“Time. Space. Reality. It's a prism of endless possibility, where a single choice can branch out into infinite realities, creating alternate worlds from the ones you know.”
-The Watcher from Marvel’s MCU Animated Series “What If?”
Marvel's animated show "What If?" tantalizes fans with alternate realities, exploring how different choices could have led to vastly different outcomes. In one of my favorites, T’Challa (Black Panther) becomes Star Lord resulting in an entirely new and more heroic timeline for characters like Thanos (the super villain) and Yondu. It is also one of Chadwick Boseman’s last performances before his untimely death, making it extra special.
This “What If” concept, while wildly entertaining in a superhero context1, can also be a powerful tool for appreciation and introspection in our own lives.
Leadership principle: Persist in gratitude.
You may be thinking: “Oh jeez…a thought piece on gratitude during Thanksgiving week in the U.S.…how original (NOT!)” If so, I dare you to keep reading.
In this week’s Friday Reflection, I want to introduce you to a practice called "What If" Gratitude. This four-step process deepens our sense of gratitude AND also highlights the often-overlooked divine providence and people who've shaped our journey.
Step 1: Identify One Keystone of Gratitude
Begin by pinpointing one thing in your life for which you are deeply grateful. This could be a relationship, an experience, a career achievement, a personal growth moment, or even a state of mind that you cherish. The important thing is this keystone of gratitude is something that makes you feel a deep sense of thankfulness,
Step 2: Trace the Inflection Points
Reflect on 3-5 crucial decisions and moments that led you to this keystone of gratitude. Consider: had you or someone else made a different choice at any of these junctions, you might not have this precious element in your life today. These inflection points are the crossroads where your path could have diverged significantly and as a result, you may have missed out on enjoying this keystone of gratitude.
Step 3: Acknowledge the Beacons
Now, think about the people (“beacons”) who influenced or guided you at these inflection points towards the path that ultimately led to your keystone of gratitude. These might be family members, friends, mentors, colleagues or even enemies whose words or actions had a meaningful impact. Recognize how their presence in your life at those critical moments helped guide you toward your keystone of gratitude.
Step 4: Express Targeted Gratitude
Pinpoint the specific reasons for your gratitude towards each beacon you identified. This isn’t just a general thank you; it's an acknowledgment of the specific ways in which they contributed to your journey. Perhaps it was advice, a word of encouragement, a challenging question, an attribute they demonstrated or even a just serving as a role model. This step not only deepens your sense of gratitude towards these individuals, but also reinforces your understanding of how they've shaped your path.
I developed this exercise, because while the evidence of the benefits of gratitude are abundantly clear, many leaders struggle to consistently practice it and reap these benefits.2 As a result, we need to find ways to keep it fresh…to persist in gratitude.
Here’s an example of my own: One keystone of gratitude for me is my two amazing children: my daughter Alicia and my son Julián. They bring such goodness and delight to my life.
Four important inflection points (among many others) are 1) my birth 2) moving to New York City after college, 3) taking a job at Bronx Lab School, and 4) taking a leap of faith in my career.
Inflection 1: I almost didn’t make it into the world. In fact, while pregnant with me, my mom was told she had miscarried by one doctor. I am eternally grateful that a close family friend, Pat, encouraged my mom to get a second opinion…and thankfully the second doctor detected my heartbeat and several months later, I was born. Without Pat’s optimism and steadfastness, I wouldn’t be on the planet to enjoy moments of love with my kids.
Inflection 2: I was planning to either move back to LA or to DC after college. Toward the end of my senior year, I started dating someone who was moving to New York, and this relationship influenced my decision to change my top location preference for Teach for America from LA to NYC. In a twist of fate, we broke up only a few months after moving here. But if we hadn’t dated, there’s a good chance I would not have moved to NYC. I am grateful for the time we did have together3 and it’s hard to fathom not having moved to NYC, because it’s been my home for nearly 20 years and the backdrop for so many of the special times with my family.
