Ask HN: How would I go about negotiating an extended working vacation? | Hacker News Reader

Ask HN: How would I go about negotiating an extended working vacation?

4 pointsjtreminio6 comments

I'm the sole developer at a small, profitable eCommerce company.

I have my own office, but I don't need it - I am easily able to do everything remotely.

So, I want to take 2 months next year to work remotely... as in, way remotely. I'm in Dallas, I want to work from Central America for 2 months.

I'm a big boy, and I am not afraid to sit down with the boss and list this out as a demand - but I want to go about it in a tactful way that does not make him feel like I am taking advantage of the company.

I've brought working remotely up before, and his reasoning for not allowing me so far has been that he's had bad experiences with previous developers (no longer there) that were able to work remotely. I know that by the time June rolls around there'll be no question about my commitment to the company and the benefits I bring to having me around, so I do not believe this will be a valid excuse at all.

All I can think of is working from El Salvador in a hammock! Please give me some advice that I can use to my advantage.

Ask him. If he says 'no' then give him 2 weeks notice and start looking for a boss that's cool with that. (That's how you negotiate. If are not ready or willing to leave the job, then you are merely arguing with him.)

This may be the path I end up taking... "I will be taking 2 months to go out of the country. I'd like to be able to work remotely during that time, or we can start making arrangements for someone to take over my responsibilities"?

I'd be precise about the plans - "May and June 2012" and so on.

Actually, many people quit jobs just so that they can take an extended vacation.

A guy I work with did something similar to spend a year hiking South America with his wife. He gave plenty of lead time, and was able to negotiate an unpaid leave of absence deal where he wasn't working, but the company paid his health benefits and ensured he had work to do when he got back.

I believe he's on some sort of contract to stay here for the next year or so because of the deal, but I haven't pried. This is a large government contractor, so if they are able to work something like that out I'm sure you'll be able to find something that works for you.

Write down your needs, and have an honest conversation with your boss. Never know unless you ask.

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