Ballots, Markets, and the Plan That Outlasts Both

Every election season brings the same question to our conversations, and this fall has been no different: “How is the election going to affect my investments?”

It’s a fair question. Elections matter. They shape policy, taxes, and regulation, and they stir up strong feelings on every side. When so much feels at stake, it’s natural to wonder whether our portfolios should respond.

The research gives a calmer answer than the headlines would suggest.

What the History Shows

Dimensional Fund Advisors has studied US elections and stock market returns going back to 1926. A few findings stand out:

  • Election months haven’t looked unusual. Monthly returns of the S&P 500 in election months have generally fallen well within the typical range of returns, regardless of which party won.
  • No party has had a monopoly on market growth. Over nearly a century, the market has trended upward under Democratic and Republican presidents alike, and under unified and divided control of Congress.
  • Early “winners” haven’t stayed winners. In a study of sector returns from 1928 to 2024, Dimensional found that the sectors that did best during an election month beat the overall market by more than six percentage points on average that month. Over the full presidential term that followed, those same sectors performed roughly in line with the market. Prices adjust quickly to what investors expect from new policies, so the advantage tends to fade.

In other words, by the time an outcome is known, the market has usually already priced it in. Trying to reposition a portfolio around who won, or who might win, has historically been more likely to introduce mistakes than to add value. Dimensional co-founder David Booth put it well: vote with your ballot, not your life savings.

Of course, past performance is no guarantee of future results, and every election brings its own uncertainty. But the long record is a helpful counterweight to the urgency of any single news cycle.

Where the Real Risk Lives

If the election itself isn’t the risk, what is? More often, it’s the decision we make in response to it: selling after a rough week, sitting on cash waiting for clarity, or reworking a long-term plan around a short-term headline.

That’s why we put so much weight on how a portfolio is structured, not just what it holds.

A Steadier Approach: Matching Money to Its Purpose

One approach we return to often is called “liability-driven investing.” The name sounds technical, but the idea is simple. Before deciding how much to invest for growth, we first ask what the money needs to do, and when.

For many families, that list includes things like:

  • The next several years of living expenses
  • Known tax payments
  • Tuition, a home project, or a planned gift
  • Charitable commitments or support for family members

Those near-term needs, the “liabilities,” can be set aside in high-quality, shorter-term assets lined up with when the money will actually be spent. The rest of the portfolio, the part meant for long-term growth, has time on its side.

This doesn’t make markets less volatile. What it does is change what volatility means for you. When the next few years of spending are already accounted for, a choppy month (post-election or otherwise) becomes something to watch rather than something to react to. You aren’t forced to sell growth assets at a bad moment to pay for the life you’re living now.

It’s not a forecast or a bet on any outcome. It’s a way of making sure your plan doesn’t depend on getting the forecast right.

A Few Questions Worth Asking

We’d suggest a different set of questions than simply, “What will the election do to the market?”

  • Do I know which of my dollars are meant for the next five years and which are meant for the next twenty-five?
  • If markets dropped meaningfully next month, would anything I care about actually have to change?
  • Is my current plan built around my values and my timeline, or around the news?

If those answers feel clear, the election is likely a story to follow, not a reason to act. If they don’t, that’s a conversation worth having, whatever happens at the ballot box.

We’re always glad to talk through how your plan is built and whether it’s optimized for the life you’re living.

The Winter Journey: Travel, Time Together, and the Values We Pass On

Winter has a way of drawing families together. School breaks match up, the holidays gather people who are usually scattered across time zones, and for a few weeks the pace of ordinary life loosens its grip.

For many of the families we work with, winter is also travel season: a ski week in the mountains, a long stretch somewhere warm, a trip that brings three generations under one roof. These trips can be wonderful. They can also slip by as one more beautifully planned itinerary that didn’t leave much behind.

The difference usually isn’t the destination. It’s the intention behind it.

When Resources Aren’t the Constraint, Time Is

When a family has the means to go almost anywhere, the question shifts. It’s no longer, “Can we afford this?” but, “What do we want this time to mean?”

That’s a harder question, and a more important one. For families with significant wealth, the scarcest resource is rarely money. It’s undistracted time together, and especially time that connects the next generation to the values that built the family’s resources in the first place.

A winter trip is one of the few moments each year when that time is naturally available. Treating it with a bit of intention can turn a vacation into something closer to an inheritance.

