A Pivot of Passion

One of the lessons learned from Covid is not to take anything for granted, from our relationships with friends and family to the affection of a spouse to the opportunities and passions in our lives.

Life’s short, happiness matters, and it’s ok to change your mind along the way.

For one of Winnipeg’s top event planners, Jessica Kraut, Covid was a chance to imagine another path, explore a new passion, and make some significant changes in her life.

Swapping out one headset for another, she closed her event company to focus on becoming a flight instructor.

Being someone who admittedly fears change more than snakes, I watched in awe over the past year as her huge life-changing transition unfolded on her IG, and I admit I was intrigued. I wanted to know more about how this happens? What’s the mindset? And what it took to make such a dramatic and bold move. So, since I have a magazine, I thought, what a great opportunity to learn more about her inspiring story and what a great message of determination this is for our readers, just like me who need a good KITB (kick in the butt) once in a while to push us out of our comfort zones. Here’s how it went.

SW: Why did you become an event planner?

JK: I have always loved problem-solving, working on puzzles, and being very overly organized; it comes naturally! I suffered from anxiety and constant worrying when I was a teenager and I decided to take that energy and put it towards Event Planning. As an event planner, imagining and preparing for the worst-case scenarios was an asset, and it was an excellent place for me to channel that energy positively.

SW: Your company was wildly successful right from the start; what are the top three things you did to set yourself up for success?

JK: I spent a lot of time learning who my customer was; what they expect from me, and what makes an event successful in THEIR eyes. I surrounded myself with other event professionals who provided top-quality products and services. Building those relationships helped me deliver the best events possible and created a reputation for my company among vendors who would then refer us to their clients. Word of mouth is a powerful thing, particularly in a smaller city.

“We can’t successfully be all things to all people. Learn your customer, learn your niche and be excellent at it.” 

SW: We learn through failure; what was your biggest mistake, and what did you learn from it?

JK: I would say that in the beginning, I tried to be a one-stop shop and provide every kind of event possible rather than stick to what I was passionate about and what I was good at. We can’t successfully be all things to all people. Learn your customer, learn your niche and be excellent at it. For me, focusing on Corporate events and particularly Fundraising. events in the not-for-profit world were something that I was passionate about and that I felt I had the best skills for.

SW: What moment are you most proud of in your business?

JK: The day I was trusted to plan my nephew’s wedding was the most special day of my career. Knowing that my family had seen my work and trusted me with such an important event with their whole hearts made me feel that l had achieved success.

SW: Now that you are not in events if you could change one thing about the event industry, what would it be?

JK: I think many people are still figuring out what an event planner is and how their skills can best be used. It would be wonderful to educate people better on this so that when they hire a planner; their expectations match the services that can be delivered and so that they don’t miss out on the advantages of hiring a planner.

SW: What is the biggest lesson you took away from your career as an event professional? 

JK: When you provide a service, no matter how good a product may be, the most significant impact will come from the people involved. Excellent customer service and reliable staff is the most critical factor of all.

SW: Was it a hard decision to move on to a different career?

JK: Moving on from event planning was undoubtedly hard as I had done something for ten years and truly loved it. I had built up an excellent list of repeat clients and created strong relationships with Winnipeg venues and vendors. Covid-19 and all of the restrictions that came along with it forced me to look for other opportunities because I knew that it would be a long time before I would have a chance to plan events to the scale I needed to be successful. I thought about my future and where I wanted to be 10-20 years down the road. I knew that I had fallen in love with flying and the aviation community. I saw an opportunity to become an instructor and build a life where I am constantly learning, challenging myself and others, and surrounding myself with energetic young students who shared my passion. I also saw the chance to make a difference in the aviation community as one of the few female instructors in the Province.

SW: What is your life like now, and how has it changed? 

JK: I feel fortunate to have so many things in life that fuel me. Fitness has always been an essential part of my life, but l decided to work even harder and begin training for a fitness competition with more time on my hands. I spend time working towards that goal every day, and even though competition dates are constantly changing, I see this is a way of life for me, and l know one day soon, I will be able to compete. Regarding my flying career, I am driven by the challenge of learning new things at 32 years old and going back to school. I love being thrown into situations that scare me just a little and learning to trust my skill and instinct to overcome them.

SW: What do you say to yourself to get through tough days or periods of doubt?

JK: Win or lose, my family and my dogs will still be there, happy to see me:)

SW: What advice do you have for anyone looking to make a life change but who may be fearful of leaping?

JK: You never know unless you try. I went for my first flight lesson as a way to conquer my fear of flying. After a few gut-wrenching experiences on Commercial flights, I had developed a terrible fear of flying. It held me back from the travel I wanted, so my husband suggested I take a flight lesson to understand how it all works and feel safer. I never looked back. 

SW: What’s next?

JK: I hope to continue working on my fitness journey towards competing and an overall healthier lifestyle. As for flying-the sky is the limit!

SW: Any regrets? Would you change anything?

JK: Not a thing

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