

My friend Jessica is three years younger than me and as much as she watched me maneuver my way out of Tennessee to New York City, I, too, kept tabs on her trajectory to success in Chicago.
So on New Year's Eve we met up to laugh, cry and candidly share our wins with one another. During our dinner she revealed to me that she met up with some of her former high school classmates who made her feel bad for successfully "making it out" of Tennessee and having a fruitful career. She admitted to downplaying her experiences so that her former classmates would feel comfortable around her instead of the usual intimidation and jealously. It was disheartening to me that she felt the need to dim her light to spare someone else's feelings, and I wondered how many times we have both underestimated, undervalued and underrated our achievements.
Just two weeks later, I went to a networking event where I circled the room trying to connect with other professionals. As I began to introduce myself to some of the attendees, my friend, Stephanie interrupted one of my conversations and started to continue telling this person all of the small achievements that I've had in my career thus far. It was amazing that she could introduce me better than I could speak for myself. Afterwards, Stephanie pulled me to the side and asked me why I downplayed my achievements. Maybe I didn't think it was relevant, maybe I didn't think it was important, but I didn't know why I decided not to share my wins with this stranger.
I learned two important things from those encounters:
- First, I needed go back to the drawing board and rework the contents of my elevator pitch.
- Secondly, I needed to work on being bold and unafraid to let my achievements shine.
If I could master those two things, I could achieve the goals that I set for myself this year.
According toThe Atlantic,
"Men overestimate their abilities and performance, and women underestimate both, even though there's no difference in the quality of their performance."
Whether it's a promotion, negotiating salary, dating or even being able to confidently share our success with friends, women downplay their achievements in many ways. Communications professional and ex-Hill staffer Safiya Jafari Simmons was stunned when she came across the stats about the confidence gap between men and women. She decided to do something about the way women project their confidence in and out of the boardroom by founding Leap Executives Strategies.
I recently attended her Leap Luncheon in Brooklyn where she shared some major keys for confidently sharing your achievements in order to win:
Own Who You Are
Women are so often judged, labeled and categorized that it can feel very overwhelming and intimidating to imagine being completely and authentically ourselves when the consequences of such boldness are unknown. We must contend with so many different opinions of what is proper that we often prioritize the comfort of others over that of ourselves to "keep the peace" or to benefit the greater good. So we shrink; we make ourselves, our personalities and our skills smaller so as to be less infringing on others, less intimidating to others and to not rock the boat. From my purple Mohawk, to my colorful clothing and my unashamed devotion to Christ, I'm prayerfully and loudly leading a charge to encourage women -- especially women of color -- to own themselves, validate their own goals and chart their own course. We only live this one life. I'm not wasting mine building someone else's dream or watching others shutter their own.
Don't Shrink Or Diminish Your Achievements
Each of us is created to do something that no other person on this planet can do. Yes, there may be one million women in the arena you want to get into, but no one else will perceive, process or attack the problem the way you will.
My boldness is anchored in my faith and in the Word of God that says that He didn't give us a spirit of timidity. So I glorify my Creator when I share with others what I've been able to accomplish because of Him. I want to encourage as many women as possible to get that truth as well: it doesn't benefit anyone when we shrink or diminish our successes. It negatively impacts the lives of those attached to us, those watching us and those we're helping to groom. If fear holds you back from being bold, then do it to the glory of the One who created and purposed you. How can we influence a new generation of entrepreneurs, CEOs, thought leaders and game changers if we don't own our successes, accomplishments and advancements? How do we show to those coming up behind us what power they have if we don't model it for them? I want women of all ages and stations to see me -- loud, purple hair, bright clothes and joyfully declaring what I will and won't accept in my life and career -- and know that they can do and have the same and more.
Balance Humility With Confidence
It's imperative that we do two things in all of those scenarios. First, we enter the scenarios with a mission to hear and truly listen. Second, that we enter the scenarios strategically, knowing that we're a value-add and that we deserve good things. In networking situations, many women avoid strategically approaching and interacting with established, successful or celebrity folks because they don't want to be categorized as pushy, or they don't know what to say. Most often, if we'd make the first move - just approach, introduce ourselves and extend our hand for a handshake - what follows will flow naturally. We must get better with strategically growing our networks.
