Reflections on Gather North: The Creation of A Professional Getaway for Women Who Make The Web

It’s been 8 days since Gather North 2015 took place in Prince Edward County, Ontario, Canada. 8 days since 39 women in tech gathered in the country for a weekend to get to know each other better, learn from each other, be inspired and relax. In the last 8 days I’ve been thinking a lot about the weekend, how it came to be, what happened, and how it far far far exceeded any expectations I had. Here are some of those thoughts.

I planned, organized and hosted Gather North with my friend and colleague Sarah Hunter. Sarah and I first met at briefly at a WordPress conference in Toronto in autumn 2014, where I was speaking on a panel about the business of web design. She had some questions for me about working with clients, so we met for a coffee. We chatted about clients, but we also chatted about a bunch of other things, including what tech conferences and events we liked to attend (or wanted to attend). We talked about events that prioritize connection amongst attendees as highly as the actual sessions, and agreed that those were the conferences that were the most attractive to both of us. Sarah and I quickly realized that none of these events were close to us in Toronto… and maybe we should do something about that. Like start our own.

With my partner in Gather North crime, Sarah Hunter, at the Drake Devonshire Inn

I don’t remember all the details of that first coffee date, but I do remember that specific moment when Sarah and I looked at each other, and we both realized… yes. We could do this. We should do this. We will do this. And we were off.

We could do this. We should do this. We will do this. And we were off.

More meetings followed. We started to sketch out our not-yet-named event. An early idea was to rent a large private cottage, since we figured there was no way we’d have more than 10 people interested in attending. But Sarah and I were concerned about there being too much responsibility and liability with renting a private property, so we started to look at other options. That’s when Sarah mentioned the Drake Devonshire Inn. She made a preliminary phone call to see if the newly opened location could handle private events and they said yes, come visit us and we’ll discuss. Road trip time.

Sarah and I drove to the Drake Devonshire Inn, 2.5 hours east of Toronto, on Friday January 23, 2014. There was snow on the ground, and it was overcast and windy. A typically miserable winter day. But when we were at the Drake, it somehow seemed beautiful. The shoreline of Lake Ontario was blocked up with big ice piles, and waves crashed in. Dark clouds over the lake seemed moody and gorgeous as Sarah and I enjoyed a warm fire and tasty lunch in the dining room. We had previously talked about wanting to do a summer event, but that nasty winter day in Prince Edward County changed our minds. If the Drake Devonshire Inn could seem like such a vibrant, hip, and welcoming space in the depths of winter, it could work anytime of year.

Lake Ontario, as seen from the Drake Devonshire Inn, January 2015

We were buzzing with excitement on our drive back to Toronto that day. We nailed down some specifics on that car ride. We agreed on a name: Gather North. We bought the domain name right there on the spot. We decided that Gather North had to be at the Drake Devonshire Inn. Time of year didn’t matter — if anything, the “off season” seemed appealing — more people might be available to attend, and we could save a little on room bookings.

It was decided that Gather North would be specifically for “women who make the web”. Sarah and I were open to interpretation on who that could include — basically, anyone who self-identifies as a woman in tech. Web designers, graphic designers, developers, bloggers, project managers, business developers, content strategists, art directors, and anyone who works on the web (either independently or as an employee) were all welcome. Why women only? It’s simple really. We are a small, but mighty, population within the greater tech community. Sarah and I wanted to create an event that fosters connection amongst women in tech, so we could get to know each other and look out for each other. Whatever form and variation future Gather North events may take, this always was (and always will be) the spirit and purpose of Gather North.

Why women only? It’s simple really. We are a small, but mighty, population within the greater tech community. Sarah and I wanted to create an event that fosters connection amongst women in tech, so we could get to know each other and look out for each other. Whatever form and variation future Gather North events may take, this always was (and always will be) the spirit and purpose of Gather North.

