It’s a beautiful Sunday night in Indiana (or Monday for some of our brilliant subscribers halfway around the world). I’m happy you decided to spend a few minutes reading my head trash. 🙂 Here’s what’s in today’s diary entry:

• Personal: The Friendship Paradox: Why We Struggle to Make the Time

• Work: After 12 Years, Content Marketing Hasn’t Changed

• Work: On Reimagining Marketing Team Structures in an AI World

Enjoy.

Thanks to Share Your Genius, who is our first partner in the newsletter and podcast. I’ve known the team and their CEO for years. They are the best creative agency, helping brands build deeper relationships with their audience through binge-worthy podcasts and great content.

The Friendship Paradox: Why We Struggle to Make Time for the People Who Matter Most

This morning, I grabbed coffee with a good friend, a guy who stood next to me as my best man in my wedding and one of my best friends throughout college. He lives just half a mile away, yet we only see each other two or three times a year. It’s not because we don’t care or don’t want to hang out. Life just gets in the way. Work, kids, the revolving door calendar. The weeks turn into months, and before we know it, another six months have passed with nothing but a few “Are you available on Monday?” texts.

It just gets more difficult as you age, especially when much of your social life revolves around “getting a beer” or a “weekend out bar hopping.” 

As for me and my friend, most of the time we spent together revolved around drinking. Meeting up for beers, hanging out at bars, going out with friends. But now that I’ve cut the giggle juice, the liquid courage, those default plans don’t work anymore. 

And without them, I’ve realized something… if you’re not intentional about your friendships, if you don’t actively make the time, those relationships fade, no matter how much history you have.

Here’s the hard truth… 

Mark Manson puts it bluntly: “Making friends as an adult is weird.” In his article How to Make Friends as an Adult (a favorite of mine for the last year), he outlines three deeper challenges that make our friendships difficult:

1. Time Constraints – As kids, friendships happen naturally because we spend hours together at school, in sports, or on campus. As adults, our schedules are packed. Work, family, and personal responsibilities come first, and socializing gets whatever time is left over (ie, not much). 

2. Fear of Rejection – When we were younger, it was easy to ask, “Hey, want to hang out?” without much thought. As adults, there’s more hesitation. We worry about looking desperate, being rejected, or imposing on someone else’s time. So we don’t reach out.
   

3. Lack of Proximity – Friendships thrive on convenience. In college, your best friends live down the hall (like my friend). At your first job, you grab lunch with coworkers every day. But as you get older, people move, change jobs, and drift apart. Without built-in proximity, keeping up requires effort, and most people aren’t great at putting in that effort.

You have to make the choice. 

The New York Post recently called friendship the “ultimate biohack,” citing research that strong social connections can reduce stress and even help you live longer. But friendships don’t survive on nostalgia alone. If you want to keep people in your life, you have to be intentional.

You have to be deliberate. 

For me, that means redefining what friendship looks like. Instead of defaulting to the easy, built-in ways we used to hang out (which often involved drinking), I have to be deliberate. Morning coffee instead of late-night beers as an example.

The hardest part isn’t making the time. It’s admitting that, at this stage of life, friendship is a choice. And if you’re not choosing to prioritize the people who matter, you’re choosing to let those relationships slip away.

So, if there’s someone you’ve been meaning to see, send the text. Set the date. Be deliberate. Because the friendships that last aren’t the ones that happen by accident. 

They’re the ones we make space for.

As for my friend, we’ve decided to schedule coffee once a month for the foreseeable future. It’s a small change, but it’s a start because friendships don’t keep themselves alive. 

You have to show up.

❤️ Kyle

It’s Been 12 Years, and Content Marketing Hasn’t Changed

Content marketing has remained unchanged since I built my first team and content strategy in 2012. It's wild, and I have the evidence to prove it.

I was lucky to be part of ExactTarget early on in my career, not only because of the company's IPO and acquisition by Salesforce but also because of the career development opportunities it afforded us.

Over those 2.5 years, I had the opportunity to travel the world, speak at 250+ conferences, and build a global content marketing team from scratch out of Indianapolis.

I found the original pitch and budget document I used to sell the building of a content marketing team to our CMO. Enjoy Kyle’s Head Circa 2012.

The Problem: There’s a disconnect between who manages the creation and activation of content based on thought leadership, research, trends, news, and digital information that informs and educates. Other problems include:

• No Centralized portal or repository for content (both internal and external

• Ownership and scalability of content activation and creation

• Communication between content owners

• Consistent measurement and reporting (monthly and quarterly)

The Content will be based on the company's global, channel, and vertical needs, as established by the Leadership team.

