Missy Soele, CPA

Insights & tax-planning guidance

Educational notes and tax planning strategies from Missy Soele, CPA, shared for general awareness — not individualized advice.

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June 3, 2026

Mid-year is the ideal time to review where you stand. ⚾
A quick check on your income and payments now helps avoid surprises later.

May 11, 2026

Timing is everything — especially with taxes. Second quarter estimated payments are due June 15th. Don’t get caught off base. Plan now!

Tax Insights

Tax-planning guides & strategies

In-depth, plain-language notes on the planning decisions that shape a return — written for individuals, families, and closely held business owners.

Jump To: Founder-Parents Strategy IRMAA 2026 S Corp vs Sole Prop 2026 Q2 Estimates Mid-Year Review Year-Round Strategy S-Corp Elections Gift & Estate Timing
Strategy

You’re not behind. You’re just maxed out.

That’s the honest part most people don’t say out loud.

Many parents are doing an incredible job building their businesses while raising their families — but tax planning often gets pushed to the bottom of the list. Not because they don’t care, but because it genuinely feels like one more thing when life is already full.

The real shift happens when we move from reactive mode to proactive rhythm. Small, consistent planning creates more breathing room than big last-minute efforts ever could.

As a mom building my practice while raising my son, I know how hard it is to juggle everything — and I see other parents facing the exact same challenges. The parents who protect both their businesses and their families best are the ones who treat tax strategy as a standing rhythm, not a seasonal scramble.

Mid-year is a natural pause point. It’s a good time to reflect on what small adjustments could make the second half of the year feel lighter.

Worth reflecting on as we head into the second half of the year.

Swipe through the carousel below for more:

↓ Download the PDF version

For general educational purposes only — not individualized tax advice.

Planning

Your 2026 Medicare IRMAA Roadmap: Navigating the Appeal After Semi-Retirement

Medicare Part B and Part D premiums for 2026 are based on your 2024 income. For individuals who reduced their work hours or moved into semi-retirement, this can result in higher premiums than their current situation actually justifies.

The good news is that a significant reduction in work income often qualifies as a Life-Changing Event (LCE). This allows you to file an appeal using Form SSA-44 and potentially lower or remove the IRMAA surcharge.

2026 IRMAA No-Surcharge Zone

  • Single filer: $109,000 MAGI or less
  • Married Filing Jointly: $219,000 MAGI or less

Even a small amount over the threshold triggers surcharges starting at $81.20 per month for Part B and $14.50 for Part D — and they increase in tiers.

The 5-Step SSA-44 Appeal Process

  1. Identify the qualifying Life-Changing Event (e.g., work reduction / semi-retirement)
  2. Report your recent income and tax filing status
  3. Estimate your future income if you expect it to remain lower
  4. Gather supporting evidence (employer letter, pay stubs, tax documents)
  5. Sign and submit the form to your local Social Security office

Many clients find that including a clear CPA cover letter explaining the income change strengthens the appeal.

2026 Medicare IRMAA Roadmap

For general educational purposes only — not individualized tax or Medicare advice.

Entities

S Corp or Sole Prop? Crunching the Numbers for 2026

Choosing the right tax structure can have a meaningful impact on your take-home pay and long-term planning. For many business owners, the decision between remaining a Sole Proprietor or electing S Corporation status comes down to the numbers.

The Key Difference

  • Sole Proprietorship: 100% of net profit is subject to 15.3% self-employment tax.
  • S Corporation: Only the W-2 salary portion is subject to payroll taxes. Distributions are not.

When It Usually Makes Sense

Most likely the strategy becomes worthwhile once net profit consistently exceeds $50,000–$80,000. At $150,000+ in profit, the potential payroll tax savings can approach $10,700 per year (before additional compliance costs).

Important Considerations for 2026

  • The IRS requires a “reasonable salary” — paying yourself zero salary and taking only distributions is a red flag.
  • Additional paperwork including filing federal and state reports each quarter, issuing W2s at the end of the year, and filing a separate federal tax return.
  • Health insurance premiums for >2% shareholders must be added to your W-2 (but remain deductible).
  • Texas has no state income tax, which improves the math compared to high-tax states.

The infographic below walks through the break-even analysis and key trade-offs to help you evaluate your own situation.

S Corp vs Sole Prop 2026 Break-Even Analysis

For general educational purposes only — not individualized tax advice.

