What if we could all realize our possibility?

Back in 400 BC, Plato posited that the right question is usually more important than the right answer.

Einstein once said if he had an hour to solve a problem, he'd spend the first 55 minutes thinking about the problem and five minutes thinking about solutions. Asking the right questions is a lot like identifying the right problem.

The most effective teachers and coaches understood that their students and clients often had the answers or would retain the information better if they discovered them on their own.

A question can put you on a journey towards discovering your life's purpose, repairing a broken relationship, having a breakthrough at work or home, or it can just be another question. The choice is yours!

But how do we get better at asking the right questions?

That's where The Learning Loop comes in. Each week, I'll ask you one thoughtfully curated, timely question. I'll share why the question is important and provide you with a relevant resource.

With greater clarity each week, you'll become a better student, a better teacher, a better manager, and, most importantly, a better you. Ultimately, realizing your possibility.

Sunday, May 18th, 2025

What is the biggest risk I’ve taken in the last 12 months and what did I learn from it?

In 1804, Meriwether Lewis and William Clark embarked on a daring expedition to explore the uncharted American West. Tasked by President Thomas Jefferson, they ventured into unknown territories with no clear maps, uncertain alliances with Native tribes, and countless natural obstacles ahead.

The risks were immense—harsh weather, treacherous terrain, and the looming threat of failure. Yet, Lewis and Clark pressed forward, believing that discovery was worth the danger. Their expedition not only mapped vast stretches of land but also fostered relationships with Native communities and provided invaluable insights into the nation's potential.

Their journey reminds us that the biggest risks often yield the greatest rewards. By stepping into the unknown, they expanded the boundaries of a young nation and their understanding of what was possible.

Sunday, May 11th, 2025

What’s one thing I’ve been avoiding, and why?

At first, I struggled with this question. I pride myself on being proactive, Type A, and someone who doesn’t shy away from tough conversations—whether in conflict, negotiations, or leadership. But when I sat with it longer, I realized I’d been avoiding something deeply personal: talking to my mom.

Our last conversation felt off, but I assumed we had smoothed things over enough to keep things cordial. When I didn’t hear from her for a while—including on my birthday (though to be fair, that’s not unusual)—I started to wonder. It wasn’t until I brought it up with a sibling that I learned we weren’t in a good place. And instead of addressing it, I withdrew.

The truth is, I don’t feel motivated to try to fix it again. I’m not expecting a resolution or even a positive outcome. But I also recognize that acknowledging what we’re avoiding can be the first step toward deciding how—or if—we want to confront it.

Sunday, May 4th, 2025

What are my own “sour grape” moments?

A fox once stumbled upon a vine full of ripe, juicy grapes. Tempted, the fox leaped high, trying to reach them. But the grapes remained out of reach no matter how hard he tried. Frustrated and exhausted, the fox gave up, muttering, "They were probably sour anyway."

By dismissing what he couldn’t have, the fox protected his pride. But in doing so, he missed the chance to understand his limitations and grow.

In business and leadership, we often face our "sour grape" moments when we fall short and quickly rationalize the loss. We tell ourselves the deal wasn’t worth it, or the opportunity wasn’t right. But when we dismiss what we once desired, we lose the chance to learn.

True leaders embrace failures as lessons, not excuses. Growth comes from acknowledging our shortcomings and asking the hard questions.

Sunday, April 20th, 2025

What’s a small habit or activity that brings me joy?

Early in Starbucks’ journey, CEO Howard Schultz made it a point to visit cafes regularly. He didn’t just oversee operations—he connected with baristas and customers, observing their experiences and building relationships. For Schultz, this small habit of engaging directly with his community brought him joy and grounded him in the company’s mission. It wasn’t about big meetings or grand gestures—it was about the simple, meaningful moments that reminded him of Starbucks’ purpose and values.

For Schultz, this practice fueled his passion and created a culture of connection and service within the company. When aligned with our core values, small habits can make a world of difference in our lives and businesses.

Sunday, April 13th, 2025

If I could relive one moment from the past week, what would it be and why?

This past week brought its fair share of both—work highlights as deals we’ve nurtured for months finally closed, moments of synchronicity on the team that felt like pieces clicking into place, and cherished time at home with my wife and daughter.

Recalling those moments—feeling the relief of a deal closing, the harmony of a team firing on all cylinders, the warmth of family time—was enough. The beauty wasn’t in going back but in pausing to appreciate and savor them again, knowing they were fleeting yet meaningful.

Moments, by their very nature, are singular and irreplaceable. When we honor that, we cultivate a deeper sense of presence and awareness. The key isn’t in trying to hold on too tightly or redo the past, but in living so fully in the present that the memory of it brings its own quiet contentment.

This reflection reminded me of something profound: as leaders, our presence isn’t just a gift we give to others—it’s a gift we give to ourselves.

Sunday, April 6th, 2025

What is a recurring thought I’ve had recently, and how does it make me feel?

In 1962, John F. Kennedy stood before Congress and declared his bold vision: to land a man on the moon before the end of the decade. At the time, this goal seemed impossible—there were countless unknowns, and the technology needed didn’t exist yet. However, Kennedy’s recurring thought wasn’t about the risks or the uncertainty—it was about the power of commitment and the collective effort that could turn this dream into a reality.

Kennedy often reflected on the idea that, while the path was unclear, the journey itself would be transformative. He was unafraid to embrace the uncertainty and move forward with confidence, knowing that progress didn’t require perfect clarity at the outset. In fact, his recurring thought was this: bold action, despite uncertainty, could lead to breakthroughs. And it did. The moon landing became a symbol of human ingenuity and courage.

Kennedy’s commitment reminds us that sometimes, it’s not about having all the answers. It’s about trusting the process and moving forward, even when the outcome is unknown.

Sunday, March 30th, 2025

What is one thing I'm proud of about myself today?

As leaders, we often focus on big wins—closing deals, scaling teams, or making impactful decisions. But sometimes, the victories that matter most are the small, personal ones that remind us we’re evolving in ways that ripple outward.

This week, I had a moment that made me pause and reflect on something I’m proud of: my progress in asserting myself. It’s not a skill that comes naturally to me, which I discovered after reflecting on one of our loop questions last year.

My wife helped me see that sometimes, asserting myself is not just about getting what I need but also about helping others—like a waiter or barista—deliver better service.

Fast forward to this week, and I found myself in a situation that tested this growth. I was in line at a local coffee bar when the barista took the order of someone who came after me. Instinctively, I began to grumble under my breath. But then I remembered my commitment to doing better. Instead of stewing in frustration, I politely alerted the barista to what happened.

She didn’t immediately "unskip" me—she finished the other order first—but she did write a small "I'm sorry" on my cup. It wasn’t the outcome I expected, but it was an acknowledgment. More importantly, it was a sign that I had asserted myself respectfully.

Leadership isn’t just about guiding others; it’s also about leading ourselves, especially in areas where we know we need to grow. This small interaction reminded me that even incremental progress can be something to celebrate. And when we lead ourselves with grace and intention, it creates a foundation for leading others more effectively.

Sunday, March 23rd, 2025

Am I Growing Tall or Growing Strong?

A young bamboo shoot sprouted from the earth, stretching eagerly toward the sky. Beside it, an oak tree seedling quietly began to push its roots deep into the ground.

The bamboo grew swiftly, towering above the oak tree in a matter of weeks. Proud of its rapid growth, it boasted to the oak tree, “Look how fast I’m growing! You’re so slow and small compared to me!”

The oak tree, unmoved by the bamboo's words, continued to grow its roots deep into the earth, silent and patient. Seasons passed, and while the bamboo reached its full height quickly, it remained fragile and vulnerable. Its rapid growth gave it outward beauty, but it lacked the resilience to withstand the harsh winds and storms.

Meanwhile, the oak tree, though slower in its outward growth, developed a strong root system and a sturdy trunk. When the storms came, the oak stood tall, weathering the challenges with strength, while the bamboo bent and broke under the pressure.

