Big Bear, Captain Underpants, and Being My Own Boss

HEATHER:

Last week, while in Big Bear, one of my triplet nieces, Daisy, and I drifted into the middle of Big Bear Lake, the sun beating down on us, our kayak just far enough from the shore to escape the noise.

After some questions about my kayaking expertise, she relaxed and started chatting about school and her favorite stuffy, Flower Bunny, and the other bunny family. I remember thinking, “This is one of those perfect moments I’ll remember forever.” This wasn’t a vacation I spent months planning; I wasn’t even meant to go.

When Hollie told me that she and her husband, David, were taking the triplets to Big Bear, I was hoping to join them, but they were only going for a few days. I’ve shared before that I joined Toastmasters to improve my public speaking (and lessen my stage fright), and I had a speech scheduled for Monday, the day they were leaving. Not one to miss out on fun experiences, I channeled my adventurousness and decided I’d do my speech on Monday night, wake up super early, and spend twenty-four hours in Big Bear.

(Side note: I won best speech, and the organizers suggested I compete with it in the new year. Cheers to doing things that scare you.)

Anyway, I woke up on Tuesday at 4:30 am, grabbed my Watermelon Celsius, and hit the road. When I arrived, my nieces were so excited! The hero’s welcome I received from the girls made it all worth it.

We crammed so much into the day: kayaking, the zoo, snacks in the backyard of the cabin, and after a quick rest, dinner at a quaint Italian restaurant. We ended the evening snuggling on the couch with ice cream and Captain Underpants (which I may have enjoyed more than the girls).

I realized in my past life, I never would have taken an impromptu trip like this. Corporate life is rarely conducive to spontaneity. Even if I had been able to swing it, I wouldn’t have enjoyed myself in the same way. I would have been checking emails nonstop, worried about what I was missing (even if there was nothing to miss). My guilt over perceived expectations would have kept me mentally checked out of conversations.

Even in my early career days, when I was able to get away, work consumed me. I remember being in a hotel in the jungles of Belize, attempting to download a movie to give notes on, while the concierge looked on completely baffled as to why I was working on my vacation.

I also soon learned that the motto in Belize is “Go Slow,” something that was, until my recent departure from corporate life, a completely foreign concept.

I’ve been told for years I talk too fast, and I used to say in my head, “You think too slow.” The best part about the jobs I’ve had is that moving too fast has been exactly what was required. Though I now recognize the critiques are fair and my defensiveness was getting in the way of progress. The consistent feedback I get in Toastmasters is to slow down, so clearly, it’s a me problem, one I’m trying to work on. But eventually going too fast for too long takes a toll.

I am so grateful, and this new freedom is a gift. These last couple of weeks of summer, I’ve taken off early, gone swimming with the family, picked up In-N-Out dinner before the Friday rush (IYKYK regarding the lines!), and done movie nights with my fiancé and stepson. As much as I love it, I also find myself feeling guilty, like I’m playing hooky from imaginary responsibilities. I’m my own boss. Why can’t I chill out?

I think a lot of it comes down to reassessing who I am without a corporate entertainment job and learning to redefine myself. I’m not the only one. According to a survey in Catalyst, in 2025, 455,000 women left the workplace. Some were due to layoffs, but 58% were voluntary. Yes, many of these women were being forced back into the office post-COVID and struggled with childcare issues, but a significant number of women were simply over the hustle culture and feeling burned out. And we all know that even if you’re choosing to leave, so much of our identity in the Western World revolves around our careers.

This idea that “I’m an executive” or “I make movies and TV for Hallmark or Tubi” was exciting. Now, that’s no longer true. I’ve had to rewire that thinking as many of us have, whether we’ve chosen a new road or the decision was made by our AI-loving corporate overlords. For someone who has defined herself by her career for so long, it’s been an adjustment.

When people ask what I do for work, I feel almost naked. “I’m a producer,” I say. Then I panic, wondering what they’re really thinking now that I no longer have the backing of a major company.

It’s not that I’m not proud of the work I’m doing. I’m developing films and producing our Seeing Double Entertainment podcast, and trying to write (with Hollie reminding me to stop making excuses and just WRITE a script!) I’m working hard to find ways to create, but I’ve always had the safety net of corporate. That feeling has lessened over these last several months as my nervous system has returned to normal.

The other thing I remind myself regularly (and we all should) is that no one really cares what we do. Everyone is worrying about their own careers, their own struggles, their own identity shifts as this business convulses and pivots and reshapes itself into whatever it will become.

What I do miss and still struggle with is the structure a corporate job provides. There’s nothing like fifty people (or more) waiting on your decision to really kick you into gear. I thrive on deadlines and urgency. My ADHD is excellent at allowing me to procrastinate, and now that I set the deadlines, I’m responsible for holding to them. This is terrifying or liberating, depending on the day.

I will also admit that I dislike the financial uncertainty that comes with being a freelancer (Hollie side-eyed me when she read this, as her entire career has been freelance), but it’s true. I’m fortunate that I made good financial decisions that allowed me to make this move, and I’ve gotten consulting work to tide me over, but having a stable paycheck and insurance is what keeps so many of us tied to jobs we may not love. Even nine months later, I still have to work to keep the fear at bay when asked about my long-term plan. It wasn’t like I ever felt completely secure, even when I had a steady paycheck. I’d been working at Hallmark for about five years, and I was finally given my own office. (I’d still like to have a chat with whoever decided open floor plans were conducive to good working conditions.)

There was still old artwork from the previous executive in the office My boss walked in one day and said, “Are you ever gonna put something up?” I joked, “Isn’t that when people get fired?” He found it hilarious, but I never hung a single photo, and I worked there for another four years.

People ask if I want to go back to a corporate entertainment job (these are people who clearly do not know the lack of exec jobs or the competition to get them), and my feelings are mixed. I miss the camaraderie, the rush of reading scripts, overseeing rewrites, casting, selecting wardrobe, and the millions of other decisions I was required to make before cameras ever started to roll.

But I still wonder if the pros outweigh the cons. In this new era, having had a chance to slow down, I get to be present with my fiancé and to see Hollie and my nieces without being consumed by anxiety that I’m not doing enough. I don’t have to worry about Wi-Fi service in Belize when I’m on vacation or stress over whether or not I can take a random Tuesday off to go on a summer getaway with my family.

There’s still so much I haven’t figured out, but that’s okay. I’m hopeful about the creative projects in the works, but I’m also embracing the slowness of this season. Captain Underpants on the couch with my nieces is good enough for now.

Have you left the corporate world? How has the transition been? Or if you’ve always been freelance like Hollie, how do you manage the uncertainty and lack of structure? Let us know in the comments.