20 Journal Prompts For Entrepreneurs To Reflect, Learn, And Thrive
Many have touted the benefits of journaling, especially when it comes to one's mental health. I've always been one to keep a diary, but in recent years, journaling has become quite challenging for me. Nowadays, I feel like my thoughts are moving way faster than my hands can write, which frustrates me to the point of not even bothering to write them down. (And I'm not a fan of putting my personal business online or on my phone via an app. I'm one of those people who fears that there's always somebody who either has access or can gain access and the possibility is just too creepy and scary for me to even attempt to use any digital form of a journal—cybersecurity be damned.)
One day, I was trying to think of ways to recommit to journaling, especially since I've been through quite a few career and life transitions (Weight loss and master's degree, anyone?), and came across the concept of journal prompts.
They're basically targeted, open-ended questions that lead to a more structured way of writing down your thoughts. The premise reminds me of the training I've recently completed for my master's studies, where coaches are able to guide their clients toward successful outcomes versus just telling them what to do.
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Journal prompts have offered me a method of self-exploration, reflection, and focus that takes a bit of the overwhelming annoyance out of trying to obsessively control the process of journaling (which, for me, is a self-defeating and counter-productive habit). I feel more at peace answering such questions and I'm less apt to rush through the journaling process, something that is supposed to add peace to my day, not lump-in-the-throat loathing.
Here are a few favorites I've turned to as a self-employed, type-A Capricorn who always has 50 million things going on, is constantly in her head, and needs brain-dump release with a side of return-on-my-time-investment:
- What personal milestones did you reach last week related to your business or work?
- What was your “a-ha moment” this week? (If there wasn't one, explain why).
- Who is your ideal client? Why?
- What motivates you to continue doing what you do?
- What does a great work-life balance look like for you?
- What business win did you experience this week? (And how did it make you feel?)
- How did you feel after taking meetings today? Which one was your favorite? Which was your least favorite? Why?
- Who is one business leader you admire? Why?
- Who is someone who you consider your competition and what are three things you admire about them?
- Where do you see yourself revenue- or earnings-wise in 30 days?
- What actions are you taking today to reach a revenue goal in 60 days?
- For you, what is the most annoying part of doing business?
- What are three daily routines you could possibly automate or delegate? (And explain how.)
- Who are three people who contribute to your daily business or work-related success? Why?
- What are three of your best qualities in doing business? (Describe why.)
- What's one new idea you'd like to make a reality for your work or business?
- What are three skills you could upgrade or improve on when it comes to how you run your business?
- What are three resources you'd like to tap into in order to grow your business or brand?
- What are three activities you could add to your workday that will make it fun?
- What are three Fortune 500 companies that have similar missions or values as you or your business? (Detail why.)
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Unapologetically, Chlöe: The R&B Star On Finding Love, Self-Acceptance & Boldly Using Her Voice
On set inside of a mid-city Los Angeles studio, it’s all eyes on Chlöe. She slightly shifts her body against a dark backdrop amidst camera clicks and whirs, giving a seductive pout here, and piercing eye contact there. Her chocolate locs are adorned with a few jewels that she requested to spice up the look, and on her shoulders rests a jeweled piece that she asked to be turned around to better showcase her neck (“I feel a bit old,” she said of the original direction). Her shapely figure is tucked into a strapless bodysuit with a deep v-neck that complements her décolletage.
Though subtle, her quiet wardrobe directives give the air of a woman who’s been here before, and certainly knows what she’s doing. At 24 years young, she’s a “Bossy” chick in training— one who’s politely unapologetic and learning the power of her own voice.
“I'm hesitant sometimes to truly speak my mind and speak up for myself and what I believe,” she later confessed to me a couple of weeks after the photoshoot. “It's always scary for me, but now I'm realizing that I have to, in order to gain respect as a Black woman— a young Black woman— who's still navigating who she is. And you know, I'm realizing that closed mouths don't get fed. And if I keep my mouth shut just because I'm afraid of what people's opinions of me will be or turn into, then that's not any way to live.”
