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FV 21 | Critical Thinking


In this episode:

  • How your natural personality can shape your beliefs
  • The power of asking questions about the things around you
  • How to teach yourself to question your beliefs

It takes people quite a bit of time and effort to learn critical thinking, especially if they were raised in a background that discourages asking questions. Born and raised in a Bible Belt, conservative, red state community that frowns upon those who ask questions or think differently from the crowd, Carrie Flynn grew up going with the flow to avoid the discomfort of disagreement and confrontation.

Meeting the person who would become her husband gave her a wake-up call for her shift towards being more open minded and progressive – a transition that she continues to nurture to this day. She shares how she went through this transition in this conversation with Meghan Lamm. Pointing out some of the similarities in their experiences, they talk about the tendency of a person’s natural personality to shape their beliefs, the power of asking questions about the things around you and the importance of teaching yourself to question your beliefs.

Listen to the podcast here:

The Power of Asking Questions With Carrie Flynn

Carrie Flynn is joining me for another installment of our “Power of” series, where I’m speaking with women who identified as conservative before switching to more liberal or progressive views.

Carrie shares how she grew up around republican values and what precipitated her gradual shift into more progressive views. Ready? Let’s get started.

I’m really excited to have this conversation. I have been loving these conversations that I have been having with everyone and I’m excited to chat with you today. Before we dive into the good, meaty stuff, tell us who you are and what you do in the online space.

I’m Carrie. I own a company called Virtual Simplicity. I’m an online business manager, but I’m also a Kajabi specialist. Basically, what we do is we help our clients get their Kajabi platforms set up and ready to launch, simply, easily, efficiently—not complicated. They’re able to launch their programs and maximize their profits. That’s our overall goal as a business.

I live in Jacksonville, Florida. I have a husband that I’ve been married to for almost sixteen years. We have two daughters, one that’s almost 12, and a 4-year-old.

She’s 4 already?

Yeah. She’s sassy, stubborn, tactless and they’re both pretty awesome. I was a teacher for almost fifteen years. I taught full-time while I built my business and now, I work from home the majority of the time, which is pretty awesome.

That is awesome. I always love to meet a fellow LBM.

I still do that—I still am an integrator. But I also do Kajabi set up projects as well. I do both.

Better you than me! I guess we’ll jump in. Can you tell me a little bit about your background as a conservative or as a Republican, if you ever identified as a Republican?

Yes, I did. I have a similar background to a friend of ours, Tasha Booth at The Launch Guild. She and I both came from the evangelical space if you are familiar with that.


I would say probably around nine years old, my parents became Christians. I’m from the South—for those of you who aren’t aware of where Jacksonville is—it’s a very conservative area.

In the Panhandle?

It’s not the Panhandle, but it’s literally the same area, just all the way to the East Coast. Very close to Southern Georgia, about an hour South of there. The majority of my life has been spent here and we moved here when I was almost nine.

I grew up in the South, very Bible Belt-ish. My parents did not become Christians until I was probably 9 or 10, but we went to a church. I didn’t know at that time, because I was little, but it was very fundamentalist—if you’re familiar with that. Very strict, lots of rules and very conservative area here.

I am an Enneagram 6.

Me too!

I am not counterphobic—I’m very much not a question asker. That is not my nature. I’m married to someone who is a question asker, so I have become more comfortable doing that in my adult years. But I was very uncomfortable questioning any of this stuff that I was learning. I’m much more of a go with the flow type of person because I don’t like making waves. A confrontation is very uncomfortable to me. I grew up in a very strict, conservative church.

My parents were not as strict like that, but the church that we were in was. My parents were pretty conservative. I came of age as a teenager during the Clinton presidency. My parents were big Bush people, and my parents were Baby Boomers—so were raised to believe certain things about being conservative.

When I graduated high school, I attended Liberty University. When I went to LU, it was dad, Jerry Falwell, not the son. Jerry Sr. was still alive. That was a very interesting experience because it takes all the church stuff, the conservative stuff, and puts gas on a fire and it makes it bigger.

