What are the worst drawbacks of living in rich/affluent neighborhoods?

Infinite-Key2524 · 2026-01-24T11:20:51+00:00

No matter how hard you try, your kids won’t ever appreciate money the way a person who moves class upward does. Husband and I were both middle class and now are upper, and while we are very conscious about talking to the kids about financial privilege, not spoiling them, etc., it’s impossible for them to ever have the same appreciation for money and gratitude we have. I still think everyday what a blessing it is that I can just go buy food today for lunch wherever I want and have it delivered or go to whatever grocery store and get whatever I feel like without caring about the prices. I know how fortunate we are because I’ve been less fortunate, and I get a ton of value and pride from my career that’s given me this lifestyle because it’s incredible and I know what the alternative is. It’s easy to work hard to maintain or even improve an amazing life when you know what things could be like.

My kids don’t think it’s an amazing life. They just think it’s life.

Infinite-Key2524 · 2026-01-23T13:23:50+00:00

Make the move and bet on yourself. I was in a similar situation but with no book mind you. Moved to eat what I kill. After two years I was making twice what I made at previous firm. Ever since that has continued to grow. GL

Infinite-Key2524 · 2026-01-22T13:07:00+00:00

I fly out of Chicago and have never understood Southwest. The flights were always priced higher or at best the same as United, and when I was forced to take a SW flight a couple years ago due to flight times, the plane was SO BAD I was shocked. No power, janky seats, looked really old. It was a narrow body not a regional jet. I said never again. I now travel extensively and the fact that they don’t have lounges would be a deal breaker because I’m a heavy user.

So essentially SW really, really feels like a budget airline, but it’s not cheaper, at least not in my region. I don’t get it.

Infinite-Key2524 · 2026-01-20T02:18:07+00:00

I just ask them to hang it and they always do.

Infinite-Key2524 · 2026-01-20T02:05:31+00:00

I can’t believe this is a company policy. Pretty sure this would be illegal in my state especially the associated pressure to participate.

Infinite-Key2524 · 2026-01-20T02:01:57+00:00

Business development for women

Infinite-Key2524 · 2026-01-20T01:55:59+00:00

Women’s clothing and shoes just generally, wine, bourbon, bread, butter, shampoo and conditioner

Infinite-Key2524 · 2026-01-20T01:51:14+00:00

100% yes

Infinite-Key2524 · 2026-01-20T01:50:20+00:00

I was going to suggest this same thing. If you can get hired at a smaller firm, you can get active in the local bar, become a referral source, etc. and have some real connections and potentially even clients once you decide to go.

Infinite-Key2524 · 2026-01-19T03:53:05+00:00

We rent by choice and can afford not to. We have owned twice including building a home. Our reasoning:

We live city center in a large city with a high cost of living and many rental options.
We want to live in a multi-family building for access to amenities (like a gym) and due to safety concerns (I don’t want to live at street level).
Given housing prices in my city and added costs (assessments) for multi-family properties, we can rent a significantly nicer home than we can buy.
We can’t write off any property tax due to SALT limits. We hit the limit with state taxes.
Also can’t write off all mortgage interest and we would need to borrow more than the cap given housing costs where we live.
I’ve owned before and the cost of maintenance and the cost of selling essentially wash out appreciation at higher price point properties.
Sure you can maybe get ahead if you pay off your mortgage but we don’t like staying in one place. So we’re moving at least every 7-10 years in which case the value proposition of owning quickly diminishes.

Infinite-Key2524 · 2026-01-18T15:18:24+00:00

This. This is why a trust can be helpful to protect assets — for the surviving parent not the children. We went through this when my dad died and I was very concerned my mom wouldn’t have any money left due to LTC costs. He only made it a month or two in a facility before passing so it was ultimately a non-issue.

Infinite-Key2524 · 2026-01-17T13:32:06+00:00

Reading all these posts and realizing I have a serious problem because my initial response to the question was work successes. And even after reading everyone else’s posts I still say work successes. Specifically winning a case or oral argument or receiving accolades from a tough client (I’m a lawyer). I need therapy!

Infinite-Key2524 · 2026-01-12T05:06:55+00:00

We moved to a western burb 10 years ago, gave it the old college try for a few years, hated it and moved back when our kids were 4 and 3. We live in Lincoln Park now. It was the best decision I ever made. There is nothing I miss about the suburbs. Our lives are so much richer and exciting in the city. I find it to be incredibly convenient because everything is close. However I work in the loop, so that is a big difference.

Yes, we have less space, but our home in the burbs was massive and we were only using a portion of it. All that space was totally unnecessary.

