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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.

10 Canadian Female Entrepreneurs You Need to Know

According to a 2015 TD Economics special report, Canadian women have been leading the charge into entrepreneurship since the recession and the number of self-employed women continues to rise today. Our businesses may currently be smaller than our male counterparts (although at the rate we’re going, I highly believe this will change), we’re way more innovative and this same study found that female-owned small businesses are more likely to have engaged in innovation (significantly improving or creating a completely new good or service).

It’s not surprising though. As I learned through Futurpreneur Canada’s Work is Changing campaign, 46% of the Canadian workforce is currently at risk of being replaced. That’s a huge percentage. Consequently, people are confused, frustrated and are in search of some job security – a job where they are in control.

Additionally, our lifestyle habits are changing. In general, Canadians are in search of better work/life balance but if you break it down by gender, the TD Economics special report highlights that women prioritize this way more than men.


With November 19th marking Women’s Entrepreneurship Day and I wanted to take the opportunity to highlight some of the entrepreneurs that have each inspired me way more than they know. Whether full-time or part-time, entrepreneurship is not easy and although more of us are turning to it in hopes of creating a more flexible lifestyle, it still has it’s challenges. Regardless, these women continue to work hard, create amazing products and services and remain humble while doing so.

Here are 10 Canadian Female Entrepreneurs You Need to Know:

Katie Zeppieri

When I think of female empowerment, Katie immediately comes to mind as she passionately works everyday to empower women and girls. She is the Founder of GIRLTALK Empowerment through which she inspires, empowers and mobilizes girls to become world-changers! She’s also the Founder of This Box is Pink, a monthly subscription box for girls & women with lifestyle products that not only make them look and feel good but also DO good. Oh, and she’s the author of GIRL TALK Book. Earlier this year, I met Katie for the first time as I invited her to speak on The Why Women Panel, a small networking event I hosted for women to discover their why. She openly shared her story with the audience and was just so kind and genuine.

Victoria Stacey

If you’re looking for a DIY guru, Victoria is your girl. I’m convinced that she can pretty much make anything! Victoria is the Founder of Florals and Teacups through which she blogs on everything DIY and she hosts plant-inspired craft workshops all across Toronto. I met Victoria through her volunteer work with the Toronto Chapter of Young Women in Business and since then she’s become someone that I will always go out of my way to support. She also just became the new DIY Content Creator at Diply so she is truly showing no signs of slowing down when it comes to her passion for crafts.

Rachel Kelly

After life actually handed her a lemon, Rachel literally made lemonade by creating Make Lemonade, Toronto’s newest female coworking space. I absolutely love the space and she has done an amazing job filling what was once a large void in our city. Her space offers desks, tables, meeting rooms and a variety of different events. Plus, Rachel is so friendly which makes visiting the space an even greater experience.

Laura Benn

Laura, my favourite go-to photographer, is the Founder of Gooseberry Studios, a storytelling studio that specializes in cinematic photography and custom branding services. Throughout my personal journey over the last 2 years, Laura has consistently been someone I can count on whether it’s through partnering on blog content or capturing photos of me in a way only she knows how. She is such a kind soul and also one of the most hardworking women I know.

Julene Chung

Julene is the mastermind behind Curated Life, through which she creates empowering lifestyle events and media content for millennial women. She is the Editor-in-Chief of Curated Life Magazine which features business, beauty, travel and health content which was recently named a Finalist in the Canadian Magazine Awards – Mag Grand Prix. She also hosts her signature event series MASTERCLASS. Each event connects attendees to a community of peers and the resources required to start and/or grow a prosperous business. She does an amazing job of bringing women together and providing them with opportunities – I’m honoured to have had the opportunity to contribute some of my favourite books to a past issue.

Karen Swyszcz

Karen is the Founder of Makin the Bacon and she helps small businesses learn how to blogging, branding and social media for business success. I first met Karen through Instagram and she’s become one of my favourite business owners to follow for her down-to-earth personality and valuable business tips. She’s an expert on all things blogging and most recently became an instructor for a Writing for Social Media class at Sheridan College.

Huda Alvi

Huda describes herself as a life influencer and that couldn’t be anymore accurate. She uses her life experiences to inspire, influence and empower others. She’s a serial entrepreneur – she started her first company at 18 and then again at 25, she opened Istaff Management, her own recruitment firm, which was able to succeed just short of a million-dollar company within its first year. Now, she’s been hosting various classes called #WORKSHOPSBYHUDA where she, alongside other experts, teaches on topics like photography, blogging and YouTube. She’s also the Founder of the #IAMMORE movement, a storytelling platform for people to share their stories from all over the world. Oh and she’s also working on launching a tech start up all while continuing to build a strong, inspiring personal brand.

Jam Gamble 

When Jam says that she is the #SlayerofTheMic, she is not lying. She slays the mic every.single.time and I can personally attest to this. She really is the Connector of People, Ideas and Energy as her infectious personality instantly brings people together and you can’t help but focus on what she has to say. She hosts everything from weddings, corporate events and public campaigns. She also recently developed the Slay the Mic program in order to coach people looking to become more confident public speakers. It’s also worth mentioning that she does all of this outside of being a full-time highschool teacher. I don’t know how she does it all but she manages to succeed and always looks good while doing it.

