Stop And Smell The Roses - November 6, 2025

Why I Am Never Satisfied

I am reading Howard Schultz's first book, "Pour Your Heart Into It: How Starbucks Built A Company One Cup at a Time”.  Schultz was the long-time CEO of Starbucks and was the driving force behind taking the original four stores that sold coffee beans and equipment in Seattle, and turning that into what Starbucks is today.  In the book, Schultz comments that after every one of his accomplishments, rather than celebrating and enjoying the achievement, he would ask himself, “What’s next?”...I'm paraphrasing somewhat but reading that got me thinking that I’m the same way!  One of my flaws is to not take enough time to celebrate what I’ve accomplished, and by extension under appreciating what I have, but instead seeking out the next challenge, or wanting more.  I have been accused of never being satisfied.  Why is that?

I suppose I could speak with friends, family, and work colleagues about this and see what advice they could give.  But that seems like bragging, and I don't feel it's a good thing to self-promote oneself. So instead, ironically, I write about this conundrum publicly, to my subscribers/followers and to those who see this article in their Substack feed.  This article is rather personal in nature, but I thought that I must not be the only person who’s wired this way. And so perhaps, giving this trait of mine some thought, and putting those thoughts down in writing would not only help me, but generate some dialogue that might help me and help others.  

Ambitious and driven people often struggle to feel satisfied, but feeling that way is not inevitable. It depends on why they’re driven and how they measure success.  Usually this behaviour comes from one two sources: 

• If ambition is fuelled by comparison or fear—such as needing to “prove” themselves or beat others—in this case, satisfaction tends to stay out of reach. Every achievement just raises the bar.

• If ambition is purpose-driven—coming from genuine curiosity, creativity, or a desire to grow—then people can feel deeply satisfied even while striving for more. They experience progress as fulfilling, not just the end result. I put myself in this category, as I am happy with what I've accomplished and what I’ve accumulated as a result. I just don’t take time to celebrate the wins; and I don’t feel like I’m done achieving all that I can, even though I’m thirty plus years into my career.  I don’t wanna stop!

  
  

The challenge is that ambitious people often have a strong internal tension: they crave progress and mastery, but that same drive can make contentment feel temporary. I’m told the key is, learning to balance achievement with appreciation—to celebrate wins without losing the spark to keep improving.  This seems simple enough, but the question I’m asking myself is why do I not take more time to appreciate the wins as I earn them?

I’m hoping someone will read this article and offer up some advice.  Until that happens I took a very 2025 approach to cracking this dilemma of mine, and asked ChatGPT why I don’t stop to smell the roses more often.  Here is what came back from the AI tool:

1. Redefine “Success” as a Moving Journey, Not a Destination:

• If success is only the next big milestone, satisfaction will always stay one step ahead. Instead, define success as growth, learning, or alignment with your values. Example: Instead of “I’ll be satisfied when I hit X goal,” reframe it as “I’m proud of how I’m improving and staying consistent.” Shail’s reaction   - seems obvious and lame, but probably true. 

  
  

2. Practice “Micro-Gratitude”:

• Driven people often skip over their wins. Build the habit of noticing micro-moments of progress — a good conversation, a creative insight, a challenge handled better than before. This rewires your brain to feel fulfilled in the present, not only at the finish line. Shail’s reaction   - this is also probably true, but can lead to taking your eyes off the ultimate prize of that task, and as a result falling short. 

  
  

3. Separate Self-Worth from Achievement:

• Ambitious people sometimes tie identity too tightly to performance. That creates chronic dissatisfaction and burnout. Try reminding yourself: “What I do is one part of me. Who I am is broader and valuable beyond outcomes.” Shail’s reaction   - there is some truth to this one. I may be tying too much of my persona into being an Entrepreneur/Business Leader, when I should balance my self-perspective out with other identity factors, such as being a Board Director, a father of two fine young men, a sports fan, a political news junkie, a lover of California Cabernet Sauvignon, and a huge Van Halen fan. 

  
  

4. Keep a Long View:

• Ambitious people often think in “sprints.” But fulfillment comes from zooming out—seeing your path as a long, evolving story. When you see your ambition as part of a life narrative, not just a to-do list, you can feel proud of your direction even if you haven’t “arrived.” Shail’s reaction   - again, there is merit to this point of view. One does need to be aware of the forest that is their entire life, not just the trees we encounter along the way.  

  
  

ChatGPT spit out a few other ideas but they seemed somewhat repetitive, and quite frankly simplistic, so I didn’t bother including them here.  In terms of acting as my therapist, I would give ChatGPT a failing grade, but that could just be me being a terrible patient in this context!  I’ll admit that I didn’t try some of the other AI tools (such as Google Gemini or Perplexity), as I assumed they would supply the same kind of advice.  This exercise was also an experiment for me in the use of AI tools, for personal advice; I don’t do that at all, but I’m hearing a lot of people do, so using it in the course of writing this article was a good learning experience.  Like everything else you read on the internet, you have to apply some logic and common sense when processing the results of an AI tool.

I’ve come to the conclusion that ChatGPT has offered some meaningful words of wisdom, that are the correct approach to feeling more appreciative of the wins we achieve. They are somewhat intuitive, but nothing earth-shattering that one wouldn’t think of on their own. Perhaps my expectations were too high of the AI tool, and that there isn’t really a silver bullet of wisdom to be had here.  Perhaps the answers I seek have been staring me in the face and I should recognize and act on the obvious solutions.  Regardless, I look forward to the readers' comments and advice on doing a better job of celebrating wins along the way.