7 Women Explain the Emotional Experiences of Leaving a Job They Loved

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AnnaMarie Houlis
AnnaMarie Houlis
Leaving a job you love isn't easy. You can often confuse the feeling of knowing you'll miss your responsibilities, coworkers, clients, bosses, office culture or even just your commute with perceived regret. So when better or even just different and enticing opportunities arise, taking the leap is a nuanced decision.
But you're not alone in feeling like you might be making a mistake. The fear of the unknown plagues us all, but you'll never know about the opportunities that'll come from walking through opened doors if you don't take those steps.
Take it from these seven women who've left jobs they loved for a gamut of reasons. All of them found fulfillment and happiness in their new jobs, and you can, too, with the right mindset.

1. Follow Your Gut

"I was working for a while in finances — I started at the bottom and had gained some success," says Hayley Ellis, the marketing manager for Maple Holistics. "I liked the job itself just fine, and I loved the people I was working with. As a combo, it was powerful, which is why I stayed as long as I did. But over time, things got too dry and stale for me. I felt this growing need, this craving, to wander into other territories."
The health and wellness field was one that had always intrigued Ellis — ancient traditions and medical practices, the use of old medicine in modern-day situations, chakras, pressure points and pools of energy. She decided to go for it after a good work-friend of hers decided to quit and go back to school for her Master’s. This inspired her in a way that nothing else had, since it showed her just how tangible it is.
"The mixed emotions were there, especially at first, because the moment you want to do something of significance, the chaotic elements in your universe all band together to stop you from facing your dragons and realizing your potential," she says. "That is their job, and it is your job to make a decision, don the armor, smite your enemy and reap the rewards."

The job and the people at the office — while they were a part of what was keeping her there — could not calm the fire that was building inside her. It must have been doing that for a while, or her friend’s announcement wouldn’t have had the effect it did, she explains.
"I am so very happy I decided to follow my gut, not my heart nor my head," she adds. "My head wouldn’t come to a logical decision, and my heartstrings were being pulled at from different sides — worries, concerns, logistics, the future, and what not. My gut, though, was the true savior. When my friend told me she is leaving, my stomach did a short flip; a tiny somersault. I decided to follow its example."

2. Be Open to New Challenges

"I left a job I really loved when my research grant funding ran out after 12 years," explains Carol Gee, an Atlanta-based author. "On my last day, my supervisor who, over the years became more like family than a boss, and I both cried."

Gee was the coordinator of education programs at a well-known Atlanta university; she was responsible for the day-to-day operations of a center that employed professors, student workers, volunteers and others that wrote and worked on a number of research projects. She worked hard and was rewarded with the respect of her boss who showed her appreciation by a promotion,  gifts like spa services, a massage therapist sent to her home to do a treatment for both her spouse and her.

"Had the funding not run out, I would have remained unless a better position, promotion with more money or benefits came along," she says. "My new position at another school at the same university was a great challenge."

3. Roll with the Punches

"I left a great job that I loved doing public relations and marketing for a major hospital system in Detroit," says Arielle Endelman, director of communications at the Birmingham Athletic Club in Bloomfield Hills, Michigan. "I had just had my first child and I had every intention of returning to work once my maternity leave came to a close. However, our childcare situation didn't work out as planned, and we were left high and dry until my baby was five months old. I didn't have a choice but to leave my job."
It was hard to tell her boss that she was leaving, but even harder to tell her closest colleague who had just returned from maternity leave herself, she explains. But, fortunately, she was able to find a great job doing public relations for a country club just 10 minutes from her home. Now, her son has outstanding childcare three days a week and she gets to be home with him the other two.
"What felt like a really hard situation at the time worked itself out to be even better than I could have expected," she says. "Now I have the best of both worlds: I get to be a working mom and a stay-at-home mom all at the same time."

4. Accept the Situation and Keep Positive

"It was not only a job I loved, but my dream job that I had worked so hard to get," says EB Sanders, a career coach. "I was a Humanities professor at several fantastic colleges. As I'm sure you know, education/academia is not a cash cow but I loved my job. I scrimped, saved, worked weird little jobs in the cracks between classes to make ends meet, but it finally came to a head when my options were a) move across country for a tenure track position and still be struggling financially (only now in a place far from home) or b) find a new career. I was devastated."

She says leaving her job felt like a romantic relationship was ending. It took months of soul searching and not a few tears to get to a place where she could even acknowledge that there really were other doors. Wide open doors.

"It wasn't easy or even a direct path but I'm currently a career coach teaching women how to find fulfillment in their careers, and there's no way I could be where I am without the heartbreak of having to give up being a professor," she says. "I am in love with my current job in a whole new way, and I can't imagine not being a coach."

