11 Boss Women On The Biggest Career Mistakes They Made In Their 20s
From choosing love over our career goals to not negotiating, there are so many career mistakes that young women make.
When we are in our 20s, we are at a very vulnerable state in our lives. For some of us, we just finished college, are working at our first “real" jobs, and we are even starting families. Through the midst of it all, we tend to make simple mistakes as it relates to our careers. Since I graduated from undergrad, I've made plenty of the same mistakes that my female friends have made. I cringe now when I think of them from time to time, but now that I know better, I try my best to do better.
Recently, I was able to connect with a few girl bosses in various careers and personal backgrounds. Each woman shared their biggest career mistake and what they learned from it. Whether you are a graduating college senior, just starting out on your own, or a 20-something woman that is already working, you will be able to benefit from the wisdom of each of the boss women below. Each woman shared her own career mistake and how they've managed to get in formation (slay girl, slay!)
1. Sheena Allen (@whoisSheena)
Entrepreneur & Founder of Sheena Allen Apps & Insta Funds
Learn when to ask for help.
"My biggest career mistake in my 20s was thinking that I could do it all on my own. I started my first tech company as a solo founder and actually waited a good amount of time before seeking mentorship or a team to help in growing my company. I learned that it is important to have a great team in order to build a great company. Trying to do everything on your own will tire and stress you out, which only leads to hurting your company."
2. Troy Washington (@thetroyla)
On-Air News Reporter for KSLA
Have faith in yourself over everyone & everything else.
"I vowed that I would keep this mistake between myself and the reporter who found me bawling my eyes out in the restroom but if it helps someone else out in their career then I suppose the embarrassment is worth it. It took a nightmare live shot during the evening news to teach me that you shouldn't depend on technology. No matter how confident you are in your smartphone, keep a backup plan!
"I was reporting live on a complicated story, the anchor tossed my phone to me and my iPhone cancelled out of my notes. I spent the entire shot stumbling and trying to open the note in my phone. Finally to no avail I tossed the phone back to the anchors feeling defeated. To top it off a viewer came up to me right after and said "got a little tongue tied there at 5." I was mortified. Now no matter how simple or complex the story is I don't complicate things or depend on anything else. I rely on old fashioned pen, pad, bullet points, and what I know. This taught me to trust myself instead of a flimsy note in my phone.
"Believe it or not that moment built my confidence because I knew I could never repeat that mistake. In essence falling on my face has always delivered the best lessons. That was one of my first live shots and I've done hundreds more since then but I'll never forget that one. That's the one that humbled me, it hurt, and taught me that I never wanted to experience it again. In TV, you'll make mistakes and that's inevitable because you're human and likely those mistakes will be broadcasted, but as long as you don't repeat those mistakes, you'll be fine."
3. Shay Lawson (@ShayMLawson )
Diversity Professional & Attorney
Stay hopeful, be fearless, & focus on you.
"I have quite a few career mistakes that comes to mind, but this one sticks out the most:
"When you start working, you need to negotiate. Women make $0.79 for every $1 a man makes, often because men demand more. I didn't even know this was an option when I was in my twenties and in talking to my girlfriends they all agreed that they wish they had negotiated for a higher salary in their first few jobs. I know that's not something most young women are comfortable doing, but men do it ALL THE TIME!!!
"Do the research, know how much people at the job and experience level make, and also come prepared to explain why you want what you're asking be it for relocation, for cost of living, etc. Once you've been offered a job, don't worry you will lose the offer. You're not being petty over pennies, you're getting what you're worth."
4. Emily Drewry (@emily.drewry)
Assistant Social Media Editor at Forbes
Never let the world drown out your voice.
"My biggest mistake thus far has been holding back my thoughts in the workplace because I lacked confidence. As a 22-year-old in my first role out of school, I would frequently wait to bring ideas to the table until I was 100% sure they were good and would be successful. At a certain point, my boss sat me down and told me that I needed to stop focusing on my age and let the ideas speak for themselves.
"It's harder than it sounds to forget about seniority and structure at the office, but doing so let me shine so much more -- and perform better in my role. I try to remember that every day is a new opportunity to prove my skills, and I can't do that without speaking up."
5. Gia Peppers (@giapeppers)
Freelance Entertainment Journalist & On Air Talent (portfolio includes the NBA, BET, ESSENCE, Hot 97 & more)
Be faithful & fearless to YOURSELF.
