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Dear Judy and Linda: Embrace Intergenerational Collaboration for Digital Confidence in Midlife!

picture of linda and judy

Welcome back to our career advice column series, “Dear Judy and Linda.” This week, we're diving into a topic many women in their 40s, 50s, 60s, and beyond tell us is challenging: feeling like you need to keep up with the latest technology trends.

Picture this: you’re an accomplished professional, respected for your experience and expertise. However, as technology rapidly evolves, you’re starting to feel left behind, struggling to keep up with younger colleagues who seem to navigate the latest tech tools and trends effortlessly. 

We get it. Digital literacy is increasingly valued in the workplace, and feeling technologically outmatched can lead to feelings of inadequacy.

The situation can feel even more isolating when you consider turning to younger, more tech-savvy colleagues. Imposter syndrome sets in, and you might feel uncomfortable admitting you need support.

And yet, the workplace doesn't wait for anyone, and staying relevant in the digital age is essential for career longevity. 

What’s the solution? This week, we respond to a question from Tanya, who faces a similar challenge at work. We’ll share strategies to connect with your younger colleagues rather than feeling like you need to compete with them.

So, grab your coffee, and let’s go!

You’ll take away a gem of wisdom for feeling more confident navigating the workplace in midlife! 


Dear Judy and Linda,

I'm a marketing director in my 50s. More than ever, technology is playing a significant role as everything is digital. Lately, I've been feeling a bit insecure because many of my younger colleagues seem to have a stronger grasp on the most recent tech-related matters than I do. 

It's not that I'm unwilling to learn, but sometimes, given my other responsibilities, I just can't keep up. How can I overcome this feeling of inadequacy and bridge the gap with my younger coworkers in a way that fosters collaboration and mutual respect?


Tanya, W.


Dear Tanya,

First of all, know you're not alone in feeling this way. The rapid pace of technological advancement can be daunting for anyone, regardless of age or experience. Let’s take a moment to celebrate your win!  Your willingness to address this challenge head-on is impressive and sets a positive tone for building bridges with your younger colleagues.

One practical approach is to embrace a growth mindset and view your younger coworkers not as competitors, but as valuable resources for learning and collaboration

Don't be afraid to ask questions or seek their expertise when navigating tech-related tasks or projects. Many younger colleagues are eager to share their knowledge and skills. When you ask others for help, you give them an opportunity to let their strengths shine! 

And it’s not a one-way street. You have experience and expertise to share, too. Intergenerational collaboration deepens mutual understanding and fosters meaningful connections at all levels of the organization. 

Take advantage of training programs or resources offered by your company or free resources online to enhance your tech skills. Demonstrating a can-do attitude sends a powerful message to your colleagues that you're committed to staying relevant and contributing to the team's success.

Remember, even if it doesn’t always feel this way, diversity in age, experience, and skill sets is a strength in any workplace! 

By embracing your unique perspective and actively seeking opportunities to collaborate with your younger colleagues, you'll bridge the generation gap and enrich your team's collective knowledge and capabilities.

Bonus tip: take time to assess your strengths, opportunities, and where you need to skill up. Download EvolveMe’s Career SWOT tool! 

To your success,

Linda and Judy


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