Cheers! 

How about some vulnerability to start your Sunday night? 

Last week, I wrote about how much of my self-worth I place in my career and the importance of balance. Well, let me give you an example of imbalance, my friends. Some of you might relate. 

A few nights ago, I had a dream that made me laugh and slightly worried.

Like most dreams, this one involved a wild mash-up of crazy scenarios and a random group of people, including my current boss, Andrew. We were on a mission, though the exact specifics were confusing. It involved helping Santa deliver toys and building a spaceship to fly to Mars. 

Riveting.

Most of the dream consisted of our journey to some destination. The best part of the dream? I couldn’t get anything right. Every task I was given I couldn’t complete: rolling down a window, grabbing a tool from the back, fetching water at a truck stop, or grabbing a box containing some weasel-rat hybrid. No matter the task, I failed, miserably. 

You all know this type of dream… akin to wearing no pants to school. 

And, of course, my real-world boss was leading the Santa-Mars-bound-helpers. And I was failing him.

When we finally arrived at the destination, we were not helping Santa but an older woman packing up her house. I'm not sure how it connected to the Mars trip, but she handed me a fragile, antique sword and asked me to pack it. 

Easy, right? Nope. Every box I tried was too small. 

Again, I failed.

Eventually, everyone was pissed and disgusted with me (especially Andrew) and left me behind. I had no way to get home and had to walk. Luckily, the dream ended before the shameful journey back to Santa’s (?) workshop. 

I laughed out loud, mainly because I was relieved that the dream wasn’t real but also because the whole thing was absolutely absurd.

But here’s the truth: dreams are a mirror of our subconscious. Maybe this one reminded me that perfection is never the goal and is not even realistic. Sometimes, failing a task (or twenty) in a dream (or life) doesn’t mean we’re incapable. It just means we are human. And you don’t need to stress out too much about it.

So, if you’ve ever felt stuck, overwhelmed, or carrying a fragile antique sword you can’t pack, know you’re not alone. And sometimes, it’s okay to laugh at how seriously we take it all. 

And how much we need to chill out.

❤️ Kyle

On Anxiety & Taking Creative Risks

Now that we have the triggering, anxiety-riddled dream out of the way. Let’s continue our deep dive into anxiety, nervousness on the job, and how that connects to taking creative risks. 

Let’s lead with one of my favorite quotes from Rory Sutherland, author of Alchemy and overall badass marketer: 

“It is much easier to be fired for being illogical than being unimaginative. The fatal issue is that logic always gets you to the same place as your competitors.

In other words, playing it safe often leads to mediocrity. And if you aren’t at least a little nervous before launching a campaign, product, or design, chances are you’re not taking creative risks. 

We felt that tension firsthand this week as we launched a brand-new homepage design for Jellyfish.co. The anxiety was real.

Why?

Because we were breaking the mold, instead of following the standard homepage playbook— headline, hero image, and product demo, we flipped it. 

We talked to our customers and focused on the most important use cases and outcomes they achieved by using our product. Instead of showcasing our features, we emphasized the why rather than the what. 

We also reduced our demo request to a one-click email instead of a multiple-click, multiple-form fill experience. 

This wasn’t just a design refresh but a strategic shift that made us nervous. 

But we knew it was the right move. Why? 

1. By focusing on outcomes, we are speaking directly to our customers. It’s not about us, it’s about them. 

2. Reducing friction is a must. Every additional click or form allows someone to bounce (not good). 

3. Being willing to take risks in design or messaging isn’t just about looking different. It’s about staying relevant.

The lesson? Feeling nervous is often a sign you’re on the right track. Creative risks don’t always guarantee success, but they do guarantee growth. 

And yes, we will be testing, tweaking, and adjusting. After all, isn’t that what doing our best work is all about?

On Budgeting for Brand or the 70/30 rule

One of the most common questions I get—whether on podcasts or in one-off conversations—is this: What’s the right balance between brand building and demand generation, and how should marketers allocate their marketing budgets effectively? 

The truth is, there’s no one-size-fits-all answer—we all know that. However, over the last few marketing leadership stints, I have found a few ideas that can serve as a framework for making these decisions. 

