Stuck Between a Rock and a Hard Place: My Unexpected Career Journey

For as long as I can remember, I’ve wanted to be a “boss lady”.

career journeyMe at (age 3?) attending a Montessori School

It’s funny because when I look at this picture, I think it serves as a pretty good indication of the woman I’ve come to be (and yes, let’s be honest, I’d definitely wear this exact outfit today). I’m grateful to have two parents that have always served as my role models. They have both successfully made their way up the corporate ladder and I told myself that this is what I wanted too. I would work hard in school, get a good job (where I could carry around a fancy briefcase) and rise up the ranks in a corporate role to follow in the footsteps of my parents.

Or so I thought.

The thing is, I probably could have achieved all that if, you know, this was 20 years ago. What I didn’t anticipate when I made these goals as a child is how much the Canadian workforce would change and the impact this would have on me and the future of my career.

45% of Canadians are predicted to be self-employed by 2020.


But, let’s back up a bit.

Even though I had my big, lofty “boss lady” goals, I didn’t know what I wanted to do for a long time. In high school, I worked hard, got good grades and for all intents and purposes, I was a “good student”. When it came time to select university programs, I remember feeling stuck and really frustrated. I have these good grades but what do I do with them? I never felt like I had natural talents. Sure, I had things I liked and was “good” at (reading and writing, to be specific) – but how could I make a career out of that?

Fast forward one year and I’m now a student at McMaster University with plans of becoming the best female lawyer Canada has ever seen. Until of course, I took a Communications class and my world completely changed. Up until that point, I had never heard of public relations nor did I really understand the dynamics of social media. It was 2009 and I was barely on Facebook at that time. But, it only took a few classes before I realized I was destined for a career in Communications.

I switched my program and set my sights on a career in PR. I didn’t know anyone in this field so I became obsessed with research and learning how to succeed. I quickly learned that the key to success would be internship experience and so my (unpaid) intern journey began soon after.

From that moment on, I gave up every single summer while in university to intern. From a hotel PR agency, an elderly home, to the internal PR team at Joe Fresh to the sales and merchandising team at Michael Kors, I was committed to gaining as much experience as I could in the field. Save for the hotel PR gig, I had to land these opportunities completely on my own. I taught myself how to write good emails, an intriguing cover letter, how to stand out in an interview, set up my Linkedin profile and of course, how to dress well for the workplace.

career journeyAttending LG Fashion Week sometime between 2010-2012
career journeyAttending the 2010 Teen Vogue Fashion University in NYC

Every experience I got was through reaching out, following up and demonstrating my value and passion. Also during this time, I became the fashion writer of my university’s paper. My husband (who was my boyfriend at the time) used to affectionately call me “superwoman” as I was successfully juggling a number of different opportunities. I was doing well in school, writing great pieces for the newspaper and had tons of internship experience and connections under my belt. At that time, I felt on top of the world and that my career was pretty much set in stone. Oh, how things change.

career journeyMy husband and I at some point in university, likely 2011
career journeyPosing on campus for a photoshoot with McMaster University’s student newspaper

career journey
My dad and I on my university graduation day

After graduation, I landed another internship where I performed really well (and could have received a full-time job opportunity) but I felt as though it would be important in the long run for me to get certified in public relations. The program at Humber College had a great reputation as I had set up a number of “coffee meetings” with successful graduates who all emphasized the program’s importance. At the time, I also was beginning to make another shift – instead of traditional PR, I wanted to specialize in an emerging field – social media.

The program flew by and very quickly I reached the end where you’re required to complete an internship in order to officially graduate. I’ll be completely honest – I thought this would be easy for me. I had tons of experience and felt as though I could just find a full-time job instead of an internship. After all, I grew up with the belief that good grades and experience automatically equals a good job. Well, I certainly learned that this is not the case – I was the last person in my class to find something but I eventually landed a contract Social Media Coordinator job.

The job didn’t really pan out in terms of becoming a full-time job due to budgets. I ended up unemployed for a month and a half – the longest month and a half of my life. “This is not the life I envisioned”, I’d say to myself after watching yet again another episode of Ellen, going on yet another coffee date and submitting countless job applications. It was a low point for me. Now, I know that a month and a half isn’t anything to complain about and I’m not trying to sound entitled in any way. In fact, I should be grateful that it wasn’t any longer. I admit, I certainly went through an “expectation hangover” during this time. In other words, I had built up some high expectations based on what I learned from family, teachers and just society, in general. My unemployment experience didn’t fit within those expectations and it was a rude but necessary awakening for me. I finally opened my eyes to the realization that the job market is tough.

Eventually, I got a great public sector job as a Communications Coordinator. Good salary, interesting role and I felt excited to be back on my path to “success”. It was a maternity leave contract but with the opportunity to continue on afterwards. I worked hard in this role and felt very confident that I would be staying on. Until of course, I got the inevitable news – there’s no budget to continue my contract. AGAIN. Once again, I’d be out of a job but this time, 3 months before my wedding.

