AI Will Not Replace a Great Advisor. It Will Almost Certainly Replace a Good One

And why some clients will need a human in the room more than ever. 

I want to say something that I think a lot of people in my industry are afraid to say out loud.

Artificial intelligence is going to replace a great many financial advisors over the next decade. Probably most of them. The advisors who run a tidy practice doing solid, competent work – gathering documents, building plans in commercial software, rebalancing portfolios on a quarterly schedule, screening for tax-loss harvesting opportunities, drafting client letters that sound like every other client letter – those advisors are in real trouble. Not because they are bad at their jobs. Most of them are quite good. They are in trouble because the things that make them good are the things AI can now do faster, cheaper, and at three in the morning.

I am not predicting this from a distance. I use AI every day in my own practice. Anyone in my industry who tells you the technology is overrated has not actually used it. It is not overrated. It is one of the most consequential tools to come into financial services in my career, and it is improving on a timescale that should make every advisor pay close attention.

So let me be clear about what I am claiming and what I am not. I am not claiming that the human advisor disappears. I am claiming that the bar for being worth what you cost is rising quickly and that the people who used to settle for a good advisor will, before long, get a better version of that good advisor for free, or close to it, from a chatbot. The gap that survives is between the great advisor and the AI. And great is harder to define than most of my colleagues like to admit.

What AI is genuinely good at – and what “good” advisors mostly do

If you sit down and list the actual tasks a competent advisor performs in a typical week, a sobering thing happens. Most of them are tasks AI either already does well or is about to. Pulling in a client’s documents and summarizing what is in them. Comparing two retirement scenarios. Calculating a Roth conversion. Drafting a quarterly letter. Researching a tax law change. Evaluating an annuity contract. Building a cash flow projection. Spotting a missed beneficiary designation.

None of this is glamorous work, but it is most of the work. And it is the work that, until very recently, justified a full time person doing it. That justification is eroding. Software that costs a client $30 a month can now do a credible first pass on most of these tasks, and within a few years it will do a near-final pass. The advisor who built a career on being the diligent middle layer between the client and the financial machinery is being replaced from underneath by a tool that does the diligent middle layer for free.

That is the bad news. Now the good news, which is also the more interesting news.

The clients AI cannot serve well

There is a category of client for whom AI will never fully be enough, and the reason has nothing to do with technology. It has to do with the structure of the problems they are trying to solve. In my experience, three characteristics tend to define this group. Many of the people I work with fit these characteristics. The clients who need a great advisor likely have all three.

First, complicated financial situations. I am not talking about a household with a 401(k), a Roth IRA, and a mortgage. AI handles that beautifully. I am talking about the business owner whose personal balance sheet is wound around an operating company, a holding LLC, a real estate entity, and a buy-sell agreement that has not been updated since the partner left. I am talking about the family that has wealth flowing across two generations, with trusts that were drafted in different decades by different attorneys with different assumptions. I am talking about the executive whose compensation includes restricted stock, performance shares, deferred comp, and a non-qualified plan that interacts with their cash flow in ways that change every year. AI can produce a remarkably good overview of any one of these pieces. Where it struggles is in the connective tissue, the place where the entity structure, the estate plan, the tax exposure, the family dynamics (always the gasoline on the fire!), and the operating reality of a closely held business all touch each other. That is where decisions actually live, and that is where the analysis is messy enough, and the data is incomplete enough, that you need a human who has seen this kind of mess before.

Second, a high regularity of consequential decisions. Some clients live a financial life with very few decision points. They save into their plan, they hold a diversified portfolio, they rebalance on a schedule, they retire on a date, and most of the work is just steady execution. They benefit enormously from a sound plan and a low-cost portfolio, and frankly, AI can carry a lot of that load. But other clients face a steady drumbeat of real decisions. Should I take the buyout offer or hold out for a better one? Do I exercise the options now or wait? Should we sell the second home or keep it? Do we lend to our son’s startup or write a check we cannot ask back for? Do I move the trust to a different state? Do I take the partnership stake? Do I retire in eighteen months or push it three more years? When decisions of this kind arrive every few weeks rather than every few years, you do not need a tool. You need a thinking partner, someone who knows your situation cold, who you trust, who you can call on a Tuesday afternoon and say, here is what I am turning over in my head, what am I missing? That kind of relationship is not something a chat window provides, no matter how clever the chat window gets.

Third, high consequences and costs attached to those decisions. A wrong move on a $40,000 401(k) contribution is forgivable. A wrong move on a $40 million liquidity event is not. A misread on the timing of a Roth conversion can cost a few thousand dollars; a misread on the structure of a business sale can cost seven figures and a strained relationship with a sibling. When the dollar amounts get large enough, or when the decisions become irreversible enough, the value of being right goes up, and the value of being wrong goes up faster. Clients in this position are not paying for information. They are paying for judgment under pressure, and they are paying for someone to share the weight of the decision with them. That is fundamentally a human service. It always has been. AI does not change it. If anything, AI raises the stakes, because the people on the other side of these transactions…the buyer, the IRS, the opposing trustee, the estate attorney…are using AI too, and the playing field at the high end is getting more sophisticated, not less.

