• Start with a full-year tax projection so you can see how income, investments, deductions, and potential planning decisions interact.
• Review retirement contributions, charitable giving, employer benefits, upcoming cash needs, and estate documents while there is still time to make changes.
• Involve your financial planner, CPA, and estate planning attorney early when one decision could affect several parts of your financial life.

Why Should You Start Year-End Financial Planning in October?

By December, your CPA may be buried, your estate attorney may be booked, your company’s benefit elections may be closed, your financial planner is already buried, and the charitable gift you thought would take two days may require two weeks.

October gives you something December rarely does: Options.

Year-end financial planning doesn’t mean trying to find clever ways to save taxes before the ball drops in Times Square. Instead, you need to look at what changed this year, what you expect next year, and which decisions still have a deadline attached to them.

Selling an investment may change your tax projection. A large charitable gift may influence which investment you sell or donate. A Roth conversion could affect your tax bracket, Medicare premiums, and available cash. An estate planning decision may require an appraisal, legal documents, and a conversation with the family.

Those pieces take time to coordinate.

I would much rather see the whole picture in October than receive seven unrelated questions during the final week of December. By then, the question often changes from “What makes the most sense?” to “What can we still get done?”

1. What Will Your Full-Year Tax Picture Look Like?

Before making a year-end tax decision, you need a reasonable estimate of your total income and tax exposure.

Start with salary, bonuses, business income, investment income, and any consulting work. Add realized capital gains, real estate transactions, stock option exercises, RSU vesting, and other income that may not show up in an ordinary paycheck. Then look at withholding, estimated payments, deductions, and charitable contributions.

If this year looked different from last year, your old tax assumptions may no longer be useful. Maybe you received a larger bonus, sold a property, exercised stock options, or had an unusually profitable business year. Perhaps your income dropped because you changed jobs, took a sabbatical, or retired.

Income changes require a different approach, whether the change moves your income up or down.

A tax return tells you what already happened. A tax projection gives you time to make decisions.

Once your planner and CPA have a shared set of numbers, you can evaluate whether it makes sense to realize gains, complete a Roth conversion, increase retirement contributions, make a larger charitable gift, or adjust an estimated payment. Recent tax law changes taking effect in 2026 make that projection even more important.

2. Does Your Investment Portfolio Still Fit the Job It Needs to Do?

A year-end investment review should go beyond asking whether the portfolio made money.

I would want to know whether market movements changed your intended allocation, whether one company or industry now represents too much of your wealth, and whether the portfolio still matches what you need the money to do.

This is especially important for executives holding employer stock and real estate investors with a large share of their net worth tied to one market. A holding can be a good investment and still occupy too much of your financial life.

Taxes belong in this conversation too. Look at the capital gains and losses you have already realized. There may be opportunities to sell investments at a loss and offset certain gains, but tax-loss harvesting should support the investment plan rather than drive it.

You also need to consider the IRS wash-sale rules before repurchasing the same or a substantially identical investment. Those rules can become particularly messy when trades occur across multiple brokerage accounts, retirement accounts, or a spouse’s account.

Finally, check what you will need from the portfolio over the next few years. Money intended for tuition next fall, a home purchase, or the first years of retirement has a different job from money that can remain invested for another decade.

3. Are You Using the Retirement Savings Opportunities Available to You?

Review your retirement contributions before the final few payroll cycles of the year.

For 2026, employees can generally contribute up to $24,500 to a 401(k), 403(b), or governmental 457 plan. The general catch-up contribution for people aged 50 and older is $8,000, while people ages 60 through 63 may qualify for a higher $11,250 catch-up contribution.

There is also a new wrinkle for some higher-income employees. Beginning in 2026, employees whose prior-year wages from the employer exceeded $150,000 generally must make catch-up contributions on a Roth basis if the plan allows catch-up contributions.

I would review the following areas.

• Year-to-date employee contributions
• Employer matching contributions
• Catch-up eligibility
• After-tax contributions and in-plan Roth conversions
• IRA or backdoor Roth planning
• SEP IRA, solo 401(k), or other business-owner plans
• Potential Roth conversions from existing retirement accounts

Maximizing every available account is not automatically the right answer. You still need enough cash for taxes, family expenses, and near-term goals. It may also make sense to build different sources of taxable, tax-deferred, and tax-free retirement income rather than sending every available dollar to the same type of account.

4. Could Your Charitable Giving Be More Intentional This Year?

Start with what you want your giving to accomplish. Which organizations matter to you? How much do you want to give? Would you still make the gift if there were no tax deduction?

Once those questions are answered, you can decide how to fund the gift.

Writing a check may be simple, but it may not be the most efficient choice if you own investments that have appreciated significantly. Donating eligible appreciated securities directly may allow you to support the charity without selling the investment first and realizing the gain.

Don’t forget about qualified charitable donations from your IRAs. If you’re over 70.5 years old, you can make a donation directly from your IRA without having to pay taxes on the withdrawal. These donations can be used to satisfy required minimum distributions, and the charity ultimately gets more money because they won’t have to pay taxes on that donation. Win-win.

Some families also group several years of donations into one tax year or contribute to a donor-advised fund. With a donor-advised fund, the sponsoring organization takes legal control of the contribution, while you retain advisory privileges over how grants are distributed to charities.