Alethea Robinson

Althea is the Founder of See Girl Work, providing content strategy, blogging, and writing & editing services for creative agencies and small to medium-sized businesses. She also runs a popular blog that has become a valuable content hub for creators, marketers and freelancers. Recently, she was invited to join Paypal Canada’s Small Business Growth Council as an ambassador to inform, educate and inspire other Canadian business owners to embrace the power of e-commerce. Her blog has become one of my personal favourites as she consistently creates quality content to help women succeed.

Cristina Maritano

Cristina is the lovely lady behind ShoeTease, a shoe blog she created to talk about shoe trends, shoe styling, shoe care and more. She’s a Paris trained designer with an obvious passion for all things shoes and accessories. In addition to running her blog, she also launched a pom pom shoe set collection called Pombons (the perfect way to add some personality to your shoes!) and she consults with small businesses on how to leverage search engine optimization (SEO). She creates such gorgeous content and is probably one of my favourite people to follow online.


Girlboss Rally Review – November 11, 2017 in NYC

As I write this, I’m currently sitting in LaGuardia airport waiting for my flight back home to Toronto. I could be playing around on an airport iPad, buying an overpriced meal or cracking open my current read (The Power of Moments, if you’re curious) which I’ve been meaning to finish. I tried to “relax” and soak up my last few minutes of my New York City weekend but quite honestly, I can’t stop thinking about the day prior. My first (and certainly not last) Girlboss Rally experience. I said it on Instagram and Twitter and I’ll say it again, I had an amazing time!

In a world where we are surrounded by photo filters, staged photos and fake social media personas, it was so refreshing to have a completely authentic look into the reality of inspirational girlbosses, both full-time entrepreneurs and corporate women alike. 

I have received tons of questions about my experience so I’ve done my best to put together an extremely comprehensive review. Remember that these are my open and honest thoughts. I paid for my rally ticket, flight and hotel with my own money and I’m not receiving any compensation in any shape or form for this review. There are tons of conferences these days and my hope is that this post will help you in the future as you make decisions on what to attend. With that being said, grab a drink and a snack and get ready to read! 

girlboss rally review

Why I decided to attend

I read Girlboss in 2014 shortly after it was released. I had recently graduated from my PR post-graduate program and was currently an intern at a social media agency. Like many recent grads, it was a really confusing time. I wasn’t sure which direction to take my career but I knew what kind of person I wanted to be. The book came into my life at the perfect time giving me the courage to go forward with the idea that I couldn’t stop thinking about – this very website that you’re reading right now – Do Well Dress Well. I read Girlboss in July/August and by December of that same year, I had officially purchased my website domain (Note: I didn’t actually launch until February 2016 but purchasing the domain was a huge step for me!)

girlboss rally

Despite the impact the book had on my life, I almost did not attend because of the cost. 

The rally was not cheap by any means. There were two options – $475 for General Admission (GA) and $700 for VIP. Take in mind, these prices are in US dollars which makes it even more expensive for a Canadian like me. Considering I would also have to pay for a flight to NYC, 2 nights hotel accommodation, transportation to airport + food, I opted for a GA ticket which came to roughly $600 CDN. 

So how did I justify spending over $1000+ for this? 

1. I admire Sophia Amoruso’s resilience. 

She is fresh off the heels of a bankruptcy, divorce and Netflix show cancellation – all of which were very public. In what seems like no time at all, she leveraged the immense success of Girlboss to launch Girlboss Media. I was intrigued to be around someone with this much determination and commitment to “redefining success.”

2. I want to build DWDW into a multi-faceted platform like Girlboss Media

Her platform is built around offering great content in various forms – website, podcast, books, events and a non-profit foundation. This has and continues to be my goal with DWDW considering there is nothing like this in Canada currently. I wanted to soak up the knowledge and inspiration needed to continue pushing forward by learning from Sophia who has managed to do so quickly and flawlessly. 

Now, before I get into what I liked and what I felt could be improved, if you’re looking for absolute perfection, the Girlboss Rally is not it. But, that’s exactly what made it great. It was imperfectly perfect. Let me explain:

What I Liked

  • The quality of speakers were by far the best I have ever experienced and I’ve been to TONS of conferences and networking events. They were diverse (not only in terms of race but their careers – some are full-time entrepreneurs and some are killin’ it in the corporate world) and so down-to-earth. Each speaker seemed genuinely excited to be a part of it but also committed to giving the audience REAL advice. I would describe the Girlboss Rally as a “no fluff zone” meaning that the conversations weren’t just fluff – they went beyond the standard “Work hard!” or “Just be yourself!” and I am so grateful for that. I don’t know about you but I roll my eyes whenever I hear boring advice like that.


  • Whoever did the decor for the venue deserves a raise because it was amazing. As soon as I walked in, I felt like I walked into a different dimension. The pink lighting, inspiration quotes all over the walls, creatively designed posters…all of it was just great. 


  • Everyone in that room had a story, a vision or an idea bigger than themselves. It was so inspiring to be in a room with women like myself who are looking to leave a unique mark on the world. Whenever someone would stand up and ask a question, they would often start by introducing themselves. They would say some amazing thing that they’re doing (for example, one girl is going to be a doctor next year but is also running a startup right now) and immediately the room started clapping for her. The energy in the room was electric and I wished I could package it up and bring it home with me to open on those days I’m uninspired. 

girlboss rally

  • You were able to join the Facebook group prior to attending so you could chat with attendees beforehand. Interacting with them made me way more excited and I was able to connect with some awesome women!