Resilient leaders know true growth isn’t about how fast you rise, but how deeply you root yourself. It’s the quiet, steady work done in private that builds resilience and creates the foundation for lasting success.

Sunday, March 9th, 2025

If my 80 year old self would ask me to do one thing, what would it be?

Jeff Bezos, reflecting on his decision to leave a stable career in finance to start Amazon, spoke about his "Regret Minimization Framework." He imagined himself at 80, looking back on his life, and asked what he would regret more: staying safe in his job or taking the leap to pursue his vision. That perspective gave him clarity. Bezos took the leap, despite the risks, and built one of the most transformative companies in history.

This might sound unusual, but I’ve never shied away from being vulnerable, so I’ll share it anyway. One of my “superpowers” is the ability to vividly imagine a future state and embrace what it feels like in the present moment. These feelings become so tangible they compel me to act. When the imagined future is painful, it drives urgency and sacrifice to avoid that suffering—even if, as the Stoic philosopher Seneca might argue, the pain is more imaginary than real. When the future is filled with joy and possibility, it fuels my time and energy planning and designing systems to bring that vision to life.

As the Chinese proverb reminds us, “The best time to plant a tree was yesterday. The second best time is now.” Imagining the perspective of our future selves can guide us to focus on what truly matters today.

Sunday, March 2nd, 2025

What's one thing that doesn't serve me that I need to kick?

When Satya Nadella became CEO of Microsoft, he inherited a company struggling to stay relevant in a rapidly evolving tech landscape. Early on, Nadella identified a mindset holding the company back: internal competition between teams. He recognized that this culture didn't serve Microsoft's mission to empower every person and organization to achieve more. Nadella famously shifted the company’s focus to collaboration and a growth mindset, dismantling silos and fostering innovation. The result? Microsoft transformed itself into a trillion-dollar company with thriving cloud services, AI advancements, and a revitalized brand.

Sometimes, what holds us back isn’t a lack of ambition but the baggage we carry. Whether it’s outdated habits, toxic relationships, or rigid beliefs, identifying and shedding what no longer serves us creates room for growth and success.

Sunday, February 23rd, 2025

What is keeping me up right now?

We don’t fill a leadership position without a strong propensity for action. One of my most respected executive coaches reminds me that exceptional leaders are essentially undercover jugglers—keeping multiple balls in the air while staying intentionally focused on the one they need to catch next. Whether something pressing immediately comes to mind or you’re feeling calm and sleeping soundly, identify the ball that requires your attention and evaluate your plan to successfully keep it in play.

Sunday, February 16th, 2025

Where am I taking an unnecessarily difficult path?

I’m a proponent of the hard way, especially when it’s clear it will lead to an easier life. Take the elevator, escalator, or stairs—I’ll take the stairs. Consider buying something I want that might force me into debt—I scale back my desires. However, don’t mistake my preference for the hard way as a willingness to make life unnecessarily difficult. I actually prefer the path of least resistance, but that doesn’t mean I never forget when I should pick up the phone to ask for help or step back to reevaluate my approach. It’s President’s Day weekend in the United States, so I decided to reflect on a moment from history.

In 1776, George Washington faced a daunting challenge during the Battle of New York. Outnumbered and outmaneuvered by the British, Washington initially tried to hold every position, spreading his forces too thin. As defeat loomed, he made the pivotal decision to abandon Manhattan and retreat across the East River. While retreating was seen as risky and unglamorous, it ultimately preserved his army to fight another day.

This moment of reflection—choosing a strategic withdrawal over a futile stand—illustrates the power of reassessing our path. Washington realized that stubbornly clinging to an impossible position would lead to disaster, while adapting allowed the possibility of future victories. Sometimes, the wiser path isn’t the harder one but the one that ensures long-term success.

Sunday, February 9th, 2025

What am I doing to sharpen my saw this year?

Two men were hired to saw wood. They were given an equal amount of wood to saw and told to see who could finish first. Both men began sawing immediately. However, one of the men stopped after a few minutes to sharpen his saw. The other man laughed at him and said, "What are you doing? You're wasting time! I'm going to finish sawing all of this wood before you even get started again!"

The man who stopped to sharpen his saw said, "I know it may seem like I'm wasting time now, but I believe that taking the time to sharpen my saw will make it easier to saw the wood and I'll be able to finish the job faster in the long run."

The man who didn't sharpen his saw continued to saw, but he quickly became tired and his saw became dull. He had to stop and rest frequently, and his progress slowed down. The man who stopped to sharpen his saw, on the other hand, was able to saw for longer periods of time without getting tired. His saw was sharp, so he was able to cut through the wood more easily.

Sunday, January 26th, 2025

Am I connected to my why?

The source of my energy to overcome challenges and setbacks comes from a deep, personal connection to my "why." However, without a pressing problem or existential threat, I’ve noticed myself drifting at times. It’s easy to remember to brush our teeth after seeing the dentist, to pray when life feels dark and hopeless, or to prioritize loved ones after a loss. But even without adversity, these actions are still beneficial. Likewise, it's important to draw energy from reconnecting with our "why," even when we don’t think we need it, or to evaluate if it's still truly nourishing us.

Sunday, January 19th, 2025

What is something happening in my life right now that I haven't talked to anyone about?

"Invisible baggage" is a metaphor for the emotional and mental burdens we carry. The weight of these burdens can lead to harmful behaviors, such as outbursts, difficulty concentrating, overspending, excessive drinking, or road rage. Bottling things up rarely ends well. Simple acts like journaling or talking to a friend can help lighten the load, or at least foster empathy as we navigate tough situations. Consider this an invitation to let go of some of that weight.

Sunday, January 12th, 2025

Where am I playing the role of the victim?

It's easier to believe that life happens to us. If being an extra in a movie paid as much as a lead role, there would be less competition for the spotlight. The truth is, we are all the protagonists in our own lives. Whether we choose to be a hero, a bystander, or something in between is entirely up to us. However, we all have blind spots, and sometimes we're so caught up in the moment that we fail to see the bigger picture. Chances are, there's an opportunity or a crucial conversation we've been avoiding that needs to happen before we can move from the passenger seat to the driver’s seat.

Sunday, January 5th, 2025

What was the most significant positive event in my life in the last year?

Happy New Year!!

Something good happened in the past year. We made a meaningful memory, reached a milestone, or achieved something unexpected. Even if the entire year didn’t exceed our expectations, there were surely moments that stood out. Often, the most significant positive events happen to us spontaneously, without our control. However, that doesn’t mean we can’t intentionally plan for a significant positive event in the year ahead. Reflect on last year’s moment and identify the elements that made it both meaningful and positive to help plan something special for yourself, your friends, or your loved ones this year.

Sunday, December 29th, 2024

Did I set the right goals this year?

As the year comes to a close, how do you feel about your accomplishments? Goals serve as guidelines for the direction we want to move in, but at year’s end, we might not have achieved our specific goals and still feel accomplished. On the other hand, it's possible to meet our goals yet feel unfulfilled. In either case, there's an opportunity to reflect on what we truly value and gain insights to set more meaningful goals for the year ahead.

Sunday, December 15th, 2024

What inner-conflict am I suppressing?

Conscious, empathetic leadership requires a deep level of self-awareness and alignment with one’s true self. The saying "Heavy is the head that wears the crown" resonates across centuries because it speaks to the weight of responsibility leaders carry. In today’s fast-paced and high-pressure world, unresolved inner conflicts—whether they stem from values, identity, morality, or fear—can erode our decision-making and impact how we lead. By confronting these internal struggles, we open the door to greater emotional intelligence, allowing us to lead with clarity and purpose, even in the face of uncertainty.

Sunday, December 8th, 2024

What systems can I put in place that will channel my energy and time more efficiently?