What “great” actually means now

I have been thinking a lot about what separates the advisors who will thrive in the next ten years from the ones who will not, and a lot about the clients who will need them. It is not credentials. It is not technical knowledge.  AI is a great equalizer on technical knowledge, and the playing field there is collapsing fast. There is no longer a scarcity premium added to knowledge.  The advisors who will thrive are the ones who do the work AI cannot do, and that work has a specific shape.

It is the work of being a thinking partner before a decision, not just a report generator after one. It is the work of pushing back when a client wants to do something you believe will hurt them, and doing it in a way they can hear. It is the work of holding a conversation across years, remembering what the client said three Christmases ago about their daughter, and connecting it to what is being decided this Tuesday. It is the work of judgment in places where the data is incomplete, the stakes are real, and the answer is not in any model. It is, in a word, presence.  The kind of presence that does not scale, cannot be automated, and is exactly the thing that the right kind of client will pay for as long as I am alive to provide it.

If you are a client of mine reading this, I want you to know I take this seriously. I am using every AI tool I can get my hands on, not to replace what I do for you, but to free up more of my time and attention for the part of the job that actually matters when your number is called. The diligent middle work…the research, the modeling, the document review, the first drafts…should be done faster and cheaper every year. That is good for you. The real work, the conversation that happens when something hard is on the table and you need someone in the room with you, is exactly where I want to be spending more of my time, not less.

And if you are reading this and wondering whether you have the kind of financial life that justifies a great advisor – whether the complexity, the decision velocity, and the stakes really warrant the relationship – that is a fair question to ask. For some people, the honest answer is no. A good chatbot, a target-date fund, and a disciplined savings habit will get them where they are going. For others, the answer is firmly yes, and the cost of being wrong about it is too high to leave to a tool that, however brilliant, has no skin in your game.

Knowing the difference is itself a financial decision. And it might be the most important one you make this year.

 

Four Common Money Questions, Answered in Plain English

At Ridgeline Wealth Advisors, we believe financial literacy should feel practical, not intimidating. Here are four common questions we hear, with straightforward answers to help you think clearly about cash, investing, and market headlines.

Is investing in gold or other metals worth it?

Maybe for some people as a small, specialized part of a broader plan—but not as a guaranteed shield against inflation or market stress.  Gold has had significant price swings and has not reliably tracked inflation over long periods. If someone is focused specifically on inflation protection, Treasury Inflation-Protected Securities, or TIPS, have historically been a more direct inflation-linked tool, though no approach is perfect.

Possible benefits of precious metals can include:

  • Diversification in some environments
  • A tangible asset some people find psychologically reassuring
  • Potential value during certain inflationary or crisis periods

But there are also tradeoffs:

  • Prices can be volatile
  • Gold is not an investment…there are no future expected cash flows so no way to discount cash flow to determine a fair present value share price.  It is pure speculation.
  • Metals generally do not pay interest or dividends
  • Physical ownership can involve storage, insurance, and transaction costs
  • Tax treatment can differ from stocks and mutual funds

At a high level, physical gold and many precious metals are generally taxed when sold. Some structures may be treated as collectibles, which can mean different tax treatment than stocks. Some gold ETFs may also be taxed differently depending on how they hold the metal. In some states, sales tax may apply when buying physical metals.

In short, precious metals may have a role for some investors, but they are not a one-size-fits-all solution.

What does it really mean when the stock market drops, and when should we worry?

A market drop usually means investors are willing to pay less for many publicly traded companies than they were willing to pay before. That can feel unsettling, but downturns are a normal part of investing and the ‘price of admission’ to get higher expected returns in the long-term. Short-term volatility by itself is usually not a reason to abandon a long-term plan. The better question is often not, “What is the headline today?” but, “Have my own needs changed?”

The S&P 500 is a widely followed index of 500 large U.S. companies, so it is often used as a quick snapshot of how large U.S. stocks are doing. But indexes are not available for direct investment and do not reflect actual portfolio expenses.

Market declines can be uncomfortable, but they are also part of how long-term investing works. For many people, the more important issue is whether their own liquidity needs, time horizon, or risk tolerance have changed—not whether markets are simply having a difficult week.

Is it ever okay to keep cash in a shoebox or under your mattress?

A small amount of physical cash for convenience is a personal choice. But for reserve cash, source materials support prioritizing liquid, interest-earning, FDIC-eligible options over storing large amounts at home.  An emergency fund, or protective reserve, exists to help cover unexpected expenses and near-term spending needs without forcing you to sell long-term investments at the wrong time. The exact amount depends on your situation, but the core idea is simple: keep enough cash accessible for real-life surprises.

