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Get the Timing Right: Knowing When to Quit Your Job

What you quit and when you quit can make all the difference in the journey to reinvention, especially if what you’re trying to decide is when to quit your job. For Sara Blakely, founder of Spanx, the tipping point to quit her day job came two years after she started her company.

In 2012, Sara Blakely became the youngest self-made female billionaire when she sold her company, Spanx, for $1.2 billion fourteen years after she launched it. Spanx is an underwear maker, founded in Atlanta, Georgia, that designs and produces shaping briefs and leggings.

Blakely began to work on her idea in 1998 at the age of twenty-seven. She built Spanx on nights and weekends while still at her day job. Two years later, in 2000, she resigned from her job and pursued Spanx full time. In the two years between conceiving the idea and quitting her job, she sold fax machines to businesses, which helped her stay funded while she developed her business idea.

In Adam Grant’s 2016 book, Originals: How Non-Conformists Move the World, he cites a study of five thousand entrepreneurs who reinvented themselves from employees to business owners. The study revealed those who started their new business while in their day job failed 33 percent less than those who quit their jobs to build their business. Most businesses don’t survive a year, the opportunity to reduce the risk of failure by one-third must be taken seriously before deciding when to quit your job.

For Blakely, the day job kept her funded and provided her with an environment where she could develop important business skills she would need later for Spanx. By the time she made the decision to quit, she was ready to take those valuable skills and apply them to her own business. In those two years, Blakely also took the opportunity to validate her idea and prove customers were ready to buy her product before she pursued her idea full time.

If you considered quitting your job to pursue a new venture, it’s important to make as much progress on your idea as possible ahead of resigning so you can give yourself the greatest chance of success. One way to get started quickly is by launching a project in your new area of interest.  In fact, it can be designed and launched within days in just a few simple steps.

Blakely teaches us that a lot can be accomplished while still at your day job, showcasing how strategic decision-making plays a pivotal role in determining when to quit your job. It can make all the difference to wait until the idea is validated before you quit. Most importantly, Blakely did what was right for her given her circumstances.

Ultimately, you—not your friends, the media, or other entrepreneurs—must live with your failures and successes. The journey to reinvention is all about taking action on your terms, when you are ready, and for your own unique reasons.

Quitting Your Job While You’re Ahead

In October of 1993, a thirty-year-old Michael Jordan retired from professional basketball. Jordan made the decision to step away from the game at an age when many are still considered to be in their prime. Earlier that year, Jordan and the Chicago Bulls won their third NBA championship in as many years.

While he loved the sport and always would, he said he felt he was at the pinnacle of the sport, and he had nothing left to achieve. Without motivation and desire, it didn’t make sense for him to continue. He also explained that to become the greatest basketball player, he sacrificed precious time with his family and dear friends. In the next chapter of his life, he intended to dedicate more time to his wife, kids, and dear friends.

To walk away from anything is difficult, so to do so when you are ahead seems crazy. It can also elicit feelings of guilt.

“How dare I leave such a blessed and great working situation when other people hate their jobs?”

You can quit your job and in these cases, it is exactly what you need to move closer to your values, passion, and purpose. When to quit your job is a deeply personal decision that should be based on your individual circumstances, aspirations, and long-term goals.

When I considered quitting my first job to pursue my new interests, I felt a great deal of guilt. I had invested so much into the career path I was on, and it was going well. For four years, I worked hard and built a track record of success. In addition, I was part of a competitive leadership development program. Programs like that one were a fast track to senior leadership roles, and I was only a few months from completing it. I wondered, How could I possibly give up on all of this progress and start over again?

I was certain reinvention meant giving up all I invested and starting from zero again. However, as I struggled with my decision, I realized that understanding when to quit your job is a crucial aspect of personal growth. It’s not just about walking away from something familiar; it’s about recognizing the signs of discontentment and aligning your passions with your career.

In Seth Godin’s 2020 book, The Practice: Shipping Creative Work, he writes about the fear of abandoning sunk costs. Sunk costs are the resources, time, and effort already committed and invested that cannot be recovered if we decide to walk away. The sunk cost fallacy nudges us to stay on the committed path even when something doesn’t feel right. Seth shares that as strong as the pain of losing a sunk cost might be, often it’s better to let go of something that doesn’t work. Our future selves will often thank us for doing so.

I faced precisely this type of dilemma. On the one hand, I had a great job I already invested so much into (my sunk cost). A part of me wanted to continue investing in that path (the fallacy of the sunk cost) because I was afraid to abandon it. However, that path was no longer of interest to me and no longer served me or my future self. As difficult and scary as it would be, I was better off letting go of my sunk cost.

In the process of deciding when to quit your job, you can ask yourself empowering questions to help you create a counterweight to the sunk cost fallacy. Consider the following questions.

• What if a path aligned with my values, passion, and purpose offered the possibility of an even greater result?
• What if the good thing I currently have is at best, only just good? Would that be good enough for me?
• What incredible possibilities will I miss out on if I do not pursue my interests and passions?

