Phillip Smith, TPCP CRPC AIF

10/16/2026

Maple trees, oak trees, dogwoods...they're doing something right now that most of us find terrifying:

Dropping everything they spent all spring and summer building.

Fall is not my favorite season, but there's something I love in this process. Before the leaves fall, trees pull the good stuff back into the trunk and roots, saved for the spring. They lets go on purpose, but no worries - nothing valuable gets left on the ground.

asks for something similar. You let go of the commute, the title, the daily work structure...and the consistent paychecks. Then comes the sorting: old 401(k)s from past jobs, maybe a house that's a little bigger than needed, and a budget built for (and around) your working years.

Letting go feels scary, until you see what it makes room for!

Is there something you're ready to let fall this season?

10/14/2026

In Oregon, your ballot is about to land in the mailbox, probably amongst a pizza coupon, a Bi-Mart catalog, and a fathrillion politically-charged (and 100% mudslinging) flyers.

Please don't let your ballot and the voter's pamphlet sit on the counter until it's covered in coffee rings.

I'll never tell you how to vote. Your ballot is yours (thank God for our freedom to choose!), and I'd rather talk about than politics at, well, just about any table, anyway.

But I will tell you this: the people we elect write the rules for your retirement. Congress decides how gets taxed and what Medicare covers. lawmakers have changed PERS rules and passed new -- and they can do it again. Tax brackets move when the people in office decide to move them.

These things are not accidental. Somebody votes, somebody doesn't. The result is that somebody wins a seat in government...and then rules get written, or changed.

Think of it as, "You get what you give." Put in little effort (vote purely along a party line or based on a photo or tagline), and don't be surprised by the results. Put in a little more effort (reading the voter's pamphlet before filling in the bubbles), and you can feel like you're making an informed decision when you vote, regardless of whether the results go your way. But sit it out? Then, my personal perspective is that you also need to be silent instead of complaining (or rejoicing) about the results.

There's some similarity in retirement planning. But with this, your "vote" is the deciding factor 100% of the time. People who stay engaged end up with a plan that fits their life. They ask questions, open the mail; they show up to the meeting. The people who avoid it all, or never look ahead, tend to eventually acknowledge the impact of indecision when it's too late to make a change.

Pick any side you like. Red, blue, purple, green, whatever - just read the pamphlet, fill our the ballot, sign it, and send it in. Election Day is November 3, and Oregon makes voting about as easy as it gets.

10/14/2026

You ran the numbers. You could retire at 60. So why does your stomach feel like you're about to jump off the high dive?

Because retiring early is scary, even when the math works.

For decades, a paycheck appears. Then one day it doesn't --> that's a big change for anyone.

Here's what helps:

Give every dollar a job. Savings, Social Security, rental income, the pension. Each one covers certain years.

Plan for a bad market year now, so the headlines don't run your life later. Do a test run: live on your retirement income for six months while you still have a paycheck.

The goal here is simple:
Swap "I hope this works" for "I know what happens next."

10/07/2026

Your first year of will try to bankrupt you. Politely, of course. One "we deserve this" or "we've put this off for too long" at a time.

First, maybe, it's the anniversary trip you've talked about for a decade or more. Then, the kitchen remodel, because now you're home all day staring at those yellow oak cabinets circa 1994. Then maybe you want that RV, which seems like a great idea until you try backing it into the driveway. And because you're caring and generous, you help a grandkid with college tuition.

It all sounds familiar to me, because these are the common things early retirees want to jump in and do. It's completely normal. But compare those expenses with the idea that most people expect to spend less once they retire. Eventually -- EVENTUALLY -- many do. But those early years often look expensive.

These spending stages are often described in three seasons:

The go-go years. Usually the first ten years or so. You're healthy, you're free, and you finally have time for everything you've been putting off. Spending often goes up here, sometimes a lot (especially if you're not used to monitoring the budget).

The slow-go years. Trips get a little shorter and a little closer to home. You might swap the European cruise for a long weekend in Sunriver. The spending tends to level off. this is the less expensive period of retirement.

The no-go years. Life gets quieter and everyday spending often drops, but health care costs can climb.

Why does all of this matter? A lot of retirement plans assume you'll spend the same amount every year until you're 95, accounting for inflation.

Real life rarely looks like that.

