Smashter's Great Adventure

Where are you and where are you going?
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Smashter's Great Adventure to Chicago

Post by Smashter » Thu Jul 26, 2018 8:34 am

The startup I was working at decided that continuing operations in New York was no longer sustainable, and I was let go. I got a 2.5-month severance, lump sum, which I am thrilled with. I was sick of the job anyway but I had the golden handcuffs on so tight I was losing circulation. I probably started and then deleted 5 posts along the lines of this one, asking if it would be worth it to leave a high paying job for something lower paying but more sustainable.

Now, I feel free and like I can finally try new things. DW and I took the job loss as a chance to reassess our situation. We decided to move to Chicago to be closer to family and to reduce our cost of living.

So, within the next month, I will be joining the long list of ERE’ers who live or have lived in Chicago. I’m excited!

Any suggestions on where to live? We’d like to pay $1400 / month max. We are currently paying $2100 for a Brooklyn studio, so pretty much anything will be an improvement over that.

My wife will be working in the Loop, and I am still job hunting but will probably end up in an office near hers. We are trying to find a place within a 3-mile radius of work so that we can see what city life is like with an ultra-short commute.

I could walk/bike anything under 4 miles (I’ve done further in NYC), so even with high rent my housing score could still be a respectable 14.

Mister Imperceptible
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Re: Smashter's Great Adventure

Post by Mister Imperceptible » Thu Jul 26, 2018 10:51 am

Congrats on being liberated from the golden handcuffs. A old colleague told me being laid off is one of the most freeing things because it eliminates the choice of being able to stay.

Could you talk your wife into living in an RV? Or do Division I basketball players not fit in RVs? :P

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Re: Smashter's Great Adventure

Post by suomalainen » Thu Jul 26, 2018 10:57 am

I'm irrationally envious.

-Golden handcuffs guy

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Re: Smashter's Great Adventure

Post by RFS » Thu Jul 26, 2018 1:53 pm

Good luck with your move! I hope it's a refreshing and invigorating change.

You should check out the Pilsen neighborhood in Chicago. It's a Mexican neighborhood that has changed/gentrified a lot in the past 10 years. 2.9 miles from the city center on Google Maps.

The Northeastern part is the nicest, and it gets crappier as you go southwest. I heard to avoid west of South Racine, but that was about 4 years ago.

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Re: Smashter's Great Adventure

Post by Smashter » Fri Jul 27, 2018 9:33 am

Thanks guys.

@RFS Pilsen is interesting to me but I think it's a bit grittier than DW is wants. We've been zeroing in on Wicker Park, Ukranian Village, and Lincoln Park.

@MI lol, DW is so easy going and resilient and down with so many ERE things, but living in an RV would be a bridge too far : )And also, I am one of the lucky few who played bball at an elite level but is still small enough to comfortably fit in a coach seat on a plane. My brother is 6'4. Oh, cruel genetics!

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Re: Smashter's Great Adventure

Post by Smashter » Thu Nov 08, 2018 9:49 pm

I totally underestimated how mentally challenging it would be to move to a new city and find a new job. My transition was so supremely awful that I hope it can stand as a lesson for someone else in what not to do. Here’s what happened:

While searching for jobs before my move to Chicago, I narrow it down to two choices. One of them is a tiny startup that seemed really excited to potentially have someone with my experience. I get excited about it too, totally get the CEO’s hopes up and imply I will join the team, and then change my mind at the last second to take the higher paying job at a more established company.

I start learning more about the field I am going to to be in and something isn’t sitting right with me. The company sells third party data (gleaned from god knows where) in order to power more effective online ads. My job (sales) would be to hunt people down and be like “yo, I know you are already buying data from 9 other sources, but you should use our source too. Also we have a way of tracking people without using cookies, which is totally legit and not creepy.”

Coming out of a sales job that already made me feel kind of sleazy, I start having second thoughts. I figure that because I already paid off my student loans and my wife and I had built up a 200k surplus, I was stable enough to stop doing dumb sales stuff if I wanted

I back out of my offer three days before I am supposed to go back to NYC to start training. I refund them for my plane ticket. They are not happy. The recruiter who found me the job is especially salty, having now lost out on her commission.

