Winter & Associates, Inc.

04/09/2026

What $100 Invested in 1928 Would Be Worth Today

Many people think the biggest risk with money is losing it. A bad investment. A market crash. A bet that doesn't pay off.But what if the most expensive financial decision isn't a bad choice — it's no choice at all?That's what nearly a century of market data suggests. And the numbers are hard to ar...

03/09/2026

A More Flexible Way to Think About Retirement

Many retirement plans are built on a quiet assumption: that spending stays roughly the same from year one to year thirty.It sounds reasonable. But research suggests it's not how retirement actually works — and planning around that assumption might create more anxiety than it prevents.

02/09/2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Many people think about taxes once a year — when April rolls around and it's time to file.By then, the year is already in the rearview mirror. The decisions that could have made a difference? Many of the deadlines for them already passed.

01/09/2026

5 Financial Crossroads That Could Reshape Your Future

You know how life tends to throw in a few plot twists?They don't ask if you're ready. They just show up—with potential financial consequences tagging along.A layoff. A diagnosis. A parent who needs help. These moments don't come with instruction manuals. But they do come with price tags, deadlines...

12/19/2025

Happy Holidays and Happy New Year from your team at Winter & Associates! We hope this season brings you peace, joy, and time well spent with those who matter most to you. Thank you for being part of our community!

12/09/2025

Common Retirement Regrets—And Proactive Moves to Consider

Many people don’t regret being retired. They regret how they got there.1“I wish I had saved earlier.”“I didn’t think long-term care would matter.”“I should’ve waited to claim Social Security.”Hindsight hits hard when it’s tied to your potential freedom and options.The good news? ...

11/27/2025

Please note our office is closed November 27th and 28th to spend time with our families.

We hope you have a Happy Thanksgiving filled with many blessings!

11/09/2025

How to Talk to Your Aging Parents About Estate Planning (Without Making It Tense)

These conversations aren’t easy.Bringing up long-term care or estate planning with aging parents can feel like stepping on a landmine—awkward, emotional, maybe even a little intrusive.But if you wait until something happens—a fall, a diagnosis, a hospital stay—you're not just having the conv...

10/16/2025

Curious if our services might be the right fit for you? Check out our website to learn more about Who We Help: https://www.winterassoc.com/who-we-help.

WHO WE HELPOur core clients often fall into one of the categories below, though we work to bring life-changing guidance to generations of individuals, families, and businesses from all stages of life.

10/10/2025

Our team had the pleasure once again of volunteering at The Open Door, sorting through truckloads of food coming into their warehouse that then gets distributed out to over 25,000 Dakota County families and individuals in need each month through their onsite food pantry and partner programs. We also value these opportunities to come together as a team to do something fun and impactful for our community outside the office.

Check out our website for more information: https://www.winterassoc.com/community-engagement.

10/09/2025

Overlooked Retirement Expenses (And How to Plan for Them)

A comfortable retirement doesn’t come with a fixed price tag.Expenses can change over time, and some of the most important ones are easy to overlook.That’s one reason about 45% of retirees could run out of money in retirement.1The good news? That outcome isn’t inevitable. The key is recognizin...

10/02/2025

Winter & Associates hosted our “Future Watch” event last week at St. Catherine’s University. After some mingling and a warm welcome from Nicole, our very own Taylor Floren took the floor with some discussion around ChatGPT use, followed by professional futurist, Stephen Dupont, MSc, APR, Fellow FRSA, who shared his thoughts about thinking forward to and navigating the future. We want to thank Stephen and everyone who could attend for sharing your time with us!