From New Virtual Assistant to Home Care VA to Manager of Operations: Michelle’s VA Journey (Chapter II)

By Michelle Dimen, Manager of Operations & Strategic Alliance, OLIVIA Professional Solutions

Disclaimer: This blog turned out to be a little longer than expected, so it’s now a two-part series. I didn’t plan to write this much, but once I started, the story just flowed. Hopefully, it inspires readers, especially fellow virtual assistants, to reflect on their own journey and growth.

Chapter I shared my humble beginnings and the first half of my story alongside our CEO, Ms. Kat. It’s meant to inspire home care virtual assistants to find purpose in their work, no matter how unfamiliar or challenging it may seem in the beginning. ICYMI: If you haven’t read Chapter I yet, I highly recommend starting there to follow the full story.

Chapter II continues with the second half of my journey, how life has shaped me through both challenges and growth, and a glimpse into what’s next as I step into a new season of leadership and purpose. 

Chapter II

The Birth of OLIVIA Professional Solutions: A New Chapter in VA Leadership

In summer 2023, about two years into my journey as a Home Care VA with Nest & Care, Ms. Kat came to me with a dream. She wanted to build a virtual assistant staffing company focused on helping home care owners, people just like her, and skilled and talented Filipinos. She asked me, “What do you think?” Without hesitation, I said “Yes, of course!”.

She slowly pulled me out of Nest & Care’s operations since the team we had built was already thriving. We didn’t have a blueprint, just a powerful idea and a whole lot of trust. I jumped in and started helping wherever I could. I helped design and build our first US-based website, developed the training program, started training our first small group of VAs, created the sales presentation, met with future clients, and even helped figure out the matching process. We hadn’t even officially launched, but we already had our first batch of trainees and two placed VAs.

From building a company from scratch, I started feeling even more inspired by the kind of leader Ms. Kat is: kind, smart, direct, and someone who knows exactly what she wants. She leads with clarity and compassion, and watching her bring OLIVIA to life made me believe in the mission even more. 

In June 2023, OLIVIA Professional Solutions was officially launched into the world with just three of us in the team: Ms. Kat, myself, and Melchie, our now Chief Executive Assistant and Office & Admin Coordinator. From a team of three to now twenty one people and one vision, we built something that is now changing lives every single day.

Life Paused, But the Mission Continued

In late 2023, I had to step away and go on medical leave. It was a challenging season, filled with both physical and emotional struggles. But throughout that time, Ms. Kat never stopped reaching out. She stayed connected, checked in, and gave me the space to heal at my own pace.

When I was finally ready, I returned in mid-2024 on a part-time basis. I started helping with marketing content and worked on designing our second PH-based website. A few months later, just before the holidays, Ms. Kat offered me the role of Manager of Operations. I gladly accepted with a full heart.

By February 2025, what was supposed to start as part-time hours to support my recovery quickly became full-time. I was so involved and excited to connect with everyone, old and new, that I wanted to learn all the new processes and meet every member of the team. By our second anniversary, what began with just the three of us had grown into a strong and passionate team of twenty. I couldn’t be prouder of how far we’ve come.

The Colors Behind the Journey and All the Lessons I’ve Learned

On paper, I’ve held many roles: virtual assistant, scheduler, intake coordinator, digital marketer, virtual team lead, client success manager, and now, operations manager. But behind all of those titles is the real story.

I grew up in a broken family and an abusive household. Life wasn’t always kind. We were forced to live with our relatives since the 3rd grade, and we got out of that unhealthy space by junior year of high school. My mom was a strong woman who had to leave for the United States so that we, her twin daughters, could survive. Our relationship wasn’t perfect, and for a long time, I didn’t fully understand her choices. But now, with more awareness and healing, I recognize she was doing the best she could while carrying everything on her own. Getting to that point took time, acceptance, and a lot of inner work.

Through all of that, I learned how to be resilient. I learned how to be brave. I learned how to survive, and eventually, how to thrive. Sharing a few bits of me:

I’m a multi-instrumentalist, singer and songwriter, and part of a band called Southern Lights. We’ve been on hiatus lately due to life’s curveballs — we lost our beloved drummer, who was also my future brother-in-law, and I’m still recovering, physically unable to play live shows. Some members have started their own businesses, but we still have a full album to release and hope to return to the studio and stage soon. I am personally inspired by a mix of very different artists like Paramore, Foo Fighters, Sara Bareilles, Lizzy McAlpine, Coldplay, Mayonnaise, Hale, Kamikazee, Urbandub, and many more. Their sound has shaped how I write, feel, and express myself. What I learned? Life will throw you into grief, pause your plans, and test your strength. But creativity, hope, and purpose can still live in the waiting. Resilience means finding meaning even when things are on hold.