I feel bad, but motivated. I am going to do work I like and am at least somewhat proud of!

I go to the ERE meetup at Jacob’s house. It’s great. Awesome dog, awesome garden, tons of inspiring people to learn from.

I spend about two weeks searching for jobs in the field I like and have some experience in, get anxious and scared, give up.

I go back to the original startup that I bailed on and say “now I want to join you!” The CEO is thrilled, brings me on board right away. 2 weeks into the job I realize I am in way over my head. It was a strange feeling. Before I started, I really thought I’d have the motivation to do what the job required, but I totally did not. Not even close. I’m panicking. I hate the work and feel so bad for joining the company. My mental state deteriorates.

I start to have a lot of trouble sleeping. I wake up between 2-4 AM and have racing thoughts about how I should have just stayed with that first damn job. It was so much money! I could have just toughed it out for a few years and been FI. Now my savings is stagnating! I cannot stop ruminating about how I shouldn’t have bailed on the first job. Negative thoughts loop in my mind.

My amazingly patient and loving wife spends like 700 hours reassuring me that she doesn’t think the first job would have been a good fit and she is proud of me for leaving and this is all a phase that will pass and money isn’t everything and she loves me very much. I nod like I am absorbing what she is saying but after each talk instantly start feeling overwhelmed with regret once again.

On top of the job stuff, I start to miss Brooklyn. I decide that I had it perfect there, I never should have left, and that I am an immature loser who is never satisfied and always thinks the grass is greener. I am not sure what to do with this information except sulk.

I start to feel depressed in a way that I haven’t felt in 6 years. It’s bad. My wife talks to me and I am awful and then she cries and tries to get me to see a therapist. I don’t. I don’t even want to read the forums anymore, something I love, because every positive journal report about people making great money and reducing their SWRs makes me feel more awful. I don't want to seek career advice on the forums because I feel dumb and embarrassed.

Now I have a job that sucks and barely pays anything. At least before I was getting big bucks to do my not very interesting job. I decide to quit. My boss is surprised and disappointed but very supportive and kind overall.

I feel terrible about everything. I consider going back to sales just for money, but can't, having now told two separate jobs that I am leaving because I no longer want to do sales. I think a third time would qualify me as a sociopath. I have a modicum of honor.

I lash out my brother over text message and start a massive fight. We both say very mean things to each other. It’s very upsetting.

Things get a little better as I slowly pick up freelance work in the area I like. It gets to the point where I am decently busy and making some good money. I get positive feedback from clients and feel validated. It’s not perfect, but it’s something I can build on.

I still wonder what could have been with the first job, but I start to feel okay about things. I begin meditating again. I force myself to see some friends. I schedule my first meeting with a therapist for this coming Monday. I can sleep through the night.


TL;DR it’s been rough. I’m still trying to glean lessons from it all. I definitely need to seek out help faster next time I start spiraling. I also need to work on decoupling my self-worth from my finances.

Another lesson is that I either have to be doing something I enjoy or I have to be making a lot of money. There is no in-between. I need to sell a bit of my soul in a job and be okay with it or truly like what I’m doing. I know that’s some soft, weak, Millenial BS right there. I can imagine IlliniDave saying “there’s a reason they give you a paycheck on the way out and you don’t buy a ticket on the way in.” But it seems to be how I am wired.

The whole experience has given me a lot more empathy for people who get a little crazy over a job loss or a career setback. I read that over 10,000 suicides were attributed to the last financial crisis. When I originally read that it seemed so insane to me. I couldn’t imagine being that upset over financial turmoil. It just didn’t make sense, having never experienced anything even remotely like that. Now I see how it can happen.

Somehow through it all, with my freelancing and my wife being a rock with a great job, our net worth is at a rock solid $211,000. It seems so good now. I will work on appreciating it more.

Hopefully the next update will be cheerier! Keep on being awesome, forumites.

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Re: Smashter's Great Adventure

Post by prognastat » Thu Nov 08, 2018 10:15 pm

Sorry to hear that you've been going through some tough times. It sounds like you've gotten through the worst of it and things are looking up so I hope that things going that way moving forward.

