Phillip Smith, TPCP CRPC AIF

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.

09/21/2026

Through the first week of the school year, my kids looked wrecked.

Not physically, but mentally. Emotions on edge at 5pm. Ready to melt down at - or fight against - anything contrary to their 'in the moment' need. Homework that should take fifteen minutes stretches to forty, not because it's hard, but because their brains are still catching up to the idea that summer's actually over.

I try to remind them how much energy it takes to reorient to scheduled learning, to adjust to a new teacher, to just, well, get back into the routine.

We've watched it happen every September, and every September I forget how challenging it is until we're all back in the midst of it.

I recognize a similar fatigue in adults heading into , just stretched out over months and years instead of days and weeks.

People assume the hard part of retiring is financial. And, yeah, sometimes it is.

But, also, a lot of the exhaustion I see in new retirees has nothing to do with . It's the same thing my kids are going through. Forty years of a known and familiar structure just ended, and their brain hasn't caught up to the fact that nobody's telling them what to do at 7am anymore.

That adjustment takes a lot of brain energy. It's not laziness, and it's not something a good financial plan fixes on its own. It's just what it costs to rebuild (or build brand new) a job you were ready to leave - and the routine that was embedded in it.

Give yourself, or your newly retired parent, or your exhausted second grader, the same grace. The tiring part is temporary. But it's very real and very 'in your face' while it's happening.

09/18/2026

If you've ever sat across from a financial advisor and left the meeting without understanding a single thing they actually said, or spent two minutes on their website and felt the overwhelming sense of déjà vu, this one's for you.

Here's a little bingo card. See how many of these you've found on a financial advisor website (or heard from their mouths). I will most assuredly be implicated here (I know our website copy needs a face lift).

"We help you navigate your financial journey with clarity and confidence." That's twelve words that could describe literally any advisor, doing literally anything, for literally anyone. It tells you nothing except that someone in marketing liked the way it sounded. It's like the lobby of a 3-star hotel: forgettable.

"Your journey to financial freedom." You don't have a journey. You have a retirement date and a list of decisions nobody's walked you through yet.

"We're a trusted partner in your financial future." So, not trusted yet, but soon? 😄 What have they actually done to earn that word, in the present?

"We take a holistic approach." Ask them what that means, specifically, for your situation. Watch what happens.

"Comprehensive, personalized, goals-based planning." Four buzz words, zero information. None of that tells you what they'd actually do differently for you than for the next person who walks in.

"Peace of mind." The most overworked promise in the industry, usually made before anyone's looked at your actual numbers. And also, not one I'm allowed to use (you definitely won't mark this one on your bingo card looking at OUR website!!).

But, here's my honest confession as of today (but hopefully not by next week): "Clarity and confidence" is on my own website right now. I'm working on it, I really am. I'd rather you know exactly what I do than read a phrase that sounds nice and means, well, basically nothing.

If your advisor's answer to "what would you actually do for me" is one of the phrases above, ask a lot of follow-up questions. A good advisor can get specific fast. If they can't, that's worth noticing.

If their answer to your question is another one of these empty and overused phrases...you can DM me here or find us on our website.

09/18/2026

A personal reflection on summer ending and school routines returning, tracing how seasons once structured daily life on their own, and what changes when retirement removes that built-in rhythm. Three prompts for a fall check-in.

Fall gives homeowners and kids a built-in schedule. Retirement doesn't. A reflection on seasons, structure, and keeping your plan from drifting.