We’re excited to introduce you to the always interesting and insightful Josef Anolin. We hope you’ll enjoy our conversation with Josef below.

Alright, Josef thanks for taking the time to share your stories and insights with us today. How did you learn to do what you do? Knowing what you know now, what could you have done to speed up your learning process? What skills do you think were most essential? What obstacles stood in the way of learning more?

I learned to do stand-up through trial and error. The first show I ever did was at a black box theater in SF, where everyone on the show was a participant in a 10-week comedy workshop. Our friends and family were our audience, and they all patted us on the back and said we were great. We all thought we were amazing. About 4 weeks later, some of us from that workshop did another show with an audience that did not know us and had no qualms about letting us know we sucked. Trying to reconcile those two experiences at the time basically put a chip on my shoulder, where I wanted to prove that I WAS funny. Long story short, it took a lot of grinding at open mics for me to start better understanding things like joke structure, how to take personal stories and experiences relatable to those who may not have those same experiences, and developing a strong confident stage presence.

Some things I could have done to speed up my learning process would be to practice multiple forms of comedy/joke writing. I tend to tell story based jokes, and when you’re starting out, or you go to a new city where the open mics only give you two and half minutes, which meant that I could probably only tell one long story, and if that bombs, yuck. Thats not a good feeling, but it taught me to take what was like a 5 minute bit, and whittle it down to one and a half. Cutting the fat is essential.

I truly think my biggest obstacle has been myself. I have peers who have bought themselves houses with comedy and support their families with it. I didn’t come into this with the right perspective and work ethic. I wish I had taken the career part of “comedy career” more seriously.

Josef, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I got involved with stand-up comedy through Bindlestiff Studios, a Filipino-American theater in the SOMA district of San Francisco. At the time I was doing A/V work for the theater and one day I went in thinking I had a rehearsal but it was a stand-up comedy workshop. After apologizing for interrupting and about to make my exit, the person running the workshop, Kevin Camia, (who opens for Ali Wong and Sheng Wang) invited me to stay. The workshop culminated into a show attended by our friends and family, and everyone was supportive and said we were great. Then a few weeks later, a few of us did another show in SF that wasn’t our friends and family. They were less supportive. And I guess it put a chip on my shoulder, as I wanted to try again and prove that they were wrong.

From there, I started showing up to open mics, mainly The Brain Wash in SF on Thursdays, and started to get to know my fellow Bay Area comedians. Howerver, it wasn’t until I was taking care of my Dad who was diagnosed with cancer, where I became his primary caregiver, that I realized how much I loved doing stand-up. It really helped me focus and channel my energy into something positive, and it was nice to be around laughter in a somber time. After his passing, I promised myself that I would take the craft more seriously, and I began showing up to either a mic or a show every day I could. I’ve been doing that every since.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

I’m not sure that only “non-creatives” can relate to this, but “creatives” tend to not generally travel the typical path many are expected to follow. College, career, marriage, kids… That tends to be the typical order of things, and the later you do, or DON’T do those things, the more friends and family tend to worry, and voice their concern for your well-being. And it can make you doubt yourself. It might start to feel like the clock is ticking. Your friends or siblings are maybe going on their second or third kid, talking about mortgages, retirement plans. Your parents bugging you about grandkids, or your lack of an actual career, long term prospects, etc.

The question I had to ask myself is will those things make me happy the way that stand-up does? And sure, there may be merit to being realistic about being able to make a living through your creative endeavors, but that shouldn’t mean that you should hang it up. Being able to find a balance between the two is my main goal, but as far as needing to complete someone else’s life goals checklists, that not for me.

I think creatives get bogged down BY the creative part a lot, and the business aspect seems even more daunting to navigate sometimes. When that part becomes equally important, it’ll lead you to more successes, and maybe get your friends and family off your back. a little bit. Make it an equal priority.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

50 Cent book, “Hustle Harder, Hustle Smarter.” You can listen to it for free on Spotify.

Contact Info:

• Website: josefanolin.com
• Instagram: https://www.instagram.com/comedianjoe510/

Image Credits
Jim McCambridge