5 ms·

If you don't mind me asking, what do you do that allows you to live this kind of lifestyle? Travelling has always been a big goal for me, but making it work wit

If you don't mind me asking, what do you do that allows you to live this kind of lifestyle? Travelling has always been a big goal for me, but making it work with a stable job, and having enough disposable income to afford it is nigh on impossible.

dolmen 5y ago
In the post-COVID world many companies (at least in the tech industry) are moving to flexible office policies where full remote is possible. You don't have to be a youtuber to have that lifestyle.
- AnIdiotOnTheNet 5y ago
  Maybe not but you do still have to be in a pretty niche industry.
- mlac 5y ago
  Be careful to clear this with your company first. It can become a tax nightmare and could lead to termination if you’re working at a large organization that doesn’t have a presence where you want to work.
  - ghaff 5y ago
    Even within the US, you can't legally just have a nominal postal address somewhere and then live wherever you want. States want their money. A friend of mine was telling me their company is going to start auditing business travel records to make sure that appropriate tax filings are made. If you're not filing expense reports, will a company "know"? Possibly not. But it seems pretty precarious to expose yourself and the company at risk this way.
    - mlac 5y ago
      They will know through VPN logs - security groups look for anomalous login activity and will want to know why you’re logging in from Detroit when your work location says San Jose. It also puts your manager at risk to do it - if you tell them, then they know it’s happening and have to do something about it.
      - lizknope 5y ago
        I guess you need a VPN for your VPN
      - ghaff 5y ago
        People log in from all over the place because of business travel. I doubt that many companies are aggressively data mining where employees are located. The second point is more significant. Even with almost 100% remote work it's hard to systematically hide where you are from everyone--especially if you do any business travel or expense reimbursement or are in a materially different timezone or climate.
    - caymanjim 5y ago
      It's true that things are difficult if you don't have primary residency somewhere, but I'm unaware of any obligation to actually stay at the primary residence, so long as you're not de facto residing somewhere else and avoiding legal residency there for tax evasion purposes. Like, you can have a primary residence in NY state, and travel all year long, and so long as you're not actually spending >6 months at a specific residence in another state, and are still paying your NY and federal taxes, I don't think there's any problem. Where things get sketchy is if you're trying to claim NY is your primary residence while living in CA for 9 months of the year. I'm not a lawyer though. What I'm more familiar with is overseas residency and federal taxes. There are benefits to establishing legal residency outside the US, if you really do live and work outside the US. But then you have to be able to prove it to the IRS. If you can establish a bona fide overseas residency, you get substantial federal tax discounts (like ~$100k tax-free income), and don't have to pay state tax anywhere. But if you spend more than 33 days per year in the US, the burden of proof for establishing a bona fide foreign residency are higher[1]. Edit: update since I can't nest any more replies (to @dragonwriter) below: I sorta changed topics; my paragraph above about foreign residency is only relevant if you're earning foreign income. If you're a US citizen working for a US company, you're not getting away from taxes that way. But you can still save yourself from some personal obligation by setting up a company. [1]: https://www.irs.gov/individuals/international-taxpayers/foreign-earned-income-exclusion-bona-fide-residence-test https://www.irs.gov/individuals/international-taxpayers/fore...
      - dragonwriter 5y ago
        > you can establish a bona fide overseas residency, you get substantial federal tax discounts (like ~$100k tax-free income), and don't have to pay state tax anywhere. That’s...not true. State income tax is usually due on dollars earned in the state — it used to be usually the union of (dollars earned by residents) and (dollars earned by work in the state) but a 2015 federal court decision required it to be one or the other, and AFAIK every state with an income tax has chosen the latter over the former because, basically, resident citizens vote in the state while citizens resident in other states, the most common nonresident citizen workers, don’t. So, a bona fide overseas residence doesn't have any effect on state income tax liability.
      - 5y ago
caymanjim 5y ago
I didn't mean to imply that I've been living out of a suitcase for 30 years. I move frequently (every 1-2 years on average; longest stint in one town for the past 30 years was three years); rent furnished houses more often than not; regularly take a year or more off between jobs; travel for months at a time every few years. I don't have or want a stable job (longest job was a little over three years). I've never had a mortgage; I generally have zero debt (not even car payments); no dependents; usually no pets (I miss having pets, though). I don't own much of anything that I'm not willing to get rid of. I like the idea of having a home base and some permanent material items, but so far I don't like it as much as I like being flexible. Working in tech offers the option of remotely working from anywhere. I've worked from home (or wherever) at a number of places, going back to the early 90s. I've still spent more time in normal office jobs than remote. Now that covid has permanently altered the landscape, I expect to do it a lot more. There are unhealthy psychological aspects to all this. I avoid commitment, I feel trapped by obligations and responsibilities, I'm always thinking about what's next instead of being content with what I have. It's not for everyone.
- antisthenes 5y ago
  Wow, you're actually the real life version of George Clooney's character in "Up in the Air". I always thought it was an exaggerated portrayal, but it seems your ways are even more extreme than in the movie. Such lifestyle is so completely foreign to me, that I'm fascinated. If an alien landed on my lawn tomorrow and said "I fart gold coins", I would have an easier time believing such a thing exists than your lifestyle. How do you make friends? Can't employers sense that you're going to leave soon? Or is that specifically what they're looking for?
  - caymanjim 5y ago
    My life isn't glamorous, and much of my itinerant lifestyle has been lonely and depressing. A few times, I moved to cities where I had an established base of friends. A couple times, I managed to make new lifelong friends. Many times, I moved somewhere and never made good friends. It gets harder the older I get, but I think I'd have similar problems even if I hadn't moved as much. As I get older, the biggest challenge with friendships is that people my age have spouses and children. They've grown up and in many ways I haven't. I'm slowing down lately. I used to think I was exploring and trying new things, maybe looking for my place. Now I'm more aware of the negative aspects, like that I'm afraid of commitment, unwilling to settle, unwilling to accept that "this is the rest of my life". I'm still not ready to do that, but I no longer think that it's a universally good thing. I job-hop more than most people, but it's not completely out of the ordinary in tech work. Many people stay in one area but still change jobs every few years. People used to occasionally question some shorter (1-2 year) job stints on my resume, but I haven't been asked about it in over a decade. I don't think that particular aspect raises eyebrows anymore. There are more tech jobs than people to fill them; it's a job-searcher's market and has been for a long time.

