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Life is interesting. It is filled with all sorts of drama. Tragedy, comedy, irony, mystery… Life has it all. And through it all, we have our unique ambitions and dreams. Some are fulfilled; others aren’t. As we see things unfolding, we change our priorities based on what we discover really matters most to us on this journey.

After being in the financial advisory business for 30+ years, I’ve come to learn that while people’s life circumstances may change quite a bit over time, their values rarely do.

This sentiment reminds me of the reason I wrote the very first edition of Worth Considering back in 2011. I’ll include its introduction here:

I am currently on a plane heading back to Orlando after attending a long-time client’s memorial service in Washington, DC. It may sound odd, but I couldn’t think of a better time to write this first installment of what will become a regular dialogue for years to come.

For the sake of privacy, I won’t mention the client’s name but can tell you that he was a fascinating genius who led a truly remarkable life. His obituary in the Washington Post highlighted some of his accomplishments but it was the comments made by his friends and colleagues at the service that really told his story. So while The Post could factually state that he was a remarkably bright man who earned a degree in Psychology from Yale before heading to Harvard for both Law School and his MBA, it took those he shared his life with to reveal his depth and character. They could tell of his sense of humor and of his sense of purpose. And he himself, through a letter he’d written as he knew he was failing, could tell about his intense drive to give away his wealth with as much intention and wisdom as he’d invested in developing it.

I am only telling you about this because this man was rich far beyond his material wealth. He was accomplished in many areas of life. His was the type of life that prompted others to carry around a bucket list long before the movie came out. And I’m not kidding; there were stories told about how people literally carried a list in their pockets inspired by the active life of this man who himself carried what was perhaps the first ‘bucket list’ I’d heard of. He saw just about all of the Earth’s beauty spots and conquered mountains like Kilimanjaro and the Matterhorn along the way. When you hear about someone who balanced their life with all their passions, you get inspired.

So I come back to the question of why I would tell you about this man and a brief piece of his life story. It is because he couldn’t possibly do the things he did if he didn’t have a passionate view of life and a purposeful view of assets and personal wealth. It was a true honor for me to help him with his quests for investing responsibly for many of his goals that we achieved throughout a 14 year client/advisor relationship. Had his time on Earth not been cut short by cancer at the age of 66, I’m sure we’d have extended that list of accomplishments. I’m sad to be missing out on that opportunity.

It’s with this in mind that I wanted to write this note today. My viewpoint of a successful partnership with each client goes beyond solely the responsible stewardship of their assets. It is my hope that each and every one of them lives a life of joy, purpose, and adventure, no matter how they define them. If my services can be a part of what helps someone live a life with more freedom and less stress, I am fulfilled.

I wish I could transcend the human realm and actually know the future of the markets and assure that every year ends with a higher net worth than the one before it but I know that just isn’t the case. However, in the absence of clairvoyance, we have only common sense and sound discipline to guide our path as investors. My team and I work hard on a daily basis to shine a little more light on that sometime treacherous path. We strive to continue learning about more efficient ways to manage risk and grow capital in the hopes that our clients take ample comfort in that knowledge to maintain our partnership and allow them to lead the lives they truly desire.

It’s in this spirit that I wanted this edition of Worth Considering to center not on the financial markets or the broader economy, but instead on the non-cyclical, permanent reasons of why we invest in the first place.

We’ve all heard it said that the more things change, the more they stay the same. And while that may be true, so is Jim Rohn’s observation that ‘it’s funny how day by day nothing seems to change, but when you look back, everything is different.’

This edition isn’t intended to answer any questions; it is intended to ask you to consider a few.

Our business has the purpose of asking questions that can help confirm what matters to you the most so we can design solutions to achieve those things. It’s just that simple. But it’s only possible if the questions are kept in front of us to be sure we’re still on that proper path after all of life’s twists and turns.

Markets may be unpredictable, but your personal financial plan should always reflect your true values.

