🗂️ Clean Up Your Financial Junk Drawer Before 2026

☕ Good morning SenseMakers!

Most year end financial checklists focus on rebalancing portfolios, harvesting losses, and hitting contribution limits. Those moves matter. But for busy executives and business leaders, the bigger leak is often simpler: complexity.

You have accounts from three employers. A handful of IRAs. Two HSAs you forgot about. A random brokerage account that never got closed. Beneficiary forms you filled out a decade ago. A folder of PDFs that only you understand.

It all works, until it does not. Until you need one specific document fast. Until your spouse tries to locate something. Until a rollover deadline passes because nobody was watching. Until you realize the beneficiary on your largest account is still your ex employer's plan, not your family.

If your financial life is scattered across old accounts, outdated beneficiaries, and missing documents, your real risk is not the market. It is preventable chaos.

As we head into the final week of 2025 and the holidays approach, this is the perfect moment to create a single source of truth and reduce the odds of an expensive mistake. Less mental load, fewer loose ends, and a cleaner foundation so tax, equity, investing, and retirement decisions in 2026 get easier instead of harder.

Today, we are walking through three practical moves to declutter your financial junk drawer before the calendar resets.

🧰 What Is a Financial Junk Drawer?

Think about the kitchen junk drawer. Batteries, random keys, take out menus, expired coupons, tape, a flashlight that may or may not work. Everything sort of works until you need one exact thing fast and cannot find it.

Your financial life can look the same. Old 401(k)s from prior employers. Tiny rollover IRAs. Multiple HSAs. Forgotten 529s. Brokerage accounts opened for one trade. Random bank accounts. Old life insurance policies. Outdated beneficiaries. Passwords stored on sticky notes or scattered across browsers.

Here is why it matters:

Time cost and mental load. Every extra account is a login to remember, a statement to review, and a decision point during tax season or rebalancing.

Higher odds of missing deadlines or making errors. Rollover deadlines, RMD requirements, beneficiary updates, contribution limits. More accounts means more chances for something to slip.

Estate and access friction. If something happens to you, can your spouse or family find everything in 30 minutes? Or will they spend weeks calling custodians, searching emails, and guessing passwords?

Simplicity is a risk management strategy. Not because simple is always better, but because complexity without structure is expensive.

📦 Core Move 1: Consolidate Low Value Accounts and Old 401(k)s

Start with inventory. Pull up a spreadsheet or a notes app and list every financial account you have:

• Account name and custodian

• Type (401(k), IRA, Roth IRA, HSA, taxable brokerage, 529, etc.)

• Approximate balance

• What it is for (if you know)

Once you have the list, ask yourself: which of these accounts are creating friction without adding value?

The classic culprit is the old 401(k). You left a job three years ago. The 401(k) is still sitting there with limited investment options, high fees, and a login you have to reset every time you check it.

You have four options:

1. Keep it where it is. Sometimes this makes sense if the plan has great investment options, low fees, or unique features you need.
   

2. Roll it to your new employer plan. This works if your new plan accepts rollovers and has better options or features.
   

3. Roll it to an IRA. This gives you maximum control and flexibility, but comes with considerations (more on this below).
   

4. Cash it out. Almost always the worst option due to taxes and penalties, but technically available.

The cleanest path for most people is a direct rollover. This means the money moves directly from the old plan to the new plan or IRA without ever touching your hands. The IRS is clear: retirement plan distributions paid directly to you can trigger mandatory withholding, and rolling directly to another plan or IRA avoids that withholding.

If you do an indirect rollover where the check comes to you, deadlines and taxes get messy. Avoid this unless you have a very specific reason.

Two important warnings for executives:

If you use or plan to use a backdoor Roth IRA strategy, rolling old 401(k) dollars into a traditional IRA can create pro rata complications. The IRS aggregates traditional IRA balances for key calculations, which can make the backdoor Roth less tax efficient. If this applies to you, consider rolling old 401(k) assets into your current employer plan instead of an IRA.

If you have employer stock inside the plan, there may be special net unrealized appreciation (NUA) rules that could save you significant taxes. Pause and talk to your advisor before moving it.

One other nudge: SECURE 2.0 allows plans to raise the mandatory cash out threshold from $5,000 to $7,000 for distributions after December 31, 2023. This means small orphan accounts can get moved or cashed out automatically if you ignore them. Do not let inaction make the decision for you.

🔑 Core Move 2: Beneficiaries, Logins, and the "If Something Happens" File

This is the highest leverage, most ignored area of financial planning.

Beneficiary forms are not a formality. For most retirement accounts, life insurance policies, and certain brokerage accounts, the plan or policy pays based on the beneficiary designation on file. Your will does not override it. Your trust does not override it. The form controls.

Run a beneficiary sweep across every account:

• 401(k)

• Traditional IRA

• Roth IRA

• HSA

• Life insurance policies

• Brokerage accounts with transfer on death (TOD) registration

• Any annuities

Make sure primary and contingent beneficiaries are present and aligned with your current intent. If you got divorced, remarried, had kids, or experienced any major life change, your beneficiary forms need to reflect that.