There is also a tax angle. Money in a savings account may earn taxable interest. Cash at home does not generate taxable interest because it earns nothing. But that comes with tradeoffs: cash at home is easier to lose, steal, or destroy, and it can be harder to document.

How does a CD work?

A certificate of deposit, or CD, is a bank savings product. You agree to leave money at the bank for a set term—such as 3 months, 1 year, or 5 years—and in exchange the bank pays a fixed interest rate. If you take the money out early, the bank will usually charge an early withdrawal penalty. When the CD reaches maturity, you can typically:

  • Withdraw the money
  • Move it into a new CD
  • Let it renew automatically, depending on the bank’s terms

At a high level, CD interest is generally taxable as ordinary income in the year it is credited or made available, even if you do not withdraw it. Banks typically report that interest on Form 1099-INT. Early withdrawal penalties may be deductible on a federal return, and state tax treatment can vary.

Closing Thought

Good financial decisions often start with matching the tool to the goal: cash for short-term needs, savings vehicles for reserves, and long-term investments for long-term objectives.  Most financial options are not bad tools to have in the toolbox as long as you know when it’s appropriate to use which tool.  Don’t let me find you trying to fix your mirror with a hammer…it won’t go well.  Neither will using the incorrect financial tool.

The 3 Biggest Tax Questions We’re Hearing Right Now

Every year brings its share of tax changes, but 2026 is different. The One Big Beautiful Bill Act, signed into law on July 4, 2025, made sweeping updates to the federal tax code — some permanent, some temporary, and nearly all of them generating questions from the families and individuals we work with. Rather than try to cover everything at once, we wanted to focus on the three topics that have come up most often in recent conversations and break them down in plain language.

“How Does the New SALT Deduction Cap Affect Me?”

If you live in a state with meaningful income or property taxes, you’ve probably felt the sting of the $10,000 cap on the state and local tax (SALT) deduction that’s been in place since 2018. Good news: the new law raises that cap to $40,000, effective for the 2025 tax year. For 2026, it ticks up to $40,400 and will continue increasing by one percent annually through 2029.

For a household earning $400,000 and paying $30,000 in combined state income and property taxes, this is a significant change. Under the old rules, only $10,000 of that was deductible. Now, the full $30,000 qualifies. That’s a real reduction in taxable income.

However, the expanded cap comes with an income-based phaseout. If your modified adjusted gross income exceeds $500,000 (or $250,000 for married filing separately), the cap is reduced by 30 cents for every dollar above that threshold. By the time income reaches roughly $600,000, the deduction phases back down to $10,000. So a couple earning $550,000 would see their maximum SALT deduction reduced to about $25,000 — still much better than $10,000, but not the full benefit.

A few things worth noting. First, if you’ve been taking the standard deduction because the old SALT cap made itemizing less worthwhile, it’s time to run the numbers again. Second, business owners using pass-through entity tax elections can still deduct state taxes at the entity level — the new law didn’t restrict that workaround. And third, this expansion is temporary. The cap reverts to $10,000 in 2030, which means there’s a planning window worth being intentional about.

“With the Estate Tax Exemption at $15 Million, Do I Still Need an Estate Plan?”

For years, families were on edge about the federal estate tax exemption. Under the 2017 Tax Cuts and Jobs Act, the exemption had been roughly doubled to about $14 million per person, but it was set to drop back to around $7 million at the end of 2025. The new law resolved that uncertainty by permanently raising the exemption to $15 million per individual — $30 million for married couples — effective January 1, 2026. Beginning in 2027, it will be indexed for inflation, and unlike the prior law, there’s no sunset provision.

So does that mean estate planning is no longer necessary? Not at all. The federal exemption is only one piece of the puzzle. Eighteen states plus the District of Columbia impose their own estate or inheritance taxes, often with much lower thresholds — in some cases as low as $1 million. A couple with $20 million in assets might owe nothing federally but could face a significant state tax bill depending on where they live.

Beyond taxes, a good estate plan addresses guardianship for minor children, powers of attorney, the orderly transfer of business interests, and probate avoidance. These things matter regardless of exemption levels.

The higher exemption also creates interesting planning opportunities. If your estate is comfortably below $15 million, the focus may shift from estate tax reduction toward income tax efficiency. Holding appreciated assets until death to take advantage of the step-up in basis, for example, could eliminate capital gains taxes on decades of growth. On the other hand, families with larger estates should continue using trusts and other transfer strategies, because the 40 percent federal estate tax rate on amounts above the exemption hasn’t changed.

“What Are All These New Deductions I Keep Hearing About?”

The new law introduced several targeted deductions that are genuinely new to the tax code. Here are the ones generating the most conversation.

