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The TGC Blog

  • Writer: Tamar Gaffin-Cahn
    Tamar Gaffin-Cahn
  • Apr 27
  • 3 min read
Smiling at F*ckup Night


Humans are meaning makers. We make meaning of the stars, loss, life, and failure. But our brains also crave the binary; however, the binary does not exist in totality because we are all different. Now what? This newsletter shares different ways to sit in the discomfort to heal, make meaning, or make decisions in your own life. 


What I'm Reading

This month, I finished the book Nightfaring: In Search of the Disappearing Darkness by Megan Eaves-Egenes, a fascinating nonfiction account by a travel writer who advocates for less light pollution to (re)connect with the stars and learn what darkness can teach us. She discusses the power of night and the necessary natural movements of animals and nature. She writes: 


Valerio and I discussed how the merits of wolf rewilding have been hotly debated, and many people remain staunchly opposed. But he told me research shows time and again that predators are crucial to ecosystems, precisely because they inspire fear. Apex Predators like wolves are sometimes called keystone species because they change the behavioral and grazing patterns of their prey, like elk, which in turn affects the growth patterns of shrubs, grasses, and trees that the elk browse on. These patterns have a domino effect across the food web, known as a cascade. To take an example: Wolves were killed off in Yellowstone National Park in the 1920s, and studies following their successful reintroduction in 1995, more than seventy years later, have shown astonishing ripple effects. The wolves curtailed excess populations of elk, which allowed willow, aspen, and cottonwood trees to regrow. The renewed presence of willow stands provided ample sturdy wood for beaver families and songbirds to repopulate. Beaver dams positively affected springwater runoff, and the trees provided needed shade for aquatic populations. The effects went on and on down the cascade. Ecologists call this the "ecology of fear," and the way that predators affect species and fora distribution are "landscapes of fear.”


“Ecology of Fear” sounds terrifying, to be honest, but let’s look at what fear can teach us and do for us, because sometimes we need a little fire under our ass. Adding the right amount of pressure or fear can get us out of our comfort zone into our learning zone. By fear, I don’t mean a free-range apex predator in your bedroom; I mean, time pressure or doing something you’ve never done before, or even a fear of failure. Has fear ever gotten your gears going, and what has been the positive ripple effect? 



What I'm Listening To

In a world of ghosting, by employers or in romance, filled with unanswered questions, ranging from the tragedy of a disappearing loved one to an unexplained breakup, we are often sitting in “ambiguous loss.” Over a delicious lunch, with a long-term, almost-Rabbi friend, we discussed acceptance of breakups when we’d never really get the answer. The pain of “what could have been” torments us in the waking moments of each day. We discussed “closure” and “resolve” as the final stage of grief, but are they? Spoiler: they’re not, as the grief process isn’t linear, nor cyclical. 


My friend shared an episode of the On Being with Krista Tippett podcast featuring an interview with Pauline Boss, who coined the term “ambiguous loss.” Boss has worked with families of people who disappeared on flights to divorced couples. Ambiguous loss is a way to debunk the grief process, find meaning, and navigate hardships connected to the unknown.


Have a listen on Apple Podcasts.


What I'm Doing

F*ckup Nights Boston is officially looking for sponsorships! Do you have a business or organization that believes in the power of failing? Do you want to connect with a community-focused, growing movement in Boston that cares about no-bullsh*t, honest conversations? We want to connect! Email us at boston@fvckupnights.com.


What's Moved Me

The psychologist Abraham Maslow on maturity:


"The most mature human beings are also childlike. That is not as contradictory as it sounds. The most mature people are the ones who can have the most fun.


They are able to regress at will; they can become childish and play with children and be close to them. It is no accident, I think, that children generally tend to like them and get along with them.


Involuntary regression is, of course, a very dangerous thing, but voluntary regression seems to be characteristic of very healthy people."


Source: Emotional Blocks to Creativity


What I'm Wiggling To

This is my recent song to listen to on repeat. Along with a bit of sunshine, this song has helped me pull myself out of seasonal depression (then Noah Kahan’s new album put me right back in).




Stay Playful,

Tamar

 
 
  • Writer: Tamar Gaffin-Cahn
    Tamar Gaffin-Cahn
  • Mar 30
  • 4 min read
Smiling at F*ckup Night


What I'm Reading

In the leadership course I teach to Graduate students at Emerson College, we obviously focus on the skillsets of being a leader, but we don’t always play the role of a leader; sometimes, we’re the follower. As a follower, what do I need to succeed? According to Gallup, followers need four elements from their leaders: trust, compassion, stability, and hope. Defining the roles is imperative to a successful leader-follower relationship.


Similarly, in a coaching relationship, the relationship is best when roles are clearly defined. The following article, How to Be a Great Coaching Client by Deborah Grayson Riegel, breaks down the role into the following parts:


  1. Bring a goal, not a complaint.

  2. Do the homework.

  3. Own the coaching relationship.


This isn’t just for coaching clients. This is relevant in your relationship with a supervisor, mentor, or maybe even romantic partner. How can you bring these elements into your relationships?



