Four Things To Do Before Quitting Your Job

By: Every Day By The Lake

Have you ever thought about quitting your job?  Have you imagined what it would be like if that element of your life was no longer there?  How would you use all of that extra time?

That very thing had been on my mind for as long as I could remember.

I was desperately yearning to live life in another way– to have freedom over my time and my lifestyle.  I knew that I had to leave traditional 9-5 employment behind me to achieve that.

I knew that I could not stand to stay on that path for another 30+ years.

But I also knew that I could not quit my job recklessly.  I had a family to take care of.  I had a mortgage and student loans to pay.

I needed an exit plan that would satisfy my soul without compromising my obligations.

If you’re planning to walk a different path, to make radical changes to your life, then you need a plan, too.

I’d like to offer some general considerations as you craft your strategy.  The below may seem obvious– but if you’re desperate like I have been, or impulsive, like I can be, these items can be very grounding.

You need to make life moves based on reality or at least strong probability– and not on fantasies or complete whims– especially if others are counting on you.

Here are Four Things You Need To Do Before Quitting Your Job:

1. Check Your Finances.

As much as it can be a drag, no matter what your circumstances are, you need money to fund your life.  Maybe you need a little cash or maybe you need a whole lot.

Think about the following:  What are your regular monthly expenses?  What are some irregular expenses that you can anticipate?  How much do you have saved?

If you quit your full-time job, do you have other sources of income that can help preserve your savings?

My process: I created a list of my expenses, both monthly and irregular.  I checked all of my cash reserves.  To prolong my time away from cubicle life (and to sleep better at night), I secured some part-time, flexible schedule, remote work.

I determined that my part-time income, supplemented by my savings, would enable me to be free for more than a year.

A year is not forever.  A year will go by quickly.  But a year gives me time to cultivate other income streams so that I (hopefully) never have to go back to full-time corporate life again.

(Note: As you can see from the Excel list above, I have excluded health insurance and cable/internet from the expense column.  I am winging it and have opted to not purchase a health insurance policy.  (This is not something that I necessarily encourage others to do.  It’s something I feel comfortable with, for the time being, having considered the risks.)  The cable/internet is covered by someone else in my household.  Having other household members definitely lightens my financial load as some expenses are shared among all of us. The mortgage and student loans are in my name.)

2. Check Your Goals.

This type of life change is different from a vacation.  For one, it’s for a much longer time period (maybe indefinite if you can work it!).  It’s also perhaps the opportunity of a lifetime to work on important goals.

Yes, relax.  Yes, nap.  But learn to play guitar, grow your own food, speak Spanish or use WordPress.  Finish your degree.  Start your business.  Anything.  Really.

Just make sure you know what you want to accomplish during your time away from full-time work.

And, if your goal really is just to relax because that’s what you need more than anything, then do that.

Just please be honest with yourself about your dreams and make sure they’re clear before you turn in your notice to your boss.

My process:  I thought carefully about what I wanted to achieve.

I have been at a standstill with my doctorate degree for more than a year.  I resolved to complete the degree during this semi-retirement period.

While I was no longer sure the degree meant the same thing as it did when I started the program, it was still very important to finish what I started.  I had committed too many resources to let it slip by undone.

I also resolved, as I mentioned above, to find a way to never return to full-time corporate life.  I promised myself that I would work hard to secure those other income streams.

Most importantly, I planned to make life enjoyment a priority.

After all, that is the ultimate point of this journey and, really, the ultimate point of life itself.

I was going to spend more time with loved ones, nap on a Tuesday afternoon and plant more flowers in my backyard.

I committed to starting the journey with a real direction and I know that it will help me if I begin to go adrift.

3. Check Your Family.

Your family is probably one of the main reasons that you are planning to re-design your life.

The decision to rearrange your life impacts everyone in your home.  They may be scared that you’re cutting off an important income stream for the household.  They may be skeptical of what you’re trying to accomplish.  They may be wondering what it will be like to have you around more.

They have to understand how life will change for them.

If you have really thought this and can show them you have a solid plan for your finances and how you’re going to spend your time, you should get their buy-in with no issues.  But they deserve to know what you’re thinking about before you go ahead and actually do it.

My process:  I let my family know what I was planning to do.  I was very fortunate.  At worst, I was met with some concern over the household’s financial security.  My 70-year-old mother in law offered to get a job to help out.  I told her that we were quite a long way away from that being necessary!

4. Check Your Job.

Say what?!

Isn’t this supposed to be about getting away from full-time work?  Yes– it definitely is.  But the beauty is that you can decide how long you want to be away.

