This Feels More Uncomfortable than Sharing My Failures

For the last two years, I’ve shared one story after another about the challenges and struggles of life and leadership. I hope you will indulge me as I pause to celebrate a moment of gratitude for the other end of the spectrum, when things actually go well.

Which ironically, I find unbelievably more uncomfortable to share than the difficulties.

The Uncomfortable Truth About Success

Here’s what I realized: most of us are really great at looking ahead, seeing how far we have to go, or looking around and seeing all the things that are broken, but terrible at pausing to acknowledge when something has gone well or appreciating the elevation gained.

But there is real danger in this pattern. When we only focus on the struggle, we rob ourselves of the joy that comes from making genuine progress. We miss the compound effect of all those small, daily decisions that eventually shift us from trudging uphill through sand to walking on firm ground. We set ourselves up for perpetual frustration, burnout, and a loss of perspective in just how blessed we are to have the opportunities (and challenges) we do.

So this month, I’m choosing to break that pattern.

An Amazing Month of Wins Worth Celebrating

Business Journal Article

What struck me most wasn’t seeing my pic in the Biz Journal (though that was pretty cool). It was how the journalist connected the dots from a resourceful farm kid to a clueless college kid to building something truly meaningful alongside an incredible team over two decades. Sometimes you need reminders that the risks you took and the uncomfortable decisions you made shaped you even more than you realized at the time. If you don’t have a subscription, let me know, and I can send you a copy of the article.

Lead With AI Momentum

We launched with a new logo, website with an AI Experience Score assessment, and Workshop Series Launch…and my LinkedIn AI content is generating incredible conversations and engagement. 

Most importantly, we’re attracting the right people: we welcomed two new members, Mark McClanahan with Mosby Building Arts and Brad Parker with Parker Law Firm. Thank you to Brian Glarner at Enterprise Bank and Marcelle LaBlanc at Velvet Box (and Lead With AI member) for these referrals. 

Two new speaking engagements were booked: MKSSA (November – St Louis, MO) and PILMMA (January – Orlando, FL). If you know any association conference organizers interested in AI leadership workshops, I’d welcome an introduction.

GBG Earned the Trust of 5 More Businesses:

• Lami Woods: helping launch what was a sub-brand into its own company with distinct market positioning
• Acme Constructors: building a new website to reflect the updated positioning and messaging we co-created with them
• Merthanye Product Corporation: collaborating with their marketing team to reactivate past prospects with a series of tailored marketing campaigns
• Trinity Products: launching an exciting new product line to their existing customer and prospect base
• SCG: activating an inbound content marketing engine to attract the right prospects with the right challenges

Crave Corner Grand Opening:

Ok, maybe the coolest of them all…and there’s definitely a whole future article brewing here on using entrepreneurship to nurture creativity and problem-solving within our kids, while they actually make money. 

But the sneak preview is that 2 weeks ago, my 9-year old son, completely on his own accord, opened a restaurant in our basement. He has now broken double-digits in customers served. He’s recruited a couple of friends as workers and they are taking their craft and the customer experience very seriously. 

Printed menus, numbered tables, mood music and candles, defined roles and responsibilities, and line-itemed bills with a “tax” that will be donated to a local homeless shelter. It’s actually been really incredible to watch.

The Permission You Need

Looking at this list, I realize how easy it would have been to rush past all these moments, already focused on the next challenge or deadline (and frankly, I still am most of the time). But here’s what I want to offer you (and me): permission to pause and acknowledge your own progress.

Not the Instagram highlight reel version of success, but the real, incremental, often-invisible progress that compounds over time. The email response (not reaction) that was kinder than usual. The meeting that ended five minutes early because the agenda actually worked. The moment your team member solved something without asking you first.

We’re so conditioned to focus on what’s not working that we miss the quiet victories happening all around us. But these moments, when we actually stop to see them…they are the fuel that sustains us through the next inevitable challenge. They’re the true purpose of our work.

Ignoring the Rules

I’m going to break every email marketing best practice and offer 5 different calls to action. Choose the ones that resonate, or ignore them all, but I hope you’ll take something from this reflection:

(1) Take five minutes this week to write down your wins from the past month. Not just the big, obvious ones, but the incremental progress ones that are easy to overlook. You might be surprised by what you discover. Then reply to this email and share them with me. I’d love to celebrate with you.

(2) Help me help you help me. 🙂 Please take 3 minutes to complete this AI Experience Score assessment on the website. It identifies where you are in your AI journey and provides some ideas to get to the next level…a good investment of 3 minutes and the feedback will help me improve on this beta version.

(3) If you hear someone express their frustration with using AI in their organization, I hope you consider forwarding them this email or sending them to www.LeadWithAI.Us. The upcoming workshop series might be exactly what they need.

(4) I’ve found the easiest path to AI adoption is to start playing around with it personally. So, I’d like to offer you the opportunity to build your own version of my favorite personal tool, which is a Meal Planner. All you have to do is copy and paste this Meal Planner Wizard Builder prompt chain from the Google Doc into a chat, and it will walk you through step by step how to build the training guide and instructions for your own CustomGPT or Claude Project Meal Planner. This saves me 1-2 hours every week. Let me know how it works for you!

(5) Review the Top 10 List for GBG below. If you have contacts at any of the companies (or ones similar to them) below, we would love the opportunity to find out what is/isn’t working for them in finding qualified leads, and see if there’s any way we can help…whether with sharing experiences, making introductions, or potentially working together. We value your referrals and will make sure our interaction adds (not subtracts) social capital in your relationship.

Pulling It All Together

Growth isn’t just about removing obstacles, it’s about recognizing that the weight of those obstacles didn’t get lighter, you just got stronger. That the trudge didn’t become less steep, you just built more endurance. That the compound effect of your decisions moves you forward in a meaningful and enjoyable way.

The next small step may be necessary. But first, together, let’s take a pause long enough to acknowledge how far we’ve already come.