Homecoming to Yourself: Interview with Coach, Writer, and Creative Charlotte Jackson
Charlotte Jackson is a writer, transition and creative coach, and the cofounder of community and connection centered projects such as Reading Rhythms and CANDID.
Charlotte graduated from college in 2020 during the midst of covid and, like many new college grads, found herself navigating the uncertainty of living at home and spending months searching to land a remote job. She experienced feelings that anyone who has experienced the trials and tribulations of their 20s can relate to — she felt stuck and unsure of how to create a life and career that felt fulfilling. Charlotte took a chance in 2022 and pushed the edge of her comfort zone by moving to New York City. Though she’s naturally an introvert, she committed to a season of saying yes in search of finding community and connection. In doing so, she found a tribe of friends who were just as passionate about creating a life off the beaten path as she was. That community and regaining a desire to pursue creative projects for no other motive than her own curiosity led to a transformational series of creative projects:
Her blog Caught up in Char’s Web
The reading community she cofounded with three friends called Reading Rhythms (which has been featured on the TODAY show and expanded to cities across the US and the world)
CANDID, a deck of playing cards that act as conversation starters, developed with her boyfriend John Lifrieri
I wanted to speak with Charlotte because I think her story and message serves as a powerful reminder that feeling stuck doesn’t have to last forever and that the path forward can simply start with being brave enough to say yes.
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
How would you describe what you do for work and what you're currently up to in life?
Well, first I just love how different "how do you describe what you do for work?" is from "what do you do for work?" because they are very different questions, and it gets you thinking about it in a different way.
I recently listened to a podcast with Elizabeth Gilbert, where she was talking about differentiating between hobbies, a job, a career, and your calling. She loosely defines them as:
Hobbies being things that you do out of pure passion, interest, and enjoyment.
A job is something that you do to make money. You don't necessarily have to love what you do, but it’s something that you do in order to pay the bills and survive.
A career is when your hobbies and job intersect, and you are able to devote yourself fully to passion driven work because you have the ability to make money from it. Not everybody has to have one, and it's okay to not have that intersection.
A calling is something that you either have or you don't have. Again, it’s okay not to have one. If you don't have one now, it may come later. But if you do have one, it becomes something that eats away at you unless you are devoting yourself to it.
I think I'm in a season of life where I have something for all four categories. Right now I would say that my hobby is food video content creation. I started posting recently on my Instagram, which has been really fun. My job is working for a financial publication firm doing project management. My career is coaching and entrepreneurship, and my calling has always been and probably will continue to be writing.
We reconnected in 2023, and I was really taken aback by the journey that you've been on over the past two and a half years, which has been filled with transformational life and professional changes. I’d love to hear you talk about that journey in your words.
It's been by far the most transformational two and a half years of my life. I'll start with when I moved to New York, which was in 2022. I was fresh off of a breakup and a kind of "Eat, Pray, Love" solo trip through Europe, and was feeling famished for connection and novelty.
I graduated college in 2020, during the middle of the pandemic, and accidentally and unexpectedly ended up living back home in California for a couple of years. It took me a year to find a remote job. Then I found my way into this relationship, moved across the country, and lived in a senior living home in Dallas where my then boyfriend was working at the time. When that relationship ended in 2022, the world was also simultaneously coming back online for the first time in a way that was actually meaningful. At that point, I found myself in New York and just threw myself into meeting new people and trying to find fulfillment outside of work. It was a chain reaction of meeting the right person at the right time that led to another person and another person and another person. After a little while, I found myself immersed in a community for the first time where I felt like I was surrounded by people who were equally as amped up about living off the beaten path as I was.
I think I always knew that I wanted to lead a more entrepreneurial lifestyle, but I was also so good at checking all of the boxes. I had to get comfortable with embracing the idea that I could just start doing things without anybody asking me to. That was really the thing that led me to start a reading community with the friends that I had made, and then we turned it into an event series. One thing led to another and I started to take my creative projects a lot more seriously. Those things and writing my blog ended up giving me more creative confidence than I ever could have imagined.
I want to talk about a few of those projects because there is a tremendous amount to highlight. Reading Rhythms completely took off, was featured on the Today Show, and has grown to cities outside of New York within the US and internationally. You launched your conversation cards project, CANDID, at the end of last year. You also recently launched your own coaching business and have now written over 70 pieces for your blog. What mental shifts and tools do you think were most impactful in giving yourself the space to explore those projects?
I remember when I was moving to New York, I looked back on my vision board and there were a few things that stood out to me. Two of them were what I called "the lemonade stand feeling,” and then I had this picture of people working together burning the midnight oil.
