What Could Cost You More Than You Expect in 2026

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Money PIG Podcast Episode 111 : What could cost you more than you expect in 2026

In Episode 111 of the Money PIG Podcast, host Tim Goodwin and co-host Joe Beckford talk about the “quiet costs” that can sneak up on high net worth families in 2026 — not from the market, but from missed planning, unaligned professionals, and waiting too long to act. Their core message: be intentional, not accidental with your financial decisions.

They walk through common planning opportunities people often miss, like Roth conversions, backdoor Roth contributions, Qualified Charitable Distributions (QCDs), and more strategic charitable giving using donor-advised funds and appreciated securities instead of cash. They also explain how money “leaks” out through tax drag and simple oversights — like not telling your CPA about a QCD, or creating a trust but never actually funding it.

A major theme is how costly assumptions can be. Many people expect the next year to look like the last, but Tim and Joe remind listeners that change is the only constant — especially when laws and tax rules shift. They discuss how proactive planning helps families adapt rather than react.

They also highlight the cost of waiting: procrastinating on estate documents, delaying estimated tax payments, or putting off strategic adjustments can lead to real penalties, missed opportunities, and long-term tax consequences.

To close, they encourage listeners to review one key area in 2026: the tax “types” of your money. If most of your wealth is concentrated in pre-tax accounts like 401(k)s, it may be time to intentionally build a healthier mix of Roth (tax-free), after-tax, and pre-tax assets — creating more flexibility and tax control in retirement.

Bottom line: Don’t do this alone. Coordinate your advisor, CPA, and estate attorney, keep your plan updated, and revisit your “why” so your money supports the life you actually want to live.

Resources and next steps:

Podcast: Things we do not recommend and why, Part I

Podcast: Things we do not recommend and why, Part II

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For personalized financial guidance,  schedule an intro call with our team at Goodwin Investment Advisory in Woodstock, Georgia . Our CFP® professionals can provide  advice and help you navigate how to invest your wealth and plan for your retirement. We’d love to help you live out your legacy! To learn more about the benefits and services we offer click here.

Goodwin Investment Advisory is an SEC-registered investment adviser (CRD #131193), and this episode is produced by evanced.net. This podcast is for informational purposes only and is not investment advice or a recommendation to buy or sell any financial products, securities, digital assets, or other investments. It should not be used as the basis for any financial decisions. The host and/or guests may personally hold investments mentioned in this episode. All investments involve risk, and past performance does not guarantee future results. Please consult with a qualified financial adviser, tax professional, and attorney before taking action on any information shared.

​​The following transcript of the podcast audio was software-generated, and not reviewed for accuracy. Therefore, the transcript below should not be used without verifying the validity and accuracy of its content. Please contact Goodwin Investment Advisory with any questions.

Joe Beckford Welcome to the Money Pig Podcast presented by Goodwin Investment Advisory where our mission is to lead you to financial pig peace independence and generosity I am your host Tim Goodwin Welcome back to the Money Pig Podcast I know you did not expect to hear me say that because Tim always usually says that but I have been promoted to co host as if you saw our last episode you would already know and yeah I get to do the intro now I think we are going to trade off I am going to have some demands some things are going to have to change

Tim Goodwin You want red mic only or something like that

Joe Beckford Only set the temperature hot tamale We like the cinnamon Texan that likes the spice We got to have the cinnamon

Tim Goodwin Definitely Joe we are so glad I am so glad to have you as a co host

Joe Beckford Me too And you know recently it was like a week ago I realized that I was so rich that I did not have to work for the rest of the year It did happen to be New Years Day at six o clock I am so rich I do not have to work for the rest of the year Rest of year just happened to be the last day of the year I literally had worked till five and I was telling my kids at five thirty your dad is so rich I do not have to work for the rest of the year I am off duty for six hours

Tim Goodwin Yeah yeah But speaking of the new year this episode is called what could cost you more than you expect in 2026

Joe Beckford Probably revisit this at the end of the year and be like yeah there was a lot

Tim Goodwin Constantly

Joe Beckford So what could cost you more than you expect in 2026 Tim I want to ask you a question When you zoom out and you look at patterns not predictions because everybody has a prediction everybody has an opinion right And we always do this fun thing at the beginning of the year We query the staff and we say what do you think the S and P is going to be by the end of the year

Tim Goodwin That is right We have not done that yet but we need to do that for 26

