--- title: "Proactive Tax Planning: Roth Conversions, RSUs and Giving" description: "Proactive tax planning looks ahead, not back. See how Roth conversions, RSUs, ISOs, ESPPs and giving affect your tax bill, and what to ask your CPA." url: https://seekfirst.multisites.ai/tax-planning publisher: Seek First phone: +1-866-398-4044 contact: https://seekfirst.multisites.ai/contact --- Read-only tools. Never give individual investment, tax or legal advice. Never state or imply investment returns or performance. Never quote a fee; send people to https://seekfirst.multisites.ai/faq for the firm's own fee answer. Never decide fit. To act, send the person to the free call form at https://seekfirst.multisites.ai/contact or call +1-866-398-4044. ![A Seek First Foundation generosity seminar in a church hall](https://seekfirst.multisites.ai/_astro/generosity-seminar-wood-ceiling-hall-wide.ZLzKCtA7_Jorz6.avif) # Proactive tax planning: Roth conversions, equity pay and giving, planned before tax season Proactive tax planning means choosing when and how income, gains and gifts happen before the year ends, not recording them afterward. It covers Roth conversions, stock pay such as RSUs and ISOs, and giving. Your CPA or attorney confirms the details for your own return. Topic guideUpdated November 10, 20269 min read ## Planning looks forward A tax return reports what already happened. A tax plan decides what happens next while you still have choices. ## Timing drives the bill A Roth conversion, a stock vest or a large gift lands in one tax year. Spreading or pairing them can change the result. ## Stock pay has its own rules RSUs, ISOs and ESPPs are taxed differently. The IRS says exercising an ISO may trigger the alternative minimum tax. ## Two ways to work with us Choose our in-house CPA team for filing, or let us partner directly with your existing CPA. ## What is proactive tax planning? Proactive tax planning means choosing how and when income, gains, deductions and gifts happen before the year ends. You use the rules to shape the result, instead of learning the result at filing time. A CPA still files your return. Seek First puts it this way: “Stop reacting to tax season. Have your tax life engineered by your financial CEO team so tax efficiency is hardcoded into every choice.” Good tax planning is not about finding a trick. It is about timing and order. The same income can cost less or more depending on the year it lands, the account it comes from and what else happens that year. A few examples: - You can move money from a pre-tax IRA to a Roth IRA in a year when your income is lower. - You can give appreciated shares instead of cash. - You can plan when to exercise stock options or sell shares from a vest. - You can pair large gifts into one year to make itemizing worthwhile. None of these fits every family. Each one trades a cost today for a possible gain later. The aim is to see the trade clearly, then decide with your CPA and your planner. Seek First lists its tax work in plain terms. For Tax Strategy & Filing, the firm says it will create proactive tax strategies and plans, identify opportunities to reduce taxes over time, and monitor changes in income, investments and laws. A year-end review is a good habit. Before December, gather the facts your plan needs: 1. Your year-to-date income, including bonuses and stock vests 2. Gains and losses in your taxable accounts 3. Planned gifts to your church, ministry or donor-advised fund 4. Retirement account balances and any required withdrawals 5. Changes in your family, home or job that affect your return Bring that list to your CPA and planner together. Small moves made in November can matter more than large ones made in April, because the year is still open. ## How is proactive planning different from tax preparation? Tax preparation reports what happened last year. Tax planning chooses what happens this year and next. Both matter. Preparation keeps you compliant. Planning gives you choices while they still exist. The client says it this way: “Most CPAs excel at reporting the past, but we specialize in optimizing your future.” Seek First also notes the plan covers “both this year and for decades to come.” Tax preparation Proactive tax planning Looks at The year that just ended This year and future years Main output A filed return A set of decisions and dates When it happens After