This post is spot on. Have had several hit the wall and just say, “its not worth the risk and busting my ass doesn’t move the needle anymore.”

If someone is an A player it really chaps their ass. They know that they didn’t leave it all out on the field.

I suspect this is a big factor in mid-life crises. Coping mechanisms break down as illusions fracture.

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Jan 10, 2023Liked by BowTied Bull

There is something to be said about recognizing you are in nomans land, and simply relying on your WiFi income to maintain lifestyle IMO. Good year...awesome. Bad year...who cares. Just gotta get off the treadmill of trying to keep getting more rich. Its a hard one...deciding you are rich enough that is. Rich enough + unlimited flex from wifi income = winning.

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Growing up surrounded by 'friends' who would absolutely steal from you if they thought you had anything nice, you have no interest in flexing.

Much prefer to downplay any wealth and success. See so many people who don't even make 1/2 of what we make spending it on looking rich. And then tell us 'if you do x, you can get a pair of $250 shows too".

Smile. nod. agree.

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This post is spot on. There is no excuse if born in the USA. I was born in South Sudan where constant gun shots and shelling was the norm. Luckily I survived and moved to the USA in 2016 for college. I just grinded and still grind(120hours a week). No excuses. So many people dont realize how good they have it here.

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post is dumb accurate.

also: people who *come* from wealth (and managed to stay/increase their own money, not just trusties who live off granddad or whatever) frequently don't stunt at all. not even the watch. Old Money very rarely flexes.

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I recently listened to a podcast with journaling advice, and they suggested 5 daily prompts (which, as I look at them, are very similar to Bull's 4-5 sentences about what is/isn't going well, and your general headspace):

-What is exciting me?

-What am I doing to move the needle?

-What am I learning?

-What is draining my energy?

-What am I grateful for?

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Long time lurker. Appreciate everything.

Would love to see a post at some point on how to value your own company for an exit.

Then potential after sale roadmap so you don't piss away the hard work.

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Great post. If anyone reading this leveled up significantly in 2020-2021, you probably spent 2022 navigating the unfamiliar traps at the new level you got to(Just me?). 2023 is the year of leveling up again, so be ready for all of the new traps that come at that next level. Hopefully this lit a fire under everyone’s ass if any complacency was setting in.

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Always enjoy your wealth analyses. Living in a very wealthy area, I thought I would provide a few more categories of wealth I see all the time (although admittedly probably don’t exist as much in Tier 2 cities). First, there is a level of stratospheric wealth that has been created in the past 10 years (and even more dramatically in the past 5 years) if you were in the right place in Tech. I know many people who went from a few million in net worth to a few hundred million in net worth in the span of a few years. They live in $30mm homes and aren’t shy about their wealth. They want to be billionaires. Second, there are many old money wealthy people who trade on their existing network to create even more wealth through investing (not in a bad way, but doing the least amount of effort for max gain). In other words, rich get richer. Third, there are many old money people who appear wealthy, but the story is complicated. They live in a $5mm house, but cannot afford the upkeep, can’t go out to dinner, don’t travel, etc. Maybe they have a trust fund they can’t access. Either way, they cannot live the same lifestyle to which they are accustomed. This is quite common.

I know you are most focused on people building wealth, but wanted to provide another angle. Wealth scales and getting off the hedonic treadmill is difficult if you live among other wealthy people no matter where on the chart you fall. Someone always has more. Unless you are Elon. And even those guys at the top want to be #1.

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This is spot on - pretty much described my situation 1:1

I'm 34 y/o and the golden handcuffs are real. I did start a successful ecom 7 years ago - let SO run it after a year or so and it stagnated.

Had another wifibiz - paintball field. Not compatible with babies, so I shut it down.

Now at the third attempt - another ecom as well as recruitment agency in the making. Ecom with an aim for the exit, recruitment to 2-3x my primary income.

Thanks Bull - you're an inspiration and one of the reasons I did make the attempts :)


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Very well done. The upper middle is crazy easy to get stuck in. House, wife, kids, private school, country club, vacations, new cars every 3-5 years. See it all the time and candidly focused on avoiding it myself. Not a terrible life, but easy to get stuck and feel like you left chips and effort on the table I imagine....

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I love your post because of the perspective it brings me, I have no one to have these convos with. 25yr old nurse, whole family of nurses, immigrants, when it works for one we all followed. Jumping into medical sales this year, thanks to your advice. Secure 6 figs and ecom, 2023

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Given how frequently "watches" appear in your social/cultural write ups, I'm dying to know if you are an apple watch guy, something basic (timex), or some obscure nice mechanical watch that doesn't attract attention?

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im the opposite of most "ideas men" - I feel confident I can validate/start/run with an idea but not good about coming up with one. Can the jungle do a post on wifi money ideas? Maybe I'm still not realizing how "small" one can start with

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But what is the point of all the hard work and then getting rich apart from the freedom? If you drove a beat up old car forever to keep expenses down and then you make it and want to finally fulfill a childhood dream of buying a Porsche but you can't because you risk becoming a target? Same with a nice house? Is enjoying ones wealth really a fools game?

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Great post. I ended up her on a Ross Douhat link and subscribed immediately after reading! I found myself out of a job and in No Man's Land four years ago at age 52. My wife was still working and did until last year. Thanks to my spreadsheet that confirmed the 4% rule paradox you described and some lifestyle changes (we sold the house and moved to a new home closer to family and in a lower-cost area). We decided that NML is a great place to be.

The only two downsides are (1) 2022 sucked for the IRA's and there will always be fear of what the spreadsheet says if we have a few more -18% years, and, (2) the shame induced by being a 50-something life-long striver when people ask you what you do for a living and having to admit you are retired. No Man's Land seems to be a relatively lonely place. It's another form of "taking a risk," because not many seem to choose it.

Oh well, I enjoy being able to read lots of Substacks, going to the gym, and golfing. Thanks for writing this post and I look forward to reading others.

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