About Scott Searles

Serving clients primarily in Ohio and Florida, Scott is the owner of Skybox Financial Group, where, as a knowledgeable and experienced professional, he helps clients plan for their financial future.

Retirement Wasn’t Supposed to Look Like This: Planning for Retirement as a Single Woman

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 [...]

By |2026-06-04T16:57:18-04:00June 5th, 2026|Retirement Blog, Weekly Update|Comments Off on Retirement Wasn’t Supposed to Look Like This: Planning for Retirement as a Single Woman

Are You on Pace for an Unexpected Medicare IRMAA Surcharge?

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 [...]

By |2026-05-29T15:55:34-04:00May 29th, 2026|Retirement Blog, Weekly Update|Comments Off on Are You on Pace for an Unexpected Medicare IRMAA Surcharge?

The Biggest Risk to Your Retirement Plan Isn’t the Market, It’s Decision Fatigue

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 [...]

By |2026-05-21T16:49:00-04:00May 22nd, 2026|Retirement Blog, Weekly Update|Comments Off on The Biggest Risk to Your Retirement Plan Isn’t the Market, It’s Decision Fatigue

The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact

The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact By Scott Searles  |  May 15th, 2026 There’s a common assumption that retirement planning is about [...]

By |2026-05-13T16:22:03-04:00May 15th, 2026|Retirement Blog, Weekly Update|Comments Off on The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact

Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing

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 [...]

By |2026-05-08T15:28:55-04:00May 8th, 2026|Retirement Blog, Weekly Update|Comments Off on Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing

Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families

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 Disappears, So Does the Pressure—Or [...]

By |2026-05-01T13:55:22-04:00May 1st, 2026|Retirement Blog, Weekly Update|Comments Off on Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families

Private Equity Payouts: How to Avoid a Surprise Tax Bill

Private Equity Payouts: How to Avoid a Surprise Tax Bill By Scott Searles A private equity payout often represents years of work coming together. It also tends to introduce [...]

By |2026-04-24T10:18:17-04:00April 16th, 2026|Retirement Blog, Weekly Update|Comments Off on Private Equity Payouts: How to Avoid a Surprise Tax Bill

What Your 2025 Tax Return Reveals About Your Retirement Plan

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 [...]

By |2026-04-02T16:33:31-04:00April 10th, 2026|Retirement Blog, Weekly Update|Comments Off on What Your 2025 Tax Return Reveals About Your Retirement Plan
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