McKensie Mack is a creative, entrepreneur and communication strategist who hails from the South Side of Chicago. Her work today ranges from satirical campaigns, to language learning, to community building for women and people of color. She passionately says, “I believe it is our right to be visible. I believe it is our right and our responsibility to make sure that those around us who have been forced to be invisible be made visible again.” Her interests also lie in empowering young women as she works to foster a community of strong, diverse, badass women for future generations to come. A self-proclaimed night owl with a Southern soul and a ‘bad’ attitude, she is a force to be reckoned with.
What ignited the spark in you to start a business? How did the idea for your business come about?
I wanted to have a positive impact on my community, communities of color. The freedom to position myself to invest in communities of need by having my own business is one of the reasons I focused on becoming an entrepreneur. Plus, I like having the space to create, to change and to progress independently of anyone or anything else. So working outside the typical desk job was just right for me.
What is your favorite aspect of being an entrepreneur?
Every day I wake up, I get to be a creator. I get to make the intangible, tangible. At my core, I'm a designer of experiences. There is something magical about seeing people’s reactions to something they haven't seen before, something unexpected that is so fucking cool. With the kind of work that I do with TIM and Hey Candid, I get to develop experiences around communication and I get to see people succeed at doing things they wouldn't have envisioned themselves doing before.
"Spend time with people that make you go “damn”, people that inspire you, motivate you and reinvigorate you. People that get you. Talking to people you trust about your creative shit and offering your own assistance and support with the development of their goals. People sharpen us, they keep us on top of our game, and they give us the support we need when the work gets hard. Those kinds of relationships are best when it's cyclical because everybody wins."
What are some of the biggest challenges you’ve faced as an entrepreneur?
Dealing with racist or sexist perceptions of what people think I should be. Having to feel as if you need prove yourself first, prove your worthiness to be in a room is tiring, but is a common experience for black and brown people in the US. I remember once I was pitching to a major organization and mid-pitch, I was interrupted by a man with a question. I'm thinking he's going to ask me about something I just presented. But he doesn’t. He wants to know if I'm black. I’ve also gotten the “Oh, so you own a business by yourself?” Like, uh… yeah, I can also write my own name and I can put all my fingers up when I want to, want to see the one in the middle? At the beginning, that kind of reaction affected me to the point where I questioned my work and my direction. I had to take a step back and ask myself what was more important to me, being more accepted by others or being fulfilled by doing the work I wanted to do, not the work people expected from someone who looks like me. It was hard, for sure. But I chose the unbeaten path. Right? Two roads diverged in a wood and I, I chose the one less traveled by. And that has made all the difference. If anything, having experiences like that taught me so much about myself. I figure if people will choose not to accept me because of who I am, I might as well go even harder in the paint with all the boldness, colorful, unabashed magic I can muster... These days I am way more secure in my identity and won’t let anyone diminish my shine so they can maintain some rudimentary sense of control over their own personal foolishness.
"When you’re shaping a business or brand that is representative of you, it’s important that you give it permission to evolve into what it’s meant to be. Most people won't see what you see, but your vision at the end of the day has to be the loudest voice in a room full of loud voices."
What would you say are the top three skills needed to be a successful entrepreneur?
Resilience. Because you need that to get through the rough times. I’ve learned the most from my challenging situations because they have shown me the depth of my commitment to my work. Vision. Because it’s not only about the idea… It’s about the strategy. What steps you'll put into place to share your magic with as many people as possible. The questions you ask yourself as you build and construct your world. How is this sustainable? Where will my coin come from? How will I spend and re-invest my money in my business once it starts coming in? Even if you’re not a planner, you can still put a pen to paper and develop a list of goals that you revisit and recreate as you progress. Lastly, I’d add the ability to foster real community. Spending time with people that make you go “damn”, people that inspire you, motivate you and reinvigorate you. People that get you. Talking to people you trust about your creative shit and offering your own assistance and support with the development of their goals. People sharpen us, they keep us on top of our game, and they give us the support we need when the work gets hard. Those kinds of relationships are best when it's cyclical because everybody wins.
In one word, summarize your life as an entrepreneur.
"We need to make mistakes to be real. Without them, we lack perspective. I believe in stumbling. I believe in facing the challenge of losing and still waking up the next day, charged up, ready to make the dream work."
What have been some of your failures and what have you learned from them?
Not listening to myself enough and allowing external voices to define me or drown out my intuition. This is a never do. When you’re shaping a business or brand that is representative of you, it’s important that you give it permission to evolve into what it’s meant to be. Most people won't see what you see, but your vision at the end of the day has to be the loudest voice in a room full of loud voices. I'd also add, not allowing my projects the space to be imperfect. I used to place unreasonable expectations on myself and my work that would cause me so much stress. I'm talking Oreo cookie binge at 5 in the morning stress. I've since realized that there is beauty in slow evolution and growth. Since then, I’ve given myself permission to begin simply and to allow my ideas to grow and develop as I do.
Do you have any regrets or wish you had done something differently?
I aim to live my life without regret. I've definitely met folks who think I should be more cautious about pursuing my interests [laughs]. But we won't talk about those people [snaps fingers]. If I really want to do something, I do it. Living a life without regret means pursuing my vision how I want to, when I want to. It also means being honest about who I am as a multipotentialite.* That doesn't mean I never make mistakes. I make tons of mistake. It just means I give myself the space to pursue my curiosity. I don't give up on things because people think they won't work for me. I just glide through chapters. Once a chapter is complete, I close it and move on to the next part of the story. We need to make mistakes to be real. Without them, we lack perspective. I believe in stumbling. I believe in facing the challenge of losing and still waking up the next day, charged up, ready to make the dream work.