"I've learned a lot in the first five years of my 20s. The top thing I want other young women to know is that an internship doesn't guarantee a job & you should be loyal to you. In college, I interned almost every semester to make sure I knew exactly what I wanted to do in radio and/or TV. When I graduated, my resume was stacked with "experience." I just KNEW everyone was going to be knocking at my door (or LinkedIn page) with opportunities. But, after I got all my cookout celebrations out of the way, I still had no offers and had to take a job outside of my field to start paying back loans. I hated it. I would go in the bathroom and cry.
"BUT, the resources I had-- like a laptop and overnight car service-- motivated me to work all hours of the night to ensure I would not be there longer than one year. Every moment you have is meant to prepare you for the next one. Do your best in that moment and learn all you can. And, don't be surprised if no one calls you RIGHT after you graduate. It takes a job to get a job. Once you get that job, be loyal to YOU. Our parents grew up in a time when you could stay at one company for 20 years and move up to make more money and gain experience within the company. Unfortunately, our generation doesn't have that security. In many fields, companies barely pay full salaries with benefits. In fact, many of these same companies don't offer raises until an employee threatens to leave. Have your own brand. Make yourself irreplaceable and save for rainy days. In this economic climate, you will probably have some."
6. Nicaila (Caila) Matthews (@CailaKSpeaks)
Senior Manager of Social Marketing at NPR, Founder of CailaKSpeaks.com
Setbacks are temporary. Comebacks create legends.
"My biggest career mistake in my 20s was believing that a job at a big media conglomerate would guarantee happiness and career growth. I was lured by the brand's name and glitzy reputation, but I did not take the time to assess how it aligned with my career goals. Two years and one horrible boss later, I ended up quitting my first job out of college and going through a frustrating period of unemployment, having to move back home, and feeling like a failure. I bounced back by starting to side hustle as a blogger and freelance writer, which led me to my calling as a digital and content marketer.
"If you're reading this and experiencing the same feelings of disappointment and confusion that I did, take the time to assess what you want from your career and life and write down three things you plan to do to get there. I worked at an unrelated job for one and a half years while I hustled to get to the next stage of my career, and ended up living with my parents for three years (two years longer than I planned). In the end I know you'll be happier and that much closer to fulfilling your authentic purpose on this earth. This low point in my career would later propel me into social media marketing and drive me to get my MBA. As I learned from my experience, sometimes you have to take a step backward before you can move forward in pursuit of your goals."
7. Sidnee Michelle Douyon (@sidmich_)
Editorial Operations Assistant at Forbes, and Music and Entertainment Writer/Reporter
Never let your insecurities get in the way.
"My biggest career mistake I've made in my 20's would be second guessing myself. There were times I was hesitant and even shied away from going after certain opportunities and interviews because I thought I didn't have what it takes to execute at 100%. I learned that you have to always go for what you want, especially in your career.
"If you let the fear of failure or your insecurities keep you from going after what you deserve than you'll never reach the heights of your potential. If I could go back in time to prepare myself for the struggles I went through, I wouldn't do anything different but develop a personal confidence within myself early on and really use that as a driving factor to push me forward in my career. Fast forward, I've definitely evolved into a much more confident journalist. Before I even execute an interview or gain an opportunity, I go into it like I know I'm going to "kill this." I also have evolved my work ethic to align with a 'newfound career confidence' where I put in the work & research to be able to go into an assignment or interview 100% confident and prepped."
8. Melissa Kimble (@Melissa_Kimble)
Senior Social Media Manager at EBONY, Leader of The#blkcreatives
Know when to walk away & when to stay.
"The biggest mistake I've made is giving away my power. Anytime my true value wasn't recognized or my energy was being depleted in situations that didn't fulfill or honor me, I should have made the decision to walk away from those things sooner.
"If you're constantly giving away your power, you're living in a place of fear and fear destroys everything, especially your chance to succeed and build the career life you really want for yourself."
9. Ariel Lopez (@ArielLopez__)
Founder of 2020Shift
Try to make the most out of every situation & be the best.
