We were lucky to catch up with Kelly Whitaker recently and have shared our conversation below.

Kelly , thanks for taking the time to share your stories with us today What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?

My heart was pounding so hard in my chest that I was worried he would be able to hear it through the phone. I was seconds away from having an honest – yet – difficult conversation with my boss, and even though I knew it was the right thing to do, my nervous system was spiraling in a full body panic. I had practiced my speaking points over and over but my fear of freezing up, going blank, or the dread of an unexpected a negative reaction made me want to hide, ideally in a hole in the ground, never to be found again. The desire to avoid the conversation altogether was unbearably tempting – Why put myself through this? Things aren’t SO bad, are they?

I wanted someone to help me. Someone I could practice with, help me release the nerves that had constricted around the words, make sure my talking points were clear and impactful so I could begin this conversation with poise and strength instead of shaking in my slippers. Why didn’t that exist?

Shortly after the conversation with my boss (which went surprisingly well, in spite of my angst), the idea stayed with me. Why *didn’t* that exist? If I needed a space like that, surely there were others that did too, right?
Months later, Kelly Convos moonwalked onto the scene. If that space didn’t accessibly exist yet, it was clear to me that I was the one to do it. I recorded my first video on the floor of my apartment, sweatily and earnestly offering a friendly and nurturing space to build up communication skills and move through difficult conversations that would otherwise be avoided. My mission was simple but viral – removing the fear from communicating, empowering people to speak up for themselves.

Over the following 3 years, I would build, slowly but surely. Juggling a pandemic, a day job, imposter syndrome, and a new cat, I welcomed one client at a time, a parade of diverse and critical needs from people dedicated to doing the right thing but struggling to find the words and confidence to be heard. As each piece came together – the website, the socials, the pitch and the fresh mystery of an LLC – I began to understood just how big of a need this was in my community and our society. Communication is a skill that’s deeply needed and expected, but it isn’t accessibly taught. Through my blossoming presentations, workshops, and writing features, I would provide the space to learn. That space would be warm, fun, empowering and effective and allow people to step up for themselves and ask for their desires.

In August 2023, I rallied the nerve to quit the day job and jump in with both feet and my whole heart.

Kelly , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I partner with people who long to speak up for themselves but don’t have easy access to the words. People who shy away from addressing conflict instead of facing it head on.
People who feel guilty about setting and holding boundaries.
Leaders who feel discouraged about tension growing on their team but don’t know how to address it.
People who hold a lifelong terror of public speaking.
People who don’t know how to say no.
People who are don’t know how to be direct without isolating or offending.
People who are drained by conversations they need to have but don’t know how to start them.
People who long to be understood.

Together, we uncover the right words for the situation. We learn to personalize the message specifically to the recipient, the art of Speaking to your Audience. We practice until there’s no fear connected to the message, only ease and clarity. We find the power of sitting in silence once the request has been made. We unhook expectations from the result, releasing all things we cannot control. We uncover the power of listening, thoughtful questions, “I statements”, and many, many deep breaths.

What’s been the most effective strategy for growing your clientele?

Finding myself as an unexpected entrepreneur, the best way to grow my clientele is to Be Seen. As much as I would love for my clients to stumble upon my website, the uniqueness and personalized nuance of my work is much easier to be understood in person. This has not been easy for me, as an unassuming introvert, slowly building back up social stamina from the pandemic, but something I have needed to push through because it has proven to be the most effective. Seeking out and putting myself in a space surrounded by leaders has proven to be the best way to have my business be known, find clients and generate referrals. Queer spaces and non-profits have been particularly effective communities for me due to their growth and community-focused energies.

What’s a lesson you had to unlearn and what’s the backstory?

Imposter Syndrome has been, to put it mildly, a hateful hurdle. I never anticipated myself running my own business and being my own boss, so finding myself doing so stirred up a flurry of doubts. The work I do and the way I do it is unique and doesn’t fit neatly into the boxes that capitalism provides for us, which gives the fears many places to grow. The What-If’s are bountiful and persistent : What if we fail? What if we get laughed at? What if no one wants this? What if you aren’t doing enough? What if you lose all your money and have to move back home in disgrace? Daily, I have to re-ground into the trust of myself, my mission, and my capacity to deliver with this work. What I coach in people is how I coach myself – learning to let the voice of confidence and purpose be louder than the voice of fear. I have learned that courage isn’t the lack of fear, but feeling that fear and choosing to do it anyway because you know it’s right. Sometimes it feels like optimism rooted in stubbornness, but whatever it takes to keep moving the needle. Because I know there are people who need me, and I am dedicated to empowering and inviting ease, for the good of all. So Imposter Syndrome can HUSH, because baby we’ve got work to do.

Contact Info:

• Website: www.kellyconvos.com
• Instagram: @Kelly_convos
• Linkedin: www.linkedin.com/in/kellywhitaker44/