  • With that being said, I attended alone but did not feel alone. Everyone was so friendly and down-to-earth and we all helped each other take awesome pictures.


  • The startup studio allowed you to participate in an intimate session to gain some actionable knowledge on a particular area. I went to the one on Venture Capital and I found it SO helpful and I walked away with some resources that will be so valuable when I’m working on pitch decks in the future.


girlboss rally review

girlboss rally review

girlboss rally review

girlboss rally review

What Could Be Improved

  • I’m not a coffee drinker and I was disappointed that tea wasn’t provided. It was a little misleading as I stood in a line to grab a tea as the sign from the beverage sponsor said “Coffee and Teas”, however, only coffee was available at the event. 


  • The event was split into two buildings. VIP guests had their lounge in the main building where all the sessions were held and GA guests like myself had their lounge and food provided in building 2 which means we had to walk outside in the freezing cold to get there. It was only a 2 minute walk across the street but I was a little annoyed by this as I had put my winter coat in coat check as I didn’t want to be carrying it around all day. It would be great if they could find a larger venue so that this wouldn’t have to happen. However, this wouldn’t really be an issue for me if the weather was warmer.


  • That being said, if I wanted to grab a snack, I would have to leave the main room (and risk losing my seat near the front), walk outside, enter building 2 to grab the snacks and walk back. It would be great if snacks were available in the main room, especially for GA ticket holders. It’s a long 12 hour day and having convenient access to fuel would be great!

girlboss rally review

girlboss rally review

girlboss rally review

  • I was underwhelmed by the merchandise available for purchase. To be honest, I would have been willing to spend money on a shirt and/or tote bag with just the simple Girlboss logo on it but, surprisingly, this wasn’t available! Instead, the merchandise had some quotes on it which isn’t usually an issue for me except I wasn’t a fan of the language used. I don’t use curse words on a regular basis so I was a little put off by a totebag that said “unfuckwithable”. For some people it may not be an issue but that just doesn’t fit me or my brand. 


  • The giftbag didn’t consider international guests. Knowing that airport security is no joke, I quickly went through the gift bag before leaving my hotel to check for any “liquid” items. I had to leave behind a bottle of sauce, sunscreen and a box of Flow Water as it would have been thrown out at the airport. I would say they could avoid liquid items all together or potentially have separate gift bags for international attendees. 

Giftbag Reveal 

So, what was in the gift bag?! I decided that it would be a lot more fun to record a short video to show you so here it is! (P.S. I recorded it really quickly and it is not high-quality at all but thought I could show you better than I could tell you!)

Overall, despite the fact that I had to leave 3 items behind in NYC, I’m pretty pleased with the gift bag! 3 books, a bunch of coupons, some beauty items, snacks, affirmation cards and a water bottle.

What did I takeaway from the event and would I recommend it? 


I think we all get to a point in our lives where “success stories” are no longer enough. We want real, actionable insights and we actually want to hear failures so that we can try not to make those same mistakes. If you feel the same way, the Girlboss Rally is for you. 

The success that we see from people we follow online is one-sided. There’s always another side we don’t see. The ugly stuff. The feelings and the failures. This is the stuff that the Girlboss Rally brought right to the forefront in a comforting and reassuring way. 

For example:

Did you know that Gabby Bernstein, New York Times Bestselling Author and Motivational Speaker, was a drug addict by age 25?!

Also, Kathryn Minshew, Founder of The Muse heard “no” 148 times before she got her first “yes!”

Being a Girlboss is glamourized. Instagram (and social media, in general) can fool many women into thinking it’s all inspirational quotes, writing ideas into a cute notebook and grabbing brunch. Yes, inspirational quotes were prominent at the venue but not without the speakers stressing that we just need to DO the work. 

What we see online can cause us to convince ourselves that we need to imitate the “success” of others. This is not true at all and the Girlboss Rally reassured me that I don’t have to change who I am to be successful. We can and we should redefine what “success” means to fit what makes us feel good.

“Success is an inside job. Turn your search for success inward.” – Gabby Bernstein

We shouldn’t be wearing our all-nighters, being stressed or busy as a badge of honour. In fact, as Gabby Bernstein says, we should take these things as a sign that we need to slow down in order to speed up. She also reminded us that we don’t need to be THERE right now. We need to stop working ourselves to the bone as if success happens overnight. We need to just focus on taking intentional small actions towards where we want to be. 

The rally also provided a timely reminder that being a “girlboss” does not = full-time entrepreneur. You can be a boss whether you’re a student, full-time or part-time entrepreneur or killin’ it full-time in the corporate world. Being a business owner is not for everyone. 

In the program, they described the event as a love fest. I agree and I would go as far as to say it was a lovefest of our imperfections and our failures. So often, we’re encouraged to just brush them off, get back up and run forward while pushing our failures to the outskirts of our memory. 

I was really moved when Sophia said:

girlboss rally review

Now, I don’t know if this was intentional but notice how she said she’s carrying it. She didn’t bury it, she didn’t throw it away. She’s moving ahead carrying her baggage and she’s doing a pretty amazing job at it.


If that’s not inspiration enough to love and embrace your failures, I don’t know what is. 