These questions create an opportunity for you to tap into the fear of missing out on your best life and use it help defeat any sunk cost fallacies. As you grow and evolve, your previous passions may no longer be interesting. On my journey, I learned that pursuing a life aligned with my passions and purpose always led to fulfillment and happiness, not necessarily wealth or other external forms of success. The fear of missing out on an aligned life has significantly outweighed any sunk cost for me. That said, fears, sunk costs, regrets, and other considerations are specific to you. Ultimately, when to quit your job or any other major step is your decision to make, and no one else has to understand your reasons and rationale except for you.

Quitting Because You’re in the Wrong Game: Understanding When to Quit Your Job for a New Beginning

An experienced and talented engineer, Luis, felt unfulfilled at work. The work itself was great because he enjoys solving complex problems. The problem was the political game of promotions and pay raises that dominated the culture at his company. When Luis presented an innovative solution to a new problem, his colleagues thought he was only trying to secure a promotion or raise. Given the culture and the fact that most people were looking for promotions and raises, it made sense that they would see him the same way. Fortunately, some people knew that wasn’t the case and that he was driven by solving problems. While some considered him a threat, others embraced him as a world-class problem solver they could go to for help.

When the focus shifts toward limited resources, people tend to activate a scarcity mindset and behave as if their loss is someone else’s gain and vice versa. This mindset caused people to become skeptical of any offers Luis made to help them solve their problems, fearing he would take the credit and scarce rewards. This was frustrating for Luis. However, the dominant culture dictated that people adopt a winner-take-all mindset. Luis and his colleagues were pursuing different objectives and their strategies for success were always going to come into conflict. The misalignment made it difficult for him to be happy and fulfilled in his role. He loved his job. However, he didn’t like the culture.

An important question arises in situations like these: when to quit your job? Evaluating the alignment between your personal values, career aspirations, and the prevailing culture becomes crucial. It is essential to determine if the environment supports your growth, recognizes your contributions, and fosters a sense of fulfillment. Have you ever felt this way? On the one hand, you love your job. On the other, the environment or culture is not right for you.

Sometimes you are in the right job, but the company might be the wrong fit. You might play for one set of objectives while everyone else plays for another set. You can approach situations like this a few ways. If the culture is company-wide, you might consider looking for the same role in a new company. However, quitting the company isn’t your only option. You might quit the team you are on and join another one at the same company. Ultimately, your mission is to find or create an opportunity that is aligned with your values, passion, and purpose.

Quitting Does Not Have to Be Forever: Knowing When To Quit Your Job Can Be a Transformative Pivot

On March 18, 1995, two and a half years after he retired, Michael Jordan announced his return to basketball with a press release that simply said, “I’m back.” In the following three seasons, Michael Jordan won three more championships. The fans who were upset with his decision to quit years earlier were right, he could have and did win three more championships. However, he did it when he was ready and on his terms.

Two years after I quit teaching math, I made my own return to the classroom on terms that suited me better than my previous teaching job. The new role was part time, and I had freedom to build the curriculum the way I saw fit. My focus was mostly on teaching this time, which allowed me to be at my best for students.

Sometimes, we think of quitting as a forever decision, which is understandable. After all, in the moment, it’s a significant decision with serious consequences. However, once you figure out when to quit your job, remember that quitting does not have to be forever. It can be for a little while. The key is to approach quitting as a means of self-discovery and growth. It’s about giving yourself the freedom to pursue different paths, experiment with new possibilities, and redefine success on your own terms.

Quitting can be an opportunity to explore other interests that may or may not materialize into future careers. However, they can still play a role. At one point, I explored working with musical talent, booking music gigs, and setting up audio equipment for events. That didn’t materialize into a new career. Michael Jordan explored his interest in baseball after he quit basketball. He didn’t stay with baseball, but that was okay because it allowed him to reignite his passion and motivation to play professional basketball again.

Understanding when to quit your job and ultimately quitting can also be an opportunity to gain perspective by stepping away from something you’ve been a part of for a long time. According to Walter Isaacson’s 2011 biography Steve Jobs, we learned Jobs was forced to step away from Apple in the mid-eighties, but he later returned to Apple in the late nineties with a great deal of new perspective and experience. This equipped Steve to take Apple from a mediocre company to one of the most recognized and valuable companies on the planet. He learned valuable lessons in marketing, innovation, and sales during his time away that made a significant difference for Apple when he returned.

Finally, you might quit because you simply want to be with yourself and reflect before moving on to a new chapter. Whatever your reason, it’s yours to make and live with. People may not understand, but only you must understand your reasons. This is your unique journey and there will only ever be one exactly like it. People can offer support, encouragement, and feedback. However, the journey is yours to walk and they can’t know exactly what it feels like to you.

The decision to quit is not one to take lightly, and you don’t only make this decision in your career. When to quit your job is just one of the many questions you can ask yourself along the way. Tony Robbins often says, “Quality questions create a quality life. Ask a better question, get a better answer.”