Today we’d like to introduce you to Jenn Schwager.
Hi Jenn, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Oh, where to begin!
I grew up in a small town in New Hampshire. Picture quintessential suburbia with a lot more green. It was a town where everyone knew everything about everyone else, and a town where parents would even gossip out the teens in town. I was surrounded by a lot of affluent families with very typical family dynamics – father, mother, 2.5 kids, and a dog. Divorce was common, but I remember explaining the family I had to friends at school and they were always puzzled.
Both of my parents each had partners before meeting one another. My mom was engaged to her high school sweetheart and had my older sister, Carly, and my dad was married to his college girlfriend and had my older brother, Evan. Both of parents went through separations and were single parents and had met each other at work. Their beginning came about as friends at first. But after getting to know each other on a deeper level, and being able to relate to the other person’s struggles, love grew and grew.
Fast forward and they were eventually married and then came along me, and my younger brother, Michael. Now, keeping in mind that both of older siblings had other half siblings through their other set of parents. I remember as a kid being in the backseat of the car during kid drop-offs and custodial visits, watching everyone try to keep their cool. I understand they did their best, but the strong undertones of hostility, resentment, and disappointment were always present.
I was (and still am) a very strong-willed person. I am particular, and always had a vision… even when I didn’t think I did, looking back, it’s clear I always had a path I was following. I am strongly intuitive and had to practice discernment at a very young age. There were a lot of very adult things happening around me from a very early age, and I always had an inner knowing that if I stayed where I grew up, I would drown. I connected with friends at school but it was extremely difficult at times. Bullying as tough on top of natural growing pains. I didn’t know who I could trust, so I felt the only person I really could lean on was myself.
My world back then felt very confined but I knew there was more out there for me. I would create imaginary worlds and spend all day in them. It came out in the games I played with friends, and in the journals I kept as a little girl. I was constantly reinventing myself and my environment. One day my room was green, the next it was hot pink and orange. I’d beg my dad to take me to Home Depot “just one more time!” and I’d handle the rest myself. I would collage and create art on all my walls. I’m sure my parents loved that, but my room became my safe space and a place where my reality didn’t exist.
The world was never black and white to me. It was always grey.
In May of 2008, at ten years old, that is when my life flipped upside down. My older brother, Evan, died of a fentanyl drug overdose at 18. Evan was an honors student, talented soccer player, kind, spirited, joyful person. He made a mistake trying something he didn’t know at a high school party one month before graduation. It shared publicly on my podcast and in my book the story in great detail but I will say this here: I woke up knowing that something was wrong. I had this big, three-pane window in my bedroom that at the time, my bed was right under. I remember waking up and looking through the window at the trees thinking to myself, “What a gorgeous day. Why does it feel awful?”
As the day unraveled, it just kept getting worse and worse.
We were all supposed to be at my younger brother’s soccer tournament and I remember my parents sending me off with some family friends that day as they went to the hospital. I sat on the grass by myself, twirling and picking the blades out in clumps. I could hear the faint sounds of whistle blows and cheering parents, but as I’d look up, I could hardly see with tears in my eyes. When I finally turned around and saw my parents walking toward their friends,
I took note of the extremely long, tight hugs they were being given. I knew instantly it wasn’t good, and my suspicions upon waking were right. Unfortunately, I was told about Evan’s death in the parking lot of this game with all the kids from my school watching. My mom was sat in the drivers seat of her car and I in the passenger, with my dad between my seat and the front passenger door trying to shield me from the onlookers. I wailed like I never have in my life. The air was gone from my lungs. It felt like a giant hole had been stamped into my tiny chest.
My brother’s passing was the first domino to fall in my life that had me brace for impact. Bullying got worse after Evan died, my home life became extremely tumultuous, and it felt like for years I had to put my head down and hang on tight until it didn’t all feel so heavy. I think what most people miss about grief is that you’re grieving the one who died, but infinite versions of you died, too. Same with the ones around you. And for the last 20ish years, that’s been the most challenging part for me to heal through.
Prior to my brother passing, my family was no stranger to trauma. My maternal grandfather, Rick Masucci, died of suicide in the early 2000s. My mom didn’t tell us the cause of death until we were old enough to understand that a permanent solution is not the remedy for a temporary situation. My dad also dealt with his fair share of trauma in his family growing up. I had felt the weight of generational trauma long before I had words to name it, or even the confirmation for it. I know my parents did the absolute best they could. Aren’t we all trying? As I’ve aged, it’s been one of the ways my heart has stayed open. I have a lot of admiration for my parents and what they have gone through, especially losing a son after everything else.
