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! 🙂

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  • Daeyz
    November 13, 2017 at 11:07 pm

    Aaah loved this read! I kept up with the rally through various tweets, but I am seriously considering purchasing a digital ticket. Would you recommend it?


    • Chanele
      November 13, 2017 at 11:55 pm

      Thanks for reading, Daeyz! I would recommend a digital ticket as there definitely was some great knowledge gained from the speakers. If you ever get the opportunity to experience it in person, I would recommend that even more as the energy in the room was amazing!

  • Chloe
    November 14, 2017 at 1:30 am

    Love this breakdown of the event! I was definitely following your tweets all day!! (I’m @MoltenLala)

    I’m a little miffed I didn’t get some of the things you got in your giftbag! I also had a GA ticket and didn’t get the sunscreen or the phone grip which are two things I would have LOVED. It’s a great bag though so it’s hard to be mad about something so superficial as that. It’s just a little annoying to realize that behind the scenes some things fell through the cracks.
    Hopefully it’s something that can be improved upon next year! I had a great time at the even and the giftbag was just a lovely bonus.

    • Chanele
      November 19, 2017 at 10:39 am

      Thanks Chloe!! Aw that’s unfortunate that our GA bags weren’t exactly the same! If I knew, I definitely could have given you the sunscreen as I just had to leave it behind! I agree, it was a great bag so we can’t stay upset at those little issues for very long. Hopefully the 3rd rally will be the charm and they’ll fix all these little things! 🙂