Ever since my Thanksgiving Moment of Clarity ("TMOC"), I have been thinking about what kind of life I want to lead. I've always had an entrepreneurial itch, and through college and law school, I would bounce ideas off of various classmates. Some of these ideas were total flops, but I thought at least some of them were good enough to be put into practice. Unfortunately, I kept putting the implementation of these ideas off. "You don't have enough money." "What if it fails?" "It's a stupid idea." "You'd have to give up your 'real' job—that wouldn't be practical." These thoughts were reinforced by some family members, friends, and colleagues. There were plenty of other family members and friends, though, that said to go for it—told me to follow my dreams, make them a reality.

The only problem was I was stupid and didn't know how. I kept putting these ideas off, thinking that "some day" I'd get around to them. I didn't realize the vast potential of the internet, where you can basically look up steps to take toward becoming almost anything you want to be. I was also very lazy at the time. I was immature, preferring to spend nights drinking, carousing, or just watching movies and TV instead of working toward what I wanted. So, I continued putting off the realization of these ideas, thinking that they would still be there down the road.

Then, a crazy thing happened—some of these ideas started popping up, run by other people. Take this example. Or this one. As I saw the success these ideas enjoyed, I grew angry at myself for not having the balls to have at least tried to make these ideas a reality. Sure, there may have been some set-backs, and there's no guarantee that I would've run these businesses as well as the actual proprietors, but there was always the sense that "I'd rather be doing what they're doing"—building something from the ground up.

The firm that I have worked for these past two-and-a-half years has been great. The people are generally fantastic, amazing lawyers, who are legitimately the best people in the city at what they do. The only problem was, as a profession, the law generally doesn't allow me to pursue my true goals and dreams. I want to build businesses. I want to develop characters and bring the stories in my head to life. I want to write blogs that are not only (hopefully) informative, but also that inspire others to action. I want to bring my ideas to the world, and let the marketplace sort out what's good from what's shit. If I fail, I'll always have my legal training and two-and-a-half years of experience at a top firm in town on my resume, and countless connections in the legal world.

My firm, like many others, is not keen on having attorneys that start side-businesses or serve on the boards of even small corporations, and rightfully so—if I was running a premier service corporation, I would want any attorney to be available to service clients on a moment's notice without the distraction of a side-business detracting from their efforts. Let's face it: these firms pay their lawyers very handsomely to ensure that the firm will have the full attention of its associates at all times, no matter the day, hour, or project. The flip-side of that is that, like many people of my generation, I value my time to pursue my projects more than money. Even if it's a lot of money—and it is. I still just value my time more.

So what's next for me? This blog, which I hope to ratchet up to posting five times per week. Another blog, which will be released shortly (probably the end of May). A couple of e-commerce businesses, which may take a little longer to get off the ground, but I will be sure to tell you when they do. A podcast that I've been working on with a couple of buddies will be released shortly. A three-week trip to Australia, to recharge my batteries, surf, and get inspiration and a new perspective on life. I'm trying to sell a book, and get my CSW certification to cement my status as a wine professional. And who knows, maybe I'll write a novel or two on top of all of that. It sounds like a lot, and I'll admit, it is, but for the first time in my life, I feel like I'm doing what I want to do. There is a power and peace that comes with this feeling that is indescribable—like I have almost been reborn.

I'm sure there will be plenty of detractors out there, "You're crazy, I would kill for your job, you have no chance, you're an idiot, you'll come crawling back to biglaw, you're a wash-out, you're a failure." I kindly refer these individuals to Rule Number Four. I've set aside enough money to make a reasonable go of it for a while as I pursue my businesses and ideas. I've heavily researched my endeavors, and continue to do so. I've read books and websites on countless topics from marketing to search engine optimization to sales, and I've tried to identify key areas where similar companies make missteps along the way. I've tried to account for pretty much every "hidden" expense, though there are obviously some I have overlooked, though I have budgeted for those, as well. In short, I've tried to accumulate as much information as possible to ensure that I succeed.

I liken it to learning to swim. You can read books like "The Breaststroke in Five Easy Steps," (picked up initially for…other reasons) "How Wet is Water?" and "Noseplugs: The New Paradigm." You can reach out to champion swimmers like Michael Phelps and Mark Spitz, and get their advice on what you should do. You can dip your toe into the water to try to get a "feel" for what it's like. But at some point, you have to jump in the goddamned pool. I've researched and discussed these moves extensively, and dipped my toe in the water. I brought myself to the edge of the dock, hoping that the information I've learned would be useful, and tried for weeks to work up the courage to take the plunge.

Now, I have jumped. It's scary, but exhilarating. We'll see if I can swim. I think I can, but you never know until you try.

And I feel fucking fantastic.

Questions? Comments? Think I'm an idiot/completely inspired? E-mail me at djssuperblog@gmail.com. Follow me on twitter @djgelner. Friend me on facebook here.

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