It's been almost five years now since I cold turkey walked off my news reporter job to blog full-time. Since then, I've experienced so many highs and lows of being an entrepreneur and #girlboss. From overlooking some important business details, to learning (the hard way) to deal with shady clients, losing some of my work benefits and not thinking about financial planning for my later years; I literally had a crash course in becoming a businesswoman.
With entrepreneurship being all the rage these days, so many people only flaunt the glitz and glamour of being in business but forget to share those little nuggets of how to actually make it work. In entrepreneurship, there's a lot of personal and professional business (no pun intended) to handle that can easily be forgotten or missed.
Quitting your job to build your own empire or to bring a passion to life is indeed a risky move to make, but it's also a move that can be both beneficial and fulfilling. Just like everything else in life, you have to weigh out the pros, cons and, "Girl, you sure you wanna do this?" scenarios. Don't be one of those people who quit their job to work for themselves…but forget to build a business!
Keep these four things in mind if you're on the road to entrepreneurship.
Make the business official.
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It took me fifty-leven days for one company to run me my check and another flat out refused to book me because I didn't have a business license. Sure, I could do the work and in my head it was easy for them to just write a check out in my name. All companies are different and not everyone can just write the check; they all follow procedures and processes unique to them and sis, you don't want to get caught up in all of that. I found that it made being an entrepreneur much easier when I could supply a client with proper, legal documentation on behalf of my company. Not only does it help you to get paid easier it also proves that you take your business and coins seriously.
Benefits? What benefits?
As soon as you say, "I quit!", one of the first things that disappear are your employee benefits. As a woman, it was super important for me to have some kind of health insurance, but the minute I walked out that door, I was on my own. Some companies are great in that they allow past employees to stay in their group plans but make the payments themselves; others just drop you. I've been making the sacrifice for five years now to pay my health and life insurance out of pocket; because of the way life is set up these days, I can't chance it. If this is important to you, make sure to keep this in mind as you journey to entrepreneurship. Will you need new insurance, can you join a group one…do you even care? And then there's the pension plan. How will you save money for retirement? Will you set up your own plan? This is definitely worth the conversation and discussion.
Where’d the money go?
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I'm cheap. And I'm not afraid to admit it. As a freelance writer and TV host and occasional influencer who partners with brands, I know firsthand how fickle this industry can be. I've had partnerships taken away, given the 30-day notice and left to literally count my coins. Learning how to effectively budget and manage money is a great skill to have as an entrepreneur, in any field. All businesses, even the well-off, established ones, experience ebbs and flows in their companies and yours won't be exempt. Buffer those crazy days by saving, budgeting and investing.
It’s not an easy road.
Being my own boss is one of the greatest pleasures I've ever experienced. It's a thrilling journey of highs and lows that stretch you and strengthen you; it's simultaneously fickle and fulfilling, it has its bumpy days and days where everything is going right. More importantly, it's not for everybody. If you've decided though that you can and will do this, you have to commit to the cause and fight through the tough times.
Want more stories like this? Sign up for our newsletter here and check out the related reads below:
Passion Over Paycheck: Why I Quit My Job At 30 To Start Living
How To Cope When You Hate Your Job
These 3 Women Boldly Quit Their Jobs & Changed Careers
I Quit My Job 3 Years Ago And Built A Badass Brand With These 5 Tips
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- Ask Yourself These 4 Questions Before You Quit Something ›
- A Graceful Exit - Before You Say 'I Quit' - What's Next ›
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- How to Quit Your Job Professionally and Gracefully - The Muse ›
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- Quitting Your Job? 3 Ways to Tell Your Boss Gracefully | Robert Half ›
RELATED
Taja, an actress known most for her role on BET’s The Oval, and businessman/model Ryan Easter tied the knot on July 27 in an intimate and beautiful wedding in LA - surrounded by friends and family. During our 40+ minute conversation, the newlyweds opened up about the inner work journey they both went through individually to become their best selves.
