Working remotely + lot of vacations

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loklav
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Working remotely + lot of vacations

Post by loklav »

Hi,

I will soon start a new job that allows me to work 100% remotely. I leave in the bay area and my job is in San Diego. I just have to go there for 2 or 3 days per month. My wife works for a school district in the bay area and because of our kids, we don't want to move permanently to a new location yet. When it happens, we won't choose San Diego in all cases. I think...

So in the meantime, we were wondering how we could take advantage of this new lifestyle: I can work from anywhere and my wife has a lot of vacations. The initial idea would be for example to move to a different place during summer 2 months vacations, I will take 2 weeks PTO, the rest of the time I would work remotely, and my wife and the kids would be free to explore and visit... We are not thinking about an expensive location like Hawai, but something like Colorado or ... something in the same or very close timezone...

What do you think about this idea? How would you optimize it? Would you rent your current home? Would you rent something using Airbnb? Would you buy a second smaller house? In this last case, we could buy a place at 3 or 4 hours from where we live, rent it when we are not there... Less flexibility, but less expensive too...
Are you thinking of another way of taking advantage of this situation?

Thanks
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LadyGeek
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Re: Working remotely + lot of vacations

Post by LadyGeek »

This thread is now in the Personal Consumer Issues forum (where to live).

loklav - I also removed your duplicate post.
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dknightd
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Re: Working remotely + lot of vacations

Post by dknightd »

I would not rent out my current house. I would not buy a second house. Try it for awhile and then reconsider as needed.
If you value a bird in the hand, pay off the loan. If you are willing to risk getting two birds (or none) from the market, invest the funds. Retired 9/19. Still working on mortgage payoff.
NBKCF
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Re: Working remotely + lot of vacations

Post by NBKCF »

Does this new job give you the means to buy another house? Or are you just looking to have another property in which to work? It seems like juggling properties and organizing renting/Airbnb schedules would be cumbersome unless we are missing some relevant information.

My couple of cents, find a hobby that you can fill the time from not having to travel to the office. Even better if said hobby brings in additional income. I agree with dknightd to not make any decisions until you give it some time. You have a great opportunity (it seems) so enjoy the free time for awhile and make decisions later.
EddyB
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Re: Working remotely + lot of vacations

Post by EddyB »

I have similar circumstances. We’ve taken a few extended trips by renting a house for a month, where I work the first couple of weeks, with the rest of my family doing what they please during the workweek and me joining them in the evening and weekends, and then I take off the last couple of weeks. It’s a good way to see places that merit more than a couple of weeks.
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Watty
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Re: Working remotely + lot of vacations

Post by Watty »

loklav wrote: Sun Feb 17, 2019 12:33 pm I will soon start a new job that allows me to work 100% remotely.
It might be good to work in the new job for a while to get settled in there before figuring out what what to do.

You did not say the ages of your kids but at some point being away from home from long periods of time may not work well since they would be away from their friends, activities, and sports.
Topic Author
loklav
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Re: Working remotely + lot of vacations

Post by loklav »

EddyB wrote: Sun Feb 17, 2019 9:52 pm I have similar circumstances. We’ve taken a few extended trips by renting a house for a month, where I work the first couple of weeks, with the rest of my family doing what they please during the workweek and me joining them in the evening and weekends, and then I take off the last couple of weeks. It’s a good way to see places that merit more than a couple of weeks.
yes at the minimum this is what we want to do. I was trying to figure out a less expensive way than paying for 2 houses at the same time... But in the beginning, this is definitely a good approach. That could also help us to identify a place where we would like to move later...
Since you have been doing it several times, do you have any recommendations? Anything to pay attention to? What did not work out?

thx
EddyB
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Re: Working remotely + lot of vacations

Post by EddyB »

loklav wrote: Mon Feb 18, 2019 12:21 am
EddyB wrote: Sun Feb 17, 2019 9:52 pm I have similar circumstances. We’ve taken a few extended trips by renting a house for a month, where I work the first couple of weeks, with the rest of my family doing what they please during the workweek and me joining them in the evening and weekends, and then I take off the last couple of weeks. It’s a good way to see places that merit more than a couple of weeks.
yes at the minimum this is what we want to do. I was trying to figure out a less expensive way than paying for 2 houses at the same time... But in the beginning, this is definitely a good approach. That could also help us to identify a place where we would like to move later...
Since you have been doing it several times, do you have any recommendations? Anything to pay attention to? What did not work out?

thx
If you’re open to doing home exchanges, that’s something to consider (e.g., homeexchange.com).