• Strategic – What should the marketing professional do in the email, social, mobile, and digital space? (trends, best practices, design, case study, SFF research, and partner whitepapers)

• Technological – How does the marketer use technology to accomplish goals? (product, case study, white papers)

• Company – How does ExactTarget live ORANGE? (video of events, employee interviews, pictures of service projects)

•  Industry – Late breaking news and other software news

The Solution: A content marketing team and hub should be implemented to manage the strategy, activation, and distribution of content to the public.

1. A Content Marketing team responsible for the creation, activation, and measurement of content

2. Building a content hub that separates, stores, and distributes information based on brand, vertical, channel, and strategy

Measurement: The Content Team is measured by continually improving customer nurturing and retention and lead increases. Success criteria include:

• Increase in Lead/Oppty Generation

• Increase in defined customer engagement metrics

• Website and social media traffic growth

• Customer feedback and survey data

• Increases in key search engine rankings

Are there adjustments I would make based on the last 12 years of experience and the changes in our profession? Of course.

The bottom line? While the tools and platforms have evolved, the fundamentals remain unchanged. You still need quality content to build trust and revenue.

On Reimagining Marketing Teams in the AI Revolution

I've been thinking obsessively about team building lately. Not because I want to, but because I have to. The AI revolution (or renaissance if you will) we are currently experiencing will change how we think about building teams completely.

Every morning, I wake up, grab my coffee, and discover another AI tool or tip that can potentially change how I approach work and life. What used to take hours now takes minutes. What used to require a team of three now needs just one person with the right prompts.

It's exhilarating and damn terrifying all at once.

So, as one does when exhilarated and terrified, I started to piece together my thoughts about building marketing teams in this new world. Not because I have all the answers (I definitely don't), but because waiting is a luxury none of us can afford anymore.

Test. Experiment. Iterate. Learn.

The Great Marketing Reshuffle

Here's what I know for certain: AI-powered marketing tools are completely reshaping team structures. Tasks that once formed the backbone of junior positions (content production, data analysis, campaign optimization, and planning) are being quickly automated. Can you feel the tension in the room? I can.

Do we double down on experienced professionals who can immediately leverage AI tools to drive results? Or do we invest in junior talent and build robust training programs to develop an AI-fluent pipeline for the future?

The path of least resistance is clear. When faced with pressure to deliver results, most marketing leaders will opt for seasoned professionals who can hit the ground running with AI tools. I've caught myself making this same calculation.

But this creates what I'm calling the AI-Driven Career Bottleneck…

If entry-level marketing positions are automated away, where do tomorrow's marketing leaders learn? How do they develop the skills and judgment that AI has yet to replace?

Because we have a dilemma…

I've been fascinated by Lawrence Jones' thoughts on what he calls the “AI Innovator's Dilemma." His findings confirm what I've observed in my day-to-day… AI is giving smaller, more agile teams a significant advantage over larger organizations bogged down by scope creep, legacy rot (sounds delicious, right?), and slow decision-making.

A five-person marketing team with the right AI tools can now produce what once required 15 people and twice the budget. But only if they're structured for speed and continuous-rapid improvement.

This perfectly illustrates what Jones discovered in his research: larger organizations often struggle with AI adoption because of slower decision-making processes and legacy rot, while smaller, more nimble teams can adapt and implement AI with speed and efficiency.

Four Critical Challenges for Marketing Leaders

After dozens of conversations and therapy sessions with peers, there are clearly plenty challenges we are facing, but I’m going to focus on four for tonight:

Resource Allocation: Efficiency vs. Scalability

Companies are chasing senior marketers who can immediately leverage AI, scoring quick wins. But this short-term hustle comes at a cost. It’s a hiring model that isn’t built to grow. Relying too heavily on senior talent today can choke off the ability to scale teams, balance workloads, and keep grinding over the long term.

AI is Reshaping Entry-Level Marketing Roles

With AI taking over routine marketing tasks, the traditional learning environment for junior marketers is rapidly shrinking. The opportunity to hone foundational skills is fading, and without a solid training framework, our industry risks facing a mid-career talent drought.

The Risk of Over-Reliance on Familiar Thinking

When hiring decisions lean too heavily on experience, there’s a danger of falling into predictable patterns. This can lead to teams playing it safe, which is a death blow for marketing teams. The strongest teams combine deep expertise with fresh creativity to break the mold.

Structuring Teams for Sustainable Growth

As AI redefines our work, marketing leaders must reimagine career pathing and development. The old “learn on the job” model is giving way to more structured, forward-thinking paths. Companies that evolve by integrating AI-first training and enablement into every stage of career progression are paving the way for tomorrow’s leaders.

Overwhelmed yet? We haven’t even truly begun.

Understanding the challenges is only half the battle. In next week’s edition, we’ll dive into actionable ideas from reimagining team structures and embracing agile squads to real-world examples from industry leaders like Asana, HubSpot, Spotify, and Buffer.