Meet Sarah Klegman | Creative Brand Strategist & Storyteller

We had the good fortune of connecting with Sarah Klegman and we’ve shared our conversation below.

Hi Sarah, we’d love to hear more about how you thought about starting your own business?
It happened really organically. I’ve always been a creative writer, then as my career grew and became wildly diverse, it provided me with a skillset that allowed me to work with ALL kinds of folks while leaving space to pursue my own artistic passions.

My career started in the comedy business – I was a manager and producer, looking after comedians, writers, and performers. I learned how to support individuals in developing their unique voice and brand and how to sell them to all kinds of creative distributors – from studios to comedy club owners, production companies to publishing houses. I honed the art of understanding audiences and communicating artists’ value and potential for success.

When I had learned all I wanted to from that industry (and admittedly burned out), I moved to the tech space, taking on the role of Head of Creative Content for social media platforms as well as a wide range of startups in their infancy.

From the outside, that may seem like an unconventional jump, but it applied a similar skillset: understanding audiences, how to curate engaging content that resonates with audiences, and how to design a powerful brand voice for the apps themselves.

With that career jump, my office went from a cubicle in a dry office building to a beach house on the Venice boardwalk filled with multi-hyphenates: The Head of Operations who was also a music producer. The Head of Development who was also a performer. The Coordinator who founded a neon company.

Within the walls of that beach house, I found inspiration to do the same – to pursue my many passions without the fear of needing to be easily defined. I started a podcast, I began publishing my writing, I worked with a Jewish women’s wellness organization, and I performed on all kinds of storytelling stages.

What started a recipe blog turned into co-founding a challah bread company where I wrote and designed a memorable brand with a strong voice. We weren’t just a bread company – we were a wildly creative brand that partnered with the likes of Buzzfeed and PBS to make joyful content. We put on fantastic tasting events and offered classes, which eventually led to me going on international tours to teach, speak, and do live podcast recordings all over the world.

When the beach house eventually closed its doors, I had built a reputation across many industries that opened doors to all types of opportunities as a creative consultant. I worked with newly launched companies to help design their brand voice, coached individuals pursuing their creative dreams, and eventually created opportunities that allowed me to flex all my skills and passions.

When the pandemic started, one of my many clients (a multinational AI startup in a niche industry) asked me to join full-time and I welcomed the stability during such an unstable time. I ended up spending five years helping to build that brand… and then accidentally found myself in a C-level creative role. I learned a how to operate at a very high level brand design and organizational management. After leaving that role (also, admittedly, due to burnout – more on that later), I went happily back to my creative consulting business – this time with an even broader list of offerings.

Today, I get to choose which clients I work with and how I expel my energy while controlling my own schedule. I give myself time to play with my writing in my own voice, to tell stories on all kinds of stages, and to work with other artists.

What’s one piece of conventional advice that you disagree with?

People talk about the importance of validating market demand before building anything. I believe that’s partially important in the startup space (at least when it comes to proving your company’s potential for success to investors), but I don’t think it’s worth paying much attention to with creative endeavors.

While understanding industry trends is helpful, you can’t let it be the only guide for what you create. Having a strong voice is about being unafraid to break convention, not catering to others, expressing your own identity, and authentically finding your audience. More often than not, that will create a foundation for long-term success by attracting folks who have a more personal connection to you and your work.

Risk-taking: how do you think about risk, what role has taking risks played in your life/career?

Risk-taking is absolutely necessary. I’ve witnessed first-hand that most people – from CEOs to A-list stars – had no idea what they were doing when they started. Heck, most of them still don’t know what they’re doing. That’s how you learn and grow. It’s that classic piece of advice: If you wait to begin until you’re ready, you’ll never get started.

What habits do you feel helped you succeed?

Staying curious and authentic. Curiosity pushes me to dive into things I know nothing about, which is the foundation for growth. Vulnerability helps me build authentic connections because being honest about who I am inspires other people to be honest about who they are.

Oh, and having a great therapist.

What is the most important factor behind your success / the success of your brand?

It all goes back to authenticity. No matter the industry or individual, I show up as myself. Sure, I may emphasize specific traits, but I’ve learned the value of staying true to who I am. I’ve experienced the pains that come along with pretending to be someone I’m not, and I can never go back.

What’s the most important lesson your business/career has taught you?

Be unafraid to be unconventional.

Work-life balance: how has your balance changed over time? How do you think about the balance?

It’s about letting myself explore my passions without letting them take over my life completely.

When I was working as a manager and producer, I threw my whole self into it. I was at the office from nine to five and then in comedy clubs until midnight or later. I spent weekends reading scripts or networking and next to no time taking care of myself.

And then I burned out.

When I was helping run a startup for five years, I got a bit better about self-care, but I still ended up burning myself out… again. After that, I took nearly a full year off to recover.

I learned that no amount of money or success is worth running myself ragged like that. Today, I only choose clients who are great to work with and who will give me opportunities to keep learning. I create strict contracts with clear boundaries that protect my personal life. And I take a hell of a lot more vacations.

Why did you pursue an artistic or creative career?

I’ve always loved what it feels like to provide an escape, to entertain, and to connect with people. I’ve been writing and performing since I was a kid. Some of it may have come from being the youngest sibling and learning that comedy is a great way to diffuse tension.. and save myself from getting grounded.

As I got older, my identity evolved, too. I’m queer, partially deaf, neuro-diverse, married to a transgender US Soldier, and Jewish. I have the opportunity to create common ground for a wide range of identities. Stories that help people understand hearing loss and dispel stereotypes. Bringing conversations about queerness and the value of diversity to conservative audiences. Showing people that being neurodiverse can be a strength. Doing work like this is not only healing for the world but healing for myself.

What are you inspired by?

There’s this great story that Jim Carey tells about his father. He was a musician and comedian who had dreams of being an entertainer but decided to take a reasonable job to support his family. Then, one day, his dad was fired. He watched his dad fail at something he didn’t love. So he thought, if you can fail at something you don’t love, you might as well take a chance to follow your dreams.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Brunch would definitely be involved – there’s an abundance of fantastic breakfast burritos and egg sammies to be had. Driving along the coast and finding spots to dolphin watch. Going to comedy shows. Going to theme nights at dance spots. Wandering into cute shops to peruse chotchkes from local artists.
That said – I wouldn’t stick to a rigid schedule. Leaving room for spontaneity has resulted in countless surprising and memorable experiences.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My mom is my biggest fan. She always supported me in whatever passion I pursued, no matter how unconventional. She’s there for me through every win and every loss. Growing up, I watched her fearlessly speak up for injustice by educating people, which inspired me to always stay true to my voice. She reminded me of who I am in times when I had gotten too far away from myself. Her love and encouragement is hugely responsible for me growing into the person I am today.

Linkedin: https://www.linkedin.com/in/sarahklegman/