Wild Success in the Gig Economy

My first real exposure to the gig economy was right out of college, where I had followed my rainbow and decided to study photography. I learned to take beautiful photographs, thanks to a very expensive education, but even my professors acknowledged that full-time photography jobs were few and far between. So I decided to work freelance, and was thrilled when I soon got my first gig. But I didn’t get paid for a long time — because I didn’t even realize I needed to submit an invoice.


My school spent 100% of its time teaching me how to take great pictures, and 0% on the business end of it.


My school spent 100% of its time teaching me how to take great pictures, and 0% on the business end of it. I quickly learned that finding success at being a freelance photographer is 10% about taking good pictures, and 90% about business. So I got a full-time job doing something else.


That job was stable and in many ways fulfilling, but it was also terrible for my mental and physical health. I literally broke into stress hives as a toxic boss told me sorting spreadsheets for the department was a good use of my time. I spent years jammed up against a glass ceiling and trapped in golden handcuffs, too scared of the uncertainty that I would face if I ever escaped.


Today, I am the Founder and CEO of two companies, a member of Mensa, and happier than I’ve ever been despite the normal ups and downs of #startuplife. It took me years to leave the “good job” I’d gotten stuck in, but I finally did. I crushed the GMAT, quit my job, rented out my condo, and went back to get my MBA. And in doing so, I truly rediscovered my own self-worth.


My newest brand, SIEX Paths, is about helping others get unstuck, rediscover their self-worth, and find success — wild success — even in the Wild West of today’s gig economy.

We millennials were raised with the expectation that someday, we would work at a full-time job and climb the corporate ladder, just like our baby boomer parents did. Yet when we tried, we found ourselves slipping off the bottom rung of the contingent economy created by the outsourcing binge of the 1990's.


We were told we were spoiled for expecting jobs that would “pay for healthcare,” or “pay us enough to repay our student loans,” or God forbid, “treat us with respect.” We were told this by people who didn’t understand how much the working world was changing, and how little support today’s working people actually get from either their bosses or their government.


It can feel overwhelming when the economic deck seems stacked against us. But that’s also why it’s so important to reclaim our agency, refuse to give in, and to be intentional about how we’re creating our own lives.


To thrive in this new economy, we can’t just keep playing the part of the cog. This new economy forces us to ask ourselves questions like, “What are my priorities?” and “What is my time really worth?” and “How could I restructure my life to be happier?”


Years ago I got to be good friends with a hostess at an Italian restaurant around the corner from my condo. She was hilarious, brilliant, and no-nonsense — but miserable. She was piecing together a handful of part-time, mostly remote administrative assistant jobs to eke out an existence living on a friend’s couch, all while being condescended to by temp agencies that ignored the blatant sexual harassment she’d endured.


Finally, she decided enough was enough. She quit her hostess job and told the administrative gigs she was going to Belize and would be working from there. It was there that she had an epiphany, and her life changed completely.


She realized that, while making the same income she struggled to survive on in the U.S., she could live like the queen she is in tropical paradises all around the world by becoming a digital nomad. She is now the Founder and CEO of The Elevated Nomad, where she demystifies what it’s like to live abroad, and helps other people cut the cord and live their best tropical fantasy lives (or whatever novel geographic features most appeal to you).


As I worked to get funding for my pre-revenue moonshot company, I realized I needed money in the meantime. But it made me sick to my stomach to think of going back to working for someone else. I realized just how much I loved being an entrepreneur — being in charge of my own destiny, not having to constantly acquiesce to the whims of a specific boss — even if things were hard. I refused to shut down my company, but I needed money in the short term.


It was just as I began the dreaded job search that I had an epiphany: I’m great at connecting people to opportunities, and helping them discern and strategize which path to go down. How many friends do I have who are in toxic jobs, who don’t know where they want to go with their careers, who are scraping by on abusive and contingent contract work? How many people do I know who have toyed with the idea of starting a company, but who don’t know where to start or are reluctant to pull the trigger?


And how many of those people have I already helped? A lot.


That’s what I should be doing for a living.


I started doing outreach, and the idea caught fire. Within a week, I had seven clients.


My favorite question to ask my clients is, “What does wild success look like to you?” It’s a question that speaks to what your priorities in life are, and where you hope life will take you. Then we can plan backwards from there.


So…what does wild success look like to you?


Click here to make it happen.


#sharingeconomy #jobs #jobhunting #jobsearch #gigeconomy


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