That’s my building block of being a conservative is I was raised in a church, religion, Republican community. That was everything you needed and everybody believed all that stuff. If you were asking questions, they looked at you funny. You were ex-communicated, for lack of a better, phrase from the community.

You get ejected pretty fast.

Especially back then, it’s not like it is today. It was different. You didn’t question. It was the ‘80s and ‘90s, and the early 2000s, it was pre 9/11. Nobody asked a lot of questions. Everybody was trying to live their best life and go with the flow. It didn’t mean problems weren’t there—it meant nobody was really asking questions and it was not encouraged to critically think or ask questions.

I would say probably pre-9/11, pre-Iraq war, even pre-Tea Party before 2010, it very much was like, you didn’t talk about politics.

No. My mom is still like that if you can believe it.

I can totally believe it. My mom hates talking politics.

“I don’t want to talk about it, both sides are a lot of ‘blah blah blah.’” My mom hates confrontation—like worse than me.

Your story is so similar to mine, except for, I was raised in religion from birth, basically.

My grandmother is Christian too. We were raised around it—but my mom and dad didn’t get into it until I was a little older. My grandmother had us at church every time we were there visiting her. We were always around church since we were born.

We were Lutheran, so we weren’t like in the evangelical fundamentalist circle. It was very different. I would say same themes, obviously, just not as intense as it is in like the Bible Belt area in America—very intense down there. What would you say precipitated a shift in your views?

It’s been interesting. I didn’t leave Liberty—I didn’t leave Liberty, but I met my husband right at the end of my senior year. A friend of ours got married and we met at her wedding. We were really young. I was 22 and he was 21. My husband’s parents were Christians also, but he was raised in a very different way than I was—or at least exposed to different things as a Christian growing up that way. And he’s a natural question asker.

His parents encouraged critical thinking. It was very different, even though they’re in that Boomer category also. His growing up years, it wasn’t discouraged for them to ask questions and that kind of stuff. When I married him, we would have these conversations—I’d never asked a lot of questions about stuff. I just always want to believe. My husband was not like that. He’s an (Enneagram) 7 and has an 8 wing, very not afraid of confrontation. Honesty is his number one core value. He likes to talk things out. I was not like that at all, especially at 23.

Now at 39 I’m much more comfortable with it, but at that age, no. Marrying him was—I don’t want to call it the catalyst—but it woke me up to critically thinking about things. He would ask me questions about why I thought this and this, things that I was just taught. We would talk a lot about stuff. It would really get me to thinking. That was the starting point of it, I would say.

Then, over the years, from 22 or 23, until now, and you’re the same age as me. So we had 9/11, Iraq war. My husband and I bought our first house, had a daughter and then the economic crash happened. The value of our house dissipated immediately. As an adult—all that happened. After that, it was the 2016 election. It’s like one thing after the other happening.

The biggest shift for me as a conservative was very slow. I was much more right wing when I was in college, and very slowly over time that shifted to being a centrist. Then, when the election happened in 2016, that was it for me.

Nothing to cling to after that.

It was a big change for me because we were taught at Liberty and taught before then how important character and moral character was. They drove that stuff home back in those days. It was interesting to watch people in my faith community toss that aside because of a one topic voter or because they can’t see themselves voting Democrat or whatever the reasoning was.

That was really hard for me. Then—this happened a couple of years later in 2018 when I did finally ask questions about certain things—like why church people were anti-gay people? Or the discrepancies in the way they were talking about that—what they believed about it versus what they were showing and what they were saying? Nothing lined up to me. I went to the Gay Pride Parade in 2018 with some friends to support the gay community in our area, and that caused a lot of shit in my church, just because we went. It was a huge problem and that was a huge issue.