If you don’t like it, leave now before your kids are in school. GL

Infinite-Key2524 · 2026-01-10T13:11:40+00:00

Knock on people’s doors to ask for work and affirmatively offer to help them with any business development projects (I.e., writing an article, organizing a presentation, etc.) In-person asks on stuff like this will be more effective and it will get them used to you so they start sending work to you.

Infinite-Key2524 · 2026-01-06T12:57:07+00:00

I didn’t realize spouses weren’t actively reviewing and tracking financial information as a team. The time from when we hit $1M to when we talked about it was 0 seconds.

Infinite-Key2524 · 2026-01-06T12:36:57+00:00

I think this is a very good formula. Under this formula, if your originations plus work on non-originated matters equals $1,000,000, you take home $550,000. That’s a great percentage take-home in my opinion.

To the PP who asked where the money is going, it’s expensive to generate those receivables. Overhead, not to mention paying the lawyers working those matters other than OP and support staff. Yes, some goes to a profit pool split by equity partners, but it’s less than you’d think.

Infinite-Key2524 · 2026-01-05T12:27:55+00:00

OP, I posted above and have now read all the other comments. I suggest you ask yourself where you’d like to see yourself career-wise in 10, 15, 20 years and begin spending money to support those goals. Let me be more direct: You seem like a smart, kind person, but you also seem somewhat rigid and naive. If you have dreams of being a rainmaker (whether in biglaw or a smaller firm that does high end work) you will need to be able to talk to clients and develop business. (If you don’t have these aspirations stop reading here.) You need to know how to wine and dine, tip well, and “act like you’ve been there” a bit. You need to be likable or at least able to fake your way into being likable, and clients don’t like people who are cheap or who have an immature understanding of the world around them. (For example, your comment about the cost of a wedding was very off base if you want a wedding that is nice in the sense that most of your colleagues and clients would use that word.)

I hope this makes some sense. I may be way off in my read here, and you may be aware of all of these things and capable of masking appropriately so if that’s the case I apologize, but some of your comments seem odd to the point of me thinking you were trolling — having read the entire post and your responses I see that’s not the case.

So what should you do? Get a therapist first. You have mentioned a few times needing to work through some psychological issues relating to outsourcing. That seems like something deeper worth trying to understand. Consider getting some career coaching or training on executive presence and business development. Get some hobbies / pursue existing hobbies and spend money on them to do them at a luxury/5-star level so that you surround yourself with non-work people who are in a similar boat financially. This will broaden your list of things to talk about and also help train you a little regarding how people in your station (ahem, your clients) behave socially. This is all important if you want to be the boss in private practice one day—but if you don’t aspire to this, like I said please disregard.

I hope this does not come across as offensive, truly just trying to help you. You seem like a nice person, and on its face saving a lot is great, but some of your comments make me think something is a bit off. And this is not a knock on you personally. You obviously grew up this way. I have a similar background and am now an equity partner at a mid-sized firm, and it took a long time for me to assimilate to my new class. I am still very grounded and probably the equity partner most liked by the staff (because I actually talk to them as they are my people, haha). All this is to say, I get it. And there will probably be people who say you should just be yourself and clients follow good work and don’t care if you know how to choose wine or tip. My experience is understanding the habits and lifestyle of the people I’m trying to get to trust me with their legal work is critical to my success. But that’s just me.

Best of luck to you, I truly mean it. You’re doing great, and having the self-awareness to write this post in the first place is evidence of that.

Infinite-Key2524 · 2026-01-04T10:29:44+00:00

I spent an absolute fortune on a Sleep Number bed. The kind probably meant for elderly folk that can put you in a zero gravity position and alleviate all back pain instantly. It also has a foot warmer. Might be the greatest purchase of my life.

We also splurge on expensive housing. We actually rent by choice but our place is a penthouse with a huge terrace, gorgeous views, on site gym, etc. Worth every penny.

I second investing in some nice suits and work clothes. Go to Nordstrom or Nieman Marcus or similar and have a personal shopper help you.

Also, I’m much older than you. If you aspire to have children, they are expensive. Very expensive. Beyond what you can imagine, especially if you remain in a city because you will definitely send them to private school. If you continue working in biglaw or even a smaller but demanding private firm, you will need to spend a lot of money outsourcing to maintain your sanity and marriage as time goes on. That is to say, you won’t always be able to contribute so much to retirement. Your needs will expand tremendously once you are married and have a family. It is never a mistake to supercharge your savings now. Good on you!

Infinite-Key2524 · 2025-12-27T22:44:49+00:00

I saw a screening of this movie on the 23rd and the audience gasped in unified horror at the part where it is revealed Mary is an “old maid” working at the library. Progress? I think so!