The lemonade stand feeling was about reminding myself of what it felt like as a kid to have the plan to host a lemonade stand on a weekend with a friend. We’d have to convince our parents to take us to Costco to get supplies, set up the tables, and make the signs. There was something about the collaboration with my friends and working on a group project together outside school that I was so jazzed by.
The teammates burning the midnight oil picture quite literally looks like Reading Rhythms. It's five people on the ground reading and working on something. I posted it on June 13th of 2022, and then one year later to that day is when we started Reading Rhythms. The mental shift that was taking place was my desire to reignite the childlike joy that I got from building projects with other people just for the shit of it.
Everything we’re talking about is happening in your early to mid twenties. I remember those years of my life being difficult in a way that I was completely unprepared for. You graduate college thinking the world is supposed to be your oyster, but getting your first job and being out of that school environment can be very isolating and lonely. I definitely remember having the thought a few years into my first job of, "Oh my God, is this going to be my life forever? Is this it?" It can feel so existential and paralyzing to know that you don’t love your current life or career, but feel like you have no idea how to begin changing it. Given the journey that you've been on, what advice would you have for that twenty something person who is feeling stuck but unsure of where to start working toward a change?
I relate to that intensely and remember feeling very disoriented. In hindsight, the thing that helped the most was starting to reconnect with some of the simple things that I enjoyed doing before I became a thoroughbred horse at jumping through the hoops that other people set out for me.
The lemonade stand feeling was part of that, but it was also about asking myself questions like: What did you do as a kid that other people thought was kind of weird or extra that you loved? What's something that you want to do that you fear other people might think would be a little bit cringe or try-hard, but you would enjoy it? From there, it became about finding other people that enjoy doing the same things, or building the courage for me to lean into those things.
Another big part of it came from maybe the best advice I've ever gotten, which was from my college thesis advisor. I remember going into her office so stressed out trying to figure out how to write this 100-page thesis. I was also very perceptive to who she was and what she was doing—I knew she was probably in her late thirties or early forties, had two young children, was married, had this professor job, worked at a nonprofit, and exercised regularly. I was thinking to myself, "How the hell does this woman have enough time in the day?"
All of a sudden I was stressed, thinking that I needed to start doing her routines now so that by the time I was in that stage of life I'd be prepared for it. She could hear this in my voice, and she stopped me and said, "Char, stop trying to prepare for the circumstances that you think you're going to be living in and start meeting the unmet needs that you have now as a 21-year-old."
That was so powerful. I would say that to somebody in their early-to-mid twenties too: stop trying, don't get too ahead of yourself, and start really close in. Start close in comes from a poem of the same name by David Whyte that I love which is about taking that scary first step. I would say do something that excites you, and if you're not sure where to start, I think the best way to remember is to go back to what lit you up as a kid and try to make a new friend that you have to explain yourself to. In resurfacing some of your favorite movies or your hobbies or sources of inspiration, things come back online, and presenting them to a new person is part of that. Similar to what I mentioned before we started - preparing for this interview brought thoughts to the surface that might not have emerged had I not been preparing for it. Same with making a new friend: when somebody that doesn't know you asks you "who are you?" I think it can help you reconnect with parts of yourself that might not have resurfaced otherwise.
I have to ask about the friend-making bit. At least from the outside looking in, you are very good at making friends and creating community in a way that I'm in awe of. I think that's something that a lot of people really struggle with, but is an important aspect of walking an unconventional path - having those other people that get what you're going through and can give you those nudges forward or points of validation. What was it about your return to New York and the approach you took that lent itself to finding those people?
It's funny to hear you say that you think I'm good at building community and finding friends. While I'll own that now and think I've gotten a lot better at it over time, I can honestly say I have not always been good at it. I actually think that's been the thing that's allowed me to find the most alignment in my friendships at this stage of life.
In high school, I felt like I was always straddling different friend groups but never fully fitting in, and I honestly pretty much hated college for this very reason—I never found my fit. So I think what was so liberating about moving to New York was that there were so many different types of people, and I also think it was just the perfect moment in time.
I am by nature a creature of habit and actually pretty introverted in the sense that I recharge alone, and I'm very selective about what I say yes and show up to. But this was a time where I said, "Okay, I'm going to hold that. I'm not going to put myself in danger, but I'm going to intentionally step to the other side of my comfort zone and start going to things that I would usually say no to because I really do want to meet new people.”