Planning the Trip Around What Matters

A few ideas we’ve seen work well:

Start with the “why” before the “where.” Before booking anything, ask each member of the family what they hope to get out of the time together. Rest? Adventure? Reconnection with a sibling or grandparent? Those answers shape the trip far more usefully than a list of destinations.

Invite the next generation into the planning. Older children and young adults can own a piece of the trip: a day’s itinerary, a meal, or a budget for one part of the experience. It’s a low-stakes way to practice decision-making and tradeoffs, and it often reveals what they actually value.

Leave margin in the schedule. Some of the most meaningful moments happen in the unplanned hours, like a long dinner, a slow morning, or an unexpected conversation on a chairlift. A packed itinerary can crowd those out.

Build in something beyond yourselves. Many families include a service day, a visit to a local organization, or a conversation about how they might give together in the coming year. It doesn’t need to be formal. It just needs to be shared.

A Natural Setting for Bigger Conversations

The relaxed rhythm of a family trip can also be a good setting for conversations that are harder to start at home. Not a board meeting by the fire, but an honest, unhurried exchange about questions like:

– What do we hope this family is known for?
– What experiences or values do we most want to carry forward?
– How do we want to approach generosity, both as individuals and together?

Many families find that these conversations eventually become the foundation for a written family mission statement, a giving strategy, or an estate plan that reflects not just what will be passed on but why. The trip doesn’t have to settle anything. It only needs to open the door.

Aligning the Calendar With the Plan

It’s worth noticing how closely this connects to financial planning. A well-built plan isn’t just a set of accounts. It’s a reflection of priorities. If family time and shared experiences sit at the top of the list, it’s reasonable for the plan to make room for them deliberately, not as an afterthought.

That might mean setting aside resources specifically for family experiences, thinking through how multigenerational trips fit into a broader gifting strategy, or simply putting next winter on the calendar before this one ends. 

The Return Trip

The value of a family journey isn’t measured by the photos or the itinerary. It shows up later in a grandchild who remembers the conversation, in siblings who stay closer than they otherwise might have, or in a shared sense of what this family stands for.

This winter, wherever the trip takes you, consider bringing along one simple question: “What do we want this time to leave behind?”

When One Spouse Handles the Money

Division of labor is sensible. It’s the gap it quietly creates that’s worth closing — while both of you are around to close it.

In most of the households we work with, one person handles the money. Not by decree, usually. It just happened — one of you found it interesting, or had the time, or was better at it at twenty-six, and thirty years later that’s simply how it works. The other person has been busy with a career, or the children, or the parts of the household that are every bit as demanding and far less spreadsheet-shaped.

There’s nothing wrong with this. Specialization is how households get anything done. Nobody suggests both spouses should learn to repair the dishwasher.

But money isn’t the dishwasher. The arrangement works beautifully right up until the day it has to be carried by the person who wasn’t carrying it — and that day tends to arrive unannounced, often at the worst possible moment, and usually alongside grief or a health crisis that leaves very little capacity for learning something new.

We’ve sat across from people on that day. We’d rather have the conversation years earlier.

What the Gap Actually Looks Like

It’s rarely that the non-managing spouse doesn’t understand investing. More often it’s simpler and more practical than that. Where are the accounts. Who is the attorney. Is there a trust, and what does it actually do. Where does the money come from each month — which account, on what date, and does it arrive by itself or does somebody push a button. What happens to the pension. What happens to Social Security. Who gets called first.

These aren’t sophisticated questions. They’re logistics. But logistics are exactly what disappears when the person who held them in their head is gone, and they’re very hard to reconstruct from a filing cabinet.

The second kind of gap is subtler and matters more. It’s confidence. A spouse who has never made a financial decision alone doesn’t just lack information — they lack the experience of having made a call and watched it turn out fine. That’s the thing that can’t be handed over in a document, and it’s the reason the fix has to start well before it’s needed.

It’s also, frankly, what makes someone a target. The schemes we’ve been writing about this fall find their way to people who are newly alone, uncertain about their own judgment, and reluctant to ask. Shared fluency is a security measure as much as a planning one.

The Case for Starting Small

The instinct, when a couple decides to fix this, is to schedule a four-hour download. One spouse explains everything; the other takes notes; both of them end the afternoon exhausted and no better off, because this isn’t information that transfers in a single sitting.