At the same time, despite the amount of pain I was in, that is what served as the catalyst to begin therapy. My mom was very big on mental health for the aforementioned reasons and “mental health days,” were always a thing in my home as a kid – which I was very grateful for. When Evan died, my mom had me see a grief counselor but I wasn’t feeling it. It was quite foreign and honestly, I didn’t like the woman I was paired with. After some time, I was ready to seek out counseling on my own and saw the psychologist that other family members had been seeing. His name was Al. Al, if you’re reading this, you saved me!
I saw Al for the better part of 12 years. He saw me grow up. It was a really transformative experience, especially as he knew every member of my family so I didn’t have to spend time explaining everyone and every disaster that occurred. I saw Al all the way up to graduating high school and even during my early college career, up until he retired. Working with him exposed me to clinical help. It help me understand and process my emotions.
As I was forming into a young adult, I learned more about myself and what life would look like if I didn’t try to course correct. Looking back on it, this is where I began to dive deeper into self-help. Sure, it’s obvious now but as a young woman growing up, I sometimes wasn’t aware of all the progress I was making. It wasn’t until I got older and began my life outside of my childhood home, where I really felt gratitude for my younger self and the experiences I endured.
I worked hard in school growing up and punched my ticket to San Diego, California, where I have been for the better part of 10 years now. I attended San Diego State University and graduated in May 2020 during COVID. I still have “pinch me” moments living here because this is exactly what I dreamt up as a young girl in my colorful bedroom in New Hampshire.
Like many others, my post-grad plans were derailed due to the pandemic. I found myself scrambling to find work after graduating to make sure I could stay in San Diego. As luck would have it, I was able to secure a job at GoFundMe during their first ever time hiring contract workers. As you can imagine, their site was inundated and business was booming. Funny how that works.
As soon as I was old enough to work, I’ve always had a job. That was a non-negotiable in my home. So working post-grad was no different in that way, but I did find myself wondering, “Is this all there is?” I am confident most people feel this way when they’re right out of university and they’ve landed a role. I had hopes of staying there for a longer tenure, but when my contract was up, I was back to square one. Post-GoFundMe, I landed another contract role at Sony Electronics.
I was grateful for the job because I landed on my feet again but man, this one killed me. It was soul sucking for me. Everyday I dreaded it. I remember journaling and wishing for something different. And as they say, “Ask and you shall receive.” Working at this job is when I received a curious LinkedIn message from a man named Eric Koester. Eric was an investor, entrepreneur, writer, and educator. He was contacting me about an opportunity to write a book. He actually had reached out to me two years prior, but I was no where near ready to accept.
I hopped on the phone and learned more about Eric and his pursuits. At the time, he was a professor at Georgetown University. For one of this senior thesis courses, he was thinking about creative ways to give his students something real to take post-grad. He had just written a book I believe so it was fresh on his mind and he eventually landed on the idea to have his students write one of their own. The program took off and he began identifying others across the country to work with him and the publisher.
I’ve always had a pension for writing and felt I wasn’t half bad. I remember writing a lot creatively in high school, and getting to experiment with really personal pieces. One in particular I remember my sophomore year teacher telling me to “Never stop writing,” because “my words are too good to keep to myself.” I’m here a decade later and that still sticks with me.
I was miserable at my job and trying to find a new one but on that phone call with Eric, I decided this is my chance to do something different and to focus my energy elsewhere. It was about a year and a half long process and in the beginning I was writing 30 hours a week on top of my 40 hour a week job. I also chose to invest my own money upfront with the publisher and pay a bit more so I could own the rights fully moving forward.
There were a lot of logistics as a part of Eric’s process but I got to connect with other authors in the cohort which I really enjoyed. I believe I was just turning 22 when this all began and this is really where I implemented strong disciplinary habits. I have always been organized, regimented, and have had a vision but this was a new level. I took my health more seriously and began my fitness journey. I was writing a lot. I was still at the terrible job but was gunning it a bit more in my search. I felt like I really had to learn how to channel my potential and life’s frustrations into something more positive for myself.
It was not all sunshine and rainbows and when I was writing, I chose to write a self-help titled: Recalibration: How to Reset When Sh*t Hits the Fan. People told me not to cuss in the title, but at the time I was really obsessed with Mark Manson’s The Subtle Art of Not Giving a F*CK so needless to say, I was inspired. My book focused on what I knew up until that point about grief, self-discovery, and finding those who support you. It’s 12 chapters and 222 pages. I shared what I learned, interviews with other people I found inspiring, supported claims with research, and hoped that I would help at least one person with what I wrote.
