Yesterday, I hosted an impromptu four-hour lunch for two of my childhood girlfriends.  For lack of better phraseology, the three of us met in utero.  To explain: before we were born our parents lived in a Melrose Place-esque complex where all three couples got pregnant for the first time at the same time.  I was born in October, then came Beth in November, followed by Chelsea in March.  Over the course of three decades, we’ve grown apart and come back together more times than anyone can remember.  No matter what occurred in our lives independently, we’ve turned to one another united in a way that only those who’ve known each other their entire lives can.

While we prepped lunch (an autumnal feast of Fig and Fried Goat Cheese Salad, Lobster Pot Pie, and Brown Sugar Bourbon Baked Apples) we realized that we hadn’t been together, just the three of us, in nearly a dozen years.  As Chelsea assisted in the kitchen and Beth over-poured Sauvignon Blanc, the initial awkwardness gave way to intimate discussions of what we’ve done during the time apart – mistakes (i.e. one night stands), failures (i.e. careers), accomplishments (i.e. advanced degrees), desires (i.e. more one night stands). 

After a second glass of Sauvignon Blanc, we indulged in the childish query, “what do you want to be when you grow up?”  All of the clichéd genres to pick from were discussed – the ruthless corporate badass, the crunchy granola altruist, the genius scientist recluse, the sexy tortured artist, the beautiful Stepford Wife.   And you have to choose, because dark swirling chaos can’t co-exist with the white picket fence, right?  Right…??

What we took away from the day (other than our collective existential crises) is that Beth and Chelsea both recently discovered their passions, and I took a leap to follow mine.  The question that naturally followed was how to go about turning their passions into careers.

It seems appropriate that I’m writing this a year after leaving my lucrative legal career to turn Table + Teaspoon from a blog into a company.  (Coincidentally, it’s also T&T’s fifth birthday this month!!)  Though I won’t feign to be an expert in the nuances of start-up life, I do know a few things about creating a job based on what motivates you to get out of bed in the morning.  If you’re daydreaming about taking a similar risk, I hope that my experience will shed some light on the reality of going out on your own and motivate you to embrace the adventure.

Here’s the thing about pursuing your passion: one moment you are successful, confident, and impenetrable – the next you’re struggling, confused, and afraid.  Starting a business isn’t sexy.  It’s effectively the professional equivalent of bipolar disorder.  It’s a stay in bed all day depressed or work 48-hours straight to meet a deadline, anxiety-inducing, I’m the most amazing person in the world - wait what the fuck am I thinking, maybe I should just buy a one-way ticket to Paris and disappear into a Parliament Light-smoke-haze because I ruined my life kind of madness. 

Do I wish that I was still sitting in my FiDi office with a secretary and glittering bay view?  Sure.  Do I miss shopping at lunchtime for the perfect little black Tom Ford dress to go with my edgy-but-still-pretentious Valentino spiked-heels in order to validate my 14-hour work days?  Sometimes (but not as often as you’d think).  Do I still want to use my legal training?  Yep, but that’s why I volunteer for people who can’t afford representation. 

Do I regret my decision to recklessly abandon all of this security?  Emphatically, no.  Despite the struggles I’ve encountered, I won’t allow myself to arrive at death’s door wishing that I’d done what I wanted to with my life.  Because that’s the thing, this is your life.

Here’s the other thing.  There are a great deal of logistics to consider before taking the plunge into the world of a deranged passion pursuant.  If you have time to go to culinary school, medical school, carpentry school, fashion school, astronaut school – whatever drives you – great.  But the truth is, by the time you realize what you actually want to do with your life, it’s often too late to subscribe to the traditional method of training in that particular field.  This doesn’t mean that you have to give up, it means that you have to adapt quickly.  Beyond the obvious suggestion to read everything you can get your hands on – books, magazines, Wikipedia – my advice is to jump right in and get your hands dirty.

Once I figured out what I wanted to do (something that is continually evolving), I started doing it.  I spent three years hosting meticulously-decorated multiple-course dinner parties for twelve friends every ten days, until I was confident that my skill-set was on a professional level.  Lacking that option for interior design and event planning, I offered my services at cost or insanely reduced rates (think $1/hr) while I was learning the business.

I didn’t rely solely on trial-and-error, I also leaned on my friends for guidance.  You’ll be surprised by how many people will feel inspired by your passion and want to share their knowledge with you.  Want to be a professional photographer?  Ask your photographer friends how they got started – they will likely overshare and give you a million tips.  Don’t have any photographer friends?  Go hang out at your local camera store and make nice with the guys behind the counter.  Don’t know how to price your services?  Send out ten emails to the top people in your industry – you’ll get at least a couple useful replies.

The rest is up to you.  Decide what your passion is worth, write it down on a piece of paper and stick it in your wallet.  Pull it out when you need a quick reminder that this is what makes you happy.  Figure out a plan, dip into your savings (or find financing), tell people what you want to do and ask for help, make a website (Wix is INCREDIBLE), make a logo (Hipster Logo Generator is a free lifesaver), and shoot for the stars.  Worst case, you go back to your stable job with the knowledge that you didn’t hold yourself back from your dreams.  Best case, Martha Stewart Empire!!  Okay, maybe that’s just me – but you get the gist ;)

xx tt