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Kendall Cherry of The Candid Collective: “If something rubs you the wrong way, get curious and ask why”

If something rubs you the wrong way, get curious and ask why. There are so many times I’ve been working with potential clients or other people in the online space when things didn’t seem to click. A lot of times I would feel really upset or angry. “Why don’t they just GET IT?!” I realize […]

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If something rubs you the wrong way, get curious and ask why. There are so many times I’ve been working with potential clients or other people in the online space when things didn’t seem to click. A lot of times I would feel really upset or angry. “Why don’t they just GET IT?!” I realize now that what I should have been asking, is what value do I hold true that this other person does not? Usually it just means that you prefer something differently than the other person, and getting curious helps you understand why.


Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Kendall Cherry.

Kendall Cherry is the founder and creative director of The Candid Collective, an online and in-person community for entrepreneurs to come as they are, regardless of gender, age, race, revenue, or years in business. She’s on a mission to create a world that’s more candid and kind, and is based in Austin, Texas.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

If you knew me as a child, you would’ve noticed two things about me right off the bat. The first is that I was a classic daydreamer. I was always staring off into space, looking up at the clouds from the car window, playing “pretend” every chance I got. I would constantly try and create whatever world I would see: writing plays and stories, using our new family camcorder to create fake newscasts, sketching and drawing product ideas or advertisements.

The second thing you should know is that when I was little, I thought I wanted to be an elementary school teacher. I still remember when chalkboard paint first became a thing. My parents had painted one wall in our garage in chalkboard paint, and my mom walked up to our elementary school and bought two of the exact same desks we had in our classrooms so my little brother and I could play “school.”

As a kid, I most often embodied the role of “daydreamer,” “creator,” and “teacher,” and the same is true as an adult. And since this is an article about second chapters, I really didn’t embody those same roles that I did as a kid in my early twenties. I had to sort of rediscover those parts of myself, but that rediscovery is what brought about my second chapter.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Say what you mean and mean what you say.” I think a lot of my early inspiration for my company, The Candid Collective, came from this idea that “honesty is the best policy” — it’s something my parents really drilled into us when we were kids and that has stuck with me as an adult.

I think in life, we try to say things, tweak them so that we don’t hurt people. We tell the white lie to take the edge off, only to have it make the situation worse for everyone later on. I’ve always been a straight shooter, and I remember growing up and thinking “why can’t everyone just say exactly what they’re thinking?!”

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Emotional Intelligence

I remember in high school, my friend group were some of the smartest kids in our class, but I was considered just sort of average. I was a different kind of smart, labeled “gifted and talented,” but I wasn’t your straight A student by any means. Back then, emotional intelligence wasn’t the highly coveted soft skill that it is today. So I was labeled “sensitive” and “too emotional,” and I was sort of cast aside.

But now, I can honestly say that my emotional intelligence is a huge reason I was able to grow so quickly in my old career path in corporate America. I owe a LOT of my success to this soft skill that, when I was growing up, was labeled as a shortcoming. I wish I could tell my younger self to not try and shrink that side of myself down so much, that it would serve me well as an adult. It’s something that I’m really thankful for now that I’ve grown up.

Kindness

A few years ago, I went on my first trip through Italy as a female solo traveler. Growing up in a blue collar household, we were doing good to vacation outside of Texas, so this was a BIG personal milestone for me at the time.

During my journey, I had an AirBNB host in Florence named Mauricio who I befriended, probably in his late 70s? Just imagine the cutest little Italian grandpa, and that was Mauricio. He had rented out his childhood home as an AirBNB, and we would spend our mornings trying to communicate with each other using the Google Translate app on his phone (Mauricio was very with the times, despite his age).

One day over breakfast and near the end of my journey, he’d told me I was “very keend,” realizing a few moments later that he was trying to pronounce the word “kind.” I think being a kind person, looking out for other people and trying to bring them along during my own journey and success has been how I’ve been able to achieve so much so far. I try my best to bring others along with me any chance that I can.

Lack of Patience

I think this one will get some backlash and some eye rolls, but I do think that my lack of patience has helped me find success so far. My brain is highly strategic, and I can usually map out a turn of events, how I think a scenario will play out, very quickly. The same goes for ideas in my business. If I don’t see the end goal looking like something I want for myself, I’m not going to waste years of my life trying to see if it gets better.