Tips. Workers who receive tips can now deduct up to $25,000 in tip income from their taxable earnings. This applies to anyone in a tipped occupation — servers, hairstylists, rideshare drivers, and more — and it’s available whether you itemize or take the standard deduction. The deduction phases out at higher income levels and is temporary, running through the 2028 tax year.

Overtime. Overtime wages now qualify for a similar above-the-line deduction. If you earn time-and-a-half or double-time under the Fair Labor Standards Act, a portion of that income may be deductible. This is aimed at hourly and non-exempt workers, and it requires that your employer accurately report overtime pay on your W-2.

Auto loan interest. Perhaps the most surprising new break: interest paid on auto loans is now deductible up to $10,000 per year. This applies to personal vehicles, not just business ones. The deduction phases out starting at $100,000 of adjusted gross income for single filers ($200,000 for joint filers) and is fully eliminated at $150,000 ($250,000 for joint filers). Your lender is required to provide a statement of interest paid by January 31.

Senior deduction. Taxpayers 65 and older can claim a new deduction of up to $6,000 per qualifying individual, or $12,000 for married couples filing jointly where both spouses qualify. This sits on top of the existing standard deduction and the additional standard deduction for seniors. It phases out at six percent of modified adjusted gross income above $75,000 for single filers ($150,000 for joint filers) and is available for tax years 2025 through 2028.

Higher standard deduction. Finally, the standard deduction itself increased to $32,200 for married couples filing jointly, $16,100 for single filers, and $24,150 for heads of household for the 2026 tax year. These higher amounts are now permanent.

Putting It All Together

The common thread across all three of these topics is that the tax landscape has shifted in ways that create real opportunities — but also real complexity. Some provisions are permanent, others expire in a few years, and many come with income-based phaseouts that can change the math quickly depending on your situation.

Our advice? Don’t assume last year’s strategy still works. Whether it’s revisiting whether to itemize, rethinking your estate plan, or making sure you’re capturing every new deduction available to you, a fresh look at your tax picture is well worth the effort. As always, we’re here to help you think through it.

This article is provided for educational purposes only and does not constitute tax, legal, or investment advice. Tax laws are complex and individual circumstances vary. Please consult with a qualified tax professional or your financial advisor before making any decisions based on the information presented here.

New Tax Season, New Tax Code: What Changed In 2026 – And Why It Matters

As we approach another tax filing season, it’s a good time to take stock of the most meaningful changes that affect U.S. taxpayers for the 2026 tax year (returns you’ll file in 2027). This year’s filing period reflects not just inflation adjustments but also significant provisions of the One, Big, Beautiful Bill Act (OBBBA), the major tax law signed in 2025 that locked in and updated several key tax provisions. (IRS)

Understanding these changes can help you plan earlier in the year — not just react at tax time.

Key 2026 Tax Changes at a Glance

Below are three major areas where taxpayers will see meaningful adjustments for the 2026 tax year:

1) Updated Federal Income Tax Brackets

The IRS annually adjusts tax brackets for inflation. For 2026, the seven familiar federal income tax brackets remain (10%, 12%, 22%, 24%, 32%, 35%, 37%), but the income thresholds have shifted upward, helping many taxpayers avoid “bracket creep.”

2026 Federal Income Tax Brackets (Taxable Income) (OneDigital)

Tax Rate

Single Filers

Married Filing Jointly

10%

Up to $12,400

Up to $24,800

12%

$12,401–$50,400

$24,801–$100,800

22%

$50,401–$105,700

$100,801–$211,400

24%

$105,701–$201,775

$211,401–$403,550

32%

$201,776–$256,225

$403,551–$512,450

35%

$256,226–$640,600

$512,451–$768,700

37%

Over $640,600

Over $768,700

These adjustments don’t lower rates, but they mean you can earn more before moving into a higher bracket. That matters for retirement planning, RMD timing, Social Security taxation, and portfolio withdrawals.

2) Standard Deduction and Senior Deduction Updates

Along with bracket changes, the standard deduction rises for most taxpayers. For 2026:

  • $16,100 for single filers
  • $32,200 for married couples filing jointly
  • $24,150 for heads of households (NerdWallet)

For many taxpayers, these deduction increases reduce taxable income before rates are even applied.

Additionally, OBBBA introduced a new senior deduction lasting through 2028: taxpayers age 65 or older may be eligible for a $6,000 deduction ($12,000 if both spouses qualify), regardless of whether they itemize or take the standard deduction. (AARP)

3) Expanded Credits and Other Key Changes

The 2026 tax year also reflects broader changes that can impact refunds or tax liabilities:

Child Tax Credit: Indexed for inflation and slightly increased under the OBBBA for qualifying children. (IRS)

Itemized Deduction Changes: The bill significantly expanded the cap on state and local tax (SALT) deductions for many filers, although limits and phaseouts still apply.

