My guest today, Brett Henley and I start off the show by talking about a new creative mecca that goes by the name of Nashville, TN. I’m really curious about its creative, tech, and food culture, and why so many people I talk to lately seem to be moving there. And Brett has quite a bit to say about this grand old city everyone is moving to.
Here we discuss Brett’s own story, what he was like as an introverted kid fully immersed in geek culture, and his honest account of his meandering, sometimes painful, journey.
Brett has a background in digital strategy, so I naturally ask him about that fun world, what led him there, and how he ended up in the creative space. So we talk about his start in digital media around 2006, how he spent a fairly long time in the agency world, which slowly, but surely led to where he is today. This leads to a discussion of the portfolio life and why this is such a great time for those renaissance men and woman with a variety of skills to break out in their own way.
Hey Instigator and Brett’s consulting process
We then take a deep dive into branding, including Brett’s methodology for bringing a brand to life. We talk about what Brett is doing today, including his property, Hey Instigator. How his new work is centered on creative entrepreneurship and “combining creative services and a gentle kick in the ass.” And, based on that statement, I ask him to run through a typical client call and how he addresses a client’s biggest challenges. He often starts the process by taking a journalistic approach that is both personal and painfully honest. Brett works with clients to help them articulate their brand by going beyond standard branding “best practices.” His approach is not just about their skills, but their personality and how that impacts their business.
The entrepreneurial struggle and how to be profitably creative.
A recurring theme in this show is the entrepreneurial struggle and one of my favorite topics—combining self-awareness and creativity. So, we talk through this topic and why many in the online realm think there’s a magic solution to help them rise from obscurity to notoriety. And why many get stuck playing this comparison game.
The clear problem is that “success” is so subjective, so there is obviously no boiler plate solution. Not to mention, building a successful online platform is really hard, and it’s not always about hustling more than the other guy… it’s more about finding your unique place and doing things that fit with your style, your temperament, your level of creativity, and built around those you truly want to work with. This leads to a discussion of Maisie Smith’s “Rocking the Small Corners” post, and the idea of changing the world in your own little way.
We even discuss social media, but the focus of this show is about what is means to be a creative entrepreneur in this day and age… How does self-awareness fit it? What about visibility vs. simply loving the craft? How does one go from bootstrap to sustainable? And how do we squash those built-in notions that somehow if we are not “making it”—living up to entrepreneurial standard and hustling at all costs—we are not worth it?
And I ask him at the very end: What does “showing up” mean to you? I love his answer and think the entire interview is well worth the listen, ESPECIALLY if you are a struggling creative entrepreneur.
Questions I ask:
- How did you find your way into digital strategy?
- What are your clients’ biggest challenges? What is a typical coaching call like?
- What are habits that keep you on track?
- What is your Why? What lights you up?
- What was the major reason for shutting down your podcast?
- How does one go from bootstrap to sustainable?
- Can success and self worth fit together?
What you will learn:
- The painful process of fleshing out a brand that truly represents you. (The best branding processes often have an element of pain.)
- Why his branding process is like creative therapy.
- You don’t need a massive platform to be successful 🙂
- Your body of work is a lifetime process (a marathon).
- The myth of the overnight sensation.
Links mentioned in the show:
- Maisie Smith: Rocking the small corners.
- Danielle Laport
- AJ Leon and Misfit Inc.
- Portfolio Life podcast Jeff Goins
- Unmistakable Creative podcast Srinivas Rao
- The Antidote: Happiness for People Who Can’t Stand Positive Thinking by Oliver Burkeman
- Brett Henley on Twitter
- Hey Instigator Brett’s Business
Want to find out why I started the Art of Breaking Out podcast? Read this.
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