Week 22 of My 20 Year $50 a Day Strategy Journey Steady Growth Toward the Next Checkpoint
- Silivere Bakomeza
- Sep 20
- 3 min read
This post is part of my ongoing 20 year, 50 dollars a day investing series in Strategy (MSTR). Each week I document the streak, the share growth, the portfolio value, and the discipline behind the system. You can read last week’s update here: Week 21 Strategy Update.
Another Week Another Step Closer
This was the first week my portfolio touched $7,000. Strangely, I did not feel much of a milestone because in my mind the real checkpoints are still ahead $10K for the first five-digit portfolio and 25 shares which mark a quarter of the 100-share target.
Still, the feeling is good. I know I am getting closer, and each week of ownership builds the foundation for those bigger milestones.

Building Shares and Value Week After Week
Twenty-two weeks in, it sometimes feels like I have been doing this forever. But when I zoom out, I realize the journey is still young. This is only the start of a 20-year system and there is plenty left to prove to myself.
The difference is clear though every single week I own more. That ownership is what compounds, not emotions.

If you want to see where this all started check out The First Share of My Strategy Journey.
And if you want the full blueprint my Strategy DCA Flagship Post breaks it all down step by step.
What the Market Gave This Week
The Fed cut interest rates by 0.25 percent this week and the market reacted. Strategy closed stronger and even though my portfolio is still in the negative it is improving.
Last week I was down 12.28 percent. This week it closed at -8.11 percent. Not yet green but definitely moving in the right direction.

For context you can also read about Week 10 of My Journey when I crossed 10 shares. That milestone was the first real psychological checkpoint.
The Discipline That Matters
Twenty-two weeks means I have bought every single day for over five months including weekends and holidays. That is what separates speculators from builders.
The one lesson I keep coming back to is this
Adopt a system
Invest intentionally not emotionally
Give it time for your investments to mature
When you do that checkpoints stop feeling like pressure. They become proof.
The Road Ahead
$10,000 portfolio value my first five-digit milestone
25 shares a quarter of the way to 100
This week was simply one more brick in the foundation. Ownership is stacking, emotions are quiet, and the system is carrying me forward.
FAQ
Q: Do you ever time the market
No. I buy daily 365 days a year. My system is about removing emotion and letting discipline win.
Q: How can I set up something like this
You can start with as little as $1. Tools I use include
Robinhood for automated daily investing
Webull for tracking growth and getting free stocks
Acorns for passive round ups
Coinbase for crypto exposure
Crypto.com for global reach
Q: Why Strategy and not another stock
Because it gives me long term Bitcoin exposure through ownership while also letting me track share accumulation as a psychological anchor.
Final Word
22 weeks in, I know this the system works. Not because I am rich yet but because I am consistent. The checkpoints will come $10K ,25 shares, 50 shares ,100 shares. What matters is I am still here still buying still building.
If you want to see how this looks in the long run bookmark my full Strategy DCA System Post. That is the playbook behind every weekly update.
This journey is for the underdogs and 9-to-5 workers who are told wealth is out of reach. It is not about timing the market, it is about proving that discipline beats emotion. Every $50 buy is a receipt of ownership, a brick in the foundation of long-term wealth. If you want to follow along, subscribe to my weekly updates and join me as I build this position one share at a time.
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