*For more on what it means to be a multipotentialite, watch Emilie Wapnick’s TED Talk ‘Why some of us don't have one true calling’.
"It ain’t good if it ain’t got issues… You can’t be good without complexities, issues, difficulties, etc. We become good when we try, we become great when we don't give up."
Can you name a person who has had a big impact on you as a leader? Maybe a mentor? Why and how did this person impact your life?
My mother, hands down. She is the most brilliant person in my universe. She raised four kids by herself and went to school at Northwestern while working full time. Growing up, we didn't always have everything we needed, but she never made us feel like we should be ashamed because of it. Our joy was defined by us. I think the fact that I am silly as fuck now is because of her too. Man, when I tell you our house used to be filled with so much laughter and joke telling and pranking, you'd be amazed. She's a mentor to me when it comes to my own self-acceptance. She never sat me down and told me who I should be but instead asked me who I was. When I step into a room with a huge blonde braid and my Adidas sneakers I hold my head high because I know where I come from and I take pride in that. Just last week, my mom finished her coursework for her master’s degree so she basically kills the game every single day of her life.
Another non parental mentor in my life was my fifth grade teacher Mr. Kleckner. I went to a predominantly black school on the South Side of Chicago. He was the white guy with a fire for life. He taught us things that went beyond the syllabus. Primarily, he taught us how to follow our individual curiosities. It didn’t matter what subject, he’d always take a step back and make us question or imagine the impact and beauty of that concept. He’d ask, “Can you understand why this is beautiful?” and when he asked that question his excitement, his sincerity was palpable. It’s one of the best questions anyone can ever ask you because it calls you to question your sight and examine how you’re experiencing life. He made us want to learn. He was also one of the first educators that really saw me, that recognized me. When he noticed that I liked reading, he would pick a book, place it on my desk and tell me to read it. That impacted me considerably because I used to feel invisible in school. He changed that.
What is the best piece of advice you have been given?
It ain’t good if it ain’t got issues. I heard this once on the radio and I thought, Damn. Truth. You can’t be good without complexities, issues, difficulties, etc. We become good when we try, we become great when we don't give up.
"I manage [the fear of regret] by fighting the feeling I think we all have to contend with sometimes. It’s the feeling that the space we take is too much. It’s the feeling that says we’re not good enough to pursue greatness. When I feel the urge to try something new, I push myself to do it right then before I can even think about the reasons why I shouldn't."
What does success mean to you?
Oooh, the success question. [laughs] I think of success in two ways. One is making the money and living with agency and the second is creating the thing that makes real and lasting impressions on the lives of people. I’m shooting for both.
What about happiness, what makes you happy?
Chill people that are down with the revolution. People with a great sense of humor. Silliness. Music. Hip Hop. Political satire. Performing live in front of an audience. Writing. My growing community of people I admire. Being loud. Building community. Bringing joy into the lives of people. Steak tacos. Dancing my ass off. Learning. Proving people wrong. Random conversations with others in languages they would never have thought I was fluent in. Big hair. Bright clothes. Dope shoes. Creating something out of nothing.
Since we're getting deep, what is your greatest fear and how do you manage it?
My greatest fear is regret. I don't want to wake up one day and think if only I had... or what if I had... I manage it by fighting the feeling I think we all have to contend with sometimes. It’s the feeling that the space we take is too much. It’s the feeling that tells us we’re not good enough to pursue greatness. When I feel the urge to try something new, I push myself to do it right then before I can even think about the reasons why I shouldn't. It's the reason why I now have a backlog of content, workshop ideas, songs I've never shared with anyone but will one day. The most important part is taking that creative energy and putting it to work. Mantra of the day: Cast out the fucking doubt. [laughs]
When you die, what do you want to be remembered for?
My dreams. My sense of humor. My drive. My kindness. My impact on this city I love, my Chicago...
What are your short term and long-term goals/intentions?
I want to develop my work to the point that I can have my own work space one day, where people of all types can walk in and feel just how welcomed they and their imaginations really are. I'm learning how to code this summer so I'm excited to add another dimension to things I can build. I love this city. Both in the short term and the long term, I want to do whatever I can to rewrite its future. A lot of the work I do now is about building my own resources so I have more to give to make it better.
What are you goals for the second half of 2016?
Goals, goals, goals. By the end of 2016, I want to have tripled the size of the TIM audience. I’m hoping to have the beta application designed and ready for use by the beginning of next year. I want to take the second half of 2016 to be even more visible in everything I create, whether that be in an online workshop, a song I’ve written, or a community I’ve built – I'm looking to bring even more color to the work I choose to create in the world.
Keep up with McKensie’s work here:
TIM is the communication app for awkward people. It began as an experiential institute teaching people how to communicate confidently in real-life situations. Now an early stage tech company, TIM’s mission is to make the most interesting, bizarre and memorable conversations of our lives a little more delightful.
Hey Candid! is a consultancy that empowers teens and young women to communicate effectively by telling their narratives in a powerful way. Hey Candid! serves as an avenue to provide young girls with support and encouragement during a crucial time in their lives. McKensie founded the consultancy as a way of giving back to a community of girls that are in a position of feeling self-conscious or not enough
Women Get It Done, WGID, is a collaborative community of diverse women whose sole mission is to provide resources and support to help one another fuel big ideas in their personal and professional lives. McKensie is a co-founder of the Chicago Chapter.