For the final lesson in the series I saved my favorite; one I talk about often. If you look closely, everyone’s playing checkers while pretending to play chess. They talk about “long-term thinking” but really mean next quarter’s numbers. I used to be that person, head buried in daily operations, thinking I was crushing it. I was not. Nor are you if this describes you. Tomorrow is important but having the discipline to look 5, 10, even 15 years out is transformative. Not the safe, incremental stuff. I’m talking about the big, scary changes that make people uncomfortable. Sort

Something we all struggle with – keeping friendships alive while chasing the business dream. I’ve watched too many rock-solid friendships fade into LinkedIn connections, not because of drama or falling out, but because I got caught up in the “I’m too busy” trap. It sucks and, when I look back, I don’t love it. Here’s the thing about building a business – it’s all-consuming. You’re grinding, thinking you’ll catch up with friends “when things calm down.” Spoiler alert: things never calm down. I looked up one day with a problem and realized, I had no one to call. Not

After building a lot of tech I realized something – we’re all obsessed with the wrong thing. Early in my career, I was that person staying up late tweaking UI elements, convinced that building the perfect product was the key to everything. Nope. Here’s what actually matters: recognize that your value is not in the product but in the clarity of thinking deployed to deliver the product. These are different things. Period. When we see projects fail, we all know the product wasn’t the problem. The thinking was. We’d been so caught up in building the “perfect” thing that

Something that keeps hitting me after a few decades in tech – we’re really good at fooling ourselves. The industry moves so fast, acronyms arise out of nowhere, AI became a real thing finally, blockchain is still something no one really understands, and whatever new thing dropped this morning, that is also moving quickly. All of this movement often allows us to get caught up in our own hype. And that’s where things get dangerous. Here’s what I keep seeing: smart people (yes, myself included) get trapped in this echo chamber of our own expertise. We start thinking we’ve

Something I’ve picked up after years in tech – almost every conflict comes down to people not being on the same page. Not because anyone’s being difficult, but because we’re all working with different information. The solution? Become the teacher in the room. Take command of making sure everyone is on the same page and working with the same information. I used to think sharing knowledge was just about being helpful. But I’ve watched too many projects implode because someone assumed everyone else knew what they knew. It’s like we’re all playing the same game but with different rulebooks.

I keep finding you’ve got to become borderline obsessed with understanding your clients’ businesses to really make a splash. Not just the surface-level stuff they throw at you in meetings, but the nitty-gritty details that make their world tick. Developing this deep sense of how things work helps the next client as well. It also makes you likely the most valuable person on a bar trivia contest as well as above-average-proficient in Jeopardy; neither of which I find objectionable. I stumbled across what has become of my favorite reads, Joshua Foer’s “Moonwalking with Einstein” a while back, and while

Projects with planning always, and I mean always, turn out better. No other way of saying that. Include planning in your budgets, include planning in your calendar, and don’t fuss if you agency wants time to plan. Yes, you should pay them too. Even if you outsource this to AI, guess what? Crafting a prompt worthy of a publishable outcome still takes time and still means you sat, even for a nanosecond, and applied conscious thought to your idea. That, if nothing else, is worth vastly more than skipping this. Look, as someone who’s watched more projects crash and