9 min read
How to Build a Year-Round Tax Strategy (Not Just April Planning)
Chris Middleton : Oct 8, 2025 11:18:22 AM

How do you build a year-round tax strategy?
Run a quarterly cadence to plan, implement, document, and review. Utilize the CLEAR EDGE pillars to optimize entity and compensation, project taxes, track time, income, and expenses, capture credits, integrate real estate, fund retirement, and maintain audit-ready documentation. Finish Q4 with contributions, true-ups, and a complete documentation pack.
Table of Contents
If you paid more than $100,000 in taxes last year, the April scramble is costing you money, time, and sleep. You do not need more forms. You need a system.
A simple, year-round rhythm that turns the tax code into a tool you use intentionally.
At Make Taxes Fair, we anchor that rhythm to two ideas. First, your strategy runs on a quarterly cadence that you can follow without drama.
Second, the CLEAR EDGE Framework gives that cadence structure and focus, so each move fits into a bigger plan. The hero of this guide is the year-round strategy.
The CLEAR EDGE Framework is the operating system underneath it.
Friends don’t let friends overpay the government.™
The mindset shift: from filing to running a system
Most owners think taxes are about forms. High-earning owners learn that taxes are really about decisions. The forms only record what has already happened. Your decisions decide what gets recorded. That is why a year-round strategy works.
You stop reacting to a deadline and start running a process that protects profit while helping your business flourish.
Our execution mantra is simple. Plan. Implement. Document. Review.
That rhythm keeps you proactive and audit-ready. It also keeps your team aligned, as everyone knows what is coming next and who is responsible for it.
A quick primer on CLEAR EDGE
The CLEAR EDGE Framework encompasses nine pillars that impact what you pay and what you retain. We will tag them lightly throughout.
The pillars are:
- Credits
- Legal Structure
- Employees
- Accumulation of Wealth
- Retirement Planning
- Exit Planning
- Deduction Optimization
- Getting Organized
- Efficiency
You do not need to memorize them. You only need to recognize where they show up in your calendar so you can make the right move at the right time.
Your year-round tax rhythm
Think in quarters. Each quarter has a theme, a short checklist, and a small set of CLEAR EDGE pillars that are activated intentionally. The bullets stay tight.
The context before and after provides insight into why it matters and how to stage the work.
Q1: Close last year, lock your foundations
Theme: Clean books and entity fit.
CLEAR EDGE focus: Legal Structure, Getting Organized, Deduction Optimization, Employees, Retirement Planning.
Q1 is about accuracy and alignment. If your books are messy or your entity choice no longer aligns with your profit profile, every other decision becomes harder and riskier. Your goal is to make the rest of the year easier by cleaning the data, confirming the structure, and putting baseline policies in place.
- Financial cleanup. Reconcile accounts and ensure every transaction is categorized correctly. Clean data yields reliable projections, and these projections inform sound decisions. (CLEAR EDGE: Getting Organized, Efficiency)
- Entity review. Pressure test your structure. LLC taxed as S-Corp, holding company, straight LLC, or C-Corp in some instances. Confirm ownership splits and how you will support reasonable compensation. (CLEAR EDGE: Legal Structure)
- Accountable plan. Create a written reimbursement policy for business expenses paid personally, and then implement it on a monthly basis. This is often a low-effort, high-return approach. (CLEAR EDGE: Deduction Optimization)
- Benefits baseline. Confirm health plan fit, HSA eligibility, and whether a Section 105 plan makes sense based on headcount and facts. (CLEAR EDGE: Employees, Deduction Optimization)
- Retirement plan path. Decide now if you will run a Solo 401(k), a group 401(k) with profit sharing, or a cash balance plan. Early decisions create larger, cleaner deductions. (CLEAR EDGE: Retirement Planning)
By the end of Q1, you should have accurate books, a confirmed entity choice, a live accountable plan, and a retirement plan direction.
That foundation sets the table for bigger wins later in the year.
Q2: Map the money, model your tax
Theme: Forecast and mid-year moves.
