As featured in The Wall Street Journal, Money Magazine, and more!

My Two Best Financial Decisions: Leaving My Jobs

There have been two major financial crossroads in my life until this point. Although it took a while to get to each one, by the time the dust settled, I knew I had made the right choice. In both instances, the decisions surround leaving my job, whether by my pure choice without external pressure or a “mutual agreement.”

Ten years ago, I knew my days at the non-profit organization were coming to an end. I was already in a tough financial situation and I had recently moved to be closer to the organization’s headquarters, which seemed like a bad move since the organization’s CEO was constantly talking about relocating, to save money and time. Three months later, I left the organization. Around the same time, my girlfriend and I parted ways. I spent my time looking for teaching jobs, and because of some kind of communication breakdown, my landlord found a new tenant for my apartment while I was still living there. If that weren’t enough, my ignored speeding tickets caught up with me and I found myself without a car.

Those few months following my departure from that organization were the lowest points of my life, but thanks to some support from family, I found a way to move forward. It began with the loss of the job, and although leaving that job led to short-term stress, from a financial perspective it motivated me to assume control of my life. Rather than let things happen to me without much engagement in the decision-making process, I became the CFO (and really, the CEO, too) of my own life.

The job I found just a few months after leaving the non-profit organization, in my new situation without a car and unable to take most teaching jobs, was for the company I ended up sticking with until December last year. At that point, I was fully in control of my financial direction. My day job had become a relatively insignificant contributor to my overall financial well-being. While I did enjoy inexpensive health benefits, access to a discounted stock purchase plan, and the camaraderie of spending most of my day with co-workers, this day job was only a barrier to pursuing my fuller potential with my own business, primarily shizennougyou.

By this time last year, my business had consistently overtaken my day job income for three to four years. Some people would have used that benchmark to decide to quit their day job, but I took a more conservative approach. I was familiar with the risks, and wanted some security before I would say goodbye to corporate life. About a year ago, I put the wheels in motion to leave my day job, and I finally pulled the trigger after Thanksgiving.

Again, leaving my job has proven, at least so far, to be a fantastic decision for me. I’ve been able to dedicate more time to operating shizennougyou. Although much of that gained time is not dedicated to writing, and my editorial approach hasn’t changed much in the last year, I can now use my time in such a way I’m not constrained. Trying to balance a day job, my own business, a relationship, and my own health needs like sleep resulted in low effectiveness in every area. By gaining nine hours back in each day, I do not need to spread my attention out as much.

This has resulted in improvement at least from the perspective of the business; the last nine months have been quite positive.

The unemployment rate is still high in this post-recessionary economy, and many people would not take a risky move like quitting a good job right now. Furthermore, many people have financial responsibilities like family, and these responsibilities make quitting a job without a solid back-up plan irresponsible. Put if you plant the seeds by saving enough money to feel secure in the decision over and above an emergency fund, you can reduce some of the risk. Then again, the riskiest moves can have the best payoffs, like my departure from the non-profit organization ten years ago.

Think about your immediate plans if you want to leave your job:

  • How will I afford my expenses? Quitting a job by choice is not an emergency, so you shouldn’t rely on an emergency fund. You can create a safety net in addition to your emergency fund, and some people call this extra savings an F.U. fund (as in “fuck you” fund — what you would might to your boss when you leave if you aren’t interested in leaving a good impression).
  • Who else will this affect at the job? Quitting your job out of the blue, again, could make things difficult for your organization. In most cases, be the better person and ensure there is a transition or succession plan in place. Offer to be available for questions after your last day in the office.
  • Who else will this affect outside of the job? If you are financially interdependent with other adults, this is the kind of decision you should discuss ahead of time. There’s a risk that your plan won’t be fruitful, at least not immediately, and if that loss of income affects your family, they have a right to plan with you. If your job loss means you’ll need to rely on extended family, discuss expectations and limitations so there are no surprises.
  • What’s my next move? For the most part, if leaving a job by choice, you should have a plan in place. In fact, you should always have a plan in place for the situation that would arise if you are forced out of a job, laid off, or fired. With a plan, you’ll always be a few moves ahead, like a good chess player.