What works better is smaller and more repetitive. A few ideas:

Both of you come to the meetings. Not as an observer in the corner — as a participant with questions. If one of you has been attending alone for a decade, changing that is the single highest-return thing on this list. The questions the quieter spouse asks are usually the best ones in the room, because they’re the ones nobody has stopped bothering to ask.

Put it on one page. Institutions, account types, roughly what each one is for, who to call. Not balances — those change and go stale. Structure. Then tell each other where that page lives, and write the date on it.

Let the other person drive something. A small real decision, start to finish, while the experienced spouse sits on their hands. Rebalance something. Handle the annual charitable gift. Make the call to the insurance company. One completed task builds more confidence than any amount of explanation.

Name the professionals out loud. The attorney, the CPA, the advisor, the person at the bank. A name and a relationship, not a business card in a drawer. We’d much rather a surviving spouse call us because they know us than because they found us on a statement.

Talk about the “what happens when” scenarios while they’re hypothetical. What changes if one of us needs care. What the income looks like for whoever is left. These conversations are enormously easier when they’re abstract, and nearly impossible when they’re not.

On Being the Spouse Who Handles It

A word for the one who’s been carrying this, because it deserves saying plainly: handing some of it over can feel like a loss. You’re good at it. It’s been your contribution. Teaching is slower than doing, and watching someone else do it less efficiently is its own small test of patience.

But the most generous version of managing your family’s money is managing it so that it doesn’t require you. That’s not a diminishment of the work — it’s the completion of it. The same way the best business owners build something that runs without them, and the best parents raise children who don’t need calling every week.

And there’s a quieter benefit. Couples who talk about money regularly tend to argue about it less, not more. The conversations that go badly are almost always the ones that got postponed.

Where to Start This Month

If you read all of that and want one thing to do, make it this: both of you come to the next meeting, and let the spouse who usually doesn’t ask the questions ask them. We’ll take it from there, at whatever pace suits you. There’s no quiz, and there’s no wrong question — we’ve heard all of them, and the ones people apologize for asking are usually the ones most worth asking.

If you’d like help putting the one-page summary together, that’s something we do all the time. Just say the word.

Episode 77: The John Muir Trail, Leadership, and Running Toward Adventure with Alex Potts

What happens when you stop running away from the pressures of life and start running toward the life you actually want?

Alex Potts grew up in Sunnyvale, California, riding BMX bikes through the apricot orchards that would eventually become the heart of Silicon Valley. Raised by a single mom who taught elementary school and worked hard to keep their family afloat, Alex learned early lessons about money, service, resilience, and taking care of other people.

Those lessons followed him into a remarkable career.

Alex spent more than three decades helping build what became Loring Ward, a firm that helped pioneer the fee-based model used by independent financial advisors today. Along the way, he discovered that the most meaningful work wasn’t simply about accumulating assets. It was about helping people solve problems that actually mattered.

Then, while still in his 50s, Alex stepped away from the top job.

And that’s where another chapter of his story really began.

In this episode of On Adventure, Alex and I talk about business, family, friendship, endurance, and the pull of wild places. We explore why running became an outlet during one of the most stressful periods of his life, how the John Muir Trail helped reshape his relationship with adventure, and why some of his strongest friendships have been forged while doing difficult things outdoors.

We also get into a frightening day in the Grand Canyon when Alex—despite being in some of the best shape of his life—learned just how quickly an adventure can turn dangerous.

A mile and a half from the top, in extreme heat, his body started shutting down.

What helped turn things around?

A total stranger and a bag of beef jerky.

This conversation is ultimately about much more than hiking or business. It’s about service, wisdom, community, and getting busy living while you still have the opportunity.

In This Episode

We talk about:

  • From Silicon Valley to financial industry leadership — Alex’s upbringing in Sunnyvale, the influence of his parents, and his three-decade journey helping build Loring Ward.
  • Building a life around service — Why Alex believes great businesses, advisors, and leaders put helping people ahead of products, assets, or “wallet share.”
  • Running away vs. running toward — How running initially became an escape from the pressures of work and family before adventure evolved into something Alex intentionally pursued.
  • Adventure, friendship, and community — From the John Muir Trail and Mount Whitney to the Excellent Adventure group, Alex explains why difficult experiences shared with others create unusually strong friendships.
  • Knowing your limits—and having each other’s backs — What a dangerous Grand Canyon rim-to-rim hike taught Alex about preparation, humility, listening to his body, and the unexpected kindness of strangers.

