What It Actually Cost Me to Build This Business

Jessie Khaira didn’t just build a business. She built it while navigating grief, pressure, and life-changing moments behind the scenes.

In this episode, Jessie continues her story and shares what was really happening as her business started to grow. From leaving a job that was emotionally draining, to attending her first industry conference during one of the hardest moments of her life, this is an honest look at what it takes when there’s no structure, no boundaries, and no pause.

She also opens up about the realities of saying yes to everything, underpricing her work, difficult client experiences, and the personal toll it all took, including how it impacted her marriage and her health. This is the part of building a business that most people don’t talk about.

Chapters

00:00 – Picking up where the story left off
01:30 – Leaving her previous career
03:00 – The moment everything changed before her trip
05:00 – Showing up while grieving
07:00 – What she learned at her first conference
09:00 – Expanding without structure
11:00 – Creating opportunities from nothing
13:00 – Working with venues and early business growth
15:00 – Pricing mistakes and absorbing costs
17:00 – A client experience that changed everything
19:00 – The reality of being overworked
21:00 – How business impacted her personal life
23:00 – Pregnancy, complications, and still working
25:00 – Running a business from a hospital bed
27:00 – Why she kept going no matter what

Submit a question, story, or topic for the podcast HERE

Connect with Jessie

Website: www.jessiekhaira.com

Instagram: @jessiekhaira

If you are planning a South Asian wedding, supporting someone who is, or working in this space as a planner, this podcast was created for you. Hit subscribe and join the conversation as we plan with clarity, confidence, and perspective.

