The Strategist's Dilemma 1: The Perfect Illusion

What you’ll learn:

This article is part of Klick’s series The Strategist’s Dilemma, in which Jason Kaminsky examines the common challenges, opportunities, and pivotal moments strategists face in their careers. Throughout this series, we’ll explore how strategists can proactively shape their own growth paths, redefine their professional narratives, and unlock new levels of impact.

I was leading strategy for a major oncology brand at a prestigious agency. Finally, I had the opportunity to immerse myself in a category I had sought out for years. I oversaw a large and talented team, had plenty of resources, and adored the people that I worked with. On paper, it looked like an ideal situation and in many ways it was.

Yet, I felt stuck. The years of market research, wild launches, and complex strategies were becoming old hat, and I found myself getting bored. And boredom is kryptonite for a strategist. I was twitching and itching for something I couldn’t articulate.

I describe the feeling as being trapped in a “gilded cage.” 

The Gilded Cage and How to Recognize It

Any strategist at any career stage can get trapped in the gilded cage. Signs and symptoms include feeling stalled, constrained, or limited by your own success despite the outward appearance of luxury.

The feelings often manifest when:

How can we move past comfort and break free, re-energize, and tap into our commitment to curiosity? I explored this topic with three strategists: Sophie Needleman, Zoie Smith, and Alicia McGrath. 

When We Outgrow Our Role

Zoie, a brilliant influencer strategist, started to feel that her specialty at a previous agency was becoming a limiting factor. 

“You can’t be a generalist without being a specialist first. Because when you really dive into being a specialist, then you start to realize… there’s so many things to dig into and ways to expand. I feel like using your specialty is a great way to become a very strong generalist.”

When We Realize We’re in the Wrong Role

Sophie, who cut her strategy teeth in oncology, began her career as a copywriter until she started listening to herself and realizing it was time for a totally new career path. 

“I started noticing that the voices I was most drawn to were the voices of strategists. When strategists would speak, I would listen in a different way. And that’s what keyed me into the fact that this was something I felt very drawn to. Being acutely aware of the things that spark joy for me, that’s what helped me make the switch from copywriting.”

When We Don’t Even Know We Are Stuck

Alicia was at the top of her game in social strategy when her manager started asking her some really thought-provoking questions.

“Once we [Klick’s strategy team] switched to hybrid, the pairing of me with my manager was really interesting because we had completely different backgrounds. By asking me questions and understanding my world, she opened the door for me to share things differently and to grow into new spaces.”

Spotting the Cage and Owning Your Career Growth

No matter how your gilded cage manifests, recognizing it is key: 

You might be in a gilded cage.

Here are some practical and proactive steps you could consider for yourself:

Regardless of the path you take, clearly communicate to your leadership your desire to explore different types of strategy to broaden your knowledge and bring more value to the team and organization. It may not happen overnight, but a truly supportive manager and team will share a genuine interest in your desire to grow.