When I finally published, I was 23 and some change. I was home for Christmas and hit “go-live.” My mom was so excited she purchased the first copy that night and it was overnighted by Amazon. I remember holding the first copy in my hands and it was surreal. I think I downplayed the accomplishment a lot, if I’m being honest with you. I worked on it everyday for over a year and even read it aloud 9 times (yes, I’m sure there are *still* typos in there, don’t come for me). I was getting a lot of questions from people in my life about the financial aspect and how I’d measure success. I also was surprised at the lack of support from some people in my life, too. I let those people get in my head. I regret that now a lot.
My book served as a massive transformational period for me. This is the time period of my life where I look back on my younger self with such admiration. She/I took a chance and put their creative work out into the world, like so many people before me. There are countless people who do it every single day and I was a part of that community. It’s quite scary to do it. You’re subjecting yourself to criticism and for me, giving people a look into some of the most intimate parts of my life and my soul back then. I also felt that no matter what I put out, it was never going to be perfect and I hated that. I always felt like there was something to change. It drove me nuts. I only recently learned to let that go and I’m 28 now.
I have a new found appreciation for that, though, because it forced me to appreciate the creative process and simply put: the art of trying. All we can do is try and see what happens. With each year that passes, more doors open up because of this body of work I produced. And when it’s all said and done, no matter what else I put out in my life, I will always remember the first one.
Shortly after I published my book, I thankfully was able to transition into a new 9-5. I felt a lot of my creative energy was sapped at that point and I wanted to scale my tech career. I used all of my content and writing skills in the beginning at tech behemoth VMware, and have since transitioned to another big tech role at Darktrace focusing on campaign creation and AI cybersecurity.
Creation has always sat at the intersection of my tech career and what I do in my personal time. I’ve tried a lot of different modalities, including a podcast. I created one on my own and recorded several episodes. I was enjoying it, until I wasn’t. And that’s ok. I felt like it wasn’t what I thought it was going to be and I didn’t feel fulfilled like I thought I would. Once again, learning the lesson that perfection isn’t the goal. And it’s ok to put things on ice and come back to them when and if you’re ready. Through all of my personal pursuits, I’ve never stopped filling journals, staying in therapy, and working on myself.
From 2020 to 2026, I focused a lot on immersing myself in community. I made friends with people in all different pockets of San Diego and got involved with philanthropy and the health and wellness community. I’ve met and been inspired by so many business owners and have been so lucky to meet other creatives. I have been interviewed on several podcasts to share my experiences as a creative and also spreading awareness about fentanyl. In fact, I’m speaking at a sober living house soon here in San Diego. I’ve been fortunate enough to have some media coverage as well, and as each opportunity comes, I’m so grateful for it.
Despite having gone through some of the most trying times in my adult life in these years, I always come back to trying to pour back into myself and others. I’ve learned that vulnerability is one of my superpowers and I’m choosing to harness all of the pain and use it for good. I’m an imperfect person and sometimes lose my way, but it’s the way I’ve learned to alchemize my pain.
I’m still continuing to write, to connect, and to try to find alignment as much as possible with my purpose and working to create my dream life.
We all face challenges, but looking back would you describe it as a relatively smooth road?
No, certainly not.
As I touched on before, many things have happened a long the way. I lost my older brother Evan in 2008. I experienced horrible bullying from the girls at school in the wake of his death and beyond. I struggled with loneliness and finding friends in those younger years. I felt like a freak with this giant scarlet letter because it was my brother who died of a drug overdose. Dealing with the stigma from that took a toll.
I dealt with your typical high school dramas, like heartbreak, rumors, humiliation. I was a part of the guinea pig era of the generation of high schoolers who had iPhones for the first time so dealing with everything online came shortly after. I honestly think about this a lot and have a lot of empathy for the kids who are dealing with this in 2026.
Through it all, my home life was tough as well. Without doxing certain family members, each person had their own unique struggles. I was around substance abuse issues and it felt like a pressure cooker a lot of the time. I believe that’s why I felt even more lonely because at school I felt bad and at home I felt worse at times. There were some incredibly dark moments.
College felt like a fresh start and felt like my hard work had paid off. It was my ticket out of my reality. It was my dream. But I had to learn how to be completely on my own across the country, make new friends, connect, and survive. To be honest, the moving part was easy. I was already really independent. It was finding real friends that was the challenge. Everyone is trying to find themselves in college and you’re also developing a new sense of self in a lot of ways. I realized it was a lot of people’s “do-over” moment.
I met a lot of people, some of whom I am still very close with today. Others I fell out with or the relationship faded over time, which I expected. College was where I really felt the “we grew in separate directions,” phenomenon people talk about come to pass.
