What I Wish I’d Known About Taxes Before I Hit $100K with Cindy Dillard
You’re crushing it in your coaching business. Revenue is up. Clients are rolling in. Then April hits, and your CPA sends you a bill for $25,000 you didn’t plan for.
I’ve seen this happen to too many coaches. You’re so focused on growing your business that tax planning falls to the bottom of your list. Then suddenly, you owe more than you have in your account.
This doesn’t have to be your story. Today, I’m sharing my back-pocket secret weapon: Cindy Dillard, the tax strategist who’s saved Justin and me from exactly this scenario. She’s taught us how to optimize our taxes, plan quarterly, and actually understand what we’re doing with our money.
If you’ve ever felt confused about LLCs versus S-Corps, wondered what you can actually deduct, or just wanted to stop feeling anxious about tax season, this episode is for you.
Why a Tax Strategist Changes Everything
Most CPAs will prepare your return and send you a bill. That’s their job.
A tax strategist does something completely different. They look at your entire financial picture throughout the year and help you make decisions that minimize your tax burden legally and strategically.
Cindy’s approach is proactive, not reactive. She wants to know when your revenue increases, when you’re considering major purchases, and what your expenses look like. Then she runs the numbers to show you exactly where you stand.
The result? No surprises. No scrambling. Just clear, strategic planning that puts you in control.
I’ll be honest: before working with Cindy, I had that nervous belly feeling every tax season. Not anymore. Now I know exactly where we stand, what we owe, and how to plan for it.
LLC vs S-Corp: What You Actually Need to Know
This is the question I get constantly. “Amanda, should I be an LLC or an S-Corp?”
Here’s what Cindy taught me: an LLC is a legal structure for asset protection. How you file your taxes is separate.
The breakdown: An LLC with one member can be taxed as a sole proprietor, S-Corp, or C-Corp. Cindy almost always recommends S-Corp taxation because you save approximately 16% on your profits.
Think about that. If you’re making $100,000 in profit, that’s $16,000 back in your pocket instead of the IRS’s.
The S-Corp requirements: You need to be on payroll if you’re profitable. Cindy won’t put you on a W-2 if it puts you in the red, which I love. She’s strategic about timing.
You also commit to staying an S-Corp for five years once you elect it. This isn’t something you bounce back and forth with based on how you feel that year.
Bottom line: If you’re making consistent profit in your coaching business, S-Corp taxation probably makes sense. Talk to a tax strategist (not just any CPA) to confirm.
The Home Office Deduction You’re Probably Missing
Working from home as a coach? You can deduct your home office expenses.
Most coaches either skip this entirely or have no idea how to calculate it properly. Cindy broke down both methods for me.
Method 1: Actual Square Footage Measure your dedicated office space. Calculate the percentage of your home it represents. Apply that percentage to your mortgage, utilities, internet, insurance, and maintenance.
Example: If your office is 200 square feet and your home is 2,000 square feet, that’s 10%. You can deduct 10% of those expenses.
Method 2: Simplified Method The IRS allows $5 per square foot up to 300 square feet maximum. That’s a $1,500 deduction with zero math.
Choose the method that gives you the bigger deduction. Either way, track it. This is money you’re leaving on the table if you ignore it.
What Never to Pay From Your Business Account
Cindy was crystal clear on this. There are three things you should never pay from your business account.
Never claim:
- Your mortgage. Pay it personally. If you want to claim a home office deduction, that’s separate.
- Dry cleaning. Unless you’re traveling for business, this is personal.
- Groceries. Unless you’re hosting a client event or workshop, groceries are personal expenses.
She shared a story about an audit where the IRS agent found personal items mixed with business expenses. That triggered a complete scrutiny of every receipt. Don’t give them a reason to dig deeper.
The exception: If you host events or workshops where you provide food, those groceries are deductible. But mixing your weekly Trader Joe’s run with business expenses? That’s asking for trouble.
Cindy keeps separate cards for business and personal use. She’s not perfect (she admitted to the occasional “which card?” moment), but she tries to maintain clear separation.