Once you have your own home-office setup worked out, you’ll know what you need to have in the vacation spot.
A lot depends on your spouse and kids’ interest and enjoyment in living “regular” life someplace else for a couple of weeks, rather than being in “pure” vacation mode.
Last edited by EddyB on Mon Feb 18, 2019 12:29 am, edited 1 time in total.
Topic Author
loklav
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Re: Working remotely + lot of vacations

Post by loklav »

Watty wrote: Sun Feb 17, 2019 10:34 pm
loklav wrote: Sun Feb 17, 2019 12:33 pm I will soon start a new job that allows me to work 100% remotely.
It might be good to work in the new job for a while to get settled in there before figuring out what what to do.

You did not say the ages of your kids but at some point being away from home from long periods of time may not work well since they would be away from their friends, activities, and sports.
yes, first my wife proposed to come with me for a week at San Diego since at the beginning it will help me to meet the teams.
My kids are 16-13-9-9 years old. We always wanted to build a life outside of the bay area. And when the eldest will go to college we will certainly move to somewhere else... So this is why I'm really excited to be able to work remotely now.
Thecallofduty
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Re: Working remotely + lot of vacations

Post by Thecallofduty »

I would just plan ahead and rent a house you both like or want to try out during the summer vacation or other times you want to leave the bay area. Im sure there is good deals for
Monthly rentals.
Sounds like you have a good gig and lots of potential to have new experiences with the family. Renting places will keep lots of flexibility.
-thecallofduty
Starfish
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Re: Working remotely + lot of vacations

Post by Starfish »

Don't kinds ave plans for vacation, summer classes to take, friends to be with etc?
For me I would find it hard to focus in an exciting new place while working from home. If you can do it, it sounds great.
TravelGeek
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Re: Working remotely + lot of vacations

Post by TravelGeek »

A couple of comments:

- since this is a new job for you, make sure you develop sufficient trust with your manager and team that you can and will work effectively while being away from your regular workplace (home base).

- if you work from another state, consider the potential need to file a state income return in that state. Your payroll department may even need to be aware of your changed work location.
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Watty
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Re: Working remotely + lot of vacations

Post by Watty »

One more thing to consider. To work remotely you will almost certainly need high quality internet and cell phone connections. These will be hit or miss in a rental and even if you buy property somewhere you may find that the options in a rural area are a lot lower quality than you are used to. Power outages may be more common too and last longer than you are used to.

Especially as a new employee it might not go over very well to be trying to work in a location where you are having technical issues.
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lthenderson
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Re: Working remotely + lot of vacations

Post by lthenderson »

loklav wrote: Sun Feb 17, 2019 12:33 pm I will soon start a new job that allows me to work 100% remotely. I just have to go there for 2 or 3 days per month.
Technically you have a job that allows you to work 86% of the time remotely. (I'm assuming around 22 working days a month on average.) :sharebeer
Colorado13
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Re: Working remotely + lot of vacations

Post by Colorado13 »

loklav wrote: Sun Feb 17, 2019 12:33 pm Snip... We are not thinking about an expensive location like Hawai, but something like Colorado or ... something in the same or very close timezone...

Thanks
What is your budget? Depending on your intended location and need for high speed internet (I'm guessing), CO may not be as affordable as you might be hoping. If you have some locations in mind, send the list our way and we can provide feedback about potential cost, entertainment options for the kids, etc.