dolmen 5y ago

In the post-COVID world many companies (at least in the tech industry) are moving to flexible office policies where full remote is possible. You don't have to be a youtuber to have that lifestyle.

AnIdiotOnTheNet 5y ago
Maybe not but you do still have to be in a pretty niche industry.
mlac 5y ago
Be careful to clear this with your company first. It can become a tax nightmare and could lead to termination if you’re working at a large organization that doesn’t have a presence where you want to work.
- ghaff 5y ago
  Even within the US, you can't legally just have a nominal postal address somewhere and then live wherever you want. States want their money. A friend of mine was telling me their company is going to start auditing business travel records to make sure that appropriate tax filings are made. If you're not filing expense reports, will a company "know"? Possibly not. But it seems pretty precarious to expose yourself and the company at risk this way.
  - mlac 5y ago
    They will know through VPN logs - security groups look for anomalous login activity and will want to know why you’re logging in from Detroit when your work location says San Jose. It also puts your manager at risk to do it - if you tell them, then they know it’s happening and have to do something about it.
    - lizknope 5y ago
      I guess you need a VPN for your VPN
    - ghaff 5y ago
      People log in from all over the place because of business travel. I doubt that many companies are aggressively data mining where employees are located. The second point is more significant. Even with almost 100% remote work it's hard to systematically hide where you are from everyone--especially if you do any business travel or expense reimbursement or are in a materially different timezone or climate.
  - caymanjim 5y ago
    It's true that things are difficult if you don't have primary residency somewhere, but I'm unaware of any obligation to actually stay at the primary residence, so long as you're not de facto residing somewhere else and avoiding legal residency there for tax evasion purposes. Like, you can have a primary residence in NY state, and travel all year long, and so long as you're not actually spending >6 months at a specific residence in another state, and are still paying your NY and federal taxes, I don't think there's any problem. Where things get sketchy is if you're trying to claim NY is your primary residence while living in CA for 9 months of the year. I'm not a lawyer though. What I'm more familiar with is overseas residency and federal taxes. There are benefits to establishing legal residency outside the US, if you really do live and work outside the US. But then you have to be able to prove it to the IRS. If you can establish a bona fide overseas residency, you get substantial federal tax discounts (like ~$100k tax-free income), and don't have to pay state tax anywhere. But if you spend more than 33 days per year in the US, the burden of proof for establishing a bona fide foreign residency are higher[1]. Edit: update since I can't nest any more replies (to @dragonwriter) below: I sorta changed topics; my paragraph above about foreign residency is only relevant if you're earning foreign income. If you're a US citizen working for a US company, you're not getting away from taxes that way. But you can still save yourself from some personal obligation by setting up a company. [1]: https://www.irs.gov/individuals/international-taxpayers/foreign-earned-income-exclusion-bona-fide-residence-test https://www.irs.gov/individuals/international-taxpayers/fore...
    - dragonwriter 5y ago
      > you can establish a bona fide overseas residency, you get substantial federal tax discounts (like ~$100k tax-free income), and don't have to pay state tax anywhere. That’s...not true. State income tax is usually due on dollars earned in the state — it used to be usually the union of (dollars earned by residents) and (dollars earned by work in the state) but a 2015 federal court decision required it to be one or the other, and AFAIK every state with an income tax has chosen the latter over the former because, basically, resident citizens vote in the state while citizens resident in other states, the most common nonresident citizen workers, don’t. So, a bona fide overseas residence doesn't have any effect on state income tax liability.
    - 5y ago

