Comedian Comedy: Vanessa Hollingshead, New York City, NY   Book This Career Mentorship   Watch the Video

This is the real deal. A VocationVacation not for the faint of heart or conservative nature. Vanessa will not sugar-coat this profession. She will expose you to the raw truth about what it takes to be a successful comedian. Highly respected in the industry, she’s a natural in the spotlight and seems to effortlessly send a roar of laughter through a room full of strangers. Entertaining people with humor is her craft, but the dedication and resilience it took her to get there is no joking matter.

At an extremely young age she did some professional acting and recognized her gift for being funny. Turning that talent into a lucrative career, however, proved to be extremely challenging. After years of 9-5 temp positions her resume had become a small booklet. Yet, the need to pay her rent didn’t stop her from getting on the intercom and broadcasting a little impromptu side-splitting imitation of her boss and coworkers to release some energy. Needless to say, she went through some 70 temp jobs. One day, however, she finally said to herself, "I’m literally dying in these offices".

Not that acting came easy for Vanessa. She remembers dragging herself to countless auditions. Ones she couldn’t stand. Ones she even hated. And there she would congregate, with all the other hopefuls, in an awful single-file line in some stuffy hallway. Waiting. And she would naturally end up cracking jokes.

Then, fourteen years ago, an open mic night changed everything. She told her friends she was going to give it a whirl. She remembers nervously having to wait to go on as she listened to all the other stand-ups and watched the audience trail off one by one. Four hours later, when she finally got up on stage, she looked around the pathetic room and said exhaustedly, "Even Richard Pryer wouldn’t be funny at this point! What? There’s a few of you comedians out there? Who’s even listening right now?!" It wasn’t the performance that put her name in lights, but it gave her the motivation to make it happen.

Early on Vanessa realized that she had a lot of characters in her routine, but no sense of self. She soon discovered that most really good comedians really don’t have anything all that exciting going on in their lives to be used as content. The brilliance lies in taking real-life situations, however common or tragic they may be, and spinning them in a way that is hilarious to the masses. For example, Vanessa has no problem telling a room full of strangers that her father introduced some famous musicians to LSD. She’ll continue to reveal that after going on an accidental "trip" herself at the age of five, she went to live with her mother who was more concerned with her full-time career of "finding good grass in bad neighborhoods". The audience bellows, as her therapist cringes.

Struggling from gig to gig, she admits, "I was surviving on cigarettes, coffee and watermelon. I knew there was a better way." So she lived, ate, and breathed comedy for the next nine months. Her work ethic was like no other. She finally landed a spot at the well-known Comedy Strip in New York. Looking back at it, she recalls, "I told myself, if I don’t make it through this gig, I’m getting out of the business". That 12-minute show turned out to be her big break. She nailed it and got four development deals out of it including an offer to be on the Drew Carey Show. The tape from that show was her catalyst. Her turning point. She remembers proudly, "Every joke that night got applause. For the first time, everyone laughed!"

She also met her future husband that night. Vanessa was married to Lucien Hold, the Artistic Director of the Comic Strip, for eight years prior to his death in 2004 due to complications caused by Scleroderma. In many ways, he was her inspiration. He encouraged her to paint, for example. Painting is still one of her favorite methods of meditation and has helped her realize that “the show must go on!" even after Lucien’s tragic death.

Her favorite part of being a comedian is the actual performance. She describes the writing as painfully disciplined and the waiting as excruciating. "The hardest part is definitely waiting to go on. Sometimes you wait for three or four hours for your five minutes on stage. It can be demeaning to the spirit. But you can’t take it personally", she explains, "Ego is everything. You must not let it affect your self esteem."

Vanessa’s many successes include The World Comedy Tour in Australia and Comedy Central Presents in 2005. She has been featured on Tough Crowd with Colin Quinn, Dateline, Oxygen, the Montreal "Just for Laughs" tour with Kevin Pollock and she’s a regular favorite on Comedy Central. She has performed at The Montreal Comedy Festival a total of five times and toured approximately 30 military bases in the Middle East for a month! But, being a New Yorker through and through, she is most often seen a little closer to home at the Comic Strip, Stand Up New York, Caroline’s, Gotham Comedy Club, The Improv, The Laugh Factory, and the Comedy Cellar in the Big Apple.

Vanessa is living her dream. She travels the world. She performs seven nights a week. She is raw, blunt, and, yes, she laughingly admits, maybe even a bit crazy. But she will certainly make you laugh. Not the career path one would suspect of someone that describes herself as "painfully shy", but once she gets rolling there is no mistaking that she has found her calling in comedy.

***Due to Vanessa's travel/work schedule, we highly recommend you purchase travel insurance in the event Vanessa needs to reschedule. VocationVacations nor Vanessa is responsible for a change in scheduling.

Vanessa will mentor you in some or all of the following Vocationer activities:

• Writing five minutes of material from the Vocationer’s life
• Spinning a corporate/work speech or presentation into something funny
• Molding any premise into a joke by learning about the "voice", the look, the clothes, and the way one presents oneself
• Learning how to use a microphone, with or without the cord, and what to do with the microphone stand while performing
• Analyzing the Vocationer’s material at an open mic situation
• Learning how, and where, to begin and what entails being a "full time" comic including how to cross over from a day job
• Marketing yourself with pictures, resumes, bio, MySpace account, as well as setting up open mics gigs
• Working the festivals including Montreal Comedy Festival, Aspen Comedy Festival, etc.

The Comedian VocationVacations holiday includes:

• Two days of one-on-one mentorship in your dream job as a Comedian
• The opportunity to participate in a total of one hour of pre- and post-VocationVacation career coaching from an accredited, affiliated VocationVacations career coach
• A pocket-size VocationVacations journal so you can document your dream job becoming a reality
• Light lunches with your mentor

Available: All year based on mentor's availability. Can only be booked 4-8 weeks in advance of a requested date.

Price: $1149 Per Person

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Suggested Accommodations

Hilton Times Square	Doubletree Metropolitan Hotel - Midtown
(Not included in the price of your VocationVacations adventure) Other activities and tourist destinations while on your VocationVacations® dream job holiday: NYC & Company - New York City's Official Tourism Website for Tourists, Journalists, Travel Professionals, and Meeting Planners I Love New York - The Official New York State Tourism Website NY.com - The Paperless Guide to New York City Reservation, Cancellation and Rescheduling Rules and Conditions: Full payment of the VocationVacations dream job holiday is required to make a reservation. A $100 non-refundable fee is assessed if a VocationVacations experience is cancelled or rescheduled prior to 14-days of the scheduled VocationVacations holiday, based on the approved availability of the mentor to reschedule. A VocationVacations adventure cannot be rescheduled and is non-refundable if cancelled within 14 days of the scheduled VocationVacations holiday. Written notification of cancellation or rescheduling is required in all cases. In the US, Grounded Nomads, LLC and VocationVacations holidays encourage all customers to acquire travel insurance to cover any unforeseen expenses due to cancellation or rescheduling. In the UK, Grounded Nomads, Ltd and VocationVacations holidays must require all customers to acquire travel insurance to cover any unforeseen expenses due to cancellation or rescheduling and provide verification of such travel insurance to Grounded Nomads, Ltd.