Every now and then, our personal "operating systems" become outdated or inefficient. New opportunities for greater effectiveness and efficiency arise, but if we don’t pause to evaluate and refine how we operate, we risk wasting valuable time that could be spent serving others. More importantly, achieving ambitious goals requires thoughtful, long-term planning. While anyone can occasionally stumble upon success, consistent achievement demands strong habits and well-tuned systems. I encourage you to take a moment this week to assess what areas of your system need adjusting. Even a small, incremental change can lead to exponential results.

Sunday, December 1st, 2024

What myths am I perpetuating about my ability to multitask?

Let’s face it—today's workplace is obsessed with nonstop productivity. Despite countless time-saving advancements, we often prioritize increasing output over allowing ourselves more downtime. However, research is clear: multitasking reduces efficiency, increases errors, and leads to burnout, yet many of us still take pride in juggling multiple tasks at once. If we reconsider the myths of multitasking, we can create space for others to step up and for ourselves to focus on deep, meaningful work—proven to deliver higher-quality results.

Sunday, November 24th, 2024

What would happen if I set myself the target to speak only half as much as I do now?

There’s an old saying that reminds us we have two ears and one mouth, so we should listen twice as much as we speak. Years ago, while sitting at the Harvard Club, a role model of mine shared that same feedback with me. I remember feeling like a smaller version of myself for the rest of the conversation. As leaders, we know the power of listening—it drives collaboration, sparks innovation, and fosters inclusion. Yet, many of us still find it hard to surrender the microphone. This week, I challenge you to practice speaking less and listening more, even in small doses. When we do speak, our words will carry far more weight.

Sunday, November 17th, 2024

Who is my "good enough" role model?

As leaders, we must balance ambition with self-compassion—not only for ourselves but also for those who look to us for guidance. Social media and Forbes headlines constantly bombard us with unrealistic pressure to be perfect, to live up to idealized figures, and to lead without flaws. However, recognizing that a role model doesn’t have to be perfect, but simply "good enough," allows us to set realistic, attainable standards for ourselves and our teams. By prioritizing progress over perfection, we ground ourselves in more authentic leadership, fostering growth for everyone around us.

Sunday, November 3rd, 2024

Are my actions effectively communicating my main focus?

We always have a priority, whether we consciously acknowledge it or not. When we lack clarity on our priorities, we tend to drift. If we're fortunate, our subconscious takes over, and we still achieve our goals. However, imagine how much more effective we could be if those around us understood our main focus. Then, we'd have a supportive network working with us to achieve that focus - not just ourselves, but also others who could offer valuable support.

Fortunately, our actions can convey just as much information as our words. Take this opportunity to reflect on moments where you can take intentional action to signal to others what your main focus is right now.

• If you're job hunting, share your job search progress with others, including your networking efforts and job applications.
• If you're seeking a romantic partner, let friends and loved ones know that you're actively dating and what you're learning from the experience.\
• If you're working to increase revenue, communicate your key objectives and rally others behind you by being transparent about the actions you're taking to achieve them.

Sunday, October 27th, 2024

Which emotion do I need to confront?

Talking about feelings is a polarizing topic, especially in the workplace. One school of thought is that it builds trust and greater understanding, while the other school of thought is that sharing them could make work complicated. I'm not here to take a side. Instead, I invite you to reflect on your feelings this week.

We experience a range of emotions relating to ourselves, external events, and other people. If we don't process them, we may lash out because we've been bottling things up. We may also make unfair judgments due to preconceived notions or deprive ourselves of joy because we feel we should be sad to console others.

Our emotions significantly impact our leadership style and influence how we present ourselves to the world. It's essential to uncover if there's a dominant emotion that comes to mind right now and do the work to understand why we might be avoiding it.

Sunday, October 20th, 2024

Do my actions align with the three qualities I'd want my closest friend to associate with me?

In a previous newsletter on authenticity, we explored the paradox that arises when people ask us to be 'more authentic.' In essence, they want us to be ourselves, but this request overlooks the fact that we are constantly navigating between three versions of ourselves: our past self, present self, and future self. This week, let's focus on the self we aspire to be when we're with our closest friend. The question invites us to reflect on how we want to show up as a friend and whether we're actively living up to that aspiration. If it prompts a change in our actions or behavior, all the better.

Sunday, October 13th, 2024

What formative life lesson do I need to refresh?

One of my dear friends once rhetorically asked me why people wait for a 'come-to-Jesus moment' to make the changes they've known they needed to make for a while. He was referencing the challenging decisions, hard choices, and difficult conversations that we avoid at all costs - until a near-death or equally tragic experience forces us to take action. Think of a diabetic who refuses to cut out sugar until they survive a diabetic coma, an entrepreneur who can't reimagine their business model until they narrowly avoid bankruptcy, or an executive who can't prioritize their loved ones until they lose someone close to them.

In each case, tragedy serves as a trigger. But we don't need an unfortunate life circumstance to make the changes we know we need to improve our lives; we just need an intentional moment of consciousness. Find your moment this week.

Sunday, October 6th, 2024

Whose life do I secretly admire?

Former U.S. President Theodore Roosevelt once said, “Comparison is the thief of joy.” This quote resonates with me, but only if I view life as a competition with only one winner. In reality, life is more complex and multifaceted. When we compare ourselves to others, we often induce stress and confusion. But what if we could reframe our comparisons with a desire to learn?

For decades, sociologists have taught us that observation is a powerful tool for learning. This week, let's try comparing ourselves to others with gratitude for who they are and what they bring to the table. Take a moment to reflect on what you admire about someone's life. What is it about their experiences or accomplishments that resonates with you? If it's applicable, consider how you can take a step in a similar direction. After all, imitation is the sincerest form of flattery.

Sunday, September 22nd, 2024

What feels like fun to me, but work to others?

Mark Twain famously said, "Find a job you enjoy doing, and you will never have to work a day in your life." At some point, we've all either heard or believed this quote. I've done both. Reflecting on the past week, however, I've come to realize that despite my passion for my job, I still feel like I'm working. Perhaps Twain's words are better suited for end-of-life reflections, when the mundane aspects of even the most loved jobs fade into insignificance. While we may not love every aspect of our jobs, there are tasks that bring us joy, even if others might find them draining. This week presents an opportunity to reflect on our unique strengths and contributions, allowing us to share more of what we enjoy with the world.

Sunday, September 15th, 2024

What am I actively doing to quiet the negative thoughts in my head?

Our thoughts shape our behaviors, which in turn drive our actions. In previous newsletters, I've discussed the inner critic in our minds and Automatic Negative Thoughts (ANTs). When these two forces combine, we refer to it as "chatter." If left unaddressed, this chatter can overwhelm us and even lead to decision paralysis. It's important to recognize that failing to actively manage our chatter is, in itself, a decision to let it control us.

Sunday, September 8th, 2024

If my 13 year old self would ask me to do one thing, what would it be?

We often remember our firsts: the first all-nighter, the first drive, the first kiss, and the first year of our teenage lives. As a child, I held onto beliefs that friendships last forever, money solves all problems, and bad things don't happen to good people. I was naive and idealistic, but that idealism fueled my dreams. I believed that with hard work, I could escape the poverty of my childhood and provide a better life for my family - and that dream became a reality. Idealism can be a powerful spark for achievement, as every accomplishment starts with an idea. Before reality sets in, our imaginations run wild and we're more creative. Many things we now take for granted, like Uber rides, international flights, and overnight delivery, were once just fantasies. Reflect on the dreams of your younger self and tap into that creativity.

Sunday, Septemebr 1st, 2024

What can I routinely do more of that I am really good at?

It's no secret that operating in our weaknesses can be demoralizing. On the other hand, working to our strengths is energizing. Despite the virtual Peloton instructors' reminders that "I get to do this," I've had moments where it felt like an obligation. I've constructed a life that I wanted, with a job, family, and everything in between. To make it manageable, I routinized it to minimize mental effort and ensure I wouldn't forget or fall short on any obligations. However, I started to forget that I created this system because I wanted to. This week is about finding opportunities to refresh our system by injecting more of the things we’re really good at, ramping up our energy in the process.

Sunday, August 25th, 2024

Where do I need to peel back?

