Story & Lesson Highlights with Tosha Wilson-Davis

We recently had the chance to connect with Tosha Wilson-Davis and have shared our conversation below.

Tosha , it’s always a pleasure to learn from you and your journey. Let’s start with a bit of a warmup: What are you chasing, and what would happen if you stopped?
Currently, I am chasing purpose. I always tell my clients to chase their purpose and passion, and the paper will always follow. That simply means when you chase what brings you joy and satisfaction, you feel fulfilled, and the work never feels like labor. The money or paper naturally follows. I am pursuing my true purpose, which is to become a full-time entrepreneur serving people and helping them find their career purpose and even their dream home. I started Penciled IN Resume Writing & Career Services, LLC in April 2019, and we are still here because I never gave up. Even when it has gotten slow and tough, I still kept moving forward. But, I am also a Licensed Realtor here in Georgia and own Penciled IN Realty & Investment Services, LLC. So a CEO x 2.

If I stopped chasing my purpose, all my dreams would be shattered and then, the what-if settles in. Entrepreneurship is about freedom, and that would be lost if I stopped now. I have come too far to look back or push the brakes.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Tosha Wilson-Davis, and my brand’s name is Penciled IN. I am the CEO and Founder of Penciled IN Resume Writing & Career Services, LLC and Penciled IN Realty & Investment Services, LLC.

Penciled IN Résumé Writing & Career Services, LLC is a full-service career services firm. Our clients can feel good knowing that they are in good hands with us as we have served 220+ clients, including college students, educators, industry and federal government employees, & insurance executives. We take pride in providing each client with quality time to build a solid career plan/strategy that aligns with his or her background, purpose, and future career goals.

I have 10+ years of professional résumé writing experience, which includes the creation of winning CVs for higher education professionals and federal government résumés for those seeking civil service positions. As a small-town girl, hailing from Butler, GA, I have always had BIG dreams and have paved the way to making those dreams a reality. I am a Certified Professional Résumé Writer (Strategist) and a Certified Employment Interview Professional. Both certifications were earned through the PARW/CC. In December 2024, Penciled IN Resume Writing & Career Services was awarded Best of GA Honorable Mention 2024 and was nominated for 2025. Those results are pending and will be revealed December 4.

Established in April 2019, Penciled IN is here to assist clients not just with building a winning resume but also with preparing them for the interview and beyond. Penciled IN offers 100% virtual and in-person services at our Warner Robins location. We are currently working on a final component that will allow clients to be their best versions as they prepare to interview for roles. I am excited about this venture, which will serve all career women in the Middle GA area, Penciled IN’s New Dress Like A Boss Career Closet! Expected arrival of this portion of our business is December 1, 2025. It will be free to those clients who purchase our services, and available to the general public for a small fee to allow us to keep the closet stocked.

Penciled IN Realty & Investment Services, LLC
I became a Licensed Realtor in January 2023 and am currently brokered by Southern Classic Realtors. I have hit a major milestone this year, closing 13 transactions and $2.6M in sales, becoming a Multi-Million Dollar Producer. I have also served eight first-time homebuyers and was recognized as a Top Agent and Best of Zillow, January – July 2025. I also have a land investment that I am working on, and looking forward to serving many more clients in 2026.

Penciled IN is a brand, and I take pride in providing exceptional service, excellence, and experience to all my clients. I have a motto for both of my businesses and it is pretty simple: Do the Work, Do It Well, and Take Care of the People.

Amazing, so let’s take a moment to go back in time. What’s a moment that really shaped how you see the world?
I have had many experiences that really shaped how I see the world. I became independent during my undergraduate college years, which opened my eyes to a higher level of responsibility and adulthood. I graduated in December 2004 with dual Bachelor’s degrees, and that moment taught me that anything is possible in this world, if you have a desire and the determination to make the most out of it. Being away from family and having little financial support really showed me that no one will save you, so you have to have a strong work ethic and be willing to make sacrifices to survive. I learned that early on, and it has really shaped me into who I am today.

What have been the defining wounds of your life—and how have you healed them?
The loss of my father on December 14, 2022, shook me. It was one of the hardest and emotionally draining moments in my life. I was one day away from taking the state licensing exam for real estate, which was set for December 15, 2022, at 9:00 am. Around 8:03 am on December 14, 2022, I received the news that my father had passed. I was crushed to my core, and it still feels quite heavy. Yet, his knowing I was a go-getter and a success story for my family before he left this world has given me the necessary push to keep moving forward. Days, weeks, and months have been so tough for me. Yet, I have unshakable faith, and knowing that he is resting and no longer in pain provides me some comfort.

Since he has left this world, I have become a Licensed Realtor, passing the state exam on January 5, 2023, two weeks after laying him to rest, have two Billboards on Watson Blvd in Warner Robins, have bought my dream home, and became a Multi-Million Dollar Producer for 2025. I was also recognized as Realtor of the Month on August 31, 2025. I could have given up, but the determination and motivation to keep the momentum even in the face of adversity show your true strength. I know he would be proud.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What’s a belief or project you’re committed to, no matter how long it takes?
I am committed to becoming a full-time entrepreneur and a Real Estate Broker. I have always been a servant and a leader, and I am committed to sticking to my goals and moving forward with this venture. I have been a Professor for over 16 years, so training and mentoring are my passion areas, and I am excited about seeing that dream become reality to build and develop successful agents who care about their clients and deeply believe in service above self. Being a Licensed Realtor is hard work, but when you do so as a servant, keeping your clients top priority, it is such a rewarding experience. Customer service, compassion, and integrity are all a part of this profession, and all three have to be at the forefront. I am not sure how long it will take to accomplish this goal, but I have set some milestones to keep me on track, and 2026 is looking bright.

Okay, we’ve made it essentially to the end. One last question before you go. Could you give everything your best, even if no one ever praised you for it?
I say this all the time, applause is extra noise – it is a supplement of your hard work, but not a necessity. I have done some extraordinary things and big accomplishments as a small-town girl from Butler, GA. Although the applause may have been light, that didn’t dim my light or my passion to keep breaking barriers and making history. My work is to prove to myself that anything is possible, not to receive applause from others. The applause and praise are bonuses, but they aren’t required for me to know who I am or to unlock the next levels! That is what I want every entrepreneur to understand so they keep moving up the leader’s ladder!

Contact Info:

• Website: https://penciled-in-resume-writing-career-counseling-a.teachable.com/
• Linkedin: https://share.google/4NYTUQAbLXhA0exAr
• Facebook: https://share.google/2xSW3TQlrA3DVJ9Jz

Image Credits
Lawrence Ray (Talk to Me Nice Studios)