I'm a programmer working for a startup in San Francisco. I go through pretty bad depressive phases during the winter (it is a medical condition).

It's often difficult to get out of bed, let alone actually be productive at work. My depression also seems to be linked to the weather and amount of sunlight (I feel better when I'm exposed to more sunlight).

I have let my employer know about my condition, and have touched on the topic of being able to work remotely from warmer places (ex: it would be summer in New Zealand). However, my boss and HR said that if they let me work remotely, then they would have to let everyone work remotely.

There are already a handful of people working remotely, but they negotiated the deal before joining the company, and are paid much less. I also talked to my Team Lead, and he is totally fine with me working remotely (my work, programming, doesn't require me to be on site or even interact with others too much).

I have considered quitting my job and just doing freelance work, but that would be a last resort. I've also set a deadline - August 1. If I cannot convince my boss by then, I'll quit.

How can I frame the conversation with my boss most effectively so I can work remotely?

I am not sure what would an employer be more likely to approve: work remotely, work part-time or take a Sabbatical each time I go through a depression, nor what would be an acceptable amount of time to ask for...

I'm willing to take a major pay cut. I only use 20% of my salary. Especially if I'm going to be living remotely instead of SF, I won't need most of it. I was thinking of using my salary as a bargaining chip (half my salary in exchange for this privilege). Do I have any other bargaining chips do I have in my favor, or points I can bring up to help my case?

  • yes, it's medical. I actually took a medical leave early in the year for 2 months. my employer wasn't very happy/supportive of it. And yes, my employer has documentation from my doctor
    – Toli
    Nov 28, 2018 at 18:58
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    I am MUCH less productive in a depressive phase. I would say borderline useless. I have noticed though when I go to a warmer climate (ex: I was in LV for a month during a depression) my productivity definitely goes up. How should I get this point across to my boss?
    – Toli
    Nov 28, 2018 at 19:16
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    @JanDorniak good point about time zones. I was also thinking of joining Wifi Tribe. They mostly do Latin America. And yeah already tried D3, lamps, etc I didn't mention anything beforehand. I'd imagine it's much harder to get hired if mentioning something like that beforehand.
    – Toli
    Nov 28, 2018 at 20:19
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    Have you discussed light boxes with your doctors? If your depression is strongly linked to sunlight, that might help without requiring you to move. Nov 28, 2018 at 22:45
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    Have you considered Phoenix? It is far enough south to have quite long days even in winter, and because of its desert climate the sun will rarely be blocked by clouds. It is 2.5 hours from San Francisco, with many flights during the day, so you could get to meetings on relatively short notice. It is only one timezone from San Fransisco, so you could work during the daytime. Your employer would not have to deal with international employment complications. Nov 29, 2018 at 0:58

3 Answers 3


if they let me work remotely, then they would have to let everyone work remotely.

This is basically equivalent of saying "lol no" to your request. You gave your reasons and your employer could not care less. I would not suggest taking a pay cut in return of working remotely, it will not help you and if anything, make you seem desperate.

I would look into jobs with remote options instead of trying to convince the current employer to allow remote. They are highly unlikely to budge.

  • you are probably right. Which is why I set the August deadline to basically go freelance. But until then, even if there is a slight chance I could convince them it's worth trying. just not sure what angle I should take "Let's try to work something out" or "I'll quit if we don't work something out"
    – Toli
    Nov 28, 2018 at 20:21
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    You already provided them with medical notes and suggested it would be better for your productivity. That was pretty much the only angle you could take to work something out together.
    – Layman
    Nov 28, 2018 at 20:24
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    @Toli to sum it up: start looking for a remote (or part remote) job WELL BEFORE your Aug 1 deadline and hopefully you find one, they're out there, but the competition's high.
    – RandomUs1r
    Nov 29, 2018 at 22:33

Talked to my boss yesterday and framed my conversation as:

I am not sure how to go about this conversation, but as you might know, I have pretty bad depression during the winters. And I learned that the amount of sunlight greatly affects my productivity. I talked to [Team Lead] and [HR person] and we discussed the possibility of working remotely, like [Person 1], [Person 2], [Person 3] and a few others in the company. I realize that they took a substantial pay cut which I am also willing to do. There is a program called WifiTribe (similar to the one [Coworker] went on before he joined), which allows me to work from Latin America which is in the same time zone and has a community of digital nomads to create a work atmosphere and deal with the challenges of working remotely. I've set a deadline for August to pursue this path, as my mental health is very important to me. I have also discussed with [Team Lead] a list of projects that don't require a lot of contact with the rest of the team and can be done alone.

And my boss said that we could give it a shot by working from home during the spring/summer (when I have my hypomanic/productive phases) so that I can show the company that I am productive even when WFH (added bonus: I really shouldn't be around too many people in manic phases as I tend to do/say stupid things). And if all goes well I can work remotely the following winter. So guess that worked out better than I thought :)

I hope this helps anyone in a somewhat similar situation. These conversations aren't very pleasant to have, but I guess if you're direct and firm about your priorities, sometimes they work out.

  • Be wary that your condition is likely to continue abroad if your seasonal disorder in fact hides a bipolar personality disorder and you lack medication for it. Congratulation for negociations though
    – Diane M
    Nov 30, 2018 at 23:36
  • That is true. But I rather be miserable on a beach than miserable in my apartment. You do bring up a good point about the medication. Not sure how that will work abroad.
    – Toli
    Nov 30, 2018 at 23:46

IMHO, get a doctor`s note, saying that you need / required to be in sunny places during the SF winter months.

This will allow you to ever negotiate remote work during the winter months or go on medical leave for the duration of the winter, negating their reason of "anyone would want it".

DO NOT go with pay reduction from your current salary, as, i imagine, you plan to work same amount of hours remotely as on site

Not sure if medical leave would be paid or not, but you mentioned that your expenses are low.

I think being presented with these choices management will agree to some sort of an arrangement, given its for medical purposes and not "just because its you".

And after working remotely for few months without productivity loss, you can start discussion of making it permanent

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