The First Step to Getting Organized
If you’re feeling overwhelmed about taxes, Cindy’s advice is practical and doable.
Start here: Go through your bank statements and credit card statements for the last year. Get familiar with what you’re spending money on.
You don’t need to categorize everything perfectly. Just look at totals. Notice patterns. See where your money is going.
If you have a teenager: Give them this job. Cindy said some of the Excel spreadsheets clients bring her are incredible because their kids created them. Teenagers are often better at this than we are.
If 2025 feels too daunting: Just do January 2026. Once you see how manageable one month is, you’ll gain confidence to tackle the rest.
For ongoing organization: Set up a system now. Whether that’s a spreadsheet, affordable bookkeeping software, or hiring a bookkeeper, get something in place for moving forward.
One critical note: Don’t use QuickBooks Self-Employed. Cindy was adamant about this. It won’t count meals. It won’t count internet. It won’t count anything with personal use. You’re better off with a simple spreadsheet.
Quarterly Planning Eliminates Surprises
The biggest difference between working with a tax strategist versus a traditional CPA is ongoing communication.
Cindy doesn’t want to talk to you once a year. She wants to know when your revenue increases, when you make a big purchase, when something changes in your business.
Why this matters: She can run projections throughout the year. If you’re going to owe $30,000 in April, she’ll tell you in September. Then you have time to make quarterly payments, adjust your withholding, or make strategic purchases that reduce your tax burden.
The alternative: Getting hit with a massive bill in April with no warning and no plan to pay it.
I can’t emphasize enough how much this approach has changed our relationship with taxes. Instead of dreading tax season, Justin and I actually look forward to our meetings with Cindy. We know where we stand. We know what’s coming. We can plan accordingly.
S-Corp Payroll: The Details That Matter
If you elect S-Corp status, you need to understand the payroll requirement.
The rule: If you’re profitable, you must pay yourself a reasonable salary through W-2 payroll.
What “reasonable” means: Cindy looks at industry standards for your role. If you’re doing the work of a coaching business owner, she’ll set your salary accordingly. This isn’t something you can lowball to avoid taxes.
The benefit: The remaining profit can be distributed as dividends, which aren’t subject to self-employment tax. This is where that 16% savings comes in.
The timing: Cindy won’t put you on payroll if it puts your business in the red. She’s strategic. If you’re close to profitability but not quite there, she’ll wait until you cross that threshold.
What to Do This Week
Tax planning doesn’t have to be overwhelming if you break it down into manageable steps.
This week: Pull your bank and credit card statements for January 2026. Spend 30 minutes reviewing where your money went. Don’t judge. Just notice.
This month: Decide on an organization system. Will you use a spreadsheet? Hire a bookkeeper? Set up proper accounting software (not QuickBooks Self-Employed)?
This quarter: If you don’t have a tax strategist, find one. Not just a CPA who files your return, but someone who proactively helps you plan throughout the year.
Calculate your estimated quarterly payments based on last year’s income. Even if they’re not perfect, getting something paid quarterly prevents a massive April surprise.
Review your business structure. Are you still a sole proprietor when you should be an S-Corp? Talk to a professional about whether it’s time to make that switch.
Why This Matters for Your Coaching Business
Every dollar you save on taxes is a dollar you can reinvest in your business, pay yourself, or save for the future.
Most coaches are so focused on revenue that they ignore the profit optimization piece. You’re leaving thousands of dollars on the table every year because you don’t understand the tax code.
I’m not saying become a tax expert. I’m saying find a tax strategist who will guide you through this process and teach you along the way.
Cindy’s approach is education-focused. She doesn’t expect me to do the work, but she wants me to understand what she’s doing and why. That empowerment has completely changed how I view our business finances.
You deserve the same clarity and confidence.
Ready to stop dreading tax season? Connect With Cindy Dillard
- Phone: 602-368-3588
- Email: cindy@samboyappletax.com
She works with clients nationwide and specializes in helping entrepreneurs optimize their tax strategy year-round.
Connect With Me
- Want to build a coaching business that generates consistent revenue?
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