You can only imagine how stressful that time was but thankfully I managed to find something quite quickly and I didn’t have to deal with another extensive unemployment period. The bonus? It would be my first permanent job. I was ecstatic.

I was content for the first year but eventually, this wasn’t enough.

career journeyMe after being recognized as one of PR in Canada’s Top 30 under 30 in 2015

I felt a bit stuck. I was now several years into my career and I was still a “Coordinator”, a junior title by most standards. But, this time instead of the usual “there’s no budget”, I was now faced with another issue – there was no room for me to grow. As much as I didn’t want to compare myself to others, I couldn’t help but feel inadequate as I’d scroll through Linkedin and see my peers moving up into more senior roles. Now, maybe you’re thinking, “Why wouldn’t she just apply for other jobs?” Well, I did for a long time. Nothing ever materialized but I believe my heart just wasn’t in it. I kept thinking about what would happen if I found yet another job and then I encounter the same issues. I was feeling really defeated.

Maybe if I create a life outside of work, I’ll be fine.

The best way I can describe it is that I started to feel this gaping hole in my life and I realized I needed more than just my job. I needed a passion. Four words that came to me almost 3 years prior on a walk home started to keep me up at night – Do Well Dress Well.

So, on February 1st, 2016, I mustered up enough courage to launch DWDW. Originally intended to be a simple side hustle but it quickly flourished into something beyond my wildest dreams. Just a few months afterwards, I began consulting with some wonderful women which led to speaking which led to hosting networking events and eventually some recognition by brands. I also privately launched a consulting business with my husband and we began to get client work.

2.5 million Canadians, especially those aged 25 to 44, are taking part in the “5-to-9’er” lifestyle. (source: Paypal Canada)

After 1 year hit, I began to ask myself – What if I worked for myself full-time?

career journeyCelebrating my 1 year anniversary of hosting networking events

Do Well Dress Well has become this magical thing in my life. It has brought me so much joy and happiness in ways I can’t even begin to explain. When I talk about my growth plans, my heart actually swells with excitement. But, I never realized how much that was noticeable to others as so many people have asked me “so why don’t you just run DWDW full-time?”

Every single time, I’d brush them off. No, I want to build my career. No, I want to save money. No, I just bought a house. I felt like it just wasn’t something I could do.

At the same time, it’s something that I wanted more than anything. I felt as though my career growth was always in everyone else’s control, but mine. The “corporate” world wasn’t working out for me and maybe it was just a sign that I was meant to become my own boss. I truly felt as though I was stuck between a rock and a hard place. I could go out on my own, an option that I was sure would be difficult both emotionally and most certainly financially, or I could stay in my “9-5” and continue to feel frustrated – an option that felt just as (if not, more) difficult to accept as entrepreneurship.

Economic changes have shifted as risk has shifted from organizations to individuals. People are now forced to become more active in managing their own career growth and retirement. (source:

I went back and forth and had a lot of emotional breakdowns. I felt like my hunger for entrepreneurship was wrong. I would get angry at myself for not being happy for what I had. By most standards, my life was pretty secure and traditional. So why am I now trying to mess that up?

Fast forward to when I had a very serious conversation with my parents and husband. What if I tried this? After all, I’ve been an intrapreneur (an “inside entrepreneur”, someone who drives innovation within an organization as an employee) for several years which has positioned me to feel extra confident in myself and my abilities – a topic I recently wrote about on

A few conversations and planning sessions later, I realized that I’m more prepared than I thought and entrepreneurship is actually a viable option right now. Wait, whaaaat?!?

So, today – November 30th, 2017 (my 26th birthday) – is my first official day of self-employment.

career journeyPhotography by Gooseberry Studios

Wow, that was weird to write.

But, I’m doing this. I’m really doing this.

I’ll be running my consulting business Vision Vertical and of course, continuing to create content on Do Well Dress Well and hosting ideate networking events. I also have a few other fun ventures up my sleeve.

Now, don’t get me wrong. Behind my smile and excitement is a whole lot of nerves. I’m not all starry eyed and thinking that this whole self-employment thing will be a breeze. In fact, I’ve been bracing myself for the complete opposite so that I don’t have a complete breakdown when things get tough. I also don’t know if I’ll be an entrepreneur forever. It’s way too early to say but I definitely wouldn’t feel ashamed if I went back to a corporate job in the future. I’d be way more ashamed if I was able to look back 10 years from now and I still didn’t take the chance on myself.

I’ve been living for exactly twenty-six years but today is the first time in my life where I can actually say I feel alive. That comfort zone I’ve lived in up until now? It no longer exists and I couldn’t be happier. I’m now free-falling and yes, the thought of slamming face first into the ground has kept me up the last few nights but I keep reminding myself…there’s a good chance that I could fall but what happens if I fly?

