Tradewinds Tax Planning

01/08/2026

With the holiday season behind us and the new year officially here, we wanted to quickly check in with you. Whether you’re still writing “2025” on everything or already planning how to crush your goals in 2026, we hope that the year ahead brings you good things!

Here’s to a fresh start and making the most of every opportunity that comes your way. What's one goal you're looking to accomplish in 2026? Comment below, we'd love to hear!

01/01/2026

Happy New Year from all of us at Tradewinds Tax Planning!✨

Wishing you a happy, healthy, and successful year ahead. Looking forward to new beginnings and opportunities in 2026.

12/19/2025

From our team at Tradewinds Tax Planning, we wish you and your loved ones a happy, healthy, and joyful holiday season.

08/13/2024

As excitement for football season builds (Go PATRIOTS!), we’d love to hear who you all are rooting for.

Share it in the comments below. And, of course, if you need help, reach out! We’re just an email or phone call away.

08/06/2024

With many students heading off to college this month, we’re sharing a timely overview of key tax credits and deductions.

Swipe for more information ➡️ As always, feel free to reach out with any questions or needs as we approach the end of 2024.

06/17/2024

Given that June is Annuity Awareness Month, we thought now would be a great time to share an overview of this investment type, which has grown in popularity in recent years.

Swipe for more information ➡️ Have questions? Reach out to us — we’re here to answer your questions.

06/16/2024

06/12/2024

Life insurance isn’t just a smart choice. It’s a crucial step in securing your family’s financial stability and peace of mind.

Unfortunately, 52% of Americans avoid life insurance because they think it's too expensive. What’s more, 82% significantly overestimate its cost, often guessing three times higher than the actual figures.

Let’s look at the real numbers: As of April 2024, the average cost for a healthy 40-year-old purchasing a 20-year, $500,000 term life insurance policy is about $26 per month ($312 per year). However, a 30-year-old woman might pay approximately $205 per year for the same policy, while a 30-year-old man might pay around $352 per year.

Understanding these variations underscores the importance of getting a personalized quote that fits your unique needs and budget. Don’t let myths deter you from this vital protection.

Contact our team today for an accurate, personalized life insurance quote. We’re here to help you find an affordable plan that delivers the security your family deserves.

06/06/2024

Giving to causes you care about not only supports impactful organizations but also brings financial and estate benefits.

Swipe through to explore smart ways to enhance your charitable giving! From donating appreciated assets to strategic timing with donor-advised funds, there are many paths to impactful generosity.

Reach out with questions or to discuss more about charitable giving. Our team is always ready and willing to help.

03/19/2024

Non-qualified Accounts As Tax Planning Tools?

When people save for retirement they almost automatically use accounts that avoid tax now. IRAs, 401(k)s, 403(b)s, 457s, all pretax retirement savings plans. Certainly, long-term savings uninterrupted by withdrawals and the effect of compounding interest on interest earned is unarguably valuable, but doing that in pretax accounts is NOT the only way to have that happen! Non-qualified annuities and Roth IRAs allow the same mechanics of compounding to happen, and in retirement, both can be as valuable depending on the circumstances and actions of the retiree.

Annuities are underappreciated as a tax planning tool, because of the way earnings are treated as ordinary income upon withdrawal. However if annuitized at retirement (an option the advisors that distribute them don’t often value) instead of withdrawing from them, they can offer a dynamic change to the tax profile by way of an “exclusion ratio” on each payment, which can work out as a great tax planning tool.

Roth IRAs are a class of IRAs that allow for tax-free growth and tax-free withdrawals, and many misunderstand how they can be funded. People who cannot make a contribution because of earning too much income can still convert IRA, 401(k), and other pretax accounts to a Roth IRA. Making a contribution is different than making a conversion into one. It sounds like splitting hairs but it is not. So, anyone can have a Roth IRA, it just takes several steps for some people and less for others. As long as you have a good tax planner, it can be done!

These are only a few examples, but as with most things, there are many other options available. But the moral of the story is: Don’t automatically save in pretax accounts. Look at the post-tax options as well and sit down with a tax planner as your Sherpa to help you accomplish your retirement goals!
Let's meet and figure out your tax strategy today!

03/05/2024

Yes, You Can Change Your Tax Outcomes After December 31st!

At this time of year, many people who were getting a refund have already filed their tax return. It leaves the remaining majority of folks who, despite having withholdings, are still going to owe additional tax. We talk a great deal about tax planning and changing behaviors to achieve better outcomes in the future, but many are faced with a tax bill for last year.

So, what can be done? Anything? The answer is YES! It’s actually simple and easy for most folks to substantially reduce the tax liability they are facing by opening a prior-year IRA! It is one of the very few ways the IRS allows you to retroactively affect your taxes. What if you don’t have the cash for an IRA? You can turn assets you already own into a prior year IRA with some simple paperwork, with nothing needing to be bought or sold.

For example, Kevin and Cathy are facing a $3,900 tax bill even after having $12,000 withheld from their W-2s. They have a daughter in college, so there is no cash in the bank to put in an IRA or to pay the $3,900 tax bill. They do, however, have a brokerage account with E*TRADE with a few stocks they have purchased over the years. They can simply do an online IRA application (make sure it’s an application for the previous year, not the current year). When they have account numbers, they can then transfer “in kind” any of the stocks from the regular brokerage account to the IRA without selling them. In a sense, they are taking them from the left pants pocket and putting them in the right pants pocket. The outcome…ta-dah, a $13,000 IRA deduction, and they still own the same stocks!

One thing to consider is that they have now locked up that stock until age 59.5. Another consideration is that stocks are subject to a capital gains tax, which is lower than ordinary income. The suitability of IRAs vs non-qualified stocks is not the point of this post. Anybody making any financial decisions should seek professional advice, which IS the point.

If your tax preparer just says,” It’s bad news” and doesn’t offer at least some solutions, then you should go to a tax planner and work through your options. But just because there is no cash in your checkbook, it doesn’t necessarily mean that nothing can be done.

05/05/2023

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