Choose Your Own #CareerAdventures: with Samantha Pennington

This week we introduce digital agency entrepreneur and online community founder, Samantha Pennington of Oree Virtual. Her remote work fills her days with anything from web design to graphic design, to writing, to SEO – all of which she employs as tools in her efforts to shift the status quo and be a force for good!

A big thank you to Sam for telling us her adventures that take her from sustainability and not-for-profits to delivering digital projects and brands that serve a meaningful mission.

1. Tell us about yourself.

I’m Samantha Pennington, the sci-fi & fantasy novel obsessed, revolutionarily inclined, and oh so queer entrepreneur behind Oree Virtual. Oree Virtual is a full-service digital agency serving women, people of color, & LGBTQIA+ changemakers that want to shift the status quo and become the majority in business and leadership. We help build our client’s brand authority, trust, and visibility online.


I’m also the co-founder of the largest community of women in SEO, the Facebook group Sisters in SEO.

2. What are you working on now? 

I’m always working on expanding my business and finding new clients, but I’ve been especially focused lately on building more passive streams of income like affiliate marketing. I’ve also been planning the launch of a branding course and e-book, as well as a product store for Sisters in SEO.

I love my client work, but there’s something magical about waking up to find more money in your account from work you did in the past!

3. Could you tell us about how your career adventure started, about what experiences, challenges or opportunities you came across over the years that led you to choose your own adventure? Where has your career adventure taken you in the past leading you to where you are now? 

I always thought I’d be poor. I actually pretty much aspired to be poor, which is weird to say, but it’s true. After highschool when I began to learn about our culture and capitalism and so many of the ills being done by massive corporations and the ultra-rich, I started to associate money with evil, misused power.

I’ve also had an activist’s heart for as long as I can remember, so while I aspired to be poor, I also planned to work in the nonprofit world. I always got bored really quickly at my jobs, whether I got sick of dealing with the crappy workplace cultures or sick of doing the same thing every day, I just figured I’d never be satisfied and never stick with anything long.

That was the extent of my plan really, even as I was graduating college… I imagined I’d just drift from job to job in the nonprofit sector barely making money and finding my joy outside of work.

Then I met my current partner who challenged my mindset towards money and helped me recognize how I could craft my own job with whatever workplace culture I wanted and choose what I do with my work every day.

I have NO IDEA how this idea never occurred to me before, but it literally blew my mind. Once the idea of entrepreneurship entered my mind, it never left.

There were definitely hurdles along the way, like getting past the idea that I didn’t need to constantly search for a “real job” because my business is a real job. But honestly, once I made the decision to make my business my full-time job, sticking to it has been easy. I get to choose the people I work with, I get to live my values through my work, I get to eat whenever I want, and I get to do something different every single day. There couldn’t be a more perfect fit for me.

4. What past projects spark joy for you when you look back at what you have worked on? 

I’m still not quite two years into my business so everything still feels quite new and all my projects spark joy for me. Before I started my entrepreneurship journey though, a few projects stand out as perfect precursors to where I am now.

When I was in college at Southern Oregon University I became the Director of Sustainability for the university’s student gov’t, was a student employee, the Director of Education & Outreach for the on-campus farm, and eventually became a full-time employee, the Sustainability Specialist for the Landscaping Dept.

Throughout that time, I organized other students, staff, and faculty to build an on-campus farm with an outdoor classroom, children’s garden, apiary, and food forest. We started an on-campus farmstand, a CSA (community-supported agriculture), and designed a composting program to save waste from the dining halls and turn it into fertilizer for the Landscaping Dept. We became the first ever Bee Campus USA and hosted (what we think) was the largest ever volunteer event on campus planting an entire Arboretum (tree garden) with more than 6,000 plants in one afternoon.

All of that community work and learning how to build initiatives from the bottom up, taught me how to recognize what needs to be done, find the resources I need to get it done, and build relationships along the way.

This wasn’t even part of my course work, but these were certainly the most influential aspects of my time in college.

5. How do you choose what to work on?

I choose what I work on based on how much money it will make me, how much I want to work with the people involved, and whether or not it aligns with my values.

I’d say the biggest deciding factor is typically the people involved.

It’s really hard to want to do good work for people you don’t like and I refuse to sacrifice the quality of my work.

That means if I am getting whatever kind of red flags from someone, I  avoid working with them.

6. What advice, practical or otherwise, would you give to someone looking to start a career adventure similar to your own?

