5 Years at Redstone: 5 Lessons Learned in Taking Risks, Staying the Course, and Believing in Yourself

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In celebration of being with Redstone for 5 years, Vice President, Maddy Marchildon, shares her 5 lessons learned in taking risks, staying the course, and believing in yourself.

  1. Say yes… for the right reasons 

Just over 5 years ago, I was approached with a concept. A new way of thinking about managing associations and not for profits in Canada, and worldwide. Having been in the industry for 5 years already, ready for a break, and feeling unsure about my next career move, I’d be lying if I said it was an easy decision for me. I knew there was risk involved – Bailey and Carly were completely transparent about the financial position of their brand-new company, including the fact that I was only guaranteed three months of employment while we embarked on this journey.  

For me though, the biggest risk wasn’t the financial uncertainty or losing the network of relationships I had built over the last 5 years. I had already made the decision to leave the company I was with at the time and was strongly considering leaving association management altogether. Despite having started my job search already, I lacked clear direction and motivation on my next career move. 

So why did I say yes? I was sold on the vision and the leaders. I couldn’t yet fully see how this experience was going to be different, but I knew I believed in Bailey and Carly. Their enthusiasm was contagious, and their openness and vulnerability in sharing both their excitement and fear of the unknown is what made me jump on a rollercoaster of start-up life. When you believe in something as much as they did, and the confidence they had in me and my abilities, I knew that no matter what they’d have my back, and everything would turn out okay.  

  1. There will be ups and downs 

The first year at Redstone was a bit of a blur, filled with extreme highs and lows. The feeling of securing our first small association in Ottawa around the 6-week mark was incredible – we knew Redstone could continue to keep me employed beyond three months! There were also exciting conversations about about business planning around Carly’s kitchen table, countless nights out filled with networking and well-rehearsed elevator pitches, and forming close bonds with one another that would help us prepare for whatever laid ahead.  

We had some of our network from our ‘previous lives’ (as we like to refer to it) reach out to us to join the Redstone family. Whether it was having spent a few minutes over the phone walking someone through a membership renewal form, going out of our way to meet with someone at a conference, or staying in touch just to say hi and see how someone was doing – people that had worked with us remembered us and wanted to work with us again. 

While I felt rewarded that these conversations led to business success, there was something missing. This made it difficult to get through the lows that come from start-up growing pains, like long days, limited staff, and rejection. In the next 2-3 years, we doubled in size each year, going from 4 full-time staff and an intern to 20 people and growing. While operating in such a fast-paced environment, I found that I wasn’t stopping to ask myself why. Why this type of work? Why this career path? What is my next step, personally? I started realizing that no matter how great my successes were on paper, my feelings, attitude, and my ‘why’ needed to be in line with what I was doing to feel rewarded. And this takes work in of itself! Despite the successes, we achieved as a team and the supportive network I had, I did not always feel connected to the work, lacked confidence in what I was doing, and often ignored how much my imposter syndrome was really affecting me.  

  1. Find your ‘why’  

In 2017, for personal reasons I made the decision to leave Redstone and to be honest, I didn’t think I’d come back. How my life evolved during those few months off made me take a long hard look at my values. I started wondering what I was looking for, and what kind of job would make me happy. I don’t want to say that the actual work I’m doing doesn’t matter, but I realized what matters way more to me is that I share the same values as Redstone’s leaders. They are what drives me to succeed, and they are the backbone of the decisions that we, or I personally, make. I want to grow and continuously learn, and I chose to transform my lack of confidence into deciding what I want to learn. I realized that I want to feel valued, and to trust those I’m working with. I chose to listen to the validation I was receiving from my bosses, colleagues, and clients, instead of focusing on what I was lacking. I want to make a difference in the lives of the people I work with – whether that is a team member learning alongside me, or a volunteer trying to make a difference in their industry. After realizing this, I came back to Redstone after two months having finally found my ‘why’. I felt refreshed, more confident, and open to new possibilities.  

  1. You don’t need to “know it all”  

I’ve since learned I don’t need to know all of the answers. Earlier in my career, I felt like not having an immediate solution was not acceptable. Even though my bosses never pushed me for perfection, or made me feel like I wasn’t good enough, I put these expectations on myself. Learning from this, at Redstone we began to create a culture where mistakes are okay, and so is asking for help. I realized that none of us have all the answers, but this is actually a good thing – we’re here to learn! As we have continued to grow, we try to look for people with the qualities, skills, and diverse backgrounds that we don’t already possess so that we have the strongest possible team, as a whole. ‘People’, being appreciative and respectful of all the people we work with, and believing that this makes for better relationships and better results is one of Redstone’s core values. I believe that we embody this every day, and that if I encounter something that I don’t know, there is likely someone on our team who I can learn from. 

  1. Stop to celebrate your successes  

Anyone who has worked for a successful start-up will tell you that it’s a mixed bag of emotions. One second you could be celebrating a new contract, and the next you could be dealing with an unhappy client, the threat of losing business, or even worse, a pandemic! But if you don’t stop and live in the moment, and pause to celebrate those wins without worrying about what’s coming next, then what’s the point? Now at 50 staff members and growing, we love to share each other’s successes through Teams messages, in our weekly e-newsletter, or through email and meetings. Celebrating and recognizing successes as a team, especially now that we are all working from home, has also brought us closer together.     

Reflecting on this journey now, it’s crazy to think that all of this happened in just 5 years – it feels closer to 10 years when looking at the incredible change we’ve gone through. But I can honestly say that the only thing I would change is that I wish I believed in myself sooner. 

I could tell you the top 5 lessons learned about business or association management, but those lessons aren’t why I work for Redstone and with associations. I could also tell you about how my role has evolved from being ‘all hands’ and account coordinating on all of our clients to now being the Vice President of Redstone. But at the end of the day, everything comes back to relationships, trust, and the people that I work with – the rest is just details.  

Here’s to many more years with Redstone! 

Check out some of our other content from our 5th anniversary in 2020:

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