Real Life Admin

So, I have moved to Singapore and been enjoying it for almost a year now. However still trying to hustle to the next level (ding!).

Missed out on a level up leading a boats division, but have been asked if I would be interested in leading a land logistics division. Only wrinkle, it would require another international move with the family… this time to Chicago! Which I hear is lovely and sunny…. Or not quite.

I have no idea about living in the states as an expat (originally Australian)…. So what better place to come on the internet than my favourite gaming friends and ask them for advice!

Thoughts? What should I know about moving there other than avoid the guns? Is it a nice place yo raise primary school kids? How would you set yourself up?

Thanks in advance!


I am a country boy at heart and don’t particularly like any big cities. I live about an hour north of Chicago. Opinions certainly may vary but if your work is in the city proper there are many train lines if you’d rather live outside the city and commute.

As for the city itself, it used to get a very bad rap due to the (primarily) gang violence on the south side. Or Al Capone if you’re 100 years old. The crime has begun to creep into the nicer areas of the city but it is still sound advice to stay out of the south side.

I used to go to law school downtown and was there every day but I haven’t been back to the city but once in the last 5 years.

Be sure to enjoy the food, though; there is plenty and much of it is fantastic.


My brother lives in Hinsdale, which is a suburb of Chicago to the West of downtown. He has been there 25 years now and loves it, even passed up a promotion that would have required moving to Seattle, just to stay in Chicago.

I think you have a lot of very nice suburbs with good schools that are a short commute by train into the city for work.

Does your family like the idea of possibly living in the US for a while?


Best friend lives in Chicago and has for about ten years and loves it. Active arts scene, amazing restaurants, and lots of interesting things to go out and do. I’ve visited several times over the years and liked it, but there is serious crime in some areas, and you’ll want to do some online research about the schools for sure. Seriously–there can be huge differences in quality of schools in a US city.

I am not much anymore for big cities, so I would never live there, but if someone forced me to, I wouldn’t feel like it was a terrible thing.

The one thing I will note is that it is very expensive. Chicago is one of the most expensive places to live in the US (and possibly the world?) so be sure that you understand the cost of living there as opposed to where you are now and what kind of salary it would require for you to live there with a family. The suburbs are an easier lift financially, but even they are pretty high, especially given the escalating cost of housing in this country right now.

You may be able to get better results to these and other questions by asking on reddit. I’m sure they have a Chicago sub and people there are usually very helpful.


Well if he is in Singapore now, he is in a more expensive place to live than Chicago. Singapore’s cost of living is around the same as where I live in NYC.

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Did not know that! Wow.

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Oh Yeah, Singapore is insane as an expat.

$40k/year per kid for school
$7k/month rent for a 1400 sqft four bedroom apartment 45mins commute.

Thanks for the info team :). I have thrown my hat in the ring… maybe I will end up watching a Bulls game…

Got an email as I do every so often from the website with a kind of digest and saw this post. Been wondering how you all were getting along, amazing that this forum is still going!

I lived in Chicago for over a decade. I did not hate it and in fact was somewhat sad to leave, but I am in no hurry to go back. The weather is terrible. Hot and very humid in the summers, extremely cold (and very windy [yes, I know, but that’s actually not why it’s called the Windy City]) in the winters, with lots of snow. The suburbs are fairly characterless bedroom-and-stripmall communities that often don’t even have sidewalks. That’s America. It is one of the very few (like…two) cities in the US with a pretty robust public transit system, although it is way behind New York in that regard. Traffic is very bad, and I can only imagine it’s gotten worse in the years since I left. It was when I lived there surprisingly cheap for a place of its size. There are some interesting things there that you won’t find too many other places, like the swordplay guild long-time readers may recall I belonged to.

What I’m really interested in is what kind of job has you running logistics all over the world!


Thanks for the info all!

So…. Looks like we are going to head across by the end of the year.

It’s logistics for a global mining company - trucks / rail / containers / some shipping.

Received the offer, looks good - now to start to understand what a 401k is as well as these strange health and retirement benefits.

And tax - I worked it out to be around 32% for Illinois - am I close?

Sounds about right. You will possibly want to engage the services of an accountant.

As for the 401k that’s the entry ticket to the casino that we replaced pensions with and as for navigating the American healthcare system…good luck.


I will be very interested to follow along the adventures of your family here in the US. Please update us regularly once you arrive.


The individualism/personal responsibility ideology, combined with the corruption which has led to lax antitrust enforcement, tends to mean that there are massive power imbalances between most people and the providers of their services and goods. Consequently, you end up agreeing to a lot of legal verbiage which A) you sometimes don’t even know you did, as when opening a box is considered consent to the EULA inside the box, B) is not interpreted by the legal system to mean what the words mean in other contexts, as when I discovered that the insurance which paid 100% of all reasonable and customary charges for a dental procedure defined “reasonable and customary” well below what they actually charged at the dental facility operated by the same organization which provided the insurance, and C) costs too much in both money and time to fight in court even if you could win. So expect to get legally robbed a few times, and accept that this is just the cost of “freedom”—you’re better off accepting it ahead of time than believing the bullshit that you should have read the terms more carefully or filed form 278-C-2 six years ago or whatever, and then feeling bad about yourself.

Generally, don’t buy extended warranties and don’t answer phone calls from numbers you don’t recognize. Don’t talk to the police more than necessary. Typically, trust individuals and volunteers; for all the systemic crap, most people are great. But we’ve seen a surge in violently inflexible ideologies of late, so avoid challenging those who advertise a political view.

Chicago’s not ideally situated for the most dramatic natural beauty, but it’s an airline hub, so if you’re at all into wilderness, you could get direct flights to lots of places with national parks. Our national park system has some pretty accessible, spectacular stuff, and some deliriously wild and remote stuff, as well.



I am currently watching a 30mins video on the healthcare systems and benefits for my company.

I am a mix of amazed and horrified. Some cool stuff in here but the complexity is insane.

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Oh my gosh, I now know what you mean and why Wallstreetbets makes sense.

For the the price of freedom, each individual can do whatever they want - 100% personal accountability.

That’s…. Bizzare!


But… I mean… I’m a nice guy!

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I guess from my perspective, at least you are not NYPD, our local street gang.

They mean well but have poor leadership and direction.

I will just speak from my own perspective and carefully, because you and I are not going to agree on this, but I, as a white middle class looking guy, have never had an interaction with the NYPD where I thought anything other than “what assholes.” I cannot imagine what it must be like to deal with them without the white male privilege that I have.


If you ever stopped me on the road, I’d pull out my iPhone and start playing Ascension with you…


Uh… Best. Day. Ever!

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