It's easier to get caught up in the momentum of our day-to-day lives and keep moving than to slow down and be still. Instead of fighting the friction that comes with sitting still, let's lean into the motion this week. There's likely an area of our lives that's begging for more attention: an unfinished project, a conversation that needs to take place, or a problem that needs solving. While time might be one reason we're putting it off, it's probably not the only reason. We might be lacking the necessary skills, the relationship may have soured, or we're simply stuck. Whatever the reason, it's unknown or unclear. Peeling back the layers creates an opportunity to investigate why, and flex our curiosity.

Sunday, August 11th, 2024

What is the most valuable use of my time right now?

Not everything we do is worth doing, and not everything worth doing is valuable to us. This is why some people make their beds in the morning while others let their cars fill up with junk. We know better, but making the bed isn’t as valuable to us as the time it would take to do it every morning. We also know that most results come from a few key decisions or decisive actions. If we think about the Pareto principle, it would mean that eighty percent of the results come from twenty percent of the actions. Life management starts with effective time management. In a previous newsletter, Jim Rohn reminded us that we can achieve anything with our lives as long as we manage our time in the right way.

Sunday, August 4th, 2024

What is something I would be proud to fail on?

We’re nearly two-thirds of the way through the year. At this point, any New Year’s resolution that isn’t top of mind is likely an afterthought. However, this doesn’t mean the year is over or that there isn’t time to accomplish something meaningful. Whatever comes to mind is probably the right thing to do, but fear is a real emotion and often gets in our way. I’m not saying everything we’re afraid of is exactly what we should do, but it is likely that one of those things on our list of fears is something we should tackle. Let’s lean into the one we would brag about failing at because it is worth the sacrifice and the effort to push past the potentially paralyzing fear that comes with the thought of it.

Sunday, July 28th, 2024

What could take the most significant relationship in my life from good to great?

We have many important things to do in our lives, such as taking care of our health, our families, and our careers. It’s not until we take a moment to measure the quality of our lives that we recognize the penultimate measure is heavily influenced by the satisfaction of our relationships. Whether this question inspires a spiritual relationship with God, a passionate relationship with your soulmate, or one with a dear loved one, there is always a little more that we can pour into the most important relationship in our life without any regret. Nurturing and tending to a good relationship almost always yields more than we imagine for our mental and physical health.

Sunday, July 21st, 2024

Do I have the right balance between motion and action?

Every year, I lead three book clubs at work, one each quarter except for the summer quarter, during which I encourage a free read. More often than not, we re-read the same books, extracting new insights or being reminded of key concepts. This past quarter, we re-read Atomic Habits, where the concept of motion and action inspired this week’s question. James Clear writes, “When you’re in motion, you’re planning and strategizing and learning. Those are all good things, but they don’t produce a result. Action is the type of behavior that will deliver an outcome.”

Sunday, July 14th, 2024

Where can I add to my life through subtraction?
 

Whenever I’m stuck at work or we hit a choke point—a place where there is so much pressure in the system that it becomes clogged and needs to be unclogged—we hold a problem-solving brainstorming session. These sessions usually generate a lot of ideas, some good and some not so good. Nonetheless, we leave the session with possible solutions. If they don’t work, we go back to the drawing board. Rarely do these sessions lead to long lists of things we need to stop doing or remove.

In both a short clip and a podcast I listened to, I was reminded that subtraction is one of the most powerful forms of addition we have access to. Unfortunately, it’s counterintuitive and, as a result, one of the most underutilized. This concept doesn’t just hold true in the workplace; it can be a powerful tool in our personal lives as well.

Sunday, June 30th, 2024 

What one line would I like to have written on my tombstone?

Question 50 marks a celebratory milestone! I extend my gratitude to all Loopers who have been on this journey with me, and I'd like to give a special shoutout to those who started with me on Question 1 – you know who you are! In commemoration of reaching number 50, I aim to delve even deeper.

The tombstone question has been a recurring theme throughout my life, and with each reflection, I've honed in on a clearer idea of what it means to me. Each time I've revisited it, I've gained clarity and reaffirmed what is important to me and what I am striving for. The numerous sacrifices I've made and continue to make now carry a renewed sense of purpose. Suddenly, I find myself feeling less regretful about the decisions I've made in the past and more resolved about the choices I will need to make in the future.

Sunday, June 23rd, 2024 

If I had six more hours in my day, how would I spend them?

Nothing in this world is more valuable than time. While many of us trade time for a salary or money, there is no amount of money that can extend our lives by a year, month, week, or day. Yet, many of us would agree that there are moments when we spend our time without considering whether we are wasting precious moments on people or projects that don’t fulfill us. One way to recognize what we need to stop doing is to give ourselves an expiration date. For some reason, when we understand how limited our time is, it becomes easier to be stringent about how we spend it. However, unless a doctor assigns us an end time, we likely won’t know. So, we’re left with another method: a hypothetical exercise that involves the addition of a significant amount of time. Once we determine what else we would do with the extra time we have, we can reassess what we could trade in our current schedule to have more of what we want.

Sunday, June 16th, 2024 

If I need a unit of resilience for every unit of ambition I have, am I in balance or deficit?

One of the revered traits of a leader is often their ambition. The drive to dream and the willingness to imagine more and pursue it often propel us into leadership positions in the first place. With proper guidance, ambition can be catalytic. However, left unchecked, ambition can lead to catastrophe. Understanding the source and quality of our fuel can provide critical insights into whether we have what it takes to complete what our ambition drives us to start. As much as possible, we want to avoid a situation where we are 'running on fumes.' Our ambition should drive us not drain us.

Sunday, June 9th, 2024

Am I mistaking listening with compliance?

Listening, truly listening to someone, not just hearing, is a challenging skill to master. Hearing allows us to replay what someone said if we're asked, while listening changes how we respond to what others say. We should all be familiar with the common phrase that suggests we have two ears and one mouth, meaning we should speak for half the time we listen or listen for double the amount of time that we speak. However, merely sitting in silence does not indicate engagement in active listening.

As a leader, mastering active listening is undeniably the most difficult skill. Often, by the time I finish speaking, I already have my next point ready to go. My momentary pause serves as an opportunity to gather my next thought to respond. If we are truly listening, then anything we have prepared to respond with likely isn’t exactly what we should say. However, there’s a fine and delicate line between listening and blindly following someone else's instructions. Ultimately, as a leader, you are responsible for making the final decisions. Simply doing exactly what someone else tells you to do may feel like an abdication of your responsibility. Therefore, we must find a way to strike a balance, empowering our teams while also propelling our organizations forward swiftly.

Sunday, June 2nd, 2024

Am I making allowance for mistakes and failures in my life?

We are often our own worst enemy when it comes to constructive criticism. Instead of taking steps to quiet the inner critic like we have in previous newsletters, this one is about taking a more proactive approach. The premise being that if we have created space and acceptance of some amount of failure, we will be able to recreate what success looks and feels like. Let's be clear: I'm not suggesting mediocrity. Falling a few points shy of 100 is pretty darn good, but falling a few points shy of 80 could feel pretty darn bad. Instead, I'm positing that we aim for an A instead of a 100. When I was in school, an A was a 93. Any straight A student knows that in order to get an A, you still had to aim for a 100 because if you aimed for a 93 and fell a few points short, then you missed your chance. And things happen. You have an off day. A trick question throws a wrench in the plan, or, my favorite, you get assigned a group project where everyone doesn't pull their weight. Creating some wiggle room for mistakes and failure could help us appreciate the success in the moment instead of having to wrestle our inner critic.

Sunday, May 19th, 2024

What one thing can I do to improve my evening routine?

If you're a night owl, last week's newsletter might have rubbed you the wrong way. It's true that some individuals thrive during the nighttime hours, and undoubtedly, many great creative works have been produced during the wee hours. During my high school and college years, I often found myself burning the midnight oil to complete papers and study. Although the science behind memory and cognition might have been working against me, I managed to get things done well, and my grades reflected my efforts.

