🔺 r/personalfinanceuAlternative_Olive861·14 days ago
Turning 40 in Dec, feeling embarrassed, ashamed, & defeated by active stock picking. Looking to clean up my portfolio...
Hey everyone, I'm turning 40 at the end of 2026 and feel filled with regret and embarrassment about my portfolio. I thought I was smarter than the market as a "value investor," and I failed miserably. My goal was to retire by 50-ish off dividend income. Back in 2021, I went big into BABA and China (~$100k position) hoping to buy a house with the proceeds. That failed, and while I caught some gains in 2025/2026, I heavily underperformed. I'm a business owner netting $9k–$10k/month after taxes in a HCOL area, saving 40–50% of my income. Since Jan 2021, my portfolio annualized return is a pathetic 5.29% (34.25% cumulative) vs. the S&P roaring ahead. Net contributions: ~$518k | Ending balance: ~$651k. Seeing how much I left on the table during a massive bull run makes me sick, and emotionally I am just done. I want simple, boring, and automated. I’m ready to drop the ego, take my L's, and move the F*CK on. CURRENT PORTFOLIO BREAKDOWN (~$651k Total): Individual Equities (~31% / $202k): • ADBE ($76k, -$19.5k loss) • BABA ($45k, -$7.2k loss) • NOW ($28k, +$7.2k gain)* • O ($14k, +$686 gain) • LAC ($26k, -$13.7k loss)* • LAR ($10.6k, -$1.8k loss)* *I feel comfortable letting these thre…