Before You Become a Freelancer, Binge-Watch These Shows

In 2009, my body informed me that I was no longer fit to be a programmer, through a mutinous uprising of my appendix.

I was fired shortly after that from a sweet programming gig. Staying focused on semicolon placement (and, for that matter, wearing pants) after the surgery was impossible. At the time, I chalked it up to something in the healing process going awry, but what was happening was a significant shift in my passions. I’d nearly died, and it was time for a change – even if I didn’t realize it yet.

Enthralled for months by Leo Laporte’s podcasts, This Week in Tech and Social Media Today, I devoured everything I could on marketing. I spent a lot of my off-time on Twitter, Mashable, and Digg reading articles on social media and marketing. After exploring the marketing world for a long while, and with no other professional ties, I decided to jump in and start my own company.

Like anything worth doing, it wasn’t (and still isn’t) easy. Picking up new clients was a slow, arduous process. Figuring out the ins-and-outs of contract negotiation, project scoping, client management, taking sick days, and learning all of the other trappings of entrepreneurship was and is an ongoing process.

Tough times tried the depths of my conviction and made me question what I was doing and why – my wife liked to “joke” that every six months she’d brace for my “rebrand and retool” mood.

Fortunately, I have been aided by some of the sharpest minds in business along the way – even though some of those minds are fictional. Certain lessons were within my grasp before I started if I’d only known where to look. I highly recommend, if you are itching to become an entrepreneur or freelancer, that you binge-watch the following series before you take the leap:

Firefly – the penultimate freelancer binge-watch and entirely possible to do within a day (there are only 13 episodes). A space western about a ship and crew doing their best to survive and profit in the not-to-distant future with almost all of the odds stacked against them. Beyond Joss Whedon’s masterful writing, you’ll learn a thing or two about how to negotiate and how to set expectations while dealing with less-than-reputable characters.

Boston Legal – watch this specifically for two characters: James Spader’s Alan Shore and William Shatner’s Denny Crane. In Alan Shore’s speeches, you will find the veracity, depth of commitment, and speedwork you’ll need to negotiate contracts, handle client change requests on the fly, and even defend your work (even if you’re very good, the need will arise). In Denny Crane, you’ll find the devil-may-care attitude you’ll need to shake off complaints, failed projects, and mismatched expectations. In fact, you could just troll YouTube for Alan Shore speeches and revel in his meticulousness to rip emotional points from the ether.

Star Trek – literally any Trek will do; when you’re in a pinch, Deep Space Nine and Avery Brooks as Sisko are great to watch – especially the episode In The Pale Moonlight, when you have tough ethical questions to wrestle. Enterprise can help you find your fire, particularly the 2nd and 3rd seasons when the chips are down, Captain Archer and crew are fighting for survival. Captain Janeway’s strategic juggling in the Star Trek Voyager episode Counterpoint and her empathy in dealing with both The Doctor and Seven of Nine throughout the series are fantastic learning tools.

30 Rock – Alec Baldwin’s Jack Donaghy for confidence and Tina Fey’s Liz Lemon for her keep-all-the-plates-spinning attitude.

The West Wing – not quite on par with Alan Shore, some very fine speeches and political strategy combine with rapid-fire wit and masterful handling of utter disaster to make you want to be a better human being. From “Let Bartlet Be Bartlet” onward, these characters epitomize conviction.

Finally, and this is my go-to binge watch: Parks and Recreation. Entrepreneurs can’t accomplish anything alone. Having a great team behind (or alongside) you who believe in you, support you, and want you to succeed is the best resource you could ever ask for. Also: being able to identify the Leslie Knopes in your life is a critical skill.

Do you have a business binge-watch favorite? If so, post it in the comments!