“I’m about to send this email. Does it sound rude?”
A fellow freelancer in the live events world showed me an email he was going to send in which he’d ask for a raise.
“I don’t think you sound rude, but you sound unsure of yourself or like you think you’re being treated unfairly. Let me give you an example of what you could say.”
I could immediately see the problem. He boxed himself in as someone that needed to ask for permission or a favor, instead of positioning himself as a leader and a collaborator who deserves to be paid accordingly.
This is the moment I realized there was so much overlap between my years as a freelancer and my new experience as a business owner.
I spent 14 years as a freelancer in the live events industry before I made the leap to start my graphic design business. My years as a graphic designer might be few, but in reality, I’m using skills I’ve been honing my whole life. Fresh-out-of-college Leanne wasn’t ready to be a business owner. I needed that tangential path to bring me to where I am today.
Here’s how my experiences in live events prepared me for so much more.
How it all started
I started out in the live events industry at age 16. My local performing arts center, the Zeiterion Theatre, had an apprenticeship program in the summer for high schoolers to get real experience doing technical theater. My mom said, “Here, go do this,” and the trajectory of my life was forever changed.
By the end of my first summer, the technical director of the theater was asking me to come back to work the schooltime shows that came through. Soon, I was working every show, and I couldn’t imagine doing anything else.
Eventually, one of my co-workers asked me, “Why aren’t you working for this other company?” So, I signed up to freelance with them, and wow! I had no idea what I was missing until I finally worked somewhere besides the theater! I finally had access to all the extension cords I could ever need (which was a constant struggle at the theater), and I started making way more friends in the industry.
From there I received more suggestions: DON’T work for THIS company, DO work for THAT company. Since I was getting conflicting suggestions, I decided to try everything.
I learn by doing. People told me what to pursue and not pursue, so I decided to try everything and see for myself.
I decided I couldn’t let anyone else tell me what was good for me. I needed to experience it for myself. Somebody else in my same position could try the same things and come to a totally different verdict about what they like and want to pursue.
As I’ve coached other freelancers, I remember not everything is for everybody, and everyone gets to create their own path. It’s not helpful to have someone telling you what you “should” be doing.
Here’s what is helpful:
- Sharing information – “Here’s how this works…”
- Sharing experience – “Here’s what happened for me…”
- Asking questions – “What are you most worried about here?”
- Being a cheerleader and reminding people of their worth – “That’s awesome! You totally deserve this raise.”
One of the controversial topics that I’ve always received lots of opinions about is union versus non-union work in the live events industry. I’ve felt a lot of discord among people who see one way as right and the other as wrong. The majority of the people I knew were strictly on one side or the other. Was I wrong for doing both? Should I pick a side?
Now I see that my bilateral thinking is part of my personality and one of my greatest strengths. I see the pros and cons of all sides of an argument. And I know that there isn’t one choice that is always 100% correct. I enjoy a lot of different things. Variety keeps me engaged and satisfied.
This drive for freedom and variety has made the transition from freelancer to business owner a logical jump. If you had asked me years ago, I would have said I would NEVER start a business, because it sounded like too much responsibility and pressure. But in reality, freelancer and business owner are just two sides of the entrepreneurial coin. Both want freedom and agency.
Working for a variety of companies is one of the reasons I have always loved freelancing and why I’ve never taken a full-time job. I don’t want to commit to just one thing forever. I want the freedom to try many things.
Saying no is difficult because I can see the benefit in any decision.
When I started out, “No” wasn’t really in my vocabulary. I was in an experimental phase, tasting a little of everything. I had already learned not to let anyone else decide what was right for me. So, if an interesting opportunity came up, I always said yes.
I remember the day that that changed. The day my worth became so clear to me that I knew it was time to be more selective.
If you walk into work, and they say “Oh, thank god you’re here,” it’s time to raise your rates.
I showed up to work at the Museum of Fine Arts, ready to set up lighting with other freelancers I’d known for years. When my lead saw me, he said “Oh thank god, you’re here!” and handed me a radio.
I was then given a few freelancers and very little information and sent up to the balcony to set up the lighting there. I recall lots of running back and forth, asking clarifying questions to my leads, and relaying information and instruction to the other workers.
I showed up expecting the low-responsibility role I signed up for, and I ended up being given the responsibilities of a higher-paying position.
I rolled with the punches because that’s what you do in live events. And don’t worry, I brought my concerns to the company and was compensated for the responsibility I was given. But I learned a valuable lesson: I was worth more than I was giving myself credit for.
From that day forward, I never took an entry-level type position with that company again, and I started asking for more leadership roles. There were certain people I knew who I’d NEVER see in those lower roles. If I saw that person on a job site, I knew they were a lead. I wanted people to start seeing me that way.
This mindset has helped me so much as a business owner. People will respect my business to the extent that I respect it. Just like when my lead said, “Oh thank god, you’re here,” when I receive praise and see results in response to the work I do, I gladly accept the validation that I provide great value to clients who need it. And I get to make business decisions accordingly.
No one is responsible for my success except me.
This new standard of operating took over my entire freelancing philosophy. I stopped taking lower-level jobs when I knew I brought much more to the table than the other freelancers in those roles.
I realized that if I wanted leadership positions, I had to ask. I had to make sure that the people who made these decisions knew who I was. I knew if they saw me on the job, they’d know I rose above the rest and was definitely leadership material. But if they didn’t even get the chance to see me in my element, how would they know? They wouldn’t. Unless I asked.
