Tax planning isn’t just for the ultra-wealthy or big corporations. In fact, many individuals and small business owners miss out on thousands of dollars in savings simply because they wait until tax season, when it’s often too late to make changes.
Here are seven real-life situations where proactive tax planning can make a big difference, and how a CPA can help you navigate them with clarity and confidence.
📈 1. You Have Equity Compensation (RSUs, ESPPs, or ISOs)
Equity comp can trigger tax bills at vesting, sale, or exercise, and the rules are complex.
How a CPA can help:
- Forecast your tax liability before you sell or exercise shares
- Avoid AMT surprises with incentive stock options
- Track your cost basis correctly to avoid overpaying
₿ 2. You Trade Crypto or Hold Digital Assets
Crypto is taxed differently than most people expect; even swaps and staking rewards can be taxable.
How a CPA can help:
- Classify and report your gains, losses, and income correctly
- Navigate decentralized exchanges and missing cost basis
- Help you harvest losses and avoid audit triggers
🏠 3. You’re Selling Property or Real Estate
Capital gains from a home sale, rental property, or inherited real estate can cause major tax consequences unless you plan ahead.
How a CPA can help:
- Determine eligibility for capital gains exclusions
- Set up a like-kind exchange (1031) if you’re investing again
- Track depreciation recapture and passive activity losses
💼 4. You Run a Small Business or Side Hustle
Self-employment opens up opportunities for deductions, but also responsibilities like estimated taxes and payroll compliance.
How a CPA can help:
- Set up the right business entity for tax efficiency (e.g., LLC vs. S-Corp)
- Maximize deductions and avoid red flags
- Keep your books clean for year-end planning and audit protection
💰 5. You Had a Big Income Change This Year
Whether you got a raise, bonus, new job, or took time off, income swings can lead to unexpected tax outcomes.
How a CPA can help:
- Adjust your withholding or estimated payments
- Take advantage of tax brackets (e.g., harvesting gains in a low year)
- Plan retirement contributions strategically
🎓 6. You’re Paying for College or Supporting Family
Education credits, dependent deductions, and gifting strategies can all impact your tax picture.
How a CPA can help:
- Maximize available credits (like the American Opportunity Credit)
- Coordinate education savings with your overall financial plan
- Structure family support to avoid gift tax issues
📅 7. It’s Near the End of the Year
By December, it’s often your last chance to make moves that affect your tax bill.
How a CPA can help:
- Harvest losses or gains for tax optimization
- Make last-minute retirement contributions
- Defer or accelerate income or expenses based on your situation
👩💼 Why Work with a CPA for Tax Planning?
A good CPA doesn’t just fill out forms, they help you:
- Understand your options and make smarter financial decisions
- Avoid IRS surprises and costly mistakes
- Save money legally and ethically by planning ahead
Whether you’re a tech employee with RSUs, a crypto investor, or a small business owner, proactive planning now can save you a lot of stress and money later.
✅ Ready to Plan Ahead?
I offer year-round tax planning and prep for clients with complex financial lives. If you think you might benefit from a second opinion, or just want to make sure you’re not leaving money on the table, let’s talk.