Taja revealed that her grateful and light spirit came after being in a depressive state and doing a great deal of healing and education. And Ryan shared how losing a parent as a youth affected how he showed up in the world and the truths he had to face to embrace who he is wholly.
The pair also chatted about the power of intention, the importance of working through trauma, and the work they do every day to honor their partnership. There’s a reason their glow is so beautiful! It comes from the inside.
“You're meeting me now after I've done all this work, but I had to go through it to get to that space and be in a very happy, healed relationship,” Taja says. Check out the layered conversation below.
xoNecole: I’ll start with the most obvious question: how did you two meet, and what were your initial feelings about each other?
Ryan Easter: We connected through friends. At the time, I was in New York, and she was back and forth between LA and Atlanta. But our mutual female friends were together and decided they needed to set me up. So they confirmed I was looking for something serious and then sent me her picture.
And I was like, "Okay, she looks good - a chocolate drop." But then I thought, "What's wrong with her? So, I called them up, and one of them was messing with me and said, "Oh, she's a little crazy." I was like, "Whoa, I can't do crazy anymore. I've dealt with that before. I’d rather stay by myself than deal with that again." Then she clarified, "No, I'm just kidding. She's crazy in a good way. She's a lot of fun and has her stuff together. That’s how it started for me.
Taja Simpson: I was just going about my life, getting ready for another season of The Oval, when I got a text from my friend Natasha. She said, "Hey, I don't think you're dating anybody, but I have a friend I think you should meet. He's a great guy." She gave me this huge pedigree, saying they had been friends for 19 years. I thought, "Wow, he sounds amazing." But when she sent me a photo, I didn’t like it.
Later, I thought about it and figured it could just not be a good picture. So she sent his Instagram which had all these modeling fitness pictures and stuff. And then I was like, wow - you had my whole husband this time and didn’t tell me - now I told her she could give him my number.
"I was just going about my life, getting ready for another season of The Oval, when I got a text from my friend Natasha. She said, "Hey, I don't think you're dating anybody, but I have a friend I think you should meet. He's a great guy." She gave me this huge pedigree, saying they had been friends for 19 years. I thought, "Wow, he sounds amazing." But when she sent me a photo, I didn’t like it."
Taja Simpson & Ryan Easter
Photo by @jorgemezaphotos
xoN: I love that because, you know, there's all these conversations about the ways people meet, and I still feel like friends and family are one of the best ways. It’s like they know you! What are your thoughts?
Ryan: Yeah, absolutely! You feel a great sense of obligation to be the best version of yourself because you’re not just representing yourself; you’re also representing the person who referred you. I can’t go out there acting like a fool and have them looking at their friend like, "Why did you hook me up with this clown?" It’s like, we're gonna be clear and honest about our intentions. And if it works, great, and if it doesn't, it's okay.
Taja: Exactly. When he called, we spoke that day for like, an hour. The rest was history. We just connected, and it was great. After that, we started talking every day, and now here we are.
xoN: Okay, so tell me about your first date! Do you remember where you went? What did you do? How was the vibe?
Taja: Our first in-person date was two months after we met over the phone. This was during COVID, so we got introduced in July 2020 but didn’t meet until September. From July to September, we were doing video dates and phone calls, building up this excitement about meeting in person. I was really nervous. I thought, "Oh my God, is it going to be like it was over the phone?" We really connected and vibed. I was there to pick him up at LAX, and I felt like this was it. I thought, "God put this brother in my life to be this good, this perfect." It felt too good to be true.
I actually had a friend meet us at the airport to film our meeting without him knowing. I told her to stay in the corner and keep the camera hidden. When he was coming down the escalator, I had this whole plan to run up to him in slow motion and jump into his arms. When I saw him, I froze. I was so nervous that I couldn’t move! He came up to me, gave me a big hug, and swung me around, and I just thought, "Wow!" Everything I planned went out the window.
Ryan: I was really excited to meet her, too. Technically, our first date was at Firestone Brewery. After the airport, we went back to her place to drop off my stuff, and then she said, "I like to drink beer," so she took me to a brewery nearby.
