At the beginning of 2025, I launched Project 350K (as outlined in parts 1, 2, and 3) with an ambitious goal: to grow my Traditional IRA to $350,000 over ten years. Unlike my much larger trading account, which holds a broader mix of growth and income-producing investments, my Traditional IRA is a dedicated growth-oriented portfolio. The project was designed to test my ability to generate alpha through concentrated stock picking, while maintaining guardrails for capital preservation and holding myself accountable for the investment decisions made along the way.
My 2025 review was disappointing. The portfolio declined 4.5%, substantially underperforming both the S&P 500 and Nasdaq 100. I identified several shortcomings, including premature capital deployment, poorly timed investments, and a tendency to allow conviction to outrun evidence.
Ten months into 2026, the results have improved, though hardly spectacularly. More importantly, I am beginning to see how my investing philosophy is evolving, particularly in how I assess risk, allocate capital, and manage my own psychological blind spots.
Hard Facts: Performance Through October 30, 2026
As of October 30, 2026, my Traditional IRA generated an annualized return of 8.2%. This is an improvement over 2025, but the portfolio still trails the broader market. The S&P 500 and Nasdaq 100 had returned around 13% and 15% annualized, respectively. For a portfolio designed to generate alpha, that is disappointing. It also remains below the roughly 14% annualized return originally contemplated for Project 350K.
The account remains concentrated, with Amazon AMZN 0.00%↑ representing 40% of its value, followed by Life Time LTH 0.00%↑ at 18% and Shopify SHOP 0.00%↑ at 13%. The largest positive contributor was Life Time, up almost 50% from my average cost, followed by Salesforce with around 24%. Amazon, with the recent selloff post Q3 results, dragged down overall portfolio returns this year, albeit still up 4% this year.
The lesson is that identifying a few successful investments isn't enough. Their contributions must also overcome losses elsewhere in the portfolio.
Capital Allocation: The Winners, Losers, and Rotations
One adjustment I introduced in 2026 was selectively using opportunistic trades to enhance returns and make better use of limited capital. Three capital rotations illustrate both the promise and limitations of that approach.
Floor & Decor to Life Time: A Successful Reallocation
In January, I sold 25 shares of Floor & Decor FND 0.00%↑ at $65, realizing a loss of approximately 45% relative to my original cost. Together with the capital injection set aside for Q1 2026 deployment, I subsequently purchased 60 additional shares of Life Time at $26.50, alongside additional shares in Salesforce and Elastic ESTC 0.00%↑ (more on Elastic below). This proved to be a highly successful reallocation. Life Time has since appreciated substantially, supported by strong operating results, pricing power, and growing engagement among its premium membership base. My original investment thesis was based on the company’s ability to evolve beyond a conventional gym chain into a premium lifestyle and wellness platform. The important lesson is that realizing a loss need not represent a poor decision. Sometimes the greater mistake is retaining an underperforming investment when a more compelling opportunity exists elsewhere.
Elastic to McDonald’s: When Conviction Wavers
In January, I purchased 25 shares of Elastic at $68, viewing it as a small speculative position with recovery potential. I had previously held a much larger position in the company for five years, generating an uninspiring annualized return of approximately 1%.
Despite my familiarity with the business, my conviction wavered when the stock fell further after I bought. As it recovered, I placed a sell order targeting a 15% profit (to match my roughly 14% annualized return originally contemplated for Project 350K), which eventually executed at $78.50.
In hindsight, my exit was driven less by a reassessment of the company’s fundamentals than by a desire to secure a satisfactory return after months of uncertainty. Elastic subsequently appreciated further.
I redeployed capital into McDonald’s MCD 0.00%↑, an established consumer franchise whose depressed valuation I believed offered an attractive risk-reward proposition. While McDonald’s has remained largely flat, I remain comfortable with its longer-term prospects.
The lesson is not that I should have held Elastic indefinitely. Rather, I showed discipline in sizing the speculative position, but perhaps less discipline in deciding when to exit. Securing a 15% profit was reassuring, but reassurance and sound investment judgment are not the same.
Lululemon to Life Time: Conviction Matters More Than Anchoring
In September, I sold my remaining 17 shares of Lululemon LULU 0.00%↑ at $96.25, crystallizing a loss exceeding 60% relative to my average purchase price. My conviction had deteriorated as revenue growth slowed and competitive pressures raised increasingly serious questions about the company’s long-term fundamentals. I redeployed the proceeds into additional Life Time shares at an average price of $39.50.
Interestingly, Lululemon subsequently recovered, and the returns from retaining it would have been roughly comparable to those generated by the additional Life Time investment, at least through October. Nevertheless, I remain comfortable with the decision. Lululemon’s investment thesis had weakened, while Life Time’s continued to strengthen. Holding onto a company merely because its stock price had fallen would have been anchoring, not discipline.
