Nice Work: Hop in, we’re taking a career roadtrip

New coach alert! 

Jen Dionisio, Transformation Coach

Ya’ll, I am so excited to announce that Jen Dionisio is joining Active Voice as a coach, with availability for new clients starting this month! 

I first met Jen years ago as a fellow content strategist here in Philly, and I was delighted when she joined the Courageous Leadership Program in its very first cohort back in 2020. When she told me afterward that she was starting coach training herself, I immediately began scheming ways we could work together. 

Jen’s focus is on helping people navigate career transitions with more authenticity and ease, and I honestly can’t think of someone better suited to the task. She’s got this incredible presence—it’s somehow energetic and calming at the same time. In other words, precisely what you need when you’re staring down a scary career choice. 

Jen’s done lots of things in her own career, from running a content strategy team to teaching college courses to working in public radio. She’s even gone to clown school (you’re gonna have to schedule a call with her to hear about that). And she brings it all to her coaching practice. 

If you’re in need of a career reset right now (and so many people are), check out the workshop Jen’s running later this month, or book a free intro session with her. And keep reading below for an interview with Jen—including her biggest advice for someone in a work slump right now.

Workshop: Reroute Your Career

Map your path to meaningful change with Jen Dionisio

March 29 from 6-8pm ET • Tickets: $97

Maybe it’s boredom. Or exhaustion. Or total disillusionment. Whatever the cause, you know your career needs to change, but you’re not sure what that means. Between doing nothing or blowing up your life, the answer is usually somewhere in the middle. And this workshop will help you find it.

Join Jen to explore the disconnect between the work life you want and the work life you have, and get support facing all those ideas and worries you’ve been avoiding. You’ll leave with clearer priorities, new inspiration, and a sense of direction.

An interview with Jen Dionisio

Sara: You specialize in coaching people through career transitions and professional identity crises. So…what’s your career story?  

Jen: I’d describe it as “happy accidents.” Like many folks, I was doing content strategy before I had a name for it. I was usually the first and only digital person in the nonprofits I worked for, so I sought as many teachers and mentors as I could outside of my immediate network. This opened my eyes to career opportunities that I didn’t know existed.

Once I finally landed a content strategy role within a tech consultancy, I realized that wasn’t the end of my story at all. Adjusting to my new environment was much harder than I expected. Within a year, I was burned out and riddled with imposter syndrome. I almost quit from the stress—but then someone recommended I work with a coach instead. 

I left that relationship transformed—and eager to help other people find the same clarity and confidence I now had. That’s when I started thinking about becoming a coach myself, though it took another year or so before I dived into formal training. There was always a reason to delay, until the start of the pandemic made it clear this wasn’t just a career interest—it was a calling.

Sara: So while you were training to become a coach, you also became a manager, right? Tell us more about that experience!  

Jen: I thought I was going to be an independent contributor forever—the emotional labor of managing a team had been too much for me in the past. But a byproduct of coaching training was that I learned to coach myself. I suddenly had tools that helped me draw boundaries, lead challenging conversations, and treat myself with the same compassion I have for others. I realized that I’d been holding myself back from doing something that brings me joy and pride because I didn’t trust myself. 

After that aha-moment, I threw my hat in the ring for a management role—and I’m so grateful I did. We scaled from 5 to 25 people that year, and experienced a ton of growing pains and identity crises as individuals and a group. Some of my proudest moments have come from helping my team work through that chaos and find a way forward.

Sara: Holy moly, that’s…a HUGE amount of growth for a year—especially in the middle of the pandemic! What has that taught you, and how does that show up in your coaching conversations now?

Jen: It firmed up a belief that’s been percolating over the years: Every time I’ve invested in myself, I’ve been paid back exponentially. That investment can be money, or time, or practice. Ultimately, it’s meant following a curiosity without a strong sense of what the outcome will be, but trusting that something valuable will come from the experiment. Even clown school—which I was interested in purely for fun!—has influenced some of the work I do with clients, particularly around role-playing worst-case scenarios and dreaded conflicts. 

I bring that spirit of “trust your curiosity” to my coaching conversations. So often career change is thought of as an off/off switch: you’re this person, doing this job, and then you’re that person, doing another thing. Then you find yourself needing to repeat the process every couple years as your circumstances and interests change. 

But the process of transitioning is much less daunting when you treat it less as strategizing your journey from point A to point B, and more as a leisurely professional roadtrip that lets you try new things, take detours when serendipitous opportunities arise, and—most importantly—rest when needed.

Sara: I love this idea of your career as a roadtrip (or maybe several roadtrips), versus a single destination we’re careening toward at top speed. If someone’s reading this and struggling to let go of the idea that they need The Answer to their career, what would you tell them? 

Jen: You don’t need to have everything figured out—frankly, that’s an impossible goal anyway! 

One of the more frustrating things about work is that so many aspects of it are out of your control to change. But starting with what you can control can open up a world of possibilities that a more traditional approach doesn’t take into account.

Likewise, the small shifts you make when trying to shift your professional identity may feel underwhelming in the moment, but they truly add up to more substantial long-term change. Often, you only get to appreciate that in hindsight. But that hindsight is always a day away!

And lastly, you are never too late, too old, too different, or too anything at all to design a work life that makes your whole life happier. There’s no starting from scratch, because your lifetime of experiences remain part of your professional story. And they often give you courage and strength in the moments you least expect them to.