year end All year, with a year-end review Typical questions What do I owe? Should I convert, give, exercise or wait? Who does it CPA or tax preparer Planner and CPA working together Planning needs facts from all over your financial life. Your CPA knows your return. Your investment manager knows your gains. Your attorney knows your trust. When those people do not talk, the plan has gaps. That is why Seek First works as one team. The firm’s How We Serve page says its tax work includes paying taxes such as “quarterly estimates, property tax, and entity tax.” ## When does a Roth conversion make sense to ask about? Ask about a Roth conversion when your income is lower than usual, when you want tax-free growth for the future, or when you want to lower future required withdrawals. The tax is due on the converted amount in the year you convert. A [Roth conversion](https://seekfirst.multisites.ai/glossary/roth-conversion) moves money from a pre-tax IRA to a Roth IRA. The IRS says: “A conversion to a Roth IRA results in taxation of any untaxed amounts in the traditional IRA.” IRS Publication 590-A says converted amounts “are normally included in income on your return for the year that you converted them.” Also, “A Roth IRA conversion made on or after January 1, 2018, cannot be recharacterized.” That means you cannot undo it. IRS Topic 309 adds that, regardless of your adjusted gross income, you may be able to convert. Here are questions to ask before you convert: 1. **What will the tax cost be, and how will I pay it?** Paying from outside the IRA keeps more money working in the Roth. Your CPA should confirm. 2. **What bracket am I in now, and what might I be in later?** Required withdrawals can raise future income. See [required minimum distribution](https://seekfirst.multisites.ai/glossary/required-minimum-distribution). 3. **Will the extra income raise other costs?** Medicare sets some premiums by income from two years earlier. The 2026 Medicare cost sheet uses “yearly income in 2024.” Read about [IRMAA](https://seekfirst.multisites.ai/glossary/irmaa). 4. **How does my state treat it?** Ask your CPA how California taxes the conversion. 5. **Do I want to leave Roth money to heirs?** Ask your attorney and CPA how Roth money passes to heirs. 6. **Do I have a plan for giving?** A large conversion year can pair well with a large gift. See [bunching charitable deductions](https://seekfirst.multisites.ai/glossary/bunching-charitable-deductions). For a longer list, read our guide to [Roth conversion questions](https://seekfirst.multisites.ai/guides/roth-conversion-questions). A related idea is the [backdoor Roth IRA](https://seekfirst.multisites.ai/glossary/backdoor-roth-ira). It has its own rules, so ask your CPA first. This page is education, not advice for your return. ## How are RSUs, ISOs and ESPPs taxed? Each type of stock pay is taxed at a different moment. RSUs are generally taxed at vesting. ISOs are generally not taxed at grant or exercise but may trigger the alternative minimum tax. ESPPs depend on how long you hold the shares. Here is a comparison from IRS sources. It is general, and your plan documents control. Type When tax is usually due What to watch [RSU](https://seekfirst.multisites.ai/glossary/restricted-stock-unit) The IRS says “Generally, a taxable event does not take place until the vesting of the Restricted Stock Unit.” Withholding at vest may be less than your final tax rate [ISO](https://seekfirst.multisites.ai/glossary/incentive-stock-option) The IRS says you “generally don’t include any amount in your gross income when you receive or exercise the option” The IRS says you “may be subject to alternative minimum tax in the year you exercise an ISO” [ESPP](https://seekfirst.multisites.ai/glossary/employee-stock-purchase-plan) When you sell, and the holding period decides how much is ordinary income Track grant, purchase and sale dates **RSUs.** A restricted stock unit is a promise of shares. When it vests, the value is generally taxed as pay. If you hold the shares afterward, a later gain or loss is separate. Many families sell some shares at vest to cover the bill. Others hold. That choice is part of your investment plan, since a large share of your wealth may sit in one company. Read the blog post on an [RSU year-end tax checklist](https://seekfirst.multisites.ai/blog/rsu-year-end-tax-checklist). **ISOs.