Skybox Financial Group

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...

05/30/2026

Read our latest blog post on Medicare IRMAA surcharges

Are You on Pace for an Unexpected Medicare IRMAA Surcharge? By Scott Searles | May 29th, 2026 Many affluent retirees are surprised to learn that Medicare premiums are not the same for everyone. If your income crosses certain thresholds, you may pay an additional surcharge called IRMAA, or the Income...

05/22/2026

Ever feel overwhelmed by financial decisions?
You’re not alone.
Sometimes the biggest risk isn’t the market—it’s trying to process too much information at once.
This article breaks it down in a simple way

The Biggest Risk to Your Retirement Plan Isn’t the Market, It's Decision Fatigue By Scott Searles | May 22nd, 2026 Too Many Choices, Not Enough Clarity We live in a time where financial information is everywhere. Markets update by the second. Headlines change by the hour. Opinions… never seem to...

05/15/2026

Did you know the 5 years before retirement might be the most important?
It’s not just about saving—it’s about making the right decisions at the right time.
If retirement is on your horizon, this is worth a read 👇

Skybox Financial Group is a registered investment adviser located in Middleburg Heights, Ohio. Skybox Financial Group may only transact business in those states in which it is registered, or qualifies for an exemption or exclusion from registration requirements. Skybox Financial Group’s web site i...

05/08/2026

If you’re thinking about retiring soon, market volatility can feel like a big obstacle.
But here’s the reality:
It’s not about finding the “perfect time” to retire—it’s about having a plan that works even when markets aren’t perfect.
This article breaks down what actually matters

Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing By Scott Searles | May 8th, 2026 The Wrong Question Most Retirees Are Asking When markets get choppy, many pre-retirees start asking the same question: “Is this a bad time to retire?” It’s a fair question—bu...

05/01/2026

Read our latest blog post on the Tax Cuts and Jobs Act extension and what if could mean for your family.

Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families by Scott Searles | May 1st, 2026 When the Deadline

04/17/2026

Thank you to everyone that attended our Painting with a Twist night! We had a great time seeing everyone and loved seeing everyone paintings!

04/17/2026

Check out our latest blog post on private equity payouts:

This website is using a security service to protect itself from online attacks. The action you just performed triggered the security solution. There are several actions that could trigger this block including submitting a certain word or phrase, a SQL command or malformed data.

04/10/2026

Read our latest blog post on what you might be missing in your taxes

What Your 2025 Tax Return Reveals About Your Retirement Plan Scott Searles | April 3rd, 2026 Most tax returns are filed, signed, and promptly forgotten. Which is unfortunate—because they often contain a preview of future financial outcomes hiding in plain sight. A Backward-Looking Document With Fo...