October 6th, 2025

What if you tried to fail more often?

Steven Barlett hosts the largest podcast in the world right now, Diary Of A CEO.

They have 50 million monthly listeners,

Nearly 13 million subscribers on YouTube,

And they've recorded over 720 episodes featuring some of the biggest stars and businesspeople around today.

And he was recently the surprise guest at Press Publish NYC, a marketing and creative event in New York that happened the other week. I wasn't able to attend the conference live, but I was listening to the recording of Steven's talk this week, and one thing really stuck with me:

Steven has a failure team.

Led by someone with the literal job title of "Head of Failure", this team works across his business to run experiments that give them the information they need to make a positive change. In Steven's words:

"Failure equals feedback. Feedback equals knowledge. And knowledge equals power."

Now, as a media business that employs dozens, this makes a ton of sense for him. But take a moment to think about how you could run more experiments in your career or business, to fail (and learn) more often?

• At work, could you shadow a different team to possibly stumble through their industry but learn more about how the business really runs?
• Is there a trusted coworker you could share a rough concept for a new initiative at work you want to start, instead of spending more time making the perfect pitch deck?
• If you're a creator, what new formats could you test? Have you tried making a vlog, carousel, or video, knowing that any of them could flop?
• Is there someone in your niche (or outside of it) that you could collaborate with? You may lose engagement in the short-term, but find a brand new audience that values your perspective

One other powerful thing Steven mentioned is that his Head of Failure is judged on how often she fails, not how often she succeeds. Because even at his level, he knows that he needs to incentivise the people he works with to take the shot, even if it may not land.

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Welcome to First Things First, Reader. I created this newsletter as the reminder I needed to reflect on how far I've come, as well as prepare for the journey ahead.

Today I'll share with you:

• Why the last video you saw on TikTok was probably fake
• Why Gen Z feels uniquely stuck at work (and what to do about it)
• What I learned at CultureCon this weekend

I’m so glad you’re here. Let's get started.

New AI video tools push the boundary of realism. Here's what you need to know:

Late last week, OpenAI, the makers of ChatGPT, announced an AI-only social media app, Sora. And it only took about a day for it to become the #1 app on the app store, with thousands of surprisingly convincing AI-generated videos making their way onto TikTok and other social media platforms:

The subway love story video that racked up 35M views and had TikTok convinced

Clips of Michael Jackson rap battling Robin Williams, or.. stealing chicken nuggets​

A CCTV-style video of OpenAI CEO Sam Altman stealing computer parts (I'm sure fake secruity cam footage will only be used for good)

Access to Sora is still being limited via special access codes, but the demand is clearly there for people to start creating AI videos of their own. Though I imagine OpenAI is intentionally limiting access to manage load on their servers, and get ahead of any bugs (and intellectual property claims) before rolling this out to a wider audience.

As someone who makes a living from creating videos on the internet, I'll be watching this very closely. But if I'm being honest, I'm not too worried. Beyond the entertainment value of a SpongeBob x Breaking Bad mashup, I still believe that trust and relatability are the actual currency of content, and you can't replicate that just yet.

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How to cut through the noise in a broken job market

When I think of Gen Z as it relates to the job market, the one word that comes to mind is empathy. I feel like they spent their entire early lives preparing to build a career and life in the world that exsisted for their parents and older siblings.

Not realizing that by the time they graduated college and looked to enter the job market, they would be competing for opportunities with the most sophisticated piece of technology we've ever designed.

So when I had the opportunity to speak with SUCCESS Magazine this past summer to share my top tips for standing out in this broken job market, I felt that I had an obligation to bring my A-game.

You can read about my tips and the other strategies shared by checking out the full article here.

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CultureCon was one of the events I've been to this year

This Sunday, I attended CultureCon, a 2-day creative festival in Brooklyn. Let's talk about it.

While it was a great opportunity to see the creative energy and community in NYC, I can't say that I was overly impressed by the content of the day or the networking opportunities provided by the event.

At other conferences I've been to that do this well, they always have specific ways to engage with the speaker sessions (and attendees) that relate to your industry or interests, like a special speaker track, or themed networking areas.

But that wasn't really the case here. The VIP section looked more like a club than an exclusive networking opportunity (though I only had general admission tickets so I do recognize I am literally hating from outside the club, and there weren't even nametags, so it was tough to start a conversation in the first place.

Some of my friends, like Cinneah and Calum Johnson, took to the stage to talk about moving smarter with money and how AI and creativity can work together. Two topics I'll always be interested in. But if I'm being honest the rest of the event felt more like a fashion show than a conference. But maybe that's the point, IDK.

The merch was great, though!

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A few resources to help you on your journey

Career Wrapped: We already know you listened to a lot of Drake this year. Instead of a Spotify Wrapped, why not create a "Career Wrapped" for this year instead?

Download for free!

LinkedIn Search Secrets: Most people have no idea how to take full advantage of LinkedIn to find jobs or people to network with in their industry. Here's your guide.

Download for free!

One Pager: This promotion template got me promoted twice in two years. This will help you summarize your skills and drive your yearly review conversations at work!

Download!

I've spent the last few years creating and collecting the best resources to help you level up in your life and career. Check out my most popular ones above, or view the full list here.

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Reader

It really means the world to me that you show up to explore these topics with me each week, so thank you for reading. If something above resonated with you, consider sharing it with someone else who might need it too.

If you have any feedback, you can always reply or email me at me@colinrocker.com

And remember that you’re not behind, because you're a "first". Which means you were never made to follow.

Chat soon,

-Colin

Colin Rocker Career Educator & Founder ​Instagram | LinkedIn​

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