Definitely developing some areas outside of work such as the meditation and focusing on friendships are good. Art least you are in a position where you weren't living paycheck to paycheck so that's something to be thankful for.

Hopefully your next update will include some successes on those fronts.

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Re: Smashter's Great Adventure

Post by Gravy Train » Fri Nov 09, 2018 4:03 pm

You're doing just fine, Smashter. Thanks to your forethought, determination, and follow-through to pay off your student loans early, you now have the freedom to say no to jobs and dance around a little bit before settling down for something. Most people don't have that freedom.

This part actually made me laugh out loud:
Smashter wrote:
Thu Nov 08, 2018 9:49 pm
I consider going back to sales just for money, but can't, having now told two separate jobs that I am leaving because I no longer want to do sales. I think a third time would qualify me as a sociopath.
Because I've done that, too, but for the legal world. I found that people really don't care. Most people are way too involved in their own lives to really give your motivations or decisions a second thought. Plus, Chicago is a big town. You'll probably never run into any of those people again anyway.

Good luck and chin up! You got this.

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Re: Smashter's Great Adventure

Post by Smashter » Wed Nov 14, 2018 11:46 am

@prog, thanks. I definitely have a lot to be grateful for.

@gravy, I appreciate that perspective. It's always good to hear from folks who have been through similar circumstances. Maybe the third change of mind is the charm :)

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Re: Smashter's Great Adventure

Post by Mister Imperceptible » Thu Nov 15, 2018 7:53 pm

Not sure there’s anything wrong with being a sociopath.

When was the last time you played a ballgame?

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Re: Smashter's Great Adventure

Post by Smashter » Fri Nov 16, 2018 5:36 pm

Fair point. Sometimes you gotta honor your inner Patrick Bateman. I was definitely catastrophizing.

I got a good bball run in yesterday, as a matter of fact! Played well, though that's not saying much since it was against a bunch of out of shape Jewish dudes. Their lack of positional awareness cracked me up. Nothing quite like watching a 5'8 guy mark out territory in the paint and demand the ball like he's Shaq.

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Re: Smashter's Great Adventure

Post by Smashter » Sat Nov 17, 2018 10:54 am

Jason wrote:
Sat Nov 17, 2018 10:10 am
A racist Jewish colleague of mine who loves to play the game is known to say "What makes LeBron James so good is that he learned to play the Jewish way"
That made me laugh out loud. I also thought you had to be exaggerating, but then I went down a Jewish bball history rabbit hole and found this interview with a filmmaker who made a movie about Jewish hoopers ( ... =123368994)
MARTIN: Oh, wow. Okay, there's is a term that you use in the film - and please, nobody, don't be mad at me, because this is a term that you use in the film. I'm just going to ask you what it's about. There's a term called Jew ball. What is Jew ball? Is that a mean term?

Mr. VYORST: No. I would hark back to your other question. That would be a proud term. I mean, I think basketball is cool. And there's a - you know, there's kind of a basketball chic and a basketball hip. So I think Jewish people are proud of playing basketball and their basketball heritage. But Jew ball's a type of basketball that I think was best exemplified by the 1970s New York Knicks, which is a team that I worshipped when I grew up, the Willis Reed-Walt Frazier teams that, you know, won two championships. And it stresses team play, five men playing together, tough defense, never slacking on defense and always hitting the open man on offense.
"Jew ball is best exemplified by a team starring 3 black dudes, a Catholic, and a Presbyterian" hmmmmmmm

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Re: Smashter's Great Adventure

Post by Jason » Sat Nov 17, 2018 11:09 am

a/k/a "Jew Ball is best exemplified by a team having no Jews."

RE: Lebron James being Bar Mitzvahed

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Re: Smashter's Great Adventure

Post by RFS » Thu Jul 18, 2019 12:03 pm

Smashter, I saw on the ERE Housing Approaches in Chicago thread that you moved about an hour north of Milwaukee and bought a house. How's all that going?!

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Re: Smashter's Great Adventure

Post by Smashter » Sat Jul 20, 2019 7:46 pm

Hey RFS, thanks for the nudge to write an update.

TLDR, it's all going pretty good!