Charitable Deductions: Non-itemizers can now deduct cash donations up to $1,000 (single) or $2,000 (joint) – a change that broadens tax benefits to more filers.

Preparation and Filing Notes: The IRS has updated forms, encouraged direct deposit for refunds, and provided resources and checklists for this filing season. (IRS)

Why This Matters for Your Planning

These tax changes are not just numbers on a chart – they affect when and how you plan income, retirement distributions, Social Security strategies, Roth conversions, and charitable giving.

Some actionable reminders for 2026 and beyond:

  • Review whether standard vs itemized deductions benefit you (especially with SALT changes).
  • Consider the timing of income that could push you into higher brackets.
  • Coordinate retirement distributions with Social Security claiming to manage taxable income.
  • Use expanded credits and deductions to your advantage throughout the year, not just at filing time.

Taxes are a major lifetime expense – often bigger than market returns or fees. Planning with the current tax code in mind helps you make decisions that support the life you want to live.

 

Finding Meaning In Retirement: When The Calendar Is Full But The Soul Isn’t

For many people, retirement planning starts with a number.

“How much do I need?”
“Will my money last?”
“Can I afford to stop working?”

Those questions matter. But after years of walking alongside retirees, we’ve learned something important: financial security alone does not guarantee fulfillment.

In fact, one of the most common challenges retirees face has very little to do with money. It’s the quieter, often unexpected loss of purpose, identity, and connection that can surface once work is no longer the organizing force of daily life.

The Transition No One Warns You About

Work does more than generate income. It provides structure, responsibility, and a sense of contribution. It answers questions we don’t always realize we’re asking:

Who needs me today?
What am I accountable for?
Where do I belong?

When work ends, freedom arrives – and for many, so does a subtle sense of disorientation.

Research supports this experience. Multiple studies show that retirement can lead to a measurable decline in a person’s sense of purpose if it isn’t replaced intentionally. This highlights the guidance we give to clients years in advance of retirement: make sure that you are retiring toward something and not just away from something.

One large review published in The Gerontologist highlights how meaning, not activity alone, plays a central role in how well individuals adjust to retirement. In other words, staying busy is not the same as feeling fulfilled.

Activity Is Not the Same as Meaning

We often meet retirees who are financially secure, healthy, and “doing all the right things” – traveling, golfing, volunteering, and staying active. Yet something still feels missing.

That’s because meaning tends to come from deeper sources.  These can include:

  • Contribution – being genuinely useful to others
  • Connection – relationships that go beyond surface-level social interaction…make note, fitting in is NOT the same thing as true authentic connection
  • Growth – continuing to learn, stretch, and engage with life

Psychology research consistently shows that retirees who maintain a strong sense of purpose experience better mental health, greater life satisfaction, and even improved physical outcomes.

Designing Retirement With Intention

The most fulfilling retirements we see are not accidental. They are designed with the same thoughtfulness people once applied to their careers.

That might look like:

  • Remaining involved in a part-time, advisory, or mentoring role
  • Sharing hard-earned wisdom with younger professionals or family members
  • Committing to a cause, board, or organization where presence truly matters
  • Creating weekly rhythm and responsibility, not just open time
  • Pursuing challenge and adventure, not just comfort

Research on “meaning-making” in retirement suggests that individuals who actively redefine who they are after work – rather than simply replacing work with leisure – experience a far healthier transition. The key question is not “How do I stay busy?”
It’s “Who do I want to be useful to in this season of life?”

Planning for a Meaningful Life, Not Just a Long One

Good financial planning creates margin. Great planning helps you use that margin well.

When we talk with clients about retirement, we often ask non-traditional questions:

  • What will give your days structure?
  • Who will you see regularly?
  • Where will you feel needed?
  • What are you still growing toward?

Organizations that focus on thriving in retirement, not just retiring, emphasize the same themes: purpose, connection, and intentional transition.  Money supports those answers – but it cannot replace them.

If retirement is approaching, or already here, it’s worth stepping back and asking not just “Can I retire?” but “What am I retiring to?”

That question matters more than the number if you truly want to continue to live your great life. In fact, retirement done well starts looking much more like exchanging one work purpose for a different kind of purpose. Retirement is not the Great Checkout if you want to thrive. So let’s all agree to stop using retirement as a goal to ‘be done,’ and start viewing it as financial freedom to pursue the things that make us feel most alive (Contribution, Connection, and Growth)! 

Planning 2026 with intention: 10 financial and life considerations for the year ahead

The start of a new year naturally invites planning. But for most people, planning quickly turns into optimization – more efficiency, better returns, tighter projections.

The more meaningful work often starts earlier than that.

