Are you a Miami entrepreneur who dreads tax season every year because it means scrambling to gather documents, facing unexpected tax bills, and wondering if you could have done something differently to reduce your burden? Maybe you're paying quarterly estimated taxes but have no idea if the amounts are correct? Or perhaps you only hear from your accountant in March when they're preparing last year's return—never receiving proactive guidance about what you should be doing NOW to minimize next year's taxes?
You've found exactly the resource you need, and I'm genuinely glad you're here.
I'm writing this comprehensive guide with one specific purpose: to meet you, introduce Whittmarsh Tax & Accounting, and earn the opportunity to show you how year-round strategic tax planning transforms your relationship with taxes from reactive panic to proactive control—eliminating surprises, maximizing deductions, and ensuring you're never leaving money on the table because planning happened too late.
We specialize in helping South Florida entrepreneurs, business owners, and high-earners in Miami, Aventura, and throughout the region move from once-a-year tax preparation to comprehensive year-round tax planning—including quarterly strategy meetings, proactive tax projections, estimated payment calculations, real-time decision guidance, and the ongoing partnership that ensures you're always making tax-optimized choices.
Now, I understand you came here seeking information about year-round tax planning. And I'm absolutely going to deliver that—you'll learn what quarterly planning actually involves, how proactive strategies differ from reactive preparation, what you should be doing each quarter to minimize taxes, and how to eliminate the stress and surprises that come with April-only tax thinking.
But here's the critical information your current accountant probably isn't sharing: the biggest tax planning opportunities occur BEFORE year-end, not after. Once December 31st passes, most strategies are locked in. Generic accountants who only engage in March are preparing returns for a year that's already over—they're reporting results, not optimizing them. By the time they're preparing your return, it's too late to implement the strategies that would have saved you tens of thousands.
Most successful South Florida entrepreneurs are overpaying their taxes by $20,000 to $100,000+ annually because their accountant operates reactively—preparing last year's return, maybe filing extensions, eventually getting it done, then disappearing until next March. Meanwhile, throughout the year, clients are making business decisions, timing income and expenses, considering major purchases, and dealing with tax questions—all without professional guidance.
The result? Missed deductions because expenses weren't properly documented. Lost opportunities because income timing wasn't optimized. Surprise tax bills because estimates weren't calculated correctly. Penalties for underpayment because no one was monitoring the situation. Strategic mistakes because business decisions were made without considering tax implications.
That's the problem we solve at Whittmarsh Tax & Accounting.
We don't just prepare tax returns once a year. We provide comprehensive year-round tax planning specifically designed for entrepreneurs and business owners who want proactive guidance, real-time decision support, and confidence that they're always making tax-optimized choices. We're available throughout the year—not just in March—because that's when tax planning actually happens.
First, I'm going to explain what year-round tax planning actually looks like—the quarterly review process, what happens during planning meetings, how proactive guidance differs from reactive preparation, and why ongoing partnership with your CPA creates dramatically better outcomes than once-a-year preparation.
Then, I'm going to walk through the specific strategies implemented throughout the year—Q1 prior-year cleanup and estimated payment setup, Q2 mid-year projections and course corrections, Q3 projection refinement and major decision planning, Q4 year-end tax reduction strategies, and the ongoing support that ensures you're never making important decisions without tax guidance.
But here's my direct ask: if you're a business owner or high-earner paying more than $50,000 annually in federal taxes, if you only hear from your accountant during tax preparation season, if you've been surprised by tax bills or penalties, if you're making business decisions without considering tax implications, or if you want strategic guidance rather than historical reporting—we need to talk immediately.
Schedule a consultation with Whittmarsh Tax & Accounting, and let's discuss how year-round tax planning would transform your tax situation from reactive stress to proactive control.
You can absolutely continue the annual scramble—gathering receipts in March, hoping you didn't miss anything important, facing unexpected bills, wondering if there was a better way. But if you're serious about tax optimization and building wealth efficiently—if you want a CPA who's your partner throughout the year, not just a service provider in March—we need to have a conversation.
Call us at (305) 790-5604 or book your year-round planning consultation here.
Before understanding year-round planning benefits, you need to understand the fundamental problems with traditional once-a-year tax preparation.
The Traditional Tax Preparation Model:
January-February:
March:
April 15th:
April 16th - December 31st:
The Fundamental Problems:
1. All Strategy Happens Too Late
By the time your accountant prepares your return (March/April), the tax year is over. You can't:
Your accountant is reporting what happened, not optimizing what could happen.
