Issa Rae Explains Why She’s Happy Her Success Came Later In Life
Actress, writer, and producer Issa Rae highlights the advantages of achieving success and fame later in life and showcases how the timing has uniquely enriched her journey.
The 38-year-old, who has been involved in the entertainment industry for over a decade, captivated fans' hearts in 2011 with her comedy web series The Misadventures of AWKWARD Black Girl, which she created and starred in. Although the series and the book of the same name earned Rae recognition, the star's career would elevate to new heights in 2016 with the release of her hit HBO series Insecure.
The show lasted for five seasons and ended in 2021. Since then, Rae has starred in countless films, including Spider-Man: Across the Spider-Verse, the live-action Barbie, which has generated $1 billion at the box office, and created another HBO series Rap Sh!t.
In a resurfaced Masterclass video, Rae revealed why she was grateful that her accomplishments in the entertainment industry happened when she turned 30 while uplifting others still attempting to accomplish their goals by sharing stories of different celebrities who have succeeded at an older age.
Issa Rae On Why She Feels It's Never Too Late To Become Successful
In the clip shared on Masterclass' official Instagram page in July, The Photograph star disclosed that there is no timeline to start working on a particular goal.
Rae added that she felt that way because of the stories she heard of individuals, including actor Morgan Freeman and director Ava DuVernay, learning more about their craft and pursuing that career later in life.
"I don't think it's ever too late to get started. There's too many stories of people learning and getting their opportunities later," she said. "People like Morgan Freeman, who started late, and I think about Ava, who didn't pick up a camera until her mid-30s."
Issa Rae On Achieving Success In Her 30s
Further, into the conversation, Rae shared that she was "thankful" that her show Insecure was "greenlit" when she was 30 because she would have negatively impacted the experience.
"My show didn't get greenlit until I was 30. I'm thankful for that. Because I always say if I had started to pop in my early 20s, I would be out here hoeing," she stated.
Rae wrapped up the discussion by reminding her fans that although they too may be in the same situation, they shouldn't let that moment define who they are.
"So maybe it's good that you're popping later. You're more mature, and this doesn't define you," she said. "[It] doesn't define who you are, and I do feel I have more sense of self because I started later. Because I knew I really wanted to do this."
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'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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This Is What It Really Means To Heal Your Relationship With Money
Riddle me this: If money were your partner, what kind of relationship would you be in?
Would the relationship be one that's supportive and secure? Would it be built on things like trust and mutual respect? Or would it be more like a rollercoaster, varying between hot and cold, stressful, ridden with anxiety and insecurity? For a lot of us, the parallels might be parallel-ing, as the relationship we have with money mirrors some of the same unhealthy patterns we’ve had in romantic ones: fear of abandonment, emotional avoidance, lack of boundaries, or the belief that we have to earn our rest, ease, or abundance.
Now, I've read enough of The Psychology of Money to know that our relationship with money is an emotional one. So, it's not just about what you make or how you spend, it's about how money makes you feel. And like any relationship in your life, if you're not paying attention to the emotional patterns controlling your reality, money can quickly become a source of shame, anxiety, stress, or self-sabotage. This is why healing your relationship with money has to start within.
That's something Sasha Suresh knows firsthand. As the founder of Jolii Cosmetics and Full Ritúal, an award-winning wellness brand, she’s built a 7-figure business rooted in soulful alignment, intention, and yes, financial abundance. But it didn’t begin there. Now through her 1:1 coaching and signature course The Million Mastery Method, Sasha teaches women how to rewrite their money stories, shift out of survival mode, and reclaim their power.
“There have been key moments when I realized that money wasn’t just about numbers,” she shares. “It was deeply connected to how I saw myself.”
For Sasha, that turning point was recognizing how financial anxiety was showing up as a mismatch between the value she created and what she believed she deserved to receive. “I also saw that the more money I made, the more fear I had about losing it all and the need to be wanting more and more. This recognition marked the beginning of my journey to heal and redefine my relationship with money because money is essentially just energy and should be viewed as just that. Money is the means for us to do other things and it is not the end all be all.”
Unpacking What's Holding You Back
A lot of us are carrying hidden beliefs about money we don’t even realize we’re repeating. These money beliefs might sound like:
- “Money is hard to come by.”
- “More money means more problems”
- “I’m not good with money.”
- “I'll be paying back this debt forever.”
- “I’ll never make more money.”
And while some of those beliefs may seem harmless or even rational depending on your financial situation, Sasha explains these are signs of unhealed money wounds. “There are so many signs indicating an unhealthy relationship with money and most of the time these go unnoticed because we’re so conditioned to see them as the norm and they’re a part of us,” she says. “I used to have major financial anxiety where even small financial decisions would cause me stress or I would be swiping my cards like there was no end to it. There was no in-between. My financial decisions were dependent on my emotions which can be very detrimental in the long run.”
She continues, “The tendency to undercharge for your services or accept a lower pay than what you truly deserve is a sign that your inner narrative about worth is still catching up with your actual value. And the most common of all might be avoidance – steering clear of detailed money management because it brings up old, unresolved feelings.”
At the root of it all? An unhealthy relationship with money and a nervous system that had learned to equate money with fear.
Where It All Begins
Oftentimes, our relationship with money is shaped long before we ever earn our first paycheck. In fact, our relationship with money tends to mirror what we saw while growing up from our parents or what we've experienced through societal conditioning. “If you grew up in a home where money was a source of stress or secrecy, you might carry invisible beliefs like ‘I need to suffer before I can succeed’ or ‘My value is tied to how much I earn,’” Sasha says.
She notes that many of us have internalized the idea that wealth must come through sacrifice, hustle, or even through compromising our morals. In some communities and cultures, money can even be viewed as a source of corruption.