I remember being there, and we were kind of embracing, but not too much since it was technically the first time we were in physical proximity. You still have to play it cool, even after talking for a while. But every time I touched her, it felt good. I thought, "Yeah, this is it." When we hugged at the airport, I felt like, "Yo, this is home." At that moment, I knew she was the one.
xoN: Ugh, I love that. So when did the courtship start to develop into a relationship? Did y'all have that conversation?
Ryan: Initially, we were very clear about our intentions. We were both dating with purpose and had similar aspirations of eventually finding someone to marry, start a family, create businesses together, and live our lives to the fullest. We knew from the beginning that this was our goal and checked in with each other to see if we were on the same page.
After establishing our intentions, it was about having those small conversations. We discussed what was important to each of us—our needs, wants, likes, dislikes, triggers, and traumas. All those details are crucial for building a solid foundation for a healthy relationship. We spent a lot of time getting to know the real person, not just the representative we might present to the world.
Sometimes, it’s difficult because it requires us to be extremely vulnerable. For men, especially in our society, vulnerability is often frowned upon, making it hard to expose that sensitive side. You never know how people will react—some might use it against you, while others might protect you.
I think for her; it took her understanding that mentality that men have and use that to her advantage to make sure she's like, look, this is a safe space for you to allow me to see the full person that you are. I appreciated that because, like, I would tell her, if you really want a man to value you, he has to feel safe with you, right, not necessarily in a physical capacity but more so from an emotional standpoint; I need to feel like I can be safe with you emotionally.
So that courtship was a lot of just having those serious, sometimes difficult conversations about things we're going through in the past to things we aspire to accomplish in the future, to things that we're currently dealing with, and started to gain that understanding about who we are and what we aspire to be, and just continue to flow.
"So that courtship was a lot of just having those serious, sometimes difficult conversations about things we're going through in the past to things we aspire to accomplish in the future, to things that we're currently dealing with, and started to gain that understanding about who we are and what we aspire to be, and just continue to flow."
Taja: I mean, that's exactly right, and a lot of it we spoke about even before we met. Because it was this free thing where we didn’t know each other. We didn't have to be a representative. I was just my authentic self. It’s like - I'm an actor, and I got five or six characters that may come out in our conversation. I'll be funny, then the next moment, I'll be serious. It just happens.
I was very vocal about how I foresee my life going. Also, because I'm in entertainment, that played a part. I had met people before who couldn't handle that. They wanted a woman with a nine-to-five, a teacher, or just somebody with a very strict schedule. But that wasn't me. So I think we were super intentional when it came to dating and making sure we can build and grow together. So, we made that commitment prior to him leaving. He came to LA for a week, and the day before he left, it was like, okay, so this is it.
xoN: I’ve noticed that intention and vulnerability are both powerful words that you two keep using, which I think is essential for any long-term relationship. What are some of your other shared values?
Ryan: Also, we both understood the power of mindset. When you see successful or unsuccessful people, sometimes others will attribute their state to their family or money. And I'm not saying that that doesn't help. But there are a lot of people who have come from very humble beginnings and very troubled past that have gone on to do great things, and it all had to do with their mindset. They had to leave and see themselves doing what they desired to do before it became a reality in the physical realm.
I think a lot of those beliefs and mentalities that we shared was refreshing because, you know, we've all known people that every time you talk to them, something bad is going on. And it's such a drag because they can bring your energy down. We don't subscribe to that. Not saying that we don't go through tough times. But when we do, the question that we always ask ourselves is, what is it that I'm supposed to learn from this? I think those type of elements of just being in alignment mentally about how we view the world definitely help to solidify our relationship and our connection.
Taja: When we met, I was in a headspace of growth. We now call it believe, evolve, become because you have to believe that thing right in order to show up. We both understand that your vibration precedes your manifestation, so you have to vibrate and believe at a certain level. Act as if you have to be in that space, that energy, in order for that thing to come so you can evolve and then become whatever that said thing is. But I was in that headspace before we met, and I was clearing out people in my life.
