Feeling Lighter

“We delight in the beauty of the butterfly, but rarely admit the changes it has gone through to achieve that beauty.” ~Maya Angelou

“Investing in yourself is the best investment you will ever make. It will not only improve your life, it will improve the lives of all those around you.” ~Robin Sharma, The Monk Who Sold His Ferrari

Anna asked me to do a vision exercise. I loathe writing about the future and where I think I will be in five, ten, or fifteen years. If you would’ve asked me a decade ago if I thought I’d be where I am now, I would have said, “Hell no!” But, with help and coaching, I’m feeling lighter, and not solely existing as the underdog…I have a more hopeful perspective and more intentionality on the places I can go.

For the last few months, I’ve been getting better at paying attention. I know that sounds simple, but in today’s world – an endless array of TikTok videos, Twitter, and the excessive use of emojis to communicate, y’all know I still prefer long prose – shoutout to Dr. B! As Morgan Housel writes in Attention, “Getting people’s attention has never been easy, but social media made it a nightmare. Someone reading a book 20 years ago had few other distractions in front of them. Today your phone offers an Olympic competition for your dopamine.” While this is true, my dopamine particularly increases when I engage with people; more specifically, real, thought-provoking, intellectually stimulating conversations. You can’t get that from mindless social media scrolling. It also increases when I get the sense that the universe is putting someone or something in my life for a reason – so that’s why I pay attention.

On Nov 22nd, I was walking down from my new office building when a familiar face passed by me. I said: “Anna?” A confident question. My voice lilted on the last “A” just in case it wasn’t her…The woman stopped, turned around, and said something along the lines of, “Sean, Oh my gosh, hi!” I had only seen Anna a handful of times in my life, and I couldn’t tell you about the last time prior to this run-in. She was in from Chicago with her husband for Thanksgiving. I told her how I had recently gotten married, honeymooned, and started a new gig. She told me about her marriage, how she and her husband (who was standing there) were doing great and how life was generally good. We must’ve talked for a maximum of five minutes, but it felt like two friends making up for lost time. We hugged it out and went our respective ways. It felt good to have taken the chance to connect with another human being, randomly, right outside of Grand Central Station.

A few weeks later, I received a text: “Hi Sean! It’s Anna Laifer. It was so lovely to run into you in NYC. I am excited to hear how things are going and congrats on your new role! I’m not sure if you know this already – but I am a leadership coach and work with a range of clients often during transition points – new roles, new jobs, starting their own company, becoming a father, etc. After I ran into you and you mentioned it’s been an adjustment to your new role, I thought I’d follow up to see if I can be helpful in some way. If you’re up for it, I’d love to jump on a call and discuss. Obviously, no pressure, but I thought I’d offer this up and see! Let me know. Either way it was so lovely to see you!” That was a Friday—the following Monday we had our intro call. 

On the intro call we dove deeper than the Grand Central run-in, but even after that there was still so much more to the iceberg. We discussed my previous work with executive coaches (I have multiple), therapy, going to Onsite in September, etc. But it was during this conversation that Anna said something that I’ll never forget. While I described feeling “free” and “liberated” in my new role, she asked: “How does it feel to be lighter?” I was standing with my air pods in as she asked the question, but my proverbial knees buckled. It wasn’t a difficult question, but she knows how to work with people going through transition, and it forced me to recalibrate. I was no longer sneaking up on people; instead, I was expected to lead from the front. I was no longer fighting to gain access to “the room”; I had a seat at the table. I was transitioning from surviving and existing to thriving and being. The question had so much baked into it – it forced me to grapple with the responsibilities that come with success and agency. I knew how to fly beneath the radar or deal with the internalized bigotry of low expectations. But this was different. Whether she knew it or not, I felt as though something in my spirit had been cracked open. I felt like I was going through a metamorphosis of sorts, a caterpillar evolving into a butterfly or a snake shedding its skin to become a newer version of itself. It felt good. It felt earned. But it was also terrifying.

I have long dealt with adversity, even making things up in my head like Jordan in the Last Dance, always needing a villain to conquer. But as many different mentors and muses have told me throughout my career progression, that little voice in your head never truly goes away. You just learn how to deal with it better (read: differently, as I’m sure this is unique to each person). Or as Rue, quoting Greg LeMond, said to me once, comparing this phenomenon to cycling, “It never gets easier, you just go faster.”