This isn’t the case for everything, I do still think that steady growth and a slow burn are really important. But if I don’t like what something looks like at Point A, I’m definitely not going to stick with it to see what it looks like at Point Z. I’ll find a different route.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

Before starting my business in December 2019, I was working my “dream job” in corporate America, and I had the six figure salary, the healthcare benefits, the exposure that most people dream about. I’d been a liberal arts major in undergrad, and had gotten incredibly lucky in my career journey. My first job right out of college was working in the C-Suite at a Fortune 500 company. I had a lot of executive exposure early on, which is incredibly rare.

It was sort of this unicorn job and career path that helped me climb the corporate ladder really quickly (almost too quickly), to where I started to see what my options were if I were to stay in that kind of environment.

And how did you “reinvent yourself” in your Second Chapter?

In my Second Chapter, I decided to start my own business and give up my traditional career path, and the life I’d spent the last five years building. When I finally quit my corporate job to go full-time as an entrepreneur, I essentially gave up everything.

I relocated from Houston, Texas and moved our company HQ to Austin, Texas. I gave up my swanky one bedroom apartment to move back in with my parents. I also didn’t have a business degree, so I was learning business on the fly. And where I could easily navigate my previous job because I’d learned the rules and how things work, I pretty much worked in this new entrepreneurial world where the rules changed all the time. If you know me at all, you’ll know this is way (WAY) outside of my comfort zone and a total stretch for me. But I knew I owed it to myself to really bring this vision for my company to life.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

I’d been working on my business for about a year while maintaining my full-time job and I was totally exhausted. This was also while trying to navigate “living with COVID-19” and I knew I couldn’t hold on for much longer.

In October, my entire business changed around me and we’d grown extremely fast. I could sort of see what it took to get to the next level and I just kept thinking “What would my company look like if I could truly focus on it?” I’d spent the last year with my attention and energy divided, and I knew I owed it to myself and my clients to give this thing everything I had left.

Totally terrifying, because the training wheels and safety nets I’d had for YEARS were gone, but I still stand by it was the right time for me to make that transition.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

At my old company, I was the first person to ever have my job. It wasn’t created specifically for me, but I sort of got to make it whatever I wanted. I was an “intrapreneur” for years, but didn’t really realize it at the time. I started to understand that the next 40 years of my life weren’t spent working for someone else. It’s like I woke up one day and just realized “this isn’t what I want for my life.”

I’d been doing a lot of these skills inside of a company that translated to owning a business — coming up with a product idea, creating the go to market strategy, selling it to customers — even if the programs and products were internal.

I think when I realized that the connection between my intrapreneurial skills looked similar to what it takes to start a business, it became a lot easier for me to understand and see that I might actually be able to do this. As soon as I sort of saw the work I was doing at a company in a different light, I couldn’t unsee it. I knew that the journey would be long, hard, and there’d be a lot that I didn’t know (yet), but that I had what it takes to make it happen.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Things have been moving extremely fast and slow at the same time. I recently did a major rebrand of basically my entire online space. We changed names from my previous name of “Candid Kendall” to The Candid Collective, and I knew I needed help with hiring a graphic designer. I’d been basically designing everything myself for a year and was the epitome of “fake it ’til you make it.” I had ONE graphic design class in college and I knew when I left my full-time job to work at my own company, we needed to invest some of our money into the branding space.

And it probably doesn’t sound like much, but surrendering artistic control of “my baby,” my brand and business, and aaaaall of that ugly graphic design work I’d been doing myself was one of the hardest moments as a business owner so far. It took a lot of trust for me to be able to really let somebody in on this vision in my head, and then let them hold my baby.

Luckily, I found Madison Pidcock at Madison Grace Creative and she was able to take my ideas and really bring it to life. I had told her about this crazy big vision I had for a future coworking space and coffee shop in Austin, Texas, that I wanted The Candid Collective to be one random Friday, a few months before we started working together. So when I finally decided to hire a graphic designer, I just knew it had to be Madison.