Compliance

Second Quarter Estimated Taxes: Don’t Miss the June 15 Deadline

Timing matters in tax planning — especially when it comes to estimated tax payments. The second quarter 2026 estimated tax payment is due on Monday, June 15.

Why It Catches People Off Guard

For many individuals, families, and business owners, this is a key checkpoint to stay ahead of the game and avoid underpayment penalties later. Common reasons for surprises include:

  • Income from real estate, self-employment, or investments running higher than expected.
  • Withholding from W-2 wages not covering all sources of income.
  • Penalties are calculated on a quarterly basis — missing one quarter can add up.

Pause and Plan

A quick mid-year review of your year-to-date income and payments can show whether an adjustment is needed. Some clients choose to increase their quarterly payments, while others explore legitimate ways to reduce current-year taxable income before year-end.

If your situation has changed this year — new rental property, business growth, or investment income — June is an excellent time to pause and plan.

For general educational purposes only — not individualized tax advice.

Strategy

Mid-Year Tax Checkup: Why June Is the Perfect Time to Review Your Situation

Mid-year is one of the most valuable — and underused — moments in tax planning. By early June, you have a clear picture of how the year is unfolding, but you still have time to make adjustments before December 31.

Why June Matters

For many families, real estate investors, and business owners, the biggest risks at this point are underpayment penalties or missed planning windows. A quick mid-year review helps you:

  • Compare actual income and expenses against your earlier projections.
  • Check whether your estimated tax payments are on track.
  • Identify opportunities to reduce current-year taxes while they're still available.
  • Avoid unpleasant surprises when you file next spring.

Common Areas Worth Reviewing

A few proactive steps now can create smoother outcomes later. Key items to check include:

  • Estimated tax payments (federal and state)
  • Retirement contributions or HSA funding
  • Business expense timing
  • Real estate depreciation or cost segregation opportunities
  • Charitable giving strategies

A few proactive steps now can create smoother outcomes later.

For general educational purposes only — not individualized tax advice.

Planning

Why year-round strategy beats April scrambling

Most tax outcomes are decided long before a return is filed. By the time figures are entered in April, the year is closed and the opportunities that mattered have already passed.

The Core Problem

A planning-focused approach treats the return as the last step in a year-long process, not the process itself. Scrambling in spring means you miss key windows for retirement contributions, entity elections, and the precise timing of income.

The Proactive Solution

  • Quarterly Check-ins: Adjust withholding proactively to avoid underpayment penalties that surprise so many filers.
  • Income Timing: Accelerate or defer income deliberately based on your projections.
  • Strategic Control: Have fewer major financial decisions left to make by the time tax season arrives.

Foresight tends to be quieter than firefighting — and usually less costly over time.

Entities

When an S-corp election actually makes sense

The S-corporation election is one of the most frequently suggested — and most frequently misapplied — ideas in small-business tax planning.

When Does It Work?

Its potential benefit comes from reducing self-employment tax on a portion of profits, but that benefit only materializes once a few specific conditions hold true:

  • Your business profit is consistently above a reasonable salary threshold.
  • The savings justify the administrative cost of running full payroll.
  • The savings justify the cost of filing a separate corporate tax return.
  • Your specific state tax laws don't penalize S-corporations.

The Bottom Line

Below certain income levels, the added complexity can outweigh the savings entirely. The right answer depends on the numbers in front of you, the stability of those numbers, and your tolerance for additional compliance — not on enthusiasm for the structure.

A careful projection, run before the election is made, usually reveals whether the move is worthwhile or simply fashionable.

Trusts

Gift & estate timing for closely held owners

For owners of closely held businesses, land, or family entities, when a transfer happens often matters as much as whether it happens.

Key Variables in Estate Planning

Valuation, available exclusions, and the sequencing of gifts across years all influence the long-term result. Importantly, decisions made in one year constrain the options available in the next.

  • The Annual Exclusion: Utilizing yearly caps effectively before they expire.
  • Lifetime Exemption Planning: Maximizing large transfers strategically over time.
  • The §663(b) Election: Leveraging the 65-day rule for trust distribution timing.

A Coordinated Approach

Coordinating with your legal and bookkeeping teams — rather than treating the tax return as an afterthought — keeps all these moving parts aligned. None of this is one-size-fits-all; the appropriate path depends on the family's goals, the assets, and the timeline.

Thoughtful sequencing, considered early, tends to preserve more options than reactive decisions made under deadline.