Playground Chatter with Bobby Umar, Leadership Speaker

Welcome to Playground Chatter! Our blog series, where we get to profile and chat with some of the best executives in town! Sure, we could ask about all their fancy business stuff but since we are fun monsters, we want to know how they spend their spare time on the playground of life!


Your Name: Bobby Umar

Your nickname? Fun Bobby

What is your grown up job? Leadership Speaker

How can we find you?


          Instagram: @raehanbobby/

       Pinterest: /raehanbobby

     Twitter: @raehanbobby


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Tell us where you spent your childhood years. Is there one year you remember most?  I grew up on the east coast of Canada, in New Brunswick. I had a pretty awesome childhood and most of the years were great. We spent our entire days outside, playing street hockey, exploring the forest, biking through sand dunes. I also remember starting our camping years with my family. But I really loved the first few years of school, especially grade 3, when we had an exchange teacher from England, Miss Scott who really was amazing. I was also at the peak of my academic skills and athletic skills. Aside from doing well is school, I remember being a strong long distance runner and the dodgeball champ. But soon, my athletic skills would go down big time. Finally in grade 5, I was honoured to skip a grade, which as pretty cool.

Favorite part of the playground to hang out in? I was either playing hockey or baseball on one side, or on the other side with the girls playing jump rope. Even back then, I was mixing up and not caring about any stereotypical gender roles.

Lunch pail, brown bag or did you buy lunch? I was the guy who had his mom make soup and toast once a week in my lunch pail. That was a treat, as was my mom’s famous curried ground beef sandwiches. But my staple lunch, and I can’t believe I’m sharing this with you, was actually ketchup and lettuce sandwiches.


What would be your ideal recess today? Hmm…ideal recess would be hanging with the girls talking about boys, then playing different team sports. I would have a nice bagel for a snack.


If I deemed you Playground Monitor for the next 15 minutes, how would you rally your employees? What activity would everyone participate in? I get us all to play a combination of my favourite teambuilding games, including Big Booty, Zip-Zap-Bop and Take and Stand. Big Booty and Zip-Zap-Bop are improve games. Take a Stand is where we take an issue or situation and get people to choose one side over the other and then say why they chose that side.


What rules did you learn on the playground that you still utilize today? I moved around from location to location. Learning about the diversity of the playground is also how I live my life with connecting. I believe the diversity of my network leads to diversity of thought, experiences and action.  I did learn that kids can be cruel sometimes to one another and teaching my own children to believe in themselves and stand up for themselves will be key. I also learned about playing fair and playing inclusively. Finally I learned that men and women can play anything they want, regardless of what people tell you what you should and should not do.

When does time disappear for you? Vacation time is a good one. Play time is another big one. When I was a kid, playing hockey, snow sledding or going rock climbing, I never noticed how late it got until the sun started setting. Nowadays, only on vacation do I feel time disappear. It is a hard feeling to capture again.


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What is your authentic intention (that thing that you really, really want to do or accomplish?) What are you doing to get there? My big intention is to help one million hearts find their authentic path of passion and purpose. I seek to inspire and teach these ‘lost leaders’ as a world-class speaker, author and coach. I want to tell them that it’s okay to feel lost personally, professionally and academically because I have too. But it’s not okay to do little about it.

I am getting there more now by having my first speaker agent, coming out with my first books on ‘How to Network Anytime’, and I just created a 12-week modular coaching program called Networking Mastery.

In her book Permission: Stop Competing & Start Creating the Life You Want to Live, Nicole Matthews, Founder of The Henley Company, talks about giving yourself permission to design your best life. Which area of your life needs a little more attention? What are you willing to give yourself permission to do? The biggest area is my health. I recently started a movement called #FitInMyLife because initially I wanted to get fit in my life, after a lifetime of just ignoring it or letting things get worse. I now realize that this movement and hashtag is two-fold because, I am also trying to make everything fit in my life – my kids, my wife, my business, my health, my friends and everything else I want to do in this world. I am willing to give myself permission to spend some time during the weekdays to do healthy things and focus my attention on my young children whenever they are home. Then I am Super Daddy. But it takes some toll on my ability to spend on my business. This is one of the reasons why I am looking now at ways to scale and automate revenue systems.


Define happiness in less than 140 characters. The feeling, creation or manifestation of authentic joy, fulfillment, purpose and peace, whether for yourself, others or the world.


Grab your colored chalk and write a motto on the asphalt of the playground for all the kids to see. What’s your message? Fight for your life: the one you truly want to live, with success defined by you and supported by those who love you.


What will you do from this day forward to design your life to better incorporate more recess? (Pinky Swear). I will try to incorporate more recess where time can disappear and gratitude can create monuments of every moment.

I will look at my life more holistically and find the balance between planning for my purpose, impact and legacy while also exploring all the joy and happiness that this world has to offer.

I will continue my path of love, gratitude and leadership to serve every lost leader in my story and role as a father, brother, son, partner, friend and business person.

Thanks Bobby! You are awesome!!