Jessica Dalka, Owner, Chicago Planner Magazine
Jessica Dalka is a graduate of Loyola University Chicago, where she also participated in their study abroad program at Loyola's campus in Rome. She received her degree in advertising, public relations and interned in media buying and planning for Havas Media (previously Media Planning Group) before opening with a high-end restaurant in Chicago.
From there, she worked for restaurants and at a hotel, during which time she started Chicago Planner Magazine as a tool to help her learn more about the events industry.
By October 2016, she made Chicago Planner Magazine her primary focus, where she was writing, designing the digital magazine, creating social media, and email marketing campaigns, designing ads for clients and managing business development.
Jessica still works with local event companies, assisting with day-of-event management - a "side hustle" she loves because it keeps her knowledgable about the working status quo of the events world. In addition, Jessica has been an ambassador for Choose Chicago since 2015 and is a member of the Publicity Club of Chicago.
What is your favourite social media platform, and why?
From a business perspective, I love LinkedIn. However, I think it's an undervalued platform because it gives you access to so many people who you may not normally meet at a networking event, making it possible to intentionally build your network.
Tell us about you and your current role or area of interest.
I am the owner of Chicago Planner Magazine, a digital media business for events and hospitality professionals.
What do you like about your career or area of focus?
I love connecting with people and sharing stories and perspectives that don't always get heard.
What is the best advice you have ever received?
Once I was struggling with my boss early on in my career. I wanted to get a new job at a higher level, thinking I could easily do better than that person. A manager of a major Chicago hotel said to me: "If you can't handle where you are now, what makes you think it gets any easier the higher you go?"
That always stuck with me because it made me realize that no matter the problem, you have to be able to work your way through it; you can't skip steps and be successful. It's been especially important as an entrepreneur because I now know that it is essential to ensure that you are doing things properly, whatever it is, before adding layers or over-complicating the situation.
In the nearly ten years since receiving that advice, I have seen how an idea for something may not be interpreted by the consumer the way you think, or your plan that was perfect on paper may not play out in real life the way you expected. If you put it all on paper and execute it all right away, and things are wrong early on, it's a lot of backtracking. Instead, get through one step, make sure things are going well, and then you can move up, grow or expand.
What inspires you, motivates you, or helps you to move forward?
Empowering and supporting others is one of the things I love most. When people feel good about themselves, they do better at their work and are willing to help others and be positive community members. I think that's so exciting to see. It's something I try to cultivate with those I work with, whether as part of Chicago Planner Magazine itself, with clients or even someone I meet at a networking event.
What are you proud of in your life so far?
My willingness to divert from the straight and narrow path. Entrepreneurship has been a challenging road, and I know people close to me didn't always get why I wouldn't "just get a regular job," but what I have learned and what I am capable of has expanded so much. I wouldn't trade that experience for anything.
What is your preferred way to meet new people/network?
Pre-pandemic I really enjoyed individual, face-to-face interactions, but I have also used LinkedIn for many many years. I think it's a great platform for meeting other professionals and making introductions.
What skills or qualities do you feel have helped you?
Talking to people! If you can really have a good conversation with someone and understand where they are coming from and what they want and can accurately communicate how you fit within that, it saves at least 90% of your problems. Before you can under promise and over deliver, hire the right candidate, or function successfully in business, you need to make sure you're clear about the expectations.
What do you wish you had known when you started out?
It's ok to prioritize money and integrate it with your mission. At the beginning of my entrepreneurial journey, I always wanted to help people, and I still do, but at a certain point, you have to balance that with not allowing people to take advantage of you. Be clear about what you will and won't do - don't say "I can do anything!" just to book a client.
You have to value your own time because people will take as much of it as you will give them. Don't schedule an hour meeting when a direct, 15-minute conversation will do. Make sure you know why someone wants a meeting with you before your book space for them on your calendar. Prioritize your needs and make sure that you are always operating to allow you to do your best work.
Who do you most admire in business, academic or creative circles and why?