For additional content:

Here’s a recap of my tweets: #GirlBossRally NYC Recap – November 11, 2017

If this post has intrigued you in anyway and you’d be interested in attending next March in Los Angeles as part of a group, fill out this quick form and I’ll remind you when 2018 tix go on sale and we can plan to attend together! 🙂

5 Tips to Successfully Become Your Own PR Person

You create your own content and you have solid expertise in a particular area – but how many people actually know about it? PR coverage or what I like to call ‘Featured content’ is one of the 3 types of content that is an essential part of your personal brand content plan. This type of content includes being interviewed and quoted in other publications that positions you as an expert in your field.

To listen to an audio version of this blogpost, click below!

Of course, public relations is a full-time job and many people hire a PR person to proactively pitch publications for coverage opportunities. But, what if you’re not at the stage to hire someone to pitch on your behalf? No problem, becoming your own PR person is very much possible!

your own PR person

Here are 5 tips to successfully become your own PR person:

Know your pitch

Without a pitch, you’ll be unable to successfully promote yourself and your value. You need to be able to confidently explain who you are, what you do and why you’re credible. Pitching yourself can be nerve-wracking as you worry about coming off as too “cocky”. I like to think of personal pitching as humble bragging. I know, I know – bragging is not exactly a word that people love but there is a right way and a wrong way to do it. (The book Brag!: The Art of Tooting Your Own Horn without Blowing Ithelped me become more comfortable with bragging!)

You need to brag about your value and expertise but in a humble way – which means, you’re not saying something like “Hi, I’m an awesome business owner. I get compliments all the time and no one is better than me because I’ve been featured here and here. I’m great, I’m beautiful and you need to know me.” As true as that might be, that’s not the way to go about things and I can guarantee you won’t get a positive response. Instead, introduce yourself in the context of your motivation – in other words, what’s your why? Yes, your pitch is about you but it’s also about why you do what you do and how it makes an impact. For example, here’s how I typically pitch myself for PR opportunities:

Hi, I’m Chanele McFarlane, Founder of Do Well Dress Well, and I specialize* in content and event experiences that equip millennial women with the knowledge and inspiration to succeed in style. [If I have a little more room, I’ll also say:] Through my website, I cover everything from personal branding, networking, entrepreneurship, career advice and personal style.

*I tweak this when I’m speaking to people in person to instead highlight that I’m passionate about the work that I do, instead of simply specializing in it.

I highly recommend reading the book Start with Why: How Great Leaders Inspire Everyone to Take Action if you want some inspiration in uncovering exactly why you do what you do.

Have your bio and headshot ready

As the saying goes, stay ready so you don’t have to get ready. It is more than likely that as you get featured, you will be asked to send over a short bio and headshot that they can use. You don’t want to miss out on an opportunity by keeping them waiting as you scramble to put together a bio and get someone to take your photo. Before you start proactively putting yourself out there, ensure that you have these two important things prepared and update them regularly so that they’re both the most current reflection of you. Need help prepping for your photoshoot? Read these tips on How to Prepare for Your Personal Brand Photoshoot.

Subscribe to HARO

HARO, also known as Help A Reporter Out, is a platform for reporters to find sources for their stories. So, how does it work and how it can help you? Well, it’s a free tool that both PR agencies, publications, blogs and businesses can use to put out a request – often they are looking for expert sources to include in an article they are working on. You can subscribe to receive daily emails with these requests (don’t worry, you can indicate the topics you’re interested in – and yes, it’s free!) so you can read through them and see if there’s anything that you can serve as an expert source on.

Here’s an example of what the requests look like:

Sometimes the name of the publication is listed and sometimes it is anonymous. As you see something you’d like to respond to, you simply send an email to the email address provided with your expert response. I’ve personally written a few successful emails that have landed in me gaining PR coverage (full disclosure – I have a strong PR background so writing and pitching are my strengths) so my main piece of advice would be to ensure you’re as short and succinct as possible. No one has the time to sit and read a long-winded email. You should include:

  • A short 2 sentence introduction – your full name, title and your blog/business name and what you do
  • Response to their question/inquiry (it should be well-written, straight to the point and if possible, include a unique point of view that would increase your chances of being featured)

Read it over 3 times to ensure you don’t have any spelling or grammatical errors and then… you wait! You won’t always hear back (imagine how many emails they get!) but if they do, that typically means that you will be included in their piece. Most often, they will send you an email to let you know that it’s live and a link to the piece. Be sure to thank them and share it all across your social networks!

Follow the right people

Yes, HARO is an excellent tool to gain PR but in addition to this, you can gain opportunities from simply following the right people. Who are the key players in your industry? Who writes about the industry you’re an expert in? These are the people that you need to be following everywhere – Facebook, Twitter, Linkedin, Instagram and any other platform where they’re present. Follow them closely and pay attention to their posts. You never know when they’ll post about looking for an expert to speak to a piece they’re working on. Trust me, this happens WAY more often than you think and is a great way to land a press opportunity.

Monitor your online mentions

Not all publicity is good publicity. Always keep an eye on any mentions of your name and/or business name to ensure that it is a positive reflection of you. An easy (and free!) way to do this? Monitor your name through Google Alerts to be sent daily reports of any online coverage of your name, business name or any other search terms you’re concerned with.


Any other ways you’ve used to gain PR for yourself? Leave a comment below!


Creating Successful Collaborations: Everything You Need to Know

“Two heads are better than one.”

“Alone we can do so little, together we can do so much.”

“If you want to go fast, go alone. If you want to go far, go together.”

It’s safe to say that whatever quote you grew up hearing, you know that in order to truly be successful, you need to work with others. Regardless of the industry you’re in, finding the right people to partner with will ultimately boost the trajectory of your success.