CLEAR EDGE focus: Credit Optimization, Deduction Optimization, Accumulation of Wealth, Efficiency.
Q2 is about visibility. Clean books turn into forward-looking insight. You stop guessing and start projecting.
With a projection in hand, you can time purchases, set payroll, target credits, and plan contributions while there is still runway left in the year.
- Projection meeting. Build a 12-month profit forecast with a draft tax projection. Reflect seasonality, booked contracts, and pipeline. Update your estimated payment plan. (CLEAR EDGE: Efficiency, Getting Organized)
- Comp planning. Align S-Corp wages, owner draws, and distributions with your plan. Reasonable compensation should be defensible, not convenient. (CLEAR EDGE: Legal Structure)
- Capex plan. List equipment or vehicle purchases. Sequence by cash impact and deduction value, including Section 179 and bonus depreciation as appropriate. (CLEAR EDGE: Deduction Optimization)
- Real estate integration. If you own or plan to buy property used in the business, evaluate the cost segregation and lease structure between you and your company. This is where tax meets wealth building. (CLEAR EDGE: Accumulation of Wealth, Deduction Optimization)
- Credit scan. Screen for R&D, WOTC, and clean energy credits, such as 45L and 179D. Credits reduce tax dollar for dollar when you qualify, but they require evidence, not hope. (CLEAR EDGE: Credit Optimization)
By the end of Q2, you should know where you are headed, which levers matter most, and how you will document them.
You will not use every lever. You will choose the ones that fit your facts.
Q3: Optimize operations and timing
Theme: Turn strategy into muscle memory.
CLEAR EDGE focus: Deduction Optimization, Employees, Getting Organized, Accumulation of Wealth, Exit Planning.
Q3 is where process discipline pays off. You refine how money moves through the business and tune the timing.
Small operational improvements, run every month, create considerable cumulative savings and cleaner support.
- Expense timing. Shift controllable expenses across quarter or year-end lines if it improves brackets or smooths your effective rate. Pair this with your Q2 projection. (CLEAR EDGE: Efficiency, Deduction Optimization)
- Accountable plan audit. Verify that reimbursements are processed monthly with receipts, mileage logs, and brief notes. A written policy without execution is exposed. (CLEAR EDGE: Getting Organized)
- Family payroll. If appropriate, consider employing family members for honest work at market rates, with clear job descriptions and accurate time records. Handle payroll correctly and bank the benefit. (CLEAR EDGE: Employees, Accumulation of Wealth)
- State strategy. For multi-state operators, confirm where you have nexus, how you apportion income, and whether a pass-through entity tax election helps with the SALT cap. (CLEAR EDGE: Getting Organized, Efficiency)
- QSBS and equity tracking. Suppose you run a C-Corp or hold startup equity, track basis and holding periods now. You cannot recreate history later. (CLEAR EDGE: Exit Planning, Accumulation of Wealth)
By the end of Q3, your machine should be running smoothly.
Reimbursements should be automatic, payroll aligned, and state filings on track.
You are converting strategy into a habit.
Q4: Finish strong and lock the proof
Theme: Final moves and audit readiness.
CLEAR EDGE focus: Retirement Planning, Exit Planning, Getting Organized, Deduction Optimization.
Q4 is where you harvest. You finalize contributions, make last adjustments, and ensure your proof is airtight.
Documentation is not busywork. It is what allows you to keep what you have legally earned.
- Charitable planning. If you plan to give, consider a donor-advised fund to bunch deductions while you grant over time. (CLEAR EDGE: Deduction Optimization)
- Retirement funding. Max, the plan you chose. For cash balance plans, coordinate with your actuary early so funding is accurate and timely. (CLEAR EDGE: Retirement Planning)
- Depreciation decisions. Choose between Section 179 and bonus depreciation based on profits, carryovers, and state rules. Do the math, then decide. (CLEAR EDGE: Deduction Optimization)
- Owner comp true-up. Adjust wages and distributions to align with your reasonable compensation model. Close the loop before year-end. (CLEAR EDGE: Legal Structure)
- Documentation pack. Assemble a digital folder with minutes, written policies, logs, invoices, valuations, and calculations for every material move. (CLEAR EDGE: Getting Organized)
By the end of Q4, your cash for estimates should be set, contributions posted, and your documentation pack complete.