I was really intentional with finding someone that was in that headspace, too. I was not okay with anyone being stagnant.
Taja Simpson & Ryan Easter
Photo by @jorgemezaphotos
xoN: You two seem so evolved individually and collectively. I'm curious, were there any challenges that you two had to get through together, and what did you learn from that experience?
Ryan: Being parents. And if your partner doesn't have a great pregnancy, then it can be tough, and it stretches you in a lot of ways. But I would definitely say the first five months of being new parents was a lot because we were both exhausted. And she's also trying to heal her body because giving birth puts a tremendous amount of stress on the woman's body. It gives you a different respect for the strength of femininity because I wouldn't want to go through that. And I was there the whole 29 hours.
So during that time I'm getting snappy because I need to rest. I have not been able to rest, and I'm sleep-deprived, and I don't feel like I got my foot in yet. And, and then, on top of that, you have this, this really small human that's completely dependent upon you. They can't do anything for himself, and that, even psychologically, that's a lot to carry. But the thing that I think that has helped us is that we understand that we won't always be on the same page. It's okay to have disagreements, but you always have to lead with love, meaning that if I'm upset with her or she's upset with me, we focus on what the issue is.
Taja: I had a horrible pregnancy and was still feeling like I want to be productive; it’s just part of who I am. And during the newborn phase, like he said, we were exhausted. We were zombies. I'm getting whiny. I need sleep. He's getting snappy and short, and we're having to figure out us. The hardest thing is trying to still learn how to effectively communicate in the midst of this space where you are exhausted; you don't feel good, nothing's going your way.
But I'm a big believer of being accountable, especially for women, because women are not always accountable. But we encourage each other to address the trauma and encourage positive self-thought and talk. Because what you think, speak, and do creates power for better and worse.
xoN: Were there any past traumas you had to heal from in order to love each other correctly, and do you feel comfortable discussing them?
Ryan: For me, the biggest thing was my father’s death at nine. You’re young, and you don’t know how to process the loss. It’s one of those things I thought I dealt with, but when I got into my adult years, I realized it didn’t. I always felt like I had to go above and beyond because I didn’t have my father there to be a man - I excelled in sports and academics, but it was based on an inadequate feeling.
I understand the importance of fathers in children’s life but you still have the power to be the best version of yourself whether your father is there or not. And I believe the almighty Creator will put people in your life to be the best version of yourself. I wanted to be that confident person for her and our children - and I didn’t want to carry that trauma into our relationship or our son. So I worked on it before us and I continue to now.
Taja: Mine was colorism. I grew up where the brown paper bag thing was a thing. There were kids I couldn’t play with because “I was too Black.” I had a family member who called me “Ew.” Like she’d literally say, come here, Ew, you ugly thing. And my family, for a long time, didn’t realize how it was breaking me. But eventually, my mom noticed and taught me more about self-esteem and then I started to do the work. But it still shows its head. I still would have thoughts that I’m not good enough because of how I look. I’ve literally not tried out for roles because of that. One of my friends’ friends has literally called out once that I was the only dark person at an event.
So when I started doing the work, I noticed the ways it showed up, like I just wouldn’t want to be in the sun long. I mean when I was younger, I used to pray to God to make me “better” or lighter. It took a long time to really get over that. There’s a book I wrote called Women Who Shine - where I got my thoughts out about this.
So he knows my sensitive spots and speaks to the little girl in me. It's so interesting how the things we go through when we’re young affect us in adulthood. Mental health is as important as physical health - and I’m grateful that he understands the importance of both of those.
xoN: Thank you for your vulnerability. I hope it helps someone else. Finally, I’ll close with this: what’s your favorite thing about each other?
Ryan: Definitely her mindset. She doesn’t have a victim mindset; she’s empowered. That’s so attractive. I believe that she prides herself on being a good, great communicator. She moves with integrity, you know, I think that's important. And you know, she also understands the importance of taking care of her physical, emotional, and mental wellbeing.