That situation being the black sheep of the church—which we don’t attend, we ended up leaving. We don’t go there anymore. I do have to say as a caveat, that not everybody there treated me that way, but it caused a hullabaloo with some people there. That was a catalyst for something that was happening anyway. I was asking a lot of questions internally about why I believed what I believed, and some of those values were conservative.

You tend to see conservative views from people who don’t like people who are different from them. Click To Tweet

When that happens, that pushed me over the edge into being a lot more progressive. I was probably always progressive, but I didn’t know how to think for myself and feel safe because that’s a six thing, feel safe for myself.

My husband made me feel safe to ask questions and then as we got older, you care a lot less as we get older about stuff.


I’ll be 39 in December 2020. One last thing is, becoming an entrepreneur gave me a lot of confidence in myself that I can make. I’m sure you probably feel that way too and that aided in that being more confident in other areas and less scared, too.

I feel like the more I’ve stepped into entrepreneurship and learned more about myself, the less I was worried because I came from teaching too, into the online world. There’s such an emphasis as a teacher on how you conduct yourself in public spaces and online. At least in the schools that I taught at, it’s like, you’re never really “off”. You have to be constantly mindful.

Especially, because I used to teach in small towns, you have to be constantly mindful of like, who might see you, if you go out to the bar on a Saturday or like, what kind of pictures are you posting on Facebook, even if you’re not friends with any parent on the internet—like that kind of stuff.

When I switched into online businesses like, “You mean I can like use the word ‘fuck’ and say whatever I want?”

It was such a difficult transition because in the very beginning I was like, “I can’t do any of that stuff. I have to be buttoned up, prim and proper.” Then there was a point where it was just like, “Fuck it! Take off the bra! Do whatever you want!”

That’s how I fell about cussing too because I tend to cuss at my house. I always talk how I felt comfortable at the house and still it’s hard for me now. I was a teacher too for a long time, and I’m still teaching a couple of days a week. There is an element of being a little bit nervous about “can I be myself?” because I still live in a very conservative area and it is a little scary to be yourself.

Especially, now, the way things way people react to stuff. It’s like pretty hard, but I will say, as I’m progressing, like you had said, being an entrepreneur has really helped me to be more comfortable. If I throw in a cuss word here and there, it’s not going to be the end of the world, basically.

I was the same, where I would speak however I wanted to at home when I lived in Virginia, but I would really censor myself when I went out into public because I still lived in a very conservative area and a small town where I grew up. A lot of people knew me. I would just censor myself a lot. Not that I’m going anywhere right now, but I definitely don’t do that now because I moved, and I hang out with people who also don’t feel the need to censor themselves.

It’s like we can be situationally appropriate—but also, we’re not like—

Socially appropriate.


I am a little bit younger than you. I’ll be 33. I didn’t graduate, like the year I graduated is the year the stock market crashed. That was the year the Great Recession started. My experience with all that was a little bit different, being a little younger, because I was a teenager during the Bush era. If I could have voted in 2004—I was a year too young—but if I could have voted in 2004, I would have voted for Bush.

I voted everything—if you can imagine it, I have voted it. I’ve voted conservative, third party, Obama, liberal. It’s hysterical.

There were several years after I could vote that I didn’t, and then for a long time, I was just a presidential voter. We would only vote for the president.

When you live in a very conservative area, one of the things that happen sometimes—many states have a closed primary. What happens in the local elections often, is they’ll use tactics to close the primary, but the elections will basically be decided in those primaries. It shuts out anybody who’s not registered.

I’m registered as an independent.

In our area, this is a heavily used tactic. Many liberals are actually registered Republicans so they can vote in the local elections.


People who shouldn’t be running for superintendent or school board. That’s very frustrating when they do that, because then I never changed my back because I just don’t care. It’s a label to me at this point. I’m not like all up in arms about it, but for some people it is a big deal and it’s super annoying to have to go change it back.

That’s something really interesting being in the conservative space. I have no idea if that happens on the other side or not. I’ve never lived in a heavily progressive place before, so I don’t know, but it does happen in our space.

