An Independent Venture: So Long and Thanks for All The Fish

If you’ve ready some of the other posts on my blog like this one or this one, you might wonder “why didn’t you quit?”. Short answer: quitting is hard. I only have myself and two cats to support and there’s already a migraine inducing list of things to consider. I can only imagine how much more challenging it would be for someone with a spouse or children to support as well. For what it’s worth, I will go over considerations I have in mind when quitting, whether I have a job to jump to or not.

Health and Well-being


There are a few things to consider about vacation if you have any left at the time you are planning to leave.

Cashing Out: Does your company pay out any remaining vacation left that you haven’t taken? If not, then you may want to take that paid vacation time before leaving.

No Extension Policy: Your company may have a policy where you cannot extend your time working for the company by taking all your remaining vacation within some number of days of you quit date. Even when I worked at a company with this policy, it wasn’t enforced.

Health Insurance

End of Coverage Date: A lot of companies pay for their employee health insurance monthly and typically you are covered from the 1st of the month. This means that if you quit on the 1st, you are covered for the full month without being employed. Unless there’s a good reason not to, try to quit after and as close to the first as possible if you need to stay in the US after quitting.

FSA: If you have a Flexible Spending Account, you will lose all the money when you quit because your health plan will change. Need a new pair of glasses or were you considering Lasik? Use up that FSA before you leave.

HSA: If you have a Health Savings Account, you can keep it open and keep the money in it. However, you may be responsible for the monthly fees to the bank. Check those out with your HSA provider to see if you’re willing to keep those up. Alternatives for this include rolling your HSA funds into an IRA. You would need to check with your HSA provider first. If you plan to leave the Unites States, you will need to pay the penalty to withdraw all the money if you don’t plan to leave it in the states.

COBRA: When you quit you’ll get a letter about COBRA. You can enroll in continued coverage with your employer’s health plan for a limited amount of time. Usually this is expensive. Plan to research this along with your other health plan options before quitting.

Fitness and Education Benefits

If you company has fitness or education benefits like paying for a gym membership, you will not only see your membership end but you may need to pay back some money. Double check the policies to see if you need to pay money back and how much. Similarly, check to see at what point your gym membership will be cancelled. Maybe you can spend more time at the gym after you quit if it continues.

Employee Assistance Program

Many more companies are offering something called an Employee Assistance Program or EAP. This offers some small number of appointments for free with a therapist or psychologist. Feel free to pass this up but there are some therapists that specialize in life transitions and career planning. If you want to chat with someone about quitting and bounce your ideas off them, a couple of free session before actually making the change might keep you more sane during it.


Before losing contact with your physicians or other medical providers, make sure you have their contact information to retrieve records in the future. Similarly, request any necessary vaccines and proof of vaccination before losing health coverage. Also another potential way to drain that FSA money if you want a yellow fever vaccine, for example. Do also have a printed copy of your prescriptions to make it easier for any new physicians in any country to resume your medical care.

Money, Money, Money

You will have all kinds of money implications including but not limited to:

You can go very deeply into all of these so I will try to boil them down as much as I can:

  • If you received any bonuses, check to see if you need to pay them back and how much you need to pay back.
  • Have enough money to cover your living expenses in savings for at least 3 months. There are many resources online that can help you understand what goes into that number or if 3 months makes sense for you. Example.
  • If you have stocks awarded from your company, check what their vesting dates are and how much you will lose. You will lose all unvested stocks.
  • Opening new lines of credit may change if your company has an agreement with banks to provide discounts or other advantages to it’s employees. You may want to carefully plan for any new lines of credit you’ve just opened or plan to open to see if you benefit from using the company benefits.
  • Taxes! We love taxes! If you make a decent salary and get stock from your company, you deeply fear selling your stock due to the jump in your tax bracket for that year. The plus side of being unemployed? Lower income. Consider planning to sell stocks or otherwise liquidating assets during the time you are unemployed to keep your taxes low.



If you have a Green Card or a visa (not the credit card), you may not know when you will stop being allowed to work in the US. For visas, it varies based on the visa type. Check your visa type and it will specify for how long you may remain in the US before you must leave and reenter. For example, H1B – you must leave within 60 days and re-enter on a visitor visa if you want to come back without another work visa.

Green cards are more interesting. You may be abroad outside of the United States for 1 year and re-enter without needing to report your absence or lose the card. You may additionally request another year to extend your absence from the US to 2 years but any longer than that and you lose the card. If you don’t request and extension, you will lose the card after 1 year away. How do they tell when you’re away? I have no idea. You can try to game this system but the consequences are extended periods of being banned from entering the US if you lose that game.

Finally, if you have dependents on your visa, they will face similar status changes and risks as you do.


If you would like to move to another country, state, or city with your animals, make sure you have copies of their vaccines and medical records before moving. If you have young animals that are still considered babies of their species, there are different import/export laws for them. Even in other states or cities they may have different banned breed lists, animal registration policies, or spay neuter policies.

Nice to work with you; let’s stay in touch

Giving Notice

Check about your company policies around resignation. Many tech companies use “at will employment” contracts which means we can quit whenever we want. However, if you want to stay in the good books of your employer, find out what the unofficial guidelines are. If you are not able to ask anyone at work, websites like Glassdoor or Blind (if you can sift through the toxicity) discuss these topics for each company.

There is a stereotype of “2 weeks notice”. Do not assume that your company follows that. Typically you want to budget enough time to tie up loose ends for work but not enough time for them to give you more work. Further, when hearing that an employee is leaving, some managers will choose to pile on the work even harder to get the most out of them before they leave. Be ready to say no if this happens to you.

Finally, and perhaps most importantly, some companies will require you to leave immediately under company escort out of the building if you disclose you are leaving to work for a competitor. Make sure you moved your office couch out before you give your notice in that case. Make some excuse about getting it reupholstered with Pokemon fabric or something similarly question blocking.

Staying in Touch

There are a few different ways of staying in touch with people. My favorite is using LinkedIn. This allows me to give my contact information out to people and still being able to control who I accept as a contact.

Using your email address is up to you but I find that people rarely reach out that way. LinkedIn is far less personal and lacks commitment enough that people are more likely to use it. Similarly, Facebook or phone numbers are also a little too personal and you might find out about that secret crush the guy near the printers has had on you and wish he didn’t just get your phone number. If you do prefer phone and want to keep your personal number private, Google Voice numbers are another way to share numbers and maintaining control over who can reach you. They are also another way to maintain contact with those in the US if you are not going to be in any particular country after quitting.

How to do the quitting

After having gone over all these really painful planning and paperwork points, what about the actual conversation with your boss? You will need to stay tuned for another blog post on that topic!

Explanation of title.

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