2. Estimated Payments Are Wrong (or Missing)
Without quarterly projections, estimated payments are either:
Most business owners either:
3. Tax Planning Opportunities Are Missed
Major tax-saving opportunities require proactive planning:
Without year-round guidance, these opportunities pass unrecognized.
4. Business Decisions Are Made Without Tax Input
Throughout the year, you're making decisions with significant tax implications:
Making these decisions without tax guidance costs you tens of thousands in missed optimization.
5. Documentation and Record-Keeping Happens After the Fact
Proper tax planning requires contemporaneous documentation:
When these are reconstructed in March (or never done), deductions are missed or put at risk.
6. You're Always Looking Backward, Never Forward
Traditional tax preparation is entirely retrospective. You learn what you owed for last year but get no guidance about this year. You're always one year behind.
At Whittmarsh Tax & Accounting, we reject this reactive model entirely. Our comprehensive year-round tax planning services provide ongoing partnership, quarterly strategy meetings, real-time guidance, and proactive planning that ensures you're always making tax-optimized decisions.
Year-round tax planning means ongoing relationship with your CPA throughout the entire year, not just during tax season.
The Whittmarsh Year-Round Planning Model:
Quarter 1 (January - March): Prior Year Finalization & Current Year Setup
Activities:
Key Deliverables:
Quarter 2 (April - June): Mid-Year Check-In & Course Correction
Activities:
Key Deliverables:
Quarter 3 (July - September): Projection Refinement & Major Decision Planning
Activities:
Key Deliverables:
Quarter 4 (October - December): Year-End Tax Reduction Implementation
Activities:
Key Deliverables:
Ongoing Throughout the Year:
The Key Difference:
Traditional CPA: "Here's what you owed for last year."
Year-Round Planning: "Here's what you'll owe this year, here's how we're minimizing it, here's what you need to do, and I'm available whenever questions arise."
The first quarter establishes the foundation for successful year-round planning.
Prior Year Tax Return Completion:
Unlike generic CPAs who simply email a PDF with signature pages, comprehensive Q1 process includes:
Tax Return Review Meeting:
Educational Component:
Current Year Tax Projection:
Based on prior year results and known changes, create first projection for current year:
Projection Components:
Example Projection:
Business owner with $180,000 prior year income:
Current Year Projection:
Estimated Payment Setup:
Calculate required estimated payments avoiding underpayment penalties:
Safe Harbor Rules:
Establish payment schedule with specific amounts and due dates:
Set up payment reminders and methods (IRS Direct Pay, EFTPS, vouchers).
Documentation System Implementation:
Establish systems for capturing deductions throughout the year:
Vehicle Mileage Tracking:
Business Entertainment Documentation:
Home Office Tracking:
Receipt Management:
Entity Structure Review:
Evaluate current entity structure for optimization:
At Whittmarsh Tax & Accounting, our Q1 process establishes the foundation for successful year-round planning. We don't just file your return and disappear—we set you up for success throughout the coming year.
The second quarter provides the first opportunity to compare projections against actual results and make adjustments.
Mid-Year Financial Review:
Compare Q1 actual results to projections:
Key Questions:
Example:
Projected $50,000 Q1 profit, actual was $65,000:
Updated Tax Projection:
Revise year-end projection based on actual Q1 results:
Original Projection:
After Q1 Actual:
Estimated Payment Adjustment:
If projections change substantially, adjust remaining estimated payments:
Already Paid:
Remaining Payments Needed:
Adjusted Schedule:
This prevents year-end surprise bills and underpayment penalties.
Mid-Year Strategy Session:
Review any major decisions or opportunities:
Common Q2 Topics:
Example Decision Support:
Client considering $75,000 equipment purchase:
Tax Analysis:
Documentation System Check:
Review documentation compliance:
Identify and fix any compliance gaps before they become year-end problems.
At Whittmarsh Tax & Accounting, our Q2 check-ins ensure you're on track, make necessary course corrections, and address major decisions before they're made without tax guidance.
The third quarter represents the critical planning period for year-end tax strategies.
Refined Year-End Projection:
With six months of actual results, create highly accurate year-end projection:
Data Available:
Projection Accuracy:
Q3 projections typically achieve 90%+ accuracy, allowing confident decision-making.
Example:
Business with known seasonality:
Year-End Planning Strategy Session:
This is the most important planning meeting of the year. Strategies discussed:
1. Equipment Purchase Planning:
Evaluate whether accelerated equipment purchases make sense:
Decision Framework:
2. Retirement Contribution Planning:
Maximize tax-deferred retirement savings:
Retirement Plan Options:
Strategy: Calculate maximum contribution to reduce current year taxes while building retirement wealth.
