When Faith Meets Hustle

Jackie Jackson is not new to Chicago News Weekly; the burgeoning entrepreneur graced the cover of the then-budding newspaper in 2022. She was scoring points then on the rise to her now 2.0 moment. Her accomplishments were already record-breaking. She owned several Kilwins locations and was opening a Fatburger franchise on the South Side of Chicago even when advised not to. She explains it this way:

When I was planning to open a Fatburger franchise in Chatham once a thriving Black community, now considered a food desert people questioned my decision. They asked me why and doubted me. Many told her it wouldn't work.

I saw something they didn't. I envisioned long lines cascading out the door, a community gathering place, and jobs for local teens who needed a first chance, just like I was given, she said, like a visionary who can see in her mind what she puts in motion to become reality. That vision fueled my hustle. I wasnt just building a business; I was serving a purpose. And that leads us to the present.

Since that 2022 1.0 moment, Ms. Jackson has been awarded Illinois Small Business person of the Year (2024) by the U.S. Small Business Administration for her excellence, innovation, and resilience in the Chicago business community. The prestigious award is part of the National Small Business Week program. She has experienced business growth: starting with just 10 employees, her ventures now employ over 75 people.

Indeed, Ms. Jackson has been busy. Since that initial interview like software versioning where 2.0 represents a major update that clears flaws and adds new features she is the new and improved version of her former self, which was fine. Today she has stepped up her game and added author to her repertoire, establishing her public persona as stronger and more capable of achieving whatever she chooses to execute.

She shared a practice that has become a way she processes all she does in pursuit of a goal. She smiles and states, matter-of-factly, Your hustle will be tested. Thats why you have to distinguish between the two your hustle and your purpose.

You have to separate the money, which is motivation, from purpose, which is something greater. It doesnt come and go; it simply is once you commit to it. In my book I talk about Purpose Over Paycheck, because it's easy to get caught up in chasing money. So it's important to understand that purpose provides sustenance. It is the process of supporting, maintaining, or providing the necessities of life, including spiritual or financial support.

With that clarity, she addresses life as we all know it: it's not a smooth sail. She points out delays, setbacks, financial challenges, and the inherited life tests that descend upon us all. But heres her point: When your purpose is clear, you don't quit. You push, you pray, you persevere.

Ms. Jackson says with conviction, it's the purpose that drives you, inspires you, and gets you up and out of bed at 5 a.m. and fuels you throughout the day until late at night when you'd rather be sleeping.

The Beginning

Jackies adolescent journey began as the youngest of seven children born into a middle-class family. Then her parents divorced, and she, along with her two sisters and her mother, began life anew. The four older siblings were successful adults living their separate lives quite comfortably.

She says she learned much from her very strong and independent mother, Jessie Pearl Moore, who refused any support from her father. Though her new life started out differently from her previous life, it helped shape and mold her into the woman she has become. Experiencing less; struggle; impacted her outlook on life.

She tells of her love for burgers as the incentive to work at McDonalds. She was excited for the opportunity because she had access to burgers at any time. There's more behind the story revealed in the book.  Although she once thought she would work at McDonalds forever, life revealed otherwise.

Ms. Jackson is very clear about the mentors or angels in her life and lists their roles: first, her mother, Jessie Pearl Moore, who provided her the foundation upon which to ground herself. Under her mothers guidance, love, scrutiny,  and her faith, Ms. Jackson learned to trust in God. Her elementary teacher, Mr. Wille Mack, saw what she did not. She was shocked when he suggested she run for class officer.

Her preconceived notions included that she was not a straight-A student, and the reasons not to enter the election went on from there. Yet with Mr. Macks encouragement she chose to enter the race and I won't reveal the outcome, but I'll emphasize this: she's never stopped since that moment.

Then there was Mr. John Bradshaw, a McDonalds franchise owner, who saw her in his restaurant, recognized her as a star, promoted her at 14, and unbeknownst to her changed her trajectory. While visiting a friend at college, she by happenstance met Mr. Danny Sledge, who opened the door to college when she had decided it wasn't for her.

It was the foresight of those three men that informed her sense of purpose and helped her begin to listen to her heart rather than allow the hustle to run her. She quotes scripture: Encourage one another and build each other up, just as you are doing (1 Thessalonians 5:11). She explains that shes learned leadership is not summarized by the size of your bank account or the number of people you employ.

