6 Fearless Millennial Women You Need to Know Now

To celebrate International Women’s Day and Women’s History Month, I wanted to do something special this year. I know so many amazing millennial women who are doing some incredible things in terms of their careers, and I thought this would be the perfect opportunity to highlight some of these rockin’ women and give them the credit they truly deserve.

I asked each of these women three questions about the challenges they’ve faced so far, how they’ve been able to overcome these challenges and what advice they would give to other women so we can all live more successful, happy and balanced lives.

I really hope you enjoy this post, but I am warning you it’s a big one (over 4,000 words)! To make things easier, below is a legend that will take you to each woman’s interview. And make sure to join my Money. Life. Balance. Facebook group to chat about today’s post and to nominate a woman you think we can all learn from!

  1. Gina Kennedy, Radio Host, Voice Actor & Rockstar
  2. Kelly Davio, Nurse & World Traveller
  3. Dr. Dee, Doctor & Entrepreneur
  4. Tess Wicks, Content Marketer & Podcaster
  5. Rebecca Basi, Director of Marketing
  6. Taylor Stinson, Food Blogger & Journalist

1.) Gina Kennedy, Radio Host, Voice Actor & Rockstar

gina-kennedy-radio-hostGina Kennedy was one of the first people I met when my husband and I moved to Toronto and now she’s a dear friend of ours. Originally from Nova Scotia, she moved to Toronto to pursue her dream as a radio host. Her hard work and determination paid off because now she’s the host of Sirius XM’s Press Play with Gina K, she’s a voice actor on the side and to top it all off she’s the bassist in the Toronto band Altered by Mom. You go girl!

I’ll also be interviewing Gina for this Wednesday’s Mo’ Money Podcast episode, so make sure to check that out too!

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

In terms of my career, one of the biggest challenges is — not so much based on my age, but being a woman — the music industry is still very male dominated. It’s hard to be taken seriously when you have different ways of thinking than the majority of the people in the room and have to fight on behalf of  a voice that’s so often shut down (or non-existent).

2. How did you overcome, or are working to overcome that challenge?

I still work on this everyday. But some ways that I am actively trying to overcome these obstacles and stigmas are:

  • To make myself well connected in my industry, as relationships are everything.
  • Be well-educated on the artist or topic I’m focused on.
  • Go after the many things I’m interested in outside of work.

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

The advice I would give someone in my position is don’t be scared about moving on and trying new things. You are not defined by what others think of you, and you have many talents left to explore. If you never try anything else, you’ll never learn what you are capable of!

One last bit of advice, be nice to yourself. It all takes time, and you are doing great.

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2.) Kelly Davio, Nurse & World Traveller

kelly-davio-nurse-travellerI’ve known Kelly Davio for as long as I’ve been with my husband (over 9 years!). She was my husband’s best friend growing up and was even in our wedding party (she served as official groomslady).

Throughout the time I’ve known her, she has been one of those people I’ve always been in awe of. She completely embodies the word “fearless” in so many ways, and has done so many things in her life already, it’s sometimes hard to keep up (like hiking up Mount Everest for example).

Not only is she an incredible world traveller, she’s also super career-oriented and incredibly money-savvy. For her wedding, to save money she did a potluck, wore a friend’s wedding dress and served up homemade wine (and it was one hell of a fun wedding!). Not only that, she just did a stint working as a nurse in Nunavut and she is also the co-founder of the Second Home Child Outreach Program.

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

I faced the typical problems that most young people face when I started out: lack of money, not knowing what I wanted to do with my life, etc. These were easily overcome with hard work and forcing myself to make decisions. I didn’t know what I wanted to do, but I knew that I wanted job security and upward mobility, flexible hours, and I wanted to learn to be good at whatever I was doing.

I put my name on many waiting lists for programs that I knew led to good long-term job prospects (like welding) and psychiatric nursing happened to be the one that accepted me first. I was very lucky because I fell in love with the work.

I think the biggest challenge that I have faced has been finding balance in my life. There is immense pressure on young women today to “do it all” and by that I mean have a great career and be independent but also settle down, get married and have a family before the age of 35. As a child I was the recipient of the very strong message that a modern woman should put her career above all else and that a family and relationships will just happen along the way. Now that I’m in my 30’s I see the damage that ideology inflicts on people who are very “type A” like myself.

