Depressed Millionaire Syndrome: When Financial Security Brings Uncertainty

Gm, friends.

After years of grinding on CT, I suddenly found myself with more money—and fewer answers—than ever before.

These days, I’m wrestling with questions about motivation, direction, and what really matters now that the chase is over (or until I get new motivation).

In this reflection I am trying to figure out what comes next.

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Depressed Millionaire Syndrome: When Financial Security Brings Uncertainty

Thiccy wrote a good article the other day that resonated a lot with me. I’ll summarize the main points here first, and then we’ll jump into my side of this.

He reflects on taking a rare extended break after years of intense work as a trader, enjoying newfound freedom and comfort—symbolized by "silk pajamas"—but also feeling uncertain and unmotivated to return to the grind. Thiccy draws an analogy to NBA players, observing that both professional trading and basketball are ultra-competitive fields where early success and wealth can make continued hard work feel optional. Many NBA players, once financially secure, lose their drive, leading to short careers, while only a few veterans continue out of genuine love for the game (eg. LeBron James, Cobie, Jordan etc.).

Thiccy recognizes a similar crossroads in trading: after achieving financial security and fulfilling personal goals, the motivation to keep pushing fades, and the emotional highs and lows of the game change. To sustain a long career, the need to shift from relying on sheer effort to focusing on craft, mentorship, and self-care, mirroring how veteran NBA players adapt their game as they age.

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Okay, so about my journey. 2024 was a great year for me, a breakthrough year kind of. I did some venture deals that took off (literally), and I earned too much money, too fast. I also experienced this kind of exponential growth in 2021, but now once again in 2024 (at a higher level). Anyway, not trying to brag here. Even though it sounds braggy. So to the point. I started feeling it by the end of 2024 and basically all of 2025, that I lacked motivation. Lacked motivation to trade, to take big risks, to try new crypto stuff and DeFi protocols, to produce content on Twitter. I suddenly felt no need to do anything. Every day was the same. Obviously, I didn’t give up things, but I have not run my machine at full speed.

Anyway, this led me to rethink everything. In my earlier life, when I worked a stable 9-5 job, there really wasn’t much option about what to do: stay in my lane, stay in my city, do the same stuff for 40 years, get kids, and die. Not that this is a bad life at all. It’s just that now with all my new options, I am having trouble deciding on anything. Which leads me to not taking a decision at all (however, not choosing anything is a decision too). I have come to a point where I don’t know where to live, nor do I know if I will stay in my country or somewhere else.

Obviously, I am thinking about taxes, but lately I started to think more about where I actually want to live, regardless of this. Maybe a solution is 5-6 months in my home country, and the other 6-7 months somewhere else. Tbh, I am not really keen on traveling much. I feel I’ve seen an ok amount of the world already. I like to stay in places for a long time. So I am also considering whether I am going to sell my real estate here, buy more or just do nothing. Fuck, I hate being a whiny bitch. But I just can’t take a decison. Depressed millionaire syndrome is real.

I miss the obsession I had for the game. The days were I was so glued to the screen that nothing else mattered. These days will come again, but I just don’t know when and how. I think I have to be bored enough first. I tweeted about this a while ago, see below:

Maybe I am in fact in the middle of a new pivot. A new direction. I just simply don’t know what I will pivot to yet. Maybe I am tired of this because of the lack of a real bull run. Maybe I would have been motivated if we were up only. I don’t know really. I am fluid and go where the road takes me in terms of market direction.

Another thing I kind of miss is how my attention span used to be. After crypto and the constant action in this space, crypto rewired my brain for short-form content and constant alerts, making it difficult to focus deeply or engage in longer reading. I used to read long books and could be undistracted for hours. Now, I can’t even stay focused for more than some minutes.

Well, just to summarize. I am still thinking a lot these days, and I am not sure what is next. I am going to take my time. Not in a hurry. I also assume the markets will be quite slow during the summer, so there won’t be any FOMO. But I will stay focused. Remember how many were sidelined end of July 2021 when we got a second leg of the bull run. I still have a tiny hope we see something similar. But if not, then it’s okay. I am still happy with my gains this cycle.

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That’s it for today.

See you next week!

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