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The HSA Expert

Most people are overwhelmed when choosing health insurance at work. When I was new and first on the job, I had no idea what insurance benefits were - what was good, what was bad or how much I should pay for any of it. I know exactly what you’re up against. I’ll review your health plan choices at work and tell you - one on one - which plan to choose. You’ll be saving smarter now by keeping more money in your own pocket while building wealth to safeguard your future. So that you’ll be able to get the healthcare you need. So that you’ll be able to get healthcare when you need it. So that you’ll never have to worry how to pay for healthcare again.

Scott-W-Dowling

I Didn’t Know That

“I didn’t know that!" I have heard that a lot lately. As I gear up for the upcoming Midyear HSA Review for 2026, I have spoken to a lot of people about how to best optimize and maximize Health Savings Accounts - especially for 20 and 30 year olds who are new to getting health insurance at work and have little experience or knowledge as to any of it. And then there are the benevolent parents who keep their adult kids on their insurance until they are 26 years old - because…it is so darn cheap....

Have You Ever Been The Frog In The Pot?

When you visited the doctor last, did you hand the person at the front desk the plastic card that kinda looked like a credit card? Before you handed them the card, did you ask how much your visit would cost? When you left the doctor’s office, did you get a receipt showing what you purchased and how much you paid for it? Can you name something else where you just hand someone a blank check, make a purchase and walk out without knowing what you paid? And you might even have a smile on your...

Are You Being Fooled?

“I don’t even understand the system…I can’t imagine how these guys can understand it.” I was speaking to a gentleman I have known for a long time, but have not seen since Christmas. “These guys” are our 20-something year old sons, who were standing next to each other after Mass the other day. “The system” refers to healthcare in the United States. I do not like to refer to “the healthcare system”, because I don’t buy it. Call me a dissenter or contrarian. Healthcare Is Not Health Insurance. I...

Raised Right On The South Side

Watching the Milan-Cortina Olympics, I always looked for our favorite hockey player - #37 on the USA Women’s team. After watching the United States defeat Canada for the Olympic Gold Medal in Milan - what a thrilling game! - we kept the broadcast on to enjoy all of the celebrating. With all of the hugging, smiles and tears and the camera whipping around, it was hard to find #37, she is isn’t the tallest. Then, all of a sudden, the camera turned to a USA player talking very directly to the...

What To Say When You Know You Are Right!

"Father, I don't hear confession and you don't coach this team." Father is Father John P. Raynor, SJ, president of my alma mater, Marquette University. He’s the boss. I was lucky enough to meet Father Raynor a few times. When I introduced him to my family at the President’s Reception during graduation week, he looked at me a bit puzzled, pointed toward my big sister and said, “How did we let this one get away?” I shrugged my shoulders. My sister just laughed. Father Raynor was a joy to be...

IRL Clients Share: Getting Better Benefits Without Insurance Company Bias

Hey Reader, “Welcome! We have a few things for you to complete.” I sit with four other new hires in a conference room. “Fill these out. If you have any questions, just ask”, says the company HR representative. Before me I have IRS Form W9, a request for my driver’s license and a bunch of information about insurance - medical, dental, life, disability and 401(k). “Choose the insurance you want and sign.” I thought to myself, “Is this it?” I was once fresh out of college, ready to take on the...

Thinking About Mom To Start The New Year

For better or for worse, I think about insurance a lot. And, if you think about it, nothing really happens without insurance. I can just see my pal, Lee, right now texting me the Facepalm emoji!!! “I’m really disappointed that I didn’t get to make shortbread for Hogmanay!”, I told my mother-in-law as we drove north up the Edens Expressway on the way to her home following the New Year’s celebration. We had just been talking about recipes and I mentioned that my Mom always made shortbread for...

December 22nd - A Day That Will Live In Infamy, At Least For Me

Hey Reader, I literally saw my life flash before my eyes. Seriously. While it sounds very trite, you’ll know it when it happens. Gene and I were talking as we were westbound on US60 heading back to my hotel after watching my daughter’s basketball game in the Nike Tournament of Champions. We heard a bang and then screeching tires getting louder and louder. I-10 US60 Interchange All of sudden, there was a really loud bang this time and I couldn’t breathe. I could smell something burning, but...

Lucky To Be Thankful

Hey Reader, You never know what is going to happen. Sometimes it’s helpful. 40 years ago this Thanksgiving was such a time. I apologized to Aunt Betty, but I was not going to be with her, Uncle Don and cousin Tom for Thanksgiving in Chicago. I did not tell her why. The only one that I told was my sister. All of the airlines were having “fare wars” as travel picked up following a newly robust US economy. Before the middle 80s, there wasn’t the same frequency of air travel that we take for...

Your HSA Will Set You Free

I’m far from a movie fan…Diner is my favorite. The kids always give me a hard time. Sometimes a movie strikes me. The Truman Show Truman Burbank had no idea his entire life had been manipulated, orchestrated, controlled. His life was for the benefit of those that controlled him and those watching at home. Truman was the star of a grand money-making enterprise. He did not know it. He was not told about it. And he was not paid for it. To be honest, he was robbed! And while the man in control...

Most people are overwhelmed when choosing health insurance at work. When I was new and first on the job, I had no idea what insurance benefits were - what was good, what was bad or how much I should pay for any of it. I know exactly what you’re up against. I’ll review your health plan choices at work and tell you - one on one - which plan to choose. You’ll be saving smarter now by keeping more money in your own pocket while building wealth to safeguard your future. So that you’ll be able to get the healthcare you need. So that you’ll be able to get healthcare when you need it. So that you’ll never have to worry how to pay for healthcare again.