original cynk

After leaving my last employer three times over the prior five years (two voluntarily, one via a layoff), I picked up a few tips in terms of “how to leave” with the best preparation for your next step. These are rather specific, but I believe they work for Silicon Valley companies in California, and they may also work for other companies in other industries in other states (abroad is a whole different story). I mostly learned these tips from the information packet I got when I was laid off (which I did not get when I resigned), and others come from friends’ tips and my own experience. Here they are:

• COBRA: This is a federal program to make sure recently departed employees can continue to get health coverage. Unfortunately, this tends to be rather pricey (~$400/month if you had a decent plan at the old company, and that’s not including dental or vision). One good thing is that you usually have up to 90 days to enroll, so if you know you’ll be starting a new job in that time frame, you can hold onto the enrollment docs and retroactively file if you end up in the ER- you’ll have to pay the back fees, but it’s better than paying out of pocket.
• Health insurance: Generally, companies pay for employees’ healthcare a month at a time, usually on the 1st of a month. So if you quit on the 1st, you’re covered for 30-31 more days. This is great if you want to take time off between jobs. You can also use accrued vacation time to make the bridge if you want to leave earlier.
• Health FlexSpend: Companies must pay your full elected FSA amount to the government at the beginning of the fiscal year, then the rest of the year, you pay back the company (this is why it’s “lost” when you don’t spend it). So, if you use up that whole amount on the 1st day of the fiscal year and then you leave the next day, the company can’t collect the rest of the amount from you. If you know you’re leaving around the time of benefit elections, you can max this out and not have to contribute much towards it, but you will need to make the reimbursable purchases before your last day (such as doctor fees, contacts, prescription copays, etc). However, the government is getting much more strict about what you can reimburse. In other words, you could buy several pairs of crazy expensive eye glasses in your waning days, but otherwise, there may not be much point here.
• Vacation: Depending on how your company does holidays, try not to leave your job in December- the holidays are basically one big paycheck that you could be leaving on the table. In any case, you’ll get paid out for unused vacation time when you leave.
• 401k: Your money will stay in your 401k after you leave, and it’ll keep accruing value. Some 401k plans charge fees to “manage”, but you’re fine leaving it there for awhile. Eventually, you may want to move the money over to an IRA in order to have more control over how the investment is allocated. But no need to rush. One thing to try while you’re still at the company is that if your company matches your contributions, max out your annual contributions to get as much match as you can.
• Bonuses: If you want your bonus, don’t tell a soul you’re thinking of leaving until it’s actually in your bank account. There’s no way around this. ’nuff said.
• Options: Most option programs will give you some amount of time after you leave to exercise your options. However, if they haven’t vested before you leave, they’re gone. Check the timing of your option grants- if they vest monthly or quarterly, you may want to hang on or use vacation days to stay on the payroll until they vest.
• ESPP: The “Employee Stock Purchase Program” will most likely refund any contributions you made towards this, no more and no less, on your final paycheck. Once you have the stock, it’s yours to keep well after your departure. The key timeline here is whether you can hang on until the next purchase wave and utilize the discount.
• Income tax forms: Chances are, with all of these sorts of investments flying around, you’ll need lots of forms for your tax returns the next year. Track down your company’s finance contacts before leaving so when your accountant requests, for instance, that 3922 (for ESPP), you’ll know who to ask.
• Unemployment: You’re only eligible for unemployment in California if you’re laid off or fired. Firing exposes the company to liability; laying off prohibits the company from backfilling for a year. In other words, if you’re thinking of voluntarily leaving (i.e. your company likes you plus won’t be downsizing anytime soon), don’t expect to get unemployment.
• Exit interview: This is a weird procedure companies do in order to supposedly correct their wrongs so others won’t leave. However, most likely, what you say won’t have any effect, and the paperwork will last. So, don’t burn bridges in case you return. It’s tempting to use the opportunity to vent, but be constructive about it.
• Leaving itself: I left the hardest one for last. Leaving a company is a lot like breaking up- there’s no good way to do so that won’t hurt someone’s feelings. I believe the most respectful way to depart is to give enough time to transition your projects to your coworkers that works with your schedule (and the tips above), but that’s about it. Once it’s known you’re leaving, it’s hard to do more than transition because you have an expiration date. So accept this, and get out of the way so your now-ex-coworkers can move on themselves.

And a quick note for those left behind at the old company: the key thing to realize is the strength of the non-compete clause. This means the departed employee cannot recruit you for 9-18 months after their departure. Of course, you can still be friends and the ex-coworker can reach out to simply hang out. However, don’t be surprised if there’s awkwardness around asking how the new job is, if the new company is hiring, or even where they plan to go when they haven’t left yet (which could be construed as recruiting). The key thing is that your ex-coworker’s silence if you ask for help applying at the new company is not something you should take personally- they probably secretly want you to join, and they don’t want the new company to get sued in case you do.