Transcript

SPEAKER_00 0:02

Welcome to The Planner's Perspective with Jesse Cara. This is the podcast for wedding planners and couples navigating South Asian weddings and everything that comes with them: culture, family dynamics, money, design, expectations, and the real conversations no one prepares you for. I'm Jesse Cara, a South Asian wedding planner and educator, stressed by couples and families when things get complicated. Here we go beyond timelines and interest boards and talk about what actually happens behind the scenes. If you're a planner stepping into South Asian weddings or a couple who wants to understand the process more deeply, you're in the right place. Let's get into it. Welcome back to The Planner's Perspective. I'm Jessie Cara, award-winning South Asian wedding planner and designer. In the last episode, I walked you through how this all started. Not with the plan, not with strategy, but with chair covers I made for my own wedding and a decision to try and make my money back. What I didn't understand at the time that I wasn't just starting something small. I was stepping into something that was going to grow faster than I was ready for and bigger than I ever imagined. Because while things were picking up, there was still no structure behind it. I was saying yes to everything, adding services as I went, figuring things out in real time, and building something without actually stopping to define what I was building. At the same time, my life outside of the business was shifting too. I had moved from full-time to part-time in my role in recreational therapy because I couldn't handle the emotional toll anymore. I'm an empath, as I mentioned, and I was carrying everything home with me. It was affecting me in ways I didn't fully understand then, but I knew I couldn't keep going like that. So I left. And I started working full-time at a courier company instead, which gave me structure during the day. But everything else, my evenings, my weekends, my energy, went into the business. That became my routine. I would work during the day and then go straight into setups. Client calls, like prep work, late nights, and very, very full weekends. I slowly let go of the makeup as well, not because I didn't enjoy it, but because it was taking up time that I needed to grow the decor side of the business. Every decision I made was based on where the demand was and where I could make more money, even if I didn't fully understand what that meant long term. But I knew one thing very clearly. I did not know enough. And that's what led me to my very first conference. I was 25 years old, traveling out of Canada for the very first time by myself, going to a wedding conference in California. I was nervous, I was excited, and I remember feeling like this was a big step for me. Like I was finally doing something to take this seriously instead of just reacting to whatever came my way. We were back living with my in-laws at the time, and I was getting ready to leave for the airport, saying goodbye to my mother and father-in-law, holding on to that, like that mix of fear and excitement when the home phone rang. And my mother-in-law answered it, and then she turned to me and passed me the phone. I remember that moment so clearly. Like it's happening right now. I took the phone and it was my foford, my uncle. And he said hi. And without any sort of preparation, without any sort of warning, he told me that my aunt, my judge, passed away. This wasn't an aunt in the traditional sense. Uh, she was one of my mom's friend's daughters who married into our family, and I had a very close relationship with her. I lived with her for years. We shared a room. She was a part of my everyday life growing up. Like, she's the reason I permed my hair, started like threading my eyebrows, even though my mom and dad were so against it. She literally brought me so much joy. And in that moment, my heart shattered. I remember leaning against the wall, and then I was on the floor. I don't remember the exact moment I went from standing to sitting, but I remember the feeling. I remember my body couldn't hold me up anymore. I remember sitting on that floor just trying to process what I had just heard. My parents were in India, my brother was in India, she was in India, her son was there too. A child I practically raised, and I was here. And I wasn't gonna say goodbye. I wasn't gonna have the chance to say goodbye. I remember wailing, but not crying quietly, not trying to hold it all together. I remember wailing. The kind of pain that feels like it's coming from somewhere so deep and you can't control it. I couldn't speak. I don't even remember hanging up the phone, but I think my mother-in-law took it and asked what happened. And then a few minutes later, I wiped my tears. I packed my car and I went to the airport. I didn't know what else to do. I didn't know it sounds how it sounds, but I wasn't thinking, I wasn't processing, I was hollow, like completely hollow. But I did what I had always been taught to do, and that was to keep going. I showed up to that conference like that. Um I didn't socialize, I didn't network, I die, I didn't try to put myself out there. I I stayed to myself and I decided to just that I was gonna learn, that that's what I was there for, and I was gonna learn and during the day that's what I did. And when I got back to the hotel room in the evenings, I would cry. That was a tough few days. Because even in that state, I knew that I needed something from the rooms I was entering. But what I found there wasn't what I expected. There weren't classes on decor the way I thought there would be. There wasn't like nothing about chair covers or centerpieces or the things I had been focused on. It was about planning, the coordination, structure, lighting, food displays, how events actually function behind the scenes. And something shifted in me. Because for the first time, I started to understand that what I was doing was only one piece of something so much bigger. Up until that point, I had been focused on what things looked like, what I could provide, what I could physically deliver. But this opened my eyes to how things like how everything connects, how timing matters, flow, how decisions impact each other. And with that, precious moments event coordination and design was born alongside Elite Chair covers. Not as a clean transition, but as a and like not even as a rebrand, but just something I added on because I still wasn't letting anything go. I was just adding more. When I got back from that conference, I realized I didn't have a portfolio that reflected what I knew I was capable of. So instead of waiting for clients to give me that opportunity, I created it myself. I would set up full displays in our basement apartment. I would practice, I would style tables, test different looks, play with layouts, and then take photos. So I had something to show. And because of my hair and makeup experience, I didn't even make my cousins get dressed up to be my client. Okay. It wasn't glamorous, it wasn't a studio, it was a basement, but I showed up and I practiced anyway. And at the same time, things started shifting in the business. I got a contract with a rental company to handle all of their chair cover orders. Then I started working with banquet halls that had purchased their own chair covers, and I would provide sashes based on their clients' theme colors. And over time, that led me to becoming the in-house decorator at a banquet hall. And at that time, that felt like the big moment. It felt like stability, consistent work, being part of a venue instead of chasing every booking. But this is also where I learned some of my hardest lessons. The venue would take bookings and payments and then pay me. And sometimes clients would come to me directly because I had an office right downstairs and would like book me directly and then I would pay the venue a referral fee. And something I stand by even now is that I didn't feel right increasing my prices to account for those commissions. It didn't feel good to pass that cost on to the client, so I