Last week, I challenged our community to make one change to their morning routines, so it seems fitting to now challenge our evening routines. After all, how we end our night heavily influences whether the morning starts with a boost or becomes a complete bust. Similar to last week, let's focus on making just one change and stick with it for a few months until it becomes a habit before considering adding another adjustment.

Sunday, May 12th, 2024 

What one thing can I do to improve my morning routine?

There have been entire books dedicated to morning routines, with a commonly held belief that how we start our day sets the tone for the entire day. Undoubtedly, there's a wealth of science and research supporting this idea. Almost immediately after completing my undergraduate studies, I transitioned from being a night owl to embracing the early morning, perhaps akin to becoming a "morning bird" that catches the worm. A well-crafted morning routine comprises multiple rituals arranged in a sequence to optimize flow, reduce stress, and enhance productivity.

Attempting to transform our current routine into the ideal version overnight can be overwhelming and may result in significant setbacks. Instead, I encourage us to embrace the concept of "one" this week and stick with it for a few months until it becomes ingrained before considering adding another element.

Sunday, May 5th, 2024

Am I practicing what I preach?

Happy Cinco de Mayo to all who are celebrating!

This could be wishful thinking, but I believe most of us understand the distinction between right and wrong. We recognize the importance of establishing rules and adhering to them, whether formally through the legal system or informally through our values. As an educator, I understand that children communicate through their behavior. As an adult, I often find myself wishing people would simply follow my instructions – except when I prefer they understand my intentions because what I said wasn’t precisely what I meant. Confusing, isn't it?

Similarly, saying one thing and doing something entirely different is perplexing. Gandhi stumbled upon something profound when he said, “be the change you wish to see in the world.” We are accountable for exemplifying the behavior we wish to see in others. Let the rest follow suit. It’s crucial to pause occasionally and evaluate whether we are genuinely practicing what we preach, as actions speak louder than words. Perhaps, as adults, when we witness a child misbehaving, it should serve as a reminder to reflect on our own conduct as well.

Sunday, April 28th, 2024

Are my earliest memories of money influencing me in a way that serves me today?

A few weeks ago, I was having a conversation with a fellow Looper who is also our business banker. She asked my wife and me what we believe is the most important thing to building wealth. I didn't think she was asking about the specific process because there are so many ways to achieve it. Her answer? Time. My answer? Mindset. While this might be an oversimplification, if you don't believe something is possible, you're unlikely to put in the effort to figure out how to make it happen for yourself and your family. You can have all of the time in the world, you only benefit from compounding money if you have money to compound.

Many people I talk to have "secret desires" for their lives but are too afraid to share them with others because they doubt their ability to achieve them. Here's the truth: if we don't believe we can achieve something, it's highly probable that we won't. Not all of us grew up in environments where money was openly discussed. Our early experiences shape our relationship with money, which significantly influences our behaviors and how we approach various situations as leaders.

Sunday, April 21st, 2024

Why do I believe what I believe?

If you had asked me when I was a kid what my most important virtue was, I would have said equality—because I was the second oldest and wanted the same things as my older brother. If you had asked me in high school what my most important virtue was, I would have said truth—because I believed we should never lie. When I got to college, that virtue shifted to loyalty—because I thought it was okay if someone close to me needed to lie in order to protect me from something. Unfortunately, I don’t have any good examples, except if aliens were speaking to him and told him that if anyone found out about it, they would have to kill him; I would have appreciated him lying to spare my life.

Today, it isn’t any of those things. While they are still important, I noticed in my work and personal relationships that, absent this one virtue, the relationships could not work for me. That virtue is respect. What we believe matters, but why we believe it matters more because it influences our judgments and perceptions of the people and the world around us.

Sunday, April 7th, 2024

What am I most excited about this year?

A few weeks ago, I found myself at yet another event where I was part of a small group, and the icebreaker was this very question. Despite considering myself as someone leading an exciting life, managing a company, writing newsletters, and occasionally traveling, I found myself at a loss. Fortunately, the presentation started before I had to come up with a response. Reflecting on the day, I realized I couldn't figure out what I would have said in the moment or even what I would say now that I knew the question for a few hours.

The level of excitement we attribute to something is less about the thing itself and more about our values at that particular moment in our lives. Two individuals can witness the same event and react in entirely different ways. Take roller coasters, for instance – one person may vehemently refuse, while another anticipates it with excitement. Beyond merely pinpointing what excites us, it's valuable to take a moment to clarify and understand why we feel excited about it in the first place. This introspection may provide insights into our values and help us better understand ourselves. At the very least, it can serve as a meaningful check-in question when engaging with a friend, direct report, or manager in the coming week.

Sunday, March 31st, 2024

For me, what is the difference between success and significance?

Who doesn’t love a little alliteration? The initial similarity between "success" and "significance" masks a deeper distinction once we substituting "importance" for "significance" the question then becomes: What truly matters, achieving personal goals or leaving a lasting impact?

While "success" and "significance" sound similar, they differ greatly. Success is about short-term goals, while significance is about lasting impact. Leaders often chase success, but true fulfillment lies in pursuing significance, leaving a positive legacy beyond immediate achievements. This requires a broader perspective, considering the impact on others. By understanding this distinction, we can communicate a more compelling vision and create a ripple effect of positive change.

Sunday, March 24th, 2024

In what ways might the way I work bring about the outcomes I most fear?

We all have imperfect work tendencies. For some of us, it may be the way we communicate with our co-workers, while for others, it may be our inability to stop working. I know I have been guilty of it. I often share thoughts like, "If I just get this one additional thing done," or one of my favorites, "This is really going to help so many other people," to validate my inability to stop working. Consequently, when I attempt to take a break, my mind races the entire time. My inner voice pushes me to return to work, arguing that I would be more productive and could act on those thoughts.

Most of the time, the way we work doesn’t matter too much unless it interferes with what is truly important to us. Discovering my life purpose at 18 years old was both a blessing and a curse. The most important thing to me is being able to look back at the end of my life and say that I was a great husband and father. Naturally, my biggest fear is working my way out of realizing that. The more I confront this fear, the more intentional I can be about ensuring it doesn’t come to fruition.

Sunday, March 17th, 2024

How can I spend more time playing the big version of myself this year?

About a month ago, I read one of James Clear’s weekly newsletters. He concluded by asking his readers to imagine two versions of themselves: a small version and a big version. Clear suggested that our behavior reflects the version we are currently embodying. For instance, when playing small, our behavior tends to be timid, accompanied by feelings of inadequacy. We often find ourselves surrounded by people and tasks that drain our energy. On the contrary, when playing big, our behavior exudes confidence, we feel motivated, and we tend to invest our time in people and tasks that energize us.

Initially, I interpreted this question as being related to business deals. However, after sitting with the question for a bit I realized its implications for relationships and life experiences. This served as a moment for reevaluation, prompting us to confront short-term fears and assess our relationships and work. It encourages us to discern what is serving us positively and what is not.

Sunday, March 10th, 2024

What is the difference between the person I feel I am and the person I want others to believe I am?

In the era of office debates, the notion of authenticity couldn't be more important. I've been in rooms with leaders publicly declaring "remote forever" to their teams, only to discover behind closed doors they're plotting to backtrack on promises and secretly monitor their team's work. Both actions undermine trust. However, we also understand that few things can be spoken about definitively. Words like "never," "always," and "forever" require caution. What might start as a harmless exploration, sowing only small seeds of distrust, could quickly spiral to a point where we don't trust the person looking back at us in the mirror.

The infamous notion that perception is reality isn't just a saying; it highlights the disconnect between our intentions and our actual impact. Understanding the contrast between who we are and who we want others to perceive us as is pivotal for our leadership. Reflecting on this difference helps us identify our true motivations, leading to authentic actions and communication. Authenticity becomes a key identifier, ensuring that we're not suppressing our true selves for external validation. Embracing both our real and projected selves fosters self-love and confidence.

