The Overlooked Factors of Quitting a 9–5

J.R.
6 min readApr 15, 2021
Make a plan before quitting your 9–5.
Photo by Nastuh Abootalebi on Unsplash

If you’re looking to quit your 9–5 (or 9-much-later-than-5), go for it, whatever the reason. Just don’t do it like I did.

I didn’t storm out of my office, middle-fingers akimbo, cursing out anyone I ever worked with — but I also didn’t plan for the adjustment in lifestyle, and it caused a good deal of stress.

So, without further ado, here’s some quick tips on how to quit your 9–5 job and adjust to the new lifestyle.

Before Submitting Your Two Weeks Notice

Whatever your reason for quitting, try to use up the advantages that your company provides before stepping out.

When I decided to quit, I was so fixated on quitting that I neglected utilizing some obvious luxuries that someone who knows they’re leaving has, such as PTO, contributions/benefits, and more.

Let’s start with your PTO.

Paid Time Off (PTO)

Burn it up and leave nothing left.

I left 9 days of PTO on the table for dumb reasons:

  1. I was concerned that taking excessive PTO immediately before quitting would be seen as rude/inconsiderate.
  2. I was so eager to quit that I didn’t even consider the upsides of having even one more paycheck

If you agree with my logic for reason #1, I’ll tell you the same thing I wish I had told myself at the time — no one cares, and you won’t regret it.

Seriously. It’s nice of you to not want to rub your co-workers the wrong way, but the chances of anyone being offended by your exit strategy? Slim to none.

If you’re about to quit your job, you really need to embrace the idea of living on your terms, not someone else’s.

Also, the extra time off will give you a glimpse into what life is like outside of a 9–5.

As for reason #2, it won’t kill you to take whatever day you planned on submitting your two weeks notice, and push it two weeks back.

You could always benefit from one more paycheck, and if you’ve worked for a while, what’s two more weeks?

So, when you’re certain you’re going to leave, do the following:

  • Pick the date you’ll submit your two weeks notice, and push it back another two weeks (but no more than two weeks!)
  • Prior to submitting your two weeks, burn up your PTO. Either take large swaths of time off at once, or maybe give yourself a series of consecutive long weekends — enjoy!

With your PTO properly planned, you should consider making adjustments to your benefits contributions.

Adjusting Your Benefits

Benefits and contributions are great, but if you’re quitting soon, you may want to rethink them.

Me? I kept contributing to my 401k/Roth until the end. That wasn’t the smartest decision.

I should have realized that a few hundred more bucks for someone who’s about to quit is much more valuable now than at retirement.

I was going from 60–0. From consistent paycheck to nothing. You’d think I’d adjust my contributions to zero, gathering every precious dollar I had, but no.

My rent was $1,245 at the time, even though I had to put up a temporary wall to make my bedroom (Manhattan). Money was about to be tight.

So, while contributions and benefits are amazing, make sure you’re not putting funds away when they may be much more necessary in the coming months.

Ok, so after all that, you’ve probably submitted your two weeks notice. Do your due diligence during those last two weeks at work.

Before you know it, you’ll be at your last day at the office. Say your good-byes, and head into the weekend like everyone else.

Unlike everyone else, though, you won’t be going back to work on Monday.

The Monday After Your Last Day

For me, my first weekend without a job didn’t provide any new perspective. After all, the weekend was part of the usual routine.

On Monday, things started to sink in — perhaps not as much as it should have though (more on that in a bit).

My roommates went to work. My girlfriend went to work. My former colleagues went to work. The corporate world was back at work.

Then there was me. No significant plan other than to apply for a handful of jobs every day — full-time, freelance, or internships (I quit so I could fully focus on changing career paths).

As I quickly learned (literally during my first Monday off), I could have benefitted from more stringent plan, as well as some limitations to what I should and shouldn’t do.

Set Limitations for Yourself

On my first Monday off, I got a text from a college friend. He was visiting New York on vacation and wanted to meet up for drinks.

I met him out, and told him how I just had my last day of work on Friday.

“Wait…” he said. “…you don’t have to work tomorrow?!”

We got another round. Then another.

Long story short, on my first non-work day, I end up bar-hopping.

Not ideal for someone who won’t be getting a paycheck in the foreseeable future.

This one should be obvious, but definitely avoid bar hopping when you’re unemployed — it’s expensive and very counter-productive.

Before quitting day, take a moment to really consider what your new lifestyle will entail. Typically, you’ll have a lot more time and way less income.

The issue is, everyone else you know isn’t in your boat, so they’re living life as usual.

Setting limitations for yourself helps prevent you from keeping up with anyone who still has their job.

You don’t have to quit fun cold-turkey, but make a plan to go out way less than you used to.

Ok, so I was irresponsible on day one. What about day five, or twenty, or more?

Staying Consistent & Exploring Your Options

Without a set schedule, it can be hard to maintain consistent effort towards your not-full-time lifestyle.

Depending on your reason for quitting, your schedule can be very concrete (travel plans booked), or very loose (work on a personal project, get freelance work, etc).

If you’re in the loose plans category, it can be hard to stay consistent.

Again, I was trying to build up experience as a developer in order to get a full-time offer. So for me, it meant job applications, scouring the web for freelance work, and working on my coding portfolio.

However, I did all of this from my laptop in my bedroom. Which brought two problems:

  1. I was ignoring the countless job fairs, events, and overall networking opportunities available to me in NYC
  2. My work device was also my Netflix device, so I watched a lot of Mad Men

Before quitting, I reveled in the idea of having all day to focus on honing my skills and sending out job applications. When the time came, I wasn’t putting in nearly as much effort as I could have been.

Whatever your plan my be, take some time to go to networking events based on your interests. I used sites like Meetup to go to tech events and job fairs — it has categories for all types of interests.

Networking events like those are the key to getting past many initial barriers you may be facing. You’ll often meet people with the experience you need to accomplish your new goals.

One of these events per week proved more effective than days of aimless job applications in my apartment.

Recap: How To Quit Your Job

Whatever your reason for leaving the 9–5 life (permanently or temporarily), I strongly encourage you to follow through. Your life will almost certainly be more fulfilling as a result.

That being said, I made some pretty avoidable mistakes. So to recap, if you’re about to quit your job, make sure to do the following:

  • Burn up your PTO, then submit your two weeks notice
  • Add two weeks to whenever you planned on submitted your notice to collect one more paycheck — but only do this once!
  • Adjust your benefits/contributions, you may need the money more shortly than at retirement
  • Set limitations on recreational spending. You’re income is going to be taking a hit, so don’t live like you did when employed

You’re about to take an exciting step in your life. It was a very fulfilling experience for me, and the ups and downs taught me a lot. Overall, I hope you take the leap, but with a little more sense than I did!

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