63% of independent workers have started their businesses out of choice rather than necessity (Source: Upwork and Freelance Union)

When I visualized my future as a corporate employee 10 years from now, nothing would come to mind and I would become extremely frustrated. Until I realized it’s not because success isn’t in my future – it just means that the job I want just doesn’t exist and it’s up to me to create it.

As you’ve learned through my personal experience (and possibly have experienced first-hand yourself), work is changing. It’s not the same workforce that my parents or even my grandparents worked in. In order to prepare Canadians for these changes, Futurpreneur Canada has launched, an online content and resource hub with a goal of creating national awareness around employment and the value of entrepreneurship.

Over the next few weeks, I’ll be writing and creating content for the Work is Changing campaign, a collaboration that couldn’t be more timely as I begin this new chapter in my life. In addition to my recent piece on intrapreneurship, I have two other pieces that will be going live soon and I’m excited to share that on Thursday, December 7 at 1:00pm EST, I’ll be hosting a live interview on the Futurpreneur Canada Facebook page! I’ll be interviewing Toronto entrepreneur Rachel Kelly, Founder of Make Lemonade, Toronto’s newest coworking space for women. I hope you’ll tune in to the interview and I encourage you to actively read the site and follow #WayWeWork on social media.

To everyone who has supported me along this journey – my absolutely amazing family and friends, the Futurpreneur team and the many women who choose to read and support Do Well Dress Well, thank you so much from the bottom of my heart.

A few days after resigning from my job, I was sharing my news with my grandmother (who became an entrepreneur later in life) and she said, “Well, I understand that this is what you have to do. Your grandfather was at the same job for 30+ years before retiring but times have changed. That doesn’t happen anymore.” Grandma, I couldn’t have said it any better myself.

Work is Changing and now so am I. It’s time to become the boss lady I’ve always known I was meant to be.

This post was sponsored as part of my collaboration with Futurpreneur Canada but of course, all experiences, opinions and photos are mine.

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  • Jamie
    November 30, 2017 at 11:25 am

    This is amazing! I’m so proud of you! I know you will excel at self-employment.
    I’m taking the same plunge next year and while I’m terrified, I am excited as well.

    • Chanele
      December 1, 2017 at 2:21 pm

      Thank you so much, Jamie! It’s hard to ignore the nerves but I think if we weren’t nervous, we wouldn’t be on the right track. It will never be comfortable to take a risk but calculated risks lead to greatness! Best of luck when you take the plunge! 🙂

  • Iqra
    November 30, 2017 at 11:37 am

    Loved this post babe! It was not only easy to read and inspiring but so much like my own journey and I find its so important to surround yourself with like-minded entrepreneurs especially if you don’t have family support always, like I have often experienced. Can’t wait for the interview with Rachel and to follow along on more of your journey and the content you create!

    • Chanele
      December 1, 2017 at 2:23 pm

      Thanks for reading, Iqra! It seems as though this is an experience many people have had! I agree with you – family support is so important and I definitely would not be doing this if they didn’t believe in me. I’m excited for the interview with Rachel too! I appreciate your support so much. Thanks for following along on my crazy journey! 🙂

  • Daeyz
    November 30, 2017 at 12:56 pm

    Congrats! So excited to hear more about your journey!


    • Chanele
      December 1, 2017 at 2:24 pm

      Thank you, Daeyz! I’m excited to share my experiences with everyone – the good and the bad!

  • Jem Castor
    November 30, 2017 at 6:56 pm

    I read every word, clicked every link and shed a tear every time it hits close to my heart. I’ve said this to you in person but I couldn’t more proud to call you as my biz bestie. I can’t wait to see you blossom and achieve even more than you already have!

    • Chanele
      December 1, 2017 at 2:25 pm

      Don’t make me cry! You have been there for me from the very beginning and you continue to be the most special part of my journey. I’m honoured and proud to have you as my friend and biz bestie! Love ya!

  • Jessica K
    December 19, 2017 at 12:30 am

    Wow… Chanele, what a post! I read it word for word and couldn’t stop. I knew about this as we’ve chatted along the way about the possibility. And here you are, already having taken the plunge! Thank you for sharing your journey to entrepreneurship. As you know, we share so much in common… and its so funny that our entry into entrepreneurship are merely a few months apart from each other too! I’m always super interested in following what you’re up to. Keep up the good work and continue to inspire others!!

    P.S. This sentence REALLy moved me. I don’t think I could’ve said it better. THis is exACTLY how I feel!! “I definitely wouldn’t feel ashamed if I went back to a corporate job in the future. I’d be way more ashamed if I was able to look back 10 years from now and I still didn’t take the chance on myself. “

    • Chanele
      December 19, 2017 at 12:24 pm

      Thank you Jessica!! I know, it’s so crazy how we’ve had such similar experiences. Through writing this, I realized how my story isn’t that unique at all – there’s so many of us going through the same experience. Definitely very grateful to have connected with you though – we’ll have to set up some monthly Skype calls so we can keep each other updated 🙂