59. Making Work Suck Less with TJ Bennett

What if work didn’t have to feel so…sucky? TJ Bennett is on a mission to help people figure that out. We talk about his DesuckifyWork® podcast, his path through advertising, the pressure we put on ourselves to have everything figured out (even though none of us do), and what actually makes work…and life…feel better. A fun and honest conversation about how things actually unfold. TJ didn’t have some perfectly mapped-out plan. He followed what was interesting, paid attention to what felt off, and made changes along the way. From randomly discovering advertising…to realizing later in his career that something had shifted…to leaving a successful career to try something new without knowing exactly how it would all work. We also talk about how early experiences shape the way we see work and life, and how sometimes it takes something significant to make us pause and rethink what actually matters. And throughout the conversation, this idea keeps coming up: We think we need to know first…and then act. But most of the time, it’s actually the opposite. We try something. We figure it out as we go. We adjust. That’s the process. It’s simple. Not always easy. But much truer than the story most of us are carrying.

We Talk About:

• The unexpected path that led TJ into advertising (and how one seemingly random moment can change everything)
• Why not knowing how is usually the thing keeping us stuck
• How a major health experience early in life shifted how he thinks about work and what actually matters
• The moment “Desuckify” became a thing…and why he committed before he had it all figured out
• Why “fine” can be dangerous
• The pressure we all feel to have it figured out (and the fact that none of us actually do)
• Why enjoyment might be one of the most underrated tools we have

About TJ Bennett

TJ is the founder, CEO and executive coach at The Pudding Factory, a work desuckifying consultancy.

He began his coaching career after 25 years as an advertising executive, creative director and writer for agencies big and small., including TBWA\Chiat\Day, Saatchi & Saatchi, Ogilvy and Hill Holliday. He helped Fortune 500 clients like Verizon, Toyota, MetLife and Panasonic sift through the noise to solve big creative challenges. And he helped his teams do the same. His mission is to DesuckifyWork®. And he hosts a popular podcast with the same name. His cat Carl offers this review: “less talking, more treats dude." As an ICF-certified executive coach, TJ helps leaders and brands find calm in the chaos and grow what matters. Ready to make sense of the muck? Talk to TJ. Here’s where you can find TJ…

• Website: https://www.thepuddingfactory.net/

• LinkedIn: https://www.linkedin.com/in/teejaybee/

• Substack: https://tjbennett.substack.com/

And here’s where you can find me…

• Learn more about working with me at The DASH Mindset.
• Connect with me on LinkedIn.
• Have an idea for a future episode? I’d love to hear it!

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