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10/12/2026

Should You Annuitize Your 403(b)?

If you are approaching retirement in healthcare or academia, there is a good chance you will be asked this question. Most people do not know what they are agreeing to until after they have already decided.

Amy Walls, CFP® walks through exactly how 403(b) annuitization works, why it is almost always permanent, and how to think through it alongside the other big retirement decisions landing in the same window.

We discuss:

Why not every 403(b) can be annuitized and how to find out which kind you have
Why annuitizing is usually an irreversible decision
How staying invested through a rollover or leaving the account in place compares on taxes and control
Why your health and life expectancy are part of the math
Why you can combine required minimum distributions across multiple 403(b) accounts but not with a 401(k) or IRA
How a pension lump sum decision and a 403(b) annuitization decision connect and why they are worth deciding together
What survivor benefits and spousal longevity mean for the whole picture

This is not a form to fill out on autopilot. It is a planning conversation.

🎧 Listen here:
https://thimbleberryu.simplecast.com/episodes/should-i-annuitize-my-403b-when-i-retire

10/07/2026

Most estate planning mistakes are not made by people who did not care. They are made by people who thought they were covered.

Amy Walls, CFP® walks through the first five of ten common pitfalls that delay decisions, misallocate assets, and create real conflict for surviving loved ones at the worst possible time.

We discuss:

What actually happens when someone dies without a will and why it is rarely what families assume
Why outdated documents can be just as harmful as no documents at all
How beneficiary designations can override a will and send assets to the wrong person entirely
What an unfunded trust actually is and why setting one up is not enough
Why incapacity planning matters just as much as what happens after death
What families end up facing in court when none of this is in place

This is not about how much you have. It is about making sure the people you love are not left cleaning up a mess during one of the hardest seasons of their lives.

🎧 Listen here:
https://thimbleberryfinancial.com/top-10-common-estate-planning-pitfalls-part-1/

09/28/2026

How Do I Recover the AMT Credit After Exercising ISOs?

If you exercised incentive stock options, held the shares, and got a tax bill that did not match anything you actually saw in your bank account, you probably had that nagging feeling that some credit should be out there somewhere.

It is. And recovering it takes planning, not just filing.

Amy Walls, CFP® walks through exactly how the AMT credit works, what the 2026 rule changes mean for tech professionals with ISOs, and how to avoid leaving money stranded with the IRS.

We discuss:

Why you can owe AMT on shares you never sold and never got cash from
What the bargain element is and how it creates phantom income
How the Big Beautiful Bill changed AMT thresholds in 2026 and why more people are now affected
What a qualifying disposition is and why it is the cleanest path to recovering your credit
Why a drop in stock price after exercise can leave your credit stranded for years
What multi-year ISO planning actually looks like in practice
Why your CPA and your financial planner both need to be in this conversation

The AMT bill is not the end of the story. It is the start of a credit you have to actively manage to get back.

🎧 Listen here: https://thimbleberryu.simplecast.com/episodes/how-do-i-recover-the-amt-credit-after-exercising-isos

09/19/2026

Working in tech can come with incredible opportunities, but it can also come with a lot of financial complexity.

For Rachael and Bernerd, higher income, RSUs, changing benefits, and the uncertainty of the tech industry made it hard to know what to do next. They knew they should be making decisions, but they didn’t want to make the wrong ones.

In this client story, they share how Thimbleberry Financial helped them turn that complexity into a plan, understand the opportunities available to them, and feel more confident making bigger life decisions.

What part of tech compensation or career uncertainty feels hardest to plan around?

If you’re ready to have this conversation or know someone who could use our advice, connect with me.

09/16/2026

Working in tech can come with incredible opportunities, but it can also come with a lot of financial complexity.

For Berecka and Bernerd, higher income, RSUs, changing benefits, and the uncertainty of the tech industry made it hard to know what to do next. They knew they should be making decisions, but they didn’t want to make the wrong ones.

In this client story, they share how Thimbleberry Financial helped them turn that complexity into a plan, understand the opportunities available to them, and feel more confident making bigger life decisions.

What part of tech compensation or career uncertainty feels hardest to plan around?

If you’re ready to have this conversation or know someone who could use our advice, connect with me.

09/14/2026

Do I Need a Financial Advisor If I Already Have a CPA?

If you are in healthcare or academia, you have probably wondered whether your CPA already has this covered. The answer matters more than most people realize, especially when your retirement picture is spread across multiple institutions and account types.