Click below to listen to an audio version of this post!

To make sure we’re all on the same page, let’s define the word collaboration:

A collaboration is two or more people working toward shared goals

creating successful collaborations

In order for a collaboration to be successful, it can’t be random. It has to be calculated, strategic and mutually-beneficial. This means that you can’t just go to anyone and everyone and say “let’s collaborate!” (more on why that’s ineffective later) but instead, you should spend time brainstorming before you begin reaching out.

Want to start creating successful collaborations? Here are a few questions you should ask yourself first:

What are your current goals?

For example: boost your brand awareness (this can be your personal and/or business brand), land a job, build your network, increase your followers/audience, increase sales

What value do I have to offer?

This is key. For collaborations to be effective, you need to both give and receive value. So, what can you offer? Think about your expertise and potentially the audience and connections that you have access to and can bring to the table

Who are some key people in and outside of my industry that I could partner with?

Perhaps you’ll already have some people top of mind or you may need to do a little social media research to find new people to build relationships with.

Once you have your goals, value and potential people in mind, it’s then time for the fun part – coming up with collaboration ideas! Of course, they would differ depending on who you’re collaborating with but here are a few to get you started:

  • Write a joint blogpost on a topic that you’re both interested in
  • Co-host an event (I’ve done this multiple times with my business bestie!)
  • Create a physical or digital product together
  • Co-host a podcast and/or webinar
  • Organize social media takeovers (one of you takes over the other’s social media account for the day – you get exposed to a new audience and they get content and engagement)
  • Co-host a contest or giveaway

creating successful collaborations

Unfortunately, a lot of people skip the brainstorming step. Instead of being strategic about who they partner with, they end up telling anyone they come across that sounds interesting “let’s collaborate!” The main problem with this approach is that it sounds too generic. But also, what does it even mean? That type of message leaves a lot of questions in the receiver’s mind.

In order to receive a positive response to whatever you’re asking for, it’s important to be specific with your ask – and this applies to anything, not just collaborations. In your initial message, you should include:

  • Address them by their full name
  • Introduce who you are and the value you’d like to provide (to immediately pique their interest!)
  • Give them a genuine compliment
  • Briefly describe the collaboration idea (highlight how it would be mutually beneficial)
  • End with a call-to-action (ask for their feedback, a time to meet in-person or chat via phone or Skype)

Want a message template that you can use to effectively pitch collaboration ideas? I’ve created a free guide! Click the image below to download your free copy!

So, let’s say you’ve done the initial work, you’ve pitched your idea and the other person is on board. How can you ensure that your collaboration is as successful as possible? Here are 4 key tips for success:

Do your research

Once you have a list of people in mind, spend some time researching them to ensure that they’re the right fit. Watch any videos they may have posted lately, scan their tweets and review their posts. Is their image aligned with yours? Is there anything controversial that could potentially tarnish your image? Is there anything they are working on that fits well with your brand? Doing your due diligence is extremely important as the collaboration must make sense to your audience – you don’t want them questioning why you’ve partnered with a particular person!

Be professional

Treat your communication with a potential collaborator like you would in any other professional situation. Address them by their name, use full words and sentences and contact them via email. If you’re unable to find their email address, you can send them a quick message via social media asking for the best email to contact them at.

Clearly outline deliverables

Once you’ve both agreed that a collaboration makes sense, you should take a moment to write out exactly what each person will be responsible for and key dates. For example, let’s say that you’re collaborating on an event. Make a to-do list of all your key tasks, assign a person to each task and the dates they need to be completed by. Doing this will allow you to easily see if the work distribution is fair.

Hold up your end of the bargain

A collaboration is only as strong as it’s weakest contributor. If you decide to let the other person do all the work (but still try to benefit from it!), not only will you very likely ruin the relationship between you and the other person but it will become obvious to your audiences. If you will be unable to commit to the collaboration for any reason, it’s best to be completely upfront and honest with the other person as early as possible so you can try to postpone for another date or call it off completely.

creating successful collaborations

But when it comes to the importance of collaborating, don’t just take my word for it. I asked 3 entrepreneurs about their thoughts on collaborations and why they are key for success:

“As a blogger, collaboration is a key component of keeping my content fresh, interesting and relevant. Whether it’s working with guest bloggers, graphic designers, photographers, or other creative talent, I wouldn’t be able to keep up with producing a high volume of content for my readers without successful collaborative efforts. In order to be truly beneficial for both parties—it’s important to communicate the shared value, parameters and timelines. Be open and flexible. Ofter more than you ask for. It will always be returned 10x over.”

Alethea from See Girl Work 

“One of my favourite things about collaboration is the community it allows me to build. Whether I’m collaborating with a brand to showcase why I love them to my online audience, building relationships with local small businesses for my events, or working with friends and other like-minded individuals to put together something great, it gives me a sense of belonging and the foundation of building a community around my passions.” 

Victoria from Florals and Teacups

“Collaboration means partnership. It means working together with other business or brands to create a final product to demonstrate skills or to further brand reach. Of course, sometimes collaborations can be just for fun, to shake loose the creative juices and create something for portfolio. There are a lot of things to consider for creating a successful collaboration, but here are my top four pieces of advice: Be respectful of the other person’s time and skills (paying attention to little details will show the other person that you understand they are busy and that their time is valuable. Plus it will more than likely increase the likelihood of getting a response!), approach individuals who align with your brand’s values, remember that “mutually beneficial” is not a dirty word (be sure to outline how the partnership could be useful and valuable to the other person’s goals. And please don’t say, “It’ll be great exposure,” because that is not a finite deliverable or necessarily worthwhile for an established business and don’t passively wait for a collaboration if you want one. Be the idea-maker and driving force behind a collaboration. Don’t just wait for other people to approach you. Get out there, knock on some doors (virtually of course) and ask!”