I worked 2 jobs to put myself through college and continued to advance my career full steam ahead in my 20s, getting a second registration and going to work in medical emergency and acute psychiatry. I don’t regret it, but I wish I had known that there would come a day when I would have to throttle back on the careerism. I never entertained the idea of having kids, or thinking about what sort of lifestyle I would want when I decided to start a family.

Now that my husband and I are thinking of doing that, I feel this terrible sense of failure if I ease back on my work schedule. The reality is, I let my career define me in ways that aren’t actually conducive to my wellbeing. Just because I can physically work 23 twelve-hour shifts per month, doesn’t mean that I should (full-time is 14 shifts per month).

I am now struggling with the realization that I have let my career carry me to a place that doesn’t have room for other things, and those things are important to me and I have to make room for them somehow. I know lots of other women who are struggling with the same thing, this deep-rooted guilt that if they stay at home with their kids (or take time off during pregnancy) that they are failing or being lazy. Those same women feel guilty if they go to work, as they aren’t taking care of themselves and they feel that they are letting down their children.

It’s quite the conundrum of the modern world, and there are no easy answers. I’m finding that I wasn’t prepared to face such a dilemma and it completely blindsided me the moment I turned 30.

2. How did you overcome, or are working to overcome that challenge?

I used to solve the problem of my workaholism by working like mad for 6 months or so and then taking long trips to volunteer in the 3rd world. This meant I couldn’t pick up extra shifts at the hospital, and it would force me to enjoy new experiences.

Now that I am settling down more, I realize that it’s much harder to stop and smell the roses with the phone always ringing off the hook, asking me to come back to work. I now know that I need to strategize with myself to actively stop myself from saying “yes” to every phone call.

I have been spending a lot of time exploring what it is that I want out of life. I am asking myself the hard questions that I never remotely considered when I was younger. Questions like:

  • “What else am I good at?”
  • “What else is worth my time and energy?”
  • “What does it mean to have a balanced life?”
  • “If I spend less time working, what will I replace it with?”
  • “How involved do I want to be with my family?”
  • “What sacrifices am I willing to make?”
  • “What are the hidden costs to my decisions?”

I have come to realize that there are lots of hidden costs to careerism that I hadn’t previously taken into account. I do want to have kids, and I don’t want to suck all of the enjoyment out of that process by working myself into the ground.

I find that my ego can pull me quite forcefully away from anything that doesn’t immediately benefit my career. That’s why it’s important to start cultivating balance and an appreciation for my other attributes. I have been spending lots of time reflecting on the life that I want for myself and what I need to do to live it. I have never had a problem with motivation, the troubles in my life have resulted in being too motivated in one particular direction.

Now I am finding it helpful to set concrete goals for other areas of my life. These can be things as simple as “read a book this month” or “spend time with at least 2 different friends.”

Contrary to what I was told, life doesn’t just “fall into place” if you’re a good worker and saver. You actually have to invest time and energy into things if you want to be successful in life (not just your career). I am learning that working 12 hour shifts every single day or night doesn’t mean success if I am too tired for anything else in my life.

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

I am a very organized, driven, headstrong, “type A” personality. I can definitely speak to what I wish I had heard (maybe I did hear it at some point, but I wish I had listened to it): Time is money, but money is also time, and one of those is not renewable.

You can always make more money, but you will never be this young again. Don’t spend your whole life waiting for the future, enjoy the present moment too. Success can be quite illusory, strive for equilibrium. You can be very financially successful but out of balance with yourself — that’s why people can be rich but unhappy.

Set concrete, well-rounded goals and define what makes you happy. Not how much money you need for some abstract form of happiness or comfort, but real happiness. Be it days at home with your partner, gardening or watching a sunset in the Arizona desert. Money can buy you time, but time isn’t just a sacrifice on the altar of capitalism. Use it to enrich your life as a means to an end, not an end in and of itself.

The carrot will always be one step in front of you, and there is no finish line with warm embraces and confetti raining from the sky. It’s true that life isn’t a destination — it’s a journey and that journey changes directions over time, and that’s okay.

Save wisely and spend wisely. If you want more time, don’t waste your money and vice versa. So much spending is done on autopilot and I’m guilty of that as well. I have to constantly check in with myself and ask “Is this what I really want? What are the hidden costs? Am I comfortable with the price tag?”

If I go out and drop a bunch of cash on a nice meal rather than cooking at home, I know I will have to spend more time working later to make that money back, so is it worth it to give up x amount of time with my loved ones in order to do/buy this thing? If yes, I do it. If I’d rather be spending a day off at the park, then no. It’s basic cost benefit analysis. That doesn’t mean being entitled, it’s about being aware and grateful and not living beyond your means.