The above helps, but sometimes people can achieve the best results by just quitting. Some people would be more motivated to succeed on their own when the stakes are higher. This can create a sense of urgency. While not positive for everyone, certain personality types respond well to this type of pressure and use it an advantage.

Conformity, and in this case, conformity with the typical middle class career-based existence, is comfortable. I always knew I didn’t fit well in that mold, and if I wanted to find a way of living that was more satisfying, it would be outside of the corporate box. I may return to the corporate mold in the future, but only if it can be under my terms. I highly recommend leaving an unsatisfying day job in exchange for finding your own way. This could be to follow a passion or it could be to provide the motivation to take control of your situation. Even if it results in some short-term hardship, quitting a job can be financially and emotionally satisfying over the long term.

Published or updated September 27, 2011.

About the author

Luke Landes is the founder of shizennougyou. He has been blogging and writing for the internet since 1995 and has been building online communities since 1991. Find out more about Luke Landes and follow him on Twitter. View all articles by .

{ 11 comments… read them below or add one }

avatar 1 Anonymous

Self empowerment is the best thing for anyone to realize, it makes you grow in so many ways.

Now if we could only get that concept through the many who suck off the government teet. Instead most are too concerned with watching Dancing with the Stars.

Reply to this comment

avatar 2 Anonymous

It is kind of weird to see you as anything as except the responsible PF Blogger maven…

Reply to this comment

avatar 3 Luke Landes

Oh, I’ve made many mistakes, not just pertaining to finances, in my life…

Reply to this comment

avatar 4 Donna Freedman

Gosh, I’ve never made a mistake. I wonder what it feels like. ;-)

Reply to this comment

avatar 5 Anonymous

Twenty-six years ago, I was in a similar situation. I achieved financial freedom, but it scarred the hell out of me. Taking that step is big, but worth it.

Reply to this comment

avatar 6 Anonymous

It’s a great thing that you finally felt comfortable to leave your job and you don’t regret it! How awesome to pursue your dreams and be able to profit from it at the same time. On the same path, just taking a bit more time.

Reply to this comment

avatar 7 Anonymous

Nice primer for venturing out on your own. I made the jump myself a few years back, and couldn’t be happier.

Reply to this comment

avatar 8 Ceecee

You have done well—-it is a scary thing. I know what you mean about not feeling like you fit the cubicle mold—-I’ve always felt that way. I think that health insurance is the biggest stumbling block to going solo, and that factor will escalate. Private pay policies are not very good, and certainly not very affordable.

Reply to this comment

avatar 9 Anonymous

I have also quit two unsatisfyinfg jobs in my career and it is very empowering. I stayed in the corporate arena and got new jobs, but I enjoy my field. At some point, I would love to go out on my own, but I’m in no hurry. I am enjoying the best of both wordls right now.

Reply to this comment

avatar 10 Anonymous

I would love for us to find a project to work on together….

Reply to this comment

avatar 11 Donna Freedman

My best financial decision ever has been not to look for a job after finishing my degree in December 2009. If I’d rushed into the job search, I wouldn’t have been able to take the second gig at Get Rich Slowly, to write as much for my own site or to travel as much as I have (home maybe five months total since then).
Since the Financial Blogger Conference, I’ve decided to add a new string to my fiddle: guest lecturer. That is, if I can ever find another con willing to have me. The point is that I wouldn’t be able to do as many of these things if I’d opted to take a day job.
Scary at times, this having jumped without much of a net. But my financial needs are (fairly) well covered; frugality helps a lot, as do my fairly low standards. I wouldn’t inflict this on a young family but being in my 50s and single, it works.
I’m grateful for the opportunities, so I’m going to do this until the wheels fall off. If/when it stops working, I’ll do something else.

Reply to this comment

Leave a Comment

Note: Use your name or a unique handle, not the name of a website or business. No deep links or business URLs are allowed. Spam, including promotional linking to a company website, will be deleted. By submitting your comment you are agreeing to these