Each of those deciding moments transformed vision into breakthroughs for Ms. Jackson because what they saw in her pierced the veil. There are others who have always recognized her potential especially her siblings but it lands differently when it comes from those in a position to point the way and help you pivot.

Very clear about her purpose, pursuing it has moved mountains and opened doors that otherwise would have remained shut. For Ms. Jackson, she exclaims, I'll never stop pouring. Not because its easy or always appreciated, but because I know that every time I pour into someone and watch them rise, I am reminded that I am fulfilling my purpose. Just as others have poured into me.

And with great clarity she says, I'd rather be remembered for how I loved than for what I've built because buildings can close, brands can fade, but people carry what you pour into them forever... and hopefully they contribute to others as they have been contributed to. It's more important how many people grow because of you.

This reality brought her to write the book. It offered a way to reach a greater number of people to touch, pour into, and make a difference.

She had been pouring into others long before her huge success; shes been doing it all along her journey.

Ms. Jackson talks about paying it forward and provides an example: she bought property from a developer and ended up purchasing two additional properties, each rich in equity, value, and opportunity.

Years later, recognizing the opportunity as a blessing, she paid it forward by selling the properties to her tenants. I paid the closing costs.

I gave them equity. Because thats what faith and hustle look like in real estateits not just buying buildings, its building people, she says with a smile.

She also shares an example of pouring into a promising young man who began working for her at 18 and a powerhouse young woman who began her journey with Jackson in her early 20s. Her recognition of the 18-year-olds strong leadership instinct prompted her to challenge him to help him grow; he translated that as her picking on him.

She told him, The moment I stop riding you is the moment Ive given up on your greatness. I push you because I see who you are becoming.

The young woman was quiet initially, not saying much but paying attention to everything, Jackson says. She had hustle in her DNA. In time she became one of those employees Jackson could depend on: steady, reliable, and knowledgeable. Ms. Jackson observed her growth, watched her evolve, and saw her sense of competence develop.

Consequently, she held her to a high standard and the young woman soaked up everything. Ms. Jackson notes that the two individuals described here are investments she poured into. They are more than employees; they are members of my legacy. They represent what it looks like when leadership meets love, and when faith meets hustle. She makes it clear that she is not a babysitter; she's a builder.

Long before I had faith I had vision, she says, reminiscing. The first time I intentionally manifested something was with a glue stick, scissors, and blind faith. She cut out an image of Oprah, pasted a Kilwins logo on her heart, and wrote one sentence: Oprah will find out about Kilwins and Kilwins will be a success. And as it was written, it came to be. Such is her story, the journey that influenced her desire to write her book to help others achieve their visions.

When Faith Meets Hustle, by Jackie Jackson, is in stores now. Her book tour kicks off in May, so share with your friends and encourage them to attend the book signing when shes in their town.

In closing the interview, I asked her about the title, When Faith Meets Hustle, because I thought it was interesting. The word hustle threw me for a loop. I shared that it made sense, but I found it a little perplexing once I began to read the book. Her take on hustle was not the usual way we perceive the word.

So, in the norm is to think of hustle in it verb form:

verb

1. force (someone) to move hurriedly or unceremoniously in a specified direction.

"they hustled him into the back of a horse-drawn wagon"

2.

obtain by forceful action or persuasion.

"the brothers headed to New York to try and hustle a record deal

noun

1.

busy movement and activity.

"The hustle and bustle of the big cities"

I think its safe to say that most of us assume hustle to describe someone attempting to sway you to purchase something, or to get over on you. He was trying to hustle me," or as a noun, His hustle was three card motley.  Ms. Jackson's pivot has shed a new light on the word hustle when it is referred to from a positive reference.

She explains, Hustle is more than grinding until youre exhausted; it's about moving with intentionality, knowing why you're working so hard. Purpose fuels the hustle. In closing she ended with these words,  I don't hustle for attention or money, I hustle for the purpose behind it all: my family, my community, my legacy and my faith.

The prominent Chicago entrepreneur owns and operates multiple Kilwins franchises across the city

Visit Kilwins

Hyde Park: 5226 S. Harper Ave (her flagship location opened in 2012).

Michigan Avenue: 310 S. Michigan Ave.

Chicago-Area Kilwins Locations

Jackson currently oversees several high-profile locations in the Chicago metropolitan area, including:

Navy Pier: A popular destination for tourists and locals alike.

Andersonville: 5205 N. Clark St (where she officially accepted her SBA award).

River North: Part of her continued expansion plan.

Evanston & Geneva: Extending her reach into the neighboring suburbs.