Back in Toronto, we had more meetings. Sarah booked the weekend of November 6–8, 2015 with the Drake Devonshire. We made a logo and a website. I hashed out a very rough and somewhat inaccurate budget of what the whole thing would cost, and figured out how much we should price tickets. We told our friends. We asked Tara Wilkins to help us get the word out through an Instagram and Twitter account for Gather North. We didn’t know exactly what would be happening on the event weekend — we put a message on the website that said meals and sessions were included in the registration, but didn’t give any details on what those sessions would be. We just said it would be relaxing, inspiring, and somewhat professionally related. We still thought 10, maybe 15 people might register, if we were lucky.

Counting down the “sleeps” until registration opened on Gather North’s Instagram

Gather North registration opened on May 15, 2015. 10 people registered that first day. 15 more people registered within the first two weeks. We were at 25 confirmed, paid attendees. Sarah and I were thrilled and slightly terrified. Sarah checked with the Drake Devonshire — how many people could we fit in the event room? Maximum 40 in the seating style we wanted. We were at 25 people. And then 5 more registered. Sarah and I discussed capping Gather North at 30 people. And then 5 more registered. We were at 35 confirmed, paid attendees, and decided we had to hold there. We put a “sold out” message on the website on August 11, 2015. It was three months before Gather North, we hadn’t even announced speakers or session details, and we were sold out with a waiting list.

In late summer 2015, we had confirmed an amazing location and we’d have great food and great swag (all important parts of event planning that can often be overlooked). Sarah and I knew the tone we wanted to set, and the purpose of Gather North. The next step was to program the sessions. I remember looking at the list of attendees, and thinking, “Holy shit, there are amazing women here. We better DELIVER for these people.” Sarah and I compiled a wish-list of speakers that could present on broad topics that would appeal to our attendees (who were coming from such different backgrounds and career paths). We reached out to our list. We asked about speaking fees and travel stipends, because we believe speakers should be paid for their work. And then we realized that I made a huge mistake in budgeting — I didn’t allocate enough money for speakers. That’s when Sarah and I decided it was time to go after sponsors.

A sponsor package was made, with some great content by Helen Tremethick. Sarah and I reached out to every contact we could think of at cool companies that we liked, and thought our attendees would like. We started hustling. We pitched the idea that by supporting Gather North, organizations were supporting women in tech. The sponsors who came on board seemed to “get it” right away. Thank you a million times over, Christy at MailChimp. Michaela at InVision. Lindsay and Colene at Adobe. Marie and Ben at Oki Doki. We literally could not have made Gather North what it was without you and your generous support.

Erin Anacker, Marie Poulin and Shannon Lee Simmons speaking at Gather North. Their appearances were made possible by our amazing sponsors.

With sponsor money in hand, we were able to confirm our speakers for Gather North. Shannon Lee Simmons would give a talk about women and money. Marie Poulin would speak about building a career with intention. Erin Anacker would help us understand ourselves better by defining our core values. And the best part — all three speakers were able to join us for the weekend as participants, so they could experience Gather North along with everyone else. This wasn’t mandatory; it was a happy coincidence that the speakers could stick around. Having Shannon, Erin and Marie there for meals and hangout time was amazing. Gather North attendees could ask them questions, and everyone really got to know each other. Sarah and I agree that this happy coincidence (the speakers being able to participate in the weekend) was a big part of the success of Gather North, and we’ll try to get speakers at future Gather North events to participate as attendees too.

More meetings followed throughout autumn 2015. We made last-minute preparations. Meal plans were nailed down. Custom swag was ordered. Signage was printed. Table-top games were purchased. Use of the Drake Devonshire Inn’s photo booth was confirmed. Excitement on Instagram and Twitter was building. Sarah and I were focused on the details and had a lot to do (in addition to running our own businesses), but we were calm. I don’t think we ever doubted that Gather North wouldn’t be a great event. We just had no idea how great it would be.

