3 Things I've Learned from Working with an Assistant


Early this summer, I was sorting through my inbox when I came across an e-mail from a smart young lady named Maya. She expressed her interest in learning with me and helping out with events, and I couldn’t have been more excited to bring her into my one-woman shop! The prospect of having assistance was great, but I was honestly more looking forward to just sharing my knowledge with this eager college student. From planning Art of the Journey events to client work to branding, I hoped to teach her whatever I’ve picked up over the years. However, it’s funny how things work out. Looking back, it’s obvious to me that I’ve learned equally as much (or possibly more) from working with Maya, as she has from me. True story. 

If you’re toying with the thought of hiring an assistant, intern, helper, etc., read on and I’m sure you’ll have an answer shortly! Here are the top three things I’ve learned from working  with an assistant.

1. How to clearly explain my business and put the present into context

Because I’d worked alone on my projects for so long, I never had to explain everything to someone. Have you ever done this before? Sure, I was used to coffee meetings where I gave an elevator pitch of what I was working on, but putting my work into full context to someone was new. Particularly in hiring, I made sure to give Maya the full story of how both Art of the Journey and Events by AW started, where I was currently struggling and thriving, and what my short-term and long-term goals were.  I’ve learned from my own work experiences that to be productive you need to see where you fit into the picture, so I wanted to provide Maya with the whole story.  It was a self-reflective exercise that I didn’t know I needed. After being so clear for someone else, things also became more clear for myself.

2. How to delegate efficiently

This is the biggest lesson for me! After confirming Maya was the one (lol, romantic), it was time for me to determine what her duties would be and how, logistically, we could work best together. I considered her help with the time-consuming areas, which for me were research, social media strategy, shopping, setting up events, and administrative tasks. This freed me up to do more planning, networking, relationship-building, and big-picture strategizing. Next up was figuring out how we were going to communicate. I was, again, alone for so long that I had essentially no structure to how I worked – how could I make it clear for her? Because events are project-based and not consistent (yet hehe), I knew providing Maya an estimation of her weekly hours was not realistic. I decided on a long, weekly e-mail where I detail recent happenings and action items for both of us. We mostly work remote and play a few things by ear because of the nature of the industry. It works well for us!

3. I learned what kind of leader I am

Finally, I’ve gained valuable practice on how to lead. Even though we are a tiny team, I’m thoughtful of where Maya personally and professional wants to develop, how to keep us motivated, and how to express my appreciation! I like to think I’m doing a decent job, but I guess you can ask Maya her opinion 

I know one day Maya will move onto bigger and better opportunities, but this experience is one I’ll always be grateful for!