If we want to climb the ladder in the industry we're in, or jump into a new arena or land a new client, think about the people who are farther along than we are in the area and then set to the business of making them a part of our network. In interviewing and negotiating, we have to balance humility with confidence. Yes, we want potential employers to think we're a good catch, but we also have to have the mindset that we're evaluating whether a potential employer is good enough for us. Is that company good enough for your skill set? Will they complement your interests and talents and boundaries? Will they stretch you and develop you in the areas you need and want? Interviewing is a two-way street and negotiating is not giving away your skill set.
Perfect Your Elevator Pitch
Elevator pitches must be a few things: clear, compelling, concise and pithy. You literally have seconds to introduce yourself, explain what you're doing, and tell your audience why they should care. Talk confidently about who you are, what you're talented at, and how that/those talents could benefit your audience. I worked with an amazing coach, Suezette Robotham at Go Higher and Hire LLC, to craft mine because the language is so specific. I'm a huge fan of soliciting help with these types of things - résumés, cover letters, and LinkedIn pages as well - because first impressions are priceless!
Be Mindful Of Your Audience
I always tell the women at my Leap Luncheons and who I interact with in general to be discerning about with whom they discuss their ideas, wins and plans. Not everyone knows how to support us when we win, especially when our victories don't look like what everyone else is doing. Things like starting a new business, pursuing a second career or starting over in a new industry can look very scary to people for whom that is not their purpose. Very often it isn't that they aren't happy for us, but their fear -- founded in their desire that we succeed and their love for us -- ends up looking like disdain or even envy or judgement. Be thoughtful about who you share that information with and show grace to friends and family who don't respond in the way you expected.
Sometimes it isn't that they aren't happy for you, it's that they love you so much that they don't know how to show anything but concern.
Featured image by Getty Images
Brittney Oliver is a marketing communications professional from Greater Nashville. Over the past three years, Brittney has built her platform Lemons 2 Lemonade to help Millennials turn life's obstacles around. Her platform is known for its networking mixers, which has brought over 300 NYC young professionals, entrepreneurs, and creatives together to turn life's lemons into lemonade. Brittney is a contributing writer for Fast Company and ESSENCE, among other media outlets.
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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I'm Thrilled That Ryan Destiny & Keith Powers Are Back Together. 5 Things Before Reuniting With Your Ex, Tho.
Listen, as someone who grew up in an entertainment home and also as someone who got my start as a writer in the entertainment industry, I will be the first to recommend that you not get too invested in celebrities. No matter what you see in the media, you don’t really know them (unless you actually do) and that’s enough of a reason to not get super caught up in whatever it is that they’ve got going on.
However, at the same time, as with all things humanity, something that I look for when it comes to famous folks is consistency — and that is why, every once in a while, I will shout a person or a couple out, specifically. Today, it’s actors Ryan Destiny and Keith Powers. Why? Well, you caught the headline. I recently read (and then found a clip of what I read) that Ryan went on record saying that after three years of she and Keith being apart (shucks), they are back together (yay!) — and dammit, you would’ve thought that I was their blood auntie for real when she shared the news.
Video Credit: @rydersxsourc on TikTok
Why the need for such unspeakable joy? LOL. I love — love, LOVE — Black love, so we can start there. They’ve always come across as genuine BFFs and I’m a huge advocate of that when it comes to romantic dynamics. Then there are some things that Ryan said about why they decided to become an official couple again that inspired me to do what I try to do whenever I write on anything celebrity-related: tie in a lesson for the rest of us to apply to our own daily lives.
You know, someone once said that getting back with an ex is like hopping out of the shower and putting your old underwear back on. And while that is, without question, a semi-grossly graphic cautionary tale to consider — LOL — at the same time, I don’t think that it’s a one-size-fits-all resolve.
If you and an ex are dancing around the idea of giving it a go one mo’ time again, I just want you to strongly consider five things first. Just so you can be sure that there are some new-in-real-time benefits that come with getting that old thing back.
Do They Complement Where Your Life Is…Now?
Credit: @jenniferhudsonshow on TikTok
Okay, so when it comes to all of the video posts throughout this, I am sharing each one by strategic design because I am actually going to use certain things about Ryan and Keith’s life to illustrate my points. First up: Did you notice all that Ryan has already accomplished in just 30 years of life? And y’all, she has gotten back with Keith in the midst of all that is currently on her plate. This means that not only is she making time for the relationship (what we value, we MAKE time for), it would appear that she doesn’t feel like he or the relationship would be a hindrance to all of her plans, her goals — her purpose.
