Saturday Cup of Joe: a leadership and tech(ish) newsletter from Detroit

8 min readMar 24, 2018

Friends & Colleagues,

SCOJ #98. Coming to you from the Left Coast. Structure this week — out the window. I’m working out of hotel lobbies and taking calls between meetings. So, I hope the fun and inspiration comes through this week, but the usual format is gone again. We’ll see if it ever comes back.

Trees. La Jolla, CA.

I’ve always taken a positive approach whenever I have to travel. I embrace it as an opportunity and try to take in as much of the local city or community as possible. As anyone who travels knows, it is difficult to stay connected through texts, calls, and Facetime. That’s compounded when time zones come into play. I found FaceTime dropped my calls or didn’t connect this week, which added to the distance.

On the upside, I visited the home office of the company I represent and was excited to be able to connect in person with the team there. I spent a brief lunch break driving to the beach, walking around a palm tree, and driving back. But it was worth it.

The time also helped me evaluate my work in a new way. I am trying to get better about time management and prioritization. I often fall into the bad habit of starting with whatever is at the top of my inbox. This week, I tried to be more discerning about priorities. I ended up working more but felt like I moved the ball more too. We’ll see.

How often do you evaluate or reevaluate your daily habits or routines? I might add a calendar invite to “wake myself up” and avoid long periods where I don’t give it some thought. Again, we’ll see.


Who do you want to be? I’m revisiting this question this week thanks to Ryan Holiday. Twice. I’m reading his book Conspiracy about the lawsuit between Gawker media and Hulk Hogan funded by tech billionaire Peter Thiel. It’s amazing. Holiday deconstructs conspiracy as a word and a concept before telling a riveting tale of how the plan came together.

The second interaction with Holiday this week was a post he wrote looking at success versus obscurity. Holiday wonders if there isn’t more honor in succeeding quietly. He wrote, “The key then, when you find yourself wanting more, feeling inferior because you don’t have more, is to think about that. Don’t give the fantasies more weight than they deserve. See them for what they are.”

Anyone who knows me and reads Saturday Cup of Joe knows that I have always struggled with the fantasy of “the life” or the “big break.” What a great reminder to ignore the distracting feelings of inferiority (clearly based on some external standard, not our own) and ground myself in a clearheaded view of success and ambition.

Holiday goes on, “The next time you feel screwed that you haven’t gotten your big break, or watch as some potential life-changing opportunity to level up escapes your grasp, ask yourself if that’s really the case. Is it really bad luck? Or has Fortune done you a kindness?”

I’m embracing the work and the process this week/weekend and looking forward to whatever life has in store without pretense or expectation.

What are you thinking about this weekend?


Namesake spotted on Hollywood Walk of Fame.


Detroit Opera House, Detroit, MI, USA

Valuable Lessons: Given good story telling versus authority as a decision-maker, authority always wins. Good salesmanship, good selling has value and can be influential. No question. Yet, what gets people’s attention is “my organization has empowered me to make a deal here.” It could be the most interesting, sexiest deal ever (though, let’s be honest, they rarely are) but no one is paying attention until it is “real.” On the other hand, someone with authority can provide a cut-and-dry presentation, but if they have ability to get it done, the participants will be engaged. This doesn’t mean to cut corners or discount a presentation when you are presenting someone from your organization with the authority, but it’s a reminder not to overvalue presentation in your preparation or strategy.


More on subjectivity: Last week I included a comical but real poem that I constructed from my daughter’s flashcards. It was titled “Think Well.” This week someone sent me a story titled “What Does It Mean to Think Well?” I was excited to dig in. Here’s what I found:

The author writes (and I agree), “Human beings don’t deal in neutral information. We exist inside our own minds and theories.” It’s important to understand when trying to make big decisions — like what work you’re doing or whose priorities should matter to your work — but also when making daily decisions leading your team or your company. It’s not about fighting to eradicate this subjectivity. In fact, that’s almost never worth it.