Conviction Holdings: That Includes Trupanion (Maybe)
Amazon remains my largest position and the anchor of Project 350K. I continue to believe it offers an exceptional combination of consumer exposure through retail, Prime, and advertising, alongside technology infrastructure through AWS. Its recent Q3 results highlighted the tension between strong underlying operating performance and massive capital investment. AWS revenue grew approximately 39%, while overall operating margins reached a record 13.9%. However, the scale of AI infrastructure spending has raised understandable concerns about future free cash flow.
I have no intention of exiting Amazon based on short-term market reactions. That said, its concentration in my IRA makes the opportunity cost of underperformance impossible to ignore.
Meanwhile, my conviction in Salesforce has been rewarded. I progressively increased my position as the share price fell from $220 to $160, lowering my average cost to approximately $185. My longstanding investment thesis centers on Salesforce’s transition toward greater profitability, operating discipline, and shareholder returns.
Trupanion TRUP 0.00%↑ presents a more difficult question.
I increased my position at $25 in April, bringing my average cost to $30. While its subscription margins have been recovering, the share price has remained disappointing. With Q3 results scheduled for November 5, I intend to reassess the investment before deciding whether to continue holding or redeploy capital elsewhere. Alphabet GOOG 0.00%↑, another established business experiencing negative sentiment, is one potential alternative.
The challenge is determining whether Trupanion’s weak share-price performance reflects a deteriorating thesis or simply an opportunity that requires more patience.
Suit Yourself: Recognizing My Blind Spots
One of the central ideas in my book, Suit Yourself: A Portfolio Strategy for Every Personality Type, is that understanding our investing personalities requires recognizing not only our strengths, but also the blind spots that accompany them.
Suit Yourself Is Now Out!
After years of reflection and writing, my debut book, Suit Yourself: A Portfolio Strategy for Every Personality Type, is finally out, published through Koehler Books. This side passion project brings together my professional and personal journey across psychology, personal finance, and the many ways our identities shape how we invest.
As an Enneagram Type 5, I am naturally drawn to researching businesses, developing independent convictions, and identifying opportunities others may overlook. That curiosity has helped me discover companies such as Life Time, but it has also drawn me toward smaller, complex businesses where the intellectual appeal sometimes exceeded the financial reward. My previous experience with Elastic is a good example. I am increasingly recognizing the difference between understanding a company and having a compelling reason to own its stock. That distinction is influencing how I allocate capital.
I remain interested in smaller companies with attractive growth prospects, but I am becoming more comfortable prioritizing established businesses with proven economics, particularly when temporary market pessimism creates attractive entry points. My recent McDonald’s purchases and interest in Alphabet GOOG 0.00%↑ and Netflix NFLX 0.00%↑ reflect this evolution.
Yet self-awareness also requires questioning whether my growing preference for established businesses represents genuine improvement in risk discipline or simply a different psychological comfort zone. Familiarity is not the same as safety, just as conviction is not the same as being right.
That is perhaps the most important lesson from this year’s review.
Looking Ahead to 2027
Project 350K remains an ambitious undertaking. I do not intend to abandon active stock picking, but the results from the first two years reinforce the need for a more disciplined approach.
My priorities for 2027 are straightforward:
Maintain conviction, but challenge it regularly. Continue holding businesses with durable competitive advantages, but reassess assumptions when operating fundamentals change.
Be more deliberate about capital rotations. Justify every sale and replacement with improved prospective risk-adjusted returns, not simply the attraction of a new investment idea.
Distinguish speculation from long-term ownership. Size and manage smaller, opportunistic positions differently from established businesses intended for long-term compounding.
Remain accountable to the benchmark. Intellectual satisfaction is not a substitute for investment performance. If active management consistently fails to justify the additional complexity, greater index exposure deserves serious consideration.
In my earlier reflection on stock picking and Lumentum, I wrote about the importance of balancing conviction with humility. That principle remains central to how I want to invest. The goal is not to eliminate mistakes or predict every winner. It is to recognize the behavioral tendencies that lead to unnecessary errors, improve the quality of my decisions, and build a portfolio that reflects both my ambitions and my limitations.
After all, that is what my book, Suit Yourself, is ultimately about.
2026 has delivered better returns than 2025, but not the alpha I had hoped for. It has, however, provided another year of evidence about how I think, where I succeed, and where I still need to improve. And if Project 350K is as much about becoming a better investor as it is about reaching a particular number, those lessons are worth keeping.
Follow me on X.com (formerly Twitter) @ConsumeOwnTech and Yahoo Finance. My book, Suit Yourself: A Portfolio Strategy for Every Personality Type, blends Enneagram psychology, pop culture, and behavioral finance to offer a personalized roadmap to investing. Learn more at my author page or order the book on Amazon.
This is the last article for 2026; the next one will appear at the end of January 2027.
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