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You’re not really prepared for the decision when it hits you – you just know that the road you were traveling down had some unexpected curves and detours ahead that don’t lead to the place you had intended to go. You’ve arrived at a crossroads and the light is on the verge of turning green any minute now. You’re not panicked, rather cool and cautious about the next turn of the wheel. You remember someone calling you fearless recently and you’re bolstered by that endorsement.

You take some time (read: drink a lot of scotch), get introspective (read: call your mentors who luckily take late night phone calls) and consider your next move (read: don’t sleep.)

You remember the question that was asked of you months ago in a press interview, the one question you didn’t have a prepared set of talking points for. Sneaky journalists.

“If you could do any job in the world, what would it be?”

You remember your off-the-cuff but candid answer:

Honestly? Some kind of cross between the Barefoot Contessa and Anthony Bourdain.

You remember the face palm you did in your sunny office overlooking Atlantic Ave. So much for media preparedness. The journalist laughed and thankfully did not include this in the resulting piece about you being a millennial CMO and female entrepreneur. (You later read the piece and feel like a baller.)

Back in the safety of being off-the-record, you wonder if these two personalities could ever combine. Ina Garten and her fabulous, discerning, casually exceptional presence; Anthony Bourdain and his give-no-fucks, capricious gallantry. You park the thought and jump on your next call to give another demo to another potential customer. Back to the hustle. You love it.

What was plan B, again?

When I made the decision to leave my startup and strike out on my own to work, entirely for myself as a marketer-for-hire, my biggest fear was not finding work or making enough money. It was becoming a cliché. When you’re marketing to marketers, it comes with a lot of visibility in the process. When you leave, it needs to be well-thought, deliberate, and smart.

When the best-laid plans go awry, we often find ourselves in unexpected places, for which we did not have a backup plan. When one job is no longer viable, typically you find the next similar opportunity. You seek a salary boost, a short commute, a positive workplace, growth potential, and a title that matches your career trajectory.

But when you’ve spent years working with startups, the most recent 18 months as an entrepreneur and one-woman marketing band, there is truly no clear next step. That road you were on looks more like an island, one that is drifting slowly further from land. The best word I have found to describe the feeling is untethered.

You’ll go on a few real interviews, you’ll explore becoming the Director of this, or the VP of that. Everything feels too expected, too neat.

You feel inexplicably unfaithful to something else that’s now part of you.

You’ve been bitten.

This is that entrepreneurship bug they talk about. It’s the thrill of doing something your way, of being your own boss.

That untethered feeling? That’s not aimless drifting. That’s freedom.

During one of your scotch-or-champagne-fueled life planning dates with one of your very smart friends (good on you for surrounding yourself with brilliant people), you examine your career to-date. You realize it’s been filled by roles founded in risk, uncertainty, a lack of structure and predicated on self-direction.

Hell, you’ve been a downright anarchist (for good) at each of them.

Not one, not two, but several of your smart friends have the same suggestion. Go on your own for a bit. Do what you do, your way, with projects of your choosing and with people you want to work with. Consult.

You initially think they’re nuts.

You know some amazing consultants and they have been in this business far longer than you (I’m looking at you Samantha Stone, Denice Sakakeeny, Stephanie Tilton, Ardath Albee, Doug Fox, Kim Donlan, Carlos Hidalgo.) You rely on them often for guidance and advice. Beyond these exceptional professionals, the term “consultant” comes with a stigma. Let’s be honest, there’s no barrier to entry.

But you remember that bug – what is that thing that urged you away from jumping into a full time “real job” again? It could be gut. Intuition. Purpose. Fate?

(Question mark around the existence of fate and your reliance on it for practical career decisions. Blog post for another day.)

You make the decision one day when suddenly, unprovoked, two real projects come your way within an hour. As if the universe itself had conspired to push your cautious ass into this bold new direction by making a couple of stars align. Before, you had to say no to these side hustles (unless they were really fun, like producing that gay comedy show in Miami. Sometimes my life doesn’t feel real.) Now, they were what you needed to make the call.

You set up some ground rules:

  • Work on projects you can truly deliver exceptionally.
  • Help the people you trust and respect, for products you stand behind.
  • Take time to take care of yourself, your family, and plan a kickass upcoming wedding.
  • Read, learn, and invest in your professional development with a schedule that is truly yours to make.
  • Have more fun than a “real job” should ever be.
  • Be somewhere between the Barefoot Contessa and Anthony Bourdain.

You go for it, emboldened with a sense that this is not resigning. This is not the easy route. This is not giving up. This is your next business as an entrepreneur. You’re responsible for its success, or failure. You put out the notice, start a newsletter, and receive a wonderful amount of support and stimulating new projects.

Only once or twice do you ask “what the F--- did I just do?”

Untethered freedom feels a bit like flying.

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