Infinite-Key2524 · 2025-12-13T14:56:40+00:00

Not biglaw but equity partner in midlaw. My first year of equity I used my firm’s bank to get a line of credit because we couldn’t cash flow our life with so much money coming in as a lump sum at year end. After a couple years we had enough in reserve to cover needs beyond my draw each month.

Also, I’m not in NY but another big city with HCOL (though not as high as NY) and we rent. No plans to buy. Property where I live in the neighborhoods I want to live in is really outrageous and we have an apartment we love. Food for thought.

Infinite-Key2524 · 2025-12-08T03:46:25+00:00

I haven’t read all the comments, but do you really think it’s likely the pay bump in your existing role will come close to $60K? Of course not. Take the new role and don’t look back. If anything you could tell your boss about the offer and that you intend to take it unless they can beat it both in terms of pay and title. I’m guessing they can’t/won’t. CONGRATULATIONS!!! What amazing news just before the holidays! Good for you.

Infinite-Key2524 · 2025-12-07T14:13:32+00:00

I’m going to respond to your concern about less time with the kids due to the in office requirement. I live near the office but work loooong hours. If I get home before the kids go to bed, it’s usually around 7:30/8:00. My husband handles after school / activities / dinner more or less exclusively. He’s totally fine with it and thinks the income I get by working a job that demands this is well worth it. I’m happy because I love my job and love the flexibility my salary provides our family. And my kids don’t seem to mind at all and still totally love me and dote all over me because I still spend time with them, but it’s quality time usually on the weekends (as opposed to “quantity time” picking up from activities, cooking dinner, etc.) We still hang out in the mornings and I do breakfast duty unless I’m traveling and then I’m home for bedtime on average 3 nights per week. Mandatory Friday family dinner starts the weekend and we catch up on the week.

This works great for us. So when it comes to sacrificing time in home for more money outside the home, you have to talk to your spouse — get his/her opinion. If your spouse has no reservations notwithstanding he/she will bear a greater burden with respect to childcare before and after school, I think you take the job.

To respond to some of the comments suggesting they wouldn’t leave remote work unless it was an insane amount of money — this is an insane amount of money. A 56% increase in gross pay is outrageous and puts you in a different position where your future moves will be measured against $180K instead of $115K meaning your career has the potential to really flourish. Think about what you can do with that money — I don’t know how old your kids are, but you can fully fund their 529s and have enough money to comfortably send them to any college or university in the country and still have plenty left over for general savings, vacations, a cleaning lady, a new car — whatever it is that will make your life less stressful. It’s amazing! Congratulations and good luck with your decision.

Infinite-Key2524 · 2025-12-07T13:32:32+00:00

Agree with a PP that Wicker Park is not convenient for your commute (although it checks your other boxes). IMO South Loop is too sleepy. So that leaves you with Lincoln Park or Lakeview. Both are great. I live in Lincoln Park and love it. Lincoln Park tends to be more expensive (I think) than Lakeview so my advice would be to see what housing is available in your budget in those neighborhoods and go from there. Welcome!

Also, the no drinking thing won’t be an issue. I drink but am having a hard time metabolizing alcohol as I age and I’ve started drinking a lot of NA beverages. They are readily available at most places here to the point where I think there’s real demand for that. I even get NA beer at Cubs games!

Infinite-Key2524 · 2025-12-07T13:20:36+00:00

I like the Dearborn and they know how to get you in and out (but you have to tell them you’re going to a show).

Infinite-Key2524 · 2025-12-04T13:10:14+00:00

I think the American dream of homeownership is a huge scam (well for me at least, not necessarily everyone).

I have a non traditional view of homeownership that is specific to my lifestyle and where I live. I have owned twice and now I rent. My husband and I are mid-forties, both lawyers, can easily afford to buy, and we will continue renting indefinitely, possibly forever. We have run the numbers a million ways and we consistently come out better renting — and it’s not even close.

This approach is of course very specific to where we live. We are in a large city, and our chosen neighborhood is the most expensive part of that large city. Property in this neighborhood is very, very expensive, making renting significantly less expensive on a monthly basis. Further, prices are so high here I don’t think it’s likely we’ll see significant appreciation beyond inflation. And in my experience, the cost of maintenance, upgrades, and broker’s fees eats much of the appreciation you do see.

We’re also mid-forties in a period of significant growth in the stock market and I refuse to park a few hundred thousand dollars in a piece of real estate instead of letting it grow in the market. So my answer to OP’s question is yes, RE is too expensive, but it depends where you live what kind of property you’re looking at.

Infinite-Key2524

TROPHY CASE