What I'm Listening To

This month, I listened to Mel Robbins’ podcast, How to Design Your Life in 1 Hour, with guests Bill Burnett and Dave Evans (links below). 


What is Life Design?

Life Design is a creative problem-solving approach that originated from Design Thinking. Alongside activities for every step of the design process, it shifts mindsets from dysfunctional beliefs to curiosity, self-understanding, brainstorming, and experimentation. Rinse and repeat. 


A client of mine is approaching their annual review at work, and for their homework, I gave them The Odyssey Plan, an activity that asks them to create several life plans for the next five years. This will help them decide on which path to advocate for in their review. There are two key elements to this plan. 


First, rank the plan 1-10 in the following categories:

  • How coherent is this plan?

  • How confident are you in this plan?

  • How much would you actually like this plan?

  • How resourced are you in this plan?


Second, and arguably the most important: what questions do you have about the plan? This is the moment when you shift from an inward question to an outward one. Get curious, ask people. Get the questions answered by many people and then do a gut check and reassess. Again, this is about constant iteration. Rinse and repeat.


This activity is not just for when you have no idea what path to take, but it’s also helpful when you’re excited about many options and need to make a decision.


The point is: we all have multiple lives to live. You can always redesign your life. With that in mind, what are you curious about for the next thing? What excites you now? It’s guaranteed to change, so focus on this moment.


To get a personalized Odyssey Plan for you, respond to this email with either the following:

I feel stuck between a few pathways: [list 2-3 options]. OR I have no idea what the next five years look like.


Find the podcast on YouTube, Apple Podcasts, or Spotify.


What I'm Doing

F*ckup Nights Boston VOL III SOLD OUT! Wow. Three events, three sold-out venues, 75+ people each. I started FuN in Boston because I thought it was a fun, punchy, “lean in” type of event. What I didn’t expect was the honor of delicately holding the emotions and experiences as our speakers shared their stories with us for the first time. Many have cried, recounting the broken friendships, the shame of not being able to hold their end of a deal, and subsequently putting loved ones in financial risk, or letting their ego hold onto an idea of who they are, just wasn’t working. 

 

Our failures are often in that category because of the emotion tied to the actions. Speakers share how cathartic their experience is, from sharing the rough presentation with Sam (my co-lead) and me to event day, when they share it in front of 75+ people. It’s vulnerable, it’s courageous, and it’s moved me to be part of their journey.

 

Volume IV is live: Thursday, May 28, 2026, at Trident Booksellers! Get your tickets today.



What's Moved Me

We all know Maslow’s Hierarchy of Needs, but in his final years, he changed his tune. In his diaries, he discussed a higher level beyond self-actualization that is still based in the ego. Maslow introduced the concept of self-transcendence, as a person’s ability to obtain a unitive consciousness with other humans (1964; 1968).


When we design a life for ourselves, based on our values in relation to others and the community, and on an impact on our world, we’re achieving a level of self-transcendence. 


According to Venter (2017), the transcended person can view the world and their purpose in it in relation to other human beings on a more global scale and is aware that they can have an impact not just within their own geographical boundaries but on the whole world. Maslow (1973) postulated that one main characteristic of self-transcended people is autonomy and independence from culture and environment. They do not need the approval of others; their opinions are not formed in light of their immediate circumstances. Maslow held that self-transcendence is reached when a person seeks to further a cause beyond the self and to experience a communion beyond the boundaries of the self (1968).


At the end of the day, it really is all about the people.


Venter, Henry. (2017). Self-Transcendence: Maslow’s Answer to Cultural Closeness. Journal of Innovation Management. 4. 3-7. 10.24840/2183-0606_004.004_0002.


What I'm Wiggling To

This past month, I saw one of my favorite artists, Amber Mark. In her most recent album, she’s collaborated with the one and only Anderson.Paak for Don’t Remind Me. Try not to bop your head and foot for this chorus.



Stay Playful,

Tamar

 
 
  • Writer: Tamar Gaffin-Cahn
    Tamar Gaffin-Cahn
  • Feb 27
  • 5 min read
Smiling at F*ckup Night


What I'm Reading

This month, I challenge you to choose to see the good. 


Yes, it’s a pain in the ass to shovel out your car.

Yes, it’s near impossible to work from home when your kids have a snow day.

You can’t control the weather, but you can control how you make meaning of the chaos. 


Shoveling is hard, and it’s exercise.

Can’t get work done, and you get to witness your kids (finally) having a snow day after years of virtual learning.


Here, you’re gifted opportunities to reframe the chaos into goodness. I was reminded of this when reading The Place of All Possibility: Cultivating Creativity Through Ancient Jewish Wisdom by Adina Allen.


Turning chaos into goodness is an act of creativity; it’s meaning-making. How can you take the chaos and use creativity to make meaning into something good?



