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“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Rebecca Gill, Co-Founder of her-people

I don’t believe every hobby, side hustle, past time needs to become a full-time career. Today, there’s a lot of pressure out there to do just that — but shouldn’t everyone put time and energy into things that they simply love doing — without the adding financial pressure for it to pay for your life? As a part of our […]


I don’t believe every hobby, side hustle, past time needs to become a full-time career. Today, there’s a lot of pressure out there to do just that — but shouldn’t everyone put time and energy into things that they simply love doing — without the adding financial pressure for it to pay for your life?


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Rebecca Gill. Rebecca is the Co-Founder of Her-People, an organization that aims to allow every woman in the world to connect meaningfully and explore freely. Today, her-people does this through four-week experiences, where 15 women meet once a week to participate in creative and personal growth workshops, wrapping it up with the Her-Pages book club. Spending the last decade in the fast-paced world of tech, her-people was a passion project born from a desire to disconnect. Disconnect from work to workshops. From clicks to steps. Reviews to real-people. When the first experience sold out in 10 days, it became clear that more women were feeling this way and the passion project became a full-time career six months later. In 2015, Rebecca was named a Top 30 under 30 Marketer by Marketing Magazine and is currently completing the Innovation & Entrepreneurship post graduate program at Harvard Extension School.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

Born in Edmonton, Alberta, I’ve moved 14 times across five cities and attended seven different schools. In hindsight, I’m sure this contributed to my call to look for ways to help women find spaces where they could connect with other like-minded women.

Today, I am grateful to call Toronto home, where I’ve lived for the past five years.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

We started her-people because we were looking for it. Time, space and commitment to regularly connect with like-minded women, while exploring different creative and personal growth workshops. It quickly transitioned from a passion project to a business when we realized we weren’t alone.

We launched after only a few conversations — and then experienced a number of big milestones very early on. First sale on day four, selling out on by day 10. People from around the world reaching out to bring her-people to their cities. Thousands of followers, hundreds of attendees, grants received and partnerships confirmed — there was an ah ha moment at least once a day.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

One struggle I find people have when translating an idea into an actual business is a simple one: just starting. Many of us spend so much time planning and perfecting that we spend years on the idea, or even worse, it falls to the back burner and never launch at all.

Having been guilty of this in the past, we overcame this by moving fast, testing often and allowing room for error.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

I don’t believe every hobby, side hustle, past time needs to become a full-time career. Today, there’s a lot of pressure out there to do just that — but shouldn’t everyone put time and energy into things that they simply love doing — without the adding financial pressure for it to pay for your life?

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

During challenging days, I circle back to the mission. For us, that’s allowing every women to connecting meaningfully. I think of all the times we’ve been able to do that — friendships formed, stories shared — which provides the perspective needed to see that while not all of it will be fresh and enjoyable, it will certainly be worth it.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Everyday, I’m learning so much. Like many entrepreneurs, I arrive at work each day with a never-ending to-do list — many tasks having to figure out from scratch. I don’t have a SEO specialist or accounting department. I have to switch between product owner to customer service to IT within a matter of minutes.

Many times, I’ve felt frustrated when things are taking longer than I’d like to figure out. For example, when we launched in New York City, we were having technical issues with our website that would not allow us to charge in USD. I would try for a bit, and then move on to the next task when I couldn’t figure it out.

One day, having had enough of not being able to get it done, I told myself that I would not leave my desk until it was resolved. Three customer support calls and five hours later, it was resolved and we were able to launch a few days later.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I knew it would be challenging and I knew I’d be working a lot. But I also I believed that I would have more freedom and flexibility. Working in the past-faced world of technology for the past eight years, I’ve worked 21-hour days, slept in the office, spent Caribbean vacations inside my room working. So come the moment I’m working for myself, I’m going to wake up when I’m done sleeping, spend my days coffee shop hopping and finally, cross somethings off my bucket list — right? Nope. Turns out, it’s harder to shake the 9–5 p.m. routine at a desk that I’d thought.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

More times then I’d like to admit. I even went as far as to go to a job interview at a startup where the CEO told me not to dare give up, and he’d be checking my LinkedIn to make sure I didn’t. Talking to people who believe in me, the mission and our work helps overcome those moments.

Can you share the most interesting story that happened to you since you began leading your company?

We’ve had a number of women reach out asking what they can do to support, to help us grow and scale, for the sole purpose of helping us connect more women. A CNN reporter, New York Times best selling author, United Nations Diplomat, CEO of a multi-billion company — we are incredibly appreciative that our mission so deeply resonates with so many women.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

We blew the power at our venue during a candle-making class. Turns out, meeting rooms at co-working locations aren’t set up to accommodate industrial stoves to melt wax…

Who has inspired or continues to inspire you to be a great leader? Why?

Every single person who has ever signed up to attend a her-people experience.

How have you used your success to make the world a better place?

While it comes to no surprise that women want to connect, create and learn, it is surprising that there are so few ways to do it well. I hope that her-people fills that gap, and that in turn makes the world a better place.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Think of ideas that solves a genuine need and you’ll never have to “sell” anything.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s not supposed to be easy, otherwise everyone would be doing it.”— Maggie Adhami-Boynton

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Whitney Wolf, Founder, Bumble!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


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