Joe Beckford Somebody out of our team of twelve or more will get pretty close but the rest of us are all way off Which is why let us look at patterns not predictions because predictions can be wildly wrong So when you look at patterns not predictions what are the quiet costs you see sneaking up on high net worth families for 2026

Tim Goodwin I think we should pay attention to the high net worth part of the question Because depending on where you are in life in terms of income and net worth I might answer differently But for a high net worth family I think what could sneak up on them and they might not realize it until the end of the year is missed planning opportunities

Joe Beckford Tell me more

Tim Goodwin You have been doing well Your income is increasing net worth is increasing you are building IRA assets equity in your home is increasing But you are missing opportunities like a Roth conversion like a backdoor Roth contribution Maybe you are later in life and you could have done a QCD which stands for qualified charitable distribution Maybe you are missing the opportunity to start giving out of a donor advised fund instead of giving cash You have a non qualified brokerage account with appreciated securities and you could be giving that So you are missing planning opportunities because you either do not have an advisor or your advisor is not truly comprehensive and strategic and is not telling you what you do not know

Joe Beckford Right which is something we really try to do There are a lot of things we could check every year but over time we get to know clients and we know where the planning opportunities are Any other ideas around what sneaks up on folks or planning opportunities I did not mention

Tim Goodwin I think it is start early and be intentional about the year Christmas sneaks up on us every year Like oh my gosh how am I going to pay for Christmas It is December 25th every year and it miraculously snuck up right So let us be intentional in January I am not talking about New Years resolutions because those fall by the wayside but it is a nice fresh view of let us be intentional this year If we have not been intentional before let us do it now

Joe Beckford Something like if you know what a Roth conversion is great If you do not do not worry about it But let us say you decide with your advisor you are going to do one this year If we make that plan early we can look for a better time to execute For example if the market drops we might call you and say hey this is a good time to do it because it could mean less tax You may not hit the perfect bottom but you have more time to execute closer to a better moment

Tim Goodwin Right

Joe Beckford Joe for families with a million or more invested where do you see people unintentionally leaking money Not through bad investments but through overlooked decisions How is money leaking out

Tim Goodwin I think this connects to the idea of being intentional We even have the pig here the Notorious PI I would say a lot of the leakage sounds like taxes If you are not intentional you are not coordinating with your CPA and figuring out estimated payments you can pay more in taxes or penalties

Joe Beckford Exactly And QCDs are one of my favorite tax strategies for high net worth people A lot of people have saved well in 401ks and have a lot of pre tax money and required minimum distributions can bite later One of our goals is to help you avoid being in the highest tax bracket of your life at the end of your life People may be giving cash anyway but if they have to take IRA distributions and they do not even need the money because they have Social Security a pension and other income then donating through a qualified charitable distribution can create real tax savings So leakage often looks like tax drag and missed tax opportunities

Tim Goodwin And a big one is not aligning your professionals You may have investments a CPA and an estate attorney but they are not working together Bring them together like a triangle a stronger team Do not let them operate in silos

Joe Beckford Exactly Here is an example If we do a QCD it does not show up clearly on the tax statement from the custodian The client has to tell the CPA so the CPA reports it correctly Otherwise the tax savings does not happen Another example If you create a trust you have to fund it You have to retitle assets into the trust If you do not then you have a trust but nothing in it It is like building a fence but putting no animals inside So if the advisor and estate attorney communicate directly this gets handled smoothly And if we realize large gains we can loop in the CPA so estimated payments stay accurate

Tim Goodwin Very cool Joe what assumptions do people carry into the new year that could cost them more than they expect especially around taxes cash flow or timing

Joe Beckford Assumptions matter because plans are built on them Bad info in means bad info out People often assume this year will be like last year and it will not The only consistency is change People also say this time is different especially during market declines But over long periods the market has historically recovered even if the path is bumpy Still you cannot assume the next year will look the same

Tim Goodwin Totally And changes in laws can make a year very different You have to be aware of how changes affect your taxes deductions tax rates and opportunities The tax code is massive Your CPA focuses on what you owe but a big portion of the code is about deductions and incentives That is where planning matters A financial advisor can help you spot opportunities and ask does this apply to me

Joe Beckford So let me ask you How does waiting to plan waiting to adjust waiting to have a hard conversation or make a decision end up costing real dollars

