Deborah Sweeney
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MyCorporation.com CEO

Quitting a corporate job, especially if you haven’t done it before, can be jarring (to say the least). It’s one thing to fantasize about leaving a cubicle position, and quite another to actually go through with the decision. You have to be all in if you choose to leave, and understand that life will not be the same as it was before. Adventure — and the chance to pursue your dreams — awaits on the other side. But so does the struggle of navigating life without a steady paycheck, insurance benefits, and that little voice inside your head asking, “Did I make the right decision?”


Leaving the steady corporate world for the narrow and windy entrepreneurial route isn’t easy, but it can be done. Studies even show that by the year 2020, contingent workers will exceed 40% of the workforce, making traditional jobs harder to find. I had a real talk session with four professional women about the eye-opening lessons they learned after leaving their corporate jobs. Let’s see how this decision impacted their lives for the better.


1. Benefits are arbitrary.

Before Ashley Copeland became a podcast host, she spent a year and a half working for Morgan Stanley. It was the ultimate in corporate jobs: an established brand name, solid pay, and great benefits. However, Copeland soon realized that corporate benefits tend to be arbitrary. 


“Many companies entice new talent by discussing benefits like PTO, company matches for retirement plans, and health plans,” she explains, “But, many employees don’t understand retirement contribution schedules or use their vacation leave.”


The experience taught her a valuable lesson: she wanted to establish benefits that suited her needs. Copeland has since become the host for financial podcast Stacks and the City and has created opportunities for her own paid leave, retirement plans and health insurance.


2. Entrepreneurship isn’t as sexy as it seems.

When Jessica Lawlor was 27, she quit a six-year career in corporate public relations. She wanted to pursue her side hustle (in content management and PR), teach yoga and blog full-time. The idea of having a career cobbled out of her passions felt pretty sexy.


Lawlor found herself getting caught up in the daydream of being an entrepreneur. No boss, working when and where you want, and living your vision. 


“It was easy to dream about the freedom of entrepreneurship while I was side hustling and commuting to and from work each day.” Lawlor admits.


However, the reality was that Lawlor’s early days as an entrepreneur weren’t sexy at all. In fact, they kind of stunk. She found herself struggling to figure out the financial details of running a business, experiencing loneliness and feeling lazy without a set schedule.


Despite the initial shock, Lawlor stayed committed to being an entrepreneur. She’s now the Founder and CEO of Jessica Lawlor & Company and wouldn’t take her decision back for anything. 


“After tasting the freedom of running a business, I don’t see myself returning to the corporate world," she explained.


3. You’ll get over it.

When Talya Miron-Shatz, PhD was 37, she made the painful decision to leave her corporate job behind. Miron-Shatz is now 52 and the CEO of Buddy&Soul, a personal development startup.


She recalls that waking up the first morning after 11 years of working felt like being in a frightening void. By 9 AM, however, Miron-Shatz was in her first yoga class ever. As time progressed, she found that so much of the corporate world she was used to, like company gossip, seemed vacuous. Her passions and dreams were what really mattered. The world, as Miron-Shatz says, is truly your oyster.


4. Sometimes there is no *right* time to leave a corporate job.

Natalie Athanasiadis, Owner and Head of Growth at Ormi Media, was booted out of her corporate job due to the company closing abruptly. Rather than return to another corporate role, she decided to launch her dream agency. 


Five weeks later, Athanasiadis was running her own business. It was making six figures and growing! Sure, it might not have happened at the “right time,” but what constitutes as great timing anyway? 


“Sometimes there is no right time,” Athanasiadis says, “If you work consistently, you can achieve your goals. Just go for it!”


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