5. Trust Your Life Path

 "I helped to run a non-profit organization in Hollywood, CA, working with people who were experiencing homelessness, drug addiction and prostitution — we helped to get them into housing, a safe community and rehab, and do free laundry for them and provide support," says Holly Pinkham, fitness and nutrition coach. "I loved it and was totally consumed with it. I left due to a relationship, which I thought was leading to marriage, because this person didn't want me to do the job anymore due to safety issues. I hated leaving, but felt it was the honoring thing to do for the relationship, as well as to hopefully get a higher income somewhere else."
She initially took a freelance job in marketing, as well as a part-time job working for another more established non-profit, also doing marketing. But she eventually ended up starting an online fitness coaching business, which turned into personal training and fitness coaching, both online and in person with clients. Fitness has always been a passion of hers, and she had previously been a personal trainer and discovered that she still felt very drawn to this industry and helping people grow emotionally and physically through the disciplines of training and good health.
"I felt so many emotions!" she says. "Leaving my non-profit job was one of the hardest things I've ever had to do. I didn't feel ready to leave, felt forced into it, and was very sad about it for a long time. I felt kind of lost — that had become so much of my identity and now I didn't know what to do, or where I fit. It probably took at least a year to really get over leaving that organization and role in my life. I felt anger toward my ex, I felt guilty for leaving, and I felt sad that such a strong passion of mine was gone."
But not too long after starting to be a fitness trainer, she found a new part-time job working for a fitness company in marketing. When her career became all about fitness,  she felt hope and excitement and that this really was her new place and purpose, which gave her a lot of joy.

"Now I feel like this is truly where I'm supposed to be at this phase in my life and love my job and helping people in a very different way," she says. "I have to trust that this path was the best for me and it rarely feels like work for me. Plus, it's far less emotionally exhausting than my previous job. I still miss that one and will always love it and participate in issues of homelessness and such as a volunteer, but  I am happy and confident about this new season of life and don't regret any of those choices."

6. Always Do What's Best for You

"I was the executive assistant to the assistant head of school at a private independent K-12 school — not only was I doing what I loved as an EA, but the school was fantastic and my boss was an amazing woman, a great educator and leader, and someone who poured into the lives of others and empowered other women," says Melissa Smith of The PVA. "She wasn't alone in her mission. I was surrounded by supportive and highly capable co-workers. Not only was I supported and compensated well, but I was also appreciated daily. I enjoyed going to work very much. I didn't think I would ever leave. I could never have imagined leaving that position for another like it. In fact, I didn't..."

She took the job at the school a year after her husband passed away and she moved back home to California. The second year, it was necessary to move back to Georgia because it was what was best for her family, she says. She couldn't imagine any position that could have been better, so she created her own. At first, she was a remote employee and then she started her own company. She had a taste of freedom and flexibility and knew she wanted more. She felt like it was a 'now or never' moment. This was her time to never have to make difficult choices again. To design a new lifestyle — a lifestyle where she was the boss.

"There were times I missed the validation; I missed the closeness of those in the office; I missed asking someone how my work was and what I could do to improve," she says. "I didn't become a virtual assistant because I don't like people; just the opposite. I love people and found new ways, which suited my business to interact with them. I hired a business coach to help me work through the questions I had. I joined networking groups and business associations to build relationships and assist others because it is my nature. I designed a support and professional development community around my lifestyle and business. It was the best decision I have ever made."

Even with all the mistakes and bad decisions she admits to making, none were fatal. Her life now is more than she could have ever imagined and her lifestyle has gone well beyond freedom and flexibility.

"I'm now location independent and traveled to 16 countries in 12 months in 2017, all while running my business," she says. "Not only is it something I do for myself, but it is also something I share and teach others about. I loved my job. However, I love my family and myself more. I love what I have created and built and will continue to do so."

7. Follow Your Dreams

"I was a flight attendant for over 30 years when I invented Finders Key Purse," says Sandy Stein, president. "My husband had just lost his job and, at the age of 53, I had a 10-year-old. I knew that my part-time work as a flight attendant would not provide the needed cash to live in Los Angeles, so I decided to see if I could make a business out of this little invention. I loved being a flight attendant. I liked the odd hours, never knowing who you meet and where you will be, no immediate boss looking at what I was doing, traveling, camaraderie with my flight attendant friends, meals out, and a chance to get away from home."

There was nothing that Stein didn’t like about her flight attendant career, except the yearly training. She enjoyed making the passengers smile and be happy, and she enjoyed knowing that that was truly her biggest responsibility. Other than that, it was go up, go down and go home, she says. So she remained a flight attendant for a year after she invented Finders Key Purse, running her business and flying around easily able to do both.

"When my business became successful I realized that I needed to concentrate fully on it," she says. "Regrettably, I retired. I knew I would miss my friends, the fun I had on planes, and my chance to escape from my everyday life on a plane. After 35 years, it is not easy to cut the cord, but I did. Periodically I wish I could be back on my flights instead of shouldering the burdens of running a business but, in the end, I have succeeded in most everything I ever wanted from making the leap, and if asked if I would do it again, the answer would be a giant yes!"

AnnaMarie Houlis is a multimedia journalist and an adventure aficionado with a keen cultural curiosity and an affinity for solo travel. She's an editor by day and a travel blogger at HerReport.org by night.