If you think you only need 6 months to recharge and complete a pet project, then perhaps a sabbatical is a great option.  Depending on your tenure at the organization and their leave policies, you may be able to take your time away and then return to the same job.

This is definitely something to consider and, if available to you, could be very reassuring as you transition into the time off.

My process:  A few months ago, I tested the waters with my boss.  I pretty much knew that my job (HR Generalist at a manufacturing facility) did not lend itself well to working remotely.  I also was pretty sure that the company did not offer a sabbatical option.  (I was right).

But I planted the seed– just in case.

Not having a sabbatical option was probably a great thing for me.  It forced me to commit to this idea of really separating from corporate life.

Don’t Over Do It…

One caveat and perhaps contradictory to the above:  don’t over plan.

That’s a real thing.  That’s when you attempt to plan for every contingency (impossible).

That’s when you promise yourself you will make the leap when you have $XX more in the bank.  And then, you guessed it, when you cross that threshold you set a new one, further delaying your dream.

I get it.  It’s scary.  Logically, I know that I’m fine for now and for the foreseeable future.

That still doesn’t stop me from worrying about the “what if”s or the “what’s to come”s.  But they are very paralyzing.  If you succumb to them, you will be living with the “what happened”s.

Time will have lapped you and you will have missed your window to actually act.

After reading the Four Hour Work Week, I realized that Tim Ferris had a point.

Whenever faced with a paralyzing decision, you should ask yourself—what’s the worst that could happen?  What’s the real probability of that happening AND if it should come to pass, am I strong enough to deal with it?

As Henry David Thoreau so wisely told us “Go confidently in the direction of your dreams.  Live the life you’ve imagined.”

Are you ready to heed his words?

I am!

The above are the major points I considered before ‘making the leap.’  Preparing for a major life change like this is intensely personal and should be customized based on individual circumstances.  What would you add to this list?

Republished with the permission of Every Day By The Lake.

8 replies on “Four Things To Do Before Quitting Your Job”

“I am winging it and have opted to not purchase a health insurance policy.” stopped me in my tracks!
Reckless and possibly ruinous for you and your family.
My sister took a risk this year to buy catastrophic health insurance to save money when her premiums for traditional insurance were going to double. And then in January, she was diagnosed with breast cancer. Thankfully we were able to switch her to a traditional policy effective March 1. But she still incurred $125,000 of costs for diagnosis and her first chemo treatment in two months. And I had to put my life on hold to help her navigate the insurance nightmare as she was feeling the worst effects of chemo. And, yes a lawyer got involved. We just learned we won the first battle, but holding our breaths to see if they actually start paying her claims or if there is another battle to be fought.
So we are still waiting to where between $30,000 and $150,000 her health care costs this year will land — while she recovers from surgery and possibly undergoes radiation. (If she had been stuck with the short-term catastrophic, we might have been facing a $1 million liability!)


First and foremost, I’m sorry to hear your sister is going through this (and you, too!). I hope that she is responding well to treatment and is feeling better soon.

Based on your experience, I completely understand your viewpoint.

Experiencing a health crisis while uninsured definitely weighs on my mind and I don’t intend to go uninsured forever. I am gradually increasing my income and will buy a plan in the near term– maybe on the Marketplace at this upcoming open enrollment.

I know what I did was a gamble (still is), but there were factors that made it feel personally impossible to remain in my then current employment situation (no fault of the company). After leaving, I realized that I probably should have flown the coop even sooner. At the cost of a COBRA plan, I crossed my fingers for several months and here we are.

As I mentioned in my post, I certainly don’t encourage others to do this as there is significant risk involved.

Again, my best wishes for you and your sister.


I have quit several jobs in my career. (And I was laid off a few times too.)

In my younger working years I certainly would have never quit without something else lined up. I was in terror of not having a job. I grew in an atmosphere that “you need a job to survive.” It was no surprise, my parents had lived through the Depression.

However as I got closer to the end of my career, I began to have less and less patience for inane companies and their inane policies. If I wasn’t comfortable, why bother? I was still being recruited into my sixties. So, if I didn’t like something I would leave. My opinion: “Another job will come along, it always does!” If we are not in a Depression or a Recession, things can change. After quitting, I was employed again within six weeks.

All the fear I grew up learning about was wasted time.

Thanks, Smile! I agree– fear often leads to wasted time– but! It sounds like you’re not operating from that place anymore. Kudos!

Leave a Reply

Your email address will not be published. Required fields are marked *