Remember, authenticity is a journey, not a destination. We need to embrace imperfections and regularly check in with ourselves to ensure ongoing alignment with our true selves.

Sunday, February 25th, 2024

What is one thing I would do this year if I wasn't afraid to fail?

At the end of last month, I found myself at a dinner party where the organizer posed a question to the group. After overcoming the initial mental block and nearly convincing myself that I had no fears for the coming year, it suddenly struck me. However, I hesitated and wasn't certain if I wanted to share my thoughts.

As we went around the table, one person at a time, I began to normalize my 'one thing.' Although we won't have the benefit of a communal group sharing, verbalizing 'my thing' brought it to life.

Mark Twain aptly expressed the concept when he said, “Courage is not the absence of fear. It is acting in spite of it.” I remained just as fearful when sharing my thoughts aloud, but bringing the idea to the surface allowed me to explore with curiosity the underlying causes of my fear. Once I unpacked the fear, I started to list and contemplate the right ways to mitigate my fears. The question unlocked the door I had previously closed for myself. While I acknowledge that it will take more effort to fully open that door, the opportunity exists solely because of this question.

Sunday, February 18th, 2024

What beliefs do I have about getting others to do things?

Imagine waking up one morning completely self-sufficient. We farm our food, stitch our clothes, and even create our soap. Perhaps that's an extreme example, but it highlights the truth: we are incredibly interdependent. Our daily lives require countless interactions with others, and these interactions go beyond simple transactions. Often, the exchange is more intricate than simply swiping a card to settle the balance with our money.

The way we approach these interactions, motivated by our underlying beliefs about getting others to do things, shapes how we lead, collaborate, and build connections, both at home and in the workplace. Taking some time to reflect on these motivations and beliefs can significantly improve our ability to work effectively with others and foster strong, genuine relationships.

Sunday, February 11th, 2024

If a miracle solved your biggest problem, what would you be doing differently?

One of the resources from last week’s reflection reminded us that we all have a 'sad story,' regardless of our background or walk of life. It was not meant to downplay the fact that some of us face greater challenges than others, but rather a reminder that, no matter what we see on the outside, no one’s life is perfect. When I was in college, a wealthy mentor reminded me that all men put on their pants in the same way: one leg followed by the other.

Growing up poor, I was intimidated by wealthy people. The pants categorization humanized the affluent for me in a way that didn’t make me feel like the 'other.' Today, I know that everyone struggles and has their own problems to deal with. Instead of ignoring this reality, I believe it's a perfectly constructive way to address the thoughts lingering in the back of our minds. Consider this permission to follow Einstein’s wisdom: 'If I had an hour to solve a problem, I'd spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.' Remember, everything is figureoutable - when we have the right problem.

Sunday, February 4th, 2024

Where are the bright spots in my life?

What we appreciate, appreciates. This principle holds true not only with our thoughts but also in our relationships and the way we spend our time. Showing appreciation involves cultivating an attitude of gratitude and intentional care, magnifying our awareness of the existence of the things we value, drawing them into sharper focus. Gratitude, however, proves elusive when it is most needed—during challenging times."

As leaders, one of our significant opportunities during challenging times lies in identifying what is already working well and using it as a foundation to build momentum or replicate for scale. Recognizing the bright spots in our lives makes it easier to observe similar positive aspects elsewhere. Consider this a rendition on focusing on our strengths instead of commiserating over our weaknesses.

Sunday, January 28th, 2024

What are the costs of my perfectionism?

I didn’t always care about striving for perfection. In fact, I hated the idea of writing a draft of anything—let alone editing or rewriting something. Then I started to write. Not casually write—seriously write. First, social media posts; then blogs, articles, and finally, books. The more I tried to write, the more I recognized the importance of reading. Before I knew it, I was a writing snob—critiquing pieces, highlighting typos, and judging other people’s art. This wouldn’t normally have been a problem, except I noticed myself gradually raising the standards for everything I did and for everyone I spent my time with. I couldn’t stomach the idea of another random reader or beneficiary of anything I was putting out into the world critiquing and judging my work, or even worse, me.

Perfectionism can be a double-edged sword. While it may drive us to achieve high standards, it can also lead to stress, burnout, and a constant sense of dissatisfaction. In other words, it comes at a cost. By reflecting on our perfectionism, we can begin to chip away at the negative aspects and cultivate a healthier and more fulfilling way of living. Constantly reminding ourselves that progress, not perfection, is the key to a thriving life.

Sunday, January 14th, 2024

Am I effectively assertive?

If you're passive-aggressive, you won't command others' respect. On the flip side, being aggressive-aggressive earns you a reputation as a bully—someone people don't want to work with, let alone work for. Effectively asserting yourself involves finding the sweet spot between passivity and unnecessary aggression.

As a manager or leader, assertiveness means openly and honestly expressing your thoughts, feelings, and needs while respecting others. It requires standing up for yourself without veering into aggression or passivity. Reflecting on your assertiveness is crucial; it helps you understand your communication style, identify areas for improvement, build stronger relationships, and navigate situations more effectively.

Sunday, January 7th, 2024

What inspires me without the need for self-criticism?

Happy New Year!

We begin something, gain momentum with it, and excel at it. Yet, suddenly we find ourselves questioning our progress, losing motivation, wondering, "Why am I doing this?" We've all been there. The allure of achieving our goals, the initial excitement, and even validation from our peers initially propelled us forward. When that fades, we often resort to self-criticism and condemnation to keep going.

Recognizing a moment for self-reflection and recalibration doesn't require failure or hitting roadblocks. As the adage goes, the only constant in life is change. Let this liberate us to evolve our approach to anything we're deeply involved in, be it our career or a long-term project. Now, more than ever, might be the perfect time to embrace our curiosity so we can feel like you're driving down a hill instead of up one.

Sunday, December 31st, 2023

Where is my mindset limiting my growth?

Happy New Year’s Eve!

Our mindset can either fuel our pursuit of goals with unwavering determination or hinder our progress towards achieving our full potential. Two common attitudes that can slow our learning are: 1) the know-it-all approach, where expertise may lead to a belief that improvement is unnecessary, and 2) a limited belief in one's ability to learn, characterized by a fixed mindset.

The common misconception is that individuals are either know-it-alls or not, and they either have a fixed or growth mindset. In reality, we can hold all four attitudes simultaneously. For instance, we may adopt a know-it-all approach to tying our shoes while recognizing there's more to learn about different sneakers for enhanced comfort. Similarly, we may exhibit a growth mindset when learning about AI but have a fixed mindset when delving into blockchain.

Sunday, December 24th, 2023

What am I doing differently as a result of what I learned in the past year?

Happy Holidays!

We are constantly bombarded with a lot of information, ideas, and insights. While some of these are beneficial for us, others may be more suitable for different individuals. As the year starts to wind down, we have the chance to reflect on our achievements and extract valuable lessons from any setbacks we’ve encountered.

One of my favorite misattributed quotes is that 'knowledge is power.' However, knowledge in itself isn’t power—acting on that knowledge is. This principle also applies to our learning experiences. If we don’t change our behavior in response to what we claim to have learned, then we haven't truly learned anything. Let’s take some time this week to contemplate and internalize the lessons you're carrying from 2023 into 2024.

Sunday, December 17th, 2023

What does "wealth" mean to me now?

Wealth is usually thought of as having a lot of money or valuable things. But what it really means to us might be much more. It could be about having enough money, good health, strong relationships, fun experiences, and feeling like we're doing something important. As we grow and change, our idea of wealth might change too, and that's totally fine. The key is to think about what wealth means to us right now and make choices that fit with what we believe in. This way of thinking helps us set goals and make decisions, especially about money. It also makes us feel good about our life and leads to choices that are good for others too. Understanding our own idea of wealth helps us deal with changes in life and stay strong during tough times. In the end, thinking about what wealth means to us helps guide us to live a life that's true to ourselves and fulfilling now.

Sunday, December 3rd, 2023

What labels am I carrying with me that need to be let go of?