The phenomenal women who attended Gather North 2015, outside the Drake Devonshire Inn

It’s hard to describe the feelings of the Gather North weekend. It’s almost like you had to be there to really get it. From the Friday night kickoff, the air was electric. Attendees loved the Drake Devonshire Inn and were happy to be in such a hip and inspiring space. Welcome cocktails were served. Sarah and I made a welcome speech, setting the tone for the weekend. Dinner was in a cozy private dining room, where we passed food family-style at long tables. Even on the first evening I noticed people started talking about attending “next year’s event.” Who said anything about next year’s event?

Saturday flew by in a dizzy blur. Sarah and I shuttled between participating in the sessions and liaising with the Drake Devonshire staff. There were a few small hiccups around serving and food, but the Drake staff corrected things on the fly and were very accommodating. Sarah and I joked that it felt like we were at our wedding, trying to be gracious hosts and anticipate our guests’ needs, while still enjoying the event and trying to have a good time ourselves.

Some of my favourite candid shots from Gather North 2015. See more on Instagram.

By the time we made an impromptu closing speech at Saturday night’s dinner, it was very clear to Sarah and I that something magical had happened at Gather North. We were overwhelmed with gratitude. I couldn’t stop saying “thank you” to everyone. Thank you for believing in our purpose. Thank you for showing up, with your whole self. Thank you for participating. Thank you for making our vision a reality.

After dinner, I casually asked if anyone would like to join Sarah and I for brunch on Sunday morning — something that wasn’t included in the original Gather North plan. 32 of 39 people said they’d be there for brunch and pay extra for it. That’s how much everyone wanted the weekend to keep going. Luckily, the Drake Devonshire was able to make last minute plans and could accommodate all of us for Sunday brunch.

More candids from Gather North 2015

I slept, but I didn’t rest much that weekend. I suspect Sarah didn’t either, because she lost her voice halfway through Saturday and could barely speak above a croak. On the drive home we chatted a bit about the event and some practical wrap-up things we needed to do, but we were both so stunned and exhausted (physically and emotionally) that we couldn’t even begin to process what really happened at Gather North. I got home and crashed.

In the days since Gather North ended, feedback from attendees has started to roll in. And it’s helping me to see that the feelings I had at Gather North weren’t just in my head. Others really did feel it too. We made our feedback form anonymous, so people could be honest with their thoughts. But there isn’t one negative comment in there. Instead, the feedback is full of sentiments like this:

“This weekend has given me so many tools to move forward in life with. Finances, personal growth, even freakin’ family planning — like… EVERYTHING. It was just so positive and wonderful. I highly value the opportunity to connect with other wonderful women and I hope for these connections to continue. #BestWeekendEver”

“Thank you for putting on an excellent weekend and providing the opportunity to meet so many amazing women. It was invaluable and I really want more of this kind of conference. Overall I came home full of new knowledge and inspiration. Thank you thank you thank you.”

“Do it again. And again. And again. It’s no easy to feat to create a conference that is high on both impact and connection. I felt like I learned a lot and I also made friends with women who are doing some very cool work. I don’t know when the next Gather North will be, but I will definitely be coming.”

“Thank you so much for organizing this. I can honestly say it has changed my life at this moment. It was exactly the boost of inspiration, tools, and support I needed :)”

“Thank you thank you thank for organizing such an amazing event. I was initially a bit worried that it would become too woo-woo/just-be-your-best-self-y or (in the opposite direction) too bitchy/catty for my taste, but it did not at all. I’m emotionally exhausted from all the connecting and reflection and inspiration (introvert!) but after a period of resting up I want to do it all over again. More please!!”

Sarah and I don’t know what’s next, exactly. The feeling of potential and where we could go from here seems limitless. It’s so exciting. There will be challenges (one that immediately pops to mind is how to scale so we can be more inclusive, but still maintain a small, intimate environment). We’ll make mistakes, but I’m confident that if we stick to our original purpose and vision, we’ll figure it out. This is only the beginning for Gather North.