Before adjusting numbers, it’s worth stepping back to ask whether your financial life is aligned with the life you want to live. As we look ahead to 2026, with several new planning rules and legislative changes becoming active under the OBBBA framework, this is an ideal moment to reset both direction and strategy.

As a kid of the ‘90’s and a David Letterman fan, I always waited for the part of the show when he revealed his (sometimes crazy, but almost always funny) Top 10 List.  Here is my attempt and a nod to Mr. Letterman with 10 financial and life planning considerations worth reviewing as you prepare for the year ahead, with a particular emphasis on building margin, clarity, and adventure into 2026.

1. Define What You Want 2026 to Feel Like

Before reviewing accounts or projections, clarify the experience you want the year to deliver.

Do you want 2026 to feel spacious or packed? Grounded or mobile? Predictable or exploratory?

Financial plans are most effective when they support a clearly defined life vision. Without that anchor, even strong financial results can feel disconnected.

2. Plan Adventure First, Not Last

Adventure is often treated as optional – something to squeeze in if time and money allow.

In practice, that usually means it doesn’t happen.

Whether adventure for you means extended travel, meaningful family trips, endurance events, or simply more time outdoors, plan it intentionally. Block the time on the calendar. Estimate the cost. Create a dedicated savings bucket.

When adventure is designed into the plan, money becomes an enabler rather than a gatekeeper.

3. Understand What’s Changing Under the OBBBA

Several provisions tied to recent federal budget and benefits legislation are now becoming relevant for 2026 planning. While the specifics vary by household, common planning areas affected include retirement contribution limits, including updated catch-up provisions for certain age ranges; required minimum distribution rules and beneficiary timelines impacting inherited retirement accounts; income thresholds for tax credits and deductions, with tighter phase-outs at higher income levels; and sunsetting provisions from earlier tax law, increasing the importance of proactive, multi-year tax planning.

The key takeaway is that understanding these changes early creates flexibility. Waiting until year-end often removes good options.

4. Revisit Your “Enough” Number

As income and assets grow, old targets often linger long after they stop serving your life.

Revisit what level of income actually supports your desired lifestyle, how much work is enough, and which trade-offs are no longer worth it.

Clarifying “enough” is often the most powerful financial decision you can make.

5. Align Cash Flow With Experience, Not Habit

Instead of asking where to cut spending, ask where your money is working well for you.

Which expenses consistently add meaning or enjoyment? Which ones feel automatic or outdated?

Redirecting cash flow toward experiences, travel, and flexibility often improves quality of life without increasing overall spending.

6. Strengthen the Safety Net

Adventure is easier to pursue when the foundation is solid.

The new year is a good time to review emergency reserves, insurance coverage, estate documents, and beneficiary designations.

These items rarely feel urgent – until suddenly they are. Proactive review reduces stress and creates confidence.

7. Simplify Where Complexity Has Crept In

Over time, financial lives naturally become more complex.

Multiple accounts serving similar purposes, legacy strategies that no longer apply, and complexity that adds confusion without value can quietly accumulate.

Simplification improves clarity, reduces friction, and makes decision-making easier when life changes quickly.

8. Use Tax Planning to Support Lifestyle Decisions

With updated thresholds and evolving rules, tax planning for 2026 should align with life choices.

This may include timing income around travel or sabbaticals, evaluating Roth strategies during lower-income years, or coordinating charitable giving with tax efficiency.

The goal is not minimizing tax in isolation, but ensuring tax decisions support the life you want to live.

9. Decide What to Stop Doing

Borrowing from the annual review approach popularized by Tim Ferriss, one of the most powerful planning exercises is deciding what to stop.

What commitments, habits, or financial behaviors create stress without meaning, consume time without return, or reflect an outdated version of you?

Stopping often creates more freedom than starting something new.

10. Build Margin Into the Plan

Finally, leave room.

Margin in your calendar allows spontaneity. Margin in your cash flow absorbs surprises. Margin in expectations builds resilience.

A plan with no margin may look efficient, but it is fragile. A plan with margin can flex and support opportunity when it appears.

Final Thought

Planning for 2026 isn’t about predicting every outcome. It’s about creating a framework strong enough to support responsibility and exploration.

When financial planning is aligned with experience, when adventure is treated as essential rather than optional, and when decisions are made intentionally rather than reactively, money becomes what it was always meant to be – a tool in service of a well-lived life.

The top 8 financial items to review before the end of the year

As the year draws to a close, many people feel an instinct to wrap things up. It’s a natural moment to pause, take inventory, and make sure nothing important is left undone.

In financial planning, year-end reviews aren’t about scrambling or chasing last-minute tactics. Done well, they’re about clarity – confirming that your financial decisions still align with the life you’re building.

Here are the most important areas worth revisiting before the calendar turns.