Episode Timestamps

Episode Timestamps

00:00 – From Silicon Valley Roots to Loring Ward
Alex’s childhood in Sunnyvale, being raised by a single mom, and the unlikely path that led him into financial services and eventually to building Loring Ward.

08:00 – Building a Business Around Service, Not Sales
Why Alex rejected the traditional asset-gathering mentality and built a culture centered on genuinely helping advisors and their clients solve meaningful problems.

18:00 – Where the Drive to Help Others Comes From
Alex reflects on his mother, his father’s recovery from addiction, and how both shaped his belief in service, compassion, and taking care of people.

21:00 – The Day Running Changed His Life
Overwhelmed by a demanding career, young children, and little sleep, Alex started running—and discovered the value of exercise, solitude, and uninterrupted thinking.

24:00 – The John Muir Trail and Finding Sanctuary Outdoors
Backpacking through Yosemite and the Sierra Nevada, encountering ancient forests, and discovering the peace and perspective that come from extended time in wild places.

31:00 – Running Away vs. Running Toward Adventure
How Alex’s relationship with the outdoors evolved from a coping mechanism and escape into an intentional pursuit of adventure, challenge, and joy.

33:00 – Why the Best Adventures Are Shared
From Mount Whitney to the Excellent Adventure group, Alex and Josh explore friendship, companionship, and why doing hard things together creates such powerful bonds.

41:00 – Knowing When to Push—and When to Stop
Why fitness isn’t enough in the backcountry, how experience builds wisdom, and the importance of checking your ego when conditions or your body tell you something isn’t right.

43:00 – Grand Canyon Survival, Beef Jerky & Trail Magic
A rim-to-rim Grand Canyon hike in 110-degree heat goes sideways, a stranger’s bag of beef jerky helps Alex recover, and the experience becomes a powerful lesson in humility and having each other’s backs.

A Few Takeaways

Adventure can change from escape to pursuit.
At one point, running and the outdoors gave Alex a way to cope with stress. Eventually, something shifted. Instead of running away from something, he began running toward experiences he genuinely wanted.

Fitness and wisdom aren’t the same thing.
Being capable of pushing harder doesn’t always mean you should. Experience teaches us to recognize the signals our bodies—and sometimes our lives—are sending.

The best adventures are often about the people beside you.
The summit matters. The trail matters. But years later, it’s often the people who struggled, laughed, helped, and celebrated alongside us that we remember most.

Service is a way of being.
Whether you’re helping a client navigate a family crisis, staying at the back of a hiking group to make sure everyone gets home, or opening a door for someone at the grocery store, the principle is the same: I’ve got your back.

Resources & References Mentioned

  • John Muir Trail — The roughly 200+ mile Sierra Nevada trail Alex has backpacked in sections

  • Yosemite National Park — One of Alex’s favorite places on the planet

  • Pacific Crest Trail (PCT) — Alex discusses encountering thru-hikers while on the JMT

  • Henry Cowell Redwoods State Park — Near Alex’s home in the Santa Cruz Mountains and home to magnificent old-growth redwoods

  • Undaunted Courage by Stephen E. Ambrose — Alex’s recommended account of the Lewis and Clark expedition

  • Arthur Brooks — Referenced during the discussion of “deal friends” versus “real friends”

  • Dimensional Fund Advisors — An important part of Alex’s professional story and later his son’s career

Final Thought

One of the most memorable ideas in this conversation is also one of the simplest.

When you’re on a trail and someone is struggling, you help.

You don’t ask whether they’re part of your group. You don’t calculate what’s in it for you. You recognize that today it’s them—and tomorrow it could be you.

Alex has carried that philosophy from his childhood into business, from business onto the trail, and from the trail back into everyday life.

Maybe that’s part of what adventure is here to teach us.

Take care of the people around you. Know when to push and when to turn around. Find places where the voices go quiet. And don’t spend your whole life running away from something.

Find something worth running toward.

Keep the Adventure Going

If this conversation resonated with you, share it with someone you’d want beside you on the trail.

Subscribe to On Adventure wherever you listen to podcasts, and check out The Money Trail Guide for practical ideas to help you plan for adventure, minimize “trail waste” along the way, and use your resources to move toward the life that matters most to you.

