What It Takes to Stay Funny When Life Isn’t I Comedian Ola Dada I Sky Talks Podcast W/ Jessa Sky #12

What It Takes to Stay Funny When Life Isn’t I Comedian Ola Dada I Sky Talks Podcast W/ Jessa Sky #12

Growth does not always look deep and serious. Sometimes it sounds like laughter, a little chaos, and conversations that catch you off guard with how real they get. It often starts in unfamiliar spaces, where identity is shaped between cultures, expectations, and experiences that do not quite match up. There is no clear blueprint in the beginning. Just trying, adjusting, and figuring things out while holding onto stability and still feeling pulled toward something more. Choosing the creative path rarely makes sense on paper, but it keeps calling anyway. Along the way, perspective shifts. Ideas about money, success, and self-worth start to look different. It becomes clear that even the people who seem established are still learning as they go. Confidence builds slowly through showing up, doing the work, and trusting the process before the results show. In this episode of Sky Talks, Jessa sits down with Nigerian-born comedian Ola Dada for a conversation that moves between humour and real-life moments. What starts as light banter opens into honest talks about identity, money, and building a life on your own terms. They talk about growing up between cultures, leaving stability, and choosing a creative path without clear guarantees. The conversation also touches on how people view success, self-worth, and the reality that most are still figuring things out. At its core, this episode shows how humour can create space for honesty, connection, and moments that leave people feeling lighter. Topics Covered: (00:00) Welcome to Sky Talks (01:45) Introducing Ola Dada and stepping into the spotlight (03:10) From accounting to comedy: choosing a different path (07:30) Rethinking money, value, and survival (10:58) Moving to Vancouver and starting again (13:02) The high of performance and the quiet after (15:20) The work behind the moment on stage (18:02) Identity and how people label others (20:14) Honest take on hometown culture (23:02) Life experiences that build resilience (24:43) Conflicting online wellness information (25:53) Staying grounded under pressure (28:05) Responsibility to calm the room (30:08) Stage anxiety vs setup stress (31:29) Mental health and emotional intensity (34:00) Past jobs and survival work (35:31) Creative work is nonstop (44:30) Bias shaped by perception and media (47:00) Upcoming comedy special (50:20) Have a relationship with Jesus (51:21) Inner work first, success follows (51:57) Comparison kills progress About the Guest: Ola Dada is a Nigerian-born comedian whose journey is shaped by a life of cultural contrast, constant movement, and learning how to connect quickly with different rooms. What began as adapting to new environments and finding humour in everyday moments grew into a stand-up style rooted in honesty, relatability, and light-hearted observation. His story reflects the steady work of turning lived experience into comedy, using perspective, timing, and presence to bring people together through laughter.  Connect with Ola Dada: Web: ⁠https://www.oladada.com/⁠ [https://www.oladada.com/] IG: ⁠https://www.instagram.com/showtime.dada/⁠ [https://www.instagram.com/showtime.dada/] About the Host: Jessa Sky is a proud Métis Cree singer-songwriter, mental health and addiction awareness advocate, keynote speaker, and the host of Sky Talks Podcast. Her career continues to rise, but her path has also been shaped by personal battles with mental health and healing. These experiences inspire her to create music, conversations, and spaces that remind others they are never alone. Through her voice, whether in song, on stage, or behind the mic, Jessa brings healing and humour together. She offers connection, breaks stigma, and shows that resilience can grow even from life’s hardest seasons. Connect with Jessa Sky:  Website: ⁠https://www.jessasky.com/⁠ [https://www.jessasky.com/] Facebook: ⁠https://www.facebook.com/jessaskyy/⁠ [https://www.facebook.com/jessaskyy/] Instagram: ⁠https://www.instagram.com/jessaskyy/⁠ [https://www.instagram.com/jessaskyy/] TikTok: ⁠https://www.tiktok.com/@jessaskyy⁠ [https://www.tiktok.com/@jessaskyy] YouTube: ⁠www.youtube.com/@jessaskyy⁠ [http://www.youtube.com/@jessaskyy]

