top of page

The Best Time to Quit Your Job

  • Writer: Jessica
    Jessica
  • Feb 9, 2019
  • 3 min read

Updated: Nov 27, 2024

When is the best time to quit your job? Is it on a Friday, or in the middle of the week? In fact, there is a way to figure out the best time to end that relationship.

As a Financial Analyst, I have the insider secrets to benefit administration. In my day-to-day I run payroll and work closely with HR to ensure that benefits are administered correctly for tax purposes (ex: payroll deductions for dental and vision). As such, I see when benefits start and end for newly hired and terminated employees. I’ve seen handfuls of employees get put in less than optimal positions due to timing. Here are a few insider tips:


Lesson 1: Never start a job on the 1st day of the month. This is the worst thing that you can do.

Most companies start benefits on the first day of the following month. For example, if you start on January 1, your benefits would start February 1. You aren’t in that ‘following’ month until you work for at least 30 days. It may seem like a good idea for getting an even paycheck, or celebrating a work anniversary, but you are out of luck on benefits for an entire month. Further to that, most companies end benefits at the end of the current month that you work. As such, your former company would end benefits December 31, and your new company wouldn’t start benefits until February 1. You are now without insurance for an entire month! I’ve also seen some employers end everything immediately and do not carry on health insurance to the end of the month. This is a touch heartless, as the insurance has already been paid for and they would have to request a credit. But, it happens every day so always know if the job you’re about to quit is going to terminate your insurance immediately.


Lesson 2: Medical insurance is actually very important if you find yourself without insurance between jobs.

You may think that you won’t get sick in that month, but insurance makes all the difference when you think about something sudden like breaking your arm while playing sports. If you don’t have insurance, a broken arm could cost you around $2,500. Compare this with a potential month of COBRA (self-purchased temporary medical insurance) from your last job. Most employers (20+ employees) are required to offer COBRA. This allows you to keep the current medical insurance plan and just buy extra months directly from the insurance company. Although these rates are higher than what you were paying when the cost was subsidized by your employer, at least you are hedging your bets effectively. $400 per month for COBRA compared to a potential bill in the thousands is an excellent hedge that I highly recommend. Also, you get points for feeling like a responsible adult when you sign up for this type of plan. It means you’re managing your health and financials well.


Lesson 3: Don’t be afraid to ask your former employer when benefits end, and your new employer when benefits start.

It’s tempting to want to accept a new job immediately, but it is important to understand when benefits begin and what they entail. Employers can also choose to make you wait an entire 90 days before receiving benefits. Do not assume that your new employer has the same type of benefits and timing as the former. If you find yourself in a probation period without benefits, consider the cost of the COBRA in your negotiations. You could ask your potential employer for an additional $1,200 salary if you know that you need to wait 90 days, and you are intent on buying COBRA. Consider providing documentation of your COBRA policy offered by your former employer (something that you can get information about at any time) to show the exact cost that you will need to pay. Side note: if you start asking your former employer about COBRA benefits, you will be very clearly tipping them off to the fact that you are looking to depart. Try to find the COBRA information via your benefits portal or handbook to fly under the radar if that’s important.


Bottom Line: It just got more complicated to find a new job that makes you happy. Now you must consider the timing of benefits between two separate companies, and think about a health care policy named after a snake and spelled with all caps (COBRA). 🐍

 
 

Recent Posts

See All

©2024 by Jessicanomics LLC

bottom of page