I’ve actually been seeing some chatter about that online. I’m in a couple of really large Facebook groups, obviously very progressive Facebook groups, although there’s a good mix in one of them, of people who identify as a Republican but are not going to vote Trump in 2020.

That’s happening around these days, that’s for sure.

There’s a lot of chatter—somebody posted something recently about there being a lot more registered Republicans in 2020 or something, like this election cycle than last and that was concerning for them. There were a bunch of people who commented that they changed their registration to Republican so that they could vote in the primary in their state and they just never bothered to change it back.

Surround yourself with people who are going to support your decisions in a healthy way, whether they agree with you or not. Click To Tweet

There’s a ton of us down here. I can assure you that we’re in the vote as well. Most of us are teachers.

They were all from red states, so I imagine they have closed primaries. I think if I’m saying this right—my friend will tell me if I’m not—in Michigan, you don’t have to be registered to a specific party to vote in the primary because I’m not, but you have to vote straight ticket. You can’t split the ticket.

I don’t know what that’s called—I’ve heard of that. You guys have maybe one of those, there are certain special events. That’s not fully open, that’s for sure.

I forget what it’s called, but I remember seeing a thing at the top because when I voted in the primary last time. You invalidate your primary vote.

It’s going to confuse people that’s why they shouldn’t do that.

The Scantron form, the thing that looks like a standardized test, it does say at the top, like “you have to vote.” Hopefully, people are reading those directions.

I voted in the primary right before the pandemic, like days before we got locked down.

Ours was in August, 2020. We all had to vote with our mask on. Ours is fairly late.

Would you say now that most of your family, like your extended family, is still fairly conservative?

Yes. My dad is not, which is really interesting. My parents divorced about a year before I married my husband. What’s interesting is my mom has stayed pretty steady in her beliefs, but my dad has gotten a lot more progressive over the years. I think that’s the fact that who he’s married to now is very progressive, and that’s a natural evolution when you’re around that. That’s pretty normal.

You either grow further apart, or you change your views.

Yeah! It’s interesting. He’s not the kind of person that would just go with the flow. He usually— if he likes or does not like something, he’s not going to do something because somebody tells him to do so. I thought that was really interesting that maybe he was kind of more like me and that he went along with stuff because it was easier, then decided that it wasn’t. He’s a lot more progressive.

My husband’s parents have had a little bit of a progression, but they’re still pretty conservative, I would say. They’re not as conservative as they were.

My mom has stayed pretty consistent. She also lives in Alabama and she would be that way, anyway. I don’t think that really has an impact. If she did change her mind, she wouldn’t say, because she doesn’t like to rock the boat. That’s just how she is.

If she did change her mind, she wouldn’t tell anybody?

Probably wouldn’t tell a lot of people—that’s not her M.O. She’s not one to get online and rant or anything. That’s not her personality and she would probably keep it to herself. Maybe, she might not even tell me about it. I don’t know.

Is your relationship impacted with them because of your beliefs or do you just kind of take politics off the table? How do you navigate that?

Our relationship with my husband’s parents is pretty good, and it’s because they are so open-minded, they like asking questions. It’s never been a problem to conversate with them about stuff, even if we don’t agree, and we don’t agree on everything. We’re a lot more progressive, I would say than they are.

My mom and I get along fine and she doesn’t like to bring that into the conversation. When I do, she just rolls with it. That’s her.

That’s how my mom is too! She could talk with me and she would probably just be like, “Alright, let’s talk about something else then.”

Yep! She worries about my safety anytime I talk about going to a protest, or doing something like this, she’s like, “You’re not going to take the girls, are you?” Her thing is she wants me to be safe. I totally understand.

My dad and I, it’s never been a problem for us. We don’t have like a super tight relationship anyway, but it doesn’t affect us at all.

