//

“If you’re meticulously prepared you can still improvise, but if the plan is to wing it, you have no structure to fall back on”, with Paul Osincup

I had the pleasure of interviewing Paul Osincup, who is a speaker and positive workplace strategist who equips people with strategies to…


I had the pleasure of interviewing Paul Osincup, who is a speaker and positive workplace strategist who equips people with strategies to create work climates that are more positive, productive and fun.

A former university administrator and conflict resolution specialist, it’s Paul’s experience as a stand-up and improv comic that fueled his interest in using humor to enhance human performance.

Paul’s TED Talk, “Leading with Laughter: The Power of Humor in Leadership” has been viewed over 160,000 times and his work has been highlighted in Forbes, SUCCESS Magazine, and on his mom’s refrigerator. Paul is the President-Elect of the Association for Applied & Therapeutic Humor, an international organization dedicated to the study and application of humor in professional settings.

Thank you so much for joining us! Let’s show everyone you’re a normal human being. What are your hobbies, favorite places to visit, pet peeves? Tell us about YOU when you’re not at the office.

“Good idea. With the increasing success of AI robotics, it’s smart to start off letting everyone know I’m a human. I live in the San Francisco Bay area, so when I’m not working I love to fish off the coast in my kayak — anything from cod & halibut to a six-foot shark! (I let her go). I get to travel a lot for work but love to do it for leisure as well and just had a great trip to Thailand. I also love to hike and camp with my wife and dogs.

Can you tell us something about you that few people know?

“Not many people know that when I was 11 years old I got a cracked rib from getting punched in the chest… by a deer.”

Do you have any exciting projects going on right now?

“Fortunately for me I find being a speaker to be an ongoing exciting project. I’m constantly creating new material, learning about new trends and listening to what the needs of event planners and organizations are. Oh, and I’m writing a book. I kept telling colleagues I didn’t want to go on to get my Ph.D. because writing a dissertation sounded boring, and now I’m writing a book.

Many people say success correlates with the people you meet in your life. Can you describe two that most impacted your success and why.

“First and foremost is my wife, Kelly. I don’t think I really knew what dedication and strong work ethic looked like until I met her. She worked her way through nine years of post-graduate school to become a board-certified Veterinary Oncologist. For context, there are less people who are Veterinary Oncologists than there are NFL Football players. The hours and sacrifice she put in gave me a new appreciation for what it takes to achieve a long-term goal and be successful.

“The second one is a boss who I won’t name. This boss was negative about everything, had very high expectations for people without showing any signs of support, and had no sense of humor. I realized that everyone within the sphere of this supervisor was miserable in their job and was disheartened to see how one person could make going to work so miserable for others. Working for this person was when I realized I wanted to bring more humor, fun, and positivity to people’s work lives, so I quit and started doing what I’m doing now full time.


Leaders always seem to find ways to overcome their weaknesses. Can you share one or two examples of how you work outside of your comfort zone to achieve success?

“The first thing that comes to mind is to say yes to opportunities I know I’m not quite ready for. My entire career I would volunteer for opportunities, apply and accept jobs, and say yes when asked to situations in which I felt nervous or underprepared. I’ve found that the pressure and adrenaline to learn what I need to and perform at a high level pushes me. Most of my greatest accomplishments began as overwhelming new projects that made me nervous.”

The concept of mind over matter has been around for years. A contemporary description of this is having mental toughness. Can you give us an example (or two) of obstacles you’ve overcome by getting your mind in the right place (some might call this reframing the situation)?

“Humor is an underutilized mindfulness tool for this. For example, last fall my town of Santa Rosa, California suffered from devastating wildfires. I was evacuated from my house for a week, but luckily it was saved. Thousands weren’t as lucky. It was terrible. A day into it as I was at the store looking for breathing masks when they were all out, and many of us were leaving the store without the masks we needed.

“A little kid pointed to the Halloween aisle and said ‘Dad, there’s masks over there!’ — pointing at the Halloween masks. It made me laugh and it also reminded me that I should try to make other people laugh during this difficult time. I created a video that I posted in a firestorm update facebook group where I sang ‘Fight Song’ in 16 different character voices to cheer people up. A lot of people said it made them smile and just making it made me happy. Intentionally seeking humor instantly changes our mood and increases resilience. Here’s that video if you’d like to check it out: https://www.youtube.com/watch?v=ESp8Wed7ohg.”