I have an identical twin sister, and yes, we look and sound exactly alike. The fun twist? My fiancé also has an identical twin brother, and I’m in a band with them. What are the odds? Life can be oddly magical, and relationships rooted in deep connection teach you how to listen, support, and laugh through the unexpected. My twin sister and fiance are the strongest people I know and they keep me grounded.

I was a CAT Commander in high school. I was strong-willed, and absolutely loved drills and strategy. Leadership is not about being the loudest in the room, but about standing firm, taking charge, and staying disciplined when others need direction.

I played volleyball and learned early on what it means to be part of a team, lead a team, and be strategic. Teamwork and hustle have stuck with me ever since. It’s a skill for life. You learn to win together, lose together, and grow stronger when you communicate, trust, and hustle with others.

I was a Dean’s Lister in college, but the journey wasn’t perfect. I failed my second-year physics class once, and that moment humbled me. I promised myself I would do better, and I meant it. Then guess what, I almost failed again. But I kept going. I studied harder, asked for help, and pushed myself beyond what I thought I could handle. And eventually, I made it through. By the time I reached my junior and senior years, I became one of the top students in some of the most challenging majors in our nursing course. That experience taught me that failure doesn’t define you, your determination does. Failure is never final. What defines you is how hard you get back up, how much you're willing to learn, and how far you're willing to push yourself beyond your comfort zone.

I’m a gamer at heart. I grew up playing PC, console, and mobile games. It’s one of my favorite ways to disconnect and decompress. Even play has a purpose. Gaming taught me patience, strategic thinking, and the importance of stepping away when my mind needs rest and recovery.

As creative as I am, I won’t pretend I’m good at everything. I have two left feet when it comes to dancing, and I fully own that now. Funny enough, I’ve always led my high school class through multiple cheering and dance competitions. I honestly don’t know how I pulled it off, maybe it was sheer confidence or having the chance to lead and inspire. Looking back, it makes me laugh, but it's also something I’ve come to embrace. Not everything has to be perfect to be meaningful. You don’t have to be perfect to lead. Confidence, passion and empathy often matter more than skill, and there’s power in embracing your imperfections with humor and grace. Inspiring others has always been a part of  me.

My fiance and I own and operate a small business, we began in August 2024, and now we’re opening a 2nd branch soon. In addition to our band, this has taught me how to be more effective with my time and how to manage personal things outside of work. I learned to be more patient and think about the people who rely on us in terms of their livelihood.

I’m a huge fan of RuPaul’s Drag Race, and I genuinely love a wide range of shows. From time period dramas to sitcoms to k-dramas to musicals and theater-based series. There is beauty in diversity. Openness to different stories, cultures, periods, and perspectives makes you more compassionate, creative, connected to others, and worldly.

Last but definitely not the least, I have two lovable puppies who bring joy to my everyday life. I don’t have kids yet, but my twin sister and I feel complete because of them. They have taught me to be more patient. Patience, presence, and unconditional love can be taught by the smallest companions. Caring for others teaches you how to slow down and lead with heart.

These aren’t just stories or fun facts. They are the pieces that built the person I am today.

I’ve come to realize that I no longer need to hide the parts of myself that feel too complicated or too personal. Sharing who I am, the highs, the losses, the healing, and the humor, is part of what allows me to lead with empathy, creativity, and strength.

The mental space I’m in now is what fuels me. It allows me to care for others while still showing up as a leader. It gives me the capacity to guide others with kindness and directness.

It’s a balance I’ve learned to hold, and one I’ve admired in someone I deeply respect… Ms. Kat.

What’s Next for Michelle

I look forward to growing OLIVIA alongside Ms. Kat and our incredible leadership team. In just about two years, we’ve grown from three people to over 20, with more than 170 working virtual assistants and 100+ home care clients.

To all new VAs or anyone still finding their purpose, it’s okay to be scared. What matters is showing up. You carry a little fear with you and let it shape you into something stronger.

There are no shortcuts, but when you stick with it, this work is incredibly fulfilling.

If you’re looking for a job that brings meaning, purpose, and growth, we’d love to talk to you. At OLIVIA, we don’t just hire. We nurture. We guide. And we help people rise… Together.

Again, I am Michelle, your Manager of Operations & Strategic Alliance. If you ever need someone to chat with, I’m just a message away.

👉 Are you inspired by Michelle’s story? Take the next step in your own VA journey! Visit our website to apply as a home care virtual assistant today: www.oliviapros.ph