Dreamers: “They told me It was impossible and I did it anyway” With Jill Stanton of Screw The Nine To Five

Candice Georgiadis
Mar 18 · 13 min read

So often people focus on what they think they have to DO in order to get what they want, but that’s backwards. Instead, you need to determine who you need to BE — the beliefs you need to live by, the habits you need to have, the characteristics you need to embody and the identity you need to maintain to achieve what you want to achieve. For example, if you want to be an entrepreneur and start a business you have to be driven by a desire to serve people, you need to be consistent, comfortable with the uncomfortable, a risk taker, self-motivated, unfazed by other people’s opinions and self aware…to name a few.

However, what most people do is think they need to operate from a place of pure push and grit in order to create what they want. Yet most of the time that simply ends in frustration and burnout because grit and hustle will only take you so far. It’s the ways of BE’ing that will carry you through moments of failure, stress and uncertainty and help you create everything you say you want.


a part of our series about “dreamers who ignored the naysayers and did what others said was impossible”, I had the pleasure of interviewing Jill Stanton.

Jill Stanton is the co-founder of Screw The Nine To Five where she helps unsatisfied employees quit their jobs and start online businesses. Coined by Forbes as “a destination for up-and-coming online entrepreneurs,” Screw The Nine To Five has inspired tens of thousands of new entrepreneurs to quit their jobs, build thriving businesses, and live lives of meaning and purpose.


Thank you so much for joining us! Our readers would love to ‘get to know you’ a bit better. Can you tell us your ‘backstory’?

ur story begins back in 2009 in Toronto, Canada where we met on a blind date. The rest is history, and we’ve been traveling the world (having lived in 14 countries together so far), running our businesses and raising our little guy from anywhere with a Wi-Fi connection.

Speaking of businesses…

We started our first business together in 2012 on a whim when Josh pitched me the idea of starting a skincare affiliate site together as a way of replacing the income we were each making from our individual businesses at that time. We soon had over 30 websites in different niches from skin care to weight loss to supplements to personal hygiene to high heels.

In December 2012 we were in Costa Rica for our wedding. We were sitting on our balcony, having a quiet moment before welcoming our guests and we started talking about starting ANOTHER website. This time though our site would share our story and everything we had learned building these sites while traveling the world, and Screw the Nine to Five was born.

The only problem was, we had never built a personal brand before or put our names and faces “out there” in any kind of “expert” capacity. Our first online course launch sold precisely ZERO and while that nearly took us out of the game (because we felt SO defeated), it was one of the best lessons we learned because it taught us the importance of teaching what you know. We pivoted our business to start teaching affiliate marketing, had our first successful launch (a whopping $8,400!) and then our second ($38,000), started a podcast, a free FB group (which grew to over 45,000 members) and then kicked the doors open to a monthly membership community we affectionately called, Screw U.

And to think it all started on a blind date.

Are you working on any new or exciting projects now? How do you think that will help people?

We sure are, and the inspiration for it came after taking a bold leap in our business and shutting down every piece of it that no longer lined up with our core values.

Because of that we were able to have the mental white space to dream up our next moves in our business and how it will serve our audience.

It’s called Shift To Six and it will be a 3 month program and live event experience designed to help online course creators, coaches and membership site owners cross the $100,000/year threshold in their business.

The reason we believe in it so hard is because after working with thousands of up-and-coming entrepreneurs over the last 7 years we’ve realized that when they cross the six-figure mark, something shifts in them.

It’s almost like their eyes are opened up to even more possibilities, they build an exciting amount of confidence and they start dreaming bigger dreams.

So, our big 10 year vision is to help 100,000 entrepreneurs cross the $100,000/year mark — which is a ripple effect of $10 billion generated!

And honestly, we find that goal insanely exciting (and kinda scary) to chase…so we’re going for it!

In your opinion, what do you think makes your company or organization stand out from the crowd?

I believe what makes Screw The Nine To Five stand out is our commitment to transparency and honesty, even when it feels scary.

There are SO many brands in our space that paint this unrealistic rosey picture of what entrepreneurship looks like (hot chicks + fast cars, anyone?) and it couldn’t be further from the truth.

We’re committed to pulling back the veil and showing the real side of entrepreneurship — the challenging parts, the fulfilling parts, the exciting parts, the stresses, the successes and how it helps you become the best version of yourself.

Ok, thank you for that. I’d like to jump to the main focus of this interview. Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us? What was your idea? What was the reaction of the naysayers? And how did you overcome that?

