ISSUE #012| THE LEADERSHIP CONTRARIAN
As I write this, I’m sitting in a small Airbnb in San Francisco.
Not because I’m on vacation.
I’m here because my sister has brain cancer.
Last week she began a six-week protocol of daily radiation treatments here in the city. It’s all still very new for our family, and we’re learning the rhythm of this journey one day at a time.
Her plan was simple. She and her husband decided she would live here in San Francisco for the entire six weeks so she could receive treatment each morning without the 4 hour drive from home. She asked our 82-year-old mom to stay with her during that time (she's a spitfire and still going strong).
And then she asked friends and family if a few of us might volunteer to come down for one week each to help support her along the way, especially since she’s not allowed to drive right now.
I immediately volunteered.
Which she initially resisted.
Not because she didn’t want me here, but because she knows how busy I am running two companies and serving our clients. She just didn't want to be a bother.
This is exactly why we chose to build our businesses the way we have.
For years I’ve been intentional about designing our companies so that life’s important moments can take priority - both for me and for the people who work with us. Moments like this one. Because when your sister is facing brain cancer, the decision to spend a week with her shouldn’t feel like a sacrifice.
It should feel like a privilege.
And for me, at 58 years old, it truly is.
Each morning we wake up, drive across the city, and walk into the hospital for Dana’s radiation treatment. Then we step back out into the sunlight and try to make the most of the hours we have together. Some days we explore a neighborhood. Some days we find a small restaurant and sit a little longer than we normally would. Some days we simply walk and talk until Dana’s energy runs out and we head back to the flat so she can rest and prepare to do it all again tomorrow.
Being here has given me time to reflect on something important.
Three observations this week have reminded me why I became an entrepreneur in the first place - and why the way we design our businesses matters more than we sometimes realize.
My mom is 82 years old. She recently retired at 80, although “retired” might not be the right word. She still finds little projects and side jobs because she enjoys staying active and contributing.
In the evenings the three of us sit together and tell stories. Stories from forty and fifty years ago. Stories from when we were kids, from high school, and from raising families and building lives.
Listening to the three of us talk reminds me how a lifetime is really built.
Not in big dramatic moments, but in thousands of small ones that accumulate over time.
The same is true in leadership.
Great companies are not built overnight. They are built slowly; through daily decisions, values lived out over years, and relationships that grow stronger through consistency and care.
The future we hope for, whether in life or business, is being built in the choices we make today.
My sister Dana is 55 years old.
This is her second battle with cancer, and she also lives with MS. Yet if you spent time with her this week, you might never guess the weight she’s carrying.
Every morning we go to the hospital for radiation. Every afternoon she insists that we get out and walk. One day we explored Golden Gate Park. Some days we wander a neighborhood and find a place to eat. Some days we head out to explore another corner of the city together; her doctors told her exercise is her best weapon against the fatigue from treatment.
But what stands out the most is her attitude.
The other day she told me she plans to live another 43 years. I asked her where that number came from.
She said, “That would put me at 98 like Grandpa.”
She said it with a smile and complete confidence. It seems to me she’s setting a goal she can work toward, and that’s healthy.
Now none of us truly know how long we’ll live, but hope is powerful. Hope gives people energy. Hope gives people courage. Hope allows people to move forward even when life feels uncertain.
This week I’ve watched my sister encourage nurses, doctors, and even other patients in the hospital. It’s a reminder that leadership isn’t always about authority.
Sometimes leadership is simply the spirit you bring into the room.
During this journey Dana met a young woman in the hospital. She’s 28 years old and has been battling brain cancer since she was 15. They’re beginning to have the kinds of conversations families have when the end of life may be approaching.
This week Dana went up to visit her and her mother on the 14th floor. She's gone back every day this week.
First she goes to her radiation treatment then she stops in to encourage the young woman and her mom. Even with what my sister is going through herself she has an attitude of seeing others and helping where she can.
It’s sobering.
My own daughter is 30. My niece is 29.
Standing there hearing about this young woman’s story puts life into perspective very quickly.
This week I’ve found myself looking at life through three very different lenses. When you stand in the middle of them at the same time, the perspective is hard to ignore:
When you see life through those three perspectives at the same time, something becomes very clear.
Time is the most valuable asset any of us have.
And that brings me back to the question I started with.
What are you building your business for?
One of the reasons I chose to build my own companies was so I could make decisions like the one I made this week - to step away, to be present, and to sit with my sister during a moment that matters.
Money matters. Success matters. Building something meaningful matters.
But none of those things mean much if we build businesses that prevent us from showing up when life calls.
This week in San Francisco has reminded me of something I never want to forget. At the end of our lives, people won’t remember our quarterly numbers, our titles, or the deals we closed.
History records about what people did.
But people remember how others made them feel.
When I look back on this week someday, I won’t remember the meetings I postponed or the emails that waited. I’ll remember sitting with my sister. I’ll remember my mom telling stories from decades ago. I’ll remember the laughter, the quiet conversations, and the privilege of being present during a moment that mattered.
So I’ll leave you with the same question I’ve been asking myself this week:
What are you building your business for?
If any part of this resonated with you,
even a sentence,
Would you send me an email and tell me?
I really value your feedback and it tells me if I’m making a difference or if I need to course correct.
Until next time,
Keep learning.
Keep growing.
And God bless,
- Michael