We had the good fortune of connecting with Roger Steele and we’ve shared our conversation below.

Hi Roger, we’d love to hear about how you approach risk and risk-taking
Risk has been the backbone of my professional progress. From the start of my professional career I’ve been in a deep search for passion, and the leaps it takes to monetize those passions can put you in very compromising positions. My first brush with risk came when quitting my job as a civil engineer to ambiguously pursue my understanding of entrepreneurship. I left the industry completely and used my savings in attempt to start multiple businesses (which I would now consider dreams and hustles). This failed miserably and I ended up in LA with my last few dollars before finding a break in the form of a golf marketing job in LA. That risk didn’t pay off in the short term, but long term it freed me from a capped, passionless path and gave me an opportunity to form key relationships around my new interests.

From there I began to grow as a creative entrepreneur and built a stable book of business serving some respectable clients. It was not my dream situation but I was much closer to where I wanted to be than where I started. When the pandemic happened in 2020 I lost all traction. Within a two week span I lost all of my income and I struggled with the harsh realities of my value to the business landscape. I realized that I was hungry and talented, but I wasn’t necessary, something my father had always warned me about. During those months of professional solitude I asked myself a lot of hard questions about who I am and the impact I truly wanted to have on the world, or maybe even just the people around me. What I realized was that I did have a fear of being my authentic self, sharing true elements of my story and my beliefs because I feared the judgement would leave me without opportunity. Yet, here I was, out of work without being outspoken and finally convincing myself that there was no better time than the present to be who I wanted to be. What did I have to lose? After all, they can’t kill you if you’re already dead.

My next risk is the one that made this story matter. I began using social media to express my personal creativity and perspectives on a variety of things. I unashamedly started to present ideas on issues that made a lot of people uncomfortable in a way that I hoped could help various groups of people to relate. The risk was being truly me, no matter what it cost, and I perceived that cost to be very high. I anticipated a loss of invitations, access, future work, etc. I expected people to no longer recognize me and be afraid or bothered by things they saw. I thought people would disapprove and that I would sit alone even as the world came back together. Sounds irrational, but I thought was laying it all on the line.

However, to my surprise, the risk was the reward. In taking those strides to be myself I freed myself. The weightlessness of authenticity is something I pray we all get to experience. Then, in finding my voice I found newer and bigger opportunities in the form or business ventures, brand deals, media and consulting opportunities, etc. All of this for living in truth, and it’s been the most amazing year and a half of my life.

My takeaway is, sometimes the biggest risks we need to take are the obvious ones and they all center around being true to yourself. Risk is a very personal matter that requires a deep amount of self awareness to both identify and assess. And my message to any and everyone is, “If you’re ever contemplating a risk that rewards you with the opportunity to be a truly better version of you, that’s no longer a risk… that’s a necessity. Go get it.”

Alright, so let’s move onto what keeps you busy professionally?
My art is storytelling. I share accounts and ideas and offer perspective on things in a way I haven’t personally encountered in golf. Especially coming from someone that looks like me.

In a world full of creatives I think the thing that sets me apart is my ability to consolidate views. I’ve accepted the grey areas that are our feelings and opinions, and I present ideas that acknowledge but challenge all types of people. But ultimately my art is telling this ongoing story of glorifying purpose and process from a place of authenticity and humility.

The only challenges have been staying the course and doing what’s right/true vs what you can convince yourself is right/true. I think we all know the difference. The only thing I want the world to know is that there is room for us to be ourselves and that the highest versions of self can truly move mountains.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
In Chicago…. You gotta play golf with me.

Ravisloe CC for Golf in the AM
Au Cheval for Lunch (best burger in Chicago)
Nap
Hit Michigan Ave to kick it
Five Iron Golf for drinks and vibes
Then Steak 48 for dinner
Then you can find a lease and move here.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
My Parents. My Dad gave me skills. My Mother gave me perspective. I’m afraid of how life could have turned out growing up where I grew up without humans like them helping me navigate it.

Website: HIPEmedia.com

Instagram: @roger_steele

Twitter: @rogersteelejr

Image Credits
Arielle Gallione

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