Dream Job Diary: Sex with Dr. Jess

Have you ever wondered what it takes to become a certified sex expert? Well we sure did! So we went out and found one to ask her how she earned that title. Meet this week’s dream diary subject, Dr. Jess O’Reilly!

Dr. Jess is a sex and relationship expert. She earned her PhD in human sexuality with a focus on education, but that’s not the only thing that makes her an expert on all things sexy. Dr. Jess is also a sought after speaker, presenting at conferences all around the world. She has also appeared on radio and television, from 102.1 the Edge in Toronto to Playboy TV in, well, everywhere!  She also hosts her own podcast, called, of course, “Sex with Dr. Jess”.

What sets Dr. Jess apart is her practical, accessible, and humorous approach to relationship and sex advice. She’s easy to listen to, she makes you laugh, and she’ll teach you things you’ve never known or even thought about. Dr. Jess has shared her wisdom with millions of people around the world through the media, both social and mainstream. She’s even traveled across the globe to help couples including royalty and presidential candidates) to transform their relationships from good to great. Now if that’s not a dream job, I don’t know what is!

Now if that’s not a dream job, I don’t know what is!

Want to learn how Dr. Jess got into the world of sex? So do we! Take a read below.


What is your official title? Do you have one?

I’m a Sexologist. My parents are thrilled:)

How did you get into your current line of work?

I was a high school teacher in Toronto and I saw the cost of an inadequate sex and relationship education system. I had teens coming to me with issues related to pregnancy, abusive relationships, broken condoms, STIs , sex work and harassment based on sexual orientation and gender identity. I wanted to be a part of the solution.

Did you go to school/get training for your dream job?

Yes and no. I went to school for both education and human sexuality, but most of my job involves speaking and business development and most of what I learned in school doesn’t apply to my day-to-day.

Interestingly, the schooling program that I considered the biggest waste of time (at the time) is the one that is now most essential to my work. I thought teacher’s college was so boring and redundant, but the principles I learned with regard to education apply in almost everything I do today — from supporting staff to designing engaging programs that will change peoples’ lives. I’m now so appreciative that I had the opportunity to study as a teacher.

Is this a job you attained or did you create it for yourself?

I definitely had to create this job on my own. There are no job postings for sexologists. I also help others in the field when I can — I want to see more qualified sex experts (especially other people of color) thriving! If you want to go into the field and I can support you in some way, let me know!

What was your first job ever?

When I was in grade nine, I worked a number of jobs:

I sold popsicles and ice cream on a Dickee Dee bicycle cart that was too heavy for me to ride up a 5 degree incline.

I taught swimming.

I worked as an executive assistant to an Executive Director who was blind — she taught me so much, as I was her “eyes” while completing executive tasks. At the age of 15, I learned to write grant proposals, balance a budget sheet, complete power of attorneys and communicate with government agencies.

I worked at a “fine foods” store up at Yonge and Lawrence. I think it paid $5.45/hour and every so often, I’d receive a 25 cent tip.

Before you got/created your dream job, what was the best job you had?

I didn’t know it or appreciate it at the time, but bartending was a great job. I learned so much about people and about myself. If I could go back, I’d show more appreciation for the job and all of the people I met. Over the years, I worked everywhere from Fluid and Budo to The Docks and Level. And I met my now husband working at Hotel nightclub on Peter Street:)

What was your most hated job?

When I was around 14 years old, I worked one shift as a clown who wore a sandwich board which read “1 Dozen Roses. $19.99”. I was supposed to walk around Yonge and Lawrence (where the older kids congregated after school) and do funny clown things. I don’t embarrass easily, but I gave up after my first shift.

If you weren’t doing this, what would you be doing?

I’d be working for myself in some capacity — probably work as a brand or business coach/strategist. I’ve never had a corporate job (I’m one of the few who can’t say “I left the corporate world…”) and probably never will.

What accomplishment/achievement are you most proud of?

In business, I’m pretty proud of the work I do with YPO (Young Presidents’ Organization) and EO (Entrepreneurs’ Organization). I get to work with some of the most powerful and ambitious people in the world to address the topics that make us most vulnerable — love, sex and relationships. It’s always a challenge and I ride a passionate high during and after every single workshop.

In the past year alone, I’ve spoken at events in Switzerland, Mexico, Czech Republic, UAE, Lebanon, Ukraine and all across the US and Canada. Later this year I’ll be in India, Sri Lanka, Nepal, China, Thailand, Philippines, Italy, Croatia and Slovakia to name a few. I love the travel and YPO & EO take me to locations, palaces and far-off retreats that I’d be unlikely to discover on my own.

In life, however, I’m definitely most proud of my relationship with my partner. I’ve been with my husband, Brandon, for 16 years and we work hard to have a happy, healthy, exciting relationship. I really can’t take much credit (he’s way more amazing than I am), but I’m still proud of everything we’ve built together.

What advice do you have for someone who wants to find their dream job but hasn’t yet?

Don’t listen to people who say things like “Just believe in yourself and dreams will come true.” That’s nonsense that people (usually with a ton of privilege) spout. I’m not saying they’re being disingenuous — they probably believe it — but it simply doesn’t apply to everyone equally, because we don’t start on an even playing field.

My best advice is to give more than you take — in business and personal relationships. Research shows that givers (as opposed to takers and matchers) prosper, so if you can offer time, energy or support to others, just do it. (Read Adam Grant’s Give and Take if you have the time.) I’ve found that being open to sharing experiences, strategies and personal insights has been key to my business development.

Follow Dr. Jess on social media below, and learn more about her work (and yourself probably while you’re at it!).


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Nadia Elkharadly

Nadia Elkharadly

Nadia Elkharadly is the Co-Founder and Managing Editor of Addicted Magazine. Her myriad of addictions include music, fashion, travel, technology, boxing and trying to make the world a better place. Nadia is also a feminist, an animal lover, and a neverending dreamer. Keep up with her on social media through @thenadiae.
Nadia Elkharadly