That can be useful during an unusually high-income year or when you know how much you want to give but have not chosen every organization yet.

These strategies require lead time. A charity may need to verify its brokerage instructions. A donor-advised fund must be established and funded. Privately held assets may require additional documentation or a qualified appraisal.

December 29 is a poor day to begin that process.

5. Do Your Employer Benefits and Equity Compensation Need Attention?

Some of the least flexible year-end decisions arrive through your employer.

Open enrollment is the obvious example. Review health coverage, HSA or flexible spending account elections, disability insurance, life insurance, and dependent care benefits. If you and your spouse both have workplace coverage, look at the options together before making separate elections.

I have seen couples pay for overlapping benefits while leaving a useful option untouched because each person assumed the other had handled it.

Executives may have additional decisions involving deferred compensation, employee stock purchase plans, RSUs, and stock options. Review what vested this year, what may vest next year, and whether any option exercise windows are approaching.

An option exercise can affect your taxes, cash flow, and exposure to employer stock at the same time. A deferred compensation election may influence income years into the future and may be difficult or impossible to change later.

6. Has Your Estate Plan Kept Up With Your Actual Life?

An estate plan can still be legally valid while doing a poor job of reflecting your current wishes.

Review your will, revocable trust, financial power of attorney, health care directive, and beneficiary designations. Confirm that the people named as executor, trustee, guardian, and agent are still the people you want in those roles.

Then look at what has changed.

Did you get married or divorced? Was a child or grandchild born? Did someone named in the documents die? Did you buy property, sell a business, open new accounts, move to another state, or begin providing significant financial support to a family member?

Larger lifetime gifts may require even more coordination. For 2026, the annual federal gift tax exclusion is $19,000 per recipient. Giving more doesn’t necessarily mean you will owe gift tax, but it may create a reporting requirement and use part of your lifetime exemption.

The number alone should not decide how much you give. I would first want to know how the gift affects your own security, what you want it to accomplish, and whether everyone understands what the money represents.

7. What Will Your Family Need Cash for Over the Next Year?

Before increasing retirement contributions, investing extra cash, or making a large gift, look at what the next twelve to eighteen months may require.

That could include tax payments, tuition, a home purchase, renovations, business funding, family support, travel, insurance premiums, or the first year of retirement.

I would rather know in October that you need $200,000 next June than discover it after we have invested the cash, exercised stock options, and funded a large charitable gift.

Add up the known expenses, leave room for the less predictable ones, and decide where the money should come from. That may mean holding more cash, directing an upcoming bonus toward the goal, or identifying investments that can be sold thoughtfully.

If selling investments would create an unwanted tax bill, there may be other ways to access cash, although borrowing against assets introduces its own costs and risks.

Liquidity is what makes the rest of the plan workable. A strategy can look impressive on paper and still be a bad fit if it leaves your family scrambling for cash six months later.

Give the Important Decisions Enough Time

You may review these seven areas and decide that only two require action this year. That is a perfectly good outcome.

You don’t need seven new financial strategies before December 31. You need a clear view of what changed, what’s coming next, and which decisions still have a deadline attached to them.

If your taxes, investments, benefits, charitable plans, and estate decisions have started to feel like separate conversations, Lanning Financial can help you bring them into one financial picture.

Start with our brief questionnaire to tell us a little about your situation and see whether working together may be a good fit.

Jessica Lanning, CFP®

Email: jessica@lanningfinancial.com
Phone: (415) 354-5699
LinkedIn: linkedin.com/in/jessicalanning
YouTube Channel: Lanning Financial on YouTube

Lanning Financial Inc. is a registered investment adviser. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.

Finding the right retirement income sources

What about the government?  Will Social Security income go away?  Hard to say.  Social Security income is a huge political football that no one wants to drop or be accused of ending.  As workers (a large electorate), we pay into the system and would like to see money out of the system.  Yet, the Social Security statement itself discloses that it predicts to pay on 78% of benefits in 2037 (http://www.ssa.gov/mystatement/currentstatement.pdf).  Even my clients in their late 50s don’t think they’ll get a dime of Social Security.  Here’s my take:  If it’s there, I want my clients to get their share and have that share be taxed as little as possible.  That takes some planning now.

What about employers?  Will employer pensions ever come back into vogue?  Unlikely.  They’re expensive and complicated to manage.  Employers faced with rising costs (medical insurance being high on that list) are looking to give retirement income benefits as cheaply as possible.  In years past that has meant the 401k, which for most highly compensated employees and business owners is inadequate.  The 401k was never intended to be the sole retirement benefit. It was designed to supplement the pension offered.  Even if my clients fund a 401k, we have to find alternate investment vehicles.

What about personal savings?  No one feels they’re saving enough.  That might be true.  Only to make it worse, no one feels like they made any money with their investments in the last 10 years.  There are many solutions here besides winning the lottery (and, by the way, if this is your solution, remember that you have to play to win – it’s always about the follow-through).  One of the tricks, I believe, is to find retirement income sources that provide tax-free income.  No, not the Roth IRA which most Bay Area families don’t quality to fund, and even if they did, they’d only be able to put away $5K.  Business owners (especially of C corporations), in particular, have potentially one of the best strategies to make this happen.  The other trick is to find non-stock market related investments.

The government might create a universal retirement funding plan.  You might win the lottery.  Or, you might just explore some of your personal savings options.