Finding The Exit, and Leaving On Your Own Terms

How to Quit Your Job on Your Own Terms

You’ve had it! You’re not going to take it one more day! Tomorrow you’re going to walk into work and quit your job!

True… you don’t have another job yet, but you don’t think that will really be much of a problem. Everyone says it’s an employee market because companies can’t find enough people to fill their openings. And the satisfaction of walking out…the look on the boss’ face… You just want to get out!

Wait a minute. Don’t just quit your job! There’s a lot more you may need to think about.

A Tough Job, Well Done

If you are considering leaving your employer, think carefully about how you will quit your job. There’s money, options, and your reputation at stake.

I’m in the business of helping employees transition from one job to the next. At my company, we see the successful warriors of business as well as the walking wounded. Our forte is career coaching for corporate executives and career outplacement for separating employees.

In my role as a career coach, I’ve seen it all. I’ve seen business executives who’ve done a great job of parting company with a troublesome employer – garnering transition pay, good references, extended health insurance benefits, career transition services, company car purchases, country club membership conversions, and a whole host of tangible and intangible benefits. I’ve also seen corporate employees who have gained the satisfaction of quitting in anger without notice and exiting their place of employment with nothing more than a final paycheck and a dubious reference.

What can be negotiated when you quit your job?

Serious conversation

Not everything at every company is negotiable. However, the following is a list of those things that may be negotiated when you quit your job. Consider what you might ask for before you leave.

Unemployment Benefits

Will the company contest your claims for unemployment compensation? It’s better for you if they don’t. Ask about the process, and ask for a “no contest.”

Severance Pay

Can you receive company policy severance pay even though you’ve initiated the separation? If the circumstances of your employment have been tough, you might receive a “yes.”

Reimbursement Educational Tuition

Will you still be attending classes when you quit your job? Will your employer pay at the end of the semester, even though you’re no longer there? Did you begin a class and file for tuition reimbursement with the company? Maybe they will consider an educational leave for you…and tuition reimbursement at the end of the semester. If you haven’t started classes and your goal is to return to school after leaving the company, they just might consider it as well.

Changing Employment Status

Might you ask to move from an active to inactive employee status while you rethink your position with the company? Could you move from active status to leave-of-absence status? Have you considered moving to a contractor position? Rather than outright quit your job, would you consider an on-call or “as-needed arrangement?

Health Insurance

Health insurance is especially important to consider when you quit your job, and I’m sure you’ve already had anxiety or apprehension about it. Can health insurance be extended beyond your last day at work? How long can you extend it if you pay in advance? What other plans are in place to assist departing employees?

Vacation Pay

What happens if you have already used vacation days that weren’t really due to you? Will they forgive it? What happens to any unused vacation time on your last day? Or should you use up your paid vacation days prior to quitting? Maybe a vacation could help with your feelings about leaving the company!

Handling References When You Quit Your Job

What will your employer say to whom, and what is the policy regarding discussing a previous employee’s departure? Can you discuss how you would like your references to be handled with a designated person?

Profit Sharing, Incentives, and an Annual Bonus

Do you have these lucrative benefits at your company? Can these be prorated when you quit your job, or can you receive the total share? Read your plan documents ahead of time…you will know more than most others if you do.


Does the company have a history of providing outplacement or career transition services to departing employees? Even if they don’t, will they provide it for you? Can you select your own career coach? Chemistry and deep expertise matter here.

What to Negotiate When You Quit Your Job

Office Furniture or Equipment

Can you buy your custom designed, specially ordered furniture from the company? Do you even want to? Who will pay to have it moved?

Tools, Hardware, Software, Phone, or Other Personal Technology Devices

Does the company allow for the purchase of these items, or will they gift you the mobile phone or printer you use for work? Have you transferred your personal information out of these devices? Make sure you do not transfer or take company-owned material, lists, or documents.

Company Car

Do you want to buy out the lease when you quit your job? Ask about it. Do you have any unreimbursed expenses for this car? Submit the expense request now.


If you are fortunate enough to have a club as part of your benefits package, are there any conversion or extension privileges for your dining club or country club? Detail who will pay the current month or quarter dues.


quitting your job, packing up your desk

Don’t leave anything on the table here. Speak to the company pension expert, and ask for the present value of your pension. Are you bridged or hooked up from any prior interrupted or predecessor employment? Ask about company matches and payouts. Can you negotiate the next payout into your separation package?


Do you hold any outstanding corporate loans? Negotiate the payouts, or ask about incremental loan forgiveness or an extended payback schedule.

Expense Request When You Quit Your Job

Many people carry company expenses on their credit cards and periodically request personal reimbursement, and most of us are behind in asking for the funds due to them. Make sure you have detailed all your legitimate reimbursable expenses and submitted the request ahead of your declaration that you are leaving.


“Thank yous,” and courtesy calls should be a part of your departure. This can be done in notes and email or in person. Thank people broadly. Remember to keep negative emotions in check when you quit your job. It doesn’t serve you to leave anger and negative words on the doorstep when you exit the building.

Tools for Planning Ahead

Know Your Worth - Purpose Driven Career Journal
Know Your Worth: Purpose Driven Career Journal, $19.99
what color is your parachute
What Color Is Your Parachute? 2022: Your Guide to a Lifetime of Meaningful Work and Career Success, $17.99
Own Your Career Own Your Life
Own Your Career Own Your Life, $14.99
The Career Coaching Handbook
The Career Coaching Handbook, $38.45
30 Day Career Clarity Challenge Journal
30-Day Career Clarity Challenge Journal, $4.06
Second Acts - Creating the Life You Really Want, Building the Career You Truly Desire
Second Acts: Creating the Life You Really Want, Building the Career You Truly Desire, $14.99

Read More:

What to Do When You Absolutely HAVE to Get a Job

3 Job Interview Tips to Use When Facing a Younger Interviewer

How to Age-Proof Your Job Hunt


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