Should You Quit Your Job To Work For Yourself?

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You've probably thought about quitting your job at least once or twice in the past few years (if not, congrats — we love our jobs, but we're all a little jealous). And, in those moments, if you're like us, perhaps you've thought to yourself, "Wouldn't it be nice if I were the boss?"
Seriously, though, what if you called the shots and you were the one who got all the credit for all the amazing stuff you worked on every day? What if the by-product of your daily efforts was something that belonged entirely to you? Pretty tempting, right?
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And, also, pretty scary. Because the flip side of owning all of the success is taking the fall for all the failures. It's not having a real safety net if the business doesn't turn a profit (no severance package, nobody to pay into your benefits and life insurance — the list goes on).
Yeah, the rift between the pros and cons here is pretty wide. So, we chatted with a former magazine editor who recently took the leap into entrepreneur-dom. Rachel Mount Hofstetter just wrote Cooking Up a Business , a book rounding up the very best wisdom from the women behind all of our favorite foodie start-ups. And, she says, "By the time I turned in my book manuscript, I was so inspired that I then left my job and struck out to work for myself, launching my custom mini-mag company, Guesterly. You could say I’m a food editor gone rogue — and I’m an enthusiastic believer that every woman should work for herself at some time in her life."
It's tough to doubt that kind of enthusiasm. Ahead, her list of reasons why this might be the most appealing risk you'll ever take.
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1. You call the shots — and for better or worse, there’s nothing else like it.
"All the leadership training seminars in the world can't properly prepare you for the first 90 days spent working for yourself — when you’re in charge and you and your team rise and fall based on your choices. When I was a magazine editor, there was always someone to approve my story ideas and make the decision as to where we would allocate resources. After I edited a writer, someone else always had a final edit and would sign off on (and take ultimate responsibility for) everything that went to print. Now, I take ultimate responsibility — which is fun when things turn out great and gut-wrenching when a typo slips through or the printer messes up. But, like any muscle, your ability to call the shots gets stronger — and then it makes you feel stronger, calmer, and more powerful."
2 of 10
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2. You’re welcomed with open arms into an exclusive club.
"When my partner and I launched Guesterly, one of the things that surprised me most was how immediately — seriously, immediately — we were taken under the wing and welcomed as part of the entrepreneurial community. Another woman might be on her fifth start-up and a billionaire, but if you’re putting it all on the line and working for yourself, too, you’re essentially on an even playing field. From dinner parties to strategy sessions and introductions to simply saying, 'Yes, this is normal, and now you can do X, Y, Z,' the people you're surrounded by help and encourage you in the most tremendous way."
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3 of 10
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3. You become a better employee.
"It turns out that when you have an intrinsic understanding of what makes a business work, you become much more cognizant of how to be the ideal employee. Plus, each day running your own thing makes you infinitely more valuable as a future hire: You’re not just saying you can run a team, create a product, or forge partnerships — you’re proving it."
4 of 10
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4. You get to feel like a kid again, and suddenly, everything is amazing!
"True story. You start to appreciate amazing customer service, amazing websites, and amazing branding in a whole new way when you're trying to create all of that for yourself. The world becomes awe-inspiring in so many new ways. As soon as you understand how hard it is to get something right, you become incredibly impressed with everyone who has come before you and done something well. Remember what the most invigorating, interesting college class felt like — the one that taught you how much you loved learning? That’s what every day of working for yourself is like. Yes, this is a slightly rose-colored version of the story, but some days, life really does feel this magical."
5 of 10
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5. You learn — really learn — how to lead, inspire, and direct other people.
"When you manage people at a company, there’s always someone or something else to blame. But, when you're on your own, there are no ancient policies, incompetent hiring managers, or bad decision makers at the top to blame for inefficiencies. You learn — fast — how to lead other people in a meaningful way. Along the way, you learn how to manage your own time and energy better, too."
6 of 10
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6. You get good at saying no.
"With only so much bandwidth and resources and a multitude of new responsibilities, events, people, and opportunities, you suddenly have to say NO to a lot more when it’s your butt or your budget on the line. Maybe you’re actually saying no, maybe you’re just choosy about the parties you attend, or maybe you prioritize some projects and let others fall by the wayside until later. But, no matter, you realize you can't smoothly negotiate everything without making some tough decisions. And, that ability to say no translates into clearer focus in all the things that you do — and a reminder of how badass you are, too."
7 of 10
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7. You come up with big brilliant ideas and tiny next-step ideas.
"You become an idea-generating machine because there’s no one around to shoot your ideas down. You’re creating something brand new — no more 'we’ve always done it this way, so we’ll continue to do it this way.'”
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8 of 10
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8. You get to change the playing field for other women.
"While women are almost as likely as men to start their own business (eight women for every 10 men), that’s a rapid increase over the past 10 years. Each women who strikes out for herself helps to create more examples and more reasons for other women to do the same. Pretty powerful stuff. Plus, once you've struck out for yourself, you get to mentor other women (and men) and pay it forward."
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9. Nothing has ever felt this good.
"Every day, every decision, every action, every meeting, and every conversation moves your company and your brand forward — and you get to control that direction and momentum. You get to solve the problems you care about, whether that’s getting GMOs out of your food supply, creating a community at weddings, coming up with a genius way to unlock doors with your iPhone, or designing or writing or strategizing something you care about, deep down in your core. And, when it works out — in those brief moments when everything goes right — you’ll feel a million times better than you ever did when succeeding for someone else."
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10. And, yeah, you get to wear PJs to work — once in a while!
"I'll admit it: On a sleety, cold December morning, there’s nothing like grabbing a cup of coffee, settling in at your desk, and knowing that today, you’re cozy inside. This scenario is probably taking place at 7 a.m., and you’ll work nonstop until 9 p.m., but it's all so, so much better with plaid flannels on. And, as a bonus, you’ll probably enjoy dressing up and putting on heels even more the next time you do it."


Rachel Mount Hofstetter is the author of the new, go-to guide to food entrepreneurship Cooking Up a Business. The former food editor at O, The Oprah Magazine and Reader’s Digest was so inspired by the entrepreneurs she wrote about that she started her own company, Guesterly, which creates custom magazines.
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