Labels can have a significant impact on our lives. They can shape our thoughts, feelings, and behaviors in both positive and negative ways. Positive labels can boost our self-esteem and motivate us to achieve our goals. For example, if we are labeled as "smart" or "talented," we may be more likely to believe in ourselves and take on new challenges. Negative labels, on the other hand, can be harmful to our mental health and well-being. If we are labeled as "lazy," "stupid," or "unattractive," we may start to believe these things about ourselves and develop negative self-concepts. This can lead to anxiety, depression, and other mental health problems.

Even labels that seem neutral can have a negative impact on our lives. For example, if we are labeled as "introverted" or "extroverted," we may start to feel like we have to fit into those boxes. This can limit our personal growth and development. Reflecting on the labels we carry and choosing to let go of those that don't serve us is a transformative process. It enables personal growth, fosters mental well-being, and promotes genuine interactions in our relationships.

Sunday, November 26th, 2023

Is everything that's truly important to me scheduled on my calendar?

Food, family, and football are highlights of this time of year. When I read reflections from adults in hospice, they never express regrets about not working enough. Instead, they often wish they had spent more time with loved ones, pursued a dream or passion, and used their time more intentionally. A fulfilling life is essentially a series of well-lived days, weeks, months, and years.

If you're reading this, chances are you're not in hospice, and time remains on your side. Perhaps after work, you have ample time; it's just a matter of commitment. For me, what's on my calendar gets accomplished. This week, take a moment to reflect: are the things you value and deem important present on your weekly calendar? This could be family dinners, reading time, workouts, dates, or exploration.

Sunday, November 19th, 2023

Is my life path aligned with my deep desires?

We often begin our journeys fueled by passion. Stumbling upon a job that resonates deeply, it feels as if the stars have aligned. What more could one want than to earn a living doing what they adore? But, as with all things, time brings change. The initial joy and wonder wane, replaced by a subtle yet persistent feeling of unease. The strange part? On the surface, everything remains the same – the job, our commitment, even our skills.

Yet, beneath this facade lies the culprit: a growing misalignment between our deep-seated desires and our daily actions. During the initial euphoria, we might have missed or dismissed certain desires or aspirations. As time progresses, these overlooked feelings start to surface, creating that discomfort. It's a crossroads of sorts – do we adapt our aspirations or pivot our profession? Ignoring this misalignment can have consequences. Left unchecked, it might culminate in a sudden and drastic shift, filled with the bitterness of hindsight. It's essential to periodically check-in, ensuring our path still aligns with our heart's true north.

Sunday, November 12th, 2023

Am I aging well?

In the grand journey of life, the mantra seems clear: work hard, care harder. You've probably heard stories about people who were strong but their minds got tired, or their minds were good but their bodies gave up. If you're reading this, it's likely because you like taking care of your mind by learning new things. Every day you're alive, you're getting older, and that's a good thing. Thinking about how we're getting older is like stopping at a gas station during a road trip to check if our car is doing okay. It's a chance to look at different parts of our life—like how healthy we are, how we feel mentally, our relationships, and if we feel happy with our lives. And, it's also a good reason to feel proud of the wisdom that comes with getting older!

Sunday, November 5th, 2023

What am I carrying that I need to let go of now?

Every single one of us has emotional baggage. No one is exempt. No one is weird because of it. We all carry stuff in our minds and hearts, like bad thoughts, old problems, or bad friendships. When we think about what we should let go of, it's like realizing what's stopping us from feeling better. Once we figure that out, we can start doing something about it. It might mean changing how we act, setting new rules for ourselves, or talking to someone who can help. Getting rid of this stuff can be tough, but it's super important for us to grow and be happy.

Imagine if you had a backpack full of heavy rocks; it would be hard to walk, right? Well, those rocks are like our emotional baggage. When we drop them, it's like getting rid of the heavy stuff, and suddenly, we can move more easily. We also get to be ourselves and feel happier. It's like clearing a path for good things to come our way. Unfortunately, getting rid of baggage isn’t a one and done thing. It is a lifelong process. Instead of trying to clear out all of your baggage, focus on the biggest rock in your bag at the moment.

Sunday, October 29th, 2023

Are you playing to win or are you playing not to lose?

Your mindset influences your behavior. Your collective behaviors influence your outcomes. When you are playing to win, you are focused on achieving your goals and objectives. You are willing to take risks and put in the hard work necessary to succeed. You are also more likely to be creative and innovative in your approach. It is important to note that there is a difference between playing to win and being reckless. When you are playing to win, you are still taking calculated risks. You are also willing to learn from your mistakes. Conversely, when you are playing not to lose, you are focused on avoiding mistakes and protecting yourself from failure. You may be more cautious and risk-averse. As a result, you may miss out on opportunities to grow and succeed. Take the time to identify your mindset and approach to life.

Sunday, October 22nd, 2023

Am I doing "the work" because I'm committed or inspired?

Understanding your motivation behind the work you do is essential for living a fulfilling life. Commitment and inspiration are two different driving forces, and knowing which one fuels your efforts can provide a clearer sense of direction in your work and life. Commitment is a steady, reliable force that keeps you going even when things are tough. Inspiration is a more fleeting emotion that can provide bursts of energy and creativity. If you are committed to your work, you are more likely to push through challenges and setbacks. If you are inspired by your work, you may approach tasks with greater creativity and innovation.

The ideal balance of commitment and inspiration is different for everyone. Some people thrive on the challenge of committed work, while others need the spark of inspiration to stay motivated. If you are not feeling committed or inspired by your work, it may be a sign that you need to make a change. This could mean changing your job, starting your own business, or finding a new way to do your current job that is more meaningful to you.

Sunday, October 15th, 2023

How is my self-judgment getting in my way?

Self-judgment can be a major obstacle to our happiness and success. When we judge ourselves harshly, it can lead to feelings of low self-worth, anxiety, and depression. It can also prevent us from taking risks, trying new things, and living our lives to the fullest. Reflecting on how our self-judgment is getting in our way can help us to become more aware of the negative impact it is having on our lives.

Sunday, October 8th, 2023

What is the source of my self-esteem?

Our self-esteem is shaped by a variety of factors, including our childhood experiences, our relationships with others, and our own thoughts and beliefs about ourselves. When we reflect on the source of our self-esteem, we can begin to identify the specific factors that have contributed to our current level of self-worth. If our self-esteem relies heavily on external validation, such as praise from others or material success, we may have a less resilient sense of self-worth.

People with a well-founded, internal source of self-esteem tend to be more resilient in the face of adversity. When our self-esteem is based on qualities and values that are intrinsic to us, it's less likely to be shaken by external setbacks or criticism. Reflecting on the source of our self-esteem can help us identify and address any negative thought patterns or beliefs that may be undermining our self-worth.

Sunday, October 1st, 2023

If the future me looked back, what memory from now would bring me the most joy?  

What if the memory that brings you the most joy when you look back at your life in the future is something you could be savoring more of now? When you take the time to think about what memories you would want to cherish in the future, it can help you to appreciate the good things that are happening in your life right now. Elevating your awareness of the good things in the present moment gives you double the reward: you get to enjoy the joy of the moment now, and you get to experience the joy of nostalgia when you reflect on this time in the future. You might even be inspired to document this time in your life with photos or writings, so that you can evoke the positive emotions you're experiencing today in the future. This will turn your memories into a gift that keeps on giving.

Sunday, September 24th, 2023

What does being "whole" look and feel like for me?

High achievers often focus on what is not going well instead of taking stock of what is going well. This may be because it is human nature to do the same when it comes to our health. We notice when we are in pain or hungry because our bodies send us signals that something is wrong. The same is true when we feel like something is missing or not right in our lives.

We have an opportunity to reframe our perspective. What if, instead of focusing on what is missing from our lives, we could take a moment to step back from the pain and envision what it would look like to be "whole"? Instead of trying to fill a void, we could envision the aspirational version of ourselves and work towards that? There is no one answer to the question of what it means to be "whole." It is different for everyone. I invite you to explore the look and feel of wholeness with me this week.