For Chlöe, the journey into womanhood is about embracing who she is, without succumbing to the perceptions of what others think of her. From the waist up she’s everything you’d imagine. A gorgeous goddess with the kind of sex appeal that some work hard to embrace but fail to exude. But unbeknownst to anyone not on set, her bottom half is covered by a white robe, surprising coming from the girl who boasts “'Cause my booty so big, Lord, have mercy” on her first hit single “Have Mercy.”
But that’s the beauty of Chlöe. There’s more to her than meets the eye. More than what a few sensual photos sprinkled throughout an Instagram feed could ever tell you. Just like the photo-framing illusion of her portrayed from the waist up, what we know about the songstress is just the tip of the iceberg. There’s so much more beneath the surface.
Some hours later Chlöe leans back in a high chair as her locs are transformed from a formal updo to a seemingly Basquiat-inspired one. It’s pure art, and at her request, no wigs are a part of the day’s ensemble. She’s fully embracing her natural hair, a decision that wasn’t always a socially accepted one.
In the suburbs of Atlanta, Georgia, (Mableton, to be exact) Chlöe began to explore the foundation of her self-image. At an early age she and her younger sister, Halle, demonstrated a vocal prowess and knack for being in front of the camera that caught their parents’ attention. Soon after, they were sent on a parade of local talent shows and auditions, and eventually broke into the digital space with song covers on YouTube.
It was during these early years that Chlöe first learned that the entertainment industry could be unforgiving to those who didn’t fit a particular beauty standard. Despite the then three-year-old snagging a role as the younger version of Beyoncé’s character, Lilly, in Fighting Temptations, casting agents requested that her natural locs be exchanged for more Eurocentric tresses. Ironic, considering that growing up Chlöe saw her hair as no different than that of her peers. “I remember specifically in pre-K we had to do self-portraits and I drew myself with a regular straight ponytail, like how I would put my locs in a ponytail,” she says. “I just never saw myself any different.”
Chlöe would also learn the true meaning of a phrase that would later become an affirmation posted on her bedroom mirror: “Don’t Let the World Dim Your Light.” After attempting to wear wigs to fit in, the Bailey sisters instead chose to rock their locs with pride, which undoubtedly cost them casting roles. Yet they would have the last laugh when making headlines as the “Teen Dreadlocked Duo” who landed a million-dollar contract with Parkwood Entertainment, and the coveted opportunity to be groomed under the tutelage of a world-renowned superstar.
Credit: Derek Blanks
While that could be the end of a beautiful fairytale of self-empowerment, the reality is that it’s just the beginning of the story of her evolution. For most girls, the transition into womanhood takes place in the comfort of their own worlds, often limited to the number of people they allow to have access to them. But for Chlöe, it’s happening in front of millions of critiquing eyes just waiting for an opportunity to either uplift or dissect her through unwarranted commentary.
Many in her position wouldn’t be able to take that kind of pressure. But Chlöe is handling it with grace. “I feel like all of us as humans, we have the right to interpret things how we want,” she says. “I put art out into the world and it's up for interpretation. I'm learning that not everyone is going to always like me and that it's okay.”
Chlöe isn’t the first artist to receive criticism for her carnal content, and she certainly won’t be the last. In 2010, Ciara writhed and rode her way to banishment on BET when the then 24-year-old released her video for “Ride.” In 2006, 25-year-old Beyoncé received backlash for “Déjà Vu."
"I put art out into the world and it's up for interpretation. I'm learning that not everyone is going to always like me and that it's okay.”
So much so that over 5,000 fans signed an online petition demanding that her label re-shoot the video because it was “too sexual.” Even 27-year-old Janet didn’t escape critical headlines when she shed her image of innocence for a more risqué appearance with the 1993 release of janet.
It’s almost as if public reproach is a rite of passage for young Black women R&B singers on the road to stardom. Good girls seemingly “go bad” whenever they embrace the depths of their femininity, and fans only like you on top figuratively. But Chlöe has learned not to bow down to other people’s opinions, but to boss up and control the narrative. As the saying goes, well-behaved women seldom make history. If sex appeal is her weapon, she wields it well.
