By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Yosef Haiem | Youtuber

I would say risk is one of the most important aspects of making a social media business successful. As you take more risks and spend money of things you are unsure to work, it will either pay off or fail. If it pays off, great, and if it fails, that’s just part of life you get back up and try something new. Read more>>

Li Mia | filmmaker

Hate to admit it, but the whole risk thing is almost inevitable in life. As a filmmaker, risk exists in every moment. Starting with the pre-production of the script, to the beginning of the shoot, there is a huge cost of time and money, and the post-production of a portion of the movie means an equally huge cost. These are all risks. Read more>>

Rose Mina | Actress & Writer

I feel as though within society at large, we have made things just about as hard and complicated for ourselves as possible, all while ignoring innate passions or dreams and letting fear win. However, it is often rebellious to take risks in the hopes of bringing your dream career to life. Read more>>

Krysta Fauria | Entertainment Journalist

I like to think that a willingness to take risks, be them personal or professional, has been a defining feature of my life. And while some of the risks I’ve taken have had obvious payoffs, like when I said yes to moving to DC for my first full-time job with The Associated Press, others have not. Before I started covering entertainment, I left AP to pursue a PhD. Read more>>

Kayla Raelle | Actor, Writer, Magic Maker

Ah, the complexity of risk taking. Being that risks can bring either great adventure or great endangerment, I find myself more often than not boiling them down to one thing: intuition. How’s my intuition reacting to the idea? Crumby? Let’s unpack that. At peace? Let’s investigate why. Once I take the time to sit with these feelings and discover whether or not fear or love is the thing either holding me back or catapulting me forward, I choose love as often as I can. Read more>>

Amanda & Bella | 2 Sluts That Never Shut Up (podcast)

We decided to start a sex positive podcast at an age where women are told they should have already gotten married and settled down, in a society that sexualizes young girls, while simultaneously shaming women for embracing their sexuality. Doing this podcast is a risk in it and of itself, but it’s a risk worth taking for us. Read more>>

Alyssa Hill | Art Director for Television and ceramicists

In my life I have taken risks at every step. Leaving for film school in North Carolina was a big risk. UNCSA was not a well-known school at the time. In fact, it was not even part of the university system at the time. It was an art conservatory. After graduating in 2007, I made the choice to move to L.A. and try to make a career in the art department. Read more>>

Parish Mandhan | Photographer & Filmmaker

Risk has always been a cornerstone of my photography business. I began my journey into photography at a very young age without any formal background. Choosing photography as a career was a significant gamble, given that it’s one of the most expensive hobbies to turn into a profession. Despite the challenges, my passion for photography drove me forward. Read more>>

Amanda Huang | director

Taking creative risks is a vital factor in the film production process. It excites me as a director to make bold decisions and try different ways to tell the story. While being on set, many unexpected situations often arise, which can sometimes cause inconvenience for the crew. However, embracing those risks can also lead to pleasant surprises.  Read more>>

Donterell McDuffie | Music Producer, Author, Actor, Composer

There’s an old saying which I love. “Fortune favors the bold.” I’m not quite sure who said it, but for me and many I know, this is true. Well calculated risks bring the highest rewards. This is true for stocks, gambling, and careers (if done well and appropriately). I think about risks as unknown stakes for unknown rewards. Read more>> 

dannirose☆

Risk has definitely been a driving force in what has got me here today. I think the biggest risk I took was pursuing music after high school. I applied to a small handful of universities and I ended up getting accepted to Western Washington on a near full ride scholarship with no requirements to the school. Read more>>