Ryan Landmark - Financial Planner

10/13/2026

To fall asleep, you have to first pretend to be asleep. Lie still, breathe slowly, close your eyes, even though your mind’s still going. Act like it’s already happening, and eventually it is.

I think about that a lot with money.

Nobody feels like a disciplined saver before they start saving. The automatic transfer gets set up first, usually before it feels natural, and the habit builds from there.

Most people wait for the confidence to show up before they act. Set up the plan, then see if it feels right.

It rarely works in that order.

The feeling of being “good with money” shows up after the decision. Not before it.

Cheers!

-Ryan

10/12/2026

A 30% drop on a $2,000,000 portfolio is $600,000. That's what makes "are we in a bubble" feel a lot less academic.

I get this question constantly. My honest answer: nobody actually knows, and anyone who tells you they do is guessing with confidence.

Reasons we might be:
-The top 10 companies in the S&P 500 now make up around 37-38% of the index's total weight, up from roughly 18% a decade ago, and that level now exceeds the concentration seen at the peak of the dot-com bubble in 2000.
-There's a lot of speculative enthusiasm around AI specifically, and speculative enthusiasm has preceded past bubbles.
-The S&P 500's forward P/E sits around 19, above its 25-year average of roughly 17.

Reasons we might not be:
-The companies driving this market, the largest tech names, are also some of the most profitable companies in history, not speculative startups with no earnings. Today's top 10 stocks trade around 34 times forward earnings, well below the roughly 43 times multiple the biggest stocks hit at the 2000 dot-com peak.
-Corporate earnings have grown alongside stock prices, not just the prices alone.
-"This market looks expensive" has been a common take for several years running, while the market kept climbing anyway.

Here's the more important perspective, regardless of which side you lean toward:
Nobody can reliably time when a bubble pops, including professionals who do this for a living. Trying to perfectly exit before a correction and re-enter at the bottom sounds great in theory and almost never works in practice.

What actually matters more than predicting a bubble is whether your portfolio is built for one.

Are you diversified, or concentrated in whatever's been hot? Does your allocation actually fit your timeline and risk tolerance? Could you stay invested through a drop like the $600,000 example above without panic selling?

Those questions matter more than whether we're in a bubble right now. Long-term investors don't need to correctly predict every top and bottom. They need a plan built to survive the ones they can't predict.

Cheers!

-Ryan

10/09/2026

It's Faithful Friday!

"So that you may live a life worthy of the Lord and please him in every way: bearing fruit in every good work, growing in the knowledge of God, being strengthened with all power according to his glorious might so that you may have great endurance and patience, and giving joyful thanks to the Father." (Colossians 1:10-12, NIV)

A few things in that passage stand out when you think about it through the lens of planning.

Bearing fruit. Growing. Endurance and patience. Joyful thanks.

None of that happens overnight, and none of it happens by accident either.

It's the same with your finances.

A good plan isn't a one-time event. It's something that bears fruit over years, not days. It requires patience when the market is down and discipline when it's easy to get complacent.

And it should produce something besides a bigger number. It should produce the kind of security that lets you actually give thanks instead of just chasing more.

Growth, endurance, and gratitude aren't separate goals. They work together.

The same is true with money. Build it with patience, steward it with intention, and let gratitude be part of the process instead of something you get around to after you've "made it."

Cheers!

-Ryan

10/08/2026

"I feel behind."

That's one of the most common things people say the first time we sit down together.

How you feel about your planning is arguably the most important piece of the puzzle. Not the only piece, but close to it.

Because "behind" is a feeling, not a fact. It's usually built on a comparison to someone else's highlight reel, a generic benchmark that ignores your actual life, or just not knowing where you stand, which the mind fills in with worst-case assumptions. None of those are a real measurement of your situation.

A lot of that feeling comes from disorganization more than anything else. Some money here, some money there, an old 401(k) you haven't looked at in years, no real sense of how it all fits together. When everything feels scattered, it's hard not to feel behind, even if the actual numbers are fine.

A real measurement comes from looking at your actual numbers, your actual goals, and your actual timeline, and seeing where they land.

Sometimes that confirms the feeling. You are behind where you want to be, and now you know exactly what to adjust.

Sometimes it does the opposite. You're in a far better spot than you felt, and the weight that comes off is immediate.

Either way, organizing it brings intention. And intention is where confidence comes from.

You can't fix a feeling with more anxiety about the feeling. You fix it with information.

A real plan gives you clarity, not a guarantee, just a clear picture of where you actually stand.

Knowing where you stand replaces "I feel behind" with "here's exactly where I am, and here's what to do next."

One of those is a weight on your shoulders. The other is a plan to lift it.

Cheers!

-Ryan

10/07/2026

Your advisor's paycheck is shaping the advice you get, whether you realize it or not. Not maliciously, necessarily. But every compensation model in financial planning has a built-in incentive, and none of them are conflict-free.

Flat fee planning means you pay a set amount for a plan, no matter your account size. That makes cost predictable. But I've seen it go wrong: single, mid-20s paid $3,000 for a "plan" that turned out to be a single-page PDF of recommendations, no shown analysis, never actually implemented or even how to implement it. Once the fee was paid, there was no incentive left to see it through.

Hourly pay works like a lawyer or accountant billing their time. You only pay for what you use. But I've also seen the opposite problem: a beautifully designed PowerPoint that took 30 hours to do the analysis and build, when the same information could have fit on a couple pages for what this person was looking for. More hours billed, more time padded.