On set, Chlöe exudes the energy of Aphrodite in an apple red, off-shoulder dress with a sexy high split. In between shots, she mouths the lyrics to Yebba’s “Boomerang” as it echoes throughout the space in steady repetition at my recommendation. The hour grows late, yet Chlöe is heating things up as eyes stare in deep mesmerization of the girl on fire.
Credit: Derek Blanks
Through music, she explores the depths of her being, a journey that seems to be, at its foundation, rooted in self-discovery. Whereas their debut album The Kids Are Alright (2018) boasts a young Chloe x Halle empowering their generation to embrace who they are while finding their place in the world, their second album Ungodly Hour (2020) shows the Bailey sisters shedding the veil of innocence for a more unapologetic bravado.
What fans looked forward to seeing is who Chlöe shows herself to be on her debut solo album In Pieces. In an interview with PEOPLE, she confesses that releasing her first project without her sister was “scary.” "It was a moment of self-doubt where I was like, 'Can I do this without my sister?’”
Chlöe has never been shy about sharing her insecurities or her vulnerabilities, all of which are laced throughout the 14-track album. “I want people to have fun when they listen to it and to just realize that they're not alone and it's okay to be vulnerable and raw and open because none of us are perfect; we're all far from it. And I think it's healing when we all admit to that instead of putting up a facade.”
The gift of time has given the self-professed “big lover girl” more encounters with romance and heartbreak. Love songs once sung for their beautiful riffs and melodies become more than just abstract lyrics and are replaced by real-life experiences, which she tells me is definitely in the music.
In her single “Pray It Away,” for example, she contemplates going to God for healing instead of going at her ex-lover for revenge for his infidelities. “With anything dealing with art, I am completely vulnerable,” she says. “I'm completely myself, I'm completely open and transparent. So it's pretty much all of me and who I am right now.”
Has Chlöe been in love? That still remains to be said. Of course, she’s been linked to a few potential baes, but dating in the digital age isn’t as easy as a double tap or drop of a heart-eyes emoji. It requires a level of trust and vulnerability that’s hard to earn, and easy to mishandle. To let her guard down means to potentially set herself up for disappointment. “It’s difficult dating right now, honestly, because you really have to kind of keep your guard up and pay attention to who's really there for you. And you know, I'm such an affectionate person and I love hard.
"So when I meet the one person that I really, really am into, it's hard for me to see any others and I get attached pretty easily. And you know, I don't know, it's…it's a scary thing.”
Credit: Derek Blanks
“With anything dealing with art, I am completely vulnerable. I'm completely myself, I'm completely open and transparent. So it's pretty much all of me and who I am right now.”
While broken hearts yield good music (queue Adele), what’s in Chlöe’s prayer is the desire to be happy. What does that look like? Well, she’s still figuring that out herself. “Honestly, I'm the type of person who I don't truly learn unless I experience it. So it's like I can view and watch my parents and watch the loving relationships that I see in my life and be like, ‘Oh, I want that. I would love to have that.’ But then I also have to experience [love] on my own and see what my flaws or my faults might be or see what my good things about myself are. I feel like it's really all about self-reflection. And even though our base is our family and that's our foundation, we are still our own individuals and we have to find out specifically the things about ourselves that may be different from what we saw from our parents when we were growing up.”
Her ideal beau, she tells me, is someone she can feel safe to be her fun, goofy self with, but who also gives her the space to be the boss chick chasing her dreams. A man who understands that just because the world compliments her doesn’t mean she doesn’t want to hear those words from his lips or feel it in his touch. A bonus if he shows up on set after a long hard day of work with vegan cinnamon rolls. You know, the basic necessities. “I like whoever I'm with to constantly tell me they love me and that I look beautiful because I do the same. I am a very mushy person, and if I see something or you look good, I will never shy away from saying it out loud. And I want whoever I'm with to do the same, be very vocal. Tell me that you love me. Tell me what you love about me because I'm doing the same for you because that's just the person I am.”
Until she meets her match she’s married to the game, and for now, that seems to be perfect matrimony.