The 70/30 Budget Split

A  starting point for marketing budget allocation is the 70/30 split (this is across headcount and program spend):

• 70% of the budget focuses on demand generation—activities designed to drive direct, measurable pipeline and revenue growth. 

• 30% is allocated to brand-building initiatives, which deliver long-term value through differentiating the brand and surprising/delighting customers and prospects.

Both tactics matter for may reasons, but ultimately, they boil down to driving tangible pipeline and bookings goals to support brand-building initiatives.

It also helps manage expectations on the brand side. The 30% of brand-building initiatives are usually harder to measure but essential for long-term success. Tactics like creative direct mail, billboards, and high-impact events won’t always show immediate ROI. 

Focusing on driving bookings goals with the 70% allows you to take creative risks with the remaining 30%. 

This balance isn’t static, depending on the size of your company. For early-stage companies, prioritizing short-term growth often means skewing more heavily toward demand generation, more of an 80/20 split. As the business matures and brand/messaging differentiation becomes important, a 70/30 or even 60/40 allocation can make more sense.

Adjusting the Budget Over Time

It makes logical sense, but let’s spell it out. Your budget allocation should evolve as your company grows:

• Early-stage companies: Prioritize demand generation to fuel immediate growth (80/20 split).

• Growth-stage companies: Shift toward a more balanced allocation as the need for differentiation grows (70/30 split).

• Established companies: Consider a 60/40 split, where brand investments amplify the reputation and trust you’ve already built.

Finding the right balance between demand generation and brand is both an art and a science. Start with a framework like the 70/30 split, adjust it over time as your company grows, and remember the value of flexibility.

Remember: the best marketing strategy isn’t just about hitting pipeline and booking goals. It’s about celebrating the tangible wins while investing in the intangible stories. You have to balance both.

On When To Push and When to Nurture Your Kids

I constantly struggle to balance pushing my kids to be their best and nurturing them. Thankfully David Willans (who I mentioned in last week’s edition) of BeingDads.com, has an excellent way to look at the balance. 

He writes that while it’s important to encourage kids to step outside their comfort zones, doing so with empathy and humor helps reduce stress. Pushing should focus on growth rather than specific outcomes, and parents should consider their child’s perspective and emotional readiness. 

Every child responds differently, which means you have to be flexible. 

But there’s also a parenting paradox: knowing when to push children to grow and when to nurture them by easing the pressure. It’s important not to shield our children from life’s difficulties and limit their ability to expand outside of their comfort zone. 

He emphasizes the dangers of shielding children too much from life’s difficulties, hindering their ability to grow and push beyond their comfort zones.

Yet, excessive pushing can cause harm. His strategy is to use humor, maintain low expectations, and explain the intent behind pushing. This approach fosters trust, supports resilience, and allows children to surprise themselves. 

Here are a few tips to remember based on what I’ve learned over the last eight years:

Observe Your Kid’s Reactions: I’ve tried to notice how my kids respond to challenges. I’ve tried to back off with a gentler approach if they show fear or frustration. It’s not helpful, at least for my kids, to keep pushing when they are beyond reconcilable.  

Set Incremental Goals: When frustration diminishes, I break down tasks into smaller, achievable steps to gradually build confidence. My oldest son loves playing football and was frustrated by his inability to throw the “long ball.” We started small and gradually worked up to longer throws, taking breaks if he became frustrated. Eventually, we reached a point where he felt confident in his ability and was having fun.

Dad wins. 

Encourage Reflection: This is a regular one for me. After a challenging game or practice, I try to make the time to discuss what they learned and how they felt. I never give advice; I just listen. A win is when they ask for your advice.

Balancing the push with the nurturing is a challenge. Every child is unique, and this requires a more flexible approach. By listening, encouraging, and goal setting, we can help kids step out of their comfort zones, build confidence, and grow.

On Being Klueless

I will always appreciate creative bets by great marketing teams. This week’s shoutout goes to Katie Berg at Klue for their mock-u-mentary, Klueless. 

The movie is a satirical take on the challenges often occurring in any marketing, sales, and enablement team. If you liked The Office, you will LOVE this movie. 

I’m not going to ruin it for you. Just watch it. If you don’t trust me, trust Ted Winter from Fresh Tomatoes. 

“The weirdest thing I’ve ever seen, honestly.”