Taja: There’s so many. Where do I start? My husband is supremely supportive. I absolutely love that about him. Also, I love his intention. I love how effectively he communicates. I love how he fathers our child. I love how he looks. Because, praise God. Okay, I'm just gonna put that out there.
But you know what, my favorite thing about him is that I love that he's a man of integrity.
Integrity was the highest things on my list when I’d write out what I wanted in a partner. Because it’s everything. And so I love that I feel the level of safety that I feel with him, that I can completely be my 100% authentic self. I know that he's taking care of me, my heart, and our family. We're good.
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Feature image by @jorgemezaphotos
Cynthia, her husband, and their now-4-year-old boys are part of the growing number of families who are traveling and taking their small kids along for the ride to explore the world.
She, along with mom, law student, and travel content creator Kenniqua Mon’a, shared with xoNecole tips from their experiences venturing thousands of miles with their tots, racking up passport stamps, and enjoying U.S. adventures. They’re changing the narrative on how to travel with kids and sharing tips on navigating everything from temper tantrums thousands of feet in the air to sneaking in some solo time on that next vacation.
On Reasons To Travel With Children While They're Young
Courtesy of Cynthia “SimplyCyn” Andrews
Cynthia: "Like everything in life, you share with your children the things you naturally love, whether it's food, music, or a hobby. There are things that make you who you are, and [for my husband I] travel has always been a part of who we were. [As parents] we naturally kept doing the things we love, and it only made sense to bring the kids."
Kenniqua: "I didn’t get on my first flight until college. That’s one thing I regret and I knew I didn’t want that for my daughter, Ryan, and that’s why she was on her first flight at three months old."
Akin to parenting, there’s no one-size-fits-all manual for traveling with your little ones. But, with these four tips, you’ll make it from Point A to Point B in one piece-sanity as guaranteed as your checked luggage.
On Embracing Spontaneity
Cynthia: "You make sure [kids] get up and go to sleep at the same time and eat meals at a certain time. What gets lost in that is spontaneity, you lose the sense of adventure and the ability to dream and imagine differently. While traveling in Croatia, we started to take the kids back to the hotel for their nap, but instead, we just put the boys into their strollers and just let them nap while we got to sit, people-watch, and have conversations with other adults."
On The Concern The "Too Young To Remember" Myth
Courtesy of Kenniqua Mon'a
Kenniqua: "I take a million photos and videos, so eventually, my daughter will see all these amazing places she has visited. She’ll see herself in different states and countries- when she was running around at two years old and then at 20. Being able to compare those experiences is something I look forward to."
On Making Time For Solo Enjoyment
Cynthia: "I’ll do an activity solo for a few hours in the morning while Dad takes the kids, and then he’ll do something solo for a few hours while I take the kids, and then we all do something together. We both get to explore with the kids and as a family, but it gives us each a solo moment to breathe and do things we enjoy on our own."
On Making The Most Of Down Time
Kenniqua: "I plan as much as possible to make sure my daughter is not only occupied, but we’re also having fun as a family, even during long-haul flights and road trips. We play games so traveling time can be interactive and we are actually communicating and spending time with her during those moments. So your kid doesn’t just feel like, 'Oh, I'm just sitting here, and I'm bored.'"
On Lessons Learned From Traveling With Children
Courtesy of Cynthia “SimplyCyn” Andrew
Kenniqua: "A lot of times, young kids will get agitated or irritated because they can’t communicate those things or don’t know how, and they [have a tantrum.] As a parent, you can’t worry about what everyone else is thinking or saying. All you can do is control what you can and comfort your child in those moments."
Cynthia: "My son [is autistic], and it's almost like he's this really tight rubber band sometimes, but every time we travel, it kind of stretches him out a little bit, and he becomes a little more open to trying new things—more open to being around different people. We’re seeing this growth in him through travel, so that’s an additional benefit."
To all parents eager to travel with their children, Cynthia offered a bit of advice. "Don’t stress about getting there. Just remember you’re going to have the best time when you get to your destination."
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