How Do People Leave Comfortable Jobs?

June 15, 2023
Posted in Questions
June 15, 2023 Terkel

How Do People Leave Comfortable Jobs?

Leaving a comfortable job can be a tough decision, but sometimes it’s necessary for personal or professional growth. We asked six professionals, including co-founders and freelancers, to share their experiences of leaving comfortable jobs, from transitioning to entrepreneurship to changing professions for growth. Discover their stories and the challenges they faced in making these life-changing decisions.

  • Transition to Entrepreneurship
  • Seeking an Intellectual Challenge
  • Starting a Business, Leaving a Team
  • Pursuing Personal Fulfillment
  • Navigating Cultural Shifts
  • Changing Professions for Growth

Transition to Entrepreneurship

I was a digital marketing manager for a niche marketing business. I was successful in the job and the compensation was good, but the job left me unfulfilled. I wanted to take more control of my career.

That’s why I started my marketing agency. The freedom that comes with being my own boss is great. It was difficult, however, to leave the stability of my former job.

Running the show is fun when things are going well, but on the flip side, I’m the one who is ultimately responsible when problems arise. I don’t regret my decision, but running my agency is a very different beast than working for one.

Temmo KinoshitaTemmo Kinoshita
Co-founder, Lindenwood Marketing

Seeking an Intellectual Challenge

The most comfortable job I left was a research technician job where I could structure the day as I wanted. The tasks were well-defined but just boring. There was no variety in the tasks, and I was not being challenged intellectually.

It is possible to have too much of a good thing – I got along very well with the research group, and the hours were lovely, but the work was just a grind, constant churn. Day after day, it did not seem like the work was ever finished. Through this experience, I learned that being challenged and overcoming those challenges brings satisfaction and fulfillment.

Elisha Peterson MD MEd FAAP FASAElisha Peterson MD MED FAAP FASA
Anesthesiologist and Pain Medicine Physician, Elisha Peterson MD PLLC

Starting a Business, Leaving a Team

In my earlier career, I had the comfort of being a mobile apps developer at a small company. The role was enjoyable ‌as I was one of the most experienced people there, and my input was deeply valued. But I was interested in starting my business for a while, so I left and began my solo journey.

The hardest part wasn’t leaving the job itself, but the exceptional team I’d grown so close to. I occasionally miss the friendship and collaboration that we had, the daily chatter near the coffeemaker, and how effortless my social life was back then. I’m looking forward to building my team of amazing humans like that one day!

Juliet DreamhunterJuliet Dreamhunter
Founder, Juliety

Pursuing Personal Fulfillment

I left because I felt a lack of personal fulfillment, despite the obvious outer picture of success. I realized that while the job offered financial security; it didn’t align with my personal values and aspirations. I wanted more than just a paycheck. I wanted a purpose, something to look forward to every morning when I woke up.

The hardest thing to leave behind was the comfort and peace of mind that the job provided. It meant confronting societal norms that equated success with a high-paying job. I was stepping out of a secure and known environment into a world of uncertainty.

However, this transition was also a crucial step toward my personal growth and self-discovery. I am now a life coach, helping others who find themselves in a similar situation as I was.

Bayu PrihanditoBayu Prihandito
Founder and Entrepreneur, Life Architekture

Navigating Cultural Shifts

I left my job as the Vice President of Marketing at a regional social service nonprofit in May 2022 at 55. I had been with the nonprofit for over 7 years. I was hired as a Director and successfully campaigned to be promoted to VP after 2 years.

Before that, the marketing department was not represented at the executive level. I was part of a very high-performing Cabinet team that lived and breathed the mission of the nonprofit every day. I loved the mission and the work. I was planning to work there for another 10 years and then retire.

However, a new CEO changed the culture of the organization, and I made the tough decision to leave. I took my freelancing side gig full time and started a brand strategy and content marketing company. I’m not sorry I left my job, but I am sorry I left my team with no one to look out for them. The people I worked with were definitely the hardest thing to leave behind.

Pam GeorgianaPam Georgiana
Freelancer Writer and Content Creator, Pam Georgiana

Changing Professions for Growth

Teaching adults is bittersweet. At first challenging and rewarding, it quickly becomes a routine, as you usually work with the same students and focus on similar activities.

I was an English as a second language teacher for many years, and I can relate to this description. At first, I was thrilled with the fulfillment and satisfaction it gave me.

Yet speaking in front of the group for many hours a day, encouraging (often very reluctant) students to talk, and explaining the same grammar issues led me to exhaustion. Let’s face it: after the initial momentum, learners get discouraged by the lack of immediate results. With no perspective on advancing in my career, I changed my profession entirely.

It was difficult to leave the comfort of this repetitiveness behind. With the growing dominance of English, I could not complain about the lack of resources or demand. Seeing how I boosted my students’ motivation for a long time was a solid stimulus to stick to my job.

Martyna SzczesniakMartyna Szczesniak
Community Expert, MyPerfectResume

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