Sunday, September 17th, 2023

Where can I benefit most from a beginner's mindset?

When we grant ourselves the opportunity to experience 'beginner’s luck,' we welcome one of the fundamental elements of accelerated learning into our lives: play. Embracing the role of a beginner allows us to make mistakes, experience failures, conduct experiments, and attempt once more without the weight of judgment. No one anticipates perfection from a novice. Regrettably, we frequently become entangled in superficial standards that we wouldn't impose on others who are just commencing their learning journey. Consequently, we deny ourselves the chance to explore something new. By moving forward devoid of the beginner's mindset, we forego the opportunity to draw upon our community or network for support in our learning, benefiting from their wisdom and experience.

Sunday, September 10th, 2023

Where do I need to set stronger boundaries?

Our needs and priorities change over time. What we were willing to tolerate in the past may no longer be acceptable to us now. The only constant in life is change. If we’re not actively evaluating and adjusting our boundaries we’re more likely to be overwhelmed by others’ demands, lose our sense of self, and fail to maintain relationships that are mutually respectful and supportive. When we’re able to maintain healthy boundaries, we’re better able to protect our time and energy for the things in our lives that we say are important to us (i.e. family, friendships, writing, etc.).

Sunday, September 3rd, 2023

Which insecurities are currently influencing my behaviors the most?

Ever thought about why you act the way you do? Well, figuring out which worries bug you the most is like discovering your superhero origin story. When you know what's making you feel unsure or not-so-great about yourself, it's like shining a light on those sneaky shadows in your mind. This helps you make better choices, feel happier, and be more awesome in your relationships and dreams. We all have many insecurities that influence our behavior. They typically operate in our subconscious mind. Reflecting on our insecurities allows us to take a big step toward feeling better and becoming the superhero of our own lives!

Sunday, August 27th, 2023

What are my current blind spots?

We all have blind spots, areas where we are unaware of our own biases, limitations, and assumptions. These hidden gaps in our awareness can hinder progress, limit potential, lead to missed opportunities, and even lead us to make bad decisions. By acknowledging we have blind spots and spending some time to understand what they are, we are taking a step towards a heightened self-awareness that empowers us to make informed decisions, adapt effectively, and continually evolve. Embracing our blind spots fosters a proactive mindset, enabling us to navigate challenges, enhance skills, and ultimately achieve our goals with greater clarity and purpose.

Sunday, August 20th, 2023

What can I find hope in again, even if I once thought it was hopeless?

Our mind is powerful. In the same way it can convince us that something is possible, it can also get us to believe that something we were excited about and thought was worth doing is no longer possible or worth doing. This question introduces a mindful intention behind that limiting belief. Take a moment to identify things that are still worth fighting for, rediscover your sense of agency, build resilience, confront past struggles, and embrace the possibility of a brighter future.

Sunday, August 13th, 2023

What impact is my environment having on my goals?

After setting goals and intentions, it’s important to assess whether your environment is inhibiting your ability to achieve them. How you set up your life, home, and routine can make all the difference between achieving your goals with the wind in your sails or feeling like you’re running up a never-ending hill. Do you have scoreboards in places you’re checking? Do you have your goals in places you can’t avoid seeing them? Have you told your inner circle of friends and family members what you’re after? Take a moment to evaluate the conditions you’re working in and allow the environment to work with you in achieving your goals and intentions.

Sunday, August 6th, 2023

What are my current goals and life intentions?

Do you want to learn about yourself? Set three to five goals that are important to you. It will give you a sneak peek into what you value. If you don’t like goals, you’re not alone. A lot of people hate setting them because they don’t know how to set them right or never follow through on them, so what’s the point? The point is that if you don’t have a goal or an intention, you likely don’t have a direction, taking meaning out of your days. More importantly, you’re depriving yourself of valuable learning. When you set goals, you understand what is important to you. When you fall short on a goal, you have an opportunity to reflect and learn why. And when you set a goal you do nothing with, you learn about something else in your life that you thought was important but isn’t.

Sunday, July 30th, 2023

What do I need to water in my life?

Start - Stop - Continue. Three areas that are at the core of all constructive feedback and good reflection. Except “continue” is often forgotten. I find myself falling victim to starting more projects, habits, and hobbies than I can count. When I’m overwhelmed, tired, or just looking to change it up, I quickly find myself on the other side of that equation cutting things out, ending projects, killing habits that are harder to follow through on. In the constant shuffle it is easy to overlook the areas in our lives where we’ve planted good seeds, but haven’t been back to water them in a while whether they be old writing or important relationships in our lives.

Sunday, July 23rd, 2023

What am I really good at?

We all have strengths and skills that we’re naturally better at than others - whether it is because we were more inclined to develop them or we grew in an environment that cultivated them at an early age. Just because you can learn any skill doesn’t necessarily mean you’d enjoy the learning journey or that learning the skill is the best use of your time. We know developing our strengths happens faster than working on our weaknesses because of the relationship between enjoyment and learning. Knowing our strengths allows us to focus on the things we’re really good at, to signal where we belong on teams, and to steer away from jobs, projects, and effort on things that will drain us.

Sunday, July 16th, 2023

What are the most important problems in my personal life?

Separating what is urgent from what is important is a tall task. Often, the important things are sitting in the back of your mind. Important things surface and disappear because we get distracted by the urgent things or the fires we have to put out. Unfortunately, tending only to the urgent things will keep us stuck in the same place. We’re treading water instead of swimming.

Problems also present opportunities. Use this moment to bring the important personal problem to light and commit to doing one thing to address it by yourself or with the support of others around you. View the problem as an opportunity to grow and find the good that can come from addressing the important, not just the urgent.

Sunday, July 9th, 2023

How do I know if I'm winning or losing on a daily, weekly, monthly or annual basis?

As you get older, you recognize that failure is finite and objective (i.e. failing out of school, bankruptcy, death, etc.), but success and winning are more subjective. You can make a lot of money and be unhappy. Your relationship looks good in photos but you feel like something is missing. Over time, I’ve learned that having clarity on our values (what we really think is important, not what other people think is important), creating goals that are aligned with those values, and achieving those goals is the ultimate success.

Sunday, July 2nd, 2023

Where do I find meaning and inspiration when I need it?

We all encounter moments when we feel stuck, lacking motivation, direction, and our usual energy. It is crucial to be able to identify when we are in such a situation and know where to seek help. Instead of waiting until we are already in a rut, it is essential to proactively discover what inspires us and keep a record of it. This way, we can speed up the process of overcoming the inevitable low points we all go through.

Sunday, June 25th, 2023

Who Do I Want To Be A Hero To?

Life is a fleeting journey, and when we take a moment to reflect, we realize that it is composed of years, months, weeks, days, hours, minutes, and seconds. As humans, we naturally seek social connections, and the quality of those connections profoundly impacts our happiness and sense of self-worth. Often, without even realizing it, we seek approval from others. However, it is important to understand whose approval truly matters to us and whose does not.

Warren Buffett, when asked about measuring a successful life, eloquently stated that it lies in whether the people we want to love us actually do. Once we identify those who matter to us, we can:

• Create value for them with our time, knowledge, and resources.
• Make them the driving force behind our goals.
• Prioritize our relationships accordingly.
• Adjust how we spend our time to be more present for those who matter.
• Limit or eliminate time spent with people who don't hold significance in our lives.

The term "hero" refers not to someone in need of rescue, but rather to the people we aspire to support, protect, influence, uplift, and serve as role models for.

Sunday, June 18th, 2023

What Do I Want From Life?

Sometimes, it's effortless to get carried away and simply go through the routines of life. Whether we realize it or not, we are always discovering new things about ourselves and the world around us. As we gain knowledge, we also transform as individuals, and our desires change along with us. However, if we don't consciously pause and reflect on our desires, we miss out on the best way to achieve them. It's crucial to identify and name our wants to have a better chance of satisfying them.