Credit: Derek Blanks
On stage at the 2021 American Music Awards, Chlöe solidified her position as a force to be reckoned with. It was a full-circle moment. In 2012, bright-eyed and baby-faced Chloe and Halle would walk onto the set of The Ellen Degeneres Show and blow the audience away as they bellowed out their future mentor’s song. Ellen would present the sisters with tickets to attend the AMAs, assuring them that they would be back and had a promising future. Nine years later, Chlöe descends from the sky cloaked in a snow-white cape and matching midriff-baring bodysuit for her debut performance. It’s the first time she’s graced the stage of the very award show that she was once an audience member of.
As she shakes and shimmies and boom kack kacks out her eight counts, it’s clear that she’s in her element. Just like her VMA performance a couple of months prior, and the many more stages she’ll continue to grace, she brings an energy that has earned her comparisons to the beloved Queen Bey herself. An honorable statement, considering few R&B songstresses are getting accolades for their entertainment capabilities. It’s on these very stages, in front of hundreds of astonished eyes and millions more glued to their televisions at home, that she tells me she feels most sexy. Powerful, even.
But off stage, it’s a different story.
It’s more than just the commentary about her image and media-flamed rumors that get to her. Mentally, she’s in competition with herself. The desire to be the best burns at the back of her mind with every performance, every production, and every time she steps into the booth. Before, she could share the weight of this burden with her sister. Being a part of a duo meant she could turn to Halle for quiet confirmation and encouragement without a word being exchanged. But lately stepping on the stage means stepping out on her own. And despite being a breathtaking, five-time Grammy-nominated star, Chlöe doesn’t escape the reality that sometimes we can be our own worst critics.
Over the last year, she’s been coming to terms with who she is on her own while overcoming the fear of failing to become who she’s destined to be. While the world waits to see how Chlöe wins, the real triumph is in every day that she chooses herself and continues to walk in her purpose. “I don't really have anything all figured out, honestly. But what I try to do, a lot of prayer. I talk to God more and I just try to do things that calm my mind down and just breathe.”
To whom much is given, much will be required. She’s been chosen to walk this path for a reason. Once she fully embraces that everything she’s meant to be is already inside of her, she’ll be an unstoppable force. “My grandma, Elizabeth, she just passed away and my middle name is her [first] name. So I feel like I truly have a responsibility to live up to her legacy that she's left on this earth. I hope I can do that.”
There’s no doubt that she will. With a role in The Fighting Temptations at three years old, a million-dollar record deal, a main role on five seasons of Grown-ish, five Grammy nominations, a number one solo record in Urban and Rhythmic Radio, a debut solo album, and starring roles in recently released movies Praise Thisand Swarm (just to name a few), Chlöe’s certainly already made her mark, and she’s just getting started.
Photographer & Creative Director: Derek Blanks
Executive Producer: Necole Kane
Co-Executive Producer: EJ Jamele
Producer: Erica Turnbull
Digitech: Chris Keller
DP: Alex Nikishin
Gaffer: Simeon Mihaylov
Photo Assistant: Chris Paschal
2nd Photo Assistant: Tyler Umprey
Features Editor: Kiah McBride
Special Projects: Tyeal Howell
Hair: Malcolm Marquez
Makeup: Yolonda Frederick
Fashion Styling: Ashley Sean Thomas
For More: Cover Story: Issa Rae Comes Full Circle
De-Stress & De-Clutter: How To Get Your Work Life Together
Whenever many of us think about spring cleaning, we're likely to address everything but our work lives. But just as it's important to change out those winter coats for spring jackets or organize all those hoarded thrift finds that have multiplied in your spare room's closet (or is that just me?), it's a good idea to clear out the stress, clutter, and disorganization in your work life.
Here are a few things I've done over the years to get on the right track and really bring in a new season of winning, empowered and refreshed:
1. Do a digital detox.
And no, this isn't about fasting from scrolling Instagram for a month. This is all about bulk-deleting those 300 sent e-mails that you no longer need to keep track of. It's about going into your Google inbox and getting rid of all 21,000 of those social media notifications. It's unsubscribing to newsletters that you rarely read (or don't need to be reading during work hours). It's emptying out your digital trash and feeling okay with the fact that you'll never see that old proof-that-I-finished-my-part-of-that-project e-mail you kept from a year ago.