Currently, I (yes, personally) know someone who is a celebrity in her own right. She is trying to make something work out with an ex — only there are red flags galore. One of them is the fact that, although he says that he is in support of her career, he makes unrealistic demands on her time, and he stresses her out when it comes to where he thinks that he should currently fall on her list of priorities right now and he likes to pull semi-passive aggressive stunts in order to get her attention. Thing is, back when they were dating years ago, she was in a different season, so there wasn’t as much going on as she has now.
And sadly, as much as she doesn’t want to accept it, although they may still love each other — or they’re addicted to the feelings of nostalgia which can seem like love sometimes — they don’t really complement each other’s lives or lifestyles. There are things that he wants that she cannot provide (yes, literally) and there are things that she needs that he doesn’t seem very good at adapting to. And so, for them to try and make things work in this season, it would be a literal disaster. So much writing is already on the wall to prove it.
Five years ago, when I wrote, “If He's Right For You, He Will COMPLEMENT Your Life” for the platform, a part of the reason was because complement is a word that I bring up a lot when dealing with dating couples who are thinking about taking things to another level.
To complement is to help to complete in the sense of adding to your life, bringing balance to your world, and enriching you. If you can’t say this, with your entire self, about you and your ex — both directions, I might add — it’s not time to get back together. Whether that’s now or ever…in the wise words of DeBarge, time will reveal.
Does the Universe Seem to Be a Fan of the Idea?
Video Credit: @xmood.editss on TikTok
The Alchemistis one of my favorite books. No question. My brother introduced me to it many years ago. Anyway, the author is Paulo Coelho and one of the quotes from the book is also a fave of mine: “When you want something, all the universe conspires in helping you to achieve it." Okay, did you peep what Gabrielle said on a damn press junket about Keith and Ryan — A PRESS JUNKET?
Y’all, not everyone is going to have the kind of love story where everyone in their life is on board with them being together. I counsel folks like this and they have still had a strong relationship in spite of it. Oh, but when others admire the connection? When they see your dynamic as a standard? When those you care about can get with what you are doing and rally behind it? That is something that is beyond precious and is definitely a huge green flag. So, definitely keep this point in mind.
Moving on, if you’ve been consistently reading my content long enough, you know that me and my first love, chile — me and my first love…CHILE. LOL. Just over Super Bowl weekend, a guy he grew up with was still being a hype man for us. In fact, in a prior convo, he said something that really stayed with me: “It wasn’t until I got with my fiancée that I understood how a man could love a woman like [insert my first love’s name here] loves you.”
Listen, I wrote an entire article about why there is no need to chase anything in this life (check out “Chase Nothing, Sis: Why The Things You Want In Life Don’t Require A Chase”). Sometimes, just like with the perfect chocolate chip recipe, you’ve got to accept that you can’t do time’s job. Cookies need to sit in the oven and sometimes “the universe” needs to do its thing and fit other puzzle pieces together — ones that you don’t have access to.
However, another great indicator that you and your ex might need to consider taking another shot at love is if it seems like things are coming (back) together, without you having to do so much work — or is it toiling? — to make it happen.
Are You Both on Damn Near the Exact Same Page?
*Side note: I just adore this exchange between Keith and his dad*
My mother has always called me her “signs and wonders” child and so, it is totally on-brand for me to look at this and wonder if a part of the reason why Keith was so drawn to acting is because it was a “puzzle piece” in connecting him to Ryan — because y’all, if this does indeed work out in a jump the broom sort of way, it’s a reminder that one of the biggest decisions you will EVER make in life is who you are going to do life, for the rest of your life, with.
That said, though, the reason why this clip is relevant to this particular point is because, well, you heard what Keith’s dad said that Keith said, right? “If your heart is in it, you are going to give your all.” AND — AND YES, I AM YELLING THIS — IF YOU ARE ABOUT TO EXTEND THE TIME, EFFORT AND ENERGY TO SPIN THE BLOCK AND GET BACK WITH AN EX…BOTH OF YOU BETTER BE PREPARED TO GIVE YOUR ALL.
Because truly, why in the world would you return to something that you’ve already experienced and half-step it? That’s completely insane.