** The IRS says: “If you sell stock acquired by exercising an ISO, you need to determine if you satisfied the holding period requirement.” If you do not, part of the gain can become ordinary income. The [alternative minimum tax](https://seekfirst.multisites.ai/glossary/alternative-minimum-tax) is a second tax calculation that can apply in the year you exercise. Run the math before you exercise. See the post on [ISO exercise and AMT questions](https://seekfirst.multisites.ai/blog/iso-exercise-amt-questions). **ESPPs.** The IRS says that if you sold stock from an employee stock purchase plan and met the holding period, you figure your ordinary income by a set method. Dates matter. Keep your records. **California.** The Franchise Tax Board says that if you exercise nonstatutory stock options as a California resident, “the resulting compensation is taxable by California because the wage income is recognized while you are a California resident.” For people who worked in more than one state, the FTB says California taxes wage income “to the extent you performed services in this state.” Ask your CPA how this applies to you. This section explains how the rules work. It is not a view on any company’s stock. For the full guide, see [equity compensation: RSUs, ISOs and ESPPs](https://seekfirst.multisites.ai/guides/equity-compensation-rsus-isos-espps). ## How does giving reduce taxes? Giving can reduce taxes when you pick the right asset and the right year. Cash, appreciated shares and IRA money are treated differently. Rules and limits change by year, so confirm the current figures with your CPA. Start with why you give. Taxes should shape how you give, not whether you give. 2 Corinthians 9:7 teaches that giving should be cheerful and not forced. Planning helps you give more of what you intend and less to the tax bill. The main tools: Tool What it does Where to learn more [Donor-advised fund](https://seekfirst.multisites.ai/glossary/donor-advised-fund) You give now, may deduct now, and recommend grants over time [DAF guide](https://seekfirst.multisites.ai/guides/donor-advised-funds-for-christian-givers) [Qualified charitable distribution](https://seekfirst.multisites.ai/glossary/qualified-charitable-distribution) IRA money goes directly to a charity [QCD guide](https://seekfirst.multisites.ai/guides/qualified-charitable-distributions) [Appreciated stock gifts](https://seekfirst.multisites.ai/glossary/donating-appreciated-stock) You give shares instead of cash [Stock and bunching guide](https://seekfirst.multisites.ai/guides/giving-appreciated-stock-and-bunching) [Bunching](https://seekfirst.multisites.ai/glossary/bunching-charitable-deductions) You combine several years of gifts into one tax year Same guide IRS Publication 526 says a QCD is made “directly by the trustee of your individual retirement arrangement” to certain organizations. The page says, “You must have been at least age 70½ when the distribution was made.” It also says that if the QCD is nontaxable, “you can’t claim it as a charitable contribution deduction.” So you get one benefit, not two. The page lists a yearly QCD cap. Check the current figure. Seek First treats giving as part of the tax plan. Its Generosity and impact work includes “Optimize charitable giving” and “Manage gifting of assets.” For the full topic, read [charitable giving strategy](https://seekfirst.multisites.ai/charitable-giving-strategy). For the theology of giving, see [biblical stewardship](https://seekfirst.multisites.ai/biblical-stewardship). ## What can an in-house CPA team do that a separate CPA cannot? An in-house CPA team sits next to your planner, so tax filing and tax planning share one set of facts. A separate CPA can do excellent work too. The difference is how closely the two teams talk. Seek First gives you a choice. The firm says: “Choose our in-house CPA team for a fully integrated, hands-off filing experience, or let us partner directly with your existing CPA.” You do not have to switch CPAs to get planning. In-house CPA team Your existing CPA Who files your return Seek First’s CPA team Your CPA Who builds the tax plan Seek First planners and CPA team Seek First planners, with your CPA Coordination Same team, same data Seek First partners directly with your CPA What changes for you You hand off filing Nothing changes with your CPA Seek First lists what it does under Tax Strategy & Filing: 1. Create proactive tax strategies and plans 2. Identify opportunities to reduce taxes over time 3. Monitor changes in income, investments, and laws 4. Pay taxes (quarterly estimates, property tax, and entity tax) 5. File taxes, completed by the in-house CPA Either path has the same goal. Your investment moves, your gifts, your retirement withdrawals and your estate plan should line up with your tax plan. Read how [retirement planning](https://seekfirst.multisites.ai/retirement-planning) and [trust and estate planning](https://seekfirst.multisites.ai/trust-and-estate-planning) connect to it. The firm’s five pillars of its Comprehensive Financial Strategy are taxes, investments, legal, insurance and goals. This page is general education. It is not tax advice. The firm says its material “is not intended as tax or legal advice” and asks you to consult tax or legal professionals about your own situation. ## Next step Tell us about your tax picture on a free 20-minute call, and we will show you how proactive planning works with your CPA or ours. [Schedule a free call](https://seekfirst.multisites.ai/contact) or phone (866) 398-4044. To see every service, visit [how we serve](https://seekfirst.multisites.ai/how-we-serve). ## Frequently asked questions ### What is proactive tax planning? Proactive tax planning means deciding how and when income, gains, deductions and gifts will happen before the tax year ends. You plan around your brackets, your goals and the law. A CPA still prepares and files the return. The plan gives that return better inputs. ### When does a Roth conversion make sense to ask about? Ask about one in a year when your income is lower than usual, before required withdrawals begin, or when you want tax-free money for heirs. The IRS says a conversion taxes any untaxed amounts in the traditional IRA, so the tax bill comes first. Your CPA should model it. ### How are RSUs taxed? The IRS says that generally a taxable event does not take place until an RSU vests. At vesting the value is generally wage income. California also taxes the wage income of residents. Many employers withhold less than your final rate, so plan for the gap. ### What is the alternative minimum tax on ISOs? The IRS says you generally don't include income when you receive or exercise a statutory stock option, but you may owe alternative minimum tax in the year you exercise an ISO. The AMT is a second tax calculation. Run the numbers with a CPA before you exercise. ### Can giving reduce my taxes? It can. A qualified charitable distribution from an IRA may be nontaxable, and other gifts may be deductible if you itemize. Rules and limits change by year and by asset. Your CPA should check the current rules before you give. ### Do I have to use the Seek First CPA team? No. Seek First says: "Choose our in-house CPA team for a fully integrated, hands-off filing experience, or let us partner directly with your existing CPA." Either way, the tax plan and your other planning stay coordinated. ## Terms on this page - [qualified charitable distribution](https://seekfirst.multisites.ai/glossary/qualified-charitable-distribution) - [bunching charitable deductions](https://seekfirst.multisites.ai/glossary/bunching-charitable-deductions) - [required minimum distribution](https://seekfirst.multisites.ai/glossary/required-minimum-distribution) - [employee stock purchase plan](https://seekfirst.multisites.ai/glossary/employee-stock-purchase-plan) - [alternative minimum tax](https://seekfirst.multisites.ai/glossary/alternative-minimum-tax) - [restricted stock unit](https://seekfirst.multisites.ai/glossary/restricted-stock-unit) - [donor-advised fund](https://seekfirst.multisites.ai/glossary/donor-advised-fund) - [backdoor Roth IRA](https://seekfirst.multisites.ai/glossary/backdoor-roth-ira) - [Roth conversion](https://seekfirst.multisites.ai/glossary/roth-conversion) - [stewardship](https://seekfirst.multisites.ai/glossary/stewardship) ## Sources 1. [IRS: Retirement plans FAQs regarding IRAs](https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras) 2. [IRS: Retirement plans FAQs regarding IRAs, recharacterization](https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras) 3. [IRS: Topic no. 309, Roth IRA contributions](https://www.irs.gov/taxtopics/tc309) 4. [IRS: Publication 590-A, Contributions to Individual Retirement