January 2026 – Oh… High School…

Welcome to 2026! 
It’s crazy how I’m writing this in mid-to-late January and it already feels like we’ve been in 2026 for… a while.
Time just keeps marching forward.

Here’s the Agenda

1. Taxes… shudder…

2. Book Recommendation

3. Oh… The Days of High School Drama… HELP!

Tax Season

I do not like to procrastinate, so I’m already thinking about taxes and gathering everything we need.
I am a Medicare nerd, not a tax nerd, however, I am lucky to know a few tax nerds who are kind enough to come on the channel and share their thoughts.

Most recently, my CPA – Daniel Astleford – came on the channel and talked about how a little bit of tax planning in retirement can save quite a bit of money.

You can click HERE to watch or click the picture:

His 2nd video hasn’t been released yet, but you get to have the first look. 
It is all about how to gift to children (or others) in a tax-effective way.

You can click HERE to watch or click the picture.

Many years ago, my parents were kind enough to gift my wife and me money to help us with the downpayment on our first home.
Daniel goes over this and other gifting situations from a tax lens.

This is not me saying to use him or his services, just a topic to consider for those who have plans to use their money in this way.

Some of you are DIY-ers, some of you are not.
My advice to those of you who are NOT DIY-ers (like me) is to get started early.
Don’t wait until the last minute.
This applies to my specialty (Medicare) as well.

Waiting until the last week or the last day or the last hour… (yes… this happens all the time) can leave you with fewer options, so please, don’t procrastinate your Medicare, financial planning, estate planning, or… taxes 🙂

Book Recommendation

The Boy, The Mole, The Fox, and the Horse
Charlie Mackery

I have two things for you here…

Each year, I publish my list of books read for that year.
I usually try to finish one book per week, however… in 2025… that did not happen.

But… a lot of good things did happen this year that got in the way of this goal.

So… Here is the list of the books read this year with some ratings next to them.

2025 Book List

The ACTUAL book recommendation for this month is one of my top 5 all-time books, and it only takes 10-20 minutes to read but my goodness… if you take a little longer and think about the messages in this book, they are powerful.

If you haven’t read it already, you have to get The Boy, The Mole, The Fox, and the Horse by Charlie Mackesy.
It was turned into a short, 30-minute movie on Apple TV as well, but read the book.
Trust me on this one.

This was a Christmas present for all the friends and family.

Get it Here

Your Recommendations
I would love your book recommendations of what I need to read in 2025!

Words of Wisdom – Oh… The Days of High School Drama… HELP!

My dream job when I graduated high school was to be a high school basketball coach.
My dad was my coach up until high school and I often think about his influence on me and the other players on the various teams he coached.
He made a positive impact on a lot of peoples’ lives, and I hoped to do the same.

I wanted to figure out a way to make enough money to never have to worry about it again, then move to a small town and coach the local basketball team.

I love basketball.
I love coaching players.
It felt like a good plan.

Plans change.

The more I saw behind the scenes with coaching, the more I realized… I don’t every want to be a head coach. There’s just so much to deal with!

The parents, teenage attitudes, social media now, referees, bus schedules, school administrators, other teams and practice schedules, fundraising, and on and on and on.
It’s a nightmare.

So… this past year, I had my first opportunity to be an assistant coach… and I love it.

The varsity assistant coach kind of gets the best of both worlds.
When the head coach gets mad, I’m there to take the player and calmly walk through how to improve something.
I get to be the “good guy.”

Parents don’t come to me with complaints about playing time, I don’t schedule anything or worry about fundraisers.
I’m there to help develop the players and scout the other teams.

I love it.

I Ain’t As Good As I Once Was

Another fun part of this is it keeps me in relatively okay shape.
I jump in and still play with the high school kids, which is both encouraging and humbling at the same time.

As long as I don’t have to run up and down the floor more than 4 times, I’m happy with my ability to play with these young bucks.

The reality is… in real basketball… you have to run up and down the floor more than 4 times, and these high school punks have unlimited energy.
It’s nuts! I’m over here huffing and puffing… sweaty… can’t talk or breathe… and they are just sprinting all over the place.
A lot of times they are running in places they shouldn’t, and wasting energy, but the fact that they can do that is great (for them) and frustrating (for me).

I don’t feel like I’m that old, and I remember the days when I could do that.
They don’t seem that far away… but to my body… they feel like a past life I’ll never come close to realizing again.

Speaking of Feelings…

It’s strange to be in the halls of a high school again.
This school is not the school I graduated from, but it is the exact same building layout as the school where I graduated.
The sights, sounds, and smells take me right back to those days.
The stress, anxiety, search for self, and pressures to be with the right people, attract the right people, and try to keep up with what my parents, teachers, and coaches told me to do.

The reason I love the book recommendation from this month is that it touches on so many of the insecurities I have had throughout my life, giving wise perspectives to what really matters.
Now that I have a teenager of my own and two others coming… I find myself trying so hard to shield my kids from the pain and fears I had growing up.

Some of these fears seem to be with most kids:
The fear of not belonging.
The fear of not being good enough.
The fear of failure.

Two quotes from the book:

1. “Imagine how we would be if we were less afraid.”
Man… that gets me thinking…

2. “What is the bravest thing you’ve ever said?” asked the boy.
“Help,” said the horse.
“Asking for help isn’t giving up,” said the horse.
“It’s refusing to give up.”

My favorite part of coaching has been the one on one conversations with players who are courageous enough to come to me and ask for help.
That’s hard to do as a teenager. You have to remember that to make a varsity high school team, most of these kids have been the best players on their respective teams… for their entire lives.

Everyone – their parents, their coaches, their family member – have been telling them they are the greatest since they were 5 years old. And now, they get to a varsity team where you have 30 kids that were all “the best” going against other schools with even better players, and it’s quite a shock to the emotional system.

We’ve seen guys quit.
We’ve seen guys get intimidated and shrink because they don’t know how to handle it.
And… we’ve seen guys realize they need to get better, work harder, and reach out for help.

Teenagers are kind of notoriously hard to get to open up, but, when I come to think of it… us adults can be, too.

Asking for Help
Many of you know about last month’s message with my daughter and her hospital stay.
That cost video is out now: Noel’s Appendix Costs

It was hard to ask for help with the kids and coordinating life.
My pride gets in the way sometimes.
My desire to not be a burden on others gets in the way.

I receive genuine joy when my small sliver of expertise is able to help somebody, and I came to realize that if people didn’t ask me for help, I’d miss out on those opportunities… and a career for that matter.

So, if I need help, who am I to withhold that joy and sense of purpose from someone else?

My resolution this year is to be more willing to ask for help.

I’m curious if you have any unique resolutions for this new year.

I appreciate you taking the time to read these and deal with my ramblings.
I hope you have a wonderful month, and I’ll see you in the next newsletter.

Erik

PS – Some coaching pictures 🙂