Coordinate Tax Planning with Your Financial and Tax Advisors

As we approach the end of the calendar year, you only have a few months remaining to take advantage of certain planning opportunities. 

In this four-part series, we’ll cover a range of planning topics that can help you save on taxes as you work toward achieving your financial objectives. If you’re a corporate executive, you’ll find that some of these topics are particularly relevant to you as year-end gets closer.

In our first blog post of the series, we identify three areas where you may be able to coordinate income tax planning between your financial advisor and tax advisor.

Tax strategies around incentive stock options

If you’re an executive and have started selling your company shares through a 10b5-1 plan, updated income projections are critical to ensuring you’re paying enough in estimated taxes and/or tax withholdings.

Further, if you have had restricted stock units (RSUs) vest or have exercised and sold non-qualified stock options (NQSOs) during the year, perhaps through a 10b5-1 plan, there could be opportunities to think strategically about your incentive stock options (ISOs). In this case, your ordinary income may exceed your alternative minimum tax (AMT) income, which could allow for an opportunity to exercise and hold your ISOs with favorable tax treatment (assuming special rules and holding requirements are satisfied). Make sure to coordinate with your financial and tax advisors on this specific issue.

Identify potential Roth conversion opportunities

Updated income projections may also help identify other opportunities, such as Roth conversion strategies. If your marginal tax bracket in 2023 is lower than your anticipated tax bracket in retirement, it may be a good year for a Roth conversion, which would convert pre-tax retirement funds to a Roth IRA. You’ll need to pay the taxes now on the conversion amount, but the funds will grow tax-free inside your Roth IRA and can be withdrawn tax-free, assuming you make qualified withdrawals.

Harvest your capital losses

If you own securities that have dropped in value relative to your cost to purchase them, then you have an unrealized capital loss. For our clients, we practice tax-loss harvesting as asset prices move throughout the year. We sell securities with losses (i.e., realize the capital losses) and buy something comparable to maintain similar market exposure, diversification, and portfolio balance. Capital losses not only help offset taxable gains this year, but unused losses may also be carried forward to offset future gains. In addition to offsetting gains, you can deduct $3,000 of net capital losses against ordinary income each year. Consult with your financial and tax advisors to ensure you avoid a “wash sale” (i.e., you sell a security at a loss and repurchase the same or very similar security shortly before or after this sale). Make sure you comply with this and other IRS rules that may otherwise disallow the capital loss.

Here to support you

The opportunities for year-end planning are many and varied, and each brings its own complexity depending on your particular circumstances. Be sure to engage your Corient Wealth Advisor, as well as any tax and/or legal advisors you may work with, to determine what strategies are best for you.


Other topics in this four-part series:

  • Part 2: Optimize Your Retirement Plan Contributions
  • Part 3: Plan Your Philanthropy
  • Part 4: Review Your Gifting and Estate Plans


Hope Carlson, CFP®, CAP®

Hope Carlson, CFP®, CAP®

Partner, Wealth Advisor

Hope is a Partner, Wealth Advisor in our San Diego office. She joined legacy firm Dowling & Yahnke in 2017. She is a CERTIFIED FINANCIAL PLANNER™ professional and holds the Chartered Advisor in Philanthropy (CAP®) designation.

Prior to Dowling & Yahnke, Hope spent six years as the chief development officer at the Museum of Us, overseeing fundraising and marketing. She also served as the interim executive director for the San Diego Civic Youth Ballet in Balboa Park and for four years as a strategy consultant with the Boston Consulting Group.

Hope holds a Master of Business Administration (MBA) from Harvard Business School, where she was a Baker Scholar, graduating in the top 5% of her class. She also obtained her Master of Music in Vocal Performance and Literature from the Eastman School of Music and a Bachelor of Arts in Economics with Highest Distinction from the University of Virginia.

Trained as an opera singer, Hope is passionate about music and the arts. She lives in La Jolla with her husband and two daughters.

Michael Brown

Michael Brown

Partner, Wealth Advisor

Mike is a Partner, Wealth Advisor in our San Diego office. He has more than 25 years of professional experience advising clients on strategic financial matters, including business exit planning, tax planning, generational wealth transfers and estate planning, investment management, charitable giving and retirement planning.

Mike joined legacy firm Dowling & Yahnke in 2012 and was a partner at Deloitte prior to that. He holds the Chartered Financial Analyst® and CERTIFIED FINANCIAL PLANNER™ certifications, is licensed as a Certified Public Accountant (CPA) and has a Master of Business Administration (MBA) degree from the Kellogg School of Management at Northwestern University. Mike completed his undergraduate work at Oakland University (Michigan), where he majored in accounting and graduated summa cum laude. He grew up in Michigan and enjoys outdoor activities such as golf and skiing. Mike has been married to his wife, Jennifer, for more than 25 years and has two daughters.


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