If your plan doesn't account for a busy start, you might hold back during the fun years out of fear. Or you might spend freely without knowing whether it's safe.

Neither one feels good in retrospect.

The best part of planning is the sense of 'giving yourself permission' to enjoy the go-go years. When you know your numbers can handle a bigger start, you can book the trip without the guilt. And when you know where the money for later is coming from, you stop asking, "can we afford this?" every time the credit card comes out.

Retirement should feel like a reward. You've worked a long time to get here!

10/05/2026

For a lot of people I meet, their 401(k) (or 403(b)) is the biggest pile of money they've ever owned. It's also likely the one with the most strings attached.

Don't get me wrong. The 401(k) is a great tool, and the company match is about the closest thing to free money you'll find. But when the employer-sponsored retirement plan is the only place you save, it can box you in right when you want the most freedom.

So, here are three reasons to spread things out.

1. Uncle Sam owns a piece of it. Most 401(k) money goes in before (pre-tax contributions). That feels great today, but every dollar you take out later gets taxed like a paycheck.
***It's not 'tax savings' it's tax deferral (as in, deferring until a later date)***

A Roth account works the other way: you pay taxes now, and the can come out tax-free later, if you meet the criteria to make a qualified distribution.

Having both contributions sources lets you choose which 'tax bucket' to pull from each year.

2. It's hard to reach before 59½. Pull money out early and you'll usually pay a 10% penalty on top of the taxes. There are a few exceptions, but they come with fine print. If you dream of retiring at 58, you'll want money you can reach without a penalty. A regular investment account or a solid savings cushion can bridge that gap.

3. Considering ? Healthcare doesn't wait for Medicare. Medicare starts at 65. Retire before that and you're paying for your own coverage, which gets expensive fast. If you have a high-deductible health plan, a Health Savings Account (HSA) can be a hidden gem. Money goes in tax-free, grows tax-free, and comes out tax-free for medical bills. That's a rare triple play.

Remember: the goal is flexibility. When your savings live in a few different places, you get to decide how much to take, from where, and when. That brings a lot more peace of mind than hoping one account can do everything. Looks like "diversification" is surfacing again.

10/02/2026

Phillip explains why stocks represent ownership in real businesses, why election outcomes have been a poor guide for investment decisions, and how to tell political noise apart from policy changes that may call for a plan review.

Election headlines can shake your retirement confidence. Learn why politics and policy differ, and how to build a plan that may hold up no matter who wins.

09/30/2026

Think about the plan you had at 35 for your life at 60. How much of it actually happened the way you pictured it? Did you even think about yourself at 60 when you were 35?

For most people I meet, the honest answer is that very little went according to the plan or vision. Kids took different paths. A job you loved went away, or maybe a side gig turned into a career. At some point, a global pandemic walked in and turned everyone's home and workplace upside down.

The only constant is change. Cliche? Maybe...it is the kind of reminder you see printed on a coffee mug. BUT - it matters a lot in .

Here's what continuously shifts once you stop working: tax laws get rewritten every few years; the market has great seasons and really rough ones; your health, your spending, and your family's needs all move and exchange places on the priority list over time. Even what you want out of a Tuesday afternoon in June at 67 may look different from what you pictured at 60.

I like to think about the tidepools on the Oregon coast (imagine that). Daily (twice each day, technically, I think) the tide rolls in and changes everything. The creatures that thrive there are built to adjust. They hold tight when the waves hit and spread out when the water calms. They replenish when the tide rolls in and then maintain when the tide is out.

A good retirement plan can work the same way. It should be built to bend, to adjust - it should be dynamic. That means checking in on it, updating it when life throws you something new, and having thought through a few options before you need them.

The people I see who feel most at ease in retirement have something in common. They continue to expect change. They try to plan for it, in one way or another.

What's one thing in your life that turned out completely different than you planned? I'd love to hear it in the comments, if you're willing to share.

09/28/2026

Quick question: when did you last check who's named on your retirement accounts?

If your answer is "probably when I got hired," you're in good company.

Here's a fact that surprises a lot of people: your will doesn't control your accounts. Your 401(k), IRA, deferred comp, and life insurance go to whoever is listed on the beneficiary form. That's the little form you filled out years ago. You were likely in a hurry, getting the task done so you could move on to the other stuff on your plate.

