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Early Retirement (2006)

philip.greenspun.com

271–280 of 308 posts

Re: Early Retirement (2006)

#271

Earlier quoted context omitted.

This person seems to have extreme, simplistic views that they hold as the truth. Non-profit organizations exist to provide their staff with great jobs" ? He honestly believes that? How many has he worked with? I've worked with non-profits my whole life, and some are flawed, but many do tremendously valuable work. No to the beach ? Depends on your preferences. To the author: Taking personal, anecdotal experiences and…

If you read more of Philip Greenspun's writings it's apparent that he likes to inject a bit of satire into them. Both self-deprecating and deprecating others. I figure that he hit it on the nose with that bit.

He's punching down, and is toxic in general. I forgot about it until I clicked the link (or maybe didn't notice it the first time I read it)

Re: Early Retirement (2006)

#272
post #70

Earlier quoted context omitted.

I read some interesting advice somewhere that said: "Sit still until you're compelled to move." I think the idea is that a lot of our wants / desires are urges that come and go, but our dreams and needs are deeper than that and we have to let those urges pass before we can find out what our true desires are.

I've tried that. Things that compel me to move: Food, water, bathroom, pain. Perhaps I lack dreams.

I think they’d say, “Keep sitting”

Re: Early Retirement (2006)

#273

Earlier quoted context omitted.

Any growth in the "government's portion" is yours until you sell. Also, if you sell after retirement the tax rate is going to be low if you don't have much non-investment income.

I agree it's yours until you sell. We are just debating semantics (does retiring with $14M mean retiring with $14M you can spend, or $14M minus taxes that you can spend). Also, Capital gains is treated differently than ordinary income. Your income tax bracket is irrelevant in determining your capital gains rate (at least for now).

https://www.nerdwallet.com/article/taxes/capital-gains-tax-r...

Income tax bracket doesn't directly correspond with capital gains brackets, but total income affects the capital gains tax rate.

Re: Early Retirement (2006)

#274
post #85

Why isn't healthcare insurance more like car insurance? Almost everyone can afford to pay car insurance and are not worried about going broke and filing for bankruptcy if they have an accident or get a speeding ticket. A friend got covid, almost died and then got a large five figure medical bill. They had insurance via the employer, but the hospital ER/ICU they were transported to was out of network. How is a very si…

Car insurance has capped payouts, and any policy which is considered by the insurer to be too much of a risk would be denied.

Unlike a car, health costs are both unbound, and good health has infinite utility (you'd always be willing to pay as much as you can for good health,) and unlike car ownership, is also a basic human right.

Re: Early Retirement (2006)

#275

A tangent comment, but his website is such a fun throwback. I remember finding the Philip and Alex's Guide to Web Publishing ( https://philip.greenspun.com/panda/ ) when it was first put up. What an amazing eye opener for me at the time to what the internet would/could be. Plus I loved his napkin-style diagrams and interspersed photos.

Every now and then I come across a link to one of his webpages. I'm glad he's kept them up for so long.

Re: Early Retirement (2006)

#276

Earlier quoted context omitted.

Just an FYI that if you avoid permanent US residency via green card or US citizenship you can potentially take advantage of a step-up of the cost basis of ALL your taxable assets when you move back to Canada, thus erasing any tax on the capital gains -- both short and long term. (In Canada, there is no distinction of short or long term gains). Assuming that you have little-to-no Canadian assets now, dispose of everyt…

If you’re Canadian, can’t you work on a TN visa? Thought this was renewable multiple times and had no credit for immigration…

(This post is not legal advice, consult an immigration lawyer, etc.)

Yes and no. TN is technically only for specific professions drafted in like the 80s or something. It's incredibly stupid. For example, many Canadians use "Computer Systems Analyst" for their TN which explicitly forbids programming, as a programmer is not considered a professional job in the eyes of NAFTA. It's bananas. If you don't have a decent secondary education with a recognized degree, you're likely out of luck.

