Shifts are hard (one)

Part 1 of 4 series to share methods to cope with shifts. I define shifts as significant changes in your career and life. This post will share the context of my experiences to explain future posts that will cover skills to practice emotional agility. Follow this series to learn more about the practices I use to help understand, cope, and reflect the scenarios described below.

As I shared in my first post, I changed a lot of my life all at once in May of 2018. It wasn’t easy, and luckily Shopify provided internal career coaches for leads. This post will share the experience and emotions I experienced during that time.

The 5 shifts in my career and life

• Exec to Senior Lead (Group Product Manager (GPM)
• Berlin to Ottawa
• Startup to Hyper-Growth Company
• Design to Product Management
• Social Platform to Commerce Platform

This is overwhelming if you really think about it. Right? I’ve experienced some of these shifts before and I was prepared for some of the changes but not all five at once. I was surprised that the support structures from before had simply failed. These five combinations created a compounding effect that almost broke me. Following are the summaries of each shift and the challenges:

Exec to Senior Lead

For a long time in my career, I was on a trajectory. My aim was high. I wanted to be a GM (General Manager). I think deep down I still one day may want to be a GM but only time will tell. So, I was on that path. I went from Principal Design Manager at Microsoft to Head of Design at Soundcloud to VP of Design at SoundCloud to a Chief Product Officer at Hubrick. I reached an all-time high as a CPO before I had turned 40. Amazing! I was also head of the Berlin office which involved; securing funding, acquiring users, hiring a stellar team from marketing to infrastructure, developing cultural values, and so on. 

I loved many moments of being a chief product officer. I felt accomplished and the job was satisfying. However, it drained my personal life. My days and weeks were long. I would spend time with my kids but my mind was always thinking about work. When I chose to go to Shopify I thought leaving a senior executive role would help me spend time with my family. What I didn’t realize is that I got used to the role, scope, and accountabilities.

Being in a senior lead position is a different role and scope. You are more hands-on delivering in multiple areas and leading only a few folks. The CPO role is where I led a team of 50+ and had managers of managers. Each of those roles requires different skills. As a CPO, I was leading a vision, strategy, and direction. I also played a role in consulting on our financial modeling, fundraising, and meeting potential investors or clients. I partnered with my peers and teams to develop a culture where everyone felt self-accountable to driving outcomes for the company. My role was to ensure our product was producing the results we needed to maintain our operations. I also enjoyed leading our teams across marketing, design, product management, infrastructure, backend & client engineering. 

In my role as a senior lead, I lead 5 large product areas with 3 product managers. I spent my day to day working with my discipline peers in data, marketing, design, and engineering through the phases of feature development. While it was fun, I found that I had outgrown some skills. It didn’t feel as rewarding or challenging (however, I did love learning more about the e-commerce domain). Other skills that also felt missing for me was setting a vision, strategy, leading others, career development, coaching, and pitching. As a middle manager in a company that is quite top-down, I found it hard to fit in. Much later, I recognized I was mis-leveled.

Berlin to Ottawa

The move from Berlin to Ottawa was not easy for me. Also, note our relocation support was okay but we had several challenges with our movers who damaged a few items. They also lost several pieces of our furniture, several boxes, a bike, and a few