Megan Dalessandro, a content producer, creative director, and self-described creative Swiss Army knife, discusses the importance of creating a healthy work environment for all employees, the impact of gender roles on career progression, and practical advice for freelancers managing their finances.
Host Kaila Sachse also speaks with Meg Dalessandro about the challenges of balancing a career and personal life. Meg shares her journey of navigating career setbacks, redefining success, and finding a supportive work culture at Wistia. The conversation emphasizes the need for empathy and understanding in the workplace, especially for parents and those facing personal challenges.
More About Megan Dalessandro
Megan Dalessandro (most people call her Meg) is a content producer, creative director, and brand marketer who has spent most of her career trying to figure out what balance actually looks like and whether it really exists.
For a long time, she believed the next title or promotion would finally bring the security to start living the rest of her life: traveling more, getting married, maybe starting a family one day. As the kid of a single mom, she was determined to build a steady foundation, no matter what. But after she broke her ankle in three places and got laid off in the same season, she realized no amount of ambition or planning could protect her from uncertainty.
That pause forced her to rethink everything. She started her own business, learned to trust her instincts, and decided it was possible to build a career and a personal life side by side without feeling like she was failing at one or the other.
Today, she has found that sweet spot at Wistia where the culture actually backs up its promises. People really do take time off, and parents (and non-parents) are supported in a way that feels genuine, not performative.
Outside of work, she’s usually roller skating at the skatepark, leaving voicemail newsletters about creativity, or taking too many photos of her cat, Noodle. She lives in Oregon with her husband, James, and is still learning how to let work be just one part of a bigger, more interesting life.
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