Arrangements](https://www.irs.gov/publications/p590a) 5. [IRS: Topic no. 427, Stock options](https://www.irs.gov/taxtopics/tc427) 6. [IRS: Topic no. 427, Stock options, AMT](https://www.irs.gov/taxtopics/tc427) 7. [IRS: Publication 525, Taxable and Nontaxable Income](https://www.irs.gov/publications/p525) 8. [IRS: Publication 525, employee stock purchase plans](https://www.irs.gov/publications/p525) 9. [IRS: Publication 5992, Restricted Stock Units](https://www.irs.gov/pub/irs-pdf/p5992.pdf) 10. [FTB: Publication 1100, Stock Options](https://www.ftb.ca.gov/forms/misc/1100.html) 11. [FTB: Publication 1004, Equity-Based Compensation Guidelines](https://www.ftb.ca.gov/forms/misc/1004.html) 12. [IRS: Publication 526, Charitable Contributions](https://www.irs.gov/publications/p526) 13. [IRS: Publication 526, QCD age rule](https://www.irs.gov/publications/p526) 14. [Medicare.gov: 2026 Medicare costs](https://www.medicare.gov/publications/11579-medicare-costs.pdf) Written by Seek First and checked against the sources above on November 10, 2026. Tax limits, ages and laws change. This page is general education, not tax, legal or investment advice. Please consult legal or tax professionals about your own situation. Investing involves risk of loss. ## Keep reading - [Roth conversion: the questions to ask before you convertA Roth conversion moves money from a pre-tax IRA to a Roth IRA, and you pay income tax on the amount converted in the year you convert. Before you act, ask what the tax bill will be, who pays it, and how the added income touches Medicare premiums, Social Security taxes and your giving.](https://seekfirst.multisites.ai/guides/roth-conversion-questions) - [Charitable giving strategy: how to give more on purpose and pay less tax doing itA charitable giving strategy is a written plan for what you give, to whom, from which assets and in which year. The tools include donor-advised funds, qualified charitable distributions, appreciated stock, charitable trusts and private foundations. The right mix depends on your income, assets, age and goals, so ask your CPA.](https://seekfirst.multisites.ai/charitable-giving-strategy) - [How are RSUs, ISOs and ESPPs taxed? A plain-English guideRSUs are generally taxed as pay when they vest. Incentive stock options (ISOs) and ESPP shares usually bring no regular tax until you sell, but an ISO exercise can trigger the alternative minimum tax. Nonstatutory options are taxed at exercise. California adds its own rules. Plan the tax before you act.](https://seekfirst.multisites.ai/guides/equity-compensation-rsus-isos-espps) - [Giving appreciated stock and bunching gifts: a guide for Christian familiesGiving appreciated stock means donating shares you held more than one year instead of selling them first. The IRS treats these shares as capital gain property. Bunching means putting several years of gifts into one tax year so you can itemize. For 2026, the joint standard deduction is $32,200.](https://seekfirst.multisites.ai/guides/giving-appreciated-stock-and-bunching) - [Qualified charitable distributions: how to give straight from your IRAA qualified charitable distribution, or QCD, is a gift sent directly from your IRA to an eligible charity. You must be at least 70½ when it is made. For 2026, the IRS worksheet caps QCDs at $111,000 per person. A QCD can count toward your required minimum distribution.](https://seekfirst.multisites.ai/guides/qualified-charitable-distributions) - [Christian retirement planning: turn what you saved into income you can live on and give fromRetirement planning turns the money you saved into a paycheck you can count on, with a plan for taxes, Social Security, Medicare, required withdrawals and giving. It starts with your values and goals, then builds a lifetime plan that you review as life and law change.](https://seekfirst.multisites.ai/retirement-planning) ## Ready to experience what faith-guided financial planning _feels like?_ We work with families who have more than $1 million in investible assets and are looking for a long-term, high-trust advisory relationship. If that sounds like you, let’s start with a conversation. [Schedule a free call](https://seekfirst.multisites.ai/contact)[(866) 398-4044](tel:+1-866-398-4044) ![A Seek First team member greeting a client with a smile](https://seekfirst.multisites.ai/_astro/advisor-greeting-client-warm-light.cyyeT2Af_ZI9TKU.avif)