On my way from Freeport to the Portland Jetport this week, my Uber driver and I started talking. When he learned we had a place in Bozeman, he asked if we were Yellowstone fans. That turned into a conversation about Outlaw Brewing, TV series, business, success, and life. All the things that I love to write about.
As we pulled up to the airport, he said:
“Man, I wish you had been my Dad. I would have done so much better.”
That’s one of the best compliments I’ve ever received. It’s also why I write. Like Rick Rubin writes in The Creative Act: “In terms of priority, inspiration comes first. You come next. The audience comes last.” But every now and then you meet a member of your audience face-to-face, and it fires you up to reach further.
As he unloaded our bags, he looked at me asked a question that really matters. It implies a willingness to take action now. A key ingredient for success.
Action, you know how I feel about movement and forward momentum.
Here’s the question: “What should I do first?”
That’s not wishful thinking. That’s action. And my answer was simple:
- Get control of your money.
- Believe in yourself.
I didn’t actually tell him “Believe in yourself.” but I realized when I was in the luggage line that I should have.
Why money first? Because once you get momentum, belief follows.
I know this firsthand. Years ago, I was in debt with little savings. I discovered Dave Ramsey and while I don’t agree with everything he teaches, his envelope system gave me structure. Dave’s cash-based method didn’t stick for me long — I’m more of a digital guy. So I built my own version: a digital envelope system that still guides my spending today.
Another technique I implemented was to create allocations for family members. That one simple change made a huge difference in my marriage. I wrote about it in my slice the pie post.
In Summary
Before chasing big goals, start small. Learning to master your money isn’t complicated—but it is life-changing. These simple technique brought me balance, trust, and lasting confidence, and they can do the same for you.