So, before we all get swept away in the whirlwind of the Holidays, I wanted to get this piece out so you can give it some thought at your convenience and let us know if anything comes to mind that might need some valuable attention.

Through years of sitting down and working with families on reaching their planning goals, we’ve learned that a successful financial blueprint can be built on four core pillars:

Income Planning

Tax Planning

Risk Management

Legacy Planning

We have found that with proactive planning, each of these pillars are firmly within our control and together they are the most impactful drivers to achieve our goals.

We’ve also found that it is sometimes difficult for folks to see themselves and their own circumstance within these concepts. They are, admittedly, somewhat boring topics and are easy to gloss over, but they’re important. So, as we touch a bit on each of these areas, try to give each their proper importance to you and your life specifically. Don’t get bogged down in the minutia, instead be curious about how each might really play a role in your financial life.

To help set the proper mindset, ask yourself:

Am I in the same place in life as when I last considered the financial goals that matter most to me and my family?

Do I still have the same primary vision for my life? And is my money working towards making that vision a reality?

Are my assets in the proper position to best meet my expectations for my living years as well as the legacy I want to leave behind?

On one hand, these questions are about visions of future dreams. On the other hand, they are about the responsibilities of current logistics.

Like, do I have a large enough cash cushion in the bank? Does my portfolio have the proper asset allocation for my current risk tolerance? Is my portfolio as tax efficient as it could be? Do I have assets properly held in Trusts or with correct Beneficiary/Transfer On Death designations to be sure the right people (and not Uncle Sam) benefit from what I leave behind?

Consider even simpler things, too:

Do I still have the same relatives or desired beneficiaries, or has my family situation changed?

Am I working because I want to, or because I need to?

How is my health – emotional, mental, and physical?

Have I achieved any major milestone or suffered any sort of setback since I last looked at my big picture?

What concern, if any, keeps me up at night?

Have I recently experienced, or am I about to experience, a major financial event like selling a business, selling a home, or receiving an inheritance?

Am I making the impact I’d like to with gifting, charitable or otherwise?

That’s a lot of questions, I know. But they are intended to confirm we have clear focus on our financial picture as it currently stands, as well as the pictures we want to see next.

Below is a deep dive questionnaire to get into the details within each pillar. Please review it at your convenience and reach out to us if it prompts any thoughts or action items you’d like to discuss with us.

The takeaway:

We are quick to pay attention to market fluctuations and economic headlines, but we are slower to think about longer-term strategies and planning concepts that matter much more.
I have seen the statement that most people spend more time planning their vacation than their retirement. I would take that to mean they probably spend even less time thinking about what happens to their money after they’ve gone.
We don’t want that to happen on our watch! So please give some thought beyond the monthly statement to be sure we’re doing everything we can to maximize the value of your assets in every way – for you and those you care about!
Please emulate my friend who passed away and do your best to enjoy the truly valuable aspects of life – things that rarely have to do with money. I’m not (at all) a country music aficionado, but a couple years ago I heard a song by Tim McGraw called “Live Like You Were Dying”. If you’re familiar with it, you know it sends a strong message. If you want to read the lyrics or listen to the song, click this hyperlink and enjoy.

Year-End Essentials

Ask yourself, am I in the same place in life as when I last considered planning goals that matter most to me and my family. Do I still have the same primary vision for my life? Do my savings still align with meeting my expectations for the future and is it in the correct place to go where I’ve intended?

Consider even simpler things, too. Do I still have the same relatives or beneficiaries, or has my family situation changed? Am I working because I want to, or because I need to? Have I recently experienced, or am I about to experience, a major financial event such as selling a business, selling a home, or receiving an inheritance?

Our mission is simple: to ask the questions that matter and deliver tailored solutions, so your money works toward what matters most to you. Markets may be unpredictable, but your personal financial plan should always reflect your goals, values and priorities.

