Newsletter Archives
Feb 5, 2026 — The Cost of Staying the Same
Comfort has a cost. This reflection explores how habits, familiarity, and the past can quietly shape our lives—and the courage it takes to begin again.
Take Two
For people who know there’s more to life and don’t want to miss it.
WORDS TO WONDER
“The chains of habit are too light to be felt until they are too heavy to be broken.”
— Warren Buffett
PERSPECTIVES TO PONDER
After college, I lived in a small two-bedroom, one-bath house with four other guys. Our tiny house was never meant for five people. We assumed it would be temporary—but comfort has a way of extending timelines, and we ended up staying for years.
The landlord had one unusual rule: we were not allowed to change the phone number.
The house had belonged to his grandmother, and the number was etched into his memory. He cared about it so much that he offered to pay our phone bill himself, just to keep the number the same.
A free phone bill was a nice perk. Over time, it became a windfall.
A few of the guys were in long-distance relationships—some international. Phone use exploded. So did the bill. Eventually, the monthly phone charges exceeded the rent.
And still, the landlord paid.
He was losing money every month, not because the house wasn’t rentable, but because he couldn’t let go of something familiar.
It’s easy to see the mistake from the outside. But it raises a quieter, more uncomfortable question:
Where might we be doing the same thing?
Most of us carry at least one habit, belief, or pattern we’ve outgrown, but keep anyway. Not because it serves us, but because it’s familiar. Comfortable. Known.
Over time, the cost adds up.
Momentum slows.
Opportunities narrow.
Life becomes more expensive than it needs to be.
If you’re honest with yourself, where is your unwillingness to change costing you?
And if there were one change—just one—that would improve your life in the long run, what would it be?
Maybe it’s time to change the phone number.
WHEN THE PAST STILL LINGERS
This week I’m in Dallas, and I’m struck by how heavily history hangs over this city.
Dealey Plaza.
The X’s painted in the street marking where John F. Kennedy was struck.
The Sixth Floor Depository.
The theater where Lee Harvey Oswald was arrested.
The place where he had earlier killed Officer Tippit.
The Municipal Building where Jack Ruby ended Oswald's life.
Dealey Plaza, Dallas
Decades have passed, yet the past still looms.
And it made me think about how often we allow our own history to do the same.
Old failures.
Past mistakes.
Versions of ourselves we wish we could forget.
Unlike a city—where curiosity and remembrance will always keep certain chapters alive—we’re not required to live in our past. We’re allowed to turn the page. To begin again. To create distance between who we were and who we’re becoming.
So here’s the question I’m sitting with:
Where are you still lingering in the failures of your past?
And what might change if you decided—today—to write a new story?
THINGS WORTH THINKING ABOUT
The Difference Between a Successful Life and a Meaningful One
What if success isn’t the thing we should be chasing?
This short thought experiment reveals why a life can look good on paper—and still feel empty inside. A reflection on success, meaning, and the quieter question that determines whether a life truly feels worth living.
→ Read the full article
BEFORE YOU GO
Life is constantly inviting us to begin again—sometimes quietly, sometimes at a cost.
May you have the clarity to notice where change is needed, the courage to make it, and the wisdom to invest your days in what will still matter when you look back.
Stay inspired by the life you’re living.
Kevin
Jan 2, 2026 — Course Correction, Not Reinvention
A meaningful life isn’t built through dramatic reinvention. It’s shaped by small course corrections—made often—that slowly guide us toward the life we want.
Take Two
For people who know there’s more to life and don’t want to miss it.
COURSE CORRECTION, NOT REINVENTION
We often approach the New Year as if it requires a total overhaul of our lives. New habits. New goals. A new version of ourselves.
But meaningful change rarely happens that way.
Commercial airplanes offer a helpful reminder. After a plane takes off, it's slightly off course for much of the journey. What matters isn’t flawless precision—it’s the constant course corrections made along the way.
Small adjustments. Repeated often. That’s how a plane arrives where it intends to go.
Our lives work much the same way.
Most New Year’s goals fail not because we lack motivation in January, but because we don’t revisit them in February… or April… or October. We set a direction once and hope momentum will carry us the rest of the year. When life inevitably drifts us off course, we don’t notice—or we notice too late.
The alternative is simpler and far more effective.
Instead of asking, How can I reinvent myself this year?
Try asking, What small correction would bring me closer to the life I want to be living right now?
Improve your sleep.
Reduce screen time.
Watch less television and read more books—even a page or two each day.
Give more time and attention to your health, your relationships, your spiritual life.
Course correction doesn’t demand perfection. It requires awareness.
And the good news is this: you don’t have to wait until next January to begin again. You can recalibrate today. Tomorrow. As often as needed.
A meaningful life isn’t built through dramatic resolutions. It’s shaped through small, repeated adjustments.
What small adjustment can you take today that will help you move in the direction of the life you want to live?
THREE QUESTIONS TO CONSIDER
A New Year is an invitation to ask better questions—because the quality of our lives is often shaped more by the questions we ask than the goals we chase. Here are three worth sitting with as you begin the year:
1. Fast forward to December 31, 2026—what one thing would need to have happened for you to feel this was a good, meaningful year?
2. If you knew 2026 would be the last year of your life, how would you live differently than you did last year? What conversations would you want to have?
3. What routines, habits, or time-consuming activities are no longer serving you? Remove one that's not working and replace it with something that will help you create the life you want.
NEVER MISS THE CHANCE TO START AGAIN
A new year doesn’t magically change our lives—but it does offer something precious: the chance to begin again with more wisdom than before. I wrote a short article that explores the value in starting again. You can read it here.
QUOTES TO CONSIDER
Quote #1:
“You do not have to be the same person you were five minutes ago.”
— Alan Watts
Quote #2:
“The truth is each of us are only one or two decisions away from a more beautiful and winsome life.”
— Bob Goff
Quote #3:
“Although no one can go back and make a brand-new start, anyone can start from now and make a brand-new ending.”
— Carl Bard
BEFORE YOU GO
I hope the year ahead is filled with wonderful moments and memories you’ll carry with you for years to come.
Spend some time imagining what this year could bring—but remember, you don’t have to have the whole year figured out. You don’t need a flawless plan or perfect follow-through. You only need a direction, and the willingness to make small course corrections along the way.
If you’re looking for ideas and inspiration for living a more meaningful, purpose-filled year, I invite you to read my first book, A Life Worth Living. I wrote it as a reminder—to myself most of all—to live intentionally and to make the most of my one wild and precious life. I’m reading it again now, because I’ve learned I always need reminding to live the life I’ve imagined.
Stay inspired by the life you’re living.
Kevin