Skybox Financial Group

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...

07/31/2026

Market volatility receives plenty of attention, especially when unsettling headlines and falling account balances arrive at the same time.
Read More on Decision making in Retirement

The Biggest Retirement Risk Isn’t the Market—It’s Making the Wrong Decisions at the Wrong Time By Scott Searles | July 31, 2026 Market volatility receives plenty of attention, especially when unsettling headlines and falling account balances arrive at the same time. For retirees and people app...

07/24/2026

Over the next two decades, economists expect tens of trillions of dollars to pass from one generation to the next in what has become known as The Great Wealth Transfer.

For many families, this transfer will represent the largest movement of wealth in their history.

Most conversations focus on how much money will be inherited.

Far fewer focus on how prepared the next generation is to receive it.

The Great Wealth Transfer Is Underway: Is Your Family Ready? By Scott Searles | July 24th, 2026 Over the next two decades, economists expect tens of trillions of dollars to pass from one generation to the next in what has become known as The Great Wealth Transfer. For many families, this transfer wi...

07/17/2026

Many people delay retirement because they are waiting for “the right time.”
They hope inflation will settle down. Interest rates will become more predictable. Markets will calm. Tax laws will stop changing.
Unfortunately, retirement has never worked that way. Every generation has retired during uncertainty.

Read more here:

Retiring Into Uncertainty: Why Flexibility May Be Your Greatest Financial Advantage by Scott Searles | July 17th, 2026 Many people delay retirement because they are waiting for “the right time.” They hope inflation will settle down. Interest rates will become more predictable. Markets will calm....

07/10/2026

Whether your wealth came from a successful business, a long career, disciplined investing, or a combination of all three, reaching financial independence is a tremendous accomplishment.

The strategies that help build wealth are often different from the strategies that help preserve it.
Read our blog post on wealth preservation strategies here:

You’ve Built the Wealth. Now It’s Time to Protect It. Wealth Preservation Strategies By Scott Searles | July 10, 2026 For decades, your financial life may have centered around one goal: building wealth. You worked hard, saved consistently, invested thoughtfully, and made sacrifices along the way...

07/04/2026

Happy Fourth of July from all of us at Skybox Financial Group!

06/26/2026

Artificial intelligence has become one of the largest investment themes of the decade.
History reminds us that revolutionary technologies often create tremendous opportunities. It also reminds us that even transformational companies can experience periods when expectations outpace reality.
Read more about the AI Investment Boom Here:

Is the AI Investment Boom Creating Opportunity or Excess? What Long-Term Investors Should Consider By Scott Searles | June 26th, 2026 Artificial intelligence has become one of the largest investment themes of the

06/19/2026

If the first half of 2026 has taught retirees anything, it is that uncertainty never fully disappears.
Read more on the lessons we've learned from 2026's volatile markets here:

What the Markets Have Taught Retirees So Far in 2026 By Scott Searles | June 19th, 2026 If the first half of 2026 has taught retirees anything, it is that uncertainty never fully disappears. Markets have navigated changing economic data, ongoing interest rate discussions, geopolitical headlines, and...

06/12/2026

For many business owners, selling a company represents the largest financial transaction of their lifetime.

Yet surprisingly, many owners spend years building a successful business and only a few weeks preparing for its sale.

Read more on planning moves to consider before selling a business:

Selling Your Business in an Uncertain Tax Environment: 5 Planning Moves to Consider Before You Sign an LOI By Scott Searles | June 12, 2026 For many business owners, selling a company represents the largest financial transaction of their lifetime. Yet surprisingly, many owners spend years building a...

06/05/2026

Some enter retirement after the loss of a spouse.
Others experience divorce later in life.
Some simply find themselves approaching retirement on their own after years of building a career, raising a family, or caring for loved ones.
Read more about retiring as a single woman below

Retirement Wasn't Supposed to Look Like This: Planning for Retirement as a Single Woman By Scott Searles | June 5, 2026 For many women, retirement does not unfold exactly as expected. Some enter retirement after the loss of a spouse. Others experience divorce later in life. Some simply find themselv...