As I got more selective about the work I took, I started to tune in to how I FELT on certain jobs. If the idea of saying ”Yes” to a job made my stomach sink and filled me with dread, I recognized that job was a “No.” I gave myself permission to say “No” when that’s what I truly wanted.
I had my own way of assessing different jobs. Many of us evaluate these many aspects of a job, but we come to different conclusions about what they mean to us.
These are the variables I considered:
- Location – Where is the job? Is it far? Do I like the job site, or is it a difficult place to work? Is there free parking?
- Schedule – What time is the call? Can I get a reasonable amount of sleep and get there on time? Will I get a reasonable amount of sleep the night after?
- Pay – How much does it pay? What is this company’s policy on minimum hours paid? Will I make a reasonable amount, taking all my expenses into consideration? Is this 1099 work or am I on payroll? (Are you illegally being hired as an independent contractor, when you should be hired as an employee? Read more here.)
- People – Who will be there? Do I trust and respect the leads? Will there be friends there to make the day feel fun? Will there be experienced workers there to make the work easier and less stressful?
- Company – Do I like this company? Do they plan well? Do they cover any expenses, like parking and meals? Do they pay into my retirement?
- Event – Have I worked this event before? Does my answer to that question make this job feel easier or harder?
- Potential – Is this job going to open up opportunities for me? Do I get to try something new, learn new skills, or meet new people?
- Gut – What’s my gut feeling about taking this job? Opportunity or dread? Excitement or resentment?
I started responding to work requests based on my answers to these questions, now that I had enough experience to know the answers. Being able to weigh the relevant pros and cons, as well as tap into my gut feeling, has continued to help me make better career decisions in any industry.
It became so important to zero in on what was important to me and what I was looking for. I wanted enough rest and fair pay. I wanted to work jobs that felt good and didn’t bring on anxiety.
I could no longer sit in the backseat and hope I ended up where I wanted to be. I needed to get in the driver’s seat. I needed to be clear on my desired destination, and I needed to actively choose to go in that direction. It is this innate drive that makes me a successful business owner.
I had to start saying “No” in order to make space in my life for more “Yes.”
When my schedule wasn’t packed to the gills with low-paying, soul-sucking work, I had the chance to say “Yes” to new, exciting opportunities. Can I go to LA for a week? Hell, yeah. Program lighting for this show that just came up? I’m in.
But when opportunity knocks… Listen to your gut and be ready to shift.
The advancement of my live event career has been a mixture of hustle and opportunity. I’m tempted to say some things were serendipitous, but that would be severely underplaying my years of experience and dependability. (Not today, imposter syndrome!)
It was a normal August day, before another full-steam-ahead September that I received a call from my soon-to-be, he-denies-it-but-it’s-true mentor, Marco. He was asking me to be his Assistant Production Electrician with the Boston Lyric Opera.
In case you haven’t gathered by now, I took my freelance career very seriously. I was meticulous about what work I took, and I very rarely called out. But saying “Yes” to Marco would mean saying “No” to nearly everything I had lined up in September.
There were two huge pros to saying yes: 1. It would increase my earnings with the union, which would give me more security within my Local. And 2. I’d be taking a leadership role with a well-known company. Great for my resume, as they say.
I remember saying to people “This just fell in my lap! I don’t know how this happened!” because this opportunity felt so unexpected. I didn’t feel like I earned it, because I wasn’t specifically working towards it. But, my trusted colleagues reminded me, “You DID earn this. You’re a smart, skilled, hard worker who knows what she’s doing.”
I’ve seen this happen in my graphic design business, too. Opportunities would arise that I wasn’t looking for, but they wouldn’t have shown up if I wasn’t already laying a strong foundation in my business and showing up every day.
It Pays to Be Personable
Throughout my whole freelance career, I’m constantly reminded: we need each other. From first hearing from a co-worker that I COULD freelance, to my first time working at the BCEC (the Boston Convention and Exhibition Center) and having NO CLUE where to go, to being offered a job with the BLO and needing to ask ALL my friends to cover my other shifts–people are the reason for my success.
This is a both/and situation. No one is going to advocate for your success except you. You need to pursue what you want and ask for what you need. AND. It’s all in who you know. Be a friend to everyone. I certainly had times when I thought I was talking to just another stagehand, and it turns out I was talking to the boss. You never know who you might be talking to and who that person might end up being down the road.
This is certainly true in my life as a business owner. Meeting people and showing up to networking events has done more for my business than an Instagram post ever will.
Picasso said it best
There is a story about Picasso quickly sketching a drawing on a napkin. He offered to sell it for a million Francs.
“But this only took you five minutes!” said his patron.
“No. It took me 40 years to draw this in five minutes,” Picasso responded.
My 15+ years of freelancing have prepared me for owning my own business because now I…
- Try new things, learn from my experiences, and want the freedom to choose.
- Can see the pros and cons of any situation.
- See the value I bring to the table and am willing to advocate for myself.
- Ask for what I want, instead of simply hoping I’ll get it.
- Know that I need to say “No” to make room for more “Yes.”
- Am ready to pivot when the right opportunity arises.
- Recognize that I am more successful when I value connections.
However second nature it may seem, everything you do in your career is the result of years of honing your unique skills. You bring all your experience from all your past jobs to the work you do today. Don’t discount that.
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