What matters most is how we transform the world into the right question. The next generation will not be dominated by who is the smartest, because computers and AI will take care of that. It will be dominated by who can ask the right questions.

For instance, the author notes, “Even in the most abstract of theoretical pursuits, reasoning is more often an extension of the will than a path to change. Two perfectly reasonable lines of thought starting from two different sets of assumptions will end, perfectly reasonably, in two different places.”

It’s the poking and prodding around the issue, around the facts, around the project that gets the most done. Getting the team or the company to think differently is where the action is. That’s more likely to produce effective and productive outcomes. This week, ask better questions.


Self-awareness: Kinda the whole ballgame. I’ve written in the past that perspective is the whole ballgame, but self-awareness is just a specific, important perspective. Harvard Business Review studied self-awareness and found there are 3 key distinctions or factors:

1. Internal vs external self-awareness. Different and both necessary.

2. Experience and power hinder self-awareness. (Or what’s worse — distort it.)

3. Introspection doesn’t necessarily equal self-awareness

To quote the author: “One of the most surprising findings of our research is that people who introspect are less self-aware and report worse job satisfaction and well-being.”

Based on my reading and interpretation, this means that introspection combined with some ability to see yourself the way the world does is what makes the difference. It takes both — the thought and the perspective. I’ve worked on this, choosing to straight up ask someone I respect who is either close enough to me to tell the truth or whom I trust not to sugarcoat or hedge their response. Now I ask you — if you have any sense that there’s some aspect to my style, my communication or my work that indicates a lack of self-awareness or that I should improve, please tell me. I would really appreciate it and it would undoubtedly deepen our relationship. Thank you.

Detroit, MI, USA.


Quirky Content: Do you have a bucket list? Are there any experiences or activities you’d like to try before you kick the bucket? Here’s one guy’s list of 20 “things.” It’s a bit more philosophical than most lists. But definitely made me think. There’s value in writing a list even if you already carry one in your head. Putting it on paper changes the idea.


Challenge question: Would you rather be right or feel more human? Not mutually exclusive, of course. I came across an interesting blog post this week about the tension between right and wrong, but it takes it a step further, focusing on right and understanding.

By understanding, I believe the author means striving for understanding over correctness. To me, that means not being right at all costs or focusing on being right at the expense of humanity.

Benefits of being wrong:

1. Accepts vulnerability

2. Embraces a lifetime of learning

3. Lives open to new possibilities

4. Prioritizes self-growth over external expectations

5. Nothing to prove

The blog post goes even further — Practice Being Wrong.

1. Lose an argument on purpose. I tend to start an argument on purpose (out of curiosity) but often don’t think of it as losing. Though I like the idea. Something to think about.

2. Support a decision you disagree with — how’s it feel?

3. Adopt an opposite belief as true — I would say also determine what belief you hold that most people disagree with. Celebrate that.

4. Be open to change your mind. Be intentional about it. It can be a stated commitment.


Click this link for amazing bird photos.


Today’s Thought: Engaged but not invested. I heard this thought about today’s social media culture. It’s also how I would describe much of what I experience (and am guilty of) online. One observation of what social media culture has created is a group of people who are engaged — posting, sharing, commenting — but not invested — demonstrating, organizing, protesting — in the causes of our day.

Whether it’s an audience, a client or a team, the key is to make the step from engaged to invested. Engaged is critical to get the eyeballs and earballs you need but until it transfers into action, whether the action is a behavioral change, speech change, or actual activity, it remains an idea. Investment leads not only to action but investment of another kind — financial. Strive for investment in your work, your writing, and your leadership.


Quote: If you ask my opinion, I’ll give it to you. If you ask my advice, you’d better take it. — Daniel W. Potter


Bonus Content: I recommend exploring Kialo. My wife sent this to me. It’s a fascinating way to post ideas and writing. Readers then submit “claims” and essentially vote up or down the central thesis including being able to submit their own variation.




Thinker, curious leader, once an attorney…always trying to answer well. Working on what’s next and next and next.