We moved to this area after we found ourselves driving up from Chicago all the time and really loving it. Well, that coupled with the fact that Chicago just wasn’t clicking.

Living in the city was loud and stressful, but without the accompanying energy and vibrancy I felt while living and working in NYC. It was just flatter, more homogeneous demographically, and less interesting overall. Other than the awesome pickup basketball games I played in (and one fantastic ERE meetup :) ) I didn’t like the city.

Please take all that with a massive grain of salt. If you read up a few posts you’ll find the dark ramblings of a very depressed person. Depressed people can make even the best situations sound awful. So I don’t know how much of my bad experience was Chi just being a bad fit and how much I was just looking at things through sh*t-colored glasses. Probably much more of the latter.


I think I’ve talked about this before, but holy moly did cutting my income by 50k per year when I switched jobs affect me psychologically. I thought I was ready to take a stand against the man and do something that wasn’t as soul sucking as selling ads, but I wasn't. I got depressed and yearned for my old gig, which was gone forever. I should have figured this might happen, but hey, live and learn I guess.

I enjoyed this thread this thread , which discusses some of the pros and cons of sprinting to FI. I think I am mostly wired to sprint. I am much more of a sprinter athletically as well, as opposed to a distance athlete. I wonder if those proclivities are correlated at all.

I now have a fully remote job that is going pretty well. I got a raise recently, and I'm currently making 65k plus full benefits. I love the flexibility, and the fact that my dollars go so much farther out where I live now, but there are definitely still times when I question my decision to leave my more lucrative career. Major first world problems over here.


We bought a 1900 sq ft 3bed 2bath house in a quiet subdivision, very well maintained, for $245K. We put 60k down and took out a 30 year mortgage at a 4.25% interest rate. I went back and forth on whether to do a 15 or 30 year for a while, and got very stressed out about it.

I ultimately went with the 30 year mostly because I went down some MMM forum rabbit holes with people who are convinced it’s the better choice given my interest rate and investment strategy.

I’m already feeling a little uneasy about it.

On the one hand, there’s this part of me that’s like “damn, all I have to do is come up with $850 (+property taxes and utilities, but whatever) a month and I get this sweet house? Not bad!”

And there’s another part that hates debt with the burning fire of a thousand suns, and wants to pay this thing off as fast as possible.

We aren't saving as much money cause we're buying a bunch of house stuff, but that will settle down soon (I hope.) We are at about a 40k net worth with house debt factored in, and we're still investing in Tyler's Golden Butterfly.


Going from multiple big cities to a 50k person city has been a surprisingly easy transition. There is a great library, several lovely coffee shops, and even a really cool art museum. I have a good friend nearby, which is HUGE.


On the up and up. Partly because of…


My goal is to be less like my usual neurotic jewish self and more like Wendell Berry, or at least how he comes off in this New Yorker interview. ... dell-berry
One of the most significant themes of your recent work is debunking the myth of freedom—correcting the idea that limitless choice and limitless options make us happy.

It’s nothing we haven’t all heard before, but for some reason it really resonated with stuff I’ve been thinking about lately. When is it okay to accept that I’ve got a pretty good life? When am I going to stop thinking “I could have had X career, I could have married Y person, I could live in Z city, and everything would have been so awesome!”

I think a big part of my struggle, as pathetic as it probably sounds to people who don’t care about sports, is that I got to a very high level in basketball. I was a stud in my hometown, a sort of stud in college, and a non-stud playing overseas but the few stud moments I had felt incredibly, intoxicatingly good.

I haven’t found something that can replace those highs. And I think I change jobs and geographical areas so much because it gives me that burst of excitement that I so crave.

Then I start my new job, or I start living in my new place, and I find that none of it was a panacea. Then I decide it was actually so much better back where I was. Why didn’t I just stick with that?

Rinse and repeat.

What I’ve been thinking more about lately is the fact that part of the reason I liked basketball so much was that I was so committed to it. I chose something I was good at, I worked very hard at it, and I didn’t give up when times got tough. I pushed through tons of obstacles and always came out stronger. The mere fact that I was so committed made me so much better, and happier. This can get toxic if you try to hold on too long. But the core idea of picking something at a young age and seeing what would happen if I just committed to it was a good one, at least for me.