Laura from Gooseberry Studios


Hopefully this inspires you to start dreaming up your own collaborations! Remember, collaboration divides the task and multiplies the success. Find the right people to partner with and it will be one of the best decisions you’ll ever make for your brand.

Don’t forget to download your free copy of the Well Done Collaborations guide! Get your copy here:

Why You Need Allies, Sponsors and Mentors in Your Network

In 2014, I attended an interview at an internationally known marketing and advertising agency. I was still 2 months away from completing my full-time Public Relations post-graduate program but I had seen the job posting online and thought it would be perfect for me.

A few weeks later, I received an email to come in for an interview. I remember walking in and feeling nervous yet really confident. I knew my stuff, I had some great practical experience and I had my portfolio in hand to prove it.

The interview finished and then I was told something along the lines of…

“We’re really impressed by you and we’d love to offer you the job…but you’re still in school!”

I was crushed but yet I don’t really know what I was expecting as I still had 2 months left before I finished my program. I wasn’t about to “drop out” so close to the finish line either. So, they told me to keep in touch and email them when I finished school.

Click below to listen to an audio version of this blogpost!

Fast forward to being a few weeks away from finishing my program (thank goodness!) and I decided to follow up again to see if there were any open roles. I received a response shortly after from the hiring manager I had interviewed with and in a nutshell, she felt that I had so much potential and even though there weren’t any open positions, she wanted to share me with her network and if I’d be ok with that.

…Um, yes, of course!!

So, this woman who I had only met once (and talked to for no longer than an hour), sent out an email to her network saying how much potential I have and if they have any open roles, they need me on their team.

I didn’t know it then (I honestly just thought she was extremely nice!) but I know it now, this woman was a sponsor – a very important person that everyone needs in their network in order to truly succeed.

We often throw around the word “network” without much context or thought to the roles that the people in our network play yet there are 3 key ones that you absolutely need to get ahead – allies, mentors and of course, sponsors.

Here’s who they are and why you need all 3 for professional success:


According to this Zen Workplace article, an ally is someone who proactively offers help and support to help you achieve your goals.

An ally goes beyond just a friend you have at work. You’re able to have open and honest conversations about salaries and career advancement because they genuinely have your best interests at heart. They will also work to push forward your ideas and ensure your work is noticed. If you work in a male-dominated field, it’s also recommended that you also have a few male allies that you can trust to really boost the trajectory of your career. These male allies should recognize their privilege within your workplace and industry and genuinely be committed to helping you succeed as well.


By definition, a mentor is an experienced and trusted advisor. As described in this Levo League article, mentors set aside dedicated time in order to offer up career advice and share wisdom and experiences to their mentees.

I’ll be honest – I’ve never had a mentor. Sure, I’ve had people here and there that have set aside time to share their insight with me but never a formal mentor/mentee relationship. I know that a lot of importance is placed on mentorship and I’m sure there is lots of value in it but typically they can only take you so far. They succeed at boosting your knowledge and confidence by sharing their experience and insight but I’ve learned that sometimes there can be a gap between equipping you with this knowledge and actual opportunity.


A sponsor is someone that is willing to put their name and reputation on the line to vouch for you. They share you with their entire network to help you land opportunities.

According to Jo Miller, Founder of Be Leaderly, “A sponsor sees how your strengths could add value in areas of the business you’ve not yet had exposure to. Due to their influence, sponsors can open more career doors than you ever thought possible. And they can see a vision for your career that is bigger than you could ever imagine.”

The interesting thing about sponsors is that you don’t necessarily find them – they find you. After all, I definitely did not know that my interview would result in me having a sponsor!

As this article in Forbes says, “finding a sponsor is far more difficult than finding a mentor. Generally, young professionals choose their mentors, whereas sponsors choose young professionals to bet on.”

Author Bonnie Marcus talks about this idea of being “sponsor ready”.  Essentially, this means you have to consistently perform at a high level and always make a good impression so that you’re a person that a potential sponsor would have no worry about associating themselves with you. Think about this the next time you go for an interview. Even if you don’t get the job, if you make a positive enough impression, you could end up with a valuable career sponsor.

Now, you may be wondering – what value does a sponsor get? Well, it’s a 2-way street. You get access to a potentially hidden network and they become known as someone who has access to high-potential people. They become a valuable asset to the people in their network.

If you’re lucky, you’ll have people that fill multiple roles. In fact, that’s probably the best case scenario to have – someone that not only dedicated time to share their insight but believes in your potential so much that they vouch for you in front of their network.

But, remember – it’s important to pay it forward so just as you seek to fill the roles of allies, sponsors and mentors in your life, look for opportunities for you to play these roles as well so you can make a lasting impact on someone else’s career.

4 Ways to Continue Your Education as a Working Woman

When I was in university, I told myself that as soon as I graduate, I would never go back to school again.

No more essays. No more textbooks and definitely no more exams. Needless to say, I was eager to get out into the working world.