One thing I’m really passionate about while building my company and our brand is this belief that good ideas can come from anywhere. It doesn’t matter how old you are, what color your skin is, if you have a college degree. There is a LOT of work that has to be done to really be able to make something as inclusive as this a reality, but hiring Madison was sort of this nod to the future vision. Our mission is to build a safe space for entrepreneurs to come as you are, no matter your gender, age, race, revenue, or years in business.

Madison Pidcock is a very mature person, and any time we talked I felt like I was talking to someone in their late twenties, just like me. I didn’t know this until a few weeks after hiring her, but Madison wasn’t even legal drinking age when we started working together, but you’d never know it from her work. Same goes for her education.

Madison had dropped out of college and decided to not go back a couple of years ago, trusting her own design talents over a piece of paper. I had no idea about ANY of this when I hired her, and it was sort of this great homage to how I want The Candid Collective to be this equal opportunity hub, a place where we bring together incredibly talented people from a ton of different backgrounds.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m most thankful for my best friends, Jess Potgeiter. When I first started my business, I really didn’t have anyone in my circle who had started a business. I pretty much worked alone in my house in the wee hours of the morning and later hours at night. Most people around me still held traditional jobs, so I was constantly surrounded by negativity or people trying to convince me to just stay where I was.

But then I met Jess. The best way I can describe her is that she’s this Australian bundle of joy who is obsessed with pink and positivity. We became friends right around the time I first launched my business, and she’s been there with me through every high and low of early entrepreneurship so far.

I’m grateful for her for many reasons. One thing you need to know about me is that sometimes, letting people in to see me when I don’t feel perfect or when I am “actively failing,” is really hard for me. Jess is usually the first person I call when I need to remember that I can achieve anything. I’m most grateful for her because she has this really unique way of leaning into positivity. She does it in this totally human way that’s not like Polyanna or syrup-y sweet. You’re allowed to say that “this sh*t sucks” but still find the good and the growth in that. I think everyone needs a Jess in their lives.

Can you share the most interesting story that happened to you since you started in this new direction?

I’m not sure how interesting this is, but part of my second chance was relocating from Houston, Texas, and moving back in with my parents. Previously, I was living in this bachelorette pad apartment with a skyline view of downtown Houston, but I gave that up and moved back in with my parents.

I used to have so much pride about having to go back to living in my childhood home. I still remember thinking when I first started my business that I would NEVER in a million years do something like that, but then when COVID-19 happened, I didn’t want to spend all of quarantine trapped in my apartment alone. Most of my friends moved away from Houston during COVID, so I was spending a lot of time at home. My parents are also retiring soon, so it sort of forced me to think about where I want to put roots down.

It’s been a really interesting transition until I finally save up to buy a house. We all sort of keep to ourselves except for our afternoon game of pickleball or to watch any of the new Magnolia Network shows that are out on discovery+. I’m also really appreciative to get to spend this time with them because I know that won’t always be the case.

We definitely still have our blowups like any family, but I’m trying to lean in to being more tolerant of the little things that we might do to annoy each other. Plus, we have a household of animals, so some days it literally feels like a zoo.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I think this sort of just goes with the territory, but I go back and forth with believing in myself. All the time! I think this usually shows up for me when I identify as an “entrepreneur.” It’s one of those buzzwords that a lot of people use, but sometimes, I still forget that’s who I am not, and that’s what I do for a living.

When it comes to overcoming limiting beliefs, I usually try to lean back into who I am as a person. What are my strengths? What do I contribute to the world? Much like how I was as a kid, I’m a daydreamer, a creator (more specifically, a writer), and a teacher. Whenever I feel any limiting beliefs, I try to turn back to these very basic pieces of who I am.

Sometimes it means taking a few days off from screens and journaling out my vision like a daydreamer. Other times, it’s writing little poems and blurbs about different people or things I see in the world like a creator. Other times, it’s recording a podcast episode or reading a book on a topic I want to learn more about like a teacher.

I try to get back to the main core of who I am, the person I would be without the corporate career path or The Candid Collective. I like to ask myself, who is Kendall Cherry? And then I work backwards and try to do that thing in some of the simplest or most basic ways.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

To be honest, this is something that was incredibly difficult for me when I first started out my entrepreneurial journey. I really didn’t know any other business owners in my circle, and I didn’t really appreciate how important community was for me. I think it’s why I’m so passionate about it now.

