
Issa Rae On Having Multiple Streams Of Income: 'Because, Why The F*ck Not?'

A good sis recently filled me in on the dangers of only having one hustle and I was quickly forced to reevaluate all of my life choices.
While I'm a jack of many trades, I've discovered that I haven't given myself the opportunity to be lucrative at more than one at at a time and if my one stream of income were to magically dry up, all of my other material assets would quickly evaporate into thin air and I would be out here looking crazy AF.
The truth is, no matter fat the check may be, your bag is never truly secured if you only have one source of income, but in a recent interview with Billboard, Issa Rae let us in on the secret to leveling up your business acumen and creating generational wealth: ownership. That's it. That's the whole secret.
For the past 365 days, Issa has been booked, busy, and serving up big boss energy with her latest business endeavors. Along with collaborating with LA-based creatives to open a coffee shop in Inglewood, Issa also invested in a streaming analytics business and launched a recording label, giving the term #NoDaysOff a whole new meaning, but her motivation behind all of her hustles is a desire to level up her equity. She explained:
"That's a huge part of being able to have longevity — to have a stake in your own career is to own your masters. I understand, especially when you become fucking Taylor Swift, you want some sort of ownership over your work. But coming from the TV side, I don't own 'Insecure'. HBO owns that at the end of the day. I have to have my own distribution arm to be able to own my work. I think now artists are so much more hip to the fact that 'Oh, I don't ever have to sign with anyone unless I absolutely need the money,' and even then it's easier to negotiate."
When it comes to managing multiple streams of income, The Photograph actress says that her most important tool has been knowledge, most of which she acquired on the internet. Issa explained that like most entrepreneurs, her hustle came out of a sense of necessity and today, she attributes her choice of becoming a boss to her not having a reason *not* to.
"Even from a young age, my mom used to call me bossy. Only now do I realize that I wanted to be that. I wanted to be a boss because, why the fuck not? I liked feeling like I was working or in business. I liked feeling like a leader. And it is not always fun, by any means, but there's an element of accomplishment that I feel in executing projects."
Issa told Billboard that ultimately, her mission is to become a boss ass hybrid of Oprah, Diddy, and Ellen, who are all inspirations to the 35-year-old producer in their own right:
"I always say that I model myself after Diddy, Ellen and Oprah: Oprah for being able to diversify her businesses and being a major influencer in that way; Ellen for being able to make a business out of being herself; and Diddy for his business acumen in expanding beyond hip-hop. I've looked to them in terms of ways to make my own imprint."
Read the full article here!
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Taylor "Pretty" Honore is a spiritually centered and equally provocative rapper from Baton Rouge, Louisiana with a love for people and storytelling. You can probably find me planting herbs in your local community garden, blasting "Back That Thang Up" from my mini speaker. Let's get to know each other: @prettyhonore.
'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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Why You Should Strongly Consider Premarital Counseling BEFORE Getting Engaged
It was the social commentator Will Rogers who once said, “All television is children’s television.” What he meant by that is TV has a way of “dumbing you down,” if you’re not careful. He ain’t neva lied either because, y’all, there is truly an endless amount of diabolical foolishness in all mediums of the media these days; especially when it comes to the tube (well, and social media). And so, I must say, for that reason alone, I am grateful for programming like OWN’s Family or Fiancé.
As a marriage life coach for over 20 years at this point, I’m sure that I’m a little bit biased when I say that I appreciate the overall premise of the show because (if you haven’t seen it) it’s (mostly) about engaged couples, their potential red flags, and their loved ones holding them accountable to those things before they attempt to jump any broom — and boy, if there is something that I wished happened more often, off-screen, it’s exactly that.
That’s not to say that there aren’t times when I find myself hella triggered while watching the program, though. I say that because I literally can’t believe some of the issues that continue to exist (BIG ONES) after someone has proposed and their partner has accepted. Financial drama. Family drama. Distrust. Toxic levels of communication. Sometimes stuff that makes you wonder how and why a couple are friends let alone engaged to one another. SMDH.
