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Justin Wright

Weekly Recap - Week of 12.20.21

published5 months ago
5 min read

Happy Monday!

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This week we are dealing with hard conversations: the kind of conversations that put a knot in your stomach and make you run for the hills.

As a brief disclaimer: any links for items, books, etc. that are available for purchase are done through an affiliate program. This means that I get paid a small pittance of money for everything you buy using my links. I don't recommend things I haven't read/used, so using these links helps me out and gets you great products!


Hard Conversations

Tim Ferris believes that your success in life is directly proportional to the number of hard conversations that you're willing to have. Hard conversations can range from breaking up with a bad partner, to asking for a raise, to confronting a friend who is impacting your happiness, to explaining why you want to work at a gym instead of taking that high-paying finance job when your mom asks what you're doing with your life (totally not based off personal experience). Why then, do we often avoid these conversations like the plague?

There are a number of factors at play here, fear being a dominant one. We've discussed the impacts of fear in previous newsletters, but it does play a large role in our avoidance of difficult conversations. What if they react poorly? Will it cost me my job? Will it cost me this friendship? What will people think of me?

The key to any hard conversation is two-fold. First, understand what you want, and understand what they want. If you aren't clear on these two things, it's difficult to articulate what you need and why you need those things to happen. Secondly, you must understand why both parties want those things. This is a cheat code for any tough conversation, especially as emotions run high; taking a step back to understand what is motivating the person on the other side can help you shift focus and navigate the situation more fluidly.

Empathy, Empathy, Empathy

Understanding the why is crucial, because it helps us connect to the other person as a human being. If you ask your boss for a raise and they say no, that doesn't mean they want you to fail and are intentionally sabotaging you. Maybe they are facing budget cuts and, instead of letting people go, are trying to cut costs elsewhere. Maybe you're in line for a raise in the near future as part of a larger group of promotions. Maybe they weren't aware that you were responsible for several recent successful projects, and can be swayed once confronted with this information.

If you immediately think of the person you are speaking with as an enemy, it's easy for emotion to take over. Try and shift your perspective to better understand the reason behind their viewpoint. What drives their beliefs is infinitely more important than the beliefs themselves. Most people are struggling enough to manage their own lives and have limited bandwidth to be fully aware of others.

Mind, Not Heart

Once you better understand your counterpart's motivations, focus on diffusing the situation by dealing with things intellectually. In the above example, if your boss is hesitant to give you a raise due to budget constraints, outline how you are providing additional value or saving the company money elsewhere. If you can make an intellectual argument for the benefits you are providing, it becomes harder for your boss to argue these facts.

So many times we approach hard conversations with a defensive mentality instead of a collaborative mentality. The end goal of any conversation is for both parties to get what they want, or for both parties to ultimately agree on the best course of action. This type of debate requires collaboration, not divisiveness. Focus on the details instead of focusing on the person; you can disagree with what someone is saying without attacking that individual's character.

Create a Sense of Safety

The best way to navigate hard conversations is to create a sense of safety for all involved. When power dynamics are at play (like a boss and their employees), this is typically the responsibility of the person with more power. Either way, in order for an honest conversation to flow, the participants must feel safe to share their viewpoints honestly. A conversation cannot be effective unless all pertinent information is out in the open. If participants don't feel safe to share, some information will always remain obscured and it becomes difficult to arrive at a meaningful solution.

Hard conversations will never stop being hard, but if you arm yourself with the right perspective then they become more approachable. Avoiding these conversations entirely is a surefire way to make them worse, and frequently avoiding challenging conversations is a recipe for stagnation and unhappiness. The next time you are faced with a hard conversation, rip the bandaid off and go for it! Just remember to focus on the what and why of each participant, empathize with them as a human being, speak from your mind and not from your heart, and aim to create a safe environment for open dialogue.


Hit List

The most interesting things I've read, heard, or encountered this week:

Speaking of Hard Conversations: Crucial Conversations by Patterson et al.

This book is essentially the handbook for how to have hard conversations. The authors describe any "crucial" conversation as one in which emotion is heightened and the stakes are high. Aside from having good, actionable advice, the book also provides countless real-world examples to help you better understand its key points.

The worst dining experience ever: We Eat at the Worst Michelin Starred Restaurant Ever by The Everywhereist (originally linked in The Morning Brew newsletter)

This article made me experience a wide range of emotions; I laughed, I gasped, I read on in horror like a car accident you can't look away from. Eating dinner out with friends is one of my favorite activities, and I can only imagine experiencing something like this. An excerpt to tickle your fancy: "Another course – a citrus foam – was served in a plaster cast of the chef’s mouth. Absent utensils, we were told to lick it out of the chef’s mouth in a scene that I’m pretty sure was stolen from an eastern European horror film."

What I'm Watching: The Alpinist on Netflix

Boy am I a sucker for a great documentary, and The Alpinist is an EXCELLENT example. Without ruining the story, the film chronicles the exploits of Marc-André Leclerc, a young and talented mountain climber. If you liked Free Solo, The Alpinist dials up the anxiety level a few notches higher.

A tea I've been enjoying: Tulsi Sleep and Tulsi Ashwagandha teas by Organic India

I was put on to Organic India tea by a close friend of mine who practices body work and is extremely knowledgeable in the realms of health and wellness. He told me this particular combo of their Sleep and Ashwagandha teas was incredible, and he wasn't lying. This is one of my favorite pre-bed cocktails. If you want to go down the rabbit hole, the company's founder has contributed some pretty interesting research/content to the health and wellness worlds also.

Mental Health and Wellbeing: The Ballerina Mindset by Good Morning America (YouTube)

I stumbled across this video and many of its messages resonated with me. Megan Fairchild, a professional ballet dancer in New York, has been advocating for mental health awareness among high-performing young adults. She recently authored a book which explores concepts around finding balance in success, such as knowing when to push and when to rest. Learning to be okay with varied levels of performance and being able to ease off the gas and relax is incredibly important for those type A people in your life.


That will do it for this week! Please let me know what you liked, didn't like, and what you want to see more of. Do you want it to be longer, shorter? Do you want specific topics covered more? Less? Have a wonderful week, and remember to please forward this to your friends -- helping get the word out and get more eyes on this newsletter is hugely helpful and greatly appreciated!


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