And honestly, I think that’s what’s up with me and my ex: we really just need to get married or leave each other alone and I think he knows what I deserve (yes, am qualified for) on the marriage tip. Am I waiting on him in the meantime? Nope. Not at all. Is the door completely shut, though? Due to my own convictions about the covenant of marriage, honestly, only if he gets married would that be the case (and it would be shut forever, even if he got a divorce).
However, we’re not on the same page right now because we’re not doing what Keith is talking about: giving our all. Either direction. We’re living our lives. You can love someone and still live your own life (someone needed to hear that).
And perhaps — I don’t know but perhaps — that is why Keith and Ryan broke up in the first place: because, indeed, it is an act of love to release someone when you know that you either can’t give them what they want or you don’t want the same things that they do.
Anyway, again, if you’re considering getting back with your ex, casually dating seems a bit ridiculous. Didn’t y’all already do that? It’s time to discuss if you both want the same things, at the same time now. If yes, awesome. If not, well — officially getting back together could prove to do more harm than good. Maybe it’s time to not write another chapter and just find another book (if you know what I mean).
Okay, so I went to see the movie The Fire Inside which is the true story of female boxer Claressa Shields. I salute Ryan because she was really, really good in it. Aight but what does this clip from her press run have to do with today’s topic? For starters, if you’ve followed Ryan’s career for a while, you know that she is very thoughtful and intentional about the roles that she plays. And, although, in many ways, she and Keith are pretty private about their relationship, when they do speak on it, it seems as if the same point applies.
They seem to want to be friends, they seem to want to be each other’s support system, and they seem to want to see each other win. They choose to have that kind of dynamic. Can you and your ex say the same thing? Not one or the other — both of you. Not back in the day…right now?
Next up: She said she believes that she possibly spoke The Fire Inside role into existence. Even Scripture says that death and life are in the power of the tongue (Proverbs 18:21) — and you know what? Find me one clip where Ryan was wearing Keith out after they broke up or where Keith was telling all of her business when things ended. Even in the break-up, there was integrity.
Uh-huh. Let’s not act like there aren’t several other celebrity couples who seemed to go on press tours just to dog out their ex — and somehow, they ended up back together. Still, doesn’t it seem like you could trust someone so much more if you ended things “clean”? Aren’t you far more open to considering reuniting with an individual who “covered your character” even when the two of you were apart?
My point? Before getting back together with your ex, how did you break up, how did both of you handle the ending of the relationship and, along with feeling like you love each other, can you honestly say that you both respect (and respected) each other too — in words and in deed?
Speaking things into existence? Sometimes, the way we handle things of our past shows that we can be trusted for them to re-enter into our present. Words to live by.
Are You Not “Forcing It” to Happen?
So, according to YouTube, this clip was six years ago — and the way that Keith’s face lit up when he spoke of Ryan then — Google him; he has the same energy when being in her presence now. And as we wrap this up, although I kind of touched on this when speaking of my own ex, it’s worth really honing in on: if you’re trying to force you and your ex to get back together, you probably shouldn’t be.
Ain’t it a trip how Keith said that first they met, then they casually chatted on social media, then they would spontaneously hang out, and then things transitioned into something more? No pressure. No Old Testament scroll of demands and expectations. No drama. Just vibes. LOL. Awesome.
I can’t tell you how many times someone has told me that they were thinking about getting back with an ex and — it all just seemed so stressful. She was telling me all of what he would need to do to prove himself. He would tell me all of the reservations that he still kind of had. Both of them would keep bringing stuff from the past up. This? This is what it looks like when you’re trying to force a past relationship to happen again.
What Ryan and Keith seem to speak on is, that although they weren’t “official” for a while, they were still friends — and just like how they smoothly moved into a relationship in the beginning, it would appear that they smoothly moved into getting back together as well. Y’all, if you are going to get back with your ex, it shouldn’t wear you out to do it. Breaking up was hard enough. Getting back together shouldn’t be. Feel me?
____
Although I do think that a lot should be seriously considered when getting back with an old flame, I’m definitely not totally against it. Like I said, Ryan and Keith are back together, and I think that is a beautiful thing.
When it comes to your own life, though, just make sure that if you are going to bring your past into your present that it shows many signs of blessing and not cursing your future. These five signs, hopefully, will help to bring clarity to that. Because if you’re going to be with your ex again — it needs to be a good thing…the right thing. Not just something to do…again.
I’m pretty sure that Ryan and Keith would agree.
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Featured image by Emma McIntyre/Getty Images for ELLE