2026 Financial Planning Checklist

January 1, 2026 – Is this the year to improve your financial plan? Sooner is better than later when it comes to a plan that achieves what you want. Whether you are a professional, business owner, or both, you don’t have to fix everything at once. Instead, look at our planning checklist and pick one thing to work on this year to improve your financial life. One clear win is better than many unfinished projects.

Tax Planning

Changes in tax laws have made tax planning more complex than ever. While tax rates may be lower now than they have been, it is worth asking if there are tax moves available now that will allow families to pay less tax over a lifetime, or perhaps the lives of heirs.

The recent “One Big Beautiful Bill Act” tweaked prior tax laws in ways that may make tax planning more complex (see our 2025 article What Does the 2025 One Big Beautiful Bill Act Mean for Your Taxes?). With tax brackets still at historic lows while government spending remains high, it may also be wise to plan on higher taxes in future generations.

For families with charitable intent, pairing giving methods with tax planning is more important than ever. For business owners, this also means thinking about how salary, bonuses, and distributions flow through to your personal return, and how your retirement plan at work fits into your own long-term plan.

Here are some tax planning questions to ask:

• While the estate and gift exemptions are higher than ever, will this last? While we are in a generous estate tax environment, should I consider what to do in case that changes?

• Am I managing and taking advantage of my marginal tax bracket now and in the future? Are there ways for me to reduce my income tax rate or perhaps intentionally increase it to “buy taxes on sale,” avoiding paying higher marginal rates later?

• Am I tax-planning or tax-reacting? Is my tax return process only reacting to what has happened, or am I proactive in my tax plan?

• If I am a business owner, am I coordinating my business structure, compensation mix (salary vs. distributions), and retirement plan design with my personal tax plan?

Charitable Giving Tax Deduction

Many people have charitable intent and are good at using tax deductions to leverage the value of their donations. But since the 2017 Tax Cuts and Jobs Act, some families are leaving tax deductions on the table.

For families with closely held business interests or concentrated stock positions, charitable giving can also be a powerful way to diversify over time and reduce risk if it is done thoughtfully.

Ask yourself:

• Am I giving as tax efficiently as possible (for example, using appreciated securities or qualified charitable distributions from retirement accounts)?

• Am I leveraging my variable marginal tax bracket to my advantage by separating the donation from the deduction through a donor advised fund?

• Am I bunching my deductions to maximize the increased standard deduction?

• Am I giving during my lifetime to get an income deduction, instead of primarily through my will?

• If I am planning a business sale, am I considering charitable strategies before the sale so I am not missing opportunities once the transaction is done?

To read more about how the government can subsidize your charitable giving, read our article about Charitable Giving Strategies for 2025 and Beyond.

Investments

We find that most families don’t have a written investment plan. Sometimes this results in a disjointed process that may not get the best outcome. Whether you are just starting or you have a very complex investment process, we believe an “investment policy statement” will improve the probability of a better outcome.

Be sure you have a written investment plan so your decisions are based on the plan, not on how you feel at any given time. This is especially important for business owners and leaders, who are used to making fast decisions under pressure and may overreact in their portfolios.

Here are some questions to ask about your investment plan:

• What can I do to remove emotional reactions from my investment process?

• Are my investments consistent with my objectives?

• Do I know what my returns have been?

• Do I have a defined plan for the next time there is an economic crash?

• Do I know how much risk I am taking, and is it the right amount of risk?

• Am I in agreement with my spouse about what we are invested in?

• Do I have a process for vetting investment opportunities as they arise?

• Are my investments tax efficient?

• Do I know my investment costs and are they low enough?

• Are my investments all managed in context so that they are not working against each other?

• If I own a business, am I treating that business as part of my overall investment risk, or ignoring it when I make portfolio decisions?

Retirement Planning (Including Your Business as an Asset)

Retirement planning is about much more than a number on a statement. For many leaders and business owners, “retirement” does not mean a sudden stop; it means more control, more flexibility, and sometimes a gradual transition out of the business. Your business itself may be one of your largest retirement assets, and how you plan for it will shape your options.

Ask yourself:

• Am I defining retirement correctly for me, or should I be focusing on getting my net worth up enough to make work optional?

• Am I using retirement accounts as they were designed, or solely to reduce tax?

• Am I managing cash in retirement in a way consistent with tax issues, to keep my lifestyle steady and at the same time correctly have a draw down strategy?

• If I am a business owner, do I have a basic path for turning my business into income someday (sale, succession, or wind-down), and is that realistic?

Cash Flow and Budgeting

We find that very few people budget. A new year comes with good intentions about losing weight, calories, exercise, and often reining in spending. But like counting calories, we don’t find most people will budget effectively, and if they do, one person in a relationship loves the idea, and the other not so much.