What I'm Listening To

If you love thinking about the meaning of life, this podcast is for you. Three big thinkers: Bill Burnett and Dave Evans, authors of Designing Your Life, out of Stanford University, and Bob Waldinger, psychiatrist, psychoanalyst, and Zen priest of Harvard University, discuss student questions about the meaning of life, or rather, the meaning of your life, and how to find that. Here are my takeaways. What are yours?


  • Life is the story we tell ourselves (plus the experiences)

  • Buddhist saying: How do you know if the water is warm? You have to experience it.

  • Alignment Coherency = What I am + What I believe + What I do

  • Question: How do you get rid of all the noise around you? Answer: An old Cherokee man told his grandson, "Inside each of us, there is a battle between two wolves. One is evil—it is anger, envy, greed, arrogance, and ego. The other is good—it is joy, peace, love, hope, humility, and kindness." The grandson asked, "Which one wins?" The elder replied, "The one you feed."

  • There are Resume Values and Eulogy Values. Which of your behaviors align with each?

  • There is primary pain (physical pain) and secondary pain (pain, frustration, annoyance of the experience of pain). One lasts a lot longer.

  • The common Buddhist saying, "Life is Suffering," can be translated as "Life is Unsatisfactory." With this new version, how you see life is through expectation and perspective. 

  • You can’t hear yourself by yourself.


Watch or listen here:

You Can Design Meaning Right NOW: Bob Waldinger, MD, Harvard & Bill Burnett and Dave Evans, Stanford



What I'm Doing

Do you actually want to change? What’s your intuition saying? Or is part of you more comfortable staying where you are, even if that means holding onto frustration or slipping into a victim mindset?

 

It's a hard question, I know.

 

We might choose the familiar, even when it’s not working, because the unknown feels riskier. Jumping without seeing the ground is terrifying.

 

This month, I’m focusing on a bias toward action. Nothing extreme, just choosing movement over hesitation. It might be trying a new coffee order, asking your boss for what you need, or finally booking the trip. For me, it’s been asking for help with hard decisions.

 

We hold onto emotions longer than we need to. Ask yourself: Do I want to keep carrying this? Sometimes the answer is yes, and that’s okay. Some feelings need time. But staying there is still a choice. 

 

Notice when you start telling yourself the same story or making excuses. I can’t spend five minutes editing my resume. I can’t find five people to ask for a career conversation. Pause and ground yourself.

 

Focus more on alignment; does this behavior match your values? When your actions don’t match your values, you can feel the disconnect. That tension is useful because it’s pointing you toward something that matters. Instead of explaining it away, ask: what value is underneath this, and how can I honor it with action? If a friend hurts you, the deeper value is honesty or support. What would actually move you closer to that kind of relationship?

 

Less overthinking. More choosing. Then moving.



What's Moved Me

It’s with deep, deep sadness that I share the passing of the most impactful mentor throughout my life, Leslie Sholl Jaffe, pictured above. I met Leslie when I first realized I wanted to be a coach and was researching the profession. We scheduled a 30-minute call, but we ended up talking for nearly two hours. She was far more than any professional title or word could describe. Beloved by all, she was one of those people who knew, knew me, knew suffering and pain, knew joy and happiness, and would guide me through mine. I cried during every call we had because she could see right into my soul. She was willing to mentor me in retirement, purely because she liked me. How lucky am I?

 

She helped me grieve the loss of a close friend by validating my experiences with her visiting me from the other world and sharing how to stay connected to people who are no longer physically here. She helped me navigate life’s complex emotions and how we feel about ourselves as those emotions change us. She helped me heal my inner child during a painful breakup of a friendship. We discussed leadership, coaching, and the art of guiding people to be their best and most authentic selves. She spent her time walking the walk with me, leading by example, the best kind of learning. 


I visited her at her home in Austin, TX, in April 2024. It was the only time I met her in person. We spent all day together, talking, laughing, sharing life stories, crying, learning, and growing. It was, and is, a profound example of the beauty of an intergenerational friendship. In her retirement, she started making jewelry. That day, we designed a necklace for me that I’ve worn every day since it arrived in my mailbox.


We have lost a profound teacher. I'm devastated that I can no longer learn from her. And yet, she is a blessing; her memory is a blessing; and I am heartbroken and ever so grateful.


What I'm Wiggling To

Noah Kahan’s new song, The Great Divide. It’s about a childhood friendship lost and refound, about mental illness and loneliness. In early February, I had the privilege of traveling to Brazil to officiate a high school friend’s wedding. I ended up having a painful conversation with a friend who, without acknowledging, is heartbroken by the loss of friendships from our younger days. We have two choices when these moments happen: accept or work to rebuild the relationship. If one doesn’t work, try the other, but there is still a choice. 


The third option, regardless of outcome, is to wish this person well. As Noah Kahan says,


I hope you settle down, I hope you marry rich

I hope you’re scared of only ordinary shit

Like murderers and ghosts and cancer on your skin

And not your soul, and what he might do with it.



Stay Playful,

Tamar

 
 

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