What I’m Learning About Success, Seasons, and Staying the Course
Reflecting on Life, Leadership, and What Really Matters
As I move deeper into both life and leadership, I find myself returning to the same essential questions:
What does success actually mean to me?
What does it look like to live that out day by day—especially when the path isn’t straight?
And how can we align our actions with our values, even in the face of uncertainty?
These questions guide not only my personal journey but also my work as a coach and speaker. Over time, I’ve learned that while answers evolve, the values that ground us can serve as true north.
1. It’s Good to Share in Each Other’s Businesses
My wife and I are both entrepreneurs. That alone brings a healthy mix of excitement, unpredictability, and growth.
In a marriage—or any close relationship—it’s impossible not to be affected by your partner’s highs and lows. For us, this interconnectedness is a gift. We support each other, share wins, and troubleshoot together.
But we’ve learned that kind of support takes intentionality. Being present, communicative, and willing to wear multiple hats—partner, coach, cheerleader, and listener—is how we make it work.
2. There Are Seasons for Everyone and Everything
One of the biggest truths I’ve embraced is this: You can’t do everything all the time.
There are seasons when certain dreams go dormant. When grief takes the front seat. When family, rest, or recovery becomes the priority.
That doesn’t mean failure—it means life.
The key is stewardship. If we show up with care, even in the quiet or messy seasons, we plant seeds that can flourish later.
🌱 Just because we can’t see something happening doesn’t mean growth isn’t taking place.
3. Happiness Is a Series of Choices
Happiness doesn’t arrive fully formed. It shows up in daily choices:
What thoughts we entertain
What boundaries we uphold
What energy we bring to each situation
One of my favorite quotes is from Chuck Swindoll:
“Life is 10% what happens to you and 90% how you react.”
I’d take it even further. The quality of our life depends not just on our reactions—but on our responses. What do we choose to pursue, release, or reframe?
When we take ownership of our joy, we reclaim agency—regardless of our circumstances.
4. Staying the Course (Even When It’s Hard)
My wife and I have a shared commitment: Stay the course unless clarity or consistent redirection tells us otherwise.
This doesn’t mean we avoid change. We pause. We ask questions. We adjust. But we don’t quit at the first sign of friction.
Sometimes staying still is the most radical act in a world addicted to motion.
Like the crops buried in soil, some of the most important growth happens underground, invisible. But it's still real. And worth trusting.
5. The Power of Defining Success
If we don’t define success for ourselves, we’ll end up living out someone else’s version.
And the truth is, not all definitions of success are aligned with health, wholeness, or joy.
My mom once told me something that stuck:
“The more powerful your ‘no’ is, the greater the impact of your ‘yes.’”
When we’re clear on what we stand for—what we’re unwilling to compromise—we can give our best energy to what truly matters.
🔑 Define success. Then align your calendar, your relationships, and your dreams around it.
What This Looks Like in Practice
At Dreaming Made Simple, I help individuals and teams reconnect with their purpose—especially after hardship or major life change.
Whether they’re grieving a loved one, navigating disability, or just feeling stuck, my clients are searching for clarity, momentum, and meaning.
I tell them what I tell myself:
You can move forward intentionally, even in uncertainty.
You don’t have to go through the motions.
And you’re not behind.
A Few Questions for You
What season are you currently in?
How do you define success for yourself?
What’s one intentional choice you can make today that moves you closer to that vision?
Leave a comment below—I’d love to hear from you. 👇
Let’s Connect
If this post resonated with you, let’s keep the conversation going.
You can find more of my writing and resources at Dreaming Made Simple, or reach out directly for coaching, speaking, or collaborations.
Sam Miller
Founder, Speaker, Coach, and Author of I’MPOSSIBLE JOURNEY: Finding Treasure in the Midst of Grief