3. Income Acceleration/Deferral:
Strategic timing of income recognition:
Considerations:
Example:
Business owner with $450,000 income (above $200,000 NIIT threshold):
4. Expense Acceleration:
Prepay deductible expenses before year-end:
Commonly Accelerated:
Requirements:
5. Charitable Giving Strategy:
Maximize charitable deduction value:
Strategies:
6. Entity Structure Changes:
Implement entity changes requiring time:
Common Q3 Entity Actions:
7. Cost Segregation Studies:
For real estate investors, Q3 is ideal for commissioning cost segregation studies:
8. Real Estate Strategy:
For property owners considering sales:
At Whittmarsh Tax & Accounting, our Q3 planning sessions identify and implement strategies that save clients $20,000 to $100,000+ annually through proactive year-end tax optimization.
The fourth quarter is execution phase—implementing strategies identified in Q3.
Final Tax Projection:
Create final projection with near-perfect accuracy:
Final Projection Components:
Accuracy Target: Within 5% of actual (often within 1-2%)
Year-End Strategy Implementation Checklist:
Create comprehensive checklist ensuring all strategies are executed:
Equipment Purchases:
Retirement Contributions:
Income/Expense Timing:
Charitable Contributions:
Entity Structure:
Documentation:
Year-End Meeting:
Conduct final year-end meeting in December:
Meeting Agenda:
January 15th Estimated Payment:
Calculate and make Q4 estimated payment (due January 15):
Calculation:
Example:
Final projection shows $45,000 tax owed:
Year-End Reporting to Client:
Provide comprehensive year-end summary:
Year-End Summary Contents:
At Whittmarsh Tax & Accounting, our Q4 process ensures nothing falls through the cracks. We implement all strategies, ensure proper documentation, and set you up for smooth tax preparation when tax season arrives.
Beyond quarterly meetings, year-round planning includes ongoing access for questions and decisions.
Common Real-Time Support Scenarios:
Scenario 1: Major Equipment Purchase
Client Email: "Considering purchasing $150,000 piece of equipment. Should I buy now or wait until next year? What are the tax implications?"
Year-Round CPA Response: Immediate analysis of:
Generic April-Only CPA: Either no response (not tax season) or delayed generic response without specific analysis.
Scenario 2: Business Structure Question
Client Email: "Thinking about starting a side business. Should I create a separate LLC or run it through my existing company?"
Year-Round CPA Response: Comprehensive analysis of:
Generic April-Only CPA: No engagement until next tax season, decision made without guidance, potentially costly structure implemented.
Scenario 3: Real Estate Investment
Client Email: "Found great rental property investment. Price is $850,000. What should I know from tax perspective?"
Year-Round CPA Response: Detailed guidance on:
Generic April-Only CPA: Property purchased without guidance, suboptimal structure, missed opportunities.
Scenario 4: Income Timing
Client Email: "Large client payment of $80,000 can be received in December or January. Which is better?"
Year-Round CPA Response: Analysis based on:
Generic April-Only CPA: Decision made without guidance, potentially suboptimal timing.
The Value of Ongoing Access:
These real-time consultations throughout the year often save more than the cost of year-round planning. A single equipment purchase decision, entity structure choice, or income timing strategy can save $10,000-$50,000 in taxes—far exceeding any incremental cost of year-round service.
At Whittmarsh Tax & Accounting, our year-round planning clients have direct email and phone access for questions throughout the year. We respond quickly because we understand that tax planning happens in real-time, not just during tax season.
Let's quantify what year-round planning actually saves compared to traditional April-only preparation.
Example: $300,000 Income Business Owner
Traditional April-Only Preparation:
Services:
Results:
Tax Consequences:
Year-Round Strategic Planning:
Services:
Results:
Tax Consequences:
ROI Analysis:
Additional cost: $2,300 Tax savings: $37,500 Net benefit: $35,200 ROI: 1,530%
And this is just first year. S-Corp savings continue annually. Strategic guidance compounds over years.
Example 2: $150,000 Income Business Owner
Traditional Approach:
Year-Round Planning:
The numbers are clear: year-round planning pays for itself many times over through avoided penalties, implemented strategies, and optimized decision-making.
How much does year-round tax planning cost?
Investment varies based on complexity but typically ranges from $3,000-$8,000+ annually for comprehensive year-round planning including quarterly meetings, projections, unlimited consultation, and full tax preparation. This is incremental to basic tax preparation but the ROI is typically 5x-20x through tax savings and avoided penalties. At Whittmarsh Tax & Accounting, we customize planning packages based on your specific needs and complexity.