In relationships, it is this area that I believe causes more friction than any other. For business owners, there can be an added layer of stress when personal spending depends on variable income, bonuses, or distributions. Is there a better way to do this? We think so. See the hints below and some questions to ask yourself about how to improve:

• Is there a way to control my spending without a budget? (Hint – see our article on a cash flow process that is simple and elegant. THIS ARTICLE IS NOT COMPLETED YET)

• Am I sure my spending levels are not eroding my long-term plan?

• Is there friction with my spouse about spending priorities?

• Is there a simpler way to manage our cash flow process?

• If my income is irregular or tied to a business, do I have a system that smooths out my personal cash flow so that each year does not feel like “start from zero” again?

Estate Planning

It is easy to put this off. Comedian Steven Wright is quoted as saying, “I plan to live forever. So far, so good.” Estate planning documents are foundational to a financial plan and need regular review. There are many stories of loose ends left undone, leaving difficulty and conflict for the next generation. Is 2026 the year to improve your estate plan? Ask these questions to get started:

• Do I have a will? The answer is yes. The state you live in has already written you one. You have the option to write your own rather than follow what the state has decided for you. A properly executed will is a foundational document to an estate plan. If it is not properly executed, you don’t have one.

• Do I know what my will says, and do I know what it will not control at my death? Many people believe executing the will is the end of the estate planning process, however, for many, it is the beginning of the process. Over time, the will may have less and less control over what happens to your interests when you die.

• Are my documents up to date? A document review is a good idea any time there is a family transition (birth, death, marriage, divorce, business sale, new job, change of location, change in career, windfall, inheritance).

• Are my beneficiary designations up to date? In most cases, the will does not control retirement accounts or distributions from insurance products.

• Does my trust language accomplish what I want? Have I balanced no influence over my heirs with control from the grave? Which is best for my heirs?

• Is my trustee the right person for the job? Do I have a trustee with a conflict of interest? Is my trustee older than me?

• Have there been family changes since my estate plan was last designed?

• If I own a business, do I have at least a basic plan for what happens to that business at my death or disability (buy-sell agreements, continuity plan, or succession)?

Asset Protection and Insurance

Asset protection is the process of making sure my money cannot be taken from me due to an unforeseen event. Insurance is an important tool that is sometimes mismatched with asset-protection needs. For business owners, this often includes thinking about liability exposure, key people, and how the business itself could be affected by a loss.

Ask yourself:

• Are there ways someone can take my wealth away from me or my heirs?

• Do I have the right structure and the right insurance policies in place (home, umbrella, life, disability, long-term care, and appropriate business coverage)?

• Do I have insurance products that were purchased out of context of my current situation?

• Am I confident I have what I need as opposed to what I have been sold?

• If I am a business owner, have I addressed key person risk, basic continuity coverage, and my own ability to earn (through disability and life insurance)?

Do I Need Professional Help?

Many people, with adequate time, interest, and knowledge, can go it alone without professional help, and many people benefit from consulting a professional. However, healthy people can benefit from an annual physical - a consultation with a physician who will check in on health and look for future problems.

Some families benefit from outsourcing their financial plan. Some business owners benefit from having a planner who can coordinate with their Certified Public Accountant and attorney the same way a leadership group or peer advisory board helps them see blind spots in their business. There are many good stages in between.

Here are some questions to ask about whether you could benefit from talking to a professional:

• Do I have the time, interest, and knowledge to do this well on my own, year after year?

• Is my financial life getting more complex (business interests, multiple properties, larger balances) faster than my systems are improving?

• Would it reduce my stress to have someone else help monitor this the way a physician monitors health?

Read our two articles on Do I Need a Financial Planner and our second opinion service. If you would like to have a discussion about what you are doing, and whether we can help, please reach out and we will give you a no-nonsense opinion.

When considering this year’s objectives, make it a priority to gain control of your plan and notice how it positively impacts other decisions you make this year. Overwhelmed? Choose one thing to work on at a time. You do not have to solve everything in 2026 for it to be a very successful year.

Here’s to a financially successful 2026!

• Disclosures

  Information presented is for educational purposes only and is not personalized investment, financial, legal, tax, or accounting advice. Nothing on this website should be interpreted to state or imply that past performance is an indication of future performance. All investments involve risk and unless otherwise stated are not guaranteed. Be sure to consult with tax, legal, accounting, and financial professionals about your specific situation before implementing any planning strategies. Investment Advisory Services offered through Timberchase Financial, LLC, a Registered Investment Adviser with the U.S. Securities & Exchange Commission. Registration does not imply a certain level of skill or training.