Through years of sitting down and working with families on reaching their planning goals, we’ve learned that a successful financial blueprint can be built on four core pillars

Proactive Tax Planning
Risk Management
Legacy Planning
Tailored Income Planning

We have also found that, with proactive planning, each of these pillars offers the benefit of being firmly within our control and together can be the most impactful drivers in helping us achieve our goals.

I. Proactive Tax Planning

1. Income & Cash Flow

Do I anticipate my family income to increase or decrease in the upcoming year? If so, what is the source of that change?
Have I reviewed my employer-sponsored plan for additional opportunities to manage taxes (e.g., pre-tax contributions, deferrals, or employer benefits)?

2. Retirement & Savings

Have I maximized contributions to retirement accounts as part of my overall savings strategy?
Have I reviewed my savings and investment strategies to ensure assets are held in the most tax-appropriate accounts?

3. Tax Strategies & Coordination

Would I like the Winn Partners team to coordinate with my CPA on strategies for managing deductions or organizing savings in a tax-efficient manner?
Do I have major gains or losses outside of Winn Partners that should be coordinated to ensure proper tax management?
Have I discussed how tax-efficient vehicles—such as insurance—are being implemented into my tax plan?
Are we proactively staying in touch with my tax planning specialist?

4. Philanthropic Tax Planning

Am I interested in aligning my philanthropic goals with tax strategies—such as maximizing deductions or creating a family charitable giving plan?

II. Risk Management

1. Healthcare Planning in Retirement

Have I considered how future healthcare costs could impact my retirement income?
Do I understand how Medicare, supplemental insurance, and long-term care coverage work together in my retirement plan?
Have I planned for the possibility of needing extended care (home health, assisted living, or nursing care)?
Have I reviewed whether my current healthcare strategy is sufficient to protect my retirement savings from medical expenses?

2. Investment Risk Management

Do I understand how much risk my current portfolio carries and whether it matches my goals and comfort level?
Have I stress-tested my investments for market downturns or unexpected volatility?
Is my portfolio diversified across different asset classes to reduce exposure to concentrated risks?
Am I revisiting my risk tolerance regularly to reflect changes in my life stage, goals, or financial needs?

3. Guarding Against Unexpected Loss of Income Due to Premature Death

Have I calculated the financial impact my family would face if I passed away unexpectedly?
Do I have the right amount and type of life insurance coverage in place to protect my family’s income needs, debt obligations, and long-term goals?
Have I coordinated my insurance coverage with my estate and legacy planning?
Is my beneficiary information up to date and aligned with my overall financial plan?

III. Legacy Planning

1. Reviewing Beneficiaries & Legal Account Titling

Have I reviewed my beneficiaries recently to ensure they reflect my current wishes and family circumstances?
Are my retirement accounts, insurance policies, and transfer-on-death accounts titled correctly and aligned with my estate plan?
Do I understand how my assets will transfer (probate vs. non-probate) under my current account titling?
Have I coordinated with my estate attorney to make sure my legal documents—such as wills, trusts, and powers of attorney—are up to date?

2. Legacy Investment Strategies

Have I considered whether my investment strategy reflects both my lifetime needs and the legacy I want to leave behind?
Do I want to earmark certain investments or accounts for specific heirs, charitable organizations, or family causes?
Have I explored tax-efficient strategies for passing wealth, such as gifting, donor-advised funds, or trusts?
Is my current portfolio structured to provide both income for me and growth potential for my heirs?

3. Insurance Strategies

Do I have life insurance in place that supports my legacy goals (e.g., providing for heirs, funding estate taxes, or leaving charitable gifts)?
Have I reviewed whether permanent insurance could serve as a tool for wealth transfer or charitable giving?
Does my current insurance strategy coordinate with my estate plan to avoid unintended tax burdens for my heirs?
Have I considered how insurance can create liquidity for my estate, ensuring other assets don’t need to be sold under unfavorable conditions?