How is year-round planning different from basic tax preparation?
Basic tax preparation is retrospective—preparing last year's return showing what you owed. Year-round planning is prospective—projecting current year taxes, implementing strategies throughout the year, providing real-time guidance on decisions, and ensuring you're always minimizing taxes proactively rather than reporting them reactively.
Do I need to meet quarterly or can it be virtual?
We offer both in-person and virtual quarterly meetings based on your preference. Many clients prefer video meetings for convenience while some prefer in-person for certain discussions. The format matters less than the content—what's important is regular check-ins, updated projections, and strategic guidance throughout the year.
What if my income is variable and unpredictable?
Variable income makes year-round planning even more valuable, not less. We adjust projections and estimated payments quarterly based on actual results, ensuring you're not overpaying (if income comes in lower) or underpaying (if income exceeds expectations). Variable income businesses most benefit from quarterly monitoring.
Can I start year-round planning mid-year?
Yes, you can begin anytime. We'll establish where you are currently, create projections for the remainder of the year, adjust estimated payments if needed, and implement any remaining year-end strategies. Starting mid-year is better than waiting until next year.
What happens if I don't implement recommended strategies?
Year-round planning is consultative—we provide recommendations and guidance, but you make final decisions. If you choose not to implement certain strategies, that's fine. The planning relationship ensures you're making informed choices with full understanding of tax implications, whether you choose aggressive optimization or conservative approaches.
Do you handle bookkeeping or just tax planning?
We offer both. Some year-round planning clients handle their own bookkeeping while we provide tax planning and preparation. Other clients prefer comprehensive outsourced accounting where we handle monthly bookkeeping, financial reporting, tax planning, and tax preparation—everything. We customize our service level to your needs.
Will I still face tax bills even with year-round planning?
Yes, if you owe taxes you'll still pay them. Year-round planning doesn't eliminate taxes—it minimizes them through legal strategies and ensures you're paying correctly throughout the year (avoiding penalties and surprises). The goal is paying the minimum required by law, paid in the most efficient manner possible, with no unexpected bills.
How quickly do you respond to questions throughout the year?
We prioritize year-round planning clients for response time, typically responding within 24 hours to questions and often same-day. Time-sensitive decisions (equipment purchases with deadlines, deal structures being negotiated) receive immediate attention.
Can I switch from my current CPA to year-round planning?
Yes, we help clients transition from traditional CPAs regularly. We'll obtain your prior returns, understand your current situation, establish year-round planning relationship, and ensure smooth transition. Many clients wish they'd made the switch years earlier once they experience the difference.
You now understand how year-round tax planning transforms your relationship with taxes from reactive stress to proactive control. The question is: what will you do with this knowledge?
You have two clear options:
Option 1: Continue the annual scramble—no contact with your CPA for 9-10 months, scramble to gather documents in March, face unexpected tax bills or penalties, make business decisions without tax guidance, miss optimization opportunities because planning happens too late, and wonder each year if there's a better way.
Option 2: Schedule a consultation with Whittmarsh Tax & Accounting and discover how year-round planning provides quarterly strategy meetings, accurate projections, real-time decision support, year-end tax optimization, and confidence that you're always making tax-optimized choices.
The consultation is straightforward. We'll review your current situation, discuss what year-round planning would look like for you specifically, quantify potential tax savings, explain our process and pricing, and determine if the partnership makes sense.
For business owners and high earners, year-round planning isn't a luxury—it's the difference between overpaying taxes and keeping what you earn.
Book your year-round planning consultation: https://www.whittmarsh.com/pricing-how-it-works
Our Aventura office specializes in year-round tax planning for South Florida entrepreneurs and business owners. We've helped hundreds of clients transition from reactive preparation to proactive planning, saving them millions cumulatively.
We specifically target entrepreneurs and business owners who are ready to move beyond April-only tax thinking. Our ideal clients include:
We provide comprehensive year-round tax planning services including:
Our mission is transforming the CPA-client relationship from once-a-year transaction to year-round partnership that maximizes tax efficiency, eliminates surprises, and ensures you're always making informed, tax-optimized decisions.
If you're tired of reactive tax preparation and ready for proactive tax planning, we should talk.
Visit us online at www.whittmarsh.com
Whittmarsh Tax & Accounting serves entrepreneurs and business owners throughout Miami, Aventura, Fort Lauderdale, and all of South Florida. We specialize in year-round tax planning, quarterly projections, proactive strategy development, and transforming the traditional CPA relationship from reactive preparation to strategic partnership.