Tim Goodwin Waiting often feels safe but it charges interest Not just opportunity cost but emotional interest and tax interest One place I see waiting all the time is estate planning I am surprised how many people have no will or no estate documents even with adult children That is like playing Russian roulette If something happens the family can be stuck in a long expensive probate process I have seen situations where someone passed before documents were completed and it created a nightmare for the family

Joe Beckford Next time before you get on a plane pull up your estate documents and look at them

Tim Goodwin That is a great trigger I know someone who does that before big trips especially international flights They had a will but no power of attorney or healthcare directive Their documents also needed updating Names change relationships change guardians trustees executors beneficiaries need to be reviewed I even looked at mine and realized time passed faster than I thought So if you have documents update them

Joe Beckford Another big waiting issue is estimated tax payments Talk to your CPA and advisor early If you should be paying estimates and you do not you can owe penalties and interest We talked with a CPA partner and one of her biggest frustrations is clients skip estimated payments then get hit with penalties The interest rate has been as high as eight or nine percent That is a big cost

Tim Goodwin That sounds like a stupid tax

Joe Beckford It does

Tim Goodwin So if you wait it can cost real money

Joe Beckford Let us wrap with this For someone listening who has done pretty well financially what is one area they should review now in 2026 so nothing surprises them later

Tim Goodwin One thing I see a lot is people have amassed a lot of money in employer sponsored plans like a 401k or 403b They funded pre tax to save taxes and end up later in life with a huge pre tax bucket The strategic goal is to have a mix of Roth money after tax money and pre tax money so you have levers to pull in retirement It is the difference between pay now and play later versus save now and pay later

Joe Beckford That is great My challenge is revisit your why Why did you make the choices you made For example why did you fund the 401k pre tax If that bucket is now big maybe it is time to start funding the tax free bucket and direct contributions to a Roth 401k Also revisit your giving strategy If you are giving cash but you have appreciated stock in a non qualified account that has been held more than a year consider gifting appreciated securities instead

Tim Goodwin I love that That is intentional

Joe Beckford If you walk away with one thing it is be intentional rather than accidental And here are two cheat codes to make intentionality easier First do not do it alone Have an advisor a CPA an estate attorney or a trusted friend who is winning the way you want to win Second have a plan and update it often Creating a plan is huge Updating it regularly makes it even stronger

Tim Goodwin Any final words on what could cost you more than you expect in 2026

Joe Beckford No I think we have scared everybody enough

Tim Goodwin If you want to learn more about how we do retirement planning visit goodwininvestment.com On our services page we have information about retirement planning Please consider subscribing to our blog It is free Just your name and email We have thousands of subscribers now If you want to begin a conversation with us you can click schedule a call on the website

Joe Beckford We will sign off with gratitude Tim what are you grateful for

Tim Goodwin I am grateful I have a plan I get to update and I require my wife to come in once a year and we update our plan together I am grateful she wants to be involved and understand what is going on

Joe Beckford I am grateful for the culture at GIA We are a small independent firm and we expect each other to lead by example Have a plan be smart with money and live our values Be serious about money but enjoy life That raises the bar and I love being part of that

Tim Goodwin Thanks for hanging on listeners We appreciate you Have a great day

Joe Beckford Bye bye

Tim Goodwin Bye bye

Tim Goodwin Goodwin Investment Advisory is an SEC registered investment advisory CRD number 131193 This episode is produced by evance dot net This podcast is for informational purposes only and is not investment advice or a recommendation to buy or sell any financial products securities digital assets or other investments It should not be used as the basis for any financial decisions The host and guest may personally hold investments mentioned in this episode All investments involve risk and past performance does not guarantee future results Please consult with a qualified financial adviser tax professional and attorney before taking action on any information shared.

The Money PIG podcast is hosted by Reid Trego. Goodwin Investment Advisory is a Registered Investment Advisory firm regulated by the Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Goodwin Investment Advisory does not render or offer to render personalized investment or tax advice through the Money PIG podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.

For personalized financial guidance, schedule an schedule an intro call with our team at Goodwin Investment Advisory in Canton, GA . Our CFP® professionals can provide advice and help you navigate how to invest your wealth and plan for your retirement. We’d love to help you live out your legacy!

Goodwin Investment Advisory is a Registered Investment Advisory firm regulated by the Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Goodwin Investment Advisory does not render or offer to render personalized investment or tax advice through the Money PIG podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.