I remember there was one time where a loose friend from college invited me to a rooftop party. I went to that party and recognized this girl that I had seen 15 years ago on the beach one time. She invited me to her housewarming, and I met another person that said I reminded him of his friend, and then this friend introduced me to my now boyfriend and all of my best friends. It was a chain reaction of putting myself in situations where I would be exposed with greater likelihood of meeting more like-minded people. The key is actually going to events and finding things that are somewhat interesting to you. Even on days where you're like "I would really love to just sit at home and watch some YouTube vlogs," pushing yourself a little bit outside of your comfort zone and actually showing up.
I can relate to so much of what you're saying. I am such an introvert and was always someone that felt like I had lots of 1:1 friendships but didn’t really have that sense of community. The thing that’s so liberating about what you're saying is that the shift can be as scary, but also as simple as, being open to it and making that choice.
A hundred percent. When I think back to those times, it really was just a matter of one conversation. You build so much momentum when you put yourself in those environments. Also, once you find one person where you think, "Whoa, how do you exist?" they tend to know more people like them, and it's easier to magnetize those types of friends to you.
It actually makes me think—my now boyfriend John introduced me to a lot of people. We were also friends for a whole year before we started dating. One time he introduced me to a friend, I went on a walk with this friend, and we spoke for four or five hours. One of the things that we did together is actually talk about the question, "What is it about John that made us click so quickly?" So we actually wrote this document called "The Friend Qualities of John Lifrieri," in which we wrote out, "Okay, who am I? Who are you? Who is John? And what do we all have in common that just made this feel so fulfilling, so quickly?"
I want to go back to an undertone of this conversation, which is the way you seem to have leaned into a season of being comfortable in your own skin and making decisions based on "what is it that I want," versus succumbing to the pressure of society, what's cool, or what you think you should do. What do you think are some of the biggest shifts that have allowed you to lean into finding that comfort and having that be a source of decision-making?
I think the biggest thing that allowed me to feel more comfortable in my own skin was getting over the fear of scraping my own knees. As somebody that grew up constantly being told that I was really mature for my age and called an old soul, I think I developed a fear of making mistakes. I learned that I could evade making the same mistakes as people that were a bit older than me by learning from what they'd done. I thought, “I'll just take all of their lessons and I'll never have to go through it myself.” Over time I’ve realized that probably led to an exacerbation of my imposter syndrome and also a fear of getting things wrong, fucking up, trying things, and seeing what would happen on the other side.
I think the biggest thing that actually allowed me to feel a lot more confident in making my own decisions is knowing that even if I know someone who has done something that I want to do and been burned by it, I can still try it. I can still do the thing and see what happens for me on the other side, because you tend to learn a lot of lessons along the way that you don't have the foresight to be able to see. So that's been the biggest shift—allowing myself to get a little scraped up.
How has your relationship with fear and self doubt changed over the past few years?
I think this one's still a constant work in progress, but I do think I have gotten a lot better at trusting myself and iterating more quickly. I think that part of this "old soul, mature for your age" persona built the tendency to over-research everything. My knee-jerk reaction in wanting to try something new is, "Okay, well, I need to spend two years learning about this." For instance, with becoming a coach, my first thought was, "I need to go have a mentorship or apprenticeship for 15 years before I have anything worth my salt to say." My boyfriend John was like, "Well, or you could reach out to a distant family friend and see if they'd be interested in doing your coaching program and see if you even like being a coach." That has helped me a lot to get over the fear and uncertainty by saying, "Okay, what is the first step that I could take to try this thing and see if I really like it?" and kind of beta test if the decision that I want to make is the right one.
Sometimes I'll even emotionally try it on a little bit before too. Let's say I want to shift in the direction of making more content online—what does that feel like in my body to go through? What parts do I find emerge over time? Kind of working through that actively and doing a lot of self-experimentation has made me a lot more comfortable.
On that last note of seeing what parts come up—that's a reference to Internal Family Systems. I've started IFS therapy myself, which has been hugely transformational in helping me to feel my emotions and actually complete the cycle in my body, as opposed to just intellectualizing them all and narrating through my experience, which I am really good at, but have found is actually not very helpful.
I want to hit on some pieces from your blog because I love your writing. I really enjoyed the piece about your aunt and uncle relocating to the south of France in their 70s. I think it really hit home the point that it is never too late to go do something unconventional or try something you’ve always wanted to do. One thing that's really interesting about fears like something being “too risky” or “too late” is that they seem to plague young people just as much as older people, if not more so. What do you think is necessary to give yourself that permission to reinvent and overcome the fears associated with starting over?
