A Thanksgiving Reflection on Time, Money, and the Moments That Actually Matter
Every year, Thanksgiving pulls a slower, more reflective version of me to the surface. Maybe it’s the season, maybe it’s the kids growing up, maybe it’s the reminder that these windows of time don’t stay open forever.
While prepping for a recent Beer & Money episode, I stumbled across a quote I had jotted down months ago:
“You can pay for time with your kids now, or you can pay for it later. Either way, you pay.”
It hit me harder than I expected.
Not as a financial advisor.
Not as a business owner.
As a dad.
Because so many of us are working hard to create freedom — more time, more space, more options — yet somewhere along the way, the work becomes the priority instead of the life we’re trying to design.
And the truth is, most people never stop to ask:
“If I had the time and money… what would I actually do with it?”
The Spark That Started This Conversation
On the podcast, Alex and I were laughing about how often clients freeze when we ask them what they’d do with more time. Not because they don’t care — but because life gets busy, responsibilities pile up, and they’ve been focused on “the grind” for so long that they haven’t paused to zoom out.
But once they do?
The same themes always surface:
more time with family
more experiences
more presence
more moments that slow life down
Then we ask the uncomfortable follow-up:
“What’s stopping you from doing some of that now?”
That question has brought grown adults to tears.
Not because they’re failing…
But because they suddenly realize how much of life they put on hold in the name of “later.”
Money Isn’t the Point — It’s the Tool
Money can buy time, freedom, flexibility, options.
Money can also consume your time, your focus, and your presence if you’re not intentional.
The difference?
Mindset.
Do you move through life feeling like you have to do everything on your calendar?
Or do you recognize that much of what you do is something you get to do?
I’ll be the first to admit: this shift doesn’t come naturally to me.
Between coaching Madison’s basketball team, supporting Nathan’s involvement on the varsity side, and juggling a winter schedule that leaves little free time, it’s easy to slip into overwhelm.
But when I step back and reframe it?
I get to show up for my kids’ lives.
I get to be present.
I get to be part of these moments that won’t repeat themselves.
That reframing changes everything.
A Lesson from Real Life Planning
A client recently apologized during a review meeting. They had rented a cabin for a month — big, beautiful, right on the lake — and spent the entire time with their kids and grandkids.
Paddleboards at sunrise.
Three-hour breakfasts.
Late-night card games.
Quiet moments. Loud ones.
Memories that will never happen quite the same again.
“It was expensive,” they said. “I’m sorry...we spent more than we told you we would.”
My response was simple:
“Why are you apologizing? You didn’t break the plan... you lived your values.”
And that’s what a good financial plan is supposed to do:
Provide clarity, create permission, and remove guilt from spending on what matters.
Quick Questions to Recenter Your Thinking
Take five quiet minutes this week and ask yourself:
What were the moments this year that I’m truly grateful for?
Where did I spend time because I felt like I had to and where because I got to?
What experience do I want to intentionally design into next year?
If I knew my financial trajectory was solid, what would I allow myself to enjoy more of?
This is where meaning and planning meet.
Your Move
Here are two simple ways to take the next step toward clarity and confidence:
1. Get Your Financial Scorecard
A quick, clear snapshot of where you stand and whether your money is aligned with the life you want to design. Scorecard
2. Book a Meeting
If you’re ready to build a plan that supports both your future and your present, let’s talk.
No pressure. No jargon. Just clarity.
Final Pour
The older I get, the more convinced I am that wealth isn’t measured in account balances — it’s measured in moments.
Thanksgiving reminds us of that.
Family reminds us of that.
Life reminds us of that.
So as you move through this season, try the simple mindshift that’s reshaping my own year:
Less “I have to.”
More “I get to.”
Cheers,
Ryan