Everyone has heard the standard advice that you should never quit a job until you have another one lined up. But not everyone agrees with it.

Entrepreneur and author Tess Vigeland, for instance, has urged "everyone who's ever dreamed of setting fire to expense reports or tossing a uniform in the dumpster to take a flying leap in the year ahead." Sometimes the only way you can figure out your next move is to give yourself some job-free time to think and explore, she argues.

But when I highlighted Vigeland's essay here on Inc.com, there was plenty of pushback on social media. Sounds nice, many folks responded, but I can't pay my mortgage in insight and experience. Vigeland's advice is lovely, but it's just not practical.

It seemed like skeptics and fans of the fearless leap could never be reconciled. But then I came across the work of Caroline Ceniza-Levine. In a Forbes post, the entrepreneur and career-change expert walks a middle way. Quitting when you don't have a fallback plan is a good idea only in a few specific situations, she asserts. In other words, Vigeland is only correct if one of the following circumstances apply to you.

1. Do you have no autonomy over your schedule?

Let's be honest, if you can never get off early or come in late to go to an interview because of either the nature or your work or your boss's police-state-level surveillance, you're never going to find a better gig while working. Quitting to look for a new job is probably the only way to avoid being stuck in micromanagement hell forever.

2. Is everyone going to know you're job hunting anyway?

Do you work in such a small niche or tight community that there is no way you're going to be able to pull off an under-the-radar job hunt? Then admit as much to yourself and make a clean break with your current work. That will free you to find a new position without resorting to cloak-and-dagger tactics.  

3. Is your current gig so soul-sucking it's killing your motivation?

This final category probably applies to the most people by far. Job hunting (or building your own business) takes energy, optimism, and resilience. If your current job is completely sapping you of all three, how can you expect to make any progress in building a better career?

Or maybe it's just be that you're completely baffled as to what you'd actually like to do next  because your current gig takes up all your time and energy. In that case, get out that parachute and make some space in your life for some soul-searching and experimentation.

A pre-quitting checklist

Of course, you can't just answer yes to any of these questions and then march immediately into your boss's office, resignation in hand. Ceniza-Levine stresses it's only OK to bail on your current gig after you've make sensible efforts to try and improve the situation and prepare for your coming period of unemployment.

Could a chat with your boss about rejigging your responsibilities help, or would a lateral move to a more suitable position in the company be doable? Do you have issues that HR could sort out? Is there a mentor who might be able to help you massage your current work into something more in line with your goals?

Only if the answer to these questions is no and one of the above three situations applies, should you take the leap. But before you do, run the numbers and make sure you have enough saved to cover three months' worth of expenses and have some idea of how you'll use your newfound freedom to advance your search for a better career.

Checked all those boxes? Great--then it's time to take the plunge, because sometimes a happier work life demands a little bravery.

Published on: Jan 31, 2019
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.