Amy Walls, CFP® breaks down exactly what each professional does, where the gaps show up, and what it actually looks like when both are working together.

We discuss:

The critical difference between tax preparation and tax planning
Why your CPA is looking backward while your planner should be looking forward
How the 457 plan early access advantage often goes unnoticed without a planner
What Roth conversions have to do with rollovers your CPA might not know about
How a pension lump sum vs. monthly income decision falls squarely in planning territory
Why the question is not "does my CPA do planning" but "will my CPA work with my planner"
What coordinated planning actually looks like for busy healthcare professionals

You are not paying two people to do the same job. You are building a team so that nothing falls through the cracks.

🎧 Listen here:
https://thimbleberryu.simplecast.com/episodes/do-i-need-a-financial-advisor-if-i-already-have-a-cpa

09/09/2026

ICYMI: Safeguarding Senior Finances and How to Talk to Your Parents About Money

The statistics on financial exploitation of seniors are significant. And in most cases, it could have been caught earlier if the right conversations had already been happening.

Amy Walls, CFP® walks through what financial exploitation actually looks like, how adult children can approach these conversations without creating conflict, and what seniors can do to protect themselves.

We discuss:

The warning signs of financial exploitation that are easy to miss or explain away
Why starting these conversations early matters more than most families realize
How to approach a parent from a place of care rather than control
What regular financial check ins actually look like in practice
How to organize documents, set agreements, and use technology to monitor accounts
When to bring in a financial advisor or attorney as a neutral third party
What seniors themselves can do to make sure their wishes are clearly communicated and honored

You do not have to wait for something to feel wrong. The best protection is a conversation that has already happened.

🎧 Listen here:
[https://thimbleberryfinancial.com/safeguarding-senior-finances/

08/24/2026

Should I Pay Off My Mortgage or Invest When Interest Rates Are High?

For a long time this felt like a settled question. Higher rates changed that. Now it is one of the most common conversations happening in financial planning, especially for tech professionals with RSUs, bonuses, and income that lands in chunks.

Amy Walls, CFP® breaks down how to actually make this call once, so you stop relitigating it every time money hits your account.

We discuss:

Why higher mortgage rates genuinely changed the math on this decision
What most people get wrong when they try to work this out on their own
Why your 401(k) match is not the right comparison for your mortgage
How RSUs and bonuses change this from a monthly question to a lump sum decision
Why paying off a mortgage with a windfall can make concentration risk worse
When the psychology of peace of mind outweighs the math
Why you do not have to go all or nothing and what a split strategy actually looks like

Pick a lane on purpose. Stop carrying the argument. That is what intentional financial planning looks like.

🎧 Listen here: https://thimbleberryu.simplecast.com/episodes/should-i-pay-off-my-mortgage-or-invest-when-interest-rates-are-high

08/19/2026

When life is busy, it’s easy for financial decisions to slide to the bottom of the list.

Benefit elections, estate updates, Roth conversions. They matter, but they don’t always feel urgent when work, family, and day-to-day demands take over.

The challenge is that waiting can quietly change your options. What once felt like a harmless delay can turn into fewer years for progress and bigger decisions later.

Progress doesn’t usually come from one big move. It happens between shifts. In small, intentional steps over time.

This is why having a plan, and someone to help you adjust it as life changes, matters.

Watch the video to see how staying engaged, even a little at a time, can make a meaningful difference.

08/10/2026

Can I Actually Retire? What Healthcare and Academic Medicine Professionals Need to Know

The uncertainty most people feel about retirement is not about running out of money. It is about not being able to see how everything works together.

Amy Walls, CFP® breaks down what retirement planning really looks like for professionals navigating pensions, 403(b)s, 457 plans, and Social Security — and why clarity changes everything.

We discuss:

Why retirement stress is usually a visibility problem, not a money problem
Why starting with a "magic number" is the wrong approach
How to build a retirement plan around actual life costs, not assumptions
The irreversible pension decision most people underestimate
What most people get wrong about 457 plans — and why it changes your sequence
How stress testing turns "Am I ready?" into "I am ready"
Why a retirement plan needs regular rhythm, not a one-time snapshot

Nothing may need to change financially. What often needs to change is your relationship to the information you already have.

🎧 Listen here: https://thimbleberryu.simplecast.com/episodes/when-can-i-retire-academic-healthcare-professionals

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