Also, if you are planning this change of location for this summer, you probably need to act really quickly. There may be slim pickings for VRBOs in some locations. Often for CO trips, we secure our rentals 6-10 months in advance. We certainly welcome visitors/tourists. :happy
Topic Author
loklav
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Re: Working remotely + lot of vacations

Post by loklav »

EddyB wrote: Mon Feb 18, 2019 12:25 am
loklav wrote: Mon Feb 18, 2019 12:21 am
EddyB wrote: Sun Feb 17, 2019 9:52 pm I have similar circumstances. We’ve taken a few extended trips by renting a house for a month, where I work the first couple of weeks, with the rest of my family doing what they please during the workweek and me joining them in the evening and weekends, and then I take off the last couple of weeks. It’s a good way to see places that merit more than a couple of weeks.
yes at the minimum this is what we want to do. I was trying to figure out a less expensive way than paying for 2 houses at the same time... But in the beginning, this is definitely a good approach. That could also help us to identify a place where we would like to move later...
Since you have been doing it several times, do you have any recommendations? Anything to pay attention to? What did not work out?

thx
If you’re open to doing home exchanges, that’s something to consider (e.g., homeexchange.com).

Once you have your own home-office setup worked out, you’ll know what you need to have in the vacation spot.
A lot depends on your spouse and kids’ interest and enjoyment in living “regular” life someplace else for a couple of weeks, rather than being in “pure” vacation mode.
I like this idea of doing home exchanges...
I'm already used to work remotely a few days a week, I didn't really need a specific setup until now, just my laptop and a WIFI connection. Sometimes I was working from home and some other times from the library. But I didn't have any kids around ;)
So I guess an important part for me would be able to find a place where I can be isolated for a few hours a day...

When we go on vacations, we usually use VRBO/Airbnb to rent a place for a few days, no more than a week. When you want to rent for at least 2 weeks, do you use something different?
michaeljc70
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Re: Working remotely + lot of vacations

Post by michaeljc70 »

I have a friend that has quite a bit of flexibility where he works. He works in Chicago and has a 2nd home in Michigan. Most weekends he works Friday and Monday in Michigan and spends a 4 day weekend there.

You mentioned doing this in the summer. That will probably be the most expensive time to rent a place (though it depends where you go). You are competing with families on summer vacation.
THY4373
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Re: Working remotely + lot of vacations

Post by THY4373 »

A couple of thoughts from somebody else who works remotely and I am repeating some of what has already been said.

One, I would get into your job and build some trust before doing this.
Two, I would do this with full transparency of my boss and folks who report to me.
Three, There are potential tax implications here and you HR folks might have some say in this as I know there can be legal issues. My employer used to be anywhere in the 50-states but has since narrowed down the number of states considerably (folks already elsewhere were grandfathered). I believe for example NY state is either 20-30 days in state (not necessarily continuous time) in a year before you have to file taxes there.
Four, not that you are suggesting this but international locations would really complicate point three above.
flyingaway
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Re: Working remotely + lot of vacations

Post by flyingaway »

Have you heard of people who call themselves digital nomads?
They are the ones who work online (or not need to go to a fixed office) and travel around the world. Most of them have no spouse, no kids, and no mortgage.
btenny
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Re: Working remotely + lot of vacations

Post by btenny »

I second those who suggest you focus on getting into the "grove" and setting up your home office with the new job. Do you have a special room for your laptop and printer and a good chair and desk? Is the Wifi adequate for your work? Can the room be closed off so it is quiet and away from your kids? How will you take breaks? Lunch? How often do you need to talk to your team and meet with them? Weekly? Bi weekly? Monthly? When you get all this settled you can focus on working remotely at second locations.

My son works from home and has for years. He has a dedicated office bedroom where he closes the door and works. He has dedicated high speed wired internet and printers and two screens. He has a special dedicated office laptop computer. His company pays for an IP guy to set up and fix this stuff as needed and pays for his special high speed internet. No one else uses that room. He takes breaks about once an hour and goes for 5 minute bike rides. His hours are built around his boys and school and his sports teams. He coaches and runs kids winter and summer sports teams in his extra time. He also goes to his lake house and my lake house for weeks during summer. He usually works from a quiet room for part of those weeks. He does the same for winter vacations to Florida. He says he gets by in those weeks with his laptop but it is not as good as his office.

