Jim Shagawat - AdvicePeriod Partner Advisor

One of the hardest conversations I have with clients is about concentrated stock.

They already know the issue.

The position has grown too large.
It dominates the portfolio.
The risk is real.

And yet… in many cases, clients delay taking action.

Why?

Because they feel stuck.

They know diversification makes sense.

But selling can mean a significant tax bill.

So they wait.

Add in familiarity.

Often, it’s a stock they’ve owned for years.
Sometimes it’s tied to their career or success.

Letting go isn’t easy.

So they hold it… even as it becomes a larger part of their portfolio.

It can feel like there’s no good answer.

That’s usually where the real conversation begins.

As retirement approaches, financial decisions start to become more connected.

Investment allocation affects taxes.
Taxes affect withdrawal strategy.
Withdrawal strategy affects how long assets last.

Small decisions can ripple in ways that aren’t obvious at first.

Retirement planning eventually becomes less about finding the next investment and more about designing a system where everything works together.

Income.
Taxes.
Risk.
Withdrawals.

When those pieces are coordinated well, retirement tends to feel a lot more predictable.

When someone has spent 25 or 30 years saving and investing, retirement planning starts to look different.

The question is no longer simply:
“How do I save more?”

The questions start to shift.
How do I turn these assets into reliable income?
How do I manage taxes over time?
Which accounts should I draw from first?
How does Social Security fit into the plan?

At that stage, investing becomes less about picking funds and more about coordinating decisions so everything works together.

And for many, having a clear strategy around those decisions can make retirement feel a lot more predictable and less stressful.

You hear retirement advice everywhere.

On TV.
YouTube.
Social media.

Most of it sounds reasonable.

Stay invested.
Use tax-advantaged accounts.
Don’t panic when markets fall.

And for many people, that advice works.

But much of it is written for the median household.

For context, the Federal Reserve’s Survey of Household Economics and Decision making (SHED) found that 37% of U.S. adults would not be able to cover a $400 unexpected expense using cash or its equivalent.
(Source: Economic Well-Being of U.S. Households in 2024, Federal Reserve, May 2025)

According to Fidelity’s retirement analysis, average balances in common retirement accounts are approximately:
IRA: about $138,000
401(k): about $144,000
(Source: Fidelity Investments Retirement Analysis, Q3 2025)

That’s the financial reality much of the media is addressing.

But many of the families I work with have already accumulated significant assets over decades of saving and investing before we begin working together.

At that stage, the questions start to change.

It becomes less about saving more, and more about coordinating taxes, withdrawals, risk, and income so the assets you’ve built can support the life you want for decades.

Fidelity Investments - Retirement Plans, Investing, Brokerage, Wealth Management, Financial Planning and Advice, Online Trading. Fidelity Investments is a financial services company that helps customers plan and achieve their most important financial goals. We offer a wide range of financial products and services for individuals and businesses, including trading & investing, retirement, spending & saving, and wealth m...

Many Americans now estimate they’ll need $1.46M to retire comfortably.

I was recently quoted in CNBC on this.

That number may be relevant for many households. But for a lot of the families I work with, the conversation is different.

It’s less about reaching a specific number, and more about how to coordinate income, taxes, and investments so the assets they’ve already built can support the life they want for decades.

That’s where planning tends to make the biggest difference.

The 'magic number' Americans say they need to retire comfortably is $1.46 million—how to catch up if you're behind Data from Northwestern Mutual shows that Americans say they need a bigger number to retire, and they're having trouble getting there.

Many of us have things we know we should stay on top of.

Like organizing documents during the year for tax time.

Instead, we often end up spending hours digging through everything at the last minute.

Investing can work the same way.

The challenge usually isn’t knowing what to do.
It’s keeping up with the small things along the way… reviewing the portfolio, rebalancing when markets move, investing new cash, and making sure everything stays aligned with the plan.

It’s staying organized and consistent long enough for the compounding to do its job.

And for many investors, having someone help keep those pieces coordinated along the way can make all the difference.

Healthcare costs in retirement can be one of the biggest unknowns.

I was recently quoted in CNBC on this topic. One thing I see often: people assume these costs will be steady, when in reality they can be very uneven.

You might have several low-cost years, followed by a year with significantly higher expenses.

Planning for that variability is just as important as planning for the total number.

Couples may need more than $400,000 to cover health-care costs in retirement, even with Medicare A 65-year-old couple may need about $400,000 to have a 90% chance of covering health costs over the course of retirement.

Was quoted in CNBC today on inflation and what it means for investors.

The big takeaway: small differences in inflation can have a major impact on what your money can actually buy over time.

This is something I’m actively discussing with clients right now.

Prices may rise more this year than the Fed predicts, global forecasting group says—what that means for your money Long-term investors should keep an eye on inflation, which erodes the value of your savings over time, experts say.

Think about elite athletes.

The best athletes in the world still have coaches.

Not because they don’t understand their sport, but because structure, accountability, and objective feedback help them perform at their best.

Financial decisions are similar.

Today, information and low-cost investments are everywhere. The challenge usually isn’t access to information.

The challenge is implementing a sound plan and sticking with it through market cycles and life distractions.

That’s often where good advice makes the biggest difference.

Most of the people I work with are not beginners.

They understand diversification. Many have managed their own investments for years.

Yet when we sit down together I often hear things like:
“I’ve been meaning to revisit this.”
“I’ve been thinking about making a change.”

Investing usually isn’t a knowledge problem.
It’s a behavior problem.

It’s a little like dieting. Most people know they should eat vegetables and avoid junk food.
The challenge isn’t knowing what to do.
It’s sticking with the plan long enough for it to work.

That’s often where good advice helps most.