And while yes, you can effectively ride TN status forever, it has a lot of downsides. For one, it's not portable, so you have to restart the process if you switch employers. In theory you can't even seek employment while on a TN. Two, the customs agent letting you into the US can decide at their leisure whether or not you qualify. It's rare but I know of a few instances of people getting rejected for no real reason. If they think you are abusing it, they will reject you, etc. If you lose your job for whatever reason, you have to leave ASAP. There is not much peace-of-mind with TN status.

Compare to an H-1B, which confers a ton of benefits, like a straightforward path to a green card (also possible with a TN but a lot of lawyers are less comfortable), easy to switch employers, your employer must pay for everything, if you're fired your employer has to pay for your travel, there is a lengthy grace period where you can be unemployed to either find work or wrap up your affairs, you can stay in the country while waiting for approval, etc. It's a million times better than TN.

Attorneys probably also dislike TN status because they really are not necessary. The applicant, not the company, must pay the application fee. In theory you don't need lawyers at all, but it is pretty useful for them to prepare the documents and cover letter for you. Get your ducks in a row, etc.

Most Canadians I meet in the US who are on TN status or H-1B visas are, at least initially, on the path to a green card. Most half-decent employers who are willing to sponsor want to put you on that path anyways, since it ensures your position is not going to evaporate because you were denied at the border or something. Most people on non-immigrant or immigrant-status visas want a green card anyways, so it is sort of the default path.

Lastly, most folks do not know about the downsides of a green card, such as the frustratingly complex tax burden if you are abroad, that it expires if you leave for ~5 years, etc.

Re: Early Retirement (2006)

#277
post #90

Earlier quoted context omitted.

You can read all the philosophy in the world. It doesn't automatically turn into actionable realities. Also, any philosophy is subjective, you are a human, you said something, I am a human, I beg to differ and so on and on....

Absolutely you can read it to death and still glean nothing from it. I don't know how many times I've had to reread, and I usually continue to do so. And to that end it takes more than just reading it, but if one wants to ask some profound questions about the world around oneself now that one doesn't have someone breathing down one's neck then one should probably start where others left off. It'll save a little time.…

I think we are talking about two different things. If you are talking about logic, formalism and objectively verifiable things, sure, I totally agree with you. But I am talking about principles that should govern life. Unless you pivot to a Higher moral Authority, I am just taking things to their logical end and saying morality is arbitrary and no amount of philosophy will change that.

Re: Early Retirement (2006)

#278

Earlier quoted context omitted.

If you’re Canadian, can’t you work on a TN visa? Thought this was renewable multiple times and had no credit for immigration…

(This post is not legal advice, consult an immigration lawyer, etc.) Yes and no. TN is technically only for specific professions drafted in like the 80s or something. It's incredibly stupid. For example, many Canadians use "Computer Systems Analyst" for their TN which explicitly forbids programming , as a programmer is not considered a professional job in the eyes of NAFTA. It's bananas. If you don't have a decent se…

Or you can do what I'm doing and make the big bucks working remotely out of a small town in Ontario for a SV company ;)

Once you get to staff+ you effectively remove any real pay difference based on your locality.

Re: Early Retirement (2006)

#279
post #15

Earlier quoted context omitted.

I think easing out of work is important. My dad 'retired' at 67 and instantly got hired back as a consultant on an hourly basis. He then spent the next 3 or so years slowly cutting down his hours until he was only working ~20-30% at which point he felt ready quit.

Similar. My old man went back to his old job as a consultant. It was supposed to be 20 hours a week and quickly turned into 40. Then he gradually reduced over time.

Probably my ideal thing would be some project-based (non-dev) consulting that wasn't too many hours and that let me disappear for a month here and there. I'm not sure I could really count on that though--especially without a lot of beating of bushes--which leads me to put in a bit more time while I easily can.

Re: Early Retirement (2006)

#280
post #65

Earlier quoted context omitted.

My plan is: - Move to America, become rich - Move back to Canada, retire - Win :P

Just an FYI that if you avoid permanent US residency via green card or US citizenship you can potentially take advantage of a step-up of the cost basis of ALL your taxable assets when you move back to Canada, thus erasing any tax on the capital gains -- both short and long term. (In Canada, there is no distinction of short or long term gains). Assuming that you have little-to-no Canadian assets now, dispose of everyt…

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