People who are different from me, who I can learn from. I think different perspectives are important for growth, not only from diverse individuals but also from diverse industries. As an event professional, I want to know the latest news in tech and finance and pharma and politics because all of those things can inevitably impact my industry and give me ideas on how to be creative and integrate the latest and greatest that's out there.
Outside of your professional/work area, what hobbies or interests do you have or what other areas of your life are of real importance to you?
I find that the hobbies I enjoy intersect with the work I love doing. I love creative activities like songwriting and drawing, and a lot of the work I do involves writing and graphic design. Brainstorming business ideas and strategizing is actually really fun to me, but of course, I also love a good Netflix binge or hanging out by the lake in good weather.
Has the pandemic had a positive or a negative effect on you and/or your business, and how have you managed it?
At first, I would say it was catastrophic. Still, like many people, I think that aside from the obvious and unfortunate tragedies ranging from lost jobs and businesses to lost loved ones, the pandemic has forced us to stop and prioritize what matters to us as people. I think this has been a really big moment for events and hospitality, which I would argue is one of the most under-appreciated and misunderstood fields of work.
When no one could go out to eat, go to concerts and music festivals, host large weddings, or go to their conferences, we everyone realized that events are actually the fabric of our society. So, I'm using that perspective to re-evaluate what Chicago Planner Magazine provides, how we are connecting different people in our own field of work, and how we as an industry need to be treating ourselves.
Do you have a mentor, or have you ever mentored anyone?
I've never had a formal mentor, but I have had some great individuals who I have learned from, and who have influenced me and guided me. In turn, I also try to encourage young professionals, especially women, to push for what they want and work towards being their best version of themselves.
What advice would you have for someone looking to get into the same area of work or interests?
Do your research and try to shadow some people or interns first. I have created work for myself that fluctuates between actual event work, writing and media. I do everything from graphic design, to working with public relations partners on stories, to creating content and executing events for a few hundred people. Sky's the limit, but be prepared to work not just hard but outside the standard 9-5 hours.
What do you feel is the most common reason people fail or give up?
Misunderstanding themselves. If you don't know who you are and what you want, you can't possibly work towards your goals. As I have gotten older, I appreciated that I gave myself space in my 20s to learn and grow professionally, push myself personally, and figure out who I was.
Climbing the ladder doesn't get easier, so when you go up against bigger fish, you have to be confident in who you are and what you know.
Is there a phrase, quote or a saying that you really like?
"If I don't know, I'll find out."
I won't lie and say I know something when I don't, but instead, make it my mission to show I'm willing to do the work to provide a solution. I think that's been a key part of building a positive reputation as a professional. Your honesty is just as important as your abilities.
What companies, brands, or institutions do you like or do you think are getting it right?
I'm a social media marketing girl, so I'm obsessed with TikTok right now - I think they have just brought a whole new approach to social that's direct but not just an offshoot of Facebook.
I am huge on Canva. That company is why I have my business. I found them about five or six years ago when they were these little guys out of Australia. Their software was so intuitive, and they have done a great job of continually updating it. I've learned a lot about graphic design through using it. I love that they have evolved into a great resource for people in social media, marketing and public relations, who don't need to be full-scale designers but need good, clean imagery quickly.
How do you define success, and what lessons have you learned so far that you could share with our audience/readership?
I'm trying more and more to swap "success" with "accomplishments" or "happiness" because most of the time, success is just another word for a lot of money. But the most impactful people aren't just the ones with big bank accounts. In a perfect world, I think success would equate more with the qualities of the people who mean the most to us.
I feel the most successful when I have a good chat with a fellow business owner who was struggling and now sees a way through their problem. I feel the most successful when someone has seen my previous work and wants to connect or collaborate.
If you substitute success with happiness, you actually have the pieces to a fulfilled life, which I believe isn't appreciated enough in the business world. Inevitably, we all want to positively contribute to the world around us, and you don't need to be rich or famous to do that.