So as hyped as I was to have had that conversation, when I got this text on Dec 16th, “I’m thinking about having you do a bit of pre-work before our Wed session. Can you carve out about 30-40 min for that? If so, I’ll send it over later today!” I felt some type of way. I was excited, but I was also wondering, what was I really committing to? It’s one thing to have these conversations, or these thoughts, and then move on. It’s a completely different thing to show up and put in the work. This new work with Anna required me to write, to see my thoughts and shadow work materialized. I was juxtaposing my skill in intellectualizing emotions versus my ability to actually work through them. So back to where we began, Anna’s vision exercise… 

Simply put, I did not want to do it. I often struggle when Lindsey, my wife, asks me where I want to be in five, ten, or fifteen years. I struggle to dream big. I can think outside of the box to solve a pressing issue, but I can’t sit still to dream about all that I could potentially do in this world. I often busied myself with work so that I didn’t have to do it. Whether consciously or subconsciously, I’d long been content with simply being at a certain place, or a certain level. There were also various times where I struggled with imposter syndrome, only to have that term quickly removed from my vocabulary when a mentor told me that imposter syndrome was created by white men in the 1970’s to stunt white women’s professional growth by causing them to doubt their abilities and feel like frauds. Throw in class, race, sexuality, etc. and you have a strong, difficult cocktail.

I procrastinated. I actively thought about not writing! 30 minutes?! Ain’t nobody got time to sit down for 30 minutes and contemplate what life will be like in fifteen years. And as much as I claim to believe in the power of manifestation and visualization, I don’t know that I’ve always done the necessary work to actually bring certain thoughts to fruition. But it starts with paying attention.

Nonetheless, I jotted down a few notes on the printout of the exercise, thinking I’d come back to it and use that as my foundation from which to write my real work. The morning of our meeting, I still hadn’t written one word. As I looked around my apartment for the sheet with my notes, I realized that I was doing it again – thinking about the work or planning to do the work rather than simply doing it. I reprinted the email with the exercise and wrote twelve minutes at the top. “It’s not 30-40, but hey, it’s better than nothing,” I thought. I started the stopwatch on my phone, then flipped it over so that I couldn’t see it; it’d check back in twelve minutes or so. I put in ear plugs and then started pounding away on my keyboard… “The future is now…It’s Dec 21st, 2037, and I’m living in New York with Lindsey and our three children: two boys and a girl. It’s winter and Christmas is right around the corner...” I was moving. I was in flow. I wasn’t worried about grammar or diction or punctuation or syntax. I was getting my Anne Lamott SUSDAT (Shut Up Sit Down And Type) on and it felt good. I flipped the phone over after some time— the stopwatch read: 20 min 14 secs…And I could’ve kept going…

The conversation that ensued with Anna later that day gave me a dopamine rush. It came from revelation, from connection, from a mental expansion of my capabilities – healthy dopamine. So that is why the MML on Dec 23rd ended the way it did:

“I had one of those conversations this week. You know, the ones that you continue grappling with long after it’s over, and for the best of reasons. I had finished a session with [one of] my executive coach[es] and I was energized afterwards. The revelations, the goosebumps, the insights, the candor. We out here just trying to get better. Nonetheless, it’s been used before, but this quote came up during the session. So, sharing with y’all :).

‘Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, ‘Who am I to be brilliant, gorgeous, talented, fabulous?’ Actually, who are you not to be? You are a child of God. Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It’s not just in some of us; it’s in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.’ ~Marianne Williamson, A Return to Love: Reflections on the Principles of A Course in Miracles”

Now you too have gotten to see more of the iceberg as I’ve begun paying more attention. I’m learning how to dream big versus struggle through a dream deferred. Time, effort, reps, and failure have taught me that I’m not inadequate. It’s time to start living, trusting that maybe the reason why I’m fearful of writing is because I’m powerful beyond measure. I just gotta keep paying attention. 

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And while this truly isn’t meant to be a testimonial, to the extent you’re curious about how to get to the next level, Anna’s website here and LinkedIn here . *Note* Mindfulness is the foundation for all her work. She meets each person where they are and creates a custom coaching relationship that best supports them. Schedule a no-commitment, exploratory conversation here or reach out to her at anna@annabo.co with questions.