@sydwingold on how committing to the bit changed everything

Syd Wingold’s Top Tips for Creators:

• Give yourself time
  It really took a long time to experiment to see what hit with my audience, what performed, and what didn’t. I tried not to let it get me down because that’s the name of the game with this career.
• Embrace the cringe
  You have to get over that hurdle to get to the other side. It’s only cringe until your stuff starts performing. The people who think you're cringe in the beginning, when they see you succeed, then it becomes cool. The dynamic shifts.
• Spice things up with something unpolished and spontaneous
  I like to do a mix of spontaneous and planned content because I feel if I’m only known for one thing, people come to expect that. So every now and again I’ll throw in something [unpolished] that's not the norm, like me making a Mother’s Day card. It keeps the audience on their toes. They're seeing something that's not what they normally follow me for, but they’re interested to know more.

Syd Wingold is a Toronto-based creator known for her costumes, characters, and unique take on comedy. After quitting her corporate 9-5 in finance, she’s become a full-time creator, amassing over 1M followers. Whether she’s doing her best burger impression or taking followers behind the scenes of her wedding, nothing is off limits for Wingold: she’s committed to the bit.

We sat down with Syd to learn more about her fearless approach to creativity, strategies for approaching new audiences, and how she stopped worrying and learned to embrace the cringe.

How did you get your start as a creative?

I was working a traditional corporate 9 to 5 as a financial analyst before I became a creator. Content creation was always something I did in the background as a fun creative outlet for my very stressful corporate job. I kind of started out just experimenting with a bunch of different content forms.

My first claim to fame was I would roll myself into a blanket on the floor, and that was my first viral video that really let me hit the ground running. From there I experimented with other costumes.

How did you find the courage to jump from a full time corporate space into an entrepreneurial, creative space?

Honestly, it was very scary for me to do that, because before entering this realm of my life I was a very play-it-safe person. I basically gave myself a year to see if I could actually make a living doing this. I’m so happy I took that risk on myself because it’s been so rewarding.

Did you know this was going to land? There’s a lot of room for self doubt to creep in when doing comedy.

When I first quit my job and really decided to do this, I told myself that I’m going to post something every day. I’m going to try every different content style in the book, post something different without trying to make it perfect, and see what lands.

Do you feel like having a regimented schedule ultimately helped you be more creative?

I find I’m my most creative when I give myself a very strict, regimented schedule. I know with some creators it’s the opposite, but I’m always working one or two weeks ahead of myself. So what I’m posting tomorrow is something I may have filmed two weeks ago. Getting in that habit of constantly being creative helps new ideas flourish.

Do you have separate strategies for your existing audiences vs. new audiences?

I definitely have a bunch of series that my audience has come to follow me for. I’m always trying to hit new audiences by coming up with new series that can keep things fresh and interesting.

How does your content on Instagram compare to other platforms? What purpose does Instagram serve in your overall platform mix?

Instagram for me feels like the platform where I can connect with my audience. It’s the one platform where my followers really get to know me as a person.

Because everything I do is comedy through the lens of different characters, I don’t share a ton of my personal life, but Instagram is the one platform where followers get to follow me through things like my wedding content and [other snippets from my personal life]. I really feel like I connect in a different way. I know who my followers are, and I respond and interact with my followers, so it feels the most personal.

What tools or features do you use?

Stories are a big one. I’m always sifting through message requests to interact. So many followers are like, ‘Oh my God, you responded!’ I see all of my DMs; I’m always in there. Also my broadcast channel: if I need a quick response to a poll or something, I’m pretty active in that. And responding to comments to my reels. These tools really allow me to build a community that’s unique to Instagram.

I have been dabbling into trial reels a bunch the last couple months, and I’ve seen growth from it. Gaining followers comes in waves for me, and sometimes when there’s lower peaks, I’ve been trialing them quite a bit.

How do you define success beyond the metrics of likes, views, followers?

Progress and success for me honestly is just engaging with my community. It’s the coolest thing in the world to know there's over a million people who log on every day and want to view my stuff.

As long as I’m proud of the work I’m putting out, the numbers are just an added bonus, because it’s so easy to get down on yourself about numbers.