From Service to Celebration: Events by Shaun Rajah

Some wedding planners arrive in the industry through their own wedding. Shaun Rajah arrived through twenty years in hotels, working his way up from the very bottom to Director of Social Catering at one of Chicago's top properties - and that background shows in every single thing he does. Based in Chicago and working across Mexico and Asia, Shaun has built a business that is deliberately, intentionally small. After spending time with his story, we at Wezoree understand exactly why.

A Career Built on a Mother's Illness, and a Realisation That Came With It

Shaun's path to founding his own company was not a straight line, and it certainly was not overnight. As Director of Catering at The Langham Chicago, he loved the work completely - the pace, the people, the events, all of it. But when his mother became ill, everything shifted. "I realized I needed more flexibility in my life - the ability to visit her, be present, and still continue doing the work I loved." The hotel, to its credit, offered him the flexibility to step away and return later. But in that period of reflection, something else became clear. "I was meant to do this. I was born to do this." He wanted to build something of his own - not just weddings, but events, corporate gatherings, private dinners, celebrations at home - with the freedom to plan with real intention and stay deeply involved in every detail.

That is also the reason his company has never grown large. "I like keeping it small. I like knowing exactly what is happening with every client and every event. I like that my clients are working directly with the owner, and I think that says a lot." For Shaun, planning is not simply about producing an event. "It is about creating something meaningful while still being present in the lives of the people I love."

What He Loves Most

"What I love most about this job is the connection." Shaun genuinely loves meeting people, learning their stories, their families, their cultures - the small details that make a couple who they are. Being part of the LGBTQ community adds a deeper layer of meaning to that work. "I think about how much has changed, and how much more will hopefully continue to change in the next ten years. I have had the privilege of creating magic and wonder for so many couples, and someday I hope I get to experience that same kind of love and celebration for myself. Until then, it is a joy and an honor to help others experience it."

Sixteen Years of Bespoke, Hands-On Planning

Shaun has been in the wedding business since 2012, and he plans fifteen to twenty weddings a year, a number that reflects exactly how involved he intends to stay with every single one. His process typically begins around a year out, though he will make exceptions for the right fit at six months. Because the company is bespoke, the extra time matters: it gives him room to truly understand the couple, their families, their priorities, and their overall vision.

He runs the business by choice as a small operation, supported by a dedicated team on wedding weekends but personally involved throughout the entire planning journey. For every client, he maintains a detailed planning document holding everything - notes, decisions, vendor updates, timelines, reminders, next steps - alongside monthly calls and recap summaries so nothing falls through the cracks. "The goal is to plan ahead so the final two months do not feel chaotic." By that stage, the major decisions should already be settled, leaving only refinement and confirmation. "A strong planning process should feel calm, organized, and streamlined. The wedding weekend should not feel like we are still figuring things out - it should feel like everything has been thoughtfully built, piece by piece, so the couple and their families can actually enjoy it."

The Real Challenge Nobody Sees

Ask Shaun about the hardest part of this work, and his answer goes straight past logistics. "One of the biggest challenges I've faced with weddings is not always the logistics themselves, it's managing all the moving pieces while keeping everyone calm." 

Weddings involve couples, families, vendors, venues, weather, timelines, cultural traditions, and last-minute changes nobody saw coming, and the real skill is making sure none of that stress reaches the people experiencing the day. "Something will always shift. A timeline may need to move, a room may need to be flipped faster, weather may change the plan, or a family request may come in at the last minute. The key is not to panic. The key is to already have options, communicate clearly, and solve the problem before it becomes visible to everyone else." This, he says, is also the part of the job he takes the most pride in - protecting the experience.

Building a Timeline That Actually Works

Shaun's approach to timelines starts the moment he is booked, growing from a simple skeleton into a fully detailed roadmap as decisions get made. "The biggest thing couples need to understand is that a timeline is not just a list of times. It has to make sense operationally." Guest flow, vendor load-in, room resets, weather contingencies, transportation, family dynamics - all of it has to be considered before a single time slot is locked in.

He is also direct about the moments when a couple's wishes bump against reality. "You may love a venue, but if the maximum capacity is 300 and you have 350 guests, it is simply not going to work." Or an outdoor ceremony without a real backup plan for rain. "Those pieces need to be thought through before making a concrete decision." A good timeline, in his words, should feel realistic rather than rushed - something that lets the day breathe while still keeping everything moving, so the couple feels present and taken care of rather than watching the clock.

What He Wants Couples to Actually Look At

Shaun's advice to engaged couples is refreshingly unconcerned with aesthetics. "Look beyond what you see on social media. Beautiful photos are important, of course, but they only show you the finished product." What they do not show is the communication, the problem-solving, the vendor coordination, the calm handling of the unexpected. Coming from the hotel world, he sees weddings through an operational lens: "A beautiful wedding is not just about how the room looks. It is about how the day flows, how guests are cared for, how vendors are managed, how quickly issues are handled, and how supported the couple and their families feel throughout the process."

His suggestion when choosing a planner: look at response rate, organisation, communication style - and talk to past clients, not just about how the wedding looked, but about how it felt to work with them. "The best compliment is not just, 'The wedding was beautiful.' It is, 'Everything felt effortless.' That effortlessness takes experience, preparation, and a planner who truly knows how to run an event."

The Venues He Knows From the Inside

Three venues sit at the top of Shaun's list, and his perspective on each is shaped by having worked inside these spaces, not just toured them as a planner.

The Langham Chicago will always hold a special place - "elegant without trying too hard," with service that genuinely sets it apart. The Drake Chicago carries a different kind of weight: "There's so much history in that building, and it has that old-school Chicago glamour that you just can't recreate." And Waldorf Astoria New York, though outside his home city, belongs on any list for the sheer sense of occasion it delivers the moment you walk in. "I look at venues a little differently because I've worked inside these spaces. I understand the flow, the service, the timing, the behind-the-scenes logistics, and whether a venue can truly deliver the experience it promises."

No Single Wedding, Many Lasting Relationships

When asked which wedding has stayed with him the most, Shaun resists picking just one. "I truly believe every couple and every wedding stays with you in a different way." He is the kind of planner who keeps in touch long after the wedding ends - texts here and there, yearly check-ins, sometimes ongoing relationships with the mothers of the bride. "What I love most is getting to know who the couple really is and then creating something that feels like them. I try not to repeat a pattern or copy what worked before." The weddings that stay with him are simply the ones that felt honest to the people who lived them.

What Makes Him Different

Shaun's perspective is shaped by a path most planners do not take. "Some planners become planners after planning their own weddings. Some are naturally creative, talented, and beautiful at what they do. My path was a little different." Twenty years in hotels taught him how venues actually operate - how kitchens function, how service teams move, how contracts work, how timing affects every part of an event. "I bring a different perspective to the table because I understand not only what makes an event beautiful, but what makes it work."

Events by Shaun Rajah is built on a philosophy that feels increasingly rare in this industry: stay small, stay personal, and never let a client feel like one name on a long roster. Shaun's hotel background gives him an operational fluency that most planners simply do not have, while his genuine love of connection ensures the experience never feels clinical. The result is a planning process that is calm by design and deeply, individually considered for every couple who walks through his door.