Your lowest point of abyss, the best valuable lessons

This single mother of three knows a thing or two about smart people. And what holds them back from greatness. Her name is Lolly Daskal.

How does she learn what she knows?

She did what Dale Carnegie did during this lifetime. On the surface, he met a lot of people during his lifetime through his workshops. He made a lifetime of difference to people like Warren Buffet and left a lasting legacy — How to Win Friends and Influence People.

Beneath the surface, the vignettes of day to day people stories he shared in his book reveal his greatest gift — he intently listened to his audience challenges. And then he collated them into buckets of experience, synthesized the essence. And then he bubbled up the best stories to share in memorable ways.

That multilayer combination is rare in this world. I found those layers when Lolly spoke on finding our greatness within. That intrigued me.

Today, she is revered as one of the leading executive coaches. Dorie Clark aptly calls her the civilian with million followers on Twitter. Her workshops filled with ‘fully-present’, intent listening style started three decades ago.

That start interested me. We spoke on the phone. She recalled those beginnings.

Excerpts from our conversation, in her words.

“The day of my divorce, I was frightened. There is a saying — she became undone. That was me. Life looked uncertain. Candidly, I was not my best. My three children were young. It took me a while to get into a better groove.

Took a while to get small wins.

Small wins like the first time at the family dinner table without their father, first time food shopping for four instead of five, first time leading the charge on things like travel plans. I learned if you do it once, you feel the fear. It is ok. You can do it the second time.

The buildup of confidence gave the competitive rebel in me a boost. I doubled down as an entrepreneur. I prodded as personal development coach. Somewhere along the way, egged by one of my seminar participants, I became a leadership coach and business consultant.

I realized I needed to get myself educated. Every day I read, I still do. I found mentors in those books. I enrolled in classes, workshops, seminars, and got certified to be credible.

School of hard knocks eased the bumps along the way. My biggest strengths of open questions and intentional listening paved the foundation.

As a leadership coach, it didn’t matter what country I was in, what language people spoke, what gender that they were, I started to recognize patterns within people, most of the time, it was patterns on what held them back.”

She was on a flow. I paused her and I sent a zinger her way — “talk to me about your own Rosa Park moment.”

[while listening to her earlier online conversations with others, her voice perked up when she shared this about Rosa Parks — a gentle warrior, who created a ripple effect by refusing to give up her bus seat during the civil rights movement. ]

The quick witted Lolly paused. She finally said,

“when I am only woman in a board room full of men. It is a rebellious moment.

When I am the only woman in a room full of lawyers for a business acquisition. It is a rebellious moment.

When I am the only woman in a leadership panel, it is a rebellious moment.”

I loved her answer! I knew she was game for introspective questions. I started my volley.

Karthik — “One quote/ your research caught my left brain- 99+% high achievers suffer from imposter syndrome. You mention it as the flip side of confidence that holds them back. How did you become aware of this pattern in your own life?”

Lolly — “My clients — most of them are known for their confidence, their smarts, their business acumen. When I coached them, many expressed a polarity of character– they had moments when they felt like a fraud. They felt they were not worthy of their success.”

She continued, “I could personally relate to what they were saying, Self doubt plagued me too. I created a ritual, a discipline to leverage the self -doubt within myself.

Every night without fail, I ask myself, what did I do well today, how did I make a difference, where did I leave an impact.

Second part of the ritual, is just as important, because self doubt, comes when we are busy comparing ourselves to others. So the question I ask myself every night is, what did I do today that I can do better tomorrow and what did I do yesterday that I did better today?

The idea is to stop comparing yourself to others, but to be competitive with myself, to measure my success inwardly instead of worrying outwardly what is happening with others.

This simple ritual has a profound effect on the self doubts I have, because they are laced with positive thoughts and they combat the negative, self doubts I may have about myself. “

Karthik [thinking]. Her ritual is simple, subtle, deep and brilliant — use your own earlier version of self as the benchmark, not others. I probed her deeper with my favorite words from Robin Sharma

Karthik — If your tombstone could only have one line on it, what would that line say?

Her answer- “She served with love.”

And as we wrapped the conversation, her last words echo in my ears- hope my children read this.

In her moment of reckoning, in answering the deepest question — she revealed her source of strength. Her three millennial children propelled her then and continue to boost her now. I hope they read it too. Just like you.

Thank you for the read.

Karthik Rajan.

P.S. Candid disclosure — My introduction to Lolly was a blog she published many moons ago: Why Entrepreneurs Can Stop Taking So Many Showers. Lately, I have been listening to her podcast interviews — I was intrigued by her layers of thought, her custom preparation for each conversation and her earnestness to be useful. I reached out to her on the pretext of her upcoming book. Once on the phone, we hit it off. Our conversation hardly touched her book. Life is about chances, she was game too.

In fairness, here is the link to her book — Leadership Gap. She talks about more patterns for 7 different archetypes that hold people back from greatness. Who’s who have endorsed it.

You are welcome to sign up for my “connect the dots” short story-letter at this link.

Link to my blogs here.

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