"The biggest mistake I made was making a leap before I was ready (I was 22 at the time) I was working full time at a staffing firm and also on a startup idea when I was presented with an opportunity to work from home. I immediately thought that this is was a dream situation. Make money and have more time to work on my own thing- why not? Unfortunately the position fell through within a month's time and I had to scramble to figure out how to make it. I went through a super rough time and almost had to move back home (nightmare) but was able to land something a few months later. I learned that you can't try to game the system. I wasn't taking the position to give 100% effort to them, I was using them as a catalyst to get my own thing off the ground (bad karma). It also taught me to really think things through before making life altering decisions. I wasn't financially prepared to sustain myself and my expenses if my job didn't work out.
"Ultimately, I took a risk on leaving something stable to pursue the unknown, but I think it paid off. That experience fueled me to do it all over again, just better. I actually don't believe in mistakes, just lessons learned. I recently took the leap again, but this time I had things aligned differently. Since then, I've evolved a ton as entrepreneur and also as a career coach. I'm able to advise people on their careers because of my personal experience. It's also showed me that if I can bounce back once I could do it twice. I'm unafraid because I know what I'm capable of."
10. Emmelie De La Cruz (@EmmelieDeLaCruz)
Author of Make Yourself Marketable& Personal Branding Strategist
Your personal brand is more important than you may think.
"The biggest career mistake I made was believing that I needed the right credentials to be an expert. Have you heard of Malala? Imagine if she censored herself because she considered herself too young and her story insignificant. We wouldn't have the youngest Nobel Peace Prize winner. Our personal brand is a combination of our personality, skill sets, and the value we create for others.
"It is all about who we are, what we do and how others perceive us through those in-person and digital interactions. Building your personal brand inside and outside the workplace is necessary to accelerate your career. Our insecurities around self-promotion, our credentials, and contributions will disappear when we understand that the stakes for us to succeed as a sisterhood are so high that we are almost forced to tell our story for the sake of being a resource to someone else. We have an important story that needs to be told and heard. The unique combination of your personal and professional experience, your skills and accomplishments already make you an expert."
11. Tola Lawal (@tola617)
Entrepreneur & Founder of SixOne7Creative
Never let them see you sweat or lose your cool.
"One of my biggest career mistakes was bringing my emotions to work. In my early 20's I let a co-worker take me out of my professional element and I went OFF in the office. My bosses and co-workers were SHOCKED! I was a great employee and most times I ignored the tomfoolery but at that point I was fed up. As busy as I was supporting a number of senior level executives, I didn't have time. But that day... that day, I had time. But after I lit the office up, I was SO embarrassed. After this mistake, I learned a few things. I learned the importance of a poker face, and that most of what goes on at work is not personal. Don't take any of it personally. If there is an issue, go to your immediate boss, and if that doesn't resolve the issue, take it to Human Resources.
"BUT don't EVER give someone the satisfaction of taking you out of your calm which can result in you embarrassing yourself. Since that mistake, I don't take much personally. There is always going to be someone, something, that ruffles your feathers at work. Be like a duck and keep calm. Don't let anything get to you, and if it does, vent in private. Vent to your accountability partners, your friends, but NEVER, EVER at work."
Featured image by Shay M. Lawson
Originally published December 9, 2017
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Brittani Hunter is a proud PVAMU alumni and the founder of The Mogul Millennial, a business and career platform for Black Millennials. Meet Brittani on Twitter and on the Gram at @BrittaniLHunter and @mogulmillennial.
ItGirl 100 Honors Black Women Who Create Culture & Put On For Their Cities
As they say, create the change you want to see in this world, besties. That’s why xoNecole linked up with Hyundai for the inaugural ItGirl 100 List, a celebration of 100 Genzennial women who aren’t afraid to pull up their own seats to the table. Across regions and industries, these women embody the essence of discovering self-value through purpose, honey! They're fierce, they’re ultra-creative, and we know they make their cities proud.
VIEW THE FULL ITGIRL 100 LIST HERE.
Don’t forget to also check out the ItGirl Directory, featuring 50 Black-woman-owned marketing and branding agencies, photographers and videographers, publicists, and more.