It's about finally printing out the dozens of photos you took on that trip to Mexico two years ago. Delete numbers, photos, and apps from your phone and computers that you no longer use (or want to use). Organize those random files on your desktop into folders and only keep things that are current or super-important to the job that you do.
Since I'm the ultimate e-mail and digital file hoarder, I often do this process in small chunks---a few tasks at a time, over weeks---so that I don't overwhelm myself. Also, if there are files that you just can't part with (especially the large ones taking up space in your inbox or on your computer's hard drive), put them in a Dropbox, Google Drive, or other online file-storage option, invest in an external hard drive, or get a USB stick. Be sure to name files accordingly and utilize organizational tools like folders and bookmarks.
2. Set up automated tasks.
For example, I've found that using email templates is very useful for quickly inputting responses or copy that I repetitively have to type to do the work I do. If I need to send an invoice, I have a template for it, and I can schedule them to go out at the appropriate time. Even for corporate gifting, holiday greetings, correspondences with new writers, client onboarding, scheduling appointments, submitting reports, or other managerial things, I've found ways to automate certain tasks so that I have more time on my hands to focus on the creative aspects of my job.
If you can automate (or schedule) anything, set those up as ahead of time as possible using platforms like Calendly, Asana, or Hubspot. You can even automate your social posts, and it's not the formulaic, restrictive process it used to be.
Anything that you do every day, month, quarter, or year that is a routine that hardly ever changes much should be automated, as it will literally make your workday that much easier.
3. Upgrade your office space with small touches of joy.
For me, this means adding comfort, color, and great memories. I find that when the space I'm working in reflects vibes that make me feel happy, I'm more likely to be productive. Also, since I'm quite tall and work in front of a computer for 80% of my day, I have to be comfortable, so my desk, chair, and other amenities have to accommodate me.
I always keep photos of my family and accomplishments around wherever I'm working (even if it's just my computer's screensaver), something that's in a bright, vivid hue on my desk (like a candle, mug, or picture frame) and an ergonomic desk setup.
If I have to throw out, return, or donate a chair or desk simply because it's no longer comfortable or practical for me, I unapologetically do, no matter when or where I bought it.
I'm also a minimalist when it comes to my office space, as I don't like a lot of books, knickknacks, and other items lingering around that don't have a purpose. Figure out what office vibe and style allows you to work at your best in your office, and if something doesn't align with that, make the necessary adjustments.
4. Do an assessment of your professional life, passions, and goals.
You can liken this to how many who help people get a handle on their closets often start by asking them to assess what clothing they already have in them. Well, in this case, you'd need to just check in with yourself in terms of your current work-life outlook, the things you like about it, what you'd like to achieve in the season that you're in, and what you don't like about any of it. This is helpful because oftentimes, at the core of work-related clutter (both mentally and physically) is a lack of insight into where you are professionally and where you'd like to be. Many of the moves I make in my career start with that---down to the smallest work-related tasks and how I approach completing them.
You don't have to have all the answers, but it's a good idea to at least sit and write a few things down. Write down the processes that stress you out the most and possible solutions. Take some time to find out what type of optimal environment you work best in and how you contribute to the culture of that environment (if at all). What do you love about the everyday things you do at work? What do you dislike? Are there ways of communicating, project management, systems management, or technology processes that could make things easier or more challenging?
There are also online assessments to help you figure out more about how you can maximize your potential at work.
5. Get some help.
Decluttering and purging anything can be quite exhausting and mentally draining, so getting help in the areas where you need it is key.
For the digital detox, for example, I had to seek out someone who knows more about how to streamline things in a way that made sense to me, especially since I handle a lot of documents, emails, and image files that I don't like to get rid of.
Talk with an IT colleague, that one smart, always-organized friend, or even a coach to get the assistance you need for spring-cleaning aspects of your work life that you find challenging to address on your own. By taking things one step at a time and moving forward with a positive goal of shifting the energy in your favor, you'll find solutions that work for you.
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