When you need to leave your job

How do you know when it's time to stop sticking it out and, instead, move on? Alyssa shares five factors she considered when contemplating leaving her job.
Image of Alyssa reflecting during a tough hike in Iceland, when she was contemplating quitting her job
Alyssa reflecting during a tough hike in Iceland, when she was contemplating quitting her job

I thought I would be a management consultant for a max of two years after business school. Five years later, I was still there. I liked the financial security of a good paycheck, solving diverse organizational challenges, being part of amazing teams and constantly learning new things. On the other hand, the hours, travel and lifestyle finally got to me. I talked about leaving my job for a while, but it was tough to make the decision without knowing exactly what I wanted next.

When I finally left, it came down to five key factors.


Sleeping, eating multiple meals a day and drinking water are the basics. If the demands of your job don’t make room for these, it’s time for a change. I traveled a lot for work, and not knowing where I would be next week gave me no routines or structure — things I needed in my life to be healthier. I would often realize I had spent the whole day hunched over my computer, forgetting to eat lunch or drink water. This was not the life I wanted to lead.

Part of this was a me problem. I didn’t prioritize my health highly enough and wanted to do my work faster, better and more diligently. Part of this was an environment problem where when a client called, I always had to be “on” and ready for anything.

Ultimately, I realized that I couldn’t be there for my husband, friends and family or do my best work when I wasn’t making time for health basics.


Energy is defined as the capacity of a physical system to perform work. My system was at capacity. I often felt physically and emotionally drained. It was hard to muster the energy to do my job as well as I wanted, let alone have a social life that required some level of planning. For more months than I would like to admit, I dreaded getting up in the morning and I stayed up later than usual to prolong the inevitability of going to work the next day. I took “Sunday Scaries” to a new level, brooding over the impending week.

Saddest of all, my lackluster energy was rubbing off on those I cared most of in life. My relationships began to feel strained. As part of reading Designing Your Life, for three weeks I wrote down all the activities in my day and rated my engagement and energy on each. For three weeks, I did not have a single work activity that made me feel engaged and energetic. That was a depressing realization.

Feedback from my professional development squad

I was constantly second guessing myself. Was I crazy to leave a good paying job where I liked the actual work? Would I regret it immediately? Hopefully, you have a support team — friends, colleagues or family whose advice you seek when making bigger life decisions. If you don’t, start by creating one. Those who care about you most can see the toll your work environment is having on you likely long before you can.

It was a reality check for me when I was catching up with an old friend and she said: “You’re still working there? I thought you left a while ago. You can do anything. Why stay if you feel unhappy?” It was a boost of confidence I needed and a reminder that I had been talking about leaving for a long time. Before I made the decision, I sought out people who gave me confidence to make the tough decisions as opposed to those who typically play it safe.

Financial options

Let’s be real. Losing a paycheck is a bitch. The fear of it certainly made me think twice about ordering my regular grande skim chai lattes while I debated leaving my job. I had to think carefully about my financial limits. How long could I go without an income before I needed to find any job to pay the bills? What were the tradeoffs I needed to make during this period? Moving in with family? Making changes to my lifestyle? (That alcohol bill might need to go down…) Not saving for a few months?

Talking about finances openly with my husband made me realize that I didn’t feel 100% comfortable quitting without having at least something part-time lined up. Knowing my boundaries and what I was willing or not willing to do financially gave me the confidence to make a decision.

Exhausting all options and finding clarity

Knowing what you want is the hardest part of knowing when to leave, especially if there’s a chance that you can get what you’re looking for at your current employer. We often underestimate our employers’ and mentors’ willingness to support our goals. If you know what you want, ask for it. I used mediation, books, coffee chats and podcasts as inspiration for self-reflection. I asked myself what specifically about my job I didn’t like and whether it was fixable. I realized that I wanted to be more entrepreneurial and try launching a few things on my own in the world. And I also realized that I missed working with social sector clients.

Chances are you have some real advocates in your company who will help you navigate your career and life goals. I asked my employer for a sabbatical to explore my entrepreneurial interests and work with an education nonprofit. To my surprise, my employer agreed! They wanted me to feel engaged and excited for my work. Initially, I thought the sabbatical would reinvigorate me to go back to consulting and find my own niche. Instead, it made me see just how much I missed owning my schedule and working on projects I am deeply passionate about.

In the end, determining whether quitting is right for you takes a commitment to self-discovery, comfort with the unknown and confidence that you are capable of figuring it out. Whether you are so burnt out that you just need the space to find yourself again or you are a woman with a plan, it never hurts to consider if it’s time for a change.

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