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Thinking About Leaving Your Job? Here’s How Seven Entrepreneurs Decided to Take the Leap

From inspiring books to unsupportive bosses, here’s what made seven women leave their day jobs to go it alone.

By Madeleine Kim

No matter how much you like your job, you’ve probably fantasized at some point about quitting your nine-to-five to start a business of your own. Flexible hours, being your own boss, building a company that reflects your values—it’s enticing! But at the same time, it can be scary to give up a steady paycheck and enter the unknown. 

So how do you know if becoming an entrepreneur is the right move for you? The decision-making process looks different for everyone, so we asked successful entrepreneurs to share the one thing that finally made them decide to take the leap. From inspiring books to unsupportive bosses, here’s what made seven women quit their day jobs to go it alone.

Beth Schubert, Co-Founder and CEO of Own The Grill

“It was a book that led me to take the plunge and start my own company. Previously, I’d worked in journalism, social media management, and PR, and it was difficult to let go of steady work and a regular paycheck. But upon a friend’s recommendation, I read A Little Life by Hanya Yanagihara, and it utterly changed my life.

Be warned: This book really isn’t for the faint of heart. But I do believe that it’s one of the best, most impactful pieces of modern literature out there. So much is stolen from the book’s characters, and I didn’t want to let any more of my time be stolen by a career where I wasn’t happy anymore. I am so glad that Yanagihara’s prose finally inspired me to make a change. We have such a finite amount of time here, and although it’s cliché, we really do have to make the most of it.”

Kira Karmazin, Founder and CEO of KiraGrace Inc.

“I lean on Suzy Welch’s 10-10-10 decision-making rule: I ask myself, How will I feel about this decision in 10 minutes? 10 months? 10 years? This framework helps to put the decision into the context of your entire life. I used this method to make the decision to leave my well paying corporate role and begin my life as an entrepreneur. I wanted more flexibility in my life so I could be a more present parent (I was single parenting and traveling 70% of the time). But the tradeoffs were enormous: I would give up relative financial stability for a riskier, possibly lower income. Or perhaps, if I failed, there would be no income.  

  • In 10 minutes: The decision felt good. I wanted more time with my daughter and more time back in my life.
  • In 10 months: Things could get dicey. Will the business succeed or fail? Do I have the cash reserves to cover this period of transition?
  • In 10 years: It became crystal clear. The most important thing in my life was to be present for my daughter during the next ten years. You never get this time back, and the corporate work I was doing did not reconcile with my goals as a parent. I was sure I would get by financially, either by successfully creating this business or by contracting my skills in another way. I felt confident enough in myself that I could support my family—and with ten years of hindsight, my daughter, Grace, would be all that mattered. 

I announced my resignation, gave the company a six-month transition time, moved home to California, and started this new life. That was ten years ago, and it was the best decision I ever made.”

Lara Hartog, Writer and Editor at The Best Travel Gifts

“As a very indecisive person, I often have trouble making even the smallest of decisions, like whether to have coffee or tea. So you can only imagine my struggle when I was trying to decide whether I should quit my full-time job and start my own business.

But here is one thing I do when I’m feeling stuck. When my pros and cons lists aren’t helping and my head and heart feel mixed up, I flip a coin. I know—it sounds too simple and maybe too random to let a coin make a big decision in your life. But it’s not about which side the coin lands on. It’s about what you’re wishing for while the coin is in the air and how you feel when you see the result. That reveals what the heart truly desires.

In the case of quitting my job, I remember hoping that the coin would tell me to go for it. I can’t even remember which side the coin actually landed on, but at that moment, I realized that I didn’t need a sign from the universe, because I knew what I wanted.”

Dr. Brianna Gaynor, Psy.D., Clinical Psychologist, Transformational Speaker, and Director of Peace of Mind Psychological Services

“One of my life’s most significant decisions was whether or not to start a business. I remember walking into my office one day and thinking, I want to do this by myself. I’d never wanted to be a business owner before, so this was a massive shift, and I was unsure if I felt ready for or capable of this feat. I mentioned the idea to my friend Natalie, and she just said, “Yeah, you can do that.” Those five words gave me the confidence to begin to dream. From there, I got some training with another successful business owner, participated in a consultation group, and took small steps to find space and a market. That ‘Yeah, you can do that’ was the push and blessing I needed to begin and sustain Peace of Mind Psychological Services. For that, I am forever grateful to my friend.”

Tiphany Kane, Founder of KaSa Media Productions and Podcast Host

“I recently made the big decision to leave my 20-year career in public education. I was a classroom teacher for 16 years, and, after getting a Master’s in Educational Administration and an administrative credential, I moved to a professional development position in the district office. After a few years in the position, I realized it was not where I wanted to be. Many of the things I was training teachers to do were not aligned with my core values or what I thought was best for kids. I decided to apply for a higher level administrative position where I felt I could affect more change. However, I did not get the new position. When I asked my supervisor for feedback, she said the words that became the inspiration for making a huge change.

She told me, ‘Tiphany, you are just too passionate. Not everyone can meet your passion. In fact, many people get intimidated by your drive. If you want to move forward in an administrative position, you will need to dial that passion back to make people more comfortable.’

You heard that right. She told me I had too much passion—for education, for kids, and for making a difference. If she’d said I needed more experience in a certain area or had an idea of where my talents would be better suited, I would probably still be working in public education. But the feedback she gave me was about a core part of my personality: I am a passionate person. I care deeply and have a drive to be a change-maker. She was asking me to dim my light to fit into their box.

I had a big decision to make: Do I dim my light to fit in and lose a part of myself, or do I find a place where I fit in and let my light shine bright? I chose to leave public education to create my own business. I started two podcasts and co-founded a media production company, and now, I spend my days encouraging people to raise their voices and let their light shine bright. It’s been the absolute best decision I could have ever made.”

Lisa Lightner, Founder of A Day in Our Shoes

“The American workplace has a long way to go toward accommodating women, families, and those with disabilities. My son has a lot of medical needs and appointments. Sometimes, I cannot send him to school, and with needs like his, I can’t just call the teenager down the street to babysit him.

Twice, I had employers sit me down for ‘the talk’ about my attendance. My work attendance was sporadic, but I always completed what needed to be done, or made sure it was responsibly and appropriately delegated.

I realized that my son was never NOT going to be disabled, and the only way I was going to have peace was if I owned my own business. Now, I have a successful online portfolio: four websites, a consulting business, and an online training program. I earn over three times what I earned at any other job, and I make my own hours and rules.”

Caitlyn Parish, Founder and CEO of Cicinia

“Quitting my job as a financial analyst in the corporate world and starting a business in the fashion industry is one of the biggest decisions that I have ever made. I’d had the business plan fleshed out in my head for quite a while, but every time I reached the deadline I had given myself to quit my job, I would talk myself into taking more time to prepare.

One day during my lunch break, I saw a procession of women protesting against laws targeting minority communities. I saw how determined and fierce they were in their convictions; their perseverance was written clearly on their faces. A few minutes of watching those women helped me make up my mind for good. I quit my day job and plunged headfirst into the world of entrepreneurship. It turned out amazingly, and here I am now, many years later, thanks to those wonderful women.”

Written By

Madeleine Kim

Madeleine Kim is the Senior Brand Manager at M.M.LaFleur, where she started out as a stylist. She loves developing styling-focused content and creating newsletters that bring the M.M. community together.

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