THE ITGIRL MEMO
I. An ItGirl puts on for her city and masters her self-worth through purpose.
II. An ItGirl celebrates all the things that make her unique.
III. An ItGirl empowers others to become the best versions of themselves.
IV. An ItGirl leads by example, inspiring others through her actions and integrity.
V. An ItGirl paves the way for authenticity and diversity in all aspects of life.
VI. An ItGirl uses the power of her voice to advocate for positive change in the world.
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Your May 2024 Horoscopes Are All About Setting Intentions, Focus, And Self-Discovery
Explore your sign’s 2024 horoscope predictions to learn what is in store for you this year in love, career, and more. Check out the love compatibility of each sign to learn more about zodiac pairings and all things compatibility.
May is a month of intention and about focusing on what you are creating in your life right now. Eclipse Season is over for the time being; Mercury is direct again, yet there are still more opportunities for breakthrough and self-discovery. The month begins with Pluto going retrograde in Aquarius on May 2, signifying the need to reclaim your power right now. Pluto will be retrograde until October 11, and this is a good time to experience a renewal within your belief systems, friendships, and community. After a time of change and regrouping, May is a time to create a new path for yourself and feel more secure in doing so.
Taurus Season is in full bloom, and on May 7 the Moon will be joining the Sun for the New Moon in Taurus. This New Moon is an opportunity for luxury, self-care, stability, and harmony.
When the Moon is in Taurus, we are guided towards taking care of ourselves more, and this is a good time to set your intentions for where you want to experience more ease, love, and TLC in life. This New Moon will be a powerful time for manifestation, so make sure you are focused on what you want to create in your life right now. Mercury then moves out of Aries and into Taurus on May 15th, and perspectives move into the energy of more logic, patience, and practicality.
Mercury in Taurus brings the focus to your finances as well, and this is a good time to ask for a raise or promotion, take care of finances, or build your assets.
What May 2024 Has In Store For Your Zodiac Sign
Gemini Season makes its debut on May 20 this year, and the Sun moving into these air signs makes the energy a little lighter and playful, and by the end of the month, people are looking to have some more fun. With a Full Moon in Sagittarius happening a few days later on May 23, the end of May is an exciting, eye-opening, and adventurous time. The Sagittarius Full Moon is the Flower Moon of the Year, and it’s time you receive yours.
Venus moves into Gemini on May 23 as well, and during this time, relationship matters can feel a little more all over the place. However, this is also a more social, charming, and dynamic time for love as well. While Venus is in Gemini, remember that communication is key, and a more open-minded and flexible approach to matters of the heart is needed.
One of the most important transits of the year happens as May comes to an end, and that is Jupiter's move into Gemini. Jupiter has been in Taurus for the past year, helping us grow and get the full picture when it comes to your stability, relationships, and finances, and Jupiter's move into Gemini brings things into focus when it comes to your self-expression, communication, connections, and joy in life.
Jupiter will be in Gemini from May 25, 2024, to June 9, 2025, and this is the perfect opportunity to connect with your creative genius and meet new people with whom you resonate. May, overall, has a lot of potential for opportunity, insight, and collaboration, and this is the perfect month to set your intentions for the future while also living in the moment with the people you love and who inspire you.
Read for your sun sign and rising sign below to see what May 2024 has in store for you.
ARIES
May is a coming-together month for you, and things are starting to make more sense after Mercury retrograde in your sign for most of last month. You are getting more time within your relationships and close partnerships right now, and the New Moon on May 7, happening in your 2nd house, is when this connection, love, and stability begin to come in for you. You have been asking yourself the important questions and are ready to break ground and create the new beginnings you see for yourself.
With Mars in your sign for the entire month of May, you have a lot of energy and passion at your disposal right now, and you are making things happen for yourself. This is a good time for feeling connected to your body and for seeing positive results regarding your health. Jupiter moves into your house of communication at the end of the month where it will be for the next year, and you are moving into a time of more grace, understanding, and opportunity for self-expression right now, Aries - own your voice.
TAURUS
The Sun is in your sign, and you are shining authentically in who you are, Taurus. May is a beautiful month for growth and a time when you are finding your balance between letting go of the past and remaining true to yourself in the present. The New Moon of the month is happening in your sign on May 7, signifying a time of new beginnings for you and when it comes to your goals in life and your sense of freedom.
Be confident in your desires, and know yourself, Taurus. With all the manifestations that are coming forth for you this month, clarity is one of them.
