Should I Quit Now or Later?

These days, I often think about how much longer I should (and can) stay at my current job. Staying would certainly help my goal of pursuing otium and financial independence. But at what cost? Is financial independence worth sticking it out for a few more years, or should I embrace the unknown, to pursue my best life sooner?

Sometimes, I feel like I can stick it out for a few more years. Other days, I feel like I need to quit immediately.

My job actually isn’t that bad. In many ways, it’s almost “as good as it gets,” at least in terms of potential wage-earning opportunities for me. There’s a reason why many biglaw attorneys hope to “go in-house” one day. But, I’m not merely looking for the ‘least worst’ job, but seeking to live my best life. And, I don’t think working a full-time office job, no matter how good, is compatible with that.

Arguments in Favor of Staying

Earn more money. I currently make enough to live a comfortable life, while saving well beyond the annual 401k limit. I don’t currently make as much as I would’ve had I stayed at a large law firm, in terms of salary and bonus. But, it’s enough so that it’s a no-brainer for me to work where I do, with higher job satisfaction and a better quality of life. And, there’s a possibility that the equity I have in my company may more than make up the difference someday, although it’s still a lottery ticket at this point (higher risk, higher (potential) reward).

Company mission and goals. I was initially attracted to my current company because of its important mission and ambitious goals. We’ve come a long way and it’s been a privilege to be a part of that, but there’s still a lot left to achieve and we’re on the cusp. It would be professionally and personally gratifying to help the company reach its next big milestones. If I were to leave now, I would feel like I was leaving unaccomplished business behind. I kind of want to see the company get to the next stage while I’m there, as a capstone to this chapter of my career.

Teammates. My colleagues and I have been through a lot together these past years. We’ve helped the company grow from a small, scrappy company to one that now punches above its weight class globally. Similar to the above, I would feel like I’m letting my team down if I left while there’s still a lot of work left to do. Our team is a special group of people who are extremely capable, hard working and good humored, but yet aren’t a-holes. They are a pleasure to work with. I don’t want to leave them without a good reason. If we accomplish our collective goals together, it would be uniquely satisfying and rewarding.

Growth Opportunity(?). As the Man in Black says in the Princess Bride, “Life is pain… Anyone who says differently is selling something.” I’m not a masochist and don’t enjoy suffering. I don’t think there’s anything inherently wrong with “quitting,” if there’s a good reason. But, I also don’t want to shy away from a challenge, if it will make me a better person or lead to a desired outcome. And, whether or not I quit, there will always be challenges and unexpected events in life. If I can learn to survive my job, and overcome my current ennui, that might help me overcome other obstacles in the future. As long as it doesn’t weaken me in the process…

Inertia. I’m comfortable in my role. I do it well. I’m familiar with the people I work with, and vice versa. People trust me, and I have a lot of autonomy as a result. I’m no longer at the law firm, consistently working 60-80 hour weeks, at the whim of demanding clients. While it’s not a ‘9 to 5’ either, I generally have predictable hours and there hasn’t been as much evening and weekend work recently. If I quit now, before I’ve achieved financial independence, I’ll still need to make money somehow, and the alternatives might not be better. But, if I continue working at my current job, even a couple more years will bring me much closer to financial independence.

Temporary Refuge. While I figure out what to do next, it helps to do it from the vantage point of having a secure, well-paying job. If the stock market crashes or any unexpected expenses arise, I’ll still be earning money. If any unexpected health issues arise, I’ll have excellent health insurance. If I decide to look for another job, it’s easier to get a job while still having one. If I decide to purchase a house, it’s easier to get a mortgage while employed. When I go on vacation, I’m pleased to know that work is essentially covering my vacation. Once I quit, I hope to never have to work for money again, and I want to avoid needing to search for work when I’ve been out of the workforce for years. Having a job allows me to make decisions from a position of strength.

Arguments in Favor of Quitting

Life is short. If I knew I would not live to old age, I would quit immediately. Even though I don’t know that, I do know that life is uncertain and that I won’t get back any time that has passed. Each day I’m working in an office is another day that I’m not living my best life. There’s definitely something to be said about taking steps towards a more fulfilling life immediately, even if the future is uncertain, rather than biding my time in a certain unsatisfying present. As the spirits sing in Woody Allen’s movie Everyone Says I Love You, “Enjoy yourself, it’s later than you think. Enjoy yourself, while you’re still in the pink.”

Carpe diem. I would much rather explore the possibilities of the future while I’m still young and healthy, and while friends and family are too. If I wait too long, I might not have the physical or mental strength or stamina to travel, explore the outdoors, and try new things. Or, friends and family may no longer be able to travel or walk long distances or enjoy life as they used to, or may have obligations that restrict their freedom. Things can change, quickly, so I would like to enjoy the present time as much as possible.

Health. Quitting would benefit my physical and mental health. My current job involves sitting at a desk and staring at a screen for long periods of time, stressful situations, urgent projects, long to-do lists and getting my mind pulled in many different directions simultaneously, and it often comes home with me during evenings and weekends. Leaving that behind would afford me time to do the things that I want, focus on healthy eating and living habits, get me outside of a sterile office environment and unclench my mind.

Live real life. Work often feels artificial. My company’s impact in the real world is not, but treating the pursuit of financial goals as life or death, the constant push to do things faster, the demands of people internally and externally — sometimes, it’s hard to care about things as much as other people seem to. I care about doing a good job and I care about the outcome, but I wish people put things into perspective. I get a sense of purpose from my work, but my identity isn’t dependent on it.

Similarly, it’s hard to build real relationships with people at work, as I feel that people see me primarily as the means to get to their desired end, and not as a person who has hopes, dreams, ideas and needs beyond our company. Work is laser-focused on growth and success, but real life (at least what I seek) is much more non-linear and meandering. I want to live a life that can’t be easily quantified, measured or reduced into inputs and outputs. Quitting lets me pursue that life immediately.

Enough money (for now). I don’t have eff-you money, but I have eff-it money. If I quit today, I have enough savings to support my current expenses and standard of living for several years. That gives me options, as I don’t “need” my job to live in the near-term. And, it’s possible that quitting would lead to new opportunities that are a better long-term fit for me, as I could afford to be choosey about what I did next. This isn’t really an argument in favor of quitting, but more of a recognition that money isn’t a huge limiting factor.

Low risk, high reward. If I quit and things don’t work out, I can go back to work. Perhaps, I could even return to my current job if I wanted to. On the other hand, if I quit, I would have the opportunity to pursue a more fulfilling life. If I succeed, then I will be fortunate to be living the life that I want, and that, ultimately, will be more sustainable than the current path I’m on.


It’s clear that I need to quit sooner, rather than later. Perhaps not immediately, but I need to figure out what my next step is, and when. My current thinking for my current job is another year max, but that timeline could get accelerated or delayed depending on what happens in the upcoming year.

As far as what lies ahead, I know that I will need to continue making money for at least a few more years to reach financial independence. But, it doesn’t necessarily need to be in a full-time office job. One of the areas that I’ll be looking at are part-time and remote opportunities, and/or mature companies that are more low key than a high-growth startup.

It’s also possible (likely) that I’m burnt out and just need some extended time off, but I don’t think that would address the underlying issues inherent with my current job and industry. So, I plan to look for opportunities that are sufficiently different, and bring me closer to what I’m looking for.

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