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The Lifecycle of our Careers Reflections from a Seasoned Planner

By: Chriss Holloway | Dec 3, 2025

As the year tilts toward winter and the calendar fills up one more time, I find myself thinking about what it means to be not just an experienced planner but also an “aging planner” in the meetings and events world. After nearly thirty years in this industry, I feel like I am in a new season of my career (dare I say it…likely the last!). It is a season that is deep in colour and experience, but it also comes with a little chill of change.

In July, I started a new role at the age of 52. It has been incredibly energizing and humbling. For the first time, I am often one of the oldest people in the room. The energy, creativity and innovation around me are contagious. At the same time, I would be lying if I said I did not feel a quiet pressure to prove that experience still matters, especially when it comes to technology, social media and content creation.

I often turn to AI as my quiet tutor, helping me learn the programs and tools my younger colleagues seem to navigate without thinking.

The View from Experience

When I asked other seasoned planners to share their thoughts through a short survey, their responses felt very familiar. Most have been in the industry for 30 to 40 years. Nearly all of them pointed to technology as the single biggest shift they have lived through.

We have moved from triplicate typed docs, fax machines and photocopiers to registration platforms, analytics dashboards and AI-driven everything. Alongside that change is a stronger focus on strategy. Events now need a clear purpose and measurable outcomes, not just flawless logistics.

One planner summed it up nicely: “Technology is by far the most significant change, but so is the focus on being strategic about the purpose and desired outcomes of planned events.” That mix of tools and intention has completely changed how we plan, deliver and evaluate our work.

The Challenge of Staying Current

The hardest part for many has been the speed of that change. “Keeping up with new technology” showed up in response after response, closely followed by “the pace and workload.” One planner said that trying to stay current with social media felt like “trying to keep up with something that never stops moving.”

Several respondents also talked about ageism, and the quiet assumptions that come with being an older professional in a tech-driven world. As one put it, “Ageism is real. There is a stereotype that we are not familiar with technology.” Another added, “Technology has taken some of the personalization and hospitality out of the business. Hospitality is not just about loyalty points and metrics.”

I feel that tension too. We want to embrace digital tools and smart systems. At the same time, we want to protect the warmth, connection and hospitality that drew so many of us into this profession in the first place.

The Value of Experience

The good news is that the survey also revealed a strong sense of quiet confidence. Experience brings a calm that you cannot download.

“The knowledge a mature planner brings to the table, combined with new tech, is powerful,” one person wrote. Another said their greatest strength was being able to “pivot when technology crashes,” because they have already lived through every kind of crisis.

Experience lets you see the bigger picture. It helps you anticipate issues, manage expectations and stay calm, cool and collected when everyone else is on edge. That steadiness, and the ability to make clear decisions under pressure, is still one of the most undervalued assets in our industry.

Sustaining Energy and Purpose

I was curious about how people stay excited after so many years because, honestly, I’ve struggled with this. The answers were encouraging.

“Every event I do is different from the last. That keeps me on my toes,” one planner shared. Another talked about continuous learning, especially outside the industry, as a way to bring fresh ideas and perspective back into their work.

Some told me that their role has naturally shifted over time. “As my career progressed, I found myself drawn to the big picture,” one respondent said. “Thinking strategically, how can we be more efficient, how can we stay aligned as a team, gave me greater purpose.”

That resonates with me. Earlier in my career, I loved pulling off the impossible and the challenge of thinking WAY outside the box. Now, the real satisfaction comes from helping others do that and knowing I played a part in setting them up for success.

Passing the Torch

Mentorship was a major theme that came through in the survey. Many described it as a two-way exchange. They learn from younger colleagues, especially when it comes to tech and new trends, while offering guidance and reassurance that comes from years of experience.

“Mentorship is not just about giving advice,” one planner wrote. “It is about being present, engaged and supportive.”

That is exactly how I see it. At this stage of my career, I do not feel the need to be the loudest voice in the room. I would rather help create a space where others feel comfortable speaking up, trying new things and trusting that they will be supported.

Facing Change with Grace

Some of the planners I heard from are already in retirement / semi-retirement, choosing projects that truly interest them. Others have no plans to slow down. Either way, there was one common thread in almost every response: stay curious.

“Investing in staying abreast of the latest developments is essential,” one participant wrote. “The landscape is changing faster than ever.”

That curiosity, and that refusal to quietly check out, is what defines the aging planner for me. We are not fighting change. We are learning how to evolve with it, and sometimes even lead it.

This Season of Our Careers

If early career is spring, full of possibility, and mid-career is summer, busy and bright, then this stage is when experience shows its boldest colours. The roots are deep, the view is wide and the lessons are a lot easier to see.

We may move a little slower at times (all those early years running events in heels probably did not help), but we move with intention. Our value lies not only in what we know, but in the way we share it. The next generation brings fresh ideas, energy and skills. The aging planner brings the context, the perspective and the calm to help those ideas land.

As our industry races into its next season, we are not on the sidelines. We are mentors, collaborators and storytellers, bringing years of experience into whatever comes next.

 
 Article edited by: Darlene Kelly-Stewart, Stonehouse Sales & Marketing Services

 

Author

CH
Chriss Holloway
Manager, Conferences & Events at Children’s Healthcare Canada

 
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