Mercury enters your sign on May 15, and this is a time of positive communication, connection, and gaining some new wisdom. With Mercury in your sign, be prepared for some extra communication on your hands as people are looking to hear your perspective. Jupiter moves out of your sign and enters Aries on May 25 after being in Taurus for the past year, and the luck you have been experiencing in life transfers to your finances, income, and value systems. Overall, you are finding your way and making sense of it all this month.
GEMINI
May is a time of rebirth for you, Gemini. You are in a good head space this month now that your ruling planet, Mercury, is officially out of retrograde and direct again. This is a powerful month for you when things are turning around for you and some extra good karma and luck are coming your way. With the Sun in your 12th house for most of May, you are getting an opportunity to renew and heal from the past and to gain some new understanding of where you have been in life and what you want to create moving forward.
Gemini Season begins on May 20, and it’s your time to shine! Gemini Season this year is a month full of opportunity and clarity, and you are bringing your best self forward. There is a Full Moon on May 23 in your opposite sign, Sagittarius, and love matters are coming full circle for you now so that you can let go of old belief systems that don’t serve you or your relationships anymore. Your most important astrological transit of 2024 happens at the end of the month on May 25, as Jupiter enters your sign for the next year. Jupiter in your sign signifies good luck, fortune, and personal success in your future.
CANCER
This month is about finding your balance, manifesting, and working together with others, Cancer. It’s about choosing peace and trusting your intuition right now to guide you forward. The Sun is in your 11th house in May, and you are thinking of the big picture and not letting anything get in the way of your vision or purpose. There is a New Moon at the start of the month in this area of your chart, and your power of manifestation is especially strong this month, so make sure you are following your true North and setting the intentions that feel right for you internally.
On May 23, Venus enters your 12th house of endings and closure, and love is about moving on and moving into more healing and emotionally receptive experiences. Relationship matters are moving through a transformation now, and you are learning a lot through your partnerships, both old and new, this month. There is a Full Moon on May 23 as well, and this Full Moon will be bringing up old work, projects, and intentions; it’s time to congratulate yourself for your successes and how far you come, as others will want to support you more right now as well.
LEO
Over the next month, you are getting the opportunity to stand your ground, speak up for yourself, and claim your space, Leo. This month is about being your biggest cheerleader and seeing yourself in the way you wish others to see you. The Sun is in your 10th house for most of May, and you are focused on taking action and going after your dreams right now. The New Moon on May 7 is a good time to set your intentions for said goals and dreams and to really believe in yourself.
On May 23, there is a Full Moon in fellow fire sign Sagittarius, happening in an area of your chart that has to do with your happiness, romance, creative self-expression, and overall joy for life. You are getting the full picture of where your priorities are or need to be, and are bringing more attention to the things that are going to truly make you happy and fulfilled at the end of the day. Jupiter enters Gemini on the same day where it will remain until 2025, and this move is expanding things for you when it comes to your friendships, community, and social networks.
VIRGO
May is a month of connecting with your soul and creating harmony in your life, Virgo. You are moving into a time of greater freedom and authenticity, and May is a good month for travel for you. With a New Moon in Taurus at the beginning of the month, you are expanding your horizons and gaining some much-needed inspiration. This is the time to do things differently and to not be afraid to take risks, and a leap of faith in yourself. You are feeling a little more optimistic in May, and this is creating an opening in your life.
On May 23, we have a Full Moon in your 4th house of home and family, and this is a good time for experiencing closure in this area of your life, and like things are coming full circle for you here. The first half of the month is all about adventure, and the second half of May, you are looking to build in your stability. Jupiter moves into your 10th house of career and success before the month ends, and you enter a year-long transit that will be positively influencing and expanding your reputation and goals in life.
LIBRA
May is an opportunity to learn, inspire, and spend some more time with the people who bring this energy out of you, Libra. The month begins with Pluto going retrograde in your 5th house of love, and you need some more time to grasp what is going on in your heart and how you can find your power in life here more. There is a lot to learn and discover this month, and the New Moon on May 7 will be an eye-opening and transformative moment for you where you can dive deep into your love life and commitments and see where a new beginning may be necessary.
There is a Full Moon happening later in the month and this Full Moon will be bringing forth spiritual guidance into your life. This is a Full Moon to connect, communicate, and share your insights and ideas with others. On May 25, Jupiter enters Gemini and moves into your 9th house of adventure, and you are entering a year of travel, enlightenment, spirituality, and higher education. Your mind is your gift right now; trust you have everything you need to experience greatness and be open to meeting new people who will help you get there.
