We were lucky to catch up with Amy Olson recently and have shared our conversation below.

Alright, Amy thanks for taking the time to share your stories and insights with us today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.

As cliche as this may sound, starting my own business as a mom to 2 young girls (ages 3 and 5 at the time) has been one of the biggest career risks I’ve ever taken. I’d say this beat the risk of moving to Colorado after graduating college in Texas with nothing but an unpaid summer intern job lined up.

Why? Well, for me, I never saw myself as a business owner. I was ok following the traditional corporate path and working for another company. I graduated Texas Tech University with a degree in Corporate and Organizational Communication and a minor in Hospitality Management with my goals set for event planning. I had my dream job lined up after my summer internship with the Denver Nuggets and was ready to simply be an employee.

That was until I met my husband who happens to be an active duty officer in the United States Army. I sadly had to quit my wedding/event coordinator position shortly after getting married because we moved to Oklahoma… for 6 months. We then received orders to South Korea. Before we even received our household goods shipped from the US, I was already working as a benefits advisor and would travel throughout Korea and Asia briefing our service members on the VA benefits available to them as they transitioned out of the military. My options for work were limited due to our visa agreement but it was a fun job and kept my resume from the dreaded gap years. This was until I got pregnant with our first daughter and quickly realized this lifestyle did not easily support two working parents, especially if living overseas. After 4 years in Korea, a move to New York and our second daughter on the way, I truly thought I would never get back to a career and if I did, I would forever start over at entry level positions as moving 2-3 years was our norm.

With my background in event planning, I tried to find ways to channel that knowledge and expertise. I launched a Party in a Box business which had a lot of potential but unfortunate timing (2019). Parties weren’t happening for most of 2020/2021. Sadly, that venture was not benefiting us financially and I closed that door. I would be lying if I said I didn’t feel like a failure. I felt like I failed at being able to have a career and then I failed at trying to create one for myself. I felt even more trapped due to COVID and it was only adding more years of blank space on my resume. We moved, again, this time to Kansas. My daughters were old enough to start school at this point. I was determined to figure out how to create a job for myself where I did not have to have the anxiety of needing to call out due to a sick child, quit due to an unexpected move or ask off when my husband had a rare long weekend off that we could take advantage of.

I played around with different ideas. I dabbled into offering virtual wedding planning services (riding the high of all things virtual post COVID) and eventually landed on becoming a virtual assistant, specifically serving the wedding vendor industry. I not only knew the industry, but it was my passion. If I couldn’t do exactly what I wanted, I wanted to work in the same space. Knowing I could easily do the administrative tasks required, from home, felt like a good place to start. I never considered working for an agency. I was always focused on creating my own brand, my own business and being my own boss. I needed that freedom in the life that we live.

I invested in a course (another risk after having already lost personal investment from my flopped party in a box business) and officially launched Aspen House VA in October 2021. I received my first client almost immediately and was surprised when I was booked to my personal capacity in just a few short months.

Being an administrative assistant combined with my love for all things logistics quickly branched into me specializing in system set-ups, system strategy and overall project management for various wedding and creative professionals around the world. I’ve worked for luxury stationery designers, wedding planners, photographers and other creative entrepreneurs from California to the UK. I’ve even made relationships where I have acted as a freelance planner for a company based out of Kansas City and when able, have been able to do what I truly love, planning events, in person.

The risk I took to put myself out there, again, and possibly fail, again, was not lost on me. My days are spent working between school drop off and pick-ups, doctors appointments, answering emails at the playground and taking my computer with me on road trips while having to hot spot from my phone-but I’m doing it. The military spouse life gave me obstacles I didn’t expect yet I managed to dust myself off, time and time again, and create something from nothing. For that alone, I have never been more proud of myself.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I grew up going to the grocery store and would purchase wedding magazines in order to cut out pictures and create inspo boards. Lot’s of little girls do this for their dream wedding though, right? Right, except I was not planning MY wedding-I was just planning weddings. While people always assume a wedding planner is equivalent to a designer, my love for planning is the logistics. I geek out over a good timeline. I love the puzzle pieces I have to put together to make a day come together seamlessly. Knowing that this type of job was not working with the life of a military spouse, I found a way to channel that same logistical love in the online world by offering my knowledge as a virtual assistant, system strategist and online business manager.
I offer various services to wedding professionals. I can serve them as an administrative assistant by helping create their own timelines, reconcile with vendors, onboard new clients, or set up their own backend CRMS or project management tools in order to help make their client experiences streamlined and organized.
I’m most proud that I have found a way to do what I love in all aspects of my business while also maintaining the life that is required of me at home as a mom and wife of my husband who serves as an active duty officer in the military. This is reflected in the work that I produce. I not only know the industry I am assisting my clients with, saving them hours they may have to spend training someone on the subtleties that come with every niche, but I’m truly passionate about it and will not settle for mediocrity.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

The idea that “you can’t start until you’ve got it figured out” will hold you back more than it will help. Sometimes, especially as an entrepreneur, you have to just go for it and figure it out along the way. That was a hard lesson for me. If I was waiting until I had my entire service offerings figured out, I would probably still be in pre-launch mode. My services have changed many times over the last few years. They change based on what is needed industry wide, what I find joy in providing and what’s simply just not working. If I see a need, I offer the service and work the kinks out as I go. Otherwise, I’d never be in go-mode.

How about pivoting – can you share the story of a time you’ve had to pivot?

I feel like my entire career life is one giant pivot. After letting go of the dream of a traditional job once becoming a military spouse, I pivoted to creating a job for myself. My business actually started as a virtual wedding planning business. I wanted to help couples that could not afford traditional planning services by offering guidance in the planning world. I wanted to help them search for vendors, review contracts, make sure all details were accounted for, create timelines, confirm with vendors, create planning task timelines, layouts…etc. I truly thought this was a stroke of genius! This was until I found myself having to overly explain what exactly it was that I was offering and how it was different from traditional planning services to not only couples but to other wedding vendors as well. I was battling to get my message out to two audiences and it was mentally exhausting. Young, early twenties Amy may have had the drive to start this new vendor market but thirty year old, mom to two Amy who just wanted to get to work and be in the industry she loved decided it was time to pivot and leave the trailblazing to someone else. Maybe that’s not inspiring to some but sometimes, it’s nice to see someone succeed that didn’t necessarily trail blaze their way into success. I feel like my sense of past failure has come from the idea that success is only reached if you’re featured on a top 10 list or forming a multi million dollar empire. The reality is success is different for everyone. For me, being able to stay home with my kids, provide financially to my family in a business I started myself, all while working in the industry I love, as my own boss, is success.    

Contact Info:

• Website: www.aspenhouseva.com
• Instagram: https://www.instagram.com/aspenhouse_va/

Image Credits
Kathryn Jones Photography Hold You Me Studios