Hands down it has to be the moment we decided to shut down every single piece of our business that was no longer serving us.

We had a membership program called Screw U that helped put Screw The Nine To Five on the map, made us more money than we had ever made at that point ($332,000/year) and gave us the opportunity to serve thousands of die-hard members. For 3 years we served that community day in and day out. We would host coaching calls, create courses, host an annual members-only live event and even created a virtual co-working space where members could hang out online and co-work together.

And then our son was born in February 2018 and all of a sudden things started feeling “off”. We no longer felt aligned with the business we had built or the work we were doing; which caused us a ton of stress because we couldn’t figure out WHY we were feeling this way.

Fast-forward to July 2018 and we finally had a breakthrough moment of clarity and realized (or gave ourselves the permission to admit) we no longer wanted to run Screw The Nine To Five the way it was built. We didn’t want our membership site anymore….or our courses, our coaching services or even our free Facebook Group! I wish I could properly convey how stressful (yet, oddly liberating) this realization was for us at this time.

So we did the only thing we could think of: We told everyone inside our membership, our courses and our free community that as of December 31, 2018 we would be shutting down every single piece of our business that no longer aligned with our values, who we wanted to be and what we wanted to create inside Screw The Nine To Five.

What’s even crazier about this story is we actually told our members in person at our members-only live event. The reason we did that is because it felt like the best way to stay in integrity with them, be honest with them and give them the respect they deserved. After all, a big portion of our members had been in the community since Day 1! So we didn’t want to hide anything or take the easy route and tell them online where we could hide behind our computers and not tell them to their face.

Their reaction though was unlike anything we expected — and a true example of how amazing these humans were! 98 percent of them were overwhelmingly encouraging and understanding; some even crying or coming up to give us hugs.

One member even told us that this felt like a moment where “the kids are moving out of the house”, a touching metaphor since our members called themselves “Scramily” (a.k.a. Screw Family).

In the end, how were all the naysayers proven wrong?

Sure, there were some people who didn’t like the decision (and 3 people who kicked up a little bit of a fuss), but out of over 650+ members, I think that is a pretty amazing ratio and we will forever be grateful for the time we got to spend with them.

In fact, a lot of them are still in our worlds and found ways to work with us in 2019 through different promotions we were running, live events we were hosting and quite a few have mentioned that they will be the first ones to join Shift To Six.

It’s now just slightly more than one year after making that decision and our business is more successful than it’s ever been (we even surpassed 2018’s revenue in the first 8 months of 2019), we’re happier than we’ve ever been and our vision for our mission is clearer than it’s ever been.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I know this is going to sound so cheesy and cliche, but it’s my husband, Josh. He’s been on this entrepreneurial journey with me for the last 8 years. He’s been in the ring with me, going the rounds with me, wading through the uncertainty with me, navigating the ups and downs with me, celebrating the wins with me, pouring me a tall glass of wine when things feel challenging, and building this movement with me. He’s taught me so much about managing and leading a team, creating the right business systems and structure, and the importance of always reinvesting in yourself as an entrepreneur.

He’s been my greatest teacher and mentor, and is one of the smartest and most talented entrepreneurs I know.

It must not have been easy to ignore all the naysayers. Did you have any experiences growing up that have contributed to building your resiliency? Can you share the story with us?

I’m going to take us back to my high school years to a time when I was talking to the school’s Guidance Counselor. She had brought me in to talk about my post-secondary plans and I mentioned that I had my eye on a few schools that had Radio and Television Broadcast programs.

I had told her that for years I dreamt of doing something that made an impact on people. Something that would light up their screens and bring joy into their lives AND wouldn’t have me clocking hours upon hours at a drab corporate job I hated.

She looked me dead in the face, with a faint look of disbelief and just said “Jill, sweetie, I think it’s time to start considering a more realistic path. What about a communications degree? Those kind of degrees are what lead to real careers.”.

Fortunately, I was a stubborn (and slightly sassy) teenager who always knew deep down that a “real career” wasn’t the path for me. So I nodded my way through that 20 minute “career counselling” session, thanked her for her guidance, took the stack of brochures she handed me, walked out, turned down another hallway and threw them all out.

That was a pivotal (and memorable) moment for me because it made me realize that I would never choose a conventional path for my life. And while my small screen ambitions took me down many paths (landing me various commercials, small TV gigs, a stint on Deal Or No Deal, 2 web TV shows and now into the very, VERY early planning phases of a docuseries), the real lesson I took away from that day (which took me years to realize) is we need to be aware of who we are taking advice from.

