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Meet Melissa Jones of Little Black Desk Society in Lakeview

Today we’d like to introduce you to Melissa Jones.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I moved to Chicago in fall of 2014 after 13 years in Corporate America to start my own business. I saw a need to help women small business owners with leadership and process improvement. Moving to a new city I knew I would need support and a community where I could share and receive feedback. No longer having cubicle mates I hosted my first event in January 2015. At the time I loved alliteration and called it Chicago Creative Chics, Coffee & Collaborations. It included all the adjectives to describe the event and type of women it would cater to.

The desire of community resonated and caught on quicker than I anticipated. At the end of the first meeting at Cup & Spoon, one of the women asked when we were meeting again. Without pausing I said, “Next month.” I still had to select a date and find a venue, but I knew I was onto something. The energy from the meeting was electrifying and many of those women developed friendships and business partnerships. Over the course of the next two years (2015 & 2016), I grew a lot. Creative Chics grew into 10 different markets. I had an amazing group of women that helped facilitate the Masterminds in each of these markets. One of the best parts of growth was meeting amazing women across the country who were using their skills to deliver products and/or services.

During this time additional creative entrepreneur communities were created. To stay ahead and competitive in the market I needed to refine the business and focus on the core need. In 2017, I rebranded from Creative Chics to Little Black Desk Society. The new name better encompassed the services I provide while giving me room to grow. I also moved to a membership model for our Masterminds and focused on accountability and relationships. There are many service providers and continuing education opportunities for solopreneurs. However, few businesses focus on truly helping women stay accountable to their goals and implement what they have learned. My 13 years of leadership and management provided me the experience and tools to make this transition happen.

Over the past 3 years, I continuously sought feedback from women business owners, my clients, and members to get a pulse on what worked, what did not work, and what was needed. I filtered that through my own vision for the business to refine the Masterminds and resources created for the members. In 2018, I decided to move the Masterminds to virtual and host each of them myself. This allowed me to create a standard experience for each member and also get to know each member better.

I love where Little Black Desk Society is headed and grateful for the first 20 women who came out on a cold Chicago day in January. The growth of these women’s businesses and their friendships have been the oxygen of my business.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Competition and former clients creating similar business models. It is par for the course in business. Competition encourages me to be alert, not be complacent, strive for excellence, and continue to grow. I am also confident in knowing that no one else has my exact experiences or skill set nor do they see my vision. This allows me to stay focused yet aware of my surroundings.

In business, there is always interpersonal conflict. The key is not taking things personally, treating people fairly, do the right thing, and not letting your ego get in the way. It more challenging as an entrepreneur when your business is your “baby” and the buck stops with you with every decision. However, my experiences and mentors have groomed me well.

You need to have grit as an entrepreneur. There is no roadmap. When you are in the corporate world it is easy to be “successful” especially for type-A, results-oriented individuals like myself. Tell me what you want and I will make it happen. In entrepreneurship, you get to make all the decisions, learn what you did not know you needed, and push yourself mentally and emotionally. It requires a lot of sacrifices, patience, and determination. I love the challenge of figuring out problems and adding new skills to my toolbelt.

Alright – so let’s talk business. Tell us about Little Black Desk Society – what should we know?
Little Black Desk Society facilitates Masterminds, provides performance business coaching, and hosts an online community for women small business owners.

LBDS is known for our Masterminds and it is my favorite part of the business.

I love the conversations and energy that come with women sharing challenges and feedback. Seeing breakthroughs in their business and clarity so they can move forward is extremely rewarding.

What distinguishes our Masterminds from others are the tools put in place to assist with accountability. Each member has a monthly business review they must complete before the Mastermind. It allows them to assess their business needs and plan accordingly. It also allows them to get the most out of the Mastermind because they know their specific need. Too many times as entrepreneurs we are so focused on day-to-day operations that we don’t take care of our business. The reviews encourage members to pull their head up and assess/correct the direction of their business.

Performance coaching is for a handful of clients who desire change in their business and willing to do the work it requires. My background in diverse industries allows me to assess existing practices or processes in a business and provide feedback for improvements. Improvements that will streamline their business, improve productivity, and improve their customer service.

The online community is a place for deeper conversations and support. It allows women to share their experiences, ideas, challenges, and questions they would not otherwise find on Google. It creates a space where they discover they are not alone in facing a challenge. As entrepreneurs, there is not a one size fit all answer. Engaging with your peers and having diverse conversations allows you to pick bits and pieces that work best for your business model. It also exposes you to ideas outside your industry bubble.

The biggest differentiator of our community is the use of a platform other than Facebook. Facebook groups tend to send many entrepreneurs down rabbit holes and provide too many distractions. Our members want to focus on the business at hand. Our community allows members to stay focused on specific business topics and be productive with their time.

Is there a characteristic or quality that you feel is essential to success?
Grit. You have to be committed to your vision and pursue it all cost. Pursue it regardless of setbacks, failures, and naysayers.

Entrepreneurship can be compared to football. There are many moving parts. Personnel and players change from season to season. Fans are fickle and want to coach from the couch. However, as captain, you are the one on the field. You are responsible for the leadership and momentum. You read the plays and have to make in-game adjustments similar to business.

Regardless of who scored first in the game what matters is the score at the end of the game and in between each play and every inch counts. You have to be willing to get up, get back in the game, tune out the crowd, and focus on the task at hand to win.

How bad do you want to succeed and what are you willing to do to make it happen?


  • Masterminds start at $750 for 6-month membership
  • Performance Business Coaching starts at $2100 for 12-weeks
  • LBDS Network starts at $19.99 for monthly membership

Contact Info:

Image Credit:
Artistrie & Co, Melissa Song Photography

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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