Because someday isn’t the goal.

The adventure is happening now.

Check out this episode!

Stewarding Significant Wealth: Navigating Complex Financial Decisions

At a certain point, the financial conversation shifts.

For most people, the early stages of building wealth are focused on accumulation. Growing a business, investing consistently, and creating a sense of security. But when wealth reaches a level of real significance, the questions change. It becomes less about whether you have enough and more about what you do with it, how you protect it, and whether it continues to reflect what actually matters to you.

That is the work of stewardship. And it looks very different from standard financial planning.

The complexity is real

Ultra-high-net-worth families face a different set of decisions than most financial plans are built to address. A portfolio may span public investments, real estate, private companies, philanthropic structures, and multigenerational planning. Each layer adds another decision point. Taxes matter more. The structure of asset holdings matters more. Family dynamics matter more.

And here is something that surprises many people: the margin for costly mistakes does not shrink just because there is more money on paper. In some ways, it grows. Complex wealth requires more coordination, more intentionality, and a plan that is built around your specific situation, not a template.

Tax planning is not an afterthought

For families managing significant wealth, tax planning is often where the most valuable work happens. Not because every decision should be made to save taxes, but because the tax consequences of major decisions deserve to be considered before they are made, not after.

The most effective planning weaves together investment strategy, estate considerations, charitable giving, and liquidity needs. When those pieces are coordinated, families can be much more deliberate about timing, ownership structures, and how different assets fit into the larger picture.

Beyond a traditional portfolio

Many families at this level begin exploring opportunities outside of a standard investment portfolio. Real estate, private companies, alternative investments, and family-office-style structures can all offer meaningful diversification and long-term potential. But they also entail greater complexity, more due diligence, and a need for clarity about how each piece fits the overall plan.

The question worth asking is not just “What is the return on this?” It’s “How does this serve the life and legacy we are building?”

Using wealth well, right now

One of the most common patterns we see is this: families who have worked hard to build significant wealth end up waiting too long to use that wealth intentionally. There is always a reason to hold off. Another milestone to hit. Another uncertainty to resolve first.

But wealth is most powerful when it is engaged with intention now. That might mean funding the experiences that matter most to your family. Supporting causes that align with your values. Helping the next generation understand both the opportunity and the responsibility that comes with what they will inherit. Sometimes it simply means giving yourself permission to live fully into the life your planning has made possible.

Good stewardship is not about being cautious to the point of paralysis. It is about making decisions that are values-aligned, tax-aware, and built to last, while also actually living.

The real work

At the highest levels of wealth, financial planning is not primarily about performance. It is about making sure the decisions you make today reflect who you are and what you want your wealth to do.

That requires a plan that accounts for complexity, a team that understands the landscape, and the clarity to know what you are building toward. Not just financially, but in life.

Wealth creates opportunity, but it also creates responsibility. If your financial picture has grown more complex and your planning has not kept pace, it may be time to revisit whether your strategy truly reflects the life you’re building. Reach out to our team to start the conversation.

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden

ON ADVENTURE PODCAST  |  EPISODE 69

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden

 

   

   

Episode Description

What would it take to walk 10,000 miles in a single calendar year? Not across a lifetime. Not spread over a decade. One year.

Madison Blagden is a long-distance hiker and content creator from Massachusetts who went from a pre-med student with zero backpacking experience to one of the most prolific endurance hikers in the country. After completing the full PCT (2022), the Eastern Continental Trail from Key West to Newfoundland (2023), and the Continental Divide Trail (2024), she did all three Triple Crown trails back to back in 2025, border to border, logging over 10,000 miles in a single calendar year. She documented every step herself through daily YouTube videos, Instagram shorts, and blog posts, all edited on the road.

Starting in the Florida Keys in January, she pushed through Hurricane Helene damage on the AT, Sierra snowpack, desert heat, a debilitating hip injury in the White Mountains, and a flash flood that hit her tent in the middle of the night in the desert. The miles are extraordinary. But this conversation goes deeper than the miles.

We talk about what happens between the ears when the body wants to quit, the difference between healthy internal ambition and ego-driven achievement, how the most meaningful finish lines are the ones where nobody is waiting for you, what a flash flood teaches you about calm under pressure, the spiritual dimension of pushing past absolute exhaustion, and why you will never be 100 percent ready, and that is not a reason to wait.