You’re already good at something. You already have some sort of experience. You don’t have to have entrepreneurial experience to have valuable experience. So pick what you’re already good at that people are willing to pay for and get started.

You don’t need a website or even any money to get started, there are plenty of free programs out there to cover everything you need to be a beginning entrepreneur. All you need is time to find clients and confidence in your ability to figure out whatever that client needs done.

There have been so many times I got hired to do something I had never done before, but I knew that I could figure it out. Those clients never had to know that I was a new business owner because I leveraged my past experiences to show them I was capable. I never doubted my ability to research something and figure it out and worst case scenario, I knew I could hire someone else to help me complete a job that i couldn’t figure out—but that hasn’t happened yet.

7. Could you describe your day-to-day at “the office(s)”?

I work at home and occasionally at coffee shops or the library. A typical work day for me is to wake up around 7-7:30, do a bit of yoga (if I’m feeling extra on top of my game), have breakfast, then check out what work I could do for the day.

I take note of everything that needs to be done that day and what has a more flexible deadline. I put on my headphones and listen to some instrumental music on Spotify and get started on my must-do tasks for that day. I have a snack at 10:30 and usually check my email and engage in my Facebook group then work until 11:30 when I have lunch.

After lunch I might go for a walk or do the dishes or some other little errands then I go back to work. At this point, I typically have my must-do’s for the day done, if not I keep plugging away, but otherwise I’ll usually spend this time of the day checking off small easy tasks from my list. My brain is usually a lot more tired and easily distracted after lunch so working on small, easy to finish tasks is my best bet at productivity.

I have another snack around 2:30 (lol I really do plan my day around snacks! I struggle with low blood sugar so it really helps to work at home and I have alerts set on my phone telling me to stop and eat!). Then I check emails and my Fb group again and work until about 4:30 when I start to make dinner.

I do have weeks where I’ve got huge projects on short deadlines where I end up working from 7AM until 10PM, but I always stop to eat and those weeks aren’t my norm. My typical workday is pretty chill and I love being able to stop for a chat with my mom on east coast time or my best friend on west coast time pretty much any time I want!

8. Where do you feel you work best and thrive the most?

Location-wise, where I work best really depends on what I’m doing for the day. If I’m writing, which requires a ton of focus for me, I love to go to a coffee shop or library and put my headphones in. I’m less distracted at coffee shops because I really have nothing else to do, but work.

If I’m going to be doing a web design project, I prefer to be at home because web design has me hopping around from graphic design, to writing, to SEO, emails, and phone calls etc. Home has all the different tools I need, my food and bathroom are right here and if I need to make a call really quick, I’m not going to be disturbing anyone or have to get up from my desk.

I do typically prefer to work at home because everything I need is here and I can pivot between any task, but when I’m feeling particularly sluggish and unmotivated, coffeeshops are perfect. The coffee and the lack of options that can distract me help me work when I don’t feel like working.

9. What inspires and drives you every day?

I genuinely love the work I do and the people I work with, so that’s a great driving force for me every day. I also really am a perfectionist when it comes to providing the best possible results and experience to my clients so even when I feel like slacking, I might slack on my work for my own business, but I just can’t for my client work.

Two things inspire me every day though.

The first is the bone-deep need I have to see more women, people of color, LGBTQIA+ and other underrepresented folks in positions of power. Working together I know we can make the biggest, boldest, and most crucial changes in our world.

Supporting that vision gets me back to my desk every day.

The second is that, while I don’t have children now, I know I want to. When I have kids, I want to be able to be home with them as much as I want to be, I want to be able to support them financially and emotionally, and I also want to be an example for them. That’s one of my biggest inspirations and goals that drives me.

10. What advice would you give to your younger self, knowing what you know now?

You’re a fucking badass, you know this so don’t let anyone else define who you are or what you should be doing with your life. Your family, that sexist boss, everyone around you following the path laid out for them… whoever it is that’s influencing how you see yourself or what you see yourself doing in this life, stop listening to them.

No one else controls your choices and only you can decide how to be who you really want to be.

And once you really know who it is that you want to be, regardless of what everyone else is telling you, the easier it’ll be to drown out those other voices and become that person.


You can find out more about Sam’s work at Oree Virtual by clicking here or you can visit/join the Sisters of SEO’s Facebook group here.


Feel free to contact us if you have any questions about any of our career adventure stories. Come back soon to read more career adventures! Contact us here if you’d like to be featured here to share your own career adventures story or if you would like to write a guest blog for Project Anywhere.

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