April becomes a recap, not a rescue mission.
The nine levers that actually move the needle
You do not need a thousand tactics. You need a short list that reliably creates savings and keeps you clean with the rules.
Here they are, mapped to CLEAR EDGE for quick reference.
- Entity optimization. The proper structure and ownership mix affect self-employment tax, QBI, benefits, and how you pay yourself. Recheck annually or after significant changes. (CLEAR EDGE: Legal Structure)
- Reasonable compensation. If you are an S-Corp owner, salary is both a tax and an audit exposure. Support it with duties, time, and market data, then run payroll consistently. (CLEAR EDGE: Legal Structure)
- Retirement design. Solo 401(k), group 401(k) with profit sharing, or a cash balance plan can shield large amounts. Early design widens your options. (CLEAR EDGE: Retirement Planning)
- Accountable plan and fringe benefits. Reimburse what the business should bear. Layer HSAs, Section 105, and education benefits where they fit. Small processes, significant outcomes. (CLEAR EDGE: Deduction Optimization, Employees)
- Real estate integration. Home office, Augusta rule, cost segregation, and arm’s-length leases between you and your company. Keep fair market values and documented terms. (CLEAR EDGE: Accumulation of Wealth, Deduction Optimization)
- Tax credits. Credits reduce tax dollar for dollar. Start documentation early and call specialists when the dollars justify it. (CLEAR EDGE: Credit Optimization)
- Timing income and expenses. You cannot control everything, but you can influence enough to smooth your effective rate. Pair timing moves with projections. (CLEAR EDGE: Efficiency)
- Multi-state strategy. Get nexus right. Use apportionment that reflects reality. Consider pass-through entity tax elections where helpful. Build a compliance rhythm. (CLEAR EDGE: Getting Organized, Efficiency)
- Audit-ready documentation. Short memos, clean logs, and centralized files are the way to go. If you cannot prove it, you often cannot keep it. (CLEAR EDGE: Getting Organized)
The Make Taxes Fair operating rhythm: Plan, Implement, Document, Review
This is how we turn ideas into results. It is simple on purpose.
Plan
Set a target effective tax rate and a savings goal that supports your growth plan. Identify which levers fit your model this year.
Put four strategy meetings on the calendar. Assign ownership for each task to prevent work from stalling.
Implement
Turn each lever into a short standard operating procedure. Automate mileage and receipt capture. Schedule payroll reviews.
Create recurring calendar reminders. Good implementation is boring, which is why it works.
Document
Keep a living Tax Strategy Binder in the cloud with tabs for entity, payroll, retirement, credits, real estate, and memos.
Store board or manager minutes for material decisions. Save the spreadsheets that show your calculations. Documentation connects your story to your proof.
Review.
Track four numbers on a small dashboard. Year-to-date profit, projected tax, estimated payments made, and effective tax rate.
After each quarter, update the projection and adjust contributions, purchases, or timing.
After year-end, compare planned savings to actual savings and capture lessons learned.
Your tax strategy squad
High-earning owners win with a small, coordinated team. The key is communication. Ask your team to speak directly to each other and share the same plan and calendar.
- Tax strategist or strategic CPA. Orchestrates the plan, runs projections, and keeps you on track.
- Controller or bookkeeper. Protects data quality and ensures documentation flows into your binder.
- Payroll partner. Handles reasonable compensation, fringe, and elections correctly.
- Specialists on call. Cost segregation engineer, retirement actuary, tax attorney, and state tax pros when the dollars justify the depth.
Keep your compliance CPA in the mix.
Strategy and compliance are complementary roles that protect you and unlock savings.
Metrics that matter
What you measure is what you manage. Keep it simple.
- Effective tax rate. Total tax divided by total income. Track quarterly to spot drift early.
