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The Hardest Part Of Career Reinvention: Quitting Your Job

Quitting your job is one of the toughest decisions in career reinvention. After all, for most of us, the salary or pay we receive contributes directly to our living expenses and other financial obligations such as debts, family expenses, healthcare, etc.

When I considered quitting my first job, I tried to convince myself quitting wasn’t necessary. I wanted to make the argument against quitting. Quitting a corporate job went against everything I was taught about financial responsibility, career development, healthcare, and success. I would likely burn my career bridges and relationships. Future employers would probably ask about these “gaps” in my résumé, and I’d have to find a clever way to spin it in a positive way.

At the time, I owed almost one hundred thousand dollars in student loans. If I struggled to make my monthly payments, my credit score would be damaged for a long time. This meant I would have a difficult time buying a house or car in the future. In so many ways, it seemed quitting would be the biggest mistake of my life and if you’re considering quitting your job right now this might resonate with you very well.

It may seem paradoxical, but the very job you want to leave could be what makes quitting your job challenging. In my case, I enjoyed my job a lot because of the travel and the people I worked with. They were good people who became dear mentors over the years. I learned so much from them and felt I owed them to stay on the job. If I left, I would let them down.

I asked myself, Am I seriously considering throwing away everything I’ve worked for the last eight years? If I screw this up, could I recover and get back on track with my corporate career?

I thought maybe it might be better to make money first and pursue passion later in life. This seemed like the responsible thing to do. This plus the multifaceted pain of quitting seemed clear to me. No matter how I looked at it, quitting would cause a lot of pain and discomfort. Staying would mean I do things the right way—financial stability first, then passion.

Passion or Paycheck? How to Balance Your Dreams When Quitting Your Job

As time passed, it became increasingly challenging to prioritize financial stability over pursuing my passions: my passions were elsewhere and got stronger by the day. I was in love with teaching math. I wanted to spend more time doing that. As painful as quitting might be, it also meant I could start to build a life that was aligned with my new passion.

This inspired me to consider the pain of not quitting (and I encourage you to go through the same thought process if you’re struggling with the decision of quitting your job). What are the consequences of not quitting? What happens if I do not pursue this career reinvention? Would I regret never having tried to reinvent myself? What would I miss out on if I did not quit?

For me, the worst possible outcome would be a life of regret. I felt certain this pain would bother me for a long time. One night, I had a dream where I had a wife and two children, like my parents did. In that dream, I had chosen the path of not quitting, and I felt a deep sense of anger with myself and a lot of resentment. What hurt the most was knowing I could not turn back the clock and change the past. At that moment in the dream, I felt hopeless. This wasn’t a dream. It was a nightmare.

I did not want to live with the regret of not having tried to pursue a path I believed in my heart to be a better fit for me. Quitting would free up my time to teach more and discover other ways to help people have breakthroughs in their life. Even though I wasn’t sure exactly what the new path would look like, I knew that quitting was an opportunity to build a life in alignment with my evolving values, passion, and purpose. As scary as quitting your job might be, it might also be the foundation for a fulfilling life. If I stayed in my job, I wasn’t going to be any closer to figuring it out. And success wasn’t even the goal anymore. All I cared about was knowing I tried everything I could to pursue what mattered to me even when the naysayers encouraged me to stay.

Preparing For The Naysayers When Quitting Your Job

I found no shortage of naysayers when I discussed the possibility of reinventing myself which is why preparing for them is crucial when quitting your job so that their doubts and criticism don’t discourage you from pursuing your goals. Each naysayer shared at least a few reasons and warnings for me to consider. A few people thought I was crazy to consider such a risky move. Some were noticeably triggered by the idea of quitting and projected their fears onto me. One person even lectured me on the virtues of not quitting because after all, quitters never win. That said, I no longer wanted to win the game I was playing.