  1. Taxes: Reducing Regret, Not Just the Bill

    Year-end tax planning isn’t about perfection – it’s about intention. This is the time to review realized gains and losses, assess whether tax-loss harvesting makes sense, and confirm that income timing aligns with your broader strategy. For many families, charitable giving also plays a role here – not as a tax trick, but as a thoughtful extension of their values.

  2. Required Minimum Distributions (RMDs)

    For retirees and those nearing retirement, RMDs deserve careful attention. Confirming distributions are made on time, in the correct amount, and from the appropriate accounts is critical. It’s also worth reviewing how RMDs integrate with your overall cash-flow plan. This is ideally done in the first half of the year, but if you haven’t gotten to it yet, do not delay. The penalty for missing your RMD is significant!

  3. Charitable Giving with Purpose

    Year-end giving often happens quickly. A pause can make it more meaningful. Review how and where you give, and whether you’re giving still reflects what matters most to you. Going back to your RMD’s, if you are over 70.5, you can consider using a Qualified Charitable Distribution (QCD) from your IRA to fund those giving goals!

  4. Portfolio Alignment and Risk Exposure

    Markets have a way of feeling louder in December. Year-end is a natural time to rebalance, reassess concentration, and confirm that your portfolio still supports your long-term plan. Have you set aside enough funds in safe cash and short-term bonds to match several years’ worth of coming expenses? If you’re not sure, we should talk.

  5. Estate Planning and Beneficiary Reviews

    Time with family has a way of surfacing important questions. Review beneficiary designations, trustee and executor choices, and guardianship decisions if applicable. Your beneficiary designations on retirement accounts, insurance policies, etc. are legal agreements between you and the financial institution. This means that what ever is on file will trump what is stated in your will, so make sure they line up!

  6. Retirement Readiness Beyond the Numbers

    For those approaching retirement, year-end reflection often brings deeper questions. Financial readiness and emotional readiness don’t always arrive at the same time. Both deserve attention. I’ve seen the emotional transition into retirement impact clients much more significantly than the financial transition. Make sure you have spent time preparing yourself for both.  If you are only focused on what you are retiring away from and haven’t spent any time thinking about what you want to retire towards, then you’re not ready.

  7. Simplification and Organization

    Many people enter a new year craving less complexity. Consolidating accounts and reducing unnecessary financial clutter can create a surprising sense of relief. Everyone has a financial ‘junk drawer’, where things accumulate over the years, but have no rhyme or reason or coordination. Spend time emptying out the junk drawer to assess what you have and then be intentional about what you keep and what you get rid of.  Does it serve you anymore? 

  8. Family Support and Legacy Planning

    Supporting adult children or aging parents requires balance. These decisions are rarely about math alone – they’re about boundaries and stewardship. I have noticed that there is no magic formula or one-size-fits-all approach. Every family dynamic is different and requires a thoughtful, intentional approach to what is best for everyone.

Closing the Year Well

A thoughtful year-end review isn’t about checking boxes. It’s about asking:
Does our financial plan still serve the life we want to live?  If it doesn’t or you’re not sure, give us a call….we’re here to help.

Episode 45: What’s worthy of your finitude with Patrick Moody


I love these conversations, but this one was fun.  We hit on the depths of the human condition to drive each of us on to our own adventures.  So what happens when a dedicated trial attorney makes adventure a non-negotiable part of his life? In this episode, I sit down with Patrick Moody, a prosecutor for the state of Montana who refuses to let a demanding career keep him from chasing adventure. From trail running right out his back door to tackling high-altitude mountaineering, Patrick has found a way to integrate the wilderness into his daily routine.

We dive into his experiences traveling across five continents in a single year, climbing some of the world’s most stunning peaks, and even navigating a life-altering arthritis diagnosis that nearly took away his ability to walk. Patrick shares how he mentally and physically pushes through challenges, what drives him to keep pursuing difficult things, and why he believes that truly living means stepping into the unknown. This conversation is packed with insights on adventure, resilience, and making the most of the time we have.

Episode Highlights:

[1:30] – Patrick’s background as a Montana-based attorney and adventure-seeker
[3:15] – Why Helena, Montana is a paradise for outdoor lovers
[6:45] – The shocking arthritis diagnosis that nearly ended Patrick’s ability to move
[10:20] – How he rebuilt his body and got into trail running post-diagnosis
[15:45] – The lessons of adventure: losing a parent young and growing up without wealth
[22:10] – Learning to listen to his instincts on when to push forward and when to turn back
[31:05] – The scariest moment of his mountaineering career—trapped in a lightning storm
[35:55] – A year of adventure: how Patrick traveled to five continents in 2024
[44:30] – The importance of intentionality in adventure, career, and finances
[50:10] – Type 1, Type 2, and Type 3 fun—why suffering is part of the reward

Links & Resources:

Join the Adventure!