Until of course, I entered the working world and realized I had it pretty good as a student compared to navigating the working world. Because…the job market is tough.

There is extremely high competition for open jobs and it can take countless applications and interviews before you find something. This also means that once you get a job, your hard work isn’t over. In order to keep your job or move into a new role, you have to remain competitive and keep your skills up to date.

With job expectations changing all the time, it’s a good idea to regularly look at job descriptions that are similar to your current role (or even better – one that you are aspiring to!) to see what skills are expected.

But, how do you find the time and money to update your skills when you work full-time?

Here are 4 ways you can continue your education as a working woman:

Sign up for a Brainstation class

After doing my regular review of job descriptions in my field, I realized that it was time to brush up on my skills. With my background in digital marketing and communications, I wanted to know what the next big skill was and I noticed that “User Experience” was consistent among all of them. Fast forward about a week and I was officially enrolled in the 5-week part-time User Experience Design course at Brainstation located in downtown Toronto.

I’m sure many of you are probably wondering – what in the world is User Experience? Well, user experience is the quality of a person’s interaction with a product or system. The course focused on websites and apps and I found the content to be extremely relevant to anyone – whether you work in digital marketing or not!

I really love the culture at Brainstation and I found it to be a quick but valuable way to gain new skills in a short amount of time. A Brainstation course is so different from the traditional post-secondary institution as you’re taught by instructors that currently work in the field and everything you learn can immediately be applied to the real world. Another great thing about them? They offer scholarships to help make the course cost more affordable.

Thinking about signing up? Click here to get $40 in Brainstation credit that you can use towards courses, workshops and events! I’ll also get $40 in credit too, so I may just see you around sometime ;)*

Watch a TED Talk

Not only are TED Talks a great source of inspiration (watch one on a day you’re feeling uninspired and you’ll see what I mean) but they are full of educational content. What’s great about TED Talks is that a wide variety of subjects are covered which means you’re guaranteed to find one that piques your interest. You can search by subject via the TED website or a simple search on YouTube will do the trick too!

Watch a course on

Lynda is a video-based online learning platform that allows people to learn business, software and creative skills. They were acquired by LinkedIn in XXXX and since then they’ve seamlessly integrated the two platforms to help take your professional career to new heights. When looking at a job description, LinkedIn will recommend relevant courses that you should take on Lynda to help you increase your qualifications. Plus, you can literally take your courses anywhere as you can watch the video via the mobile site or their apps – perfect for when you’re on the go! Sign up for a free trial to see how you like it.

Take the CEO 60 Challenge

What do some of the world’s top CEO’s have in common? Aside from of course, having tons of money. They typically read 4-5 books per month to an average of 60 books a year! There is so much knowledge to be found within books and many CEO’s have said that their best ideas have come from being inspired by a recent read. Now, I’m not saying that you necessarily have to read 60 books as well but it’s a helpful reminder that education doesn’t always mean classes, textbooks and exams. There are so many options for consuming books from e-readers, audio books or good ol’ physical books if you’re old-fashioned like I am. Don’t forget – magazines are a great way to learn too. I religiously read the physical issues of Entrepreneur Magazine and Fast Company each month as each issue is packed with informative articles.

What’s your favourite way to gain new knowledge and skills?

Full disclosure: I was a Brainstation brand ambassador while enrolled in my course which allowed me to receive a discount on my course. Regardless, I still would have taken the course and I still would honestly recommend it as a viable option for continuing your education. Brainstation did not sponsor this post and the opinions I’ve shared are my open and honest beliefs! 

6 Ways to Give Your Personal Brand a Fall Refresh

The start of the fall season is always an exciting time. As the weather begins to cool, it’s like we all snap back into reality as we say goodbye to yet another summer and prepare to conquer the remaining months of the year. There’s no shortage of events and career opportunities in the fall with many of us finding our calendars quickly book up!

You’ll be meeting tons of people at said events (potentially attending interviews too!) which consequently leads to more people viewing your social profiles as well.

To ensure you’re fully prepared for these impending outings and opportunities, let me ask you this – when was the last time you updated your personal brand?

Here are 6 ways to give your personal brand a fall refresh:

Update your headshots

Your profile photo is the first thing that people look at on your social profile. If yours is a quick selfie you took on your own or just a completely outdated photo (perhaps your hair is drastically different?), it’s time to make a change. Hire a photographer or ask a friend who can take a decent photo to help you take new headshots. Not only will it immediately refresh your online profiles but it is always good to have a professional set of photos on hand for any speaking or promotional opportunity you may receive.

Before your shoot, be sure to check out my post on How to Prepare for a Personal Brand Photoshoot with tips from myself and photographer Laura Benn from Gooseberry Studios!

Update social profiles

Started a new job? Recently worked on a new project? Add and edit details on your social profiles, especially your bio! Make sure your LinkedIn profile reflects your current role and all section are complete. You can always read up on How to Get an All-Star Profile on LinkedIn for a full checklist.

Check your business card supply

With all the networking events you can attend this season, you should make sure you have an ample amount of business cards ready to go. Order more if required but before you do – ensure that your information is up-to-date so that people can easily get in contact with you!

Update your wardrobe

Now this doesn’t necessarily mean you need to go out and get a completely new wardrobe but it’s a great time to complete a strategic audit of your closet. Check for the wardrobe essentials and add any necessary pieces that will help you get through the fall season (and into the winter season!) in style. Don’t forget – a wardrobe change can boost your productivity!

