48 Comments

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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Suspect that as well. It's a weird mechanism where the first 10 years your net worth is going up huge. $50K to $100K to $200K are all 100% moves

Then you hit $1M and the next $100K is only 10% which becomes very hard to "save into"

Also agree that the top guys usually have that nagging feeling in the back of their head

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Sure. The midlife crisis occurs when you’ve topped out. Happens in medicine and law especially.

Go through all that training, hit all the milestones, finally make partner and...now what? You’re 35-45. You’ve climbed the mountain, looked around, said “neat” then “now what?”

The $ isn’t motivating anymore. Treading water at your topped out spot for another 20 years doesn’t appeal, but neither does risking the job you worked for.

The good news is the crisis is a tremendous opportunity for reinvention. If you take care of yourself, you are healthy with $ and the world at your fingertips. Congrats, you can reset the game and do another playthrough with all your accumulated power-ups. Few.

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This one hits hard. My coping mechanism is that i allow myself to take more time to spend with family/kids as well as focus on personal health. Yet, i still have the nagging feeling that I am underachieving as a Man... in a big way.

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Been there. After time spent trying to avoid or reason away the feeling, spent time processing it. Imagine you’re ill and the feeling is a glass of unpleasant medicine you have to drink. It’s trying to help you.

After you swallow it, your vision will clear and you’ll see a path forward.. Gurus do not have your answer.

*float tank sessions helped. No distractions, just time to think.

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Thats your ego talking. The ego is not your amigo...

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Could be. It’s an indicator something is out of alignment. Which is ok. Problems can be solved.

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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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Truth.

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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Yeah it's why we laugh at people who flex then claim they grew up poor. Just announcing you grew up middle class, which is fine but no need to BS and say you didn't know the number one rule "don't be caught slipping"

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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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Yep.

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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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Yeah we're actually working on that in the background. Valuations down after interest rates up. If you do care all you have to do is go on empire flippers and see the latest sales by sector

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Your company exit value is set by the market. You can influence it through good marketing, positioning and negotiation. I wrote about my major takeaways selling my biz here: https://charlesdart.substack.com/p/top-small-business-m-and-a-takeaways

Hope it helps.

Now tryna figure out how to deploy the cash, conserve and grow. We’re following the pattern “spend time with family” lol. Got 4 kids and homeschool.

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Quite common once in the 8-digit range!

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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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Yep agree

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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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yeah that's all true. We're just laying out the math on why golden handcuffs occur.

If you're worth $2-3M and make even $600K that's $300 after tax if you spend half of it thats $150K... You're moving single digits in percent terms. Mental break point is around 4%.

IE. if you have $5M it's really tough to work an entire year for 60+ hours just to move it by $200K

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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 :)

GM

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Congrats!

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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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Ser homeless people don't wear anything worth more than $10

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Sundial on the beach. I like it.

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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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Its more about finding problems than ideas . Do more stuff and you will find more problems then you can try to sell a solution. Hard, urgent and recognized are the best (lose weight, find mate, get muscule, makeup, status good, entertainment/bet/casino). Create a better product or service than existing or help business to do it

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if youre a paid sub, check the zero to hero ecom post. btb addresses this quite well

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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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Sounds like you've never made it. That's all we can tell from this. You end up buying the toys and returning them after a couple years.

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Well yes. Otherwise I wouldn't ask. I made it from poor (and alcoholic family) to middle class (120k per year) and am working on the next step. I read Felix Denis book twice (it's really that good) and he warned and even advised strongly against wanting to become rich and stop at 40 Million because there is no return after. He also said everyone goes through burning tons of money on fancy crap and it's better to get that out of your system early. It's a fascinating topic. Might be worth a blog post.

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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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