Entrepreneurs Need to Lead and Be Led

“You talk as if you only like the sound of your own voice. Is it deliberate?”

I was stunned silent at the other end of the line.

My first six months as a manager and I was on a rapidly sinking ship, a non-profit voyage of the damned, with staff who loved everyone else and couldn’t find nary a redemptive glimmer in me.

I was locked in a cycle.

Read a new book. Go to a new training. Schedule another staff meeting.


I was doing everything I could. I was generous and giving.  Besides, they would grow to eventually like me. Because I, the girl with the books, could always could find a new strategy and a better way. But I couldn’t and they didn’t. Six months in and, for some reason, we were still missing each other.

Until I was told by someone much smarter than I was, that the reason I was searching for? It was me.

Six months and I had never asked the staff a question. I was just barking orders. Moving them like pieces on a chess board. “Go here!”, “Don’t do that!”, “It would be better if…” Not once did I ask them how to proceed.  Find out their motivation and create, with their expectations and strengths, a shared vision made real by the ongoing and mutual reshaping of each of us.

That staff on the other end of the line was the first person I ever asked about my leadership. This person gave it to me straight and taught me to reshape my management by going beyond myself. By asking difficult questions. Interrogating the process.

The ideological debate between managers versus entrepreneurs aside, both fall for overwhelmingly similar pressures and pitfalls.

How many of us are constantly riffling through seminars and strategies? Making our training and development about what “we” think we need to learn differently? Picking up the shiniest leadership tool in the box when we could just as soon talk to a person to find out if we are meeting people’s needs let alone our enterprise’s overall goals?

As belated and blessed teacher Rabbi Edwin Friedman alludes to in his seminal work, A Failure of Nerve, the details aren’t in the data. They are in the life of a unique emotional process that exists in every institution and community. As leaders, our task is to understand this process, which includes how people and systems interact and react. But ultimately, according to Friedman, our task is to master ourselves. 

That’s right: We can’t control our environments or even our staff people, but we can master ourselves.

At the start of my life as a manager, I’m struck that not only did I not know who my staff were but that I also did not know who I was.

I wanted to be liked but I barely knew which gifts I could offer up to the world, let alone my staff, gifts that were specially and sacredly mine to share.

In 2016,  I began my second-career and vocational journey as a Student Rabbi.  It is a journey of communal listening and learning, supporting individuals’ unique spiritual journeys toward the Jewish lives they imagine leading. And, as I support people’s becomings, as I watch them choose their own lives, I feel closer to my purpose than I ever thought possible.

The strong leaders I have learned from reflect this complexity: We have a duty to investigate and enhance our selves and we must move necessarily and deeply beyond them in order to foster lasting leadership.


Are You Gritty?

Do you have perseverance? If someone tells you “You can’t do that,” how do you respond? Do you get puffed up enough to make them eat their words? Or do you go back to bed and lay down for a week? How do you deal with adversity when it comes to pursuing your goals? Are you Gritty?

Life is hard for everyone. We all own our various aches and pains, yet entrepreneurship takes an extra bit of pluck that many of us often need to grow into, unless we were born with a natural go-getter spirit. There will be times when one wants to throw in the towel, bash the notebook computer with a sledgehammer, disconnect the phone and go live in a cave. That’s when it’s time to rejuice, recharge, and refuel and start over again the next day. How do you keep your enthusiasm going when it seems you’ve set an impossible goal? I hope my story will give you some inspiration.

I started my third venture, Piknik, about a year and a half ago, when I was homeless. I was living in my friends’ living room with two small children, with my older son coming for the weekends. We literally had about 3 square meters of personal space to ourselves, plus a loft bed.  I had just managed to force a poser investor out into the light. If you’re an entrepreneur, you probably know what that is – it’s the guy who strings you along for months asking for more and more work, but he never actually writes the contract or the check.  I had to scrap what I was doing and start over again. Then I became paralyzed with fear. Then I decided to do it anyway.

I launched Piknik as a very simple app for checking into and posting food photos in restaurant profiles. Right now we are only on Android, as Piknik AD. As I persevered, I picked up some team members along the way.  Now we’re on our way to making Piknik 2.0, which is set to change the online review world.

One of my sources of inspiration, my 7-year old

One of my sources of inspiration, my 7-year old

There were many times during my 7-month long stint as a homeless person when I could have decided to lay down and die and give in. However, my kids deserve better, so I kept going.

Whatever it is you are doing, you need to find that one reason to keep hustling, and keep it close to you in thought and deed, and work away at it. The stories of determined actors and business people are published weekly in our media, because everyone needs inspiration. The best sources I’ve found are Inc. online magazine, Matthew Hussey’s YouTube vlogs on business and relationships, and Evan Carmichael’s YouTube Channel, and there are many, many more.

Want to know more about Grit? You can watch Angela Duckworth’s Ted Talk here. To assess yourself on the Grit Scale, you can download Angela Duckworth’s evaluation here.

What or who inspires you and keeps you going when everything else sucks, literally? What makes you gritty? Please comment below and tell us about it!