We were lucky to catch up with Kaila Lindsey recently and have shared our conversation below.
Hi Kaila, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?
“When I grow up, I’m going to be an artist”
I was 7 years old telling my mom my life goals and when asked the question of what I was going to be when I grew up, the answer was ‘an artist’.
My mom, trying to protect me as all mothers do, pointed out the perils of being a ‘starving artist’ in hopes that I would understand a lesson in hard work. To which I replied “Well, then I’ll marry a rich man and then do my art”.
Ahh the logic of a child… My mom bestowed one of my greatest life lessons on me that day, even if she didn’t realize it at the time. She stated that I needed to make my own way, be my own person and make my own money … and THEN do my art to fill my heart.
From that day forward I set out to pave the way to create and dream and grow. It bestowed in me a deep burning desire to achieve where others have not, including those in my family. This desire pushed me to a place that I never would have imagined and opened doors over and over again pushing me on to my next level. All from one simple conversation so many years ago.


Thanks, so before we move on maybe you can share a bit more about yourself?
For so many years I fumbled along looking for my place. The career I could put down roots and truly shine. Where I could grow and expand without limits both financially or physically. I came to my career in real estate in probably the same way most do… the desire for FREEDOM.
The challenge with real estate is that FREEDOM is exactly what you get. The freedom to soar… and the freedom to fail… and fail splendidly at that.
I made the determination to buckle down and focus. The goal became to hustle hard so I never had to hustle again if I didn’t want to. Since then I have invested time, money, focus and mindset to learning as much as I can and applying this knowledge. I also made it an action to teach others how to reach their financial and business goals.
Along this journey I also realized there is more to life than chasing the dollar. I focus on business for the PURPOSE of having a life I love to live every day. I spend my spare time with my family and son, rescuing dogs, painting and more. Life is too short to look back one day and realize you spent the whole time living for tomorrow or the future.


There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Networking / people
Finance
A Passion
When I got out of college i had no idea how to network. I thought it consisted of showing up to events and finding people who wanted what I was selling. If not… then it was a failure. The art of networking is the art of people! Learning HOW to meet people, learn what they desire in life, and pouring into them. Then the 6 degrees of separation does the rest! This is true in business and in your personal life. Every opportunity, interaction, program, event etc that I’ve ever been involved with has guided me on a path to where I am, and without each and every one of them I would never be where I am today. Get to know others and you will open your world to amazing opportunities.
I never knew growing up how to actually retire. My parents didn’t know how to teach me as they didn’t invest or plan for the future in that way. For generations you would get a good job, a pension or 401k and that was it. When I went off on my own I was great at saving, but had no idea how to invest. I can only imagine what I could have amassed in my life had I started investing all those years ago. I now know exactly how I can invest and grow and create a true path to retirement on my time even as a real estate agent (this is a myth for most).
The reason understanding finance and investing is so important is it is the path to freedom from the daily hustle. We never know what is going to happen to us in life, and with a plan you can explode into each new year with certainty. It removes a lot of the fear surrounding the future.
Lastly, a passion… something that brings you joy outside of your family and friends. For me that passion is surfing and art. I LOVE to paint and LOVE to surf. These 2 opportunites allow me to get into my zone and be expressive and creative. I can turn off everything else (especially when surfing b/c I can’t do it with my phone). I am far more focused at work when I have time to express myself. With that I will add a passion for doing good. I have fostered 58 dogs in the last few years and each and every one of them has taught me something about love, patience, and joy. It fills my soul and gives to someone/something else in this world. Good energy is important to share 🙂


What was the most impactful thing your parents did for you?
I give my parents a lot of credit. While I did not grow up wealthy in any sense of the word, as we were faced with foreclosure of our home and repossession of a vehicle, they did instill in me work ethic and a drive to achieve what I desired. They taught me what they could and helped me find those with the answers to questions they couldnt help me with.
Aside from my lesson on making my own way, there are 2 financial lessons my parents taught me that stand out the most. My parents were the type that when I had a question, they would ask me a bunch of questions to help me answer my own question vs just give me the answer. As a kid it drove me NUTS, but as an adult I appreciate that they did it. A lemonade stand was not priced at a random price… no we had to figure out the cost of water, Crystal Light, time, and cups to deduce the price for the lemonade lol
Lesson 1: Savings and Spending
I was not permitted to wear colored nail polish to school (a pass down rule from when my mom was a kid) so every week when i went with my friends to get my nails done, instead of $5 for my nails, it cost $7 (plus tip) to do a french because I could wear french to school. Yes these were the prices for nails in NY in the 90s. SO…. one day my mom pointed out that each week I was spending 70% of my allowance on my nails…. it then dawned on me that I should save that and buy the polish and do it myself. I did my own nails for the next 20 years until it made financial sense to have someone else do them (when they lasted weeks not days)
Lesson 2: Don’t Make Bets
TO this day I still do not bet on anything. I make educated investments. This all came from a claw game…. I was at the horse ranch we went to often in summer and i wanted a pocket knife in the claw machine. I spent my entire allowance ($20) on the game trying over and over at $1 each try to get the pocket knife. When I was finished, my dad pointed out that instead of wasting the $20 and being set back, I could have saved up several weeks allowance and been certain I would get the knife by purchasing it. Sometimes the investments that seem small and “easy” turn into money pits that have no returns. Go with what is certain or certain enough
Contact Info:
- Website: https://www.livingincharlottenc.com
- Instagram: https://www.instagram.com/kailalindseyrealtor/
- Facebook: https://www.facebook.com/kailalindseyrealtor
- Youtube: https://www.youtube.com/@livingincharlottenorthcarolina


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