Do Hard Things

Happy Friday Sippers,

TLDR | Stop waiting for the "drop", the most durable brand is built in the deep water.

How was your week?

Mine was spent in the "Stretch Zone." And by that, I mean I was at a waterskiing camp, attempting to master the slalom on one ski.

For the uninitiated: "Slalom" means skiing on one single, narrow board instead of two. Most people start on two skis for stability and "drop" one once they're up. Not me. I went for the Deep Water Start.

Imagine sitting in the water, one ski pointed at the sky, waiting for a boat to drag you upright at 30mph. There is no safety net. No training wheels. It's a 0-to-100 commitment, with only two choices: "Succeed" or "Face-plant (read forced nasal rinse)."

This feeling of being dragged into the unknown has defined my recent career. After 25 years as a brand builder, I joined Google. I wasn't just switching companies; I was switching ecosystems:

• The Tech Shock | Moving from a traditional Corporate environment to a hyper-growth Tech giant.

• The Industry Pivot | Jumping into a new industry, Financial Services, helping brands win in an industry defined by performance and high-stakes regulation.

• The Identity Crisis | After two decades of mastery, I was back to being the person asking the questions instead of answering them.

Lessons from the "Deep Water" 📏

1. Mastery is a Mindset, Not a Tool ⛷️ The move from Corporate to Tech often feels like losing your language, feeling out of water if you will.

   The Lesson | When you switch ecosystems, don't mourn the loss of your old tools. Lean on the underlying logic of your career. The "pipes" might look different, but your plumbing principles remain your greatest asset.

   
   

2. Alignment Prevents the Crash 🚤 On one ski, if your body isn't perfectly aligned before the rope goes taut, you're going under.

   The Lesson | Entering the Financial Services industry required me to align my brand expertise with a highly regulated environment. I didn't change my "core"; I recalibrated my stance to keep pace with the speed of a new industry.

3. Trust the Tension 💧 Imposter syndrome feels like a force trying to pull your arms out of their sockets. In skiing, if you fight the rope, you lose. If you lean back and trust the tension, you rise.

   The Lesson: I stopped fearing the "beginner" label. Being the one to ask the "obvious" questions is a superpower. It's how you find the gaps the "experts" are too comfortable to notice.

Living in the Stretch: 6 Lessons for your Brand 🏗️

At Google, we call it the Stretch Zone, but starting on one ski is more like jumping straight into the High-Performance Zone. It requires a level of core strength and "alignment-under-pressure" that you just don't get when you have a second ski to lean on.

1. You Have to Lean Back to Move Forward ⛷️ In skiing, if you lean toward the boat (the "safe" direction), you fall. You have to lean back and trust the tension.

   The Brand Parallel | When markets get volatile, the instinct is to "lean in" to the familiar. Real growth requires leaning back into your Brand Purpose, trusting your "Why" to pull you through the waves.

   
   

2. Speed is Your Friend (Until It Isn't) 🚤 Decision velocity is critical, but if your alignment is off, speed just makes the crash spectacular.

   The Brand Parallel | Execution matters more than ideas. But executing at high speed without Excessive Product Discipline is just a fast way to fail.

   
   

3. The "Drop" is the Hardest Part 💧 Transitioning from two skis to one is terrifying. You have to let go of a support system to find true agility.

   The Brand Parallel | To scale, you eventually have to "drop" the legacy processes that served you at the start. You have to trade the stability of the past for the agility of the future.

   
   

4. Alignment is Everything (Before the Pull) 📏 When you start on one ski, if your body isn't perfectly aligned before the boat moves, you're done.

   The Brand Parallel | You can't fix a bad strategy once the "funding boat" starts to pull away. Your product-market fit and brand soul have to be aligned in the quiet moments of pre-launch.

   
   

5. The Power of "Instant Commitment" 🚀 There's no "testing the waters" on a deep water start. It's 0 to 100 in two seconds.

   The Brand Parallel | In a moment-obsessed culture, a slow launch is a dead launch. The best brands today "pop" out of the water with a clear voice. They don't iterate in public until they've nailed the "up."

   
   

6. Skipping the Training Wheels Builds Muscle 💪 By never using a second ski, you're forced to build "stabilizer muscles" from day one.

   The Brand Parallel | Bypassing "easy" growth hacks (like heavy discounting) and going straight for Product Discipline is harder. But that brand muscle is what makes you unshakeable when the wake gets rough.

The Sip Takeaway 🍷☕🍸

Doing hard things is inherently "uncomfortable."

But as we say at Google, the stretch zone is where the magic happens.

If your brand or your career feels a little too "comfortable" right now, you aren't in the Stretch Zone. And in a market that moves this fast, the comfort zone is the most dangerous place to be.

The Lesson | Stop waiting for the "perfect" conditions to drop the second ski. Align your core, trust your 25 years of muscle memory, and embrace the splash.

Cheers to doing hard things,

Go Habs Go

See you next week.