AUM fees mean you pay a percentage of what's managed, regardless of how much work the advisor actually puts in on your account that year. On a $500,000 portfolio, a 1.25% fee is $6,250 whether they spend 2 hours or 20 on your planning that year. It ties their income to your portfolio growing, which is a REAL positive. It also incentivizes them to manage more assets, even when doing something else may be better for your goals.

Commissionable products mean you pay through a built-in commission on something like insurance or certain investment products. Advisors have an incentive to help people in this area of planning, which is positive. But I've seen a young person put nearly 15% of their income into an insurance policy, that certainly wasn't the right fit in their planning.

None of these are inherently good or bad. That's not the real question.

The real question is whether your advisor discloses how they're paid, explains their reasoning, and gives you great planning despite whatever conflict sits underneath their compensation.

Cheers!

-Ryan

10/06/2026

Here are the top 10 reasons people hire me for planning:

-They don't know if they're on track.
-They're nearing or in retirement and don't know how to turn savings into income.
-Their accounts are scattered across old employers and random firms.
-They don't have a real tax strategy.
-They want a second opinion on a plan they already have.
-They just went through a major life change.
-They're capable, but don't have time to manage it themselves.
-They want their family protected (insurance, beneficiaries, estate docs).
-They're not confident making big financial decisions alone.
-They want to actually enjoy their money, not just stack it.

If more than one of these sounds like you, let's talk.

Cheers!

-Ryan

10/05/2026

Growing up, you were probably taught a simple rule:

The more money in your bank account, the better.
That's not wrong.
Having money is better than not having it.

But that rule leaves something out: opportunity cost.

Opportunity cost is what you give up by choosing one option over another.

Every dollar sitting in a checking account isn't just "safe."
It's also not doing anything else.

Here's a simple example:

Say you have $50,000 sitting in a checking account earning close to nothing, call it 0.5%.
After 10 years, that grows to about $52,500.

Now say that same $50,000 was invested instead, averaging 8% a year.
After 10 years, that grows to about $108,000.

Same starting amount.
Same 10 years.
A difference of roughly $55,000.

That's the opportunity cost of "playing it safe" with money you didn't actually need to keep liquid.

To be clear, this isn't an argument against having cash.
You need an emergency fund.
You need money set aside for near-term expenses.
Cash has a job, and it's a real one.

But beyond what you actually need on hand, letting excess cash sit there isn't neutral.
It has a cost.

It's just a quiet one, because you never see the number for what it didn't become.

The real question isn't "How much money do I have?"

It's "Is my money doing the job I actually need it to do?"

Hypothetical example for illustration only. Not a projection or guarantee of future results.

Cheers!

-Ryan

10/01/2026

Here’s one of the things many business owners tend to overlook.

Business owners may be able to protect themselves from the financial consequences of losing a key employee.

10/01/2026

Steven Pressfield wrote a book called "The War of Art" about a force he calls Resistance.

His point is simple:
Resistance is what keeps people from doing the work that actually matters to them.

Not with an outright "no."

With delay.
With "I'll get to it."
With "next month makes more sense."

Pressfield describes Resistance as insidious.

It doesn't announce itself.
It sounds reasonable.
It shows up as a good excuse instead of an obvious one.

I see the financial version of this constantly.

Nobody decides, "I'm never going to plan for retirement."
They just don't start this year.

Nobody decides, "I'm fine never having a will."
They just haven't gotten around to it.

Nobody decides, "I don't want to know if I'm on track."
They just keep putting off the conversation that would tell them.

That's the danger of inaction.

It rarely feels like a decision.
It feels like nothing happened.

But five or ten years later, "nothing happened" is exactly the problem.

The accounts never got consolidated.
The beneficiaries never got updated.
The plan never got built.

Not because of one bad decision.
Because of years of reasonable-sounding delay.

Here's the thing about Resistance:

It never goes away on its own.
It just waits for the next deadline to talk you out of.

The people who end up in the best position aren't the ones who never felt resistance.
They're the ones who acted anyway.

What's the one thing you've been meaning to do with your finances that keeps getting pushed to "later"?

That's probably the thing to start with.

Cheers!

-Ryan

09/30/2026

A prospective client reached out recently to prepare for retirement.
They had never worked with an advisor before.

When I pulled everything together, here's what I found:

About 20 IRAs.
Spread across different firms.
They thought you could only contribute to each account once, so each year they contributed, they opened a new one.

No asset location strategy.

No real asset allocation strategy either.

I could keep going…

And yet, somehow, they'd still managed to accumulate a couple million dollars! (Pays to invest large sums!)

So we got to work.

We organized the accounts.
Built a pre-retirement plan.
Mapped out Social Security and pension timing.
Built a cash flow plan.
Planned around capital gains.
Fixed the asset location.
Fixed the asset allocation. Etc.

By the end, they told me how confident they finally felt about their future.

Not hopeful.
Confident.

That's a different feeling.

I asked what had kept them from working with an advisor all those years.

Their answer was simple:
They didn't want to pay fees.

After going through this process and seeing what it actually did for their plan, that mindset is one they now regret.

Not because fees don't matter.
They do.

But because the cost of no plan was far higher than the cost of a good one.

20 accounts they couldn't track.
Years without a real strategy.
Millions of dollars sitting there with no plan behind it.

That's the real price of "I'll just do it myself."

Use their hindsight as your foresight.

If you're not confident making these decisions on your own, that's not a reason to avoid planning.

It's the reason to get help.

Cheers!

-Ryan