Inflection 3: I had two job offers at new schools after teaching for two years and ultimately, chose to work at Bronx Lab School4 to start an English as a Second Language program. I turned down an opportunity at an amazing school where two of my close friends worked. This proved quite the monumental choice, because one of my fellow teachers at Bronx Lab, Eric, invited me to his jazz concert. That night at Eric’s show I met a spirited and inquisitive woman, brimming with passion and resilience. This woman is now my wife and best friend, Alex. Without Eric’s friendship and musical gift, Alex and Alicia would never have entered my life and Julián would not exist.
Inflection 4: My initial reluctance to leave Bain5, a company that I greatly enjoyed, led me to turn down an offer from ghSMART, only to reconsider after receiving a persuasive email from Elena, now an esteemed mentor and friend. Her insights, coupled with further reflection and advice from trusted confidants, led me to ultimately accept the ghSMART offer.6 The new role opened doors to more autonomy over my time, which has allowed me to fuse what seemed like opposite goals for me: be a present, loving dad and realize my ambition to have an outsize impact on making the world a healthier, balanced and more positive place through leadership. I am grateful for Elena’s persistence and her ability to see a vision for me that I couldn’t fully picture at the time. As a result, I get to be the kind of dad I want to be for Alicia and Julián.
I share these inflection points as examples. There are many others that if they had gone a different direction, I would not have Alicia and/or Julián in my life.
What I hope you see is that “What If” gratitude does more than just foster a deeper sense of thankfulness. It illuminates the interconnectedness of our lives, the pivotal role of human relationships, and the often fortuitous nature of our paths. In recognizing the 'what ifs,' we learn to appreciate not just the outcome, but the journey and the people we encounter along the way.
So, as you experiment with this practice, you might just find that this practice not only gives you another tool to persist in gratitude, but also gives you a profound appreciation for the intricate tapestry of your life's story.
Take Action: Practical and Proven Steps
Make “What If” gratitude a ritual. Set aside 15 minutes once a month to do this practice. You can choose the same “one thing” or different things each month. You can also vary which inflection points you hone in on. For example, you could focus on a specific decade in your life that had many inflection points or you could zoom out and try to identify the most critical ones. Make this ritual a date in your calendar. I also find it is best to write it out in a journal or on a piece of paper vs. just contemplate it.
Express appreciation directly to the people you identify. A few weeks ago, this practice prompted me to send a simple “thinking of you and thank you” email to someone I hadn’t spoken with in over a decade. She responded within hours and it meant so much to her. Your note, call or text doesn’t need to be perfect. Just send one.
Identify your “gratitude interlude.” For me, this is quite literal. When I need a dose of gratitude during the day, I’ll play the song “Love Yourz” by J.Cole. If you are less of a music head, then maybe it’s a quote, mantra or poem. One of my favorite quotes on gratitude that I recently came across: “Wear gratitude like a cloak and it will feed every corner of your life.” These little interludes of gratitude can re-invoke the feelings generated by more focused gratitude practice like “What If?” gratitude.
Reflect: Some Questions to Consider
What is one “keystone of gratitude” for you?
When can you experiment with “What If?” gratitude this week?
What could help remind you to do this experiment, especially given how busy the end of year period can be?
If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.
In the words of Kendrick, “Don’t judge me!” Yes - I am 41 year old, “serious” professional who is unafraid to profess his love for an animated Disney+ show. I know there are more of us out there. And just last week, they dropped the trailer for “What If?” Season 2. Get hype!
This piece highlights at least four benefits that are grounded in cognitive science. 1. Gratitude “releases dopamine and serotonin, the two crucial neurotransmitters responsible for our emotions, and they make us feel ‘good’. 2. Gratitude helps to build and sustain strong social bonds. 3. Gratitude helps regulate stress and is a natural antidote to anxiety and depression. 4. Gratitude has physical benefits - playing a role in improving sleep and reducing pain.
If I were advising my younger self, I probably would have said that a college relationship is NOT a solid decision criteria for a major career choice (ha!).
Bronx Lab was a really special place for me (and I imagine still is) - strong leadership, dedicated, skilled and fun teachers and an amazing group of students, a subset of whom I am still in touch with nearly 20 years later. I can list at least 15 people from this one year of my life that have had a meaningful impact on me.
Bain is also special place. It accelerated my career in ways I couldn’t have imagined and blessed me with many lifelong relationships. Though I had other challenging jobs previously, I believe that spending nearly a decade at Bain unlocked another gear in me.