SCORPIO
This month is about remaining open and receptive to what is possible for you and your future, Scorpio. You are in a good space to receive your due blessings and rewards, but your heart must be open to receive them. Your ruling planet, Pluto, goes retrograde at the start of the month on May 2, and this Pluto retro transit will allow you to rebuild your vision for the home, and help you figure out where you can bring more of yourself into your surroundings.
A lot of the energy of the month is in your opposite sign, Taurus, meaning it’s in your love and partnership zones.
May is one of the most significant months of love for you out of the year, and the intentions you set for your relationships on the New Moon this month will be creating magic in your love life for the rest of the year. On May 23, there is a Full Moon in the sign just after yours, bringing attention to your finances, income, and self-confidence in it all. The end of May is a time to focus a little more on your stability in life and to take a look at your finances. This is a good time to clean your purse or wallet, create some feng shui, and go over your assets.
SAGITTARIUS
Your guidance for the month is to go with the flow and trust your instincts, Sagittarius. The New Moon happening on the 7th is a new door opening for you, your health, and your daily routine, and you are focused on what is going to be best for you and your well-being overall. You are trusting your next steps ahead and remaining grounded with where things are in the meantime. It’s all about trust right now and how much of it you can have for yourself.
The Full Moon of the month will be in your sign on May 23rd, and this is a powerful Full Moon for you of closure, clarity, and self-confidence. You are letting go of what doesn’t resonate with who you are now and what you want to expand in your life. This is a good time to say your affirmations, meditate, and get out of your own head. Before the month ends, your ruling planet, Jupiter, enters your opposite sign, Gemini, and your love life gets an extra boost of good luck right now. Jupiter will be in your 7th house of partnership until 2025, and you are entering a year of harmony, Sagittarius.
CAPRICORN
Abundance is your birthright, and you are tapping into this energy this month, Capricorn. May is a month full of opportunities for you, and a lot of this good juju is coming through for you romantically right now. The Sun is in your 5th house of the heart for most of the month, and there is a New Moon here on May 7 as well.
At the beginning of May, make sure you are focused on communicating clearly, owning your passions in life, and having some more fun with love and the romance that wants to bloom for you here.
With Mercury entering your 5th house on May 15 as well, you could be receiving a surprise message or be having some interesting conversations right now that switch things up for you in love. On May 25, Jupiter moves into an area of your chart having to do with your health, lifestyle, and work life, and you are overall going to be coming into balance more here and experiencing some fortunate opportunities at work and within your daily routine. Overall, May is a month that is setting you up for success, Capricorn.
AQUARIUS
May is an opportunity for you to connect, move forward, and learn more about yourself and your heart, Aquarius. You are paying attention to the signs right now and making sense of things that may have gone past you before. With Pluto going retrograde in your sign as the month begins on May 2, you are someone who will be moving through a journey of self-discovery for the rest of the year and will be figuring out where your true power is in life and how to hone in on it more.
The New Moon in Taurus on May 7 is a new beginning for you and your home life, and a lot of this month will be about finding those people and spaces that feel like home to you and that make you feel supported in who you are. Jupiter enters a fellow air sign on May 25, and Jupiter in Gemini brings in a year ahead of romance, creativity, confidence, and finding your joy. Things are shifting big time in your life right now, but you are figuring out what works for you and what doesn’t.
PISCES
It's time to protect your energy and create boundaries where needed, Pisces. May is a month of checking in with yourself and emotionally regulating before moving forward. Pluto goes retrograde at the start of the month and will be retrograde in your 12th house of closure, secrets, and healing until October. What this means for you is a chance at clarity of the heart, but this transit can also bring up old issues or power struggles of the past. Remember to learn from past experiences and decide for yourself today how you want things to go for you from here.
There is a Full Moon in Sagittarius on May 23, and being a mutable sign like Sagittarius, you can tap into the potential of this Full Moon effectively. This is the time to turn a page within your career or professional world and see some resolution here. Before the month ends Jupiter enters your house of home, family, and history, and you are going to be opening your mind on these matters over the next year. You could be expanding the home, moving, or experiencing a deep sense of healing here now.
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Featured image by Kyra Jay for xoNecole