What are your “3 Lessons I Learned from My Most Memorable Failure”?

“One of my first big failures was when I bombed in epic fashion at an open mic comedy night.

Here’s what I learned:

“Commit. There were certain jokes where it was imperative that I commit completely to the character and give 100% energy, but my nerves caused me to hold back which the audience felt. Always commit fully.

“You can’t over prepare. I was well-prepared for what I was going to do that night but didn’t want to go through it too much because I didn’t want to ‘over prepare’. I fumbled around and lost my place a couple of times because I didn’t know my material like the back of my hand. If you’re meticulously prepared you can still improvise, but if the plan is to wing it, you have no structure to fall back on.

“Have trusted friends. When I was done, I asked my friend Jeremy what he thought, and he said, ‘Pretty horrible, dude.’ He’s been my best friend for 30 years and I know he won’t B.S. me.


What unfiltered advice can you give aspiring stars regarding how to avoid common mis-fires in starting their career?

“Don’t be boring. Do anything you want, try new stuff, fail colossally, get rejected, etc., but whatever you do, don’t be boring. We’re in an age where there’s more content than anyone can keep up with and boring crap of any genre is the quickest to be ignored. See? This answer is already too long and boring, and you’ve started thinking about something else.

What is the best lesson you learned from your worst boss?

“I didn’t look ahead and see this question before answering about the people who inspired my career. See the answer to that question. 😉

What is one “efficiency hack” you use consistently in your life to keep your time and mind free to focus on your strengths and passions?

“The “3 B’s” of written communication: Be Brief, Brother.

All actors or musicians have sleepless nights. We have a term we use with our clients called the “2 a.m. moment.” It’s when you’re wide awake and thinking not-so-positive thoughts about your business choices and future. Can you describe a 2 a.m. moment (or moments) you’ve had and how you overcame the challenges?

“When I’ve had moments of doubt I like to look back on where I began and what I’ve accomplished — just try to put it in perspective. Usually the worries and self-doubt come from comparing myself to other successful people, which is a bad habit. We all get caught up comparing our insides to other people’s outsides and it’s a recipe for failure. Sometimes I’ll watch something I’ve done that I’m proud of or look back on a great testimonial or email I’ve received. A lot of times what quells my anxiety is just getting to work — accomplish one task.

Nobody likes to fail, and we sure don’t like to admit we failed. Can you describe a moment when you confided your most closely-held business issues/problems to someone close to you, and how the conversation(s) helped you work through the issue?

“This happens all the time for me now, and what changed was when I began looking at other funny speakers as colleagues instead of competitors. Once I began to confide in other speakers about questions or issues I’m having, they began to do the same and we have helped each other tremendously with anything like website design to sharing leads for gigs. I now view crappy work cultures as my ‘competition.’”

What’s on the drawing board for your next venture?

“I’m the keynote speaker for a HR Summit in Vienna Austria this fall and I’m currently working on that talk. If you have any thoughts about getting a room full of Austrian HR professionals to laugh, please let me know! Oh, and I guess I’m still writing that damn book.”


What did we miss? Feel free to share any other thoughts or advice on overcoming failure, initiatives you’re currently supporting, any other relevant information you would like to share with the readers.

“If you want to learn more about the benefits of humor and how to apply it in professional settings, join me at the Association for Applied and Therapeutic Humor annual conference in Chicago in April! Here’s the website: https://www.aath.org.”

What is the best way our readers can follow you on social media?

All of my social media contact info is my name: @paulosincup

Twitter: https://twitter.com/paulosincup

LinkedIn: https://www.linkedin.com/in/paulosincupspeaker/

Facebook: https://www.facebook.com

Instagram: https://www.instagram.com/paulosincup/

This was really awesome! Thank you so much for joining us!

Originally published at medium.com

    The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
    Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

    Sign up for the Thrive Global newsletter

    Will be used in accordance with our privacy policy.

    Thrive Global
    People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

    - MARCUS AURELIUS

    We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.