The Obstacle is the Way

Fellow steward,

I was crying in my mom's arms at midnight on our front porch in the early 2000s as a senior in high school.

Everyone was asleep. No one could hear me except my mom.

Have you ever had a moment where you take your armor completely off?

(That's what makes a mom so special. You can just be you.)

I was in despair. I had tried so hard. I couldn't see past the moment. I was zoomed in to this very moment.

I felt my future was sunk. I was a failure.

Here's what happened:

I "failed" my SAT for the third time. 

(Looking back it’s a silly problem, but in the moment it was everything.)

It was only a semester left before college started in the fall. I'd given everything for months to crush the test. I didn't hit the mark.

I was convinced I'd be labeled a failure for the rest of my life.

I was convinced I'd amount to nothing because I couldn't fill in the correct circles on a scantron with a No. 2 pencil.

I studied. I took courses. I read SAT books. I had all the strategies.

I flopped. Multiple times.

Maximum effort. Nowhere close to winning.

I was at a loss.

Then my future mother-in-law made a suggestion: reach out to an esteemed alum of the college for coffee. She pointed to the lady on the cover of the university magazine who happened to live in my hometown on the kitchen counter.

I found the alum’s phone number in the phone book. (I sound old now.) I called and set up coffee.

Just after the new year, before college decisions were made, I met her. Dressed up. Resume in a folder with my name on it. Eye contact. Real conversation. I bought her coffee. I drank hot chocolate.

We talked. I shared my goal to attend her alma mater. I sent a handwritten note that day.

Four weeks later: ACCEPTED.

Despite my SAT score that should have prevented me from entering through the front door.

I felt helpless weeks before that acceptance letter. If I'd succeeded on the SAT, I'm not sure I'd be the person I am today.

Life has a sense of humor when teaching lessons.

Take action. Take forward steps even when you are down in the dumps. I picked up the phone.

The power of a handwritten note.

Relationships run the world. (Prioritize this truth accordingly.)

Don't stand in line at the front door to be picked.

Most importantly, I have these two beautiful moments from the hardship:

My mom caring for me when I felt vulnerable.

My mother-in-law believing in me and nudging me forward. 

Hard moments suck. 

Hard moments will come in your family business in 2026. (So will breakthroughs in 2026.)

Hard moments ask us to be a better version of ourselves.

Hard moments make us appreciate who we're walking alongside. 

Hard moments made Bill Walsh the legendary coach he is today. 

Oprah would affirm: “Failure is just that thing trying to move you in another direction. The losses are there to wake you up.”

As much as I don't want to admit it: the obstacle is the way. 

That’s the galvanized mindset of a steward. 

Onward,

Matt