Skybox Financial Group

11/03/2026

Thank you to everyone that joined us at Topgolf for our event last week! We appreciate everyone that took the time to come out and hope you enjoyed Scott's presentation and learned some new tips from the Topgolf coach!

10/31/2026

Happy Halloween from the team at Skybox Financial Group!

10/16/2026

For many retirees, charitable giving isn’t simply a tax strategy.
It’s personal.
But if charitable giving is already part of your financial life, how you give can sometimes matter almost as much as how much you give.
And in 2026, the federal tax rules changed.
Read more here:

Giving to Charity in 2026? The Tax Rules Changed—Here’s What Retirees Should Know Before Year-End By Scott Searles | October 16th, 2026 For many retirees, charitable giving isn’t simply a tax strategy. It’s personal. Churches. Universities. Hospitals. Community organizations. Family foundati...

10/09/2026

Medicare Open Enrollment begins October 15 and runs through December 7, 2026.
For many retirees, the easiest choice will be to do nothing.
Your current plan worked this year, so why change it?
Because your plan may be changing even if you aren't.
Read more on what you should check before open enrollment ends.

Medicare Open Enrollment Is Almost Here: 7 Things Retirees Should Review Before They Renew Anything By Scott Searles | October 9th, 2026 Medicare Open Enrollment begins October 15 and runs through December 7, 2026. For many retirees, the easiest choice will be to do nothing. Your current plan worked...

10/02/2026

Artificial intelligence can do some remarkable things.
AI can provide financial information, but that doesn’t necessarily mean it should make your financial decisions.
Financial planning is rarely about finding one technically correct answer.
It’s about understanding which answer makes sense for you.

Read more here:

AI Can Answer Financial Questions. But Should It Build Your Financial Plan? By Scott Searles | October 2, 2026 Artificial intelligence can do some remarkable things. It can explain a Roth conversion in seconds. It can compare a traditional IRA with a Roth IRA. Or it can explain how bonds work, summa...

09/25/2026

For years, affluent families and their advisors were preparing for the possibility that the federal estate tax exemption could fall substantially.

That concern has changed.

For 2026, the federal basic exclusion amount is $15 million per individual.

For a married couple, appropriate planning and applicable rules may allow substantially more wealth to pass without federal estate tax.

So does that mean successful families can stop worrying about estate planning?

Read More on the federal estate tax exemption here:

The Estate Tax Cliff Disappeared. So Why Should Wealthy Families Keep Planning? By Scott Searles | Updated: September 25, 2026 For years, affluent families and their advisors were preparing for the possibility that the federal estate tax exemption could fall substantially. That concern has changed.....

09/18/2026

Social Security recipients will soon learn how much their benefits will increase in 2027.

We don't know the exact number yet, The Social Security Administration’s 2026 Trustees Report currently assumes a 2.7% COLA for benefits payable in 2027, but the actual increase won’t be determined until the necessary inflation data are available.
If your Social Security check goes up, will your retirement purchasing power actually improve?

Not necessarily.
Read More Here:

Your 2027 Social Security Raise Is Coming Into Focus. But Will You Actually Feel Richer? By Scott Searles | September 18th, 2026 Social Security recipients will soon learn how much their benefits will increase in 2027. The exact number isn’t known yet. Social Security’s annual Cost-of-Living Adj...

09/11/2026

December gets most of the attention when people talk about year-end tax planning.

I think September may be more valuable.

By this point in the year, you may have a reasonably good idea of your income, investment gains, retirement withdrawals, charitable giving, and other financial activity.

But unlike December, you still have time to evaluate your options.

Don’t Wait Until December: 5 Tax Decisions Retirees Should Review Before the End of 2026 By Scott Searles | September 11th, 2026 December gets most of the attention when people talk about year-end tax planning. I think September may be more valuable. By this point in the year, you may have a reaso...

09/04/2026

The Federal Reserve meets again September 16th-18th, with the possibility of rate increase
At its July meeting, the Fed kept its target range for the federal funds rate at 3.50% to 3.75%. But three members of the Federal Open Market Committee preferred an immediate quarter-point increase.

Read more on the upcoming meeting here:

Is Another Rate Hike Coming? What Retirees Should Watch at the Fed’s September Meeting By Scott Searles | September 4th, 2026 For much of the past few years, investors have been asking when interest rates would come down. Now there’s another possibility retirees need to consider: What if rates g...

08/21/2026

Exciting stories get attention.

A stock doubles, a startup becomes the next big thing, or a friend mentions an opportunity that “everyone” seems to be getting into.

Those stories are interesting because they are unusual.

A strong financial plan, by comparison, may look remarkably uneventful.

Read more on how a strong financial plan usually looks boring

The Best Financial Plans Usually Look Boring by Scott Searles | August 21st, 2026 Exciting stories get attention. A stock doubles. A startup becomes the next big thing. An investor makes a perfectly timed move just before the market changes direction. A friend mentions an opportunity that “everyon...