Practice gratitude and enjoy hard work, but don’t derive pleasure from working yourself into a state of dishealth and disharmony from the easygoing joy of life. If you are so exhausted on your days off that all you do is sleep on the couch — that’s not living. Saving money means nothing if you’re wasting time.

Strive for a life where you spend time away from work doing things that make you feel fulfilled. Practice gratitude every day, be mindful and present in your relationships and daily life to stay attuned to what it is that makes your life worth living.

For me, it’s working to improve the lives of children in Nepal. We started an abandonment prevention program to feed the children of poor families so they don’t have to give their children to orphanages.

Stay grounded and humble. When you feel like you don’t have enough, or you aren’t providing enough, look at the big picture and count your blessings. There are lots of people in the world who work 12 hours per day and can barely keep their families alive. This is a good reminder that you’re doing okay, and you don’t need to buy a brand new piece of furniture to match the carpet to be happy.

And to cap things off…

No one is to be found who is willing to distribute his money, yet among how many does each one of us distribute his life!… You squander time as if you drew from a full and abundant supply, though all the while that day which you bestow on some person or thing is perhaps your last. – Seneca

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3.) Dr. Dee, Doctor & Entrepreneur

Dr. Dee is seriously one bad-ass chick. I’m keeping her anonymous on this list because she wants to remain so, but I’m still so happy I get to share her story and the advice she has for other millennial women.

Not only is she a medical resident in Canada, she is also an admissions coach. When she’s not working long days at the hospital, she’s either working out (oh yeah, she’s a fitness guru too!), or side hustling like you wouldn’t believe.

To know someone as hard-working and passionate about her many jobs as she is, she is truly an inspiration and I’m so glad to give her the major props she deserves on my list of rockin’ women.

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

Learning when to say “yes” or “no”. By that I mean in the beginning I had to keep saying “Yes, I can do this,” and put aside all the negative self-doubt about starting successful side hustles and my career.

Once the momentum started, it was challenging to say “no” because there was this nagging belief that I had to accept every opportunity lest it be the last. Both are on different sides of the same coin of career insecurity!

2. How did you overcome, or are working to overcome that challenge?

Time has demonstrated that the business will keep coming, and the results I’m getting with clients show that I’m doing good work.

The next step is finding that equilibrium by setting more boundaries for work and personal time, and doing more efficient work in shorter periods of time. I do this by setting a clear agenda for myself every time I sit down to do my hustle, and creating templates for most of my work actions to stay organized and efficient.

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

Instead of classifying life as successes versus failures, think of your actions as experiments, and the consequences as data. You will see that your “failures” are rich with data you can mine to improve experiments for the next time. This way nothing is ever absolute, not even if you have already reached your current idea of “success”.

Also, when you want to procrastinate on something new, is it the tension between wanting to stay in your current comfort zone and wanting to step into the unknown? It’s like shifting the needle when finding a new equilibrium — it’s bound to be uncomfortable. Use that feeling as a barometer that the needle is shifting, and lean in to your next step.

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4.) Tess Wicks, Content Marketer & Podcaster


I met Tess Wicks a few months ago when she asked me to be a guest on her podcast, The Words + Money Podcast (episode coming soon!). We got along so well and just had so much in common, I knew I needed to add her to this list of impressive and inspirational millennial women.

After working for corporate America as an actuary for several years, Tess left her job to put all her energy into educating young women on how to improve their personal wealth and take control of their financial lives. 

Besides having a personal finance podcast and blog, she also works as a content marketer and money coach on the side.

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

Being a young professional woman, I have struggled with listening to my intuition and believing in my abilities to showcase my knowledge. Because I am young, and because I have a more feminine approach (and because I look very young) my biggest insecurities are in my ability to be taken seriously, and that is something we all want when it comes to our career.

2. How did you overcome, or are working to overcome that challenge?

I constantly remind myself to be BOLD in personality and BIG in presence. Always go with my gut too. Even when I feel like it might be the wrong answer or considered a “dumb question,” I make it a game or a challenge with myself to make suggestions no matter how ridiculous they may sound.

And the other thing, I used to laugh it off when people made jokes about how young I look in professional settings, but really it felt hurtful and belittling. So I started standing up for myself and telling them how non-contextual and unnecessary the jokes are.

