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Blog

Tax Season Has Two Dates. Many People Only Show Up for One.

by Tim Obendorf on Nov 5, 2026
Categories
Tax Planning
Retirement
Finance
Savings

Ask people when “tax season” is, and many will say spring.

That’s when the documents get gathered, the appointment gets booked, and the return gets filed. It’s also, for a lot of financial decisions, several months too late.

The year the return describes ended on December 31. For a number of items...

Are You Giving on Purpose — or Just in December?

by Tim Obendorf on Nov 3, 2026
Categories
Finance
Tax Planning
Estate Planning
Investments
Family

You know the season. Envelopes in the mailbox, messages in your inbox, and a cashier asking if you'd like to round up for a good cause.

And somewhere between Thanksgiving and New Year's Eve, a lot of generous people make many of their charitable decisions in a hurry.

In 2025, nonprofits received 37%...

Retirement Planning: Inflation and Social Security COLA Update

by Tim Obendorf on Oct 28, 2026
Categories
news
Retirement Planning: Inflation and Social Security COLA Update

Financial Impersonation Scams: What to Watch For

by Tim Obendorf on Oct 26, 2026
Categories
Privacy
Risk Management
Finance
Savings
Family

Many people picture a scam as something obviously off: a strange email, a robotic voice, a too-good-to-be-true offer.

The more dangerous version sounds like rescue. A calm, professional voice tells you your bank account has been compromised, and they’re calling to help you fix it before it’s too late...

2 men standing on green grass field near body of water during daytime by Marc Najera courtesy of Unsplash.

Medicare Open Enrollment

by Tim Obendorf on Oct 21, 2026
Categories
news
Medicare Open Enrollment

Six Estate Planning Assumptions Worth a Second Look

by Tim Obendorf on Oct 7, 2026
Categories
Estate Planning
Family
Insurance
Retirement
Tax Planning

It's easy to set estate planning aside once you've done a version of it. You sign the paperwork. You name a beneficiary. You mentally close the file.

The only thing is, the file keeps changing. Accounts get opened. Families grow. Laws shift. And in the space between signing and revisiting, a handful...

AI Gives Answers: Guidance Requires Judgement

by Tim Obendorf on Sep 25, 2026
Categories
news
We’re noticing a trend in the industry where clients are coming into their advisors with financial strategies developed via AI.

More Than a Number: The Four Risks That Shape Your Retirement

by Tim Obendorf on Sep 11, 2026
Categories
Retirement
Risk Management
Health
Investments
Finance

Many people can tell you their portfolio balance. Far fewer can tell you what else determines whether their retirement actually works.

That's understandable. The balance is the number on the statement. It's concrete, and it feels like a score. But judging retirement readiness by that one figure is a...

Retirement Isn't Just About How Much You Save. It's About When.

by Tim Obendorf on Sep 8, 2026
Categories
Retirement
Risk Management
Investments
Finance
Savings

You can do everything right on paper — save diligently, spend reasonably, stay invested for the long haul — and still land in a very different retirement than someone who did the same things.

The difference often comes down to a factor many retirement checklists leave out entirely: timing.

A lot of...

Permission to Spend in Retirement: A Skill Rarely Taught

by Tim Obendorf on Aug 27, 2026
Categories
Retirement
Lifestyle
Finance
Savings
Family

For decades, you trained one financial muscle: save, invest, don't touch it. Then retirement arrives and asks you to do the opposite.

Nobody teaches that part. There is no course on how to spend the money you spent a lifetime building, so the discipline, the caution, and the watchful eye on every...

What to Do With Your Next Dollar: A Financial Order of Operations

by Tim Obendorf on Aug 5, 2026
Categories
Finance
Savings
Investments
Retirement
Risk Management

What do you do when you earn well and have generally dialed in the fundamentals: save, invest, reduce debt, stay protected? The challenge was never knowing what to do. It's knowing what to do first, and in what order.

That's a harder question than it looks. Each of these priorities is sound on its...

Trump Accounts: What Parents and Grandparents Should Know

by Tim Obendorf on Jul 17, 2026
Categories
Education
Savings
Family
Tax Planning
Finance
Investments

Trump Accounts have been in headlines for months. Few of those headlines explain them the same way.

Depending on the article, they sound like a college fund, a retirement account, or something brand new altogether.

For parents and grandparents trying to figure out whether any of it matters for their...

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Office Locations

OUR CHICAGO LOCATION

Steward Advisors
625 West Adams Street
Chicago, IL 60661
(224) 300-0284

 

OUR SCHAUMBURG LOCATION

Steward Advisors
1320 Tower Rd
Schaumburg, IL 60173
(224) 300-0284

Contact Us

For important information about Steward Advisors, click the following links to read our client relationship summary (Form CRS), our Brochure and Supplement (ADV Parts 2A and 2B) and our Privacy Policy. 

Financial Advisors do not provide specific tax/legal advice and this information should not be considered as such. You should always consult your tax/legal advisor regarding your own specific tax/legal situation.

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