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Lessons Learned and Leadership Challenges (Part II)

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A year ago, I shared three lessons learned in 2022 and three leadership challenges for 2023. At the very least, it was a helpful exercise for me, so I’ll give it another go. 

Lessons Learned

Talk to people

If you need to talk to a person, talk. I cannot fathom how much time is wasted playing email or text ping-pong. While it might seem like the safer option, having a meaningful or difficult conversation in this way is silly. There’s something exhilarating about dialing a number and rolling the dice––or, heaven forbid, meeting face-to-face. Worst case scenario, the other person screams at you for a hot minute, and you get a fun story out of it. Best case, and more often than not, the actual case, they thank you for taking the time to talk. 

Be grateful for challenges

Reframing setbacks as beneficial challenges makes all the difference in the game of life. Somewhere along the way, many of us have been lulled into thinking that we should strive for a life without difficulty and conflict. If not lulled, then perhaps we have been spurred to a furious battle against evil until no conflict remains. Either way, fixed mindsets, fanaticism, and pessimism are becoming dangerously vogue. Challenge leads to growth, and it does not require the absence of joy. 

Beware the cognitive triangle

I wrote about the practicality of sustaining alignment as opposed to juggling the work-life balance model. In that piece, I discussed the cognitive triangle: our thoughts, feelings, and behaviors influence each other. We should be mindful of this relationship, especially when at least one leg of the triangle is out of positive alignment. It is reasonable to have off days, but a consistently negative experience is an unfortunate way to spend a short and miraculous existence. To avoid being trapped in a negative mindset, there may be no greater investment than training the mind. I said I would report back with my thoughts on Sam Harris’ Waking Up app: it was the best investment I made in 2023 for my personal growth and mental health––and, most likely, will continue to be in 2024. Here’s a 30-day guest pass if you’re interested in checking it out (no credit card required, and I don’t get any bonus for you signing up). 

Leadership Challenges

Check attachments 

Attachment, by definition, isn’t necessarily bad. Nonetheless, it’s good practice to investigate attachments to ideas, feelings, objects, people, whatever. Let’s consider the popular fitness wearable Whoop. There’s a lot of good that can come from understanding your fitness and being motivated to maintain a healthy lifestyle. It’s also possible to develop an unhealthy attachment to fitness and health. Whoop says, “We obsess over building the world’s best wearable so that you can obsess over what matters most: you.” I’m not convinced that self-obsession is a desirable attachment. Whether it be to the self, anger, a creature comfort, or even justice, I believe we ought to examine what we feel attached to. Check the facts, think critically, evaluate the impact on behavior, and decide if energy is being well spent and achieving desired results. If proper analysis finds no issues, keep calm and carry on.  

Cue it up 

I need reminders. I set digital reminders all the time, to remember to cancel a subscription, to order Thai food, to attend a meeting. I don’t have as many cues reminding me how I want to live, and that seems like a challenge worth pursuing. Like many people, I can get swept up in the noise around me. I would benefit from daily reminders like this could be my last day on earth, or billions of people would love to trade places with me, or blaming others for my experience is a counterproductive exercise. If I am willing to read hundreds of “reminders” in my inbox each week, I certainly can find the time and space for a few cues on how I want to live. 

Practice a philosophy of life 

William Irvine discusses the importance of having a philosophy of life in A Guide to the Good Life: The Ancient Art of Stoic Joy. Naturally, he promotes Stoicism, though he also recognizes that there are other alternatives and that not all people will make a good Stoic. In any case, I agree that practicing a philosophy of life is a smart idea––and so is cueing up that philosophy with reminders, habits, or rituals. Successful individuals and cultures do this. It helps them maintain their heading while others get lost in the shallow echo chambers of social media or the deepening maelstroms of righteous indignation. The war for attention shows no sign of letting up, so it’s wise to be prepared.


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