“This conditioning often leads to cycles of overworking, guilt when money flows effortlessly, or self-sabotage to return to the 'comfort' of scarcity. We’re taught that success must be earned through hardship, so you might dismiss opportunities that feel joyful or aligned as 'not real work,'” she explains. “These narratives can create subconscious resistance to abundance, where earning more triggers guilt rather than celebration.”
Healing Your Money Wounds
Healing your relationship with money isn’t about making dramatic shifts overnight. It's about becoming aware of your wounds, knowledgeable of your patterns, and living a life more aligned with a different belief system that is rooted in feeling worthy, feeling safe, and allowing flow.
Below, Sasha shares some of the most common money blocks she sees in her coaching work, and how to begin healing them:
1. Scarcity Thinking
One of the biggest blocks to abundance is the belief that "there's never enough." A scarcity mindset creates a loop of anxiety that leads to clinging to every dollar like it's your last, rejecting opportunities even when there's alignment, or constantly feeling like you're behind in life even though you're right on time. “Your scarcity script writes your reality,” she explains. “If you narrate limitations, your world shrinks to match exactly that.”
She encourages shifting this mindset by asking yourself: What if I acted like abundance is already here? Making aligned decisions from that place can be transformative.
2. Fear of Success or Rejection
Sometimes, the fear isn’t about failing, it’s about what might happen if you succeed. You may wonder if more money will change how others perceive you, or worry that you’ll lose yourself in the process. “This fear often manifests as procrastination, undercharging, or downplaying wins,” she says. A helpful shift is to start celebrating through what Sasha calls “micro-victories.” “Each celebration rewires your nervous system to associate success with safety, not threat.”
3. Undervaluing Yourself
If you constantly discount your services or avoid negotiating your worth, that’s usually tied to deeper beliefs around not being deserving. “If you don’t feel deserving, you’ll leak wealth everywhere—discounting services, tolerating underpayment, or avoiding negotiations,” Sasha echoes.
“Your self-image becomes your financial ceiling,” she explains. She recommends tuning into where your resistance is coming from. Try writing “I am worthy of abundance” ten times slowly, really feeling each word. Notice what emotions or discomfort come up. That’s where your work begins. As Sasha says, this is where your inner narrative about worth can catch up to your actual value.
4. Emotional Avoidance
If you're prone to avoiding money altogether, i.e. skipping bills, ignoring your budget, avoiding your bank account balance, or pushing off conversations about finances altogether, these could be signs of deeper unresolved feelings or shame.
To begin healing, Sasha suggests starting small and approaching money from a place of compassion rather than resentment. Acknowledging your finances through intentional money management, even if it’s just for a few minutes a day, is a powerful first step toward creating a better relationship with money.
How Healing Your Money Mindset Creates Space for Growth
Healing your relationship with money doesn’t just change how you manage it, it changes how you show up. Sasha knows this shift well. As a wellness founder and the creator of the Million Mastery Method, her business began to grow in new ways when she did the internal work around her money story.
“When you begin to see money as a tool rather than a source of anxiety, your decision-making improves. This is exactly what happened for me in my business – as I shed my limiting beliefs around money, I became more authentic in my interactions with clients and partners,” she says. That clarity translated to more ease, more aligned clients, and more income, without the burnout or over-giving she once defaulted to.
“When you’re not battling internal money anxieties, you have more mental and emotional energy to dedicate to creative and strategic endeavors. This increased focus opened so many doors for me without me chasing them,” Sasha explains. “With a healed money mindset, setbacks become lessons rather than confirmations of scarcity. You’re more resilient and adaptive, which is essential for long-term business success. Your business starts to feel like an authentic extension of who you are, leading to a deeper sense of fulfillment and sustainable growth.”
So, Where Do You Begin?
According to Sasha, the first step in healing your relationship with money doesn’t begin in your bank account, it starts in your body. It's about shifting the way you feel about money before you ever shift the actual numbers. “Start by envisioning and feeling what financial abundance looks and feels like, and let that inner truth lead you in making decisions,” she says. That vision can be as simple as imagining yourself feeling safe while checking your bank account, confidently setting your rates for your services, or tipping without hesitation.
These small but powerful acts create new emotional pathways that support the idea that money is not something to fear, instead it’s something you can trust yourself to handle. “When you align your inner world with the abundance you desire, every single aspect of your life changes,” Sasha explains. “From the way you price your services to the opportunities you attract.”
Anything worth having doesn't come easy, and that goes double when it comes to inner alignment and getting your relationship with your money right. Sasha is honest about this and the discomfort that sometimes arises as we heal, our money wounds included. “Things will get uncomfortable and may not come to you naturally,” she says, “but just know that getting to the other side of your fear, self-sabotage, and anxiety means you’ve reached your desired state—which is a state of ease, flow, and abundance.”
That’s what financial healing really is: a reclamation of your sense of safety, your self-worth, and self-trust. It’s a recommitment to self-belief. When you start showing up as the version of yourself who believes she is worthy of wealth, aligned decisions and opportunities begin to follow. You no longer have to force abundance, it starts to meet you where you are because you already are.
“Embrace this inner transformation,” Sasha encourages, “and you'll find that financial healing becomes a natural extension of your newfound self-belief.”
Money, after all, isn’t inherently good or bad. “It’s energy that reflects your boundaries, your self-worth, and your vision,” she reminds us. “You don’t have to choose between wealth and integrity. When you align money with your mission, you step into your power.”
Love is cute and all, but building an empire together? That’s the real flex. Tap into our new series Making Cents to see what financial compatibility really looks like when love and legacy go hand in hand.
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