Dating was also hard. I felt shame around sharing my experiences from childhood in fear that boys back then would write me off. I quickly grew out of this but if anyone’s reading this and can relate, I understand you. I really had to work on my relationship with sex as well and finding real intimacy – not just the physical kind.
Around my career and my writing, I still struggle at times. I struggled because I can be impatient. I sometimes lose faith in the journey that I am on. I have to work hard at reminding myself to be where my feet are and to continue to use the gifts I was given to carve a path forward. Like anyone my age, I at times play the comparison game; I will compare myself against this imaginary timeline and make judgements based on where I am or am not. That’s such a human thing but it’s not helpful for me. I’ve learned it’s really me against me and that’s all that matters. My path is uniquely mine and the more I look in other swim lanes, the less I connect with my purpose.
I’m still learning a lot, so don’t be fooled. 🙂 But I’ve come a long way.
I’ve had to continue to work on my relationships with my family members, to continue to work on my own relationship with grief, and to stay committed to exploring the parts of myself that I tuck away. In doing so I’ve become a stronger, more confident woman. I always find my way back to myself, which I really proud of.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I selected “Other” because I am both a professional and a creative.
I am a published author, creative, and I also work in the cybersecurity industry strategizing, creating and running marketing campaigns. I do love my marketing career because it marries a lot of my professional and personal loves. I love to make people feel things. Even in an industry like cybersecurity, at the end of the day, you’re speaking to people and helping them with their concerns. The science behind appealing to the masses is quite fascinating to me, and I love to try to get it right and help.
Marketing uses both my analytical and creative chops. My writing has opened doors into the tech industry, and I am still very much involved in content creation in my 9-5. Personally, I have so many ideas for books to write. I am always voice noting myself with downloads and concepts. My brain doesn’t seem to turn off which I’m ok with.
I think I’m most known for my book and my involvement in the community. I am passionate about philanthropy and have done a lot of work for the unhoused community (both on the East and West coast).
I am proud of my book for producing something so deeply personal, and putting it out there for the world to consume. I am also weirdly proud about how cringe it is to me sometimes. Like I said, I always felt there’s something I should change. But I was 22, hungry, passionate, and willing to try. And if my writing isn’t my best, it was perhaps the best at the time and above all, authentic. I am honoring that a lot these days.
Professionally, I am really proud of my career so far. I blinked and I ended up here but I remember the days of hating my life every time I logged onto my computer, or even stretching as far back to when I was 16 and my first job (aside from babysitting gigs), was being a medical collections caller.
New Hampshire had very strict labor laws and I had a connection through a family friend. There I was, sitting in a basement office calling people telling them they owe $40,000 to the hospital and I was still trying to get my drivers license. As you can imagine, I heard many colorful things coming from the other end of the phone line but hey, it built character.
I know my career is going to continue to take shape in the years to come, and I’m excited to see where it goes.
What sets me apart from others I really do I believe is my authenticity and my grit. I never give up. I may shed some tears along the way, but I keep it moving. I stay open and honest and I try to own my stuff as it comes up. This is applicable to my professional and personal life.
At work, I try to over communicate and I will always own when something was my fault. I understand I am working with other human beings, not machines. People are going to have off days. Their lives are happening in the background of what they need to do for a paycheck. The things I’ve gone through have allowed me to have more compassion for others, and I try to keep work fun as much as it is serious. Personally, I’ve messed up many times. Like I said before, I’m imperfect. I try to communicate my feelings as best as I can. I try to fix my bad habits. I try to always apologize when I know I’ve hurt others. To have consideration for others is one of the highest forms of love. I cringe at some of the moments I’ve had even from years ago and wish I could go back and fix how I handled them but I can’t. All I can do is try to do better next time, and take care of those that I love.
So maybe we end on discussing what matters most to you and why?
What matters most to me is continuing to find purpose, experience the world, and to have soulful connections with others. I want to continue to produce writing, and share with others. Having experienced deep loss, I understand how quickly life can change. Those who you think will be there for long, sometimes disappear right in front of your eyes. It’s important to me to tell the ones I care about that I love them, including the life that I live.
When I am deep in my feels, I think about what it would be like if I was old and grey and got to wake up in my 20s again. This changes a lot for me. It helps me shift my perspective and think about everything I have to be grateful for and the things that really matter – not the trivial stuff we can all get caught up in. I never want to have the regret of not trying to do things my way. If I try and fail, so be it, but at least I tried.
Contact Info:
- Website: https://jennschwager.com
- Instagram: https://www.instagram.com/jennschwager/?hl=en
- LinkedIn: https://www.linkedin.com/in/jennifer-schwager/
- Other: https://www.amazon.com/dp/1637306954?lv=shuf&channelId=500&plpRedirect=mhFallback
