Photo by Alex Radelich on Unsplash

Transformational Leadership – GAP Community

I recently attended Transformational Leadership, a training hosted by GAP Community. I learned a ton volunteering to help set it up, which you can read about here.

I’m only going to write about a few of my key conceptual takeaways. A huge portion of the value came from workshopping various exercises with fellow participants. Rather than describing them and ruining the fun for anyone who’s considering but hasn’t been yet, I’ll tell you what I got from them.

“Vision” is a way of being, not doing.

When most people think of “Vision”, they imagine a strategic 5-year plan to achieve certain goals.

“My vision is to run a $10M tech startup in Chicago, marry a quality partner, and start a great family.”

Those goals are valuable, and should be pursued. But the question we must ask ourselves when contemplating vision is:

“How would I have to BE in order to achieve my goals?” What virtues would I need to possess, how would I have to show up in my relationships, whose mentorship would I have to earn and deserve, and what do I want my day-to-day life to look like?

These questions are much more important than the mere end-goals. If we focus on the process first, the results will come later.

This is an immensely valuable mindset for me, particularly since I’m stepping into so many leadership roles in my personal and professional life in this next season. I’m going to need to be a more disciplined version of myself. I’ll need to be honest and authentic. I’ll need to put my voice out there into the world to attract the kind of relationships I’ll need to get to the next level.

I’ll have to be courageous and ambitious in my degree of self-care. Unstructured play, leisure, and plain old joy are things I’ve deprived myself of my whole life. They weren’t encouraged by my father growing up. Instead, I learned that focusing on growth and constant progress is the way to go. But it’s not. It only leads to burnout and a nagging duty to always be progressing even when I genuinely don’t want to. Moving forward, I’ll learn to be more compassionate and loving towards myself – both the good and bad parts of my personality. They all need healing and growth.

I want to be an encouraging, wise, authentic leader to others.

I want to be a gracious, loving, and disciplined leader to myself.

Beware “Open Loops” and the stories you make to close them.

An “Open Loop” is an incomplete thought or experience that’s stuck in your mind. If a friend doesn’t show up to a lunch and doesn’t call you, it creates an open loop. If a girl in school smiles at you once in the hallway, but never makes eye contact in class, it creates an open loop.

People make up stories to close open loops. The stories usually focus on the worst-case scenario.

You make up that your friend doesn’t really care about you. In reality, an emergency came up and he forgot to call you.

You make up that the girl thinks you’re ugly, or is toying with your emotions for some unknowable purpose. In reality, she might think you’re cute and be too nervous to look at you in class or just wants to focus on her studies.

Here’s an example from my own life: I have a client for whom I consult with in IT procurement. They were recently acquired, and were supposed to set up a company email for me. Despite the President of the company assuring me I’m going to continue doing work for them under the parent company, I was afraid. They hadn’t set up my new company email after waiting over a week. I made up a story that I was being replaced. In reality, their team is doing what they can given the new giant corporate structure they have to move through, and I’ll continue my work with them shortly.

When you feel panic about an open loop that surfaces in your life, check the validity of your story. Does it even make logical sense? Can it be explained without malicious intent on the part of another party? Do the stories you make up have patterns that sap your energy? Can you let them go and invite curiosity and resourcefulness into your heart to solve the problem?

Contempt destroys everything good in life.

This was a hard-hitting, personal moment for me in the training. Jean-Marie Jobs, who founded GAP, stared me down and conveyed to me with sincere emotion and passion just how important this lesson is.

Up until now, I held the average person in contempt. I judged them as lazy, irrational, stupid, asleep, and worthless. That all sounds insanely harsh, but at the core of my unconscious hurt, that’s what I learned to believe to protect myself at an early age. “Most people aren’t worth knowing” is a thought I had and clung onto for dear life in third grade as a means to invalidate the rejection I experienced from bullies.

I held my father in contempt for abusing my psychologically and verbally for years. My heart was chalk-full of it even though I had forgiven him several times for many things. Jean advised where there’s significant trauma, “forgiveness is more of a lifestyle than a 1-off thing”. That’s exactly what I needed to hear. Since then, I’ve incorporated forgiveness into my morning prayer.

Contempt is so viciously powerful at destroying good because it operates like a spiritual black hole from which no love or light can escape. If you hold contempt in any chamber of your heart, you leave no room for love, grace, peace, gratitude, or joy. You can experience these things in other areas of your heart yet to be contaminated, but the positive emotional magnitude will be diminished by the contradictory feelings residing in the darker chambers of your heart.