It's always "too something." I think you see that at every stage of life. So then you take a step back and have the ability to say, "Okay, well, if I'm always too something, maybe there's another way of looking at this."
I listened to a Jay Shetty podcast a little while ago, and he was talking about how somebody asked him, "Okay, you went off and became a monk, and then came back, and now you're married and a celebrity. How do you navigate being constantly misunderstood for who you are?" His answer to that was: no matter what you do in life, you're always going to be misunderstood. So you can either be misunderstood for doing the things that you want to do, or you can be misunderstood for doing the thing that you think somebody else wants you to do in order to be understood. But no matter how you skin it, you're going to be misunderstood. So you might as well just do what you want.
I think that applies to the "too risky, too early, too late" fears. You're always going to be too something, and you can look for evidence to show your fears that they're probably true. You could look for somebody that started a podcast, and it tanked and say, "See, I shouldn't do that." Or you can look for someone that has, like Kit and Peter, completely started a new chapter of their life in their seventies, and have lived such a fulfilling chapter because of that courage to reinvent. I think leaning in and optimizing for that freedom is the thing that you have to do in order to give yourself the permission to just rip it.
The other fear that lurks around everything we’re talking about is, "I don't know how it's going to work out." I think a lot of people can relate to being over-planners and over-researchers in pursuit of wanting to know how something will play out before they begin. What are the biggest changes you've noticed in how you relate to uncertainty, and what helped you create that shift in being able to embrace it?
I think this one is still a work in progress as well, but it does go back to that quick iteration piece. Now, since I've allowed myself to take little risks, and then bigger risks and bigger risks and bigger risks, I've seen the snowball effect of how those choices played out over time. If I look back on anything positive that has happened in my life, it has been by random circumstance. Even the way that I met all of the people in my life that I hold closest now—it was really just by having the tiny bit of courage to say, "Sure, I'll go to this random rooftop party," or the job that I have now came from me messaging my boss on LinkedIn. Even moving to New York in general — I had no idea how it was going to go.
I’ve learned that you have to take the jump usually before you feel fully ready to. What gets me excited and gives me momentum to continue doing that is knowing that even right now, in this moment, I am so in the middle of a story that I have no idea how it will unfold. I think that if you can transmute the fear into curiosity, it allows you to approach it with this open-minded excitement as opposed to dread.
It reminds me of another Elizabeth Gilbert exercise I was listening to—a book launch sort of thing that she was doing with this other author, Suleika Jaouad. They were announcing Suleika’s new book, The Book of Alchemy, and had the audience do this exercise with them via a live Zoom. During the exercise, you sat down, closed your eyes, asked fear to come through the door and sit next to you, and then wrote out all of the things that you were afraid of. Basically following the framework, "I'm afraid that…, I'm afraid that…, I'm afraid that..."
Suleika shared her fears in front of the audience, and they had everybody react live with hearts anytime one of her fears resonated or was something that you wrote down. The whole Zoom was just flooding with hearts, which is just to say that everybody has the same fears. Then they had us do another exercise where we closed our eyes and asked curiosity to walk through the door, and we wrote, "Dear Curiosity, what would you have me know today?" And then you wrote out your answers using the line, "I am curious about…, I am curious about…, I am curious about..." You saw that your fears and your curiosities tend to revolve around similar themes, but the feeling in your body when you approach it from fear versus curiosity is a complete 180. I think the thing that has allowed me to stand more firmly in my approach to uncertainty is being a little bit more curious.
You recently wrote another piece on your blog entitled, “how to ask better questions” where you wrote about how the types of questions we ask ourselves impact our awareness and experience. You contend that we can ask questions that empower us or, alternatively, diminish us. I wanted to ask you: What questions have had the most significant impact on your life?
One of the first ones that came to mind marked a turning point in my life, which was in the first conversation I ever had with my boyfriend John. We were chit-chatting, and instead of asking me, "What do you do for work?" he said, "What's the dream?"
I was taken aback. I didn't really know how to answer the question, so I just rolled out my cookie-cutter answer. I don't even remember what I said. It was probably some kind of contrived elevator pitch that I had crafted so that I could answer the question and move on quickly. So I answered it, and then I lobbed it back to him. I said, "What's the dream for you?"
His answer was something to the effect of: In his life up to that point, I think he was 26 at the time, he had worked on really cool projects with really cool people, all of which came about from the unfolding of the path that we've talked about, which was random event leads to random event leads to random event, with the right person, right time chain reaction. He said, "If all of the success in my life has come from that so far, the dream is just to continue being in the right place at the right time and getting to work with people that I really admire from a standpoint of joy and gratitude." My jaw dropped. I was like, "Are you kidding me? You're allowed to answer that question that way?" It was so disarming and so exciting. I realized I didn’t need the elevator pitch anymore. So I always love that question: "What's the dream?"
