From Toxic Workplace to Digital Nomad | The Check-In - March 27, 2026
Me, 3/27/26, Italy
Letter
Dear Reader,
The Check-In is something I send out every other week to share what I’m reading, thinking, consuming, and sometimes dreaming.
Digital Nomad Life + Dark Tetrad Personalities
I arrived in Italy this past weekend via a stopover in Boston. I’ve been living as a digital nomad for the past 2.5 years.
A digital nomad is someone who can work remotely—doesn’t have to go into one physical workplace each day. How did I start this path at age 38?
In 2023, I found myself working a job, which could have been my dream job, in child trauma prevention, for the State of Massachusetts, but we had an Executive Director (ED) with a dark personality, meaning she had aspects of narcissism, Machiavellianism, psychopathy, and sadism.
Yes, even sadism. On one occasion, she had her sister-in-law (SIL), who was a Police Chief integrating trauma-informed teachings in the Seattle, WA area, speak to our team virtually about their work. She bullied her SIL in front of all of us, making her the butt of a cruel joke. The look of disdain on her SIL’s face in that moment !! It was clear that this woman was long used to ED’s tactics and was fed up.
Learn more about the Dark Tetrad of personality features here. (Source = Psychology Today).
“Narcissism: A belief that one is special, particularly gifted, obsessed with themselves and that they are superior to others.
Machiavellianism: A tendency to see people as a means to achieve one's own goals.
Psychopathy: A condition characterized by a lack of affective empathy and the willingness to exploit others.
Sadism: The tendency to derive pleasure from the pain or humiliation of others.”
I reported her bullying to HR, but unfortunately, workplace psychological abuse is not against the law anywhere. In fact, we may have built a whole work culture, a whole country, even, in support of bullying and coercive control.
We found her using state funding in an illegal way, and I blew the whistle, which our institution didn’t appreciate. It became an extraordinarily stressful 3 months for me in the summer of 2023 while they conducted the investigation.
In the end, even though she was fired, I also had to leave because the institution had become so hostile.
I went on a trip to Finland to a music festival and to go trail running in the National Parks of the North. The day I got back in late August, I was in a bicycle accident in Boston and broke two ribs, puncturing a lung.
In the days following the accident, which had followed the immensely stressful investigation of the ED I had reported, I wondered what it would be like to choose joy. I started concocting a plan to travel and work remotely, dreaming up a consulting company and launching Tend Collective with the help of three of my past colleagues.
Want to learn more about my consulting company? Attend this free event, open to all who work, on Wednesday. Register here.
That Fall of 2023, I traveled to Spain, Portugal, Poland, Germany, Austria, Slovenia, Croatia, and Italy.
In 2024, I hit the road again, traveling to France, Switzerland, Austria, Hungary, Serbia, Bulgaria, Türkiye, England, Norway, and Scotland. A highlight was attending the Paris Olympics!
In 2025, after spending the holidays in California with family, I again ventured out to Türkiye, Portugal, Greece, Austria, Italy, and Albania.
I was curious how long it would take for me to feel tired of moving around and not having a home base; it took about 2 years.
I am currently exploring Italy as a new permanent home. They offer a digital nomad visa.
I stopped by my apartment in Boston, where the same tenant has been renting it furnished since I departed in October of 2023. It was a time capsule—with all of my things exactly as I’d left them, with some of his added to the mix. I saw the alternative, stable, in-one-place version of my life there. I was surprised to feel so much grief. Even though I’ve loved my nomad life—it’s a dream life for sure—at one time, I’d dreamed of landing that perfect job and creating the perfect home. Maybe I still needed to grieve the loss of that dream that was ruined by the toxic workplace experience I suffered.
When we grieve, which is to allow ourselves to feel every negative emotion fully, allow ourselves to feel disappointment for the dreams that didn’t happen, we make space for more genuine gratitude.
»Read my blog: Skipping Grief Work Causes This Kind of Harm to Our Bodies.«
We can feel grief and gratitude at the same time.
Photos of Italy
Some photos so far:
Blogs this period:
No new blogs.
Instagram videos:
No new videos.
Warmly,
Alison
Action Item:
Go for a run. Or a jog. Or a walk.
Move your body in a way that gets your heart rate up for at least 30 minutes a day, 3x a week.
Running and jogging are great because you don’t need a ton of things to get started—just a pair of shoes and maybe some headphones.
The book that helped me develop my love of running was Born to Run, which I read in 2012. At that time, I couldn’t run more than a few miles without feeling knee pain. A friend recommended I look into Chi Running. I took a course in Chi Running in January of 2013 and was able to run a marathon (26.2 miles) later that year! Then another one. Chi Running was exactly what I needed to learn to increase my mileage without pain and develop a running practice.
Check out the YouTube Channel here for Chi Running.
Check out my interview with Born to Run’s Luis Escobar on his podcast Road Dogs here:
Reading, watching, and listening to:
Watching.
I accidentally watched two films back-to-back on the flight from Boston to Europe with the same dark theme: post-partum and maternal psychosis.
The two films were:
Witches (2024)
If I Had Legs I’d Kick You (2025)
The description of Witches is: “Director Elizabeth Sankey explores the connections between postpartum mental health and the portrayal of witches in Western society and popular culture.”
I was surprised that the documentary was less about the history of the witch trials and how that relates to the experience of motherhood, and was actually a handful of women’s direct experience with post-partum psychosis. I knew someone once who had experienced post-partum psychosis, and she was able to get good treatment. However, I couldn’t fully grasp the condition. This documentary was enlightening on this important topic. I was sad to learn that the UK offers better, more holistic treatment options for mothers than what’s offered in the United States.
The description of the second film is: “With her life crashing down around her, Linda (Rose Byrne) attempts to navigate her child's mysterious illness, her absent husband, a missing person, and an increasingly hostile relationship with her therapist.”
I was shocked to find that it seemed to be an extension of the first film, with the psychosis extending well into motherhood, albeit this time in a dark comedy sort of way. It was a tough film to get through, even though Rose Byrne was captivating to behold in her role of an overwhelmed mother. It was clearly an indictment of patriarchy and how our society isolates mothers and gives sole child-rearing responsibility to them. Christian Slater plays Rose Byrne’s husband as hilariously narcissistic and aloof.
—
On my flight from SFO to Boston I watched a film I LOVED, Sunfish and Other Stories on Green Lake (2025).
It’s what I recently learned is called “gentle filmmaking” and it’s my favorite type of film. In it, there are several stories of characters connected by one lake in Michigan. Many of the characters are lonely and seeking connection in very interesting ways. I cried most of the way through because I love the ways that we reach for and find each other. The lake and nature scenes were calming.
Buying/Using:
Gear.
The running watch I use is a Garmin Vivoactive 5, and I love it! $178. I use it also to record other activities like yoga and CrossFit and it also calculates HRV, which is a measurement of how stressed we are.
