Questioning … Myself

Jon Wengrow Dwoskin
5 min readMay 30, 2021

You may want to ask yourself some of these questions, and your own answers may surprise you!

Q: What do you wish you could have told yourself at age 20? Age 30?

Jon Dwoskin: I would have counseled my 20-year-old self to have more balance in my life. When you are young, you want to do so much and prove yourself. I put a lot on hold when it came to just “hanging out” and taking some downtime. I worked to burn out and didn’t do enough fun stuff. So, I would tell my younger self to have more balance and everything will work out as it is supposed to, and that you need that time to refuel so you can be sharper and work smarter, not just harder.

At age 30, I’d tell myself the same thing. LOL.

Q: You had a very successful career. When did you realize it was time to leave the corporate world and go into business for yourself?

JD: The corporate world was never really for me. I knew how to play the game and played it well, but in the corporate world, you have to bite your tongue a lot and conform. It’s hard for me to do that. I have too many ideas and am too creative. I found myself losing my identity and becoming a robot in the corporate world. I knew I had two choices: stay and conform, or leave and start a business being myself and doing what I loved. I chose the latter!

Q: Your mantra is “Think Big.” Is bigger always better?

JD: Yes and no … “big” is up for interpretation. I define thinking big as doing small things every day that compound over time into something big. No matter how big you want to grow, it is important that you are never complacent and bored. If you are, that usually means you are in the wrong field or job.

Q: Can you teach someone to be an entrepreneur, or is it innate?

JD: I think it depends on how you were raised and a combination of a burning desire you have inside you to do something and bring an idea to life. I was raised by an entrepreneurial father so it was all I knew. That being said, I also have the DNA of an entrepreneur, but it certainly helped that my dad nurtured that in me. Even if you don’t have that background, if you have the DNA and a desire that is so deep you can’t explain where it comes from, and are willing to surround yourself with the proper partners to bring that idea alive, then you can do anything. You have to be willing to take risks and that is what being an entrepreneur is all about — a deeper level of risk tolerance.

Q: You talk a lot about communicating effectively. What is “resting face” and why is it so important?

JD: You can be saying one thing while your body language says another. If your face looks pissed off, your brand is being diluted and you decrease your ability to influence your team and your clients.

Q: Why is it important not to interrupt?

JD: There is so much growth in listening and hearing someone and allowing them the space to get their point across. Everyone processes a bit differently so if you interrupt their thought pattern, they can’t get back to that space and you lose the essence of what they want to talk about. Too many times they have gems that they can’t get to because they get interrupted. There is also importance in silence and in not always filling space with words, but taking time to absorb and respond. The best advice is to take notes while others are talking so don’t lose your own thought or question — and you don’t interrupt.

Q: What is the №1 thing that gets companies stuck?

JD: The owner and C-level exec(s) won’t admit that they have a problem. They CAN’T come to grips with the fact that although they are successful, they are stuck. Add to that their longing to be the best they can be and not looking back about how they could have done things better. Without this, it’s hard to get started and stay consistent in growth.

Q: What are three things companies can do to get unstuck?

1. Understand who they really are as a company and if their message/brand is consistent with that. They need to make sure they are working with their ideal client and haven’t stretched themselves too far with the wrong clients.

  1. Fire a few people who are toxic and holding the company back. This is a compassionate act because most people know they are the wrong person in the wrong seat, but don’t have the courage to quit. That being said, most C-level people don’t have the courage to fire people, which is a major problem that holds companies and people back.
  2. Reset and/or grow their culture (or get the one they need). To do this, first they must define it, then they need to grow it. This is critical. The CEO/president is responsible for 95 percent of the culture. If the culture is great, it is because of their beat of the drum. If the culture is lacking, it almost always points back to that C-level exec and the type of manager he or she is.

Q: So how do you grow and/or reset your culture?

JD: Go back to the fundamental root system of what the company is all about and begin empowering managers to empower their team. It starts with empowerment and then it’s the small things. A lot of times when people feel micromanaged and not trusted, the culture can never take off. Layer in good quality management and some fun stuff, and you are on your way.

Start asking yourself some probing questions about your business and your culture. “The important thing,” as Albert Einstein said, “is not to stop questioning. Curiosity has its own reason for existing.” Or, as I like to put it: Think Big! Very Big!

Think Big!




Jon Wengrow Dwoskin

I help successful business people get unstuck and grow their business as a business coach, speaker, podcaster and author of my book, The Think Big Movement.