- Projected strategy savings. The year-to-date savings are tied to specific levers, not just deferrals.
- Cash on hand for taxes. Hold at least one quarter’s estimated payment in reserve.
- Audit-readiness score. A green, yellow, red checklist across your binder tabs.
If your effective rate creeps up, decide which lever to pull next. If your readiness score slips, assign a cleanup sprint. The numbers will point you to the next best move.
A 30-day launch plan, mapped to CLEAR EDGE
You do not need perfection to begin. You need momentum.
Week 1
Schedule four quarterly tax strategy meetings and build your Tax Strategy Binder with clear folders. Assign owners for each tab. (CLEAR EDGE: Getting Organized)
Week 2
Reconcile last quarter’s books and lock categories. Draft your accountable plan and start running reimbursements this month. (CLEAR EDGE: Deduction Optimization, Efficiency)
Week 3
Run a projection session with your strategist or CPA. Identify the three levers that fit your facts this year. (CLEAR EDGE: Efficiency)
Week 4
Implement one lever completely. Increase 401(k) deferrals, open an HSA if eligible, or execute a market-rate lease between you and your company with proper support. (CLEAR EDGE: Retirement Planning, Deduction Optimization, Accumulation of Wealth)
Wins stack. Confidence grows. Your system takes shape.
Guardrails that keep you safe
Rules protect results. Stay within these lines so your savings are durable and your sleep is solid.
- Substance over form. Every move needs a real business purpose and real economics.
- Market values. Use fair rates for rent, comp, and related-party services. Note your source.
- Logs and receipts. No log often means no deduction.
- Consistency. A written policy is only as strong as the monthly execution behind it.
- Ethics. We use the rules as written. If your facts do not support a move, we do not use it.
When to get help
Bring in a strategist when complexity or dollars cross specific lines.
Suppose you will pay more than $100,000 in total taxes this year, operate in more than one state, add a second location, introduce equity for partners, or buy commercial real estate.
In that case, you will benefit from proactive planning and coordinated specialists.
We built Make Taxes Fair to provide owners like you with a clear, plain-language strategy, practical execution, and a team that works well together.
The result is a year-round system that protects profit and helps your business flourish.
A real tax strategy is not about April. It is about a calendar, a checklist, and a handful of powerful levers that you run with discipline.
Pair that year-round rhythm with the CLEAR EDGE Framework, and your paperwork starts telling a different story, one of preparation, proof, and predictable savings.
Ready to start a conversation? Reach out and let us know, and remember… Friends don’t let friends overpay the government.™.
Article FAQs
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What is a year-round tax strategy?
It is a quarterly rhythm of planning, implementation, documentation, and review. You make moves while there is still time to act. You keep audit-ready proof. Over time, the rhythm reduces stress and produces predictable savings.
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How often should I meet with my tax team?
Once per quarter for strategy, with quick touchpoints before estimated payment due dates, add a project meeting anytime you make a significant change, such as a new location, a large purchase, or a real estate deal.
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Do I need an S-Corp to save on taxes?
Maybe. An S-Corp can reduce self-employment tax when supported by a defensible, reasonable compensation analysis. It may not be suitable for everyone or in every state. Review the decision annually as profits and goals evolve.
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My income is volatile. Can a plan still help?
Yes. Volatility increases the value of planning. Use monthly projections, hold extra cash for estimates, and time larger deductions when profits spike to smooth your effective rate.
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Which CLEAR EDGE pillars usually move the needle first?
For many owners, Legal Structure, Deduction Optimization, and Retirement Planning deliver early wins. Credits and Real Estate become powerful when your facts and documentation support them.
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What documentation should I keep to stay audit-ready?
Board or manager minutes, your accountable plan, mileage and expense logs, payroll reports, retirement plan documents, leases, cost segregation files, credit studies, and short memos that explain the purpose and math behind each move.
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How do multi-state operations change the plan?
They influence where income is taxed and which elections help. Confirm nexus, apportionment, and whether a pass-through entity tax election reduces your burden. Establish a compliance rhythm to ensure filings are completed on time.