Will you have the courage to quit your job?

Here’s a thought-provoking question from a member of a financial independence forum I hang out on.

I’ve reached my magic number. I’ve cut back on my hours. The end is in sight.

“However, I find myself vacillating between exhilaration and terror. Am I going to regret this? Should I work another 5 years? This lighter job isn’t so bad (though the opportunity cost is significant.) Once I walk away, it would be very difficult to return, and essentially impossible to regain my current earning potential.

“Does anyone else on the cusp of FI/RE have a severe case of cold feet? What did you do?”

What would you do, O Gentle Reader? Ever wondered whether, having reached your financial independence target, you’d have the courage to quit your job?

Once upon a time you decided to trade freedom for security. And you got comfortable, or at least for a while. So when you’re finally able to trade back your security for your freedom, you’ll of course be uncomfortable. It’s a major major major decision in your life; one you may never be able to unwind.

I’ll tell you straight up: I had terribly cold feet. Zero kelvin.

Much like the person who asked this question, I mentally prepared myself to quit my job for years and years. But just as I hit that number, my wife and I had a kid and my company reorganized and another department absorbed mine.

You want to talk about cold feet…Jesus; now those were cold feet. For a while there it looked like I was going to get forced out whether I wanted to go or not, and if our daughter hadn’t been healthy…

But what warmed my poor feet back up was this: at the last minute my company offered me a job across the country.  I ruminated for a week, then asked to work the job on a three-month trial basis…suspecting all along I wasn’t going to take it. But this bought me some time, and in the interval another round of my employee stock ownership plan matured. I was also carefully watching what kinds of severance packages other people were getting.

At the end of the trial period I decided against the west coast job. I didn’t particularly enjoy it, and again, I’d reached my magic number. But even if I’d taken it, get this: I lived on the east coast and the company wanted to put me in charge of east coast long-term business development, but the VP I’d be reporting to denied my request to actually live on the east coast. Wanted me to move to LA because, “I like to have my people around me.”

I thought, “I shan’t be gnawing on any  more bullshit sandwiches.” During a long drive I phoned in my notice, negotiated with HR for three or four days about specifics (there had been a big age-discrimination lawsuit so they were tiptoeing around their senior people), showed up at the office to sign paperwork, had an exit interview, arranged to collect my severance pay, and split.

This was the kind of place where if you had proprietary knowledge, the instant you’d officially severed an HR rep confiscated your laptop and escorted you out of the building–in a friendly way, of course, but a casting out nonetheless. I’d showed up at eight that morning to deal with the exit process, and I was on the train on the way home by ten.

With–for the moment, at least–cozy warm feet.

Fear is natural. But here’s an important point to consider: your feet will always cycle through being warm and cold depending on your life events–whether you have control over them or not. Remember the housing bubble? To mix metaphors, there are people who say they’d hit the door and never look back, but I’m thinking the majority will stand there with their feet on the knob, testing its temperature, for a good long time before they muster the courage to turn it.

And in my experience that lingering fear never completely goes away. But understand this: as time passes your confidence will grow and your fear will diminish.

Here’s another point to consider. Oxford and Cambridge academic C.S. Lewis, a personal friend of J.R.R. Tolkien, often wrote about the dangers of excess precaution. Here are two quotes from Lewis’s “The Screwtape Letters“, where a wise old devil named Screwtape is teaching his nephew and protégé, a lesser devil named Wormwood, the fine art of ensnaring human souls–specifically Wormwood’s current “patient”–through subtle temptations rather than gross ones.

Screwtape writes to his nephew:

We want him to be in the maximum uncertainty, so that his mind will be filled with contradictory pictures of the future, every one of which arouses hope or fear.


Get his mind off the simple rule (“I’ve got to stay here and do so-and-so”) into a series of imaginary life lines (“If A happened—though I very much hope it won’t—I could do B—and if the worst came to the worst, I could always do C”).

All of these, Screwtape concludes, are excellent tools for distracting the human mind from what’s most important in life.

See the point? You may find yourself ensnared in that same web of excess precaution when considering whether to quit your job at the end of your early retirement journey…making you much more afraid than needful.

Mind you, I’m not saying be cavalier about the risk of post-ER financial failure, but know that the same drive, knowledge, etc., that’ll get you there will help you land on your feet if worst comes to worst. And eventually your confidence may very well increase to the point where your recovery plan becomes: “I’ll figure it out.”

Certainly mine has.

Author: ER Dude

Sick of your job? After a thirteen-year career, Early Retirement Dude fled corporate America for good. You can do it too! Visit http://EarlyRetirementDude.com or email EarlyRetirementDude@gmail.com.

6 thoughts

  1. I am not the type of person who believes every last detail needs to be in order before I hit the door. In fact, I bought Financial Samurai’s book, how to “engineer your layoff,” and had a severance talk with my boss last week. I did not want to quit and get nothing, so isntead of putting in two weeks, I told him this gig wasn’t for me. He agreed and sincerely thinks I’ll be looking to advance my career. I am not going to tell him I’m retiring because I don’t want him to think I don’t need the severance. I want as much as I can get.

    In the meantime I’ll hang out. I told my wife, I’ll either get severance or I’ll work long enough to get my pay long enough to get the equivalent of severance. I am hoping he comes back with something decent.

    1. Hi Finance Pilot,

      I think that it’s better to be retrenched than to leave on his/her accord. The best is to let the employer assume that one is in need of the job to pay the liability. If the time comes in which the employer threatened to axe the staff, the staff will have the bargaining power to ask for severance package.


  2. Good news, I’m getting 3 months full pay and benefits plus a 13.5k bonus to leave. A bunch of PTO to be paid out as well.

    My last day is July 5th. I can’t believe how crazy easy it was to get them to agree to severance for very little on my part.

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