Based on your experience, can you share 5 strategies that people can use to harness the sense of tenacity and do what naysayers think is impossible? (Please share a story or an example for each)

  1. Get clear on what you want.

It sounds crazy, but most of us are REALLY good at knowing what we DON’T want, yet we rarely give ourselves the permission to dream big and admit what we DO want. From my experience that’s typically because we’re nervous about what people will think or say if we dream big and have the guts to go after them!

It’s also because most of us tend to measure what we could LOSE by “going for it” (because that’s easy to measure and is typically related to past experiences) instead of imagining everything we could gain by going after what we really want, because it’s hard to even fathom or predict how awesome things could be if we put ourselves out there. And that behavior is typically what keeps people stuck and rooted in the “what if’s”.

However, if we can release the “what if’s” and step into the uncertainty of going after what we want, no matter what, then we have the potential to create a life that is beyond our wildest dreams and expectations. But it all starts with giving yourself the permission to get clear on what YOU really want.

2 . Decide who you need to be to achieve the impossible

So often people focus on what they think they have to DO in order to get what they want, but that’s backwards. Instead, you need to determine who you need to BE — the beliefs you need to live by, the habits you need to have, the characteristics you need to embody and the identity you need to maintain to achieve what you want to achieve. For example, if you want to be an entrepreneur and start a business you have to be driven by a desire to serve people, you need to be consistent, comfortable with the uncomfortable, a risk taker, self-motivated, unfazed by other people’s opinions and self aware…to name a few.

However, what most people do is think they need to operate from a place of pure push and grit in order to create what they want. Yet most of the time that simply ends in frustration and burnout because grit and hustle will only take you so far. It’s the ways of BE’ing that will carry you through moments of failure, stress and uncertainty and help you create everything you say you want.

3 . Invest in yourself

I know this seems cliche, but if you want to do the impossible you are going to need to invest in yourself, your skills, and the mentor(s) who can guide you along the path. This is what separates those who achieve the impossible from those who say they WANT to, but never do.

If you want something you’ve never had, you typically have to do things you’ve never done and most of the time that comes with some form of investment — whether that is time, money or energy.

4 . Build your business from a place of alignment and ease (and create something that serves YOU as the founder)

If someone is not in the ring with you, taking the punches with you, fighting for a dream with you, creating the uncreated with you and wading through the uncertainty with you, they don’t get to tell you what you are (or are not) capable of; what you can or cannot achieve.

That is for YOU to determine and as long as you have a clear vision for what you want your life to look and feel like, and you are detached from how (or when) you get there, then you can create magic in your life and achieve the impossible.

5 . Surround yourself with people who match your future (not your past) and are where you want to be

Surround yourself with people who live and breathe the way that you want to be. The reason this is so key is because people who have achieved greatness or success in their life have typically done that by overcoming obstacles and viewing challenges as mere stumbling blocks that help them become better versions of themselves.

What is your favorite quote or personal philosophy that relates to the concept of resilience?

If it doesn’t challenge you, it doesn’t change you.

The reason I love this quote so much is because all of my biggest wins, successes and personal achievements have all come about because I waded through times of crushing uncertainty and fear.

And it’s that willingness to embrace uncertainty (when most people shy, hell, RUN away from it) that makes life so rich, shows you what you’re made of and transforms you into the best version of yourself.

It’s also what separates those who create their reality and achieve their dreams from those who simply let life happen to them.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I love this question because I believe we ARE building a movement. Our mission with Screw The Nine To Five is to help unsatisfied employees quit their jobs, build online business and get them past the $100,000/year threshold so they never look back.

We do this because we know there are millions of people who feel trapped (and absolutely miserable) in their jobs and if we can give the ones who want to change their lives the tools to do so, they can create something that gives them the financial freedom, time freedom, location freedom and personal freedom they crave.

And while entrepreneurship definitely has its challenging moments, it also transforms you into the best version of yourself as you learn more about yourself, the way you think, the value you’re offering, the impact you’re creating, the lives you’re affecting and the wealth you’re building. All of these lessons, skills and traits stack upon each other to create a life that is dripping with meaning and purpose. THAT is the movement we are building!

Can our readers follow you on social media?

Here are our top 3 platforms we hang out on most:

  • On IG: Instagram.com/screwtheninetofive
  • On FB: facebook.com/saynotoninetofive
  • Podcast: thescrewshow.com

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Candice Georgiadis

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Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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