Once COVID hit, it became even harder to network and meet people. I couldn’t just go to a coworking shop and hang out like I originally thought I’d be doing. I’d only been in business a few months when the pandemic hit, and so I very quickly realized I would have to create a fully online business without any in-person networking, which wasn’t exactly in the plan.

As my business eventually morphed into The Candid Collective, it’s how I also created the support system I didn’t have on my day zero, when I first started out as a new business owner. As I’ve officially transitioned into full-time entrepreneurship, I now have people around me who not only believe in the work we’re doing as a company. They also back me up on the hard days, on the days when you feel like you are constantly hitting a wall.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Even though I have a background in PR and communications, I am usually way more comfortable when I’m supporting someone else. I don’t like being center stage or the star of the show. I would much rather be the person who’s backstage.

So when it came time to start a business, I grossly underestimated being the “face” of my company. In some cases, this even looked like struggling to get visible on social media or having fancy photoshoots done, with me as the main attraction.

Before I started my business, I was not a social media influencer by any means. In fact, I hardly posted anything online at all. Getting out of my comfort zone meant being okay with telling my story, and being the one telling it, especially on places like Instagram Stories. I usually just try to swallow the pill and remember that the story I’m telling is here to help just one person. And so I try to talk to that one person. It’s not a perfect solution, but it definitely helps.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. You will fail constantly. When you start a business, there is no hiding behind bureaucracy or punting the problem to your manager. It means you’re held accountable for basically every decision, project, milestone, or interaction in your business in some way. Which means that your margin for error is astronomically high. You’re going to feel like you’re failing all the time (which is true, you’re failing a LOT), but it feels a lot worse than a traditional career path because there’s less buffer. You can’t just shift the blame to someone else like in a traditional job.
  2. Celebrate the small wins. See #1. There will inevitably be hard days, and a lot of times they compound in a way where you’ll get several bad days in a row. One of the best things I’ve learned recently is to celebrate even the smallest of wins. I tend to be excruciatingly hard on myself, and so if I’ve got a lot of losses starting to stack up, that’s about all my brain can focus on. It becomes a vicious cycle. So celebrating the small wins helps me to reframe and remember that I’m on my own journey, on my own timeline.
  3. Turn off notifications. When you’re running an online business, there are a million places you need to show up. Instagram. Facebook. Email. Slack. Clubhouse. There are literally hundreds of notifications that can pop up on your phone. I knew this was just sort of the name of the game when you own an online business, so I outsmarted my productivity and removed pretty much all notifications on my phone and computer. If I want to check for messages, I get the choice of opening the app when I want to, versus being a slave to the screen.
  4. Build the business you daydream about. When I first started, I thought I wanted to be a career coach, until I realized that I want to help people bust OUT of the corporate working world for good. I had several iterations in my business model which were good for me to learn from, but it was never what I actually daydreamed about. I was constantly comparing myself and my business to everyone else online, until I realized that I needed to do things in my own way. I wish I would’ve been brave enough to trust my daydream from the very beginning, because I find that that’s usually what we’re meant to be doing anyway.
  5. If something rubs you the wrong way, get curious and ask why. There are so many times I’ve been working with potential clients or other people in the online space when things didn’t seem to click. A lot of times I would feel really upset or angry. “Why don’t they just GET IT?!” I realize now that what I should have been asking, is what value do I hold true that this other person does not? Usually it just means that you prefer something differently than the other person, and getting curious helps you understand why.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

My movement would be to create a world that’s more candid and kind. I think that a lot of the problems we see in the world today could be lessened if we were able to be honest about how we were feeling. If we stopped hiding behind what we think people want to hear or what we’re scared to say. I also think if we were all a little more empathetic and looked out for each other, simply for being human, the world would be a better place. It sounds so simple, but it’s way harder to do in practice.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

I’d want to meet with Dolly Parton and pick her brain about a few things. I really look up to her as a philanthropist and for the way she’s given back to her community, even after coming from nothing. She’s one of those leaders that resonates with people no matter your age, gender, race, you name it, and it’s something I aspire to bring into the world one day.

How can our readers further follow your work online?

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Thank you so much for sharing these important insights. We wish you continued success and good health!

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