My mom brought something up: My parents in their early twenties when Vietnam was heavily going on in the early ‘70s. My mom and dad are almost 70 years old and she brought up something interesting about how she got caught in a Vietnam war protest during college, and how scared that made her, and how her roommate hated her because she wouldn’t take a position on the Vietnam war.

I’m like, “If this isn’t like the most new thing I’ve ever heard! You hate confrontation. You don’t like to take positions very often or talk about them and I’m not surprised that you were afraid when you got caught in a protest.” It was a really interesting insight into her psyche there, that she’s been very consistent since the ‘70s on how she operates. She hasn’t really swayed that much.

Her relationship with me is more important to her than being right, or getting a point in. She’d rather focus on having a relationship with me, which—I can respect that. I look at things with dealing with people who view it differently than I do. I try to take into account what their age is, their experience. I do take a look at that and that helps me to try to understand.

People’s experiences will often inform their beliefs and I think that’s certainly the case for my mom’s generation. So I do take that into account when I speak to her about things.

That’s such a good point. I think genuinely that’s true of most people, because you tend to see more conservative views from people who don’t encounter a lot of people who are different from them.

That is 100% right.

And you tend to see more in liberal who is from people who encounter different people. Whether that’s through travel, or living in a large city where you’re bound to have more interaction with different cultures and things like that—which has always been really interesting to me.

I know for me, definitely, I moved from a smaller rural Virginia community to smaller ones. Then, I finally moved into cities and that’s where my views started to change because I think for a while there, it was just like I didn’t really think about it, one way or the other.

I know I grew up very conservative and then I moved away. I would probably repeat very conservative things without ever really—as you said—asking questions about it, because asking questions about things is not something that comes naturally to me really. I’ve had to teach myself how to do that


And it’s been interesting. Asking questions, rocking the boat, making people uncomfortable, that is something absolutely that I’ve had to learn how to do. I think that I’m a lot better at it now than I used to be, but definitely, when I was in high school and around my family all the time, I wanted to fit in. I didn’t want to make anybody mad. I didn’t want to rock the boat. So I just never really questioned anything.

That’s a very six thing to do, so I empathize. I would have never seen, and I see you online now being confident. I would never have guessed. This is why you don’t guess and this why you don’t guess any people’s numbers. I would have never guessed you were six

People say that to me all the time!

Because you seem very confident in speaking your truth or speaking what you believe your beliefs and what your truth is. That should be an encouragement because—not that we get a bad rap as sixes—we’re not. It’s harder. At least if you’re phobic, I have a harder time rocking the boat. I really have to try.

I definitely have to work at it and I have had to create safe spaces almost, where it’s like, I run out into the world and I do vulnerable, scary things that invoke confrontation. Then I like, sprint back into my safe space with my friends who were like, “Good job. You did a good thing. Here’s a cookie.” It’s very much positive reinforcement for that.

100%. That’s exactly what happened going to the Gay Pride Parade. I did have that space where everybody was like, “I’m so glad you did that.” But then there’s always the flip side or other stuff that sometimes happens when you do things like that, good or bad.


You always are going to have to deal with it, but if you can consciously surround yourself with people who are going to support your decisions in a healthy way—whether they agree with you or not—I think that’s always a plus.


As we wrap up, if you could give advice to somebody who’s not necessarily a natural questioner, but they may not necessarily believe everything that they’re surrounded by. Do you have any advice for people like that who maybe want to branch out, but are kind of scared to step out of that comfort zone and ask questions?

For me, I would say having a person or like you said, a safe space of people, is really key. I know that’s harder today to find because of COVID and stuff; it’s harder to meet in person. But for example, online—even if you have groups of people on the internet that you can connect with, even if they’re not a spouse or whatever, that’s great.

If you can find people in whatever type of community that are supportive and encourages—not hard conversations—but just encourages people to discuss, ask questions, especially around issues where you might be in a place of privilege and you’re trying to learn and grow, that’s really key.

