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Considerations When Quitting a Job

Quitting a job can be scary for many reasons - it is hard to have this conversation with a boss, especially if you have a personal relationship. On top of that, your job was probably really comfortable if you’ve been there for a while. Now, you have to navigate new waters whether that be a job with a new company, self-employment, parenthood, or whatever drove you to make the change.


Something I’ve found that relieves my anxiety - planning! Below are some tips I’ve compiled along the way through my own journey from a couple employments into self-employment.


What are you doing it for?


I would hope this question is answered before you take action, but I think many people view quitting as walking into your boss’s office and throwing your laptop through their window. But, in my experience, that has never been the case.


There are many reasons to leave; compensation, getting burnt out, disliking the culture, no room for growth, better opportunity became available, or something as simple as you're no longer enjoying the work.


Reflecting on why you are doing it is an important step, especially if the change is going to be drastic. Maybe you’re going to take a huge pay cut to start a business or change industries - remember how you felt (or write it down!) during this time so if you have that feeling of “what have I done?”, you can remember the reasons why you did it, and how you felt when making this decision.


Reflecting on why you are doing it will help you put into perspective the “risk” of the change, and why that risk is worth it to you.


Formulate what’s next


Now that you’ve reflected on what is making you leave, if it is an issue with your current job, what have you done to correct it? Have you shared these concerns with a manager and nothing has changed, or have you kept quiet along the way?


Many times managers don’t even know you are having issues or concerns. Don’t let fear of this conversation cause you to make a rash decision like quitting. Have the conversation with them and see if they can help improve the issue if you think that is the best route (as opposed to quitting).


This may not be applicable if you are leaving for outside reasons, but it is definitely a worthwhile step to improve your current situation if you would prefer to stay.


There is various advice on the internet about having a job lined up before leaving, but this is totally individual for each person. If you have the financial means to take a break and you want to, I think that is a great idea. A slight gap in employment likely won’t ruin your financial standing, and it may even be a positive investment in your happiness by giving you time to reflect on what went wrong, and what you want to happen next.


But I must caution - think through a backup plan. A break is great until it is time to get a job and there is a bad job market or a slow hiring process. Make sure you have a plan for this situation and know when you need to start taking action towards what is next.


Financially, what steps should you take?


This can be, and is, a whole blog post on its own. You can find my blog labeled Financial Decisions of Leaving a Job.


In a shorter form, my recommendation is to think through the benefits you are giving up by leaving the position. This can either be replaced with a new job if you have one lined up, or you’ll have to plan how you’ll replace the benefits yourself. A very important benefit is health insurance (and maybe even life insurance) and figuring out how you are going to continue your coverage.


Another point is if you have a bonus coming up or the vesting of compensation (equity compensation or 401(k) contributions), it may be worthwhile to wait for that to happen. Additionally, if you recently received a bonus or another form of compensation that has a claw back provision, it may be worthwhile to wait for the claw back timeline to expire. Make sure you know the timing of these things and remain eligible to receive (or keep) them before (or upon) leaving.


Many companies will purposely structure compensation in this way, known as Golden Handcuffs - for example, they may have compensation that vests every 3-6 months to keep you employed with them. It may make sense to wait for this compensation to vest before quitting if the vesting period is very close, but it may not make sense to stay employed over the long-term for this - I just point out that you should make sure you know what you are giving up when you leave so there are no surprises!


One last point on this is if you are planning on lining a job up before leaving, these Golden Handcuffs can play to your advantage when negotiating for a new job. You can argue that the new position should make you whole for giving up that unvested or unpaid compensation to join their company.


Be respectful, but honest


I don’t mean brutally honest… if the reason you’re leaving is truly because you hate your boss, maybe just keep that one to yourself.


Hopefully at this point you’ve reflected why you want to leave your position and you’ll be able to explain why it is important to you to make this step. You should be honest about this for yourself, and for your team as they can improve from the valuable feedback you give them. It keeps a respectful relationship and they’ll remember that you were open to helping them improve.


This helps you to stay on good terms, which is the goal every time you leave a position. You may rely on some of these people in the future for references, advice, or even a job again! Burning that bridge will only hurt you, in exchange for the very short rush of dopamine after giving your boss a piece of your mind.


The standard timeline is a two week notice, and I generally recommend this. If you are open to working longer and want to offer that to your employer, I think that is valid. But when your are quitting your job, it is time to focus on yourself, so make sure you are doing what is best for you and not your employer.


You should tell the person that you report to first and foremost, but I’ve always found benefit in pulling all the people I’ve worked with aside and telling them myself. It is not always the easiest conversation, but it is nice to have a candid conversation with them and see if there is anything I can do for them. Some things I’ve done is give feedback during my exit interview that could potentially make their lives easier, as well as just doing a little extra work to make the transition as smooth as possible for the next employee. You never know when you will need their help in the future!


This leaves my final point: work hard in your last two weeks. This is not a break for you to relax. You gave them two weeks to help with the transition for the next person, so make sure you are holding your side of the bargain. I’m confident to say that their last impression of you will be negative if you slack off on your final days.