didn't. I absorbed it. I thought I was doing the right thing, but what I actually was doing was making my business harder to sustain. I was working more, taking on more responsibility, but not structuring my prices in a way that supported the growth. And then there were the clients. There was one client. Uh, I had done like two previous events for her, and now I was doing her like daughter's wedding. I did two house decor setups. I did a backyard party like in lieu of a reception. And then I had done their Jagu, like Singe at the hall. And they were happy with everything. Like everything seemed to have gone well. Like when we went to go do the teardown, like they were happy. There was no major issues, or so I thought, there was one little detail. At the venue towards uh by the dance floor, there was like two sets of steps. And they had wanted um these decorative pieces, like at those steps, like a little juggle gurvey thing, if you know what that is. But it's just like a decorative piece. Now, altogether, there was two steps, so we would need four of those pieces. But if I placed something on the lower one, that would be a trip hazard. So I made a judgment call and instead of placing on all four steps, I only placed them at the top because I didn't want anyone getting hurting. Uh hurting. I didn't want anyone tripping or getting hurt. I didn't clarify that decision. And those two pieces of decor, like literally the rent, I was renting them for like $10 or $11. So like $20 altogether became the reason I was not paid. They had only paid me a 25% deposit on all of the events. And then they were supposed to pay me when I went to go set up the house decor. And they had family guests and they were busy and they're like, We'll pay you after, but that never happened. And then, like, as I said, like when we went to go take it all down, she was like, Yeah, this is great. But then she stopped answering my calls. Then she, like, when I went to the house, oh, we have guests, and then they just stopped opening the door, like, just completely ghosted me, but then called the venue and said she was not going to pay me the rest of this money. I was so frustrated and I was angry and confused. Even now I don't understand. Like, I would understand taking out a little bit, but I do I still don't understand not paying. But also, I am like such a believer of karma and like just energy. And I think, why would you want your child's marriage to start with that kind of energy to screw over someone's like bread and butter and not give them thousands of dollars over 20 bucks? But that moment taught me something I didn't fully understand at that time. But not everyone operates the way you do. And if you don't communicate clearly, you leave room for things to go wrong. And at the same time, my personal life was starting to feel the impact of everything I was building. I was working constantly, like legit, back to back. And while other people had like weekends and date nights, I was doing setups, going home to nap, and sometimes not even going home, just going to my parents' house because it was like that's where I had inventory downstairs. It was four minutes from the hall that I was doing these contracts at. So it just made sense. But it's just, yeah, because there was always something going on, and my business had become my sole source of income at this point. So I was just always gone and my marriage became rocky. Um, I was not present. I was just pushing forward. I was just doing what I always thought I had to do. And underneath all of that, I was pregnant. I truly believed I could manage everything, that I could keep working at the same piece, pace, keep saying yes, keep showing up the way I had been, and it would all just work out. So I cleared six weeks before and after my due date because I thought I was being responsible. I thought I had planned for it. But my pregnancy had complications. Um, due to how much I was working and not taking care of myself and eating and drinking enough. I definitely was not drinking enough water. I ended up being induced at 33 weeks. I remember being in the hospital and having the pastor come in and talk to me, preparing me for the possibility of a stillborn. That isn't a conversation you expect to have. They gave me steroids to help develop my daughter's lungs. And while all of this was happening, I was still running my business. I was lying in a hospital bed talking to my mom and my cousins through the jobs I had that week. I had my daughter on a Friday, and while my mom, like at the same time, like as I'm going through labor and delivery, my mom was at the hall overseeing the setup, and I remember telling my cousins to just give the client whatever extras, but just to keep her happy. So there I was in labor running a business, not knowing if my baby was going to make it. The nurse didn't believe me when I said I was my baby was coming. When they had checked me, I hadn't dilated enough, but I didn't want a C-section. And I started doing the hypnobirthing I had learned, and I knew I was ready. But by the time the doctor came in, everything escalated quickly. My daughter Jeeven had been in the birth canal for too long. She told me to like push. And as she's telling me to push, she's yelling at the nurse, saying, You've like put this baby in jeopardy, and yeah, like just reminding her that I was high risk and the baby was premature. And when Jeevin was born, she was taken straight to the NICU. There was no skin to skin, just like they just wanted to make sure she was okay. Yeah, that was a crazy day. And I remember after Jeevin was born, that was like she was born at like 12 something in the afternoon. And at two, the bride's mom had come to check up on the hall. And she goes to my mom. She's like, Well, where's Jessie? And the mom's like, She just had a baby. And so my mom calls me, and this lady takes the phone and she was like, What are you doing? You should have told us. I'm like, No, everything was fine. Like, this happened out of anywhere I didn't want to stress you out. But they were so grateful, like, just so grateful and so happy with everything. Yeah, so I've I've had both ends of the spectrum. But yeah, so on the Monday, I discharged myself. I did not have a choice. It was against like the nurse at the hospital who I was under, and the doctor were just like, no, we need you to stay. But I had a wedding, 90 days out. Uh, so Tuesday was Canada Day, and I had a wedding, and so I discharged myself and I went to work. And also, Jeeven came before the six-week window of when I had booked time off. So I didn't truly have a choice. Like, I did not have enough time to get somebody else prepared when we had already like done all the legwork. So I kept going. I showed up, I worked because I thought that's what it takes. And looking back now, I see things very differently. But at that time, for me, that was normal. This is what I believe building something required. And that belief is what shaped everything that came next. I'll see you in the next episode. If today's episode helped things click or gave you a new perspective, make sure you're subscribed so you don't miss what's coming next. This podcast exists to support planners in doing their best work and to help couples feel informed, confident, and prepared as they navigate their very own Celtage and wedding. If there's something specific you want me to talk about, an episode idea you'd love to hear, a planning story you want to share, or a question you're sitting with, there's a link in the show notes where you can send it all in. I promise I will read every submission, and many of them will state future episodes. You can connect with me at www.justycara.com or on Instagram at JustiCara. If you're ready to navigate self-station weddings with intention and confidence, I'll see you there. And if this podcast is supporting you in any way, I would truly appreciate you taking a moment to leave a five-star review. It helps more planners and couples find these conversations and keep the space growing. Until next time, trust your perspective and plan with clarity.