In this episode of Voted Least Likely, we dive into a question that has kept me up at night: Do you need to be an optimist to succeed in business?
This topic was sparked by a moment at a recent entrepreneur event — everyone in the room seemed effortlessly confident, “delusionally” optimistic, and absolutely certain their success was inevitable. Meanwhile, I was quietly wondering why I felt so out of place… until it hit me:
I’m a pessimist.

And in the entrepreneurial world, that can feel like a dirty word.
In this episode, I unpack what it's like to build a business when your default setting is assuming the worst. I talk about:


Why optimism is so heavily associated with entrepreneurship


The unseen advantages of being a pessimist (yes, there are some!)


How pessimism can sabotage your next steps — and how to work around it


The myth that you need unwavering confidence to succeed


My own early days building Leah Yard Designs, and why I genuinely thought I’d fail (but kept going anyways)


Why not fitting the stereotype doesn’t mean you’re doing it wrong


If you’ve ever felt like you’re the only one who doubts yourself, prepares for the worst, or secretly thinks everyone else must know something you don’t, this episode is for you.
We explore whether success actually requires optimism, or if there’s room in entrepreneurship for the rest of us: the over-thinkers, the realists, the cautious dreamers, and the “hope for the best, prepare for the absolute worst” types.
Listen in to hear why your mindset — optimistic or pessimistic — might be exactly what your business needs.

Connect with the Voted Least Likely Podcast:
www.leahyard.com
IG: @leahyard
TikTok: @leahyard

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