One that I've been thinking a lot about more recently is: "What happens when you share yourself vulnerably online?" It’s been something I’ve been thinking about as I start to post a little bit more on social media — from the standpoint of trying to reach more of the people that I want to reach, on platforms that I feel kind of allergic to but recognize are the tools of the time. I do think that posting vulnerably online has been a key to a lot of what we've been talking about —unlocking your creative confidence.
Lastly, one of the first questions that John and I asked together was: "Who in your life has a romantic relationship that you'd want to emulate, and why?" It's a good one because it's really hard to answer. I think we asked that to each other when we were friends, and it was through the contemplation of that question that it eventually allowed me to come full circle and see, "Oh, well, maybe we’re not just friends and maybe you should be my boyfriend."
I’ll finish up with two more questions. The first is: How are you intentionally crafting your life inside and outside of work? Put another way: what’s your “no directions” path look like today? I’ll add some context on what inspired this question. I think a lot of people assume that I want to know all the crazy shit that you're doing, and I do, but it's more about how people are intentionally choosing whatever it is they want their life to look like. I’m very interested in what it means to intentionally choose.
I think this will be a fun question to reflect back on in a couple of years, because I feel like I'm in the midst of a transition right now. Right now I'm starting to pursue coaching as a career, which feels really exciting. I'm working with a few clients and looking into which programs I want to do and getting this feeling of, "Oh, this actually makes so much sense. I'm pretty sure my newsletter has been a coaching blog for the past couple of years." I didn't really know it so it has felt really good to pour more into that and then simultaneously continue to write. That's the thing that always fills my cup.
Allowing myself to dabble with different platforms has also been interesting. I've always been on a social media hiatus, typically don't have social media on my phone, and generally have felt very resistant to it because it’s so addicting. But I have gotten to a point where I have been trying to use it more as a tool for self-expression and getting over any of these remnant fears of showing myself. From that standpoint, I've learned that I have a lot of fun editing and making videos.
My boyfriend John and I moved in with one of my best friends, Allie, so it feels like we're in this friends chapter of life where we all work from home, and though it will likely be a short season, it feels like a very special one. My friend Allie has always said that if she were to come into money, the first thing she would do is hire a private chef so I said, "Perfect. I will take it upon myself to become your private chef for the summer." I started this content series around cooking for her and John, and one of the videos now has over a million views. I got 10,000 new Instagram followers in a week, and it was an interesting moment to pause and go, "Okay, this is my hobby and I want it to stay in my hobby box.” Still it was fun to start to see what the downstream effects of sharing this type of content with the world could be.
So I guess to answer the question of what my "no directions" path looks like today, I honestly don't know. I'm doing a lot of different things and seeing how the hobby, career, job, and calling pieces are all going to come together. But I definitely am in the midst of a season where I could see things settling in a lot of different ways so I'm just spending a lot of time creating right now. To decompress from that, I've gotten into camping and backpacking trips.
Normally, I end with asking "what's next for you" but that doesn't feel like the right question because you're in this exploration period. Instead, I want to ask: What would you title this chapter of your life?
I have two titles. One of them is more serious, and one of them is more fun.
The first one is the word "homecoming." After a few years with lots of dabbling, I think I've gotten a lot more clarity around who I am and who I'm not. I feel a lot more comfortable in who I'm not being okay and not needing to try to be this mega generalist for my whole life. There is a feeling of homecoming and relaxation in allowing myself to say, "Hi! I'm Charlotte, and these are the things that I'm good at and love, and these are the things that I'm not that great at, and that's okay."
But the more fun title relates to one of my favorite movies which is Julie and Julia—the movie about Julia Child. I had this moment, probably eight years ago, where I was on a flight in New Zealand, while I was studying abroad and going from place to place, and I watched that movie. I had this full body chill feeling that I don't know how to fully describe. It was just like, "Something about this is a piece of the puzzle for you." So whether it's taking somebody's cookbook and writing a blog off of it, using that format for something else, or doing something with cooking and food and gathering—it feels like that is a clue as to what this next chapter will be. So maybe the title is "finding my Julie and Julia," or something like that.
It was such an honor to do this interview with you. Thank you for the time, love, and thoughtfulness you poured into this. I am so grateful to have had the chance to reflect and share my story in this way xx