Mid-Year Portfolio Checkup. Are You on Track to Hit Your Goals?
Evaluate allocation, rebalance smartly, and harvest losses before Q4 volatility.
If you run a business, your portfolio is your second P&L—one you can’t afford to manage on autopilot. Mid-year is the natural audit: markets have moved, cash balances have changed, distributions are on the calendar, and what looked “about right” in January may now be too risky, too conservative, or too expensive after tax. This is where entrepreneurs either tighten the screws—or let drift, taxes, and fees quietly siphon five figures.
Think like an operator. You’d never let your gross margins compress for six months without investigating; don’t let your risk budget, concentration, and tax drag do it either. Are the returns your strategy can reasonably deliver still aligned with the return your goal requires? Has a handful of positions swollen into a hidden concentration? Is your cash tasking the portfolio at today’s rates, or sitting idle while inflation nibbles?
Mid-year is for deliberate course corrections, not heroics. You translate goals into numbers, re-underwrite your mix, and use cash flows—not taxable sales—wherever possible to get back to policy weights. You pressure-test asset location, harvest losses without losing exposure, and schedule the moves that reduce surprises when Q4 volatility and year-end distributions arrive.
What follows is a rigorous, entrepreneur-friendly framework you can run in an afternoon to verify you’re on track, cut avoidable taxes, and position intelligently for a choppy Q4—with just enough precision to matter and no theatrics.
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1) Re-forecast the goal: “Am I still on pace?”
Translate goals into dollars and dates. Pick the goal that matters (e.g., $5.0M liquid by 2032). Compute the required annualized return from today to the goal date, then compare it to the expected return of your current mix.
Example. You’re at $3.2M today, target is $5.0M by Dec-2032 (7.4 years). The forward return you need is roughly 6.3% annualized. If your current mix reasonably projects to 5.4% net of fees and taxes, you’re under-earning the goal; nudge risk up intentionally (within your drawdown tolerance) or increase savings.
Why this matters for founders: your business cash flows are lumpy. Front-load contributions after strong quarters and throttle back after slow ones—but keep the portfolio’s risk budget stable. That keeps the investing engine compounding while the operating engine fluctuates.