How Spray Tanning Became a Lifelong Calling I Spray Tanning I Sky Talks Podcast W/ Jessa Sky #11

Purpose is often not discovered in comfort. It is shaped through lived experience, discomfort, and moments that force change. It begins when something happens that makes a person stop and see life differently. What was once normal no longer feels right, and there is no way to go back to how things used to be. In this episode of Sky Talks, Jessa sits down with her close friend Kelsey of SprayTansYeg for a conversation that goes beyond surface-level transformation. Kelsey shares how her business began from a turning point that forced her to reevaluate her health and direction, followed by years of steady commitment where belief had to come before results. Together, they explore the real cost of growth, outgrowing people, trusting your intuition, and accepting that not everyone will understand your choices.  Topics Covered: (00:00) Welcome to Sky Talks (00:20) Introducing Kelsey of SprayTansYeg (02:20) How SprayTansYeg turned a skin scare into a spray tan career (10:52) The discipline of staying when nothing is working yet (15:18) Boundaries, trust, and vulnerable client care (23:37) Why consent matters in vulnerable client care (25:18) Over 100+ spray tans and the reality of repetition (29:08) Education over fear-based marketing (33:00) When accountability meets emotional honesty in friendships (39:59) Boundaries evolve at every stage of life (41:45) Trusting your intuition in relationships (45:50) When friendships stop feeling safe or supportive (50:24) Being misunderstood in relationships (54:15) Coming out of isolation and reflection (55:52) Closure is an evolving experience, not a final answer  (58:58) Does every ending need a conversation (01:01:18) The cost of allowing the wrong people in (01:04:31) Creating a life your children do not have to recover from (01:06:37) Show up despite uncertainty in business and life  (01:11:00) Overcoming fear of judgment  (01:14:28) Social media can distort real life (01:16:20) When social media starts to feel toxic (01:20:40) Taking up space & being yourself online  (01:22:10) Wedding Fair & Small business hustle  (01:24:40) The power of a spray tan routine  About the Guest: SprayTansYeg is an entrepreneur whose journey started from a turning point in her health and personal life. What began as a practical step grew into a business built through consistency, patience, and self-trust. Her story reflects the quieter side of growth, learning to listen to your body, trust your direction, and keep showing up even when results are not immediate. She shares a grounded perspective on resilience, shaped not by big moments, but by small, intentional decisions over time. Connect with SprayTansYeg: Web: https://www.kajaglow.com/ [https://www.kajaglow.com/] FB: https://www.facebook.com/profile.php?id=100063679226858 [https://www.facebook.com/profile.php?id=100063679226858] IG: https://www.instagram.com/spraytansyeg/ [https://www.instagram.com/spraytansyeg/] TikTok: https://www.tiktok.com/@spraytansyeg [https://www.tiktok.com/@spraytansyeg] About the Host: Jessa Sky is a proud Métis Cree singer-songwriter, mental health and addiction awareness advocate, keynote speaker, and the host of Sky Talks Podcast. Her career continues to rise, but her path has also been shaped by personal battles with mental health and healing. These experiences inspire her to create music, conversations, and spaces that remind others they are never alone. Through her voice, whether in song, on stage, or behind the mic, Jessa brings healing and humour together. She offers connection, breaks stigma, and shows that resilience can grow even from life’s hardest seasons. Connect with Jessa Sky:  Website: https://www.jessasky.com/ [https://www.jessasky.com/] Facebook: https://www.facebook.com/jessaskyy/ [https://www.facebook.com/jessaskyy/] Instagram: https://www.instagram.com/jessaskyy/ [https://www.instagram.com/jessaskyy/] TikTok: https://www.tiktok.com/@jessaskyy [https://www.tiktok.com/@jessaskyy] YouTube: www.youtube.com/@jessaskyy [http://www.youtube.com/@jessaskyy]