 

Episode Highlights

•       00:00  Introduction: Walking 10,000 miles in one calendar year

•       02:00  Madison’s background: pre-med to PCT with no backpacking experience

•       04:00  Van life, COVID, and two years of traveling in a 19-foot RV

•       09:00  Comparing the AT, PCT, and CDT: terrain, culture, and difficulty

•       14:00  Hurricane Helene’s impact on the Appalachian Trail and trail recovery

•       19:00  Planning a 10,000-mile year: budget, timing, and keeping it flexible

•       24:00  How a 5,600-mile year sparked the idea to go even further

•       31:00  Funding the hike through daily content creation on the road

•       34:00  Healthy ambition vs. ego-driven achievement

•       39:00  Internal motivation: the David Goggins voice and the gentle encouragement

•       42:00  37 miles a day for nine weeks: the math behind finishing the CDT before snow

•       48:00  Hip injury in the White Mountains and the lesson in letting go

•       51:00  Flash flood survival and what it reveals about fight-or-flight

•       57:00  Nervous system training and calm under pressure

•       01:02:00  Surrendering control: giving it up to the trail and the universe

•       01:05:00  Spiritual experiences that emerge only at the edge of physical exhaustion

•       01:10:00  Coming off trail softer: how big accomplishments quiet the ego

•       01:15:00  Closing encouragement: you will never be 100 percent ready, so go

•       01:20:00  The expanding ceiling of human limits and what comes next for Madison

 

Connect with Madison Blagden

Instagram & YouTube: @madisonblagden

Website: madisonblagden.com

Substack: substack.com/@madisonblagden

The Trek: thetrek.co/author/madison-blagden

 

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

•       Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

•       Follow on Instagram for short-form clips and behind-the-scenes content

•       Connect on Facebook: On Adventure Podcast with Josh Self

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•       If this episode resonated with you, leave a review and share it with someone who needs to hear it

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Episode 66: The Adventure Within – Finding Strength, Meaning, and Hope through Adversity with Hilal Kanaan

In today’s episode, I sit down with Dr. Hilal Kanaan – neurosurgeon, son of Palestinian immigrants, and someone whose daily work places him in the quiet but profound landscapes of human suffering, endurance, and compassion. While he isn’t chasing adventure in the traditional sense, Hilal spends his days navigating a different kind of wilderness: the emotional and spiritual terrain of walking with people through their hardest moments.

We explore the kind of toughness that’s forged not on trails or mountaintops, but in operating rooms, hospital corridors, and the inner worlds shaped by personal history, faith, and humility. Hilal shares what it was like growing up between cultures, how his parents’ story of resilience shaped him, and what strength has come to mean inside a profession where asking for help can be the bravest move of all. This conversation broadened my understanding of what “adventure” can truly mean – and I think it’ll do the same for you.

⏱️ Episode Timeline Highlights

[00:00] Opening the conversation with Dr. Kanaan and framing a different kind of adventure.
[02:00] Growing up in Kalamazoo as the son of Palestinian immigrants.
[04:00] The mix of chaos, tragedy, resilience, and optimism woven into Palestinian identity.
[07:00] Balancing two cultures and the intentional ways his parents raised their family in America.
[11:00] The parental tension between comfort and necessary challenge.
[15:00] Identifying “the ghosts in the nursery” – what we inherit, keep, and let go of.
[17:00] The book Hilal created for his kids to help them understand God, compassion, and curiosity.
[24:00] Faith as a language for gratitude rather than certainty.
[29:00] What it feels like to accompany patients through their darkest moments – and how their faith shapes him.
[35:00] The humbling lesson of asking for help when a case goes sideways.
[44:00] Hilal’s message to anyone facing hardship: your feelings are valid…and this is not the rest of your life.

🔗 Links & Resources

🙏 Closing Thoughts

If this episode resonated with you, it would mean so much if you’d rate, follow, and review the podcast — it truly helps others discover these conversations.

And don’t forget: we’re building more content on YouTube, including full episodes, clips, and behind-the-scenes insights.
👉 Find and subscribe to our YouTube channel to stay connected.

Until next time — stay safe, and stay On Adventure.

Check out this episode!

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.