Yeah, as I recently said in a podcast interview not too long ago, I really wish that marriage therapists, counselors, and life coaches would normalize recommending premarital counseling to people before anyone puts a ring on someone else’s finger. I say that because, as someone who wholeheartedly believes that there would be a lot less divorces if premarital counseling was so much more thorough than it tends to be, I also think that if two people really pondered if they should even get engaged to begin with…there would be more solid marriages between individuals who are good fits for one another instead of fleeting weddings between two people who really had no idea how deep marriage is.
And so, as unconventional as it may be, today I’m going to make my case for why, anyone who is considering marriage up the pike, should get into premarital counseling BEFORE a ring is bought, anyone gets on one knee and definitely prior to a wedding date being set.
Premarital Counseling Should Not Be Treated Like a Mere Formality
Someone in my world right now is engaged — and I’m not thrilled about it. They are super young, hella broke and there is a lot of drama going on between both sides of their families. When I spoke to the bride-to-be about the importance of getting some premarital counseling, I thought that I was going to throw the phone across the room when she shared with me that they were going to go for “a couple of sessions.” Chile, with all that she shared with me, they need to be in counseling for at least six months (more on that in just a sec) and yet, she said that the pastor that she was speaking with thought that 2-3 meetings would suffice.
Umm…in what world? You can’t even get to the root of why there is so much contention with the family members in a couple of sessions and they have a whole lot more red flags waving than that. And yet, sadly, we’ve gotten so used to premarital counseling being seen and treated as nothing more than a mere formality that it’s not really taken seriously — and that can prevent engaged couples from taking what they are about to get into as seriously as they should as well.
And don’t get me started on how true this is once you’ve already got a ring on your finger because there’s a really big chance that you are going to move forward with your wedding whether counseling goes well or not — if for no other reason than your pride doesn’t want people to know that you called your engagement off (check out “These 12 Women Broke Off Their Engagements. Here's Why.”).
And that is reason #1 why I think that premarital counseling needs to happen before an engagement — because 1) you can take your time because there is no wedding to plan for yet and 2) you don’t have to worry about what you should do about your engagement if you realize you shouldn’t be together…you’re not engaged yet. Moving on.
Premarital Counseling Should Be More than a Couple of Sessions
Clients of mine who have plans to get married can vouch for the fact that if you’re going to work with me, don’t book a first session if you want to get married within a couple of months. Shoot, I tend to spend 5-6 sessions on intimacy alone because it’s important to discuss things like what you were taught about sex, how your first time impacted you, if you are a virgin what inspired the decision, what your expectations of sex are, how religion has influenced your views of sex, how you prioritize sex in a marriage, what you think the purpose of sex actually is — and that’s actually just the tip of the iceberg!
And since there is so much more that comes with being married than just having a healthy sexual dynamic (although that is easily in the top five if you understand the purpose of sex in a marital union), how can three 30-minute sessions even begin to scratch the surface?
Have mercy, y’all, with the divorce rate still hovering somewhere around 50 percent, statistics revealing that couples who engage in premarital counseling are typically able to reduce their chances of ending their future marriage by a little over 30 percent, it’s almost tragic that reportedly only 36 percent of couples go premarital counseling, to begin with.
And if you want to go the distance of what most people vow (which is a promise) during their wedding ceremony of being together until death parts you — how in the world can you prepare for that without getting as deep and detailed as possible about things like: your childhoods; your communication styles; your values; your future plans and goals; your emotional needs; your sexual desires; your vices; your strengths and weaknesses; your expectations; how you handle money; your (potential) deal-breakers; your parenting styles; the baggage that you carry from past relationships; your boundaries with family members and friends; how you plan on dealing with holidays and special days; how you handle disagreements; if your home is going to be traditional or not; if your home is going to have Scriptural standards or not; who is going to clean what; who is going to handle what — need I go on to prove that a couple of sessions simply ain’t gonna cut it? I doubt it.
Premarital Counseling Before Engagement Takes the Pressure Off…to Get Married
Semi-recently, while at a funeral, I ran into a guy who I hadn’t seen in, shoot, at least 15 years. As we were walking to our cars and catching up on our lives, I said, “I have always meant to tell you that you and your ex-fiancé have always been heroes of mine.” They’ve been broken up even longer than the last time I saw him and so, understandably, it took him a minute for him to even get where I was coming from. “Oh, [insert her name here]? Why do you say that?”