Good Luck.
mlipps
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Re: Working remotely + lot of vacations

Post by mlipps »

If my parents had tried to drag me off to a cabin with them for 2 months at 16 years old, away from my friends, my summer job, and my school activities, I would have rioted in the streets. I think you're insane to do that to your kids past the age of 10 or so. A couple weeks, fine. An entire summer? Absolutely not.
HornedToad
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Re: Working remotely + lot of vacations

Post by HornedToad »

I would be careful doing this and definitely talk to your manager. As a remote worker, you presumably have very good internet at your house, a good working room that's quiet with good phone/headset/etc and you are working PST hours.

If you go remote in a "vacation" location and your internet changes, your call quality drops for teleconferences or you aren't working the same hours then those are very noticeable. If it was a 1 week vacation then that's fine, but going for months then I would just be careful.
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loklav
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Re: Working remotely + lot of vacations

Post by loklav »

Thank you all for all this information.

I want to emphasize that I'm already a remote worker and that my new employer hired me as a remote worker.
So I know what it means to work remotely. Of course, I'm far from being the exception in this company.

My laptop and a wifi connection are all I need to work remotely. As I said previously, I currently work remotely sometimes from the library or Starbucks or ... and this is good enough.

I don't plan to go to a different country for 2 months in the beginning. More 2 weeks, 1 week work/1 week vacation.
Very interesting the comments about the tax implications... I will talk about it with the HR people.

Probably spring break will be our first test!

Thanks for your help.
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loklav
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Re: Working remotely + lot of vacations

Post by loklav »

mlipps wrote: Wed Feb 20, 2019 2:18 pm If my parents had tried to drag me off to a cabin with them for 2 months at 16 years old, away from my friends, my summer job, and my school activities, I would have rioted in the streets. I think you're insane to do that to your kids past the age of 10 or so. A couple weeks, fine. An entire summer? Absolutely not.
:) yeah teenagers are difficult sometimes... but we are from europe, where we had a lot more vacations than here in the US. So kids are kind of used to spend a lot of time with us during the vacations, make new friends, see different things and reconnect again with their friends when the school starts again...
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loklav
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Re: Working remotely + lot of vacations

Post by loklav »

michaeljc70 wrote: Wed Feb 20, 2019 11:57 am I have a friend that has quite a bit of flexibility where he works. He works in Chicago and has a 2nd home in Michigan. Most weekends he works Friday and Monday in Michigan and spends a 4 day weekend there.

You mentioned doing this in the summer. That will probably be the most expensive time to rent a place (though it depends where you go). You are competing with families on summer vacation.
Yes, I cannot do exactly this thing. My wife works and my kids have school. So this is why I was more thinking about going to a different place during the vacations.
Buying a second house would be an option, but after sometimes everybody would kind of be bored...

Renting gives more flexibility but is more expensive. Home exchange is interesting but do we really have time to spend to make our house "guest ready"...
We will certainly try something simple, once everything is in place.
This is not something that we will do systematically but once or twice a year, why not? Xmas or 3 weeks during summer (2 weeks vacation/1 week work) somewhere else...
michaeljc70
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Re: Working remotely + lot of vacations

Post by michaeljc70 »

loklav wrote: Fri Feb 22, 2019 5:40 pm
michaeljc70 wrote: Wed Feb 20, 2019 11:57 am I have a friend that has quite a bit of flexibility where he works. He works in Chicago and has a 2nd home in Michigan. Most weekends he works Friday and Monday in Michigan and spends a 4 day weekend there.

You mentioned doing this in the summer. That will probably be the most expensive time to rent a place (though it depends where you go). You are competing with families on summer vacation.
Yes, I cannot do exactly this thing. My wife works and my kids have school. So this is why I was more thinking about going to a different place during the vacations.
Buying a second house would be an option, but after sometimes everybody would kind of be bored...

Renting gives more flexibility but is more expensive. Home exchange is interesting but do we really have time to spend to make our house "guest ready"...
We will certainly try something simple, once everything is in place.
This is not something that we will do systematically but once or twice a year, why not? Xmas or 3 weeks during summer (2 weeks vacation/1 week work) somewhere else...
Renting gives you the ability to try a lot of different places. I had originally planned on buying a winter/retirement place in Florida, but am now leaning toward rentals due to the flexibility with location and timing.
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