• Aerial Cheryl

Top 5 things I’ve learned in my first year as a business


1. I don’t know as much as I thought I did. This comes down to some specifics and you don’t know what you don’t know. Meaning that if you haven’t experienced doing something before, there are bound to be aspects of it that you aren’t aware of. And by not even being aware of them, you aren’t going to know everything about them right away.

  • I’ve worked a lot of corporate events as a contractor. I’ve observed the interactions between organizers and clients. I’ve read through all of my various contracts pretty thoroughly. So, I thought I knew what I needed to know about booking a gig and hiring other contractors. Especially because the first couple I did went really smoothly and there were no hiccups. Then the event that had some hiccups happened. I mis-copied some elements of the contracts that left me much more responsible in the event of cancellation than I was comfortable with and some very strong hints of cancellation were floating my way. Gratefully, the event came together the day before and everything happened beautifully.

2. Marketing!!! (See #1)

  • I figured having a business account on facebook and instagram along with a fully functional website would be the trifecta of marketing miracles. Apparently, I’m a little late to the game for it to be that easy and I’m still really working on marketing and what will be the most successful for me. The consistency with which you have to post on social media and the quality of content that needs to be posted to gain traction can be overwhelming. Especially for someone like me, who really wants to add value to people’s lives and who spends an inordinate amount of time crafting most of my posts. Also, my schedule is always in flux and so I don’t always prioritize and make time for marketing myself and my business the way I need to for real growth.

3. It’s lonely

  • Because I do everything for the company, there’s hardly anyone around to bounce ideas off of or work with on projects. I’m grateful that I have an office set up at home where I can be productive and busy but even this introvert needs some interaction sometimes. I’d recommend finding another entrepreneur that you can meet up with at a coffee shop and just share a table with while you both get some work done and talk about your shared frustrations as well as your successes. Help each other stay accountable to your goals and celebrate what’s working well together.

4. Just because someone’s been doing it longer, doesn’t mean they’re doing it better

  • This one is important. I expected that I would learn most of my weaknesses and holes from my clients because they’ve been hiring contractors and hosting events for much longer than I’ve been booking them. And while sometimes this has been true, I’m pretty sure one of my events, was the first one this client had done. Which had it’s bonuses: I could really utilize my strengths and I had the opportunity to teach them what hiring a professional contracted performer should look like (in my opinion anyway). I also expected other entertainment companies to shy away from me or to have a better handle on how to run things. This is one area where my experience of working with a lot of other companies has come in very helpful. I know what really worked for me as a performer and what made my work extra challenging. I do my best to communicate clearly and provide as much as I can to my clients and to the other performers when I have a chance to bring them in.

5. I know more than I thought I did

  • While I might not know as much as I thought I did when it comes to the specific details of contract writing or insurance, I learned a lot from other jobs I've had and from the variety of companies I've worked for in the past. This, coupled with pretty good instincts and continued education, will lead to success and growth everywhere I have to courage to take a step forward.


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