The Work of Caring Without Losing Yourself I RN Tara I Sky Talks Podcast W/ Jessa Sky #10

Not every kind of healing looks obvious. Sometimes it looks like finally paying attention to the things you’ve been brushing off for years. The exhaustion you keep pushing through. The discomfort you’ve normalized. The habits, insecurities, and little frustrations that slowly become part of your everyday life. In this episode of Sky Talks, Jessa sits down with her friend and trusted injector, RN Tara of Absolute Aesthetics, for an honest, hilarious, and surprisingly deep conversation about beauty, healing, confidence, and what it really means to care for people well. They share Jessa’s experience with filler, Botox, dissolving, and facial symmetry, and why more is not always better. The conversation also covers Tara’s work in nursing, burnout, mental health, women’s wellness, IV therapy, and vitamins. This episode is for anyone who has ever struggled with body image, overdone beauty standards, exhaustion, self-neglect, or simply wants to feel better from the inside out. Topics Covered: (00:00) Welcome to Sky Talks (01:21) Introducing our guest, RN Tara (03:22) Jessa’s filler journey and what went wrong (06:19) How Jessa and Tara met (07:10) Why safe care matters (10:26) Less is more in aesthetics (12:08) Building trust before treatment (13:47) Tara’s experience in nursing and the OR (20:26) Why feeling cared for matters (24:18) You never know what someone is carrying (25:37) Boundaries, empathy, and protecting your energy (39:40) Staying professional in crisis care (42:28) De-escalation is part of care (48:59) Nurturing others while learning to nurture self (51:43) Turning aesthetics into healthcare guidance (53:23) What IV therapy can help with (57:35) Transparency, pricing, and trust (01:00:08) The unexpected path to becoming a nurse (01:04:03) Growth happens in discomfort (01:10:40) Why filler isn’t one-size-fits-all (01:16:36) Honesty about risks in aesthetic treatments (01:21:13) Skin, acne, and real-world factors affecting results (01:24:35) The gap between how people look and feel (01:26:06) Showing up for each other in hard moments (01:31:06) Raising children without bias (01:33:35) Identity, individuality, and freedom (01:35:05) Unity, respect, and shared humanity (01:36:48) Connect with Tara About the Guest: RN Tara is a registered nurse and the founder of Absolute Aesthetics, where she combines medical knowledge with a thoughtful, patient-centered approach to beauty and wellness. With nearly two decades in nursing, she brings a grounded perspective to aesthetics, IV therapy, vitamins, and overall well-being, helping clients make informed decisions that support both confidence and health. Her work is rooted in care, education, and creating a space where people feel comfortable, supported, and seen. Connect with RN Tara / AbsoluteAestheticsEdmonton:Web: https://absoluteaesthetics.ca/ [https://absoluteaesthetics.ca/] FB: https://www.facebook.com/AbsoluteAestheticsEdmonton [https://www.facebook.com/AbsoluteAestheticsEdmonton] IG: https://www.instagram.com/tara_the_aesthetician/ [https://www.instagram.com/tara_the_aesthetician/] YT: https://www.youtube.com/@tara_the_aesthetician [https://www.youtube.com/@tara_the_aesthetician] About the Host: Jessa Sky is a proud Métis Cree singer-songwriter, mental health and addiction awareness advocate, keynote speaker, and the host of Sky Talks Podcast. Her career continues to rise, but her path has also been shaped by personal battles with mental health and healing. These experiences inspire her to create music, conversations, and spaces that remind others they are never alone. Through her voice, whether in song, on stage, or behind the mic, Jessa brings healing and humour together. She offers connection, breaks stigma, and shows that resilience can grow even from life’s hardest seasons. Connect with Jessa Sky:  Website: https://www.jessasky.com/ [https://www.jessasky.com/] Facebook: https://www.facebook.com/jessaskyy/ [https://www.facebook.com/jessaskyy/] Instagram: https://www.instagram.com/jessaskyy/ [https://www.instagram.com/jessaskyy/] TikTok: https://www.tiktok.com/@jessaskyy [https://www.tiktok.com/@jessaskyy] YouTube: www.youtube.com/@jessaskyy [http://www.youtube.com/@jessaskyy]