This wasn’t all bad because they helped me consider the many things that could go wrong with reinvention. I appreciated these gifts and considered some of them in my plans so I could control for and mitigate as many risks as possible. I knew there was no way I could eliminate all of the risks. However, I came to appreciate the gift of awareness.

My parents were also concerned about me and what might happen if I quit. I knew I was fortunate to have parents that cared about me enough to worry but also encouraged me to do what I felt was right for me, even if they would have decided differently themselves. Their love and concern provided me with a boost of motivation and purpose for the journey. I wanted them to know their hard work paid off and I was going to be okay.

My wife at the time didn’t have the same luck with her own reinvention. Her parents didn’t support her desire to pursue an entirely new career path. Nevertheless, she moved ahead with her reinvention. Shortly after, her father cut her off and stopped talking to her. This motivated her to succeed because she didn’t want to have lost them for nothing. Reinvention came at a great upfront cost to her. That powered her drive to succeed, and she did. Fortunately, a few years after we got divorced, she and her father patched things up again.

There will always be naysayers when quitting your job and that can be a good thing. They help you identify and calculate the risks you might otherwise miss. And in most cases, your naysayers genuinely care about you, and this is their way of showing it. Fortunately, optimists are also out there.

How Supportive People Can Make Quitting Your Job Easier

One of the optimists I encountered during the time I was considering leaving my job was Greg. He worked for the same company I did in the model shop at the factory. The model shop was where all custom build projects would go for special hands-on attention. The project I worked on was still in the development and testing phase, which required me to work closely with Greg and the rest of his team.

Greg was ten years older than me, married, and had a couple of kids. He was a really nice guy, and I always enjoyed speaking and working with him. He always remained calm, even when tempers flared in the model shop. If the head of the model shop wasn’t around, I went to Greg because he always pointed me toward a solution.

One day, I told Greg I was thinking about quitting my job to pursue a new passion. I told him all about my part-time job teaching math at the learning center and how much I loved that work. It was probably obvious how excited I was just talking about it. I told him I was seriously considering it but most people thought it was a bad idea. I asked him, “What do you think, Greg?”

He said, “That’s awesome that you found something you really love and are thinking about pursuing it.”

I said, “Thanks! I think you’re the first person to actually be excited for me.”

Then he said, “Don’t worry about the naysayers. They mean well and are probably scared for you. You know what, though?” he asked.

I replied, “What’s that?”

“When I was your age, I had a few ideas I wanted to pursue too.”

“Really? What happened?”

He replied, “Well, in the end I didn’t. I wasn’t sure if it would work out and decided against it. Then I started to build a family, bought a house, and at that point taking a risk would have been really difficult. I love my family and would never change that, but a part of me still wonders what if I had tried. Would it have worked? I guess I’ll never know.”

I stood there silently, listening and processing.

He continued, “I’m excited for you, man. This is a great time to pursue your passion. Go for it. Whether it works out or not doesn’t matter. In the end, you’ll never wonder what if.”

It became clear that the cost of not pursuing reinvention was significant. I distinctly recall thinking a lot about the fear of regret during that time. The fear of regret can be a powerful motivator for taking the leap and quitting your job to pursue a new path.

Conquering Your Worst Fear When Walking Away From Your Job

Even with the fear of regret motivating me to act, I still wanted more certainty. I pushed back on myself and asked, What purpose would quitting serve? What would quitting allow me to do that I cannot do now?

That’s when it hit me. I realized my current job no longer served me, which stunted my growth and development. My job was holding me back from becoming my best self. Even though I didn’t have absolute clarity of what I wanted to do next, I knew teaching math was going to move me closer to my goal than my day job was.

Quitting your job is not only about leaving behind a job that isn’t serving you anymore. It is also about moving toward a life aligned with your values, passion, and purpose.