If you don’t like being called something, but you only laugh when people say something about it, that’s saying it’s okay for people to keep referring to you and thinking of you in that way. If it’s not, put on your big girl pants and set them straight! 

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

You have complete control over the choices you make every day, and if you are consciously aware of these choices, it will lead into how you choose to live your life. Make some sacrifices now so you can live the life no one else will be able to live later.

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5.) Rebecca Basi, Director of Marketing

rebecca-basi-plastic-mobileI met Rebecca Basi almost a year ago and I knew after the first few minutes of meeting her that she was gonna go far. At that time she was working for an agency, but a few months later I saw her featured in Marketing Magazine’s 2015 Top 30 Under 30 and she’d taken on the role of Director of Marketing at Plastic Mobile where she manages marketing, communication and business development initiatives for both the firm and its clients across North America.

Rebecca is a prime example of when it comes to achieving big goals and taking your career to the next level — age has nothing to do with it.

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

There’s been times throughout my career where I’ve looked around the room and quickly realized that I’d be the youngest (by sometimes a decade!), or the only woman. And while I don’t think others noticed, it did sometimes bring feelings of self-doubt and a lack of confidence.

2. How did you overcome, or are working to overcome that challenge?

Building confidence is difficult, but you can’t get far without it. I’ve learned to realize that I am where I am today because I do good work. Others see the value in my contribution and allow me to continue to grow with amazing opportunities — and if they believe I can do it, I certainly should too. At the very least, prove them right.

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

Experience = confidence. Never give up, because everything you do — big or small — brings you one step closer to success. You can have anything you want in this world — you just need to go out, truly believe you can do it and go for it. It sounds cliché, but I swear it’s true.

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6.) Taylor Stinson, Food Blogger & Journalist


I first met Taylor Stinson a month ago over Skype. She actually lives really close to me (we’re both girls on Bloor), and she reached out to me for a piece she was working on for her Master’s of Journalism. We got along so well that our 20 minute interview turned into an hour-long chat about blogging, life and careers.

Just like me, Taylor is a hustler. Not only is she about to complete her Master’s degree, she is also a food photographer, chef and blogger of The Girl on Bloor. You know when you hear about bloggers who get invited to restaurants to eat for free? Taylor figured out how to make her hobby blog into a full on money-making business, and it even landed her a gig writing for the Huffington Post.

1. What was one of the biggest challenges you’ve faced as a millennial woman in your career?

I think that sometimes because I’m a young woman, people in my industry don’t take me seriously. I know personally from applying to a variety of jobs in media that I’m expected to work for little to no pay or for exposure, and I think a lot of other millennial women are faced with this problem quite often.

Most of the people in my Masters of Journalism program are also women, and the fact of the matter is that we’re in a field where there is a growing amount of credentialism. You have to do your time, work extremely long days and become over-educated for a number of years before you can be taken seriously, and even then you have to prove yourself capable over and over, and so many jobs are ridiculously competitive.

2. How did you overcome, or are working to overcome that challenge?

I like to think that like many other young women around my age, I’ve worked hard and have been persistent in trying to craft a career.

My blog has honestly been my guiding light in terms of keeping me going and overcoming the challenges of the media industry. It has helped me to make many valuable connections and it’s given me some great opportunities. I like to think of it as a portfolio piece that has enabled me to take on more professional work when I wouldn’t have had that chance by working in an office or going to school alone.

I’ve overcome the challenge of having to prove myself to every employer, because I’ve become my own boss in a way — when you work for yourself, you are responsible for your own success.

If you were to tell me 3 years ago that I would start a career in food photography and recipe development, I would have thought of it as just a dream. I don’t make a lot of money right now, but it’s become a source of pride in my life where I was once insecure about my abilities, and it’s also a fun challenge that I’ve loved working on and I see real results over time as I persist and improve. 

3. What advice would you give to someone like you to motivate them to never give up and strive for success?

Look at what your hobbies are, and see if there are any ways for you to turn them into something more. It could be an online business or blog, or a group that you organize where you can network with others that enjoy the same thing.

As millennials, I find it’s more important that the kind of work we do is rewarding rather than high-paying, so find something that you love and make it an integral part of your day-to-day life. Find your passion and what drives you to get up in the morning. Odds are, you have at least one hobby in your life that you love and wish you could do more often. Life has a funny way of working out when you find your passion and aggressively stick with it.

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Is there a rockin’ woman in your life? Join the conversation in the comments or in my Facebook group.

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