caymanjim 5y ago

I didn't mean to imply that I've been living out of a suitcase for 30 years. I move frequently (every 1-2 years on average; longest stint in one town for the past 30 years was three years); rent furnished houses more often than not; regularly take a year or more off between jobs; travel for months at a time every few years. I don't have or want a stable job (longest job was a little over three years). I've never had a mortgage; I generally have zero debt (not even car payments); no dependents; usually no pets (I miss having pets, though). I don't own much of anything that I'm not willing to get rid of. I like the idea of having a home base and some permanent material items, but so far I don't like it as much as I like being flexible. Working in tech offers the option of remotely working from anywhere. I've worked from home (or wherever) at a number of places, going back to the early 90s. I've still spent more time in normal office jobs than remote. Now that covid has permanently altered the landscape, I expect to do it a lot more. There are unhealthy psychological aspects to all this. I avoid commitment, I feel trapped by obligations and responsibilities, I'm always thinking about what's next instead of being content with what I have. It's not for everyone.

antisthenes 5y ago
Wow, you're actually the real life version of George Clooney's character in "Up in the Air". I always thought it was an exaggerated portrayal, but it seems your ways are even more extreme than in the movie. Such lifestyle is so completely foreign to me, that I'm fascinated. If an alien landed on my lawn tomorrow and said "I fart gold coins", I would have an easier time believing such a thing exists than your lifestyle. How do you make friends? Can't employers sense that you're going to leave soon? Or is that specifically what they're looking for?
- caymanjim 5y ago
  My life isn't glamorous, and much of my itinerant lifestyle has been lonely and depressing. A few times, I moved to cities where I had an established base of friends. A couple times, I managed to make new lifelong friends. Many times, I moved somewhere and never made good friends. It gets harder the older I get, but I think I'd have similar problems even if I hadn't moved as much. As I get older, the biggest challenge with friendships is that people my age have spouses and children. They've grown up and in many ways I haven't. I'm slowing down lately. I used to think I was exploring and trying new things, maybe looking for my place. Now I'm more aware of the negative aspects, like that I'm afraid of commitment, unwilling to settle, unwilling to accept that "this is the rest of my life". I'm still not ready to do that, but I no longer think that it's a universally good thing. I job-hop more than most people, but it's not completely out of the ordinary in tech work. Many people stay in one area but still change jobs every few years. People used to occasionally question some shorter (1-2 year) job stints on my resume, but I haven't been asked about it in over a decade. I don't think that particular aspect raises eyebrows anymore. There are more tech jobs than people to fill them; it's a job-searcher's market and has been for a long time.