At that moment, I started to coordinate and plan for the risks I had learned about. I restructured my student loan debt, devised a plan for cashing out my retirement funds, and calculated how far my financial runway would take me. However, even all that preparation didn’t address my biggest fear—filing for bankruptcy and ending up homeless. I worried that if I spent all of my runway and could not get another job, I’d have to file for bankruptcy and likely end up evicted from my apartment. I decided to talk to one of my mentors about this.

On a trip to San Francisco I caught up with a dear mentor, John Furey. He asked me to meet him in Sausalito, across the famous Bay Bridge in San Francisco. Sausalito is home to some of the most expensive and beautiful real estate in the country. We decided to meet for lunch, and he suggested a little taco place by the bay.

“John, can I ask you something?”

He said, “Sure, what’s on your mind?”

“You know all about this reinvention I’m considering and even though in so many ways I feel like I’m ready to quit, I’m still afraid of failing to the extent where I have to file for bankruptcy, or worse yet, ending up homeless.”

It wasn’t much of a question, but it was enough for him to go into mentor mode.

He let out a very short burst of laughter. Not the kind that makes you feel embarrassed. More like the kind that makes you realize you totally missed something because you were too busy catastrophizing what quitting your job might mean.

“Let’s say you got evicted tomorrow. Who would offer you a couch to crash on?”

Instinctively, I listed five friends, not to mention my parents and sister. I even told him that one of my friends would probably offer me a guest room.

He didn’t say anything. Instead he let my response sit for a little while. And just like that, he’d made his point.

He then said, “If you become homeless by quitting your job, it will be because you chose to do so, not because you had to. You have no less than five couches and a possible guest room to live in if you get evicted.”

Almost as if I wanted to win this argument and prove I could end up homeless, I replied, “Okay, I see what you mean, but what about bankruptcy? I have a lot of debt and bankruptcy follows you for at least seven years. I wouldn’t be able to do anything with my life after that.”

Again, not a well-constructed question, but good enough for him to respond to.

“Roger, bankruptcy is nothing more than a set of rules that change with each administration. It’s a bunch of pieces of paper in folders that say things. You are more than a few pieces of paper. You have more to offer the world than a good credit score. Even if you did have to file for bankruptcy, those pieces of paper would never define the incredible value you can bring to the world.”

I never thought about it that way. Was I really scared of a few pieces of paper? Yes, I was. However, on that day, I resolved that I would no longer be afraid of pieces of paper. This shift in perspective was just what I needed to get over the last obstacle.

Quitting your job is not always easy, but it can be a transformative decision that changes the course of your life.

Quitting still carried a lot of risk. However, it was also a means to an end; I was not quitting for the sake of quitting. I was doing it so I could get onto a new path. I wasn’t running away from a job as much as I was running toward becoming my best self and living my best life. If I was running away from anything, it was a lifetime of regret.

Was there any guarantee of success? Absolutely not. In fact, it was more likely I would fail and possibly many times. However, that was no longer the point. My reason for quitting this job was to look back one day and be able to say, “At least I tried and failed.”

Alfred Lord Tennyson once said, “Tis better to have loved and lost than never to have loved at all.”

I recall thinking about this quote just when I was going to make the decision to quit. The response to, “What happens if you don’t take this opportunity,” can be summed up by that one quote.

Quitting your job is not an easy decision to make, and it requires a lot of thought and careful consideration. Our naysayers can make you aware of the risks, and your supporters can encourage you during the tough moments. Everyone’s path and process to make this decision will be different, but you will likely have fears to conquer along the way. The important thing is to frame fears in such a way that they empower you to do what is right for you. For me, that meant focusing on the fear of regret instead of the fear of financial ruin. For you that might mean something else.

Reinvention most likely won’t be a smooth ride. However, it is the path to becoming your best self and living your best life—a life that is aligned with your values, passion, and purpose. Quitting your job is just one of many steps along the path.

Before your quit, consider attending one of my upcoming Reinvention Project Design sessions so that you can take the first step to evaluating whether quitting is right for you. You can register here.