Tax Planning
Most High Earners Overpay in Taxes. Here's How We Approach It.
Year-round tax planning for high earners in Grand Rapids and nationwide. Roth conversions, backdoor Roth, HSA strategy, tax-loss harvesting, and coordination with your CPA, all before December 31.
Most people only think about taxes in April. By then, most of the moves that could have saved money are already off the table.
Tax planning and tax filing are not the same thing. Filing is what happens after the year is over. Planning is making decisions throughout the year so the number at the bottom of your return is as low as legally possible.
The most common places high earners leave money: maxing out the wrong type of retirement contributions for their bracket, missing the HSA investment opportunity entirely, skipping the backdoor Roth when income crosses the limit, and not harvesting losses in brokerage accounts before year-end. None of this requires anything complicated. It just requires someone who knows what to look for.
How Tax Planning Works in Practice
Roth conversion analysis
Each year, we look at your income, your current tax bracket, and what you expect in retirement to decide whether a Roth conversion makes sense, and if so, how much. The window to convert at a favorable rate is often narrow.
Backdoor Roth IRA
Above the income limit for Roth contributions ($168,000 for single filers in 2026)? We run the backdoor Roth process every year so that door stays open, including handling the pro-rata rule if existing IRA money is involved.
HSA optimization
An HSA is the only account that is triple tax-advantaged: deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses. Most people use it like a debit card. We invest it and let it compound.
Tax-loss harvesting
When positions in your brokerage account drop in value, we sell them to realize a loss, offset gains elsewhere, and immediately buy a similar fund. Done consistently, this reduces your annual tax bill with no change to your investment strategy.
Asset location strategy
Which account type holds which investments matters. Bonds and high-dividend funds belong in IRAs. Growth stocks belong in Roth accounts. The right placement meaningfully improves your after-tax return over time.
Year-end tax planning
Most meaningful tax moves have December 31 deadlines. We review your situation in November and make sure nothing gets missed before the calendar flips.
Tax Planning FAQ
How can I legally pay less in taxes as a high earner?
The most commonly missed moves: max out your pre-tax retirement contributions, do a backdoor Roth IRA if you are above the income limit, fund your HSA all the way and invest it instead of spending it, harvest tax losses in your brokerage account, and make sure you are placing investments in the right account types. The right combination depends on your income, tax bracket, and goals. We build the plan around all of it.
What is a backdoor Roth IRA and do I need one?
If your income is above the Roth IRA contribution limit (around $168,000 for single filers in 2026), you cannot contribute directly to a Roth IRA. A backdoor Roth is a legal workaround: you contribute to a Traditional IRA and convert it to Roth shortly after. It takes some coordination, especially if you have other pre-tax IRA money sitting around. We run through it each year so nothing creates an unexpected tax bill.
Should I do pre-tax or Roth 401(k) contributions?
It depends on whether you expect your tax rate to be higher now or in retirement. If you are in a high bracket today and expect to be in a lower one later, pre-tax often wins. If you expect to be in a similar or higher bracket in retirement, Roth tends to be better. In practice, the right answer is often a mix of both, and it shifts as your income and life change.
What is the difference between a financial advisor and a CPA for taxes?
A CPA prepares and files your tax returns. Chris does tax planning, which means making proactive decisions throughout the year that reduce what you owe. The two roles work together. We coordinate directly with your CPA so there are no surprises at tax time and the planning actually shows up in the numbers.
What is tax-loss harvesting and is it worth it?
Tax-loss harvesting means selling investments that have dropped in value to realize a loss, then using that loss to offset gains elsewhere in your portfolio. It reduces your tax bill without changing your overall investment strategy. It is worth it when done consistently, but requires attention to the wash-sale rule and coordination across accounts.
When is the best time to start tax planning?
Now, whatever time of year it is. The biggest tax moves have deadlines: Roth conversions, loss harvesting, and HSA contributions all have to happen before December 31. Backdoor Roth contributions need to happen before the tax filing deadline. If you are reacting to your tax bill in April, you have already missed most of the opportunities.
What clients say about working with Chris
"My wife and I have been working with Chris for a few years now. He's been absolutely incredible with helping us manage our finances. I highly recommend Chris to anyone who is looking for a faith-based and trustworthy advisor!"
"Knowing that my financial advisor is assisting me in a fiduciary capacity regarding my retirement, liquidity needs, budgeting, and tax planning allows me to have tremendous confidence in my financial situation. My advisor is well-trained, qualified, and knowledgeable. I foresee doing business with Villaire Financial for quite some time."
"Thankful for Chris and his financial literacy and help, but most importantly thankful for his heart to get to know his clients on a personal level outside of financial help as well. He really knows what he is doing and has a passion to help you meet your goals!"
Testimonials from current clients of Villaire Financial, LLC. No compensation was provided for these reviews. Individual experiences and results will vary. These testimonials may not be representative of the experience of other clients.
A fiduciary CFP® who built this firm for people in their 20s and 30s.
Chris Villaire started Villaire Financial because most wealth management firms won't work with you until you have $250,000 or more. The decisions that matter most, how to allocate your first 401(k), when to start Roth conversions, how to handle a job change, happen well before that. He built this firm specifically to help people in the wealth-building stage, not after it's already done.
Based in Grand Rapids, MI. Serving clients nationwide.
Simple to get started. Straightforward from there.
Book a free 30-minute intro call
Tell us what's going on. We'll answer your questions honestly and tell you upfront whether we think working together makes sense.
Build your financial plan
We go deep on your income, spending, investments, debt, and goals, then deliver a complete financial plan in about 30 days. You understand every piece of it.
Ongoing planning and support
Twice-a-year reviews, ongoing investment management, and an advisor who's available when something comes up between meetings.
Stop Leaving Money on the Table Every Year.
Book a free 30-minute call. We'll talk through your tax situation and tell you exactly what moves you're missing.
Guides on Tax Planning
HSA: The Most Underutilized Retirement Account You're Not Maxing Out
Your HSA is arguably the best tax-advantaged account available — triple tax-free and underused by most people. Here's how to max it out the right way.
What Is a Backdoor Roth IRA and Should You Do One?
You earn too much for a Roth IRA. Here's the legal workaround, step by step, and who needs to be careful.