Biblical Wisdom? My 3 Favorite Quotes From the Weekend

This is super weird and ironic for me. I’ve never read the bible, and I’m not Christian. I ended my last relationship in part due to difference in religious values (she was Christian, I was agnostic). And here I am quoting bible verses 4 months later. Anyhow, I’m still not Christian and don’t plan to be. But this experience made me appreciate how profound some of the 2,019 year old text can really be.

Transformational Leadership is faith-based. Jean-Marie Jobs does do secular trainings for corporate clients, but I actually appreciated the verses she chose to include in the training below.

Galatians 6:4-5, The Holy Bible

Make a careful exploration of who you are and the work you have been given, and then sink yourself into that. Don’t be impressed with yourself. Don’t compare yourself with others. Each of you must take responsibility for doing the creative best you can with your own life.

This is perfect life advice. It’s a perfectly complete quote, worthy of framing without explanation. What I love about it is that it promotes self-awareness, humility, and responsibility in one paragraph. Evaluate yourself, what you want to stand for, and bring the highest expression of that into being. Don’t compare yourself to others or boast! You’re responsible only for your own creative best.

Peter Koestenbaum, Philosopher

Some people are permanently angry or in a constant state of feeling sorry for themselves. The explanation? It’s a common way to avoid the anxiety of freedom, the fear of responsibility, the resistance against owning one’s choices. The result? It keeps them infantilized forever, and none of the rewards of mature leadership will be available to them.

I know people who live this way. They are adult infants. Growth and progress are strangers to them. They only know how to frame their problems in terms of their own victimhood. Responsibility is an impossible foe to conquer for them, because they decry it at every turn.

The anxiety of freedom, however, strikes me personally. I am not constantly angry, and I viscerally hate the victim mentality. I refuse to adopt it. But freedom and responsibility invoke fear. Partially because it calls to my higher being which I know is 110% capable of surmounting any challenge – that higher being contrasts with how I show up in life today, imperfect but growing – and that contrast causes immediate negative self-judgement. By learning to be more gracious and loving to myself, I will become more free to step into that Higher Self which today causes anxiety to see.

Jean-Marie Jobs, Founder of GAP Community

Leaders are generous listeners. They are aware of their own “Internal Conversation”, and diligently seek to align it with God’s conversation about themselves, others, and circumstances. Listening both externally and internally provides a platform to encourage, edify, and build up others as well as to receive learning and correction from others.

Jean said she feels people “should” or “shouldn’t” behave a certain way:

I am more present with who I think SHOULD be there than who is ACTUALLY there.

That struck the whole room as profound. We are all guilty of this. We become pre-occupied with how the person in front of us doesn’t measure up to our ideal standard, and that becomes more important than connecting with them in the moment. We are blinded to who is truly in front of us. We are obsessed with the non-existent abstraction of who they should be instead.

Instead of measuring people against ideal standards and judging them silently, we must choose to be present with them. If we come from a place of judgement and contempt, we won’t find solutions. We’ll only reinforce our negative image of who they are, and find reasons why they’ll never measure up. If we approach people with compassion and curiosity instead of conclusions, we can authentically lead them into being better versions of themselves.

Power vs. Affirmation

Do you like power more than affirmation? Apparently I do. In a fascinating exercise, I learned that a mostly unconscious belief I hold is: “I’d rather be respected than liked by people”. This leads me to positions of power and respect. It comes at the expense of people liking me. Every belief has a price.

I actively deflect affirmations from most people, because they make me uncomfortable. Due to flaws in my self-image, praise doesn’t feel accurate. I also love affirmation from people whom I deeply respect. That’s like seeking validation from authority figure. This paradox comes from a general disdain I have towards “average people” – something that I’m realizing doesn’t really serve me very well. I put up a barrier around myself to weed people out, and let only the “best” inside.

Ultimately, someone who’s all-powerful but not loved is going to be a lonely S.O.B.

“It’s lonely at the top”, say many successful entrepreneurs.

From now on, I want to be encouraging and loving as a leader. I want to bring out the best in others, and shine the spotlight on their achievements. This will help build friendships and allies in my career. I will help others, and they in turn will help me. It’s a long-term win-win approach that leads to both affirmation and power. One need not come at the expense of the other. Both are good to have for different reasons.


TL gave me a much-needed wake up call to question my unconscious beliefs limiting my potential as a leader. I now see that there’s tremendous power in letting go of my regrets, and focusing on creating an empowering vision for my future.

TL is a worthwhile investment for anyone ready to take a leap of faith into transforming how they lead themselves and others. I’d highly recommend it!