My reason is because they actually attended a church in Nashville that does what I believe: that you should participate in premarital counseling before getting engaged. Anyway, although he and his girlfriend actually “passed” the counseling process, they ended up breaking up anyway. I remember, even back then, him saying that after they really considered all that comes with making a marriage work, they came to the conclusion that they weren’t each other’s best complement (check out “If He's Right For You, He Will COMPLEMENT Your Life”). GOOD FOR THEM.
Yep, another reason why I’m a huge fan of premarital counseling happening before getting engaged is because I think that most people will listen better to what is being said to them if they took this approach. They will really stop to consider if they should even go from dating (or boyfriend and girlfriend) to getting engaged — because (and it can’t be said enough) I need everyone to remember that by the time you are someone’s fiancée, all that means is you two are in a season of preparing for your wedding day. Engagement is not about seeing if you need to get married or not. IF YOU DON’T KNOW THAT, YOU DON’T NEED TO BE ENGAGED (YET). AND YES, I AM YELLING THAT.
And if you’re in premarital counseling, not engaged and you see that you would be better off not becoming spouses, then there is no pressure to get married. Because you are not fiancé and fiancée. You are seeing if that should even happen…and it tends to be a lot less stressful to admit that it shouldn’t when you’re not at the point of being officially engaged…yet.
Premarital Counseling Can Save a Lot of Money (in the Long Run)
I have this theory that easily 80 percent of the married couples who ended up getting a divorce, a part of them wanted to call off the wedding the night before. Why didn’t they do it? For the same reasons why some of the members of my own family didn’t (and honestly should’ve and ultimately ended up divorcing anyway): venues were already paid for; dresses were already purchased; deposits were already put down; plane tickets were already bought, family members already have non-refundable investments — in folks’ minds, it’s simply too late to not go through with it.
Listen, if you think that being in a miserable marriage or getting divorced is easier than calling off a wedding, I don’t know who told you that lie. Besides, even if it is a little embarrassing, it actually takes a lot of courage to declare that you respect the covenant and contract of marriage too much to go through it just because you want to avoid feeling uncomfortable for a little while or you don’t want to lose money that you’ve already spent.
And yet — imagine how much this all would totally be a non-issue if you never spent any money in the first place (engagement ring included) because premarital counseling prior to getting engaged revealed to you that there is no need to plan a wedding because either you’re not with the right person or it’s not the right time? The investment in counseling prior to getting married may cost you a grand or so (give or take) and yet it’s still gonna be cheaper than paying for a wedding — one that very possibly shouldn’t be happening in the first place. And that will preach.
Premarital Counseling Should Focus on Different Things than Engagement Counseling
Unpopular (or at least uncommon) opinion: premarital counseling and engagement counseling should be separate. While premarital counseling should be all about figuring out if the person you’re thinking about marrying someday is an ideal fit for you, engagement counseling should be about providing tips and tools to make your wedding planning and newlywed years a smoother transition. Because, although we live in a culture that thinks a lot like my 13-year-old goddaughter does (that there isn’t much of a difference between a boyfriend, fiancé, and husband), people who are dating are not nearly as serious as people who are engaged and people who are engaged are not nearly as serious as people who are married.
Each season of a relationship comes with its own weight of responsibilities and while being in a long-term relationship, you should explore if you and your partner should shift into considering marriage, once you have declared that you are suitable for one another (which is what engagement is about), it’s well past time to be out here trying to figure out if you should get married…now it’s time to figure out how to do it. BIG DIFFERENCE.
So yes, I think it would be a total game-changer, indeed, for more therapists, counselors, and life coaches to encourage premarital counseling (should we get married?) to people who are (seriously) dating and engagement counseling (we need tips for preparing for our wedding and transitioning into becoming newlyweds) to those who are actually engaged.
If steps were taken in this fashion, I definitely think there would be fewer daters wasting each other’s time, more engaged people focusing on what the engagement season is truly all about — and both would take the importance of marriage counseling more seriously and literally as well. Because something else that research reveals is that 90 percent of married couples who attend 90-minute sessions, once a week, for 10 weeks, report that it ended up improving their emotional well-being and 75 percent said that the sessions made them feel more satisfied with their relationship overall.
Counseling does that. Counseling does that.
Just sayin’.
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