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Top Content
5 “Once In A Lifetime Events…”
It’s early, but I’d make the argument the video below is on pace to be my most viral video ever. To date, I’ve had about 10 posts achieve over 1M views, impressions, etc. Only a few crack into the 2M+ window.
This has been the only time, where only 12hrs later, does a video have over 2M views. See for yourself👇
Main Story:
The $50,000 Shrug
It is 2 PM on a Wednesday and I am currently staring at a week that makes absolutely no sense.
If you looked at my calendar or my bank account over the last 24 hours, you would think I am either a genius or a complete disaster, and the truth is probably somewhere in the middle.
It all really started last Friday when I was sitting across from my financial advisor. We were going over some new investment stuff, talking about cash flow, and he kept circling back to one question: Why am I so adamant about holding 20k in cash at all times? He knows the math. I know the math. But the math doesn't account for the period in my mid-20s when I went from making 250k a year to making less than 15k. I spent 18 months stretching that 15k while living in a buddy’s rental property in a part of town I wouldn’t recommend. I launched a business from a room where the only thing I owned was a makeshift standing desk built on top of the same desk I had in college. That desk followed me through New York, Chicago, and Indianapolis before I finally trashed it in 2022. During the meeting, I almost broke down in tears just talking about it. I recognize not everyone needs an advisor, but sometimes the job isn't about maximizing returns. It is about striking a balance between what the spreadsheet says and what allows you to sleep at night without smelling that old rental property.
Financial plans aren't built on spreadsheets; they're built on the scars of your worst year.
By Monday morning, the universe decided to test that "sleep at night" theory.
I got my tax return back from my accountant. I didn't even want to look at it. I just forwarded it to my advisor because I was fully prepared to see a 15k or 20k bill staring back at me. For context, about 50% of my income these days comes from things outside of Habits (brand partnerships, consulting, and whatever else I can grind out outside my 9-5).
After a quick call, it turned out I wasn't paying 15k; I was actually getting a modest refund. My partner joked that it’s annoying how I’ll just dump that "found" money into investments and never touch it for decades, and she’s right. But the celebration lasted about 20 minutes.
By lunchtime, I got an alert that a 15k commission check from a long-term partner was 60 days overdue. I reached out and they essentially told me they’re going bankrupt and shutting down. Then, another consulting gig I’ve been working on for 18 months told me they’re pausing our (new) ~20k agreement because of budget cuts. I’m not going to sue anyone or throw a fit. That is just the game. You shrug your shoulders, say "well, fuck," and keep moving.
Entrepreneurship is mostly just agreeing to get punched in the face in exchange for the right to keep playing.
While my income was taking a 40k hit in the span of a few hours, my phone was blowing up for a completely different reason.
I posted a video last night about the millennial thought process, and as I write this, it has 3M views. It’ll probably hit 6M by tomorrow. Naturally, I forgot to organize the backend properly, so I’m scrambling to fix a messy CTA to Habits while the iron is hot.
Meanwhile, because life doesn't care about your business pivots, it is also the Sweet Sixteen for March Madness. I am currently in our little 1bd apartment in Houston (which is our latest "venture" and a nice change of pace) and I’ve volunteered to host a bunch of friends and their significant others. This also means dropping a decent chunk of change on tickets for Iowa, Nebraska, Houston, and Illinois because I want to show my friends a good time in a city they've never seen.
At the same time, a startup organization in the UK just asked me to fly out in August to mentor their accelerator. It is a chance to see old JPMorgan friends in London and visit some of our employees. It is chaotic, it is expensive, and it is exactly the kind of random memory that makes a career feel like it's actually happening.
The highlight reel always looks cleaner than the room where it was filmed.
I share this because I think we all show up to work or social events trying to pretend we have it all together. But the truth is that your mindset varies day to day, maybe even hour by hour.
My life is chaotic right now, but I’d argue it is no more chaotic than yours.
If you have kids, your whole world flips when a daycare call comes in at 10 AM. If you have older relatives, one phone call can change your entire month.
We’re all out here trying to eat right, exercise, be present for our families, and find the balance between spending for today and saving for a tomorrow we aren't even guaranteed to see.
Sometimes you just have to tell yourself that today was really hard, but the year has been pretty great. Or you do what I do and email your financial advisor just to validate that you aren't being a total moron with your choices.
Where I’m getting at…we are all just trying hard and attempting to avoid the big screw-ups that actually break the machine. If you’re doing your best, give yourself some peace. I’m rooting for you.
Life isn't about having it all together; it's about showing up when you're falling apart.
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