Review your goals

Have you been achieving your goals? With only a few months left in the year, it’s a great time to sit and reflect on what you’ve accomplished and what you still have left to work on. My goal-setting process typically involves setting both short-term and long-term goals but everyone’s process is different. However you choose to do it, be sure that your goals are SMART (specific, measurable, attainable, realistic and timely) to increase the likelihood of actually achieving them!

Another way to ensure you’ll achieve your goals? Writing them somewhere that you’ll see them everyday! I’ve been loving the Better Life Planner from the Better Life Project, a success planner designed for life long learners! Now, this is not just your average planner – it has nice big pages to write ALL of your tasks plus you can track your goals each month and week! And did I mention you can also keep track of your reading lists and gifts you need to buy? Get your copy of the Better Life Planner to help you finish 2017 strong and start 2018 on the right foot! Use my code DWDW15 for an exclusive 15% discount!

Analyze your social media and content strategy

To consistently position yourself as an expert, you should be leveraging social media and content with a well-devised strategy. By far, building your personal brand using content is one of the most valuable things you can do to gain new opportunities.

How will you be giving your personal brand a fall refresh?


Note: The Better Life Planner discount is an affiliate link which means I may receive a small commission from your purchase. You should know that I very rarely share affiliate links and if I do, it means that it’s a product I truly do love and trust! 🙂 

5 Steps to Getting Event Sponsors

Over the past 18 months, I’ve had the opportunity to host 5 networking events and by the second one, I was able to secure support from various sponsors. Yes, the events were still relatively new but the numbers don’t matter as much as value. Without value, it doesn’t matter how many attendees or social media impressions you have. You may think that your event is “too small” but it may be exactly the type of event a company is looking to support.

But, let’s be honest – reaching out to sponsors is nerve-wracking! Between finding the right people to contact, drafting the emails, waiting patiently for responses (you’ll probably refresh your emails every few minutes) and dealing with rejection, landing sponsors is not easy. However, if there’s anything I’ve learned since organizing my own events – nothing worth having comes easy and you don’t get what you don’t ask for. Yes, it’s nerve-wracking to reach out to potential sponsors but if you successfully land sponsorship support, it can truly help to elevate your brand.

Here are 5 tips to help you get event sponsors:

Create a strong sponsorship package

It’s imperative that you have a short yet concise document that you can share with your sponsors that highlights exactly why they should get involved with your event. Here are the key things to include:

  • Who you are and your expertise (what’s your background, why are you passionate about this and what makes you qualified)
  • Details on past events (attendee numbers, photos, positive feedback – highlight your growth!)
  • Attendee demographics (describe your attendees by age, interests, location, professional background, etc.)
  • Benefits of sponsoring your event (a.k.a. What value can you provide them?)
  • Testimonials
  • Sponsorship options (will you provide pre-set packaged opportunities or customized options?)
  • Contact information

Research and create an outreach list

When it comes to sponsorship, don’t just throw spaghetti at the wall and hope it sticks – in other words, don’t reach out to anyone and everyone and take whoever responds. You need to be specific in terms of who your ideal sponsors would be so that it makes sense for your event. Take time to research and ask yourself the following questions:

  • What brands can best integrate into your event and provide value?
  • Who has sponsored events similar to yours?
  • What brands do our attendees like?


Create customized emails

Once you have a targeted list, it’s time for you to start your outreach. I highly recommend trying to find emails for a specific person – emails sent to a general mailbox rarely ever receive responses. If you can’t easily find the best contact from the company’s website – don’t get discouraged! Here’s what I do:

  • Look up the best contact on LinkedIn
  • Once I have the first and last name, I research to find out how the company structures their email addresses (for example – is it firstnamelastname@company, firstname.lastname@company, etc.)
  • The quickest way to find out how the company structures their emails? Search for a recent press release and check the contact details at the bottom!

Before you start reaching out, it’s important to know exactly what type of support you would like from them. Take some time to brainstorm some ideas so that if they ask you what you have in mind, you can respond right away. Be direct yet reasonable in your requests.

Your emails need to be short but valuable and from the first few sentences, you need to make clear what’s in it for them. Start by addressing them by name and then briefly introducing yourself, what you do and the value you provide. Let them know your package is attached for them to review and be sure to end the email with a call-to-action so that they’re more likely to respond – you could ask to set up a call or a meeting to provide them with more details.

I also suggest creating a tracker so that you can keep a record of all the emails you sent out, what date and the responses you receive. This way, you’ll be able to effectively follow up.

Keep the communication lines open

Once a sponsor has agreed to partner with you, it’s important to openly communicate with them both before and after the event. Provide them with all of the event details and update them on any changes that may occur. Also be sure to respond to all emails within 24 hours.


Your follow-up after the event is extremely important. If you’re able to maintain the relationship, you could potentially have a permanent sponsor! Within 48 hours, send each sponsor a thank you email with pictures and stats from the event. I also suggest sending a handwritten thank you card within 7 days to really show your appreciation for their support.

Now, let’s be honest – you could follow all of these steps and still receive a No. If you do (and it’s very likely that you will receive a few of them – that’s just life), do not let it discourage you. Move forward and continue reaching out because you’re sure to find the right company that completely believes in your vision and will help to take your event to the next level.

Would you be interested in an e-Book on all things event sponsorship, including more proposal tips, screenshots from successful sponsorship packages, email templates and more? Leave me a comment below!