Head in the Clouds, Feet in the Dirt

Brent Osborne
3 min readDec 27, 2019

I dig this time of year — the coziness, the smell of pine, the gatherings with glorious amounts of food, and of course, the deep conversations and reflections about life.

This year has been promising — covering the full range of emotions. My work life, side projects, graduate school, and my personal life are all intersecting in what seems to be a beautiful venn-diagram.

Unsurprisingly, the things I didn’t plan for this year brought me the greatest sense of fulfillment. I was able to really focus on what I know, on my passions. It’s made me more humble. Likewise, more responsible, more cautious and even more ambitious.

It’s no secret that I am a massive fan of Gary Vaynerchuk. I love his entrepreneurial style and courageous attitude. He’s been an inspiration for me as a visionary and practitioner.

Gary has this beautiful metaphorical philosophy — Clouds & Dirt.

The clouds are a metaphor for strategy. They’re the high-end beliefs that are at the heart of everything we do, everything we want.

The dirt is the low-down subject-matter expertise that allows us to execute to reach those clouds. The dirt is about the hard work we need to put in.

The idea here is to simply understand the “why” that is up in the clouds, and then be obnoxiously proficient at the “how” that is down in the dirt. It’s the two ingredients needed to win — raise the bar on philosophies and dig deeper into the craft.

Every new chapter in life gives way for new clouds & new dirt. I’m turned on and tuned up for 2020. Here. We. Go. 🚀

May the next decade be full of unapologetic success, unparalleled growth, heaping amounts of love, and radical inspiration for all.

P.S. — Life is not a single player game and I know that I am standing on the shoulders of giants. Thank you to my tribe— my family, friends, mentors, coworkers, peers — for making this year, and the decade to come, spectacular.

Mantras from Years Past

Make Your Life a Story Worth Telling
At the end of our journey, all of our possessions will fade away, but the strength of our legacy and the story of our life will remain.

Get Outside of Your Comfort Zone
When you go beyond the places that make you feel safe, you enable yourself to truly discover who you are and what makes you feel most alive.

Don’t Schvitz The Small Stuff
The people with the brightest minds and the biggest hearts choose to see the world in a powerful, positive perspective. That is what paves the way to create a massive impact.

Find the Funny
Life is literally abound in comedy. Perspective changes when you vow to actively seek humor in the everyday.

Run the Risk
When you push through the fear of failure, exhilaration lies on the other side.

Trade Expectations for Appreciation
Accepting others for who they are and not who we wish them to be leads to authentic emotional independence.

Be Where Your Feet Are
Prosperity lies within the balance of living in the moment and planning for the future. Embrace the now.

Pitch a Perfect Game
True progress doesn’t come from striving toward results… it comes from improvements in process.