Normalize asking questions. Silence is more harmful than critical thinking. Click To Tweet

Just educating yourself is another way to do this. Having community, having a safe space, for me, obviously, I got really lucky. I married somebody who encourages that, but not everybody has that. There are other ways to find that besides getting married at 22—which is not advisable for all people!

If you are beyond 22, and you need help, it’s still applicable.

Please note that you don’t need to get married that young! It’s not necessary. If you are lucky enough to have a spouse or partner, great—that is amazing. It should be your go-to. But if you don’t have that, that’s okay and I know it’s hard to find in person. Having online spaces—Facebook has lots of them, Instagram, there are all sorts of different ways to find community. That’s a huge thing for me, having that.

It takes a little bit of bravery and being willing to do something wrong when you’re asking those questions. I’ll give you an example of a way that I thought I was being helpful, but it ended up not being great.

White privilege is a huge topic that comes up a lot, obviously. One of the books that I typically would recommend to people was the Robin DiAngelo book, White Fragility. I come to find out from some of my friends and people I know who are African-American that it’s been pretty heavily vetted by African-Americans and that there aren’t so many positive viewpoints on her co-opting that in certain ways. I would never have known that if I hadn’t put that out there, and asked questions. But I learned about it, and now I’m a little bit more cautious about recommending that to people.

I take the time to listen. I’m like, “I didn’t even think of it that way. Thank you so much.” Not that it is the job of somebody in a place where they’re being oppressed to educate you, but if you can learn something, even if by bypassing, you’re just learning. If they take the time to educate you, or you read something online that somebody posted that educates you, then you just take advantage of that, and learn from it, and move on.

If you don’t, I think silence and not asking questions is more harmful to you. It certainly was for me. It pushed me—I still, at my age really struggle with knowing who I am, because I was suppressing that for a very long time. I would heavily encourage you if you’re younger, to not do that, and that is not easy. It’s a lot easier to suppress and go with the flow.

For sure! Especially, if you live in a community that does not encourage asking questions or deviating from the societal norm in your area.

Your comfort zone is going to be a lot more comfortable in that way. It’s going to be easier to do that.

But if you can find people that understand, you can be willing to ask the questions. If you make a mistake or if you get caught on something or whatever, and you’re learning, just make the adjustment and keep moving forward. It’s not fun. It’s horrible sometimes. Sometimes it’s not horrible, it’s your different levels of messing up.

The one I just mentioned was kind of a little one, and there are times where you will say something that is “white nonsense” and you will get called on it, as you should. You hopefully will learn from it and not do that again.

I love the advice to basically like, put yourself in a position where you normalize asking questions, especially if you didn’t grow up with that, which I did not.

I didn’t either—it’s okay. It must be our age range or it must be just where we grew up.

I think it’s because my mom was very uncomfortable asking questions and my dad didn’t like to be questioned. So I grew up in a place where you don’t ask questions because sometimes questions can create uncomfortableness and we don’t like that. That was kind of like the mindset that I grew up in.

I honestly think though that if we just normalized asking questions and critical thinking, we would just ultimately, completely change the fabric of our society.

I agree with you there! That’s for sure.

I really appreciate you being here. This was a great conversation. I always enjoy these. I would love to do many more of them. Thank you again for being here. I will talk to you later.

Thank you so much. I appreciate it!

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About Carrie Flynn

FV 21 | Critical ThinkingCarrie Flynn is the owner of Virtual Simplicity, LLC. She specializes in helping her clients get their Kajabi sites and programs setup using our S.E.E.N method (simple, easy, efficient, not complicated) so they can maximize profits. Virtual Simplicity’s ultimate goal is to help others feel like they can breathe a bit easier and begin to enjoy their businesses and their lives again, because business doesn’t have to be complicated! Carrie is obsessed with all things systems and tech, loves her daily coffee, British TV shows and movies, and college football (Go Gators!). She’s been married to her husband for 15 years, and together they have two daughters, ages 11 and 3. Carrie lives in the Jacksonville, FL area with her family. 

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