Year-End Tax Planning Checklist for High-Net-Worth Investors
Most tax strategies must be implemented before the calendar year ends — not when you file your return. By the time your CPA is preparing your taxes, the window for many of the most impactful moves has already closed. Now is when proactive planning happens.
Review Your Capital Gains Position
Identify any realized or anticipated capital gains for the year. Look for offsetting losses in your portfolio — tax-loss harvesting can reduce your net gain exposure.
If you have gains from a real estate sale, evaluate whether a 1031 exchange or Qualified Opportunity Zone investment can defer or reduce the tax before the year ends.
Evaluate Qualified Opportunity Zone Timing
Capital gains must be reinvested into a Qualified Opportunity Fund within 180 days of the triggering event. If you had a qualifying gain earlier in the year, confirm whether the reinvestment window is still open.
Do not assume the deadline has passed — calculate it precisely and act before it closes.
Max Out Tax-Advantaged Accounts
Confirm that contributions to retirement accounts — 401(k), SEP-IRA, defined benefit plans — are on track to reach the maximum allowable amounts for the year.
For business owners, certain retirement plan structures can shelter significant income. Your CPA can help identify whether you are leaving deductions on the table.
Review Business Income and Deduction Timing
If you are a business owner, consider whether accelerating deductions or deferring income into the following year makes sense given your current and projected tax rates.
If you have an 831(b) captive arrangement, confirm that premiums have been paid and documented appropriately before year-end.
Charitable Giving
Contributions to Donor Advised Funds before December 31 are deductible in the current tax year. Donating appreciated assets — rather than cash — can eliminate capital gains tax on the donated amount while still generating a full deduction.
Bunching multiple years of charitable giving into a single year using a DAF can also maximize the deduction benefit.
How True North Private Investments Helps
At True North Private Investments, we work alongside CPAs and financial advisors to help high-net-worth investors implement tax-aware strategies before year-end. From 1031 exchanges and DSTs to Qualified Opportunity Funds and energy investments, we help identify the right tools for your situation.
Final Thoughts
The best tax outcomes are not the result of last-minute decisions. They are the result of a plan that was built and executed before the year closed. The checklist above is a starting point — but the real work happens in conversation with your advisors.
Schedule a conversation with True North Private Investments before the year ends.