So, if your ex is still on there? Your ex may get it, even if your will says otherwise. And THAT makes for an awkward Thanksgiving.

Estate planning sounds like something for people with a lot of money, a lot of land, a lot of things. But, really, it's just answering three questions:

Who gets what?
Who makes decisions if you can't?
How easy will this be for your family?

I think that last one may matter the most. When a parent passes, the hardest part for most families is the confusion. Where are the accounts? Who has the passwords? What did Mom really want?

It can be a lot to handle if you've never begun the process. Here's a simple list of to-do's to get started:

1. Check your beneficiaries, on EVERY account and policy. At most, this takes one afternoon.

2. Update your will or trust after big life changes: new grandkids, a move, a divorce, or a kid who finally moved out.

3. Name someone for health and decisions. In Oregon, that means an advance directive and a power of attorney.

4. Write down where things live (where are important files stored, who is the custodian for accounts, where are ALL of the banks where you've stashed money, etc.). Keep this in one folder, and ensure one trusted person knows where it is.

Admittedly, there is little to no razzle dazzle here. Nobody's going to throw a party for an updated beneficiary form (though I'd come if invited).

It feels a lot like finally cleaning out the junk drawer: you dread it, and then afterward wonder why you waited so long to just get it done.

Your plan is the last gift you give your family. You can make it an easy one to open.

09/25/2026

You finally did the math at the kitchen table, coffee table, or maybe in your home office, and you feel reasonably sure you could retire at 61. Maybe even 60 if the stock market continues to cooperate. So why does your stomach feel like you just got a letter from the IRS?

Enter the unexpected: the **fear of retiring early** often surfaces even when the numbers look fine.

That feeling comes from the unknown. For 30+ years, a paycheck hits the bank account every two weeks like clockwork. Like, well, Oregon rain arriving in November. And then one day it stops.

You're supposed to trust that your savings, Social Security, maybe a pension, will just work.

Even when you've run your own numbers, it can feel like a big leap; of course it feels scary!

I talk with people reaching this place often. The worries sound like this:

"What if I run out of money?"
"What if the market drops the year I leave?"
"What if I get bored and reorganize [fill in the blank] for the fourth time?" (i.e. what if I have no idea what to do with my time?)

I've seen this help others, maybe it can help you:

Turn the fog into a map by turning uncertainty into a plan.

When you see where each dollar comes from, the fear gets smaller. Determine which account pays the bills in year one, and which account waits. Don't just arbitrarily start (or delay) - thoughtfully plan its timing. Be aware of how much of your income does not come from fixed income sources. Figure out how taxes fit in.

And...build a "bad year" plan before you need it. When you already know your next move in a market dip, the headlines lose their grip.

Maybe try giving yourself a "retirement income trial run" before retiring: live on your planned income for six months while you're still working. It's a practice run with a safety net.

The people I work with still care about after we build a plan, but they don't spend as much time lying awake, worrying about it.

That's the shift, from "I hope this works" to "I know what happens next." An early retirement should feel like the start of something good. You earned that.

So I'm curious, if anyone wants to share: what's the one "what if" keeping you from picking a date? Drop it in the comments or send me a message. I read every one.

09/23/2026

I'm still thinking about this shift from summer to fall, from the break back to school/back to the fall schedule.

There's a specific ...I don't know, "vibe" that's present a couple weeks after a break ends. Not the vacation blues. It's kind of the opposite. The schedule's got its shape again, and (for me) something feels ready for it.

I think maybe we undersell that feeling (OR...I am alone in feeling energized by a return to scheduled life). Rest gets all the credit for being good for us, and it absolutely is. But there's a version of feeling good that can only be found on the other side of a period of rest, once you're back inside a structure/routine and your mind recognizes familiar landscape.

Sometimes I can see that shift in clients a year or two into . The first few months are exciting, sort of an endless vacation, but then there is the disorienting part: this lack of structure has no end, unless you put an end to it. And then, from what I see, something clicks. Retirees build a new rhythm, a real one, not the one they had while working. Now this rhythm is theirs to fully own. And when they find that rhythm, they're far more energized than they were the year before they .

Everybody wants the freedom. they think brings. I don't think many people can understand the specific kind of alive that is felt once that freedom has a shape to it.