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Week 23 of My $50 a Day Strategy Journey It Was Brutal but Worth It for Cheaper Shares

  • Writer: Silivere Bakomeza
    Silivere Bakomeza
  • Sep 27
  • 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 22 Strategy Investing Journey.



A Brutal Week That Tested My Conviction


This week tested my patience in a way few weeks have. The dip came hard and fast in just two days. Strategy fell sharply, dragging my portfolio down with it. Last week I was sitting at a negative 8.11 percent. This week I closed at a negative 12.28 percent, nearly four percent deeper in the red.


It was painful to see my portfolio fall back under seven thousand dollars after touching that milestone last week. That one stung. But here is what I realized: the pain is temporary; the shares are permanent.


Want to start your own investing streak? I use Robinhood for my $50 daily buys and Webull for tracking and analysis. Both give you free stocks when you sign up.


Week 23 of $50 a day Strategy investing journey showing 22.26 shares of MSTR and portfolio value progress. A real-time snapshot of consistent long-term investing discipline.
Week 23 of my 20 year $50 a day Strategy journey. The portfolio dipped this week, but the streak stays alive. Every buy is a brick; every share is a step toward freedom.

Portfolio Snapshot


  • Shares owned: 22.26

  • Portfolio value: 6,890.91

  • Current position: -12.28 percent overall


Every single buy adds to the total. Even when the value looks worse on paper, the share count keeps climbing. And that is the only scoreboard that matters in this system.


Bar and line chart showing Strategy Inc. investing journey from week 1 to week 23. Blue bars display total shares growing from 0.73 to 22.26 and green line shows portfolio value rising from 268 dollars to 6,890 dollars. Visual proof of consistent daily investing over 23 weeks.
Strategy journey from week 1 to week 23 shows steady share accumulation and portfolio value growth through $50 a day investing in Strategy Inc.

Why Checkpoints Matter


This week reminded me why checkpoints are so powerful.


At 20 shares, I told myself I had entered a new chapter. The next checkpoint is 25 shares and a portfolio value above ten thousand dollars. That will be the first time I step into five digit territory and hit one quarter of the 100 share target I set for this 20 year journey.


I am not there yet, but every dip brings me closer. Even when the price drops, the number of shares grows. These checkpoints keep me focused on progress, not pain.

Week 23 BakoBar performance chart comparing MicroStrategy, Bitcoin, QQQ, SPY, and Gold. MicroStrategy fell 11.35 percent, Bitcoin slipped 0.49 percent, QQQ rose 0.06 percent, SPY gained 0.17 percent, and Gold climbed 2.06 percent.
Week 23 BakoBar shows how MSTR compared against Bitcoin, QQQ, SPY, and Gold. MicroStrategy dropped sharply while Gold led the week, highlighting the importance of conviction and long-term focus.

Discipline Over Emotion


When the dip hit, I had the urge to buy extra. To load up while shares were cheap. But my rules stopped me. I signed a contract with myself to stick to 50 dollars a day, plus my Monday and holiday rules. That discipline kept me from overextending in the middle of a falling knife moment.


I see that restraint as strength, not weakness. Rules protect you from yourself. Without them, emotions would run the show.



The Bigger Picture


I am 23 weeks in, still negative overall, and yet mentally stronger than I was at the start. I know when the bull run comes, the cheap shares I am stacking now will accelerate my portfolio faster than I can imagine.


The path is not straight. The dips feel brutal. But this is what investing with conviction looks like. Ownership first, emotions second.



Lessons From Week 23


  1. Dips are painful but temporary

  2. Every share added today multiplies future upside

  3. Checkpoints make the journey bearable and motivating

  4. Rules and discipline matter more than feelings

  5. The reward comes not from reacting but from repeating



Final Word


This week was brutal, but it reminded me of something important: every 50-dollar buy is a brick in the foundation of wealth. The value may dip, but the ownership remains. And ownership compounds in silence until the market wakes up.


The pain is temporary; the conviction is permanent.


I started with Robinhood for simplicity and paired it with Webull for deeper tracking. If you want to add crypto exposure, Coinbase will give you $30 in Bitcoin when you sign up.



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 dollar 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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