Three weeks, 5 interviews, and one very bad hangover later, the search for the “perfect fit” continues…

It was just a couple of months ago when I decided it was time to leave the corporate world (once again) to embark on giving full attention to a business I spent the last three years building.

Long story short – the prospective contract that was grand enough to convince me to turn in resignation, fell through just as my position became replaced.

Despite the preparations made to leave corporate, when the other big job fell through, I stumbled into a big hole of self doubt.

Arriving in the Land of Oz

After a decade of work in executive support and a slew of side projects in my industry (digital marketing),  you would think I’d be excited to finally be free again and ready to take on the world. Instead, it feels as though I fell into a bad dream and awoke in the land of Oz. With ruby-red’s strapped to my feet and all the magic to take me where I’d like – I’m still allured to an obscure search for the “Emerald City” of a corporate career.

Those of us in our mid 20’s (and ages beyond) are searching for passion to lead our careers. And why shouldn’t we be? Culture tells us that we can have, become, and create anything our hearts desire. With such promise, paired with the myriad of tools at our disposal, we really do have the opportunity to create the fantastic vocations we imagine.

But many of us fall prey to “adulting syndrome” – a condition often met with the precarious obsession of paying rent, saving for retirement, and buying a home we can barely afford.

Somehow, the quiet echoes of a time when we needed a college education and a steady job to be successful seem to sound over our awareness of what we actually want to be doing with our lives (and are furthermore, completely capable of.)

Truth about the Yellow-Brick Road

Then, there are the few who have chosen a different path – paths not paved with the promise of “a place where every one gets along and there are no troubles” – but a road that promises every kind of hardship a soul can endure.

Knowing the journey of these kinds of lives – those like Tim Ferris, Marie Farleo, Marc Zuckerburg, and Seth Godin – it’s obvious that the “yellow-brick-road” of entreprenuership is often laid with everything from depression, to broken partnerships, financial troubles, and certainly no magical slippers to click when the comfort of Kansas seems more appealing.

While the struggles of each entrepreneur vary, there are common strengths they posses – strengths such as curiosity to continually create solutions to hard problems, the gumption to risk failing at those attempts, and most importantly, the optimism to turn such challenges into opportunity.

Daring to Defy Gravity

It seems those who “defy gravity” of the normal career also persevere through discouraging voices of of silly-scarecrows and cowardly-lions all while holding fast to their understanding that the illusion of Oz (aka the “safe” career with it’s proposed security) isn’t worth sacrificing the passions they hope to live out.

As I reflect on my own path and the lives that have made such awesome impact on the world, I’m inspired to push through the discomfort of an uncertain future and acknowledging that the best fit is likely one tailored by my own two hands.

Maybe our search for those magical slippers help us define our style. But when we can’t seem to find the perfect fit, maybe that’s our chance to design our own damn shoe.

With Joy,


*This post is dedicated to all my courageous sisters out there designing their own ‘shoes’ – Emily, Seda, Leighanne, Janna, Erica, Ryan Mae, Jen, Anne, Hugette, Gennah, Kim-Erin, Hillary, and many others…thank you for inspiring me with your lives to pursue the more difficult (and more rewarding) road of entrepreneurship.