A quick story: we worked with an executive who updated his estate plan and trust after his second marriage. Everything was clean. Except he never updated the beneficiary on his $1.2 million 401(k). It still listed his ex wife. When he passed unexpectedly, the plan paid her, not his current family. The trust was irrelevant. The beneficiary form controlled.

Do not let this be you.

Beyond beneficiaries, access matters just as much. If your spouse or partner cannot log into accounts or locate key documents, your plan fails under stress.

Create an "if something happens" file. Keep it simple:

A one page account map: List every institution, account type, last four digits of account numbers, and current beneficiary status.

Where key documents live: Will, powers of attorney, health care directive, life insurance policies, property deeds, car titles.

Key contacts: CPA, estate attorney, financial advisor, HR benefits contact.

Password manager access instructions: Not a list of passwords written down, but clear instructions on how to access your password manager if needed.

The Consumer Financial Protection Bureau's disaster checklist emphasizes collecting, copying, and storing key financial information and account numbers. The National Institute on Aging has an "affairs in order" checklist that includes legal and financial records plus health care directives. Both are excellent free resources.

As you gather with family this holiday season, consider sharing this information with a trusted partner or family member. It is one of the most valuable gifts you can give, even if it feels uncomfortable to talk about.

🛡️ Core Move 3: Insurance and Estate Basics (Quick Gap Scan Only)

This is not "redo your entire estate plan before Christmas." This is "spot obvious gaps before 2026."

Here is your quick checklist:

Estate basics to confirm exist and are findable:

1. Will. Does one exist? Is it current? Does your spouse or executor know where it is?

2. Financial power of attorney. Who can make financial decisions for you if you cannot?

3. Health care proxy or advance directive. Who makes medical decisions if you are incapacitated?

Health care planning resources from the American Bar Association consistently highlight the importance of advance directives and naming decision makers. If you do not have these documents, or if they are more than five years old, add "update estate documents" to your January list.

Insurance basics to scan:

1. Life insurance. Is it in force? Is the owner and beneficiary correct? Is the coverage amount still appropriate for your household?
   

2. Disability coverage. Do you have individual or group disability insurance? If your income supports your family, this is not optional.
   

3. Umbrella liability policy. Do you have one? Is it sized appropriately for your assets and risk exposure? Most high earners should carry at least $1 million to $2 million in umbrella coverage.

If any of these are missing or unclear, schedule a review with your insurance professional in early 2026. But at minimum, know where your policies are and confirm they are current.

One note: laws vary by state, and policies vary by carrier. This is general guidance. Talk to your estate attorney and insurance professional for personalized advice based on your situation.

🎁 A Holiday Gift to Yourself: Clean Data for 2026

As we approach Christmas and the final days of 2025, most people are focused on gifts, travel, and time with family. Those things matter. But one of the best gifts you can give yourself and your family is a clean financial foundation heading into the new year.

Major individual tax provisions from the Tax Cuts and Jobs Act are scheduled to expire at the end of 2025, which may shift brackets, deductions, credits, and related planning assumptions in 2026, depending on what Congress does. Clean data and organized accounts make it easier to model real scenarios when rules change.

Beyond taxes, 2026 brings new contribution limits for retirement accounts. The IRS announced a $24,500 employee deferral limit for many employer plans, plus updated catch up limits. HSA limits increased to $4,400 for self only coverage and $8,750 for family coverage.

If your accounts are scattered, your beneficiaries are outdated, and your documents are missing, you will spend the first quarter of 2026 playing catch up instead of executing a clear plan.

The cleanup we have walked through today takes one focused hour. Maybe two if you have a lot of accounts. But it creates leverage for every financial decision you will make next year.

🧠 Making Sense of Your Financial Junk Drawer

The goal is not perfection. The goal is a clean decision system.

Your portfolio is not your plan. Real financial planning integrates cash flow, taxes, equity compensation, risk management, and legacy into one picture. This cleanup creates the foundation for all of that.

At Tailored Wealth, we act as the single source of truth for clients. We track accounts, coordinate beneficiaries, monitor deadlines, and integrate everything into a repeatable system that evolves with your life. Not because our clients cannot do it themselves, but because they would rather spend their time on higher value decisions, like building their business, advancing their career, or being present with their family.

If this resonates, take the Financial Stress Test as a fast way to identify whether complexity is creating hidden risk, and where the biggest gaps are across planning, risk, tax, and legacy.

As we head into the final week of the year, we want to wish you and your family a wonderful holiday season. Thank you for being part of the Making Sense of Your Money community. Whether you have been with us since the beginning or just joined recently, we are grateful for your trust and your time.

Here is to a cleaner, calmer, and more intentional 2026.

As always, I hope this helps you to Prioritize Your Version of a Rich Life.

Until next week!

This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.

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