Avi Kantor | Sep 01 2025 15:00
Year-End Tax Planning & Tax-Loss Harvesting: Smart Moves Before December 31
As the year winds down, it’s easy to focus on holidays and travel and put taxes on the back burner. But for many families and business owners in places like King of Prussia, Wayne, Norristown, and Conshohocken, thoughtful year-end tax planning can make a meaningful difference in long-term wealth.
One of the most powerful tools in that toolkit? Tax-loss harvesting—used as part of a broader, values-based financial plan.
Why Year-End Tax Planning Matters
Year-end is the natural checkpoint for your tax picture: income is clearer, investment gains and losses are easier to tally, and there’s still time to make strategic moves before the calendar turns.
Thoughtful year-end tax planning can help you reduce current and future taxes, improve cash flow, and keep your investment strategy aligned with your goals. It’s especially important for high-earning professionals, retirees drawing from portfolios, and business owners in the Greater Philadelphia area. When combined with a holistic financial planning approach, these decisions support not just your balance sheet, but the life you’re building.
What Is Tax-Loss Harvesting?
Tax-loss harvesting is the process of selling investments that are currently at a loss to offset capital gains elsewhere in your portfolio. In simple terms, you’re using paper losses to reduce the taxes you owe on realized gains—while keeping your long-term investment strategy intact.
In many cases, the proceeds from the sale are reinvested into a similar (but not “substantially identical”) investment to maintain your overall asset allocation. This is where a disciplined, goals-based investment management strategy matters. The objective is not to chase losses, but to turn an unfortunate market move into a thoughtful tax planning strategy.
When Might Tax-Loss Harvesting Make Sense?
Tax-loss harvesting can be especially useful in years when markets have been uneven or when you’ve triggered significant capital gains from rebalancing, selling a business, or real estate transactions.
A few situations where a conversation about tax-loss harvesting may be helpful include:
- You realized large capital gains earlier in the year and want to reduce the tax impact.
- You have positions that no longer fit your long-term strategy and are currently at a loss.
- You’re looking to transition from concentrated holdings into a more diversified portfolio.
The key is to coordinate these moves with your overall tax planning strategies and investment goals, not to react emotionally to short-term market swings.
Avoiding Common Pitfalls (Including the Wash Sale Rule)
While tax-loss harvesting can be powerful, it’s important to follow the rules carefully. One of the biggest is the “wash sale” rule, which disallows the loss for tax purposes if you buy the same or a substantially identical security within a restricted window.
That’s why we typically design a replacement strategy that maintains your overall asset allocation—using a similar but not identical investment—so your plan stays on track. For clients in King of Prussia and surrounding Pennsylvania communities, we review not only brokerage accounts but also activity in IRAs and other accounts where the wash sale rule can still affect your tax picture.
Coordinating Tax Planning With Your Bigger Financial Picture
Tax-loss harvesting is just one part of year-end tax planning. For many of our clients, this time of year is also an opportunity to:
- Review retirement contributions and consider Roth conversion opportunities
- Evaluate charitable planning strategies that align with family values
- Revisit estate planning strategies and gifting approaches for children or grandchildren
- Check whether your current tax picture is consistent with your long-term retirement planning and legacy goals
Because Certior Financial Group operates as a fee-only fiduciary financial advisor, we look at your tax situation within the context of your full True Wealth—your values, your family, and the future you want to build.
Local Perspective: Why It Matters Here in Pennsylvania
If you live or work in the Greater Philadelphia area—King of Prussia, Norristown, Wayne, Conshohocken, or across Montgomery and Chester Counties—state taxes, local income levels, and property considerations all shape how year-end tax planning strategies work for you.
A strategy that makes sense for a retiree drawing income from investment accounts in King of Prussia might look very different from the optimal plan for a business owner in Norristown or a dual-income household in Wayne. That’s why we believe in personalized, collaborative planning rather than one-size-fits-all checklists.
Ready to Talk About Your Year-End Tax Plan?
If you’re wondering whether tax-loss harvesting, charitable strategies, or other year-end tax moves make sense for you, you don’t have to figure it out on your own.
Certior Financial Group helps individuals, families, and business owners in King of Prussia and throughout Pennsylvania bring together investment management, tax reduction strategies, and long-term goals into one clear plan.
Start a conversation with us today to review your year-end tax planning options and see how thoughtful, True Wealth–focused planning can support the life you want—this year and beyond.