Changes to charitable giving from OBBBA

Obviously, there were many changes to the tax code with the implementation of the One Big Beautiful Bill Act (OBBBA) earlier this summer.  No matter what your level of wealth, but especially for the ultra-high-net-worth, if you are charitably minded, you should pay attention to these changes to take full advantage of the tax code under the new bill.  Here’s what’s about to shift in charitable giving when OBBBA kicks in for the 2026 tax year, and how thoughtful donors can adapt to keep generosity impactful and tax-smart.

OBBBA was signed into law in July 2025 and includes several provisions that directly touch charitable deductions starting January 1, 2026. In short, the law changes who benefits, how much is deductible, and when timing really matters.1

What’s changing in 2026
  1. A new universal charitable deduction for non-itemizers:
    For the first time since the temporary CARES-era rules, non-itemizers will get a modest above-the-line deduction: up to $1,000 for single filers and $2,000 for married filing jointly for cash gifts to qualified charities. This creates a floor of benefit even if you don’t itemize.2
  2. A 35% cap on the tax benefit for top-bracket donors:
    This one gets wonky really quick…If you’re in the 37% marginal bracket, the value of your itemized charitable deduction will be capped at 35% beginning in 2026. Practically, a $100,000 gift produces a $35,000 income reduction instead of $37,000 under current rules. High earners should revisit multi-year giving plans with this cap in mind.3
  3. A new charitable deduction floor for individuals:
    Beginning in 2026, itemizing individuals can only deduct charitable gifts to the extent total annual giving exceeds 0.5% of their contribution base (generally AGI). Amounts below that floor aren’t deductible. The first 0.5% is basically throw-away contributions…no tax savings.  There are carryforward interactions and some relief for pre-2026 carryovers.4
  4. SALT cap dynamics can change the math of itemizing:
    OBBBA raises the state and local tax (SALT) deduction cap to $40,000 for 2025 and then increases it slightly each year through 2029 before snapping back to $10,000 in 2030. That higher cap in 2025 can push more households into itemizing for that year, which affects whether you should bunch charitable gifts into 2025 or stage them differently across 2026 and beyond.5
Strategy moves to consider now
  1. Bunch 2025 giving, then smooth 2026+:
    If you planned significant gifts in the next 12-24 months and you’re a high earner, consider accelerating into 2025 to avoid the 35% cap and the 0.5% floor that begin in 2026. Using a donor-advised fund lets you make the large, potentially pre-2026 contribution for tax purposes while pacing grants to charities over several years. This can also pair well with 2025’s higher SALT cap to maximize itemizing in one year.6
  2. For non-itemizers, plan to use the new universal deduction annually:
    Households that typically take the standard deduction should plan to give at least $1,000 ($2,000 MFJ) in cash each year to capture the new above-the-line benefit starting in 2026. Keep good receipts and ensure gifts go to qualified organizations. If your giving is sporadic, consider consolidating into a single calendar year to clear any administrative thresholds and simplify tracking.7
  3. Re-optimize appreciated asset gifting:
    Gifting highly appreciated securities still avoids capital gains tax and can be combined with a DAF to streamline execution. But because 2026 introduces a 0.5% floor for itemizers, coordinate the size and timing of appreciated stock gifts so that your total giving clears the floor and captures the full intended deduction. Large, fewer-and-farther-between gifts may be more efficient than many small ones post-2026.8
  4. Lean on QCDs for IRA owners age 70½+:
    QCDs remain a standout tool because they reduce taxable income directly rather than relying on itemized deductions, which helps regardless of floors or caps. If you’re charitably inclined and subject to RMDs, map out a multi-year QCD plan to satisfy some or all of your RMD while supporting charities.9
  5. Mind carryforwards and pre-2026 gifts:
    If you already have charitable deduction carryforwards, note that amounts carried into post-2025 years from gifts made before January 1, 2026 are not subject to the new 0.5% floor when used. Work with your advisor to prioritize using those carryforwards efficiently alongside any new giving.10
Bottom line

Generosity still works. What’s changing under OBBBA is the path to getting full tax value from your gifts. For 2025, ultra-high-net-worth families may benefit from front-loading into a DAF and harvesting appreciated positions before the new cap and floor arrive. For 2026 and beyond, standard-deduction households can finally claim a modest benefit each year, and retirees can keep leaning on QCDs to simplify taxes and amplify impact. The best plan is coordinated: tax bracket, SALT position, portfolio gains, and charitable goals aligned on a multi-year calendar.