Years ago, we developed a proprietary Life Insurance Evaluation Detector module (we like to refer to it as the LIE Detector) as part of our flagship Stability In Motion (SIM) Financial Planning system. Our SIM System also includes processes for analyzing your entire financial plan and developing your best path forward to create your most meaningful outcomes. If you’d like to learn more about our SIM system and how it may benefit you and your family, just let us know.

IV. Tailored Income Planning

1. Reviewing My Financial Plan

Have I reviewed my financial plan recently to ensure my income strategy still aligns with my retirement and lifestyle goals?
Have any life changes (family, career, health) shifted my income needs or timelines?
Does my current plan provide a clear picture of how long my resources will last under different scenarios?

2. Investment Strategies & Tax Efficiency

Have I reviewed my investment strategies to make sure they are optimized for generating income?
Am I maximizing tax efficiency by holding the right assets in the right types of accounts (taxable, tax-deferred, or tax-free)?
Have I considered strategies such as Roth conversions, tax-loss harvesting, or municipal bonds to enhance income after taxes?

3. Investment Vehicles for Income & Protection

Have I evaluated investment vehicles specifically designed to provide consistent income, such as bond ladders, dividend-paying funds, or annuities?
Am I comfortable with the balance between generating income and protecting against market volatility or principal loss?
Have I considered how insurance-based products or structured notes could play a role in protecting income streams?

4. Reviewing Pensions & Social Security

Have I reviewed my pension benefits and determined the best payout option for my circumstances?
Have I created a strategy for when to begin taking Social Security to maximize lifetime benefits?
Have I coordinated my Social Security and pension decisions with my overall income plan to ensure tax efficiency and sustainability?

Winn Partners Financial Group offers Securities through International Assets Advisory, LLC (“IAA”) – Member FINRA/SIPC. Advisory services offered through International Assets Investment Management, LLC (“IAIM”) or Global Assets Advisory LLC (“GAA”) –SEC Registered Investment Advisors.

Disclosure

Securities offered through International Assets Advisory, LLC (“IAA”) – Member FINRA/SIPC. Advisory services offered through International Assets Investment Management, LLC (“IAIM”) or Global Assets Advisory LLC (“GAA”) – SEC Registered Investment Advisor(s). IAA, IAIM, and GAA are affiliated entities.

The information provided is based on carefully selected sources, believed to be reliable, but whose accuracy or completeness cannot be guaranteed. Any opinion herein reflects our judgment at this date and is subject to change without notice. This should not be construed as an offer or solicitation to buy or sell securities. This information is not intended to be legal or tax advice. Please consult a tax, legal, or financial professional with questions.

Investors should consider the investment objective, risks, and charges and expenses before investing. Different types of investments involve varying degrees of risk, and there can be no assurance that any specific investment will be either suitable or profitable for a client or prospective client’s wealth management investment portfolio. Past performance is not an indication of future performance. International Assets Advisory, LLC and its affiliates, employees and/or directors may have positions in these securities, and may as principal or agent, buy from or sell to customers. All securities are subject to price and yield change and subject to availability. Investments in securities and insurance products are: NOT FDIC-INSURED/NOT BANK-GUARANTEED/MAY LOSE VALUE. Stocks, options, and mutual funds are subject to market volatility and may lose value. Mutual funds, Unit Investment Trusts and Variable Annuities are sold by prospectus only. Please read the prospectus carefully for important information about fees and risk considerations. Bonds are subject to changes in interest rates, risks of defaults by issuer, and the loss of purchasing power due to inflation, or the risk that an issuer will be unable to make interest or principal payments. Additionally, bonds and short-term investments entail greater inflation risk than stocks. Any fixed-income security sold or redeemed prior to maturity may be subject to a substantial gain or loss. Investing in securities underlying in currencies other than the U.S. dollar involves certain considerations comprising both risk and opportunity not typically associated with investing in U.S. securities. The security may be affected either favorably or unfavorably by fluctuation in the relative rates of exchange between currencies, by exchange control regulations, or by indigenous economic and political developments.

Planning Ahead