So while I’m not quite ready to commit to my current job with that same basketball zeal, I am with regards to my wife and my house. My wife and I have a very good relationship, to be clear. I just still, even two years in, can get in my head wondering if there might be someone even more perfect out there. It’s absurd. I feel so much better when I am just enjoying her company in the moment.

Barring some black swan, I want to stay at my place at least five years. I want to do some things in the community. I want to use the energy I normally burn ruminating towards making my current situation as good as it can be. I want to be Suo, basically.

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Re: Smashter's Great Adventure

Post by bigato » Sat Jul 20, 2019 8:23 pm

Do you think that describing you as a high achiever idealist would be fair? Do you consider yourself an idealist?

Other question: how much the image and identity that you project to other people is important to you? How important it is they recognize your merits?

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Re: Smashter's Great Adventure

Post by Smashter » Fri Jul 26, 2019 1:03 pm


those are some deep questions. I'd say that I was once a high achiever idealist who is now a low-achieving, overly pessimistic person who is struggling with being average. But I'm trying to change!

I'd also say that as much as I hate to admit it, the image I project to other people is important, and that I want them to recognize my merits. Having been a basketball star + Ivy League graduate, I am used to people being impressed by my abilities. Now I don't feel like I impress people (or myself) much. I know it shouldn't matter, but I'm not quite zen enough for that to be the case yet.

I am waiting for the next thing that really inspires me to just sort of come along. I know that's silly. I should be trying more things to speed the process up.

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Re: Smashter's Great Adventure

Post by bigato » Fri Jul 26, 2019 1:18 pm

I can definitely relate. It's so much easier to navigate life when there is a huge mission ahead. And as social creatures, the values we have and missions we take on are often subtly programmed in our minds over time by society through news, movies, social media, friends, etc. I know that I am vulnerable to this even though it seems to those around me that I have very strong, self-directed opinions.

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Re: Smashter's Great Adventure

Post by Smashter » Wed Oct 09, 2019 10:21 am

Job stuff

I've officially been at my most recent job for 6 months. This is a feat, considering my last few jobs went:

-Accepted offer for lucrative sales job in Chicago. Bailed the week before training was to start because I decided I couldn't bear doing another sales job, especially hawking annoying ads. Trying to have principals or whatever.

-Freelance writing. Dealt with the typical gig worker trials and tribulations: inconsistent work, horribly late payments, etc. No fun at all. Lasted 3 months.

-Full time writer for tech company in Chicago. Drank the kool aid (and free beer and sparkling water) for a while, but then really dreaded being in the office all the time. Did not like my manager. Did not enjoy the work. Did win company darts tournament the last week I was there.

So I took another writing job, this one fully remote. I was way too busy the first couple months and wasn't sure if I was going to survive, but things have calmed down and I don't actively want to quit at the moment. But things can change quick when I feel like I'm overworked and underpaid, so we'll see how it goes.

Now I'm trying to move back into sales. I applied for a newly opened role at my company that requires pretty much the exact background I have. That’d be cool cause it would be more money and I would free up some brain space to do more fun side writing again.

If the sales thing doesn’t work out and I continue to find the writing I’m doing incredibly dull, it might be time to consider new options once I hit the one year mark at this company.

I have a ton more experience now so I could try to freelance again with higher rates and a much more credible resume / endorsements. Or:
- I could try to join a local digital marketing firm to see if I’d like a tight knit office and the chance to grow a local business.
- I could try to coach basketball.
- I could just chill for a while and see what strikes my fancy.
- I could target something interesting and impactful on the 80,000 Hours job board. (would have to be remote, which limits options, but that board has some interesting stuff on it)

House stuff

We just refinanced to a 15 year mortgage at 3% interest and owe 180k on it. Every now and then I'm irrationally drawn to the idea of draining a lot of our accounts (we have 225k all in) and paying off the mortgage in one fell swoop. I just imagine having so much peace of mind with a paid off house. For whatever reason I would be much more likely to embrace a semi-ere, outside the box type approach if I had a paid off house. This is an attitude I need to work on.

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