If you enjoyed this episode, please leave a rating and review! Follow the show for more inspiring conversations with people who make adventure a priority in their lives. And if this conversation resonated with you, share it with someone who needs a little extra push to chase their own adventure. 🚀 🎙️

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Episode 35: Building Perserverance Through Hardship, Competition and Adventure with Owen Hayden


Join me for a cool conversation with Owen Hayden, a high-energy adventurer, corporate achiever, and former athlete who’s mastered the art of resilience. Owen shares his journey from a high-level sports career to navigating the challenges of the corporate world, all while staying connected to his passion for adventure. We discuss what it takes to push through adversity, the lessons he learned from sports, and his pursuit of grit as a defining trait both on and off the field. Plus, you’ll hear about Owen’s commitment to exploring the world—from Glacier National Park with his young family to Ironman races and rodeos. If you’ve ever been curious about finding purpose and adventure in everyday life, this episode is for you.

Highlights:

  • [00:01:32] Owen’s career journey: From corporate climber to world traveler.
  • [03:00] Hiking Glacier National Park with a baby in tow—tips for family adventurers.
  • [07:00] The power of sports and family in building resilience and grit.
  • [11:30] Learning from loss: how adversity shapes our drive and character.
  • [14:00] Coaches and mentors: the unexpected father figures who shaped Owen’s path.
  • [24:19] Finding a new “team” after sports: how CrossFit and community fill the gap.
  • [32:00] Bucket list adventures: How Owen plans to keep exploring with his family.

Links & Resources:

Thanks for tuning in! If you enjoyed this episode, please consider rating, following, and sharing “On Adventure.” Your support helps us bring you more amazing guests and stories.

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Q1 Letter to Clients

If there’s a message to take from 2023 markets, it is this: Timeless wisdom best informs timely decisions.

Here’s how Morgan Housel describes the same in his new book, “Same as Ever.”

“The typical attempt to clear up an uncertain future is to gaze further and squint harder—to forecast with more precision, more data, and more intelligence. Far more effective is to do the opposite: Look backward, and be broad. Rather than attempting to figure out little ways the future might change, study the big things the past has never avoided.”

Following are a few timeless tenets that offer timely investment insights for the year ahead.

There’s Never a Good Time to Time the Market

Perhaps most obviously, last year demonstrated how randomly—and rapidly—markets can move. As The Wall Street Journal reported at year-end:

“Almost no one thought 2023 would be a blockbuster year for stocks. They could hardly have been more wrong.”

Another financial journal observed:

“What was supposed to go up went down, or listed sideways, and what was supposed to go down went up — and up and up. The S&P 500 climbed more than 20% and the Nasdaq 100 soared over 50%, the biggest annual gain since the go-go days of the dot-com boom. … ‘I’ve never seen the consensus as wrong as it was in 2023,’ said Andrew Pease, the chief investment strategist at Russell Investments.”

Many financial pundits offered elaborate explanations for the year’s fortunes, and why (in hindsight) their projections were so far off. While their reasons may be accurate, the implication is, were it not for this, that, or the other thing, their forecasts would have been correct.

The problem is, there’s almost always “this, that, or the other thing” going on in this big, busy world. Thus, it really should come as no surprise that routine surprises regularly randomize the market’s next moves.

We’ve known this for years—since at least 1973, when Burton Malkiel published the first edition of “A Random Walk Down Wall Street.” Even after 50 years, Malkiel’s message represents one of the most timeless truths explaining why we don’t try to time market trends.

Beware of Catchy Catchphrases

In 2023, just seven stocks within the S&P 500 Index explained almost two-thirds of the index’s total annual gains. Their striking performance scored them the catchy title, “Magnificent Seven.”

What should we expect for this star lineup in the coming year? Search today’s popular press, and you’ll find timely tips galore on whether to bulk up on more magnificence, or sell while the selling is good. Forecasts hinge on the usual suspects: Whether inflation rises or falls, a recession lands or recedes, technologies advance or retreat, and so on.

Taking a more timeless view, we would suggest being wary of celebrated stocks bearing trendy titles. Chasing after stellar returns with their own nicknames may work for a while. But eventually, one of those “surprises” tends to come along, turning once-hot stocks into cold plays.

Which brings us to our next timeless tenet.

Diversification Is Perennially Prudent

Viewing 2023 up close, there may be a temptation to chase after the market’s recent winning streak, bulking up on more of that which has been so pleasantly surprising of late.

Zooming out, our perspective remains unchanged: Maintain a globally diversified portfolio, tailored for your needs. Treat an allocation to the Magnificent Seven (and the next trend, and the one after that) as one of many “pistons” powering the market’s perennial growth. But pair it with effective diversification, to temper the inevitable upsets that await us in the year(s) ahead.

In this spirit, I wish you a well-diversified investment portfolio in 2024, along with abundant concentrations of health, happiness, and harmonious well-being for you and yours.