The Messy, Brave Process of Letting Go and Rebuilding I Indiginize Creation I Sky Talks Podcast W/ Jessa Sky #9

A lot of people think healing looks soft, quiet, and put together. Like you wake up one day and everything just makes sense. But the truth is, healing can be loud. It can be messy, emotional, and uncomfortable. It asks you to face what hurt you, to tell the truth about what happened, and to finally choose yourself. Growth does not always look like peace at first. Sometimes it looks like walking away from what you once prayed for. It looks like setting boundaries, even when it’s hard. It looks like rebuilding your life while still grieving parts of it. And somehow, through all of that, you start to come back to who you really are. In this episode of Sky Talks, Jessa Sky sits down with Janelle of Indiginize Creation for a conversation that is raw, unfiltered, and deeply real. They talk about sisterhood, social media connections that turn into real-life bonds, and the journey of reconnecting with culture. Janelle opens up about leaving her marriage, breaking cycles of trauma, and finding healing through her art, powwow dancing, and community work. It’s honest, emotional, and a reminder that you can rebuild your life and still become something even stronger than before. Topics Covered: (00:00) Welcome to Sky Talks (00:20) Introducing our guest, Indiginize Creation (03:43) How social media built real-life sisterhood (07:10) Identity struggles: not fitting in anywhere (10:12) Dealing with judgment and negativity (16:47) Wanting softness after always being “the strong one” (17:49) The “perfect” relationship lie (21:40) Walking away and choosing self-worth (25:35) The trauma stops with me (27:15) Healing isn’t pretty—and that’s the point (31:17)  You can be struggling and still show up (37:21) Quitting everything to bet on her own art (42:36) Your art doesn’t have to fit one identity (45:46) A simple hello bridges the gap (49:50) The danger of putting people on a pedestal (51:34) Turning pain into purpose by helping others (55:29) Honor your roots through your work (59:30) Choosing healing and freedom (01:00:52) Building new life, new circle, new connections (01:03:36) Not everyone deserves access to you (01:05:03) Save your energy for what matters (01:06:26) Choosing a smaller circle (01:08:03) Rejecting gossip (01:09:15) Upcoming events and where to find Janelle About the Guest: Janelle, the artist behind Indiginize Creation, is a powwow dancer, cultural educator, and entrepreneur creating one-of-a-kind, hand-burned designs rooted in identity and storytelling. Through her work, she blends artistry with purpose, using each piece to reflect culture, healing, and personal expression. Beyond her craft, she leads workshops across communities, sharing knowledge about Indigenous culture, mentorship, and self-discovery. With honesty and heart, she speaks on resilience, breaking cycles, and the journey of finding strength in both tradition and truth. Connect with IndiginizeCreation:  Website: https://indiginizecreation.ca/ [https://indiginizecreation.ca/] Instagram: https://www.instagram.com/indiginize_creation/ [https://www.instagram.com/indiginize_creation/] Facebook: https://www.facebook.com/profile.php?id=100092263208640 [https://www.facebook.com/profile.php?id=100092263208640] About the Host: Jessa Sky is a proud Métis Cree singer-songwriter, mental health and addiction awareness advocate, keynote speaker, and the host of Sky Talks Podcast. Her career continues to rise, but her path has also been shaped by personal battles with mental health and healing. These experiences inspire her to create music, conversations, and spaces that remind others they are never alone. Through her voice, whether in song, on stage, or behind the mic, Jessa brings healing and humour together. She offers connection, breaks stigma, and shows that resilience can grow even from life’s hardest seasons. Connect with Jessa Sky:  Website: https://www.jessasky.com/ [https://www.jessasky.com/] Facebook: https://www.facebook.com/jessaskyy/ [https://www.facebook.com/jessaskyy/] Instagram: https://www.instagram.com/jessaskyy/ [https://www.instagram.com/jessaskyy/]

Chaos, Courage, and the Work of Being Seen I Callmekeeks I Sky Talks Podcast W/ Jessa Sky #8

Speaking openly about the realities behind creative work is not always comfortable, but honesty can help people better understand the systems artists move through every day. Humor often makes difficult conversations easier to hold, especially when the topics involve identity, community, and public visibility. Many performers experience a gap between how they are treated on stage and how they are treated off stage. A person can be applauded during a performance and still face judgment or dismissal in everyday spaces. Recognition does not always translate into respect, and that contradiction can shape how artists move through their work and their communities. In this episode, I speak with Call Me Keeks, a multidisciplinary performer and member of the House of Ebony, Alberta’s first all-Black queer and trans performance house. We talk about leaving corporate work to focus on performing, the realities of working in the arts, and the importance of community. Keeks also shares experiences from the performance scene, reflections on leadership and accountability, and thoughts on protecting creative energy while continuing to grow as an artist. Topics Covered: (00:00) Welcome to Sky Talks (01:18) How Jess and CallMeKeeks first met (03:33) Edmonton snow removal and city frustrations (05:05) Child welfare system failures and racism in social work (08:51) Who is CallMeKeeks?  (12:22) “Connoisseur of Chaos”  (15:26) Preparing for performances and off-stage judgment (19:40) Indigenous erasure and Black overexposure (22:45) Seeing the wrong people get the opportunities (25:36) Refusing abuse and setting boundaries (27:44) What good producers do differently (31:15) Ego, leadership, and accountability in the industry (34:42) The importance of a trusted inner circle (37:17) Social media perception vs. real life (40:00) Living through a tense political and social climate (41:34) Personal growth, healing, and building a better life (43:21) Self-worth beyond productivity (45:22) Authentic content and TikTok culture (47:02) Healthy relationships require mutual respect and not settling (53:16) CallMeKeek’s story of meeting her fiancé (58:43) The risks of advocacy in creative industries (01:00:58) Have trusted people who keep you accountable (01:01:50) Mentoring the next generation (01:03:49) Respect in community without needing friendship (01:07:23) Future plans for the House of Ebony About the Guest: CallMeKeeks is a multidisciplinary performer, burlesque artist, and community advocate with over 20 years in the performing arts. She is the auntie of the House of Ebony, Alberta’s first all-Black queer and trans performance house. Through her work she celebrates creativity, challenges systems, and uplifts marginalized voices. Known for her humour,  honesty, and “connoisseur of chaos” energy, Keeks brings bold storytelling and unapologetic authenticity to every stage and conversation. Connect with CallMeKeeks:  Instagram: https://www.instagram.com/callmekeeks_/ [https://www.instagram.com/callmekeeks_/] About the Host: Jessa Sky is a proud Métis Cree singer-songwriter, mental health and addiction awareness advocate, keynote speaker, and the host of Sky Talks Podcast. Her career continues to rise, but her path has also been shaped by personal battles with mental health and healing. These experiences inspire her to create music, conversations, and spaces that remind others they are never alone. Through her voice, whether in song, on stage, or behind the mic, Jessa brings healing and humour together. She offers connection, breaks stigma, and shows that resilience can grow even from life’s hardest seasons. Connect with Jessa Sky:  Website: https://www.jessasky.com [https://www.jessasky.com]  Facebook: https://www.facebook.com/jessaskyy [https://www.facebook.com/jessaskyy]  Instagram: https://www.instagram.com/jessaskyy [https://www.instagram.com/jessaskyy]  TikTok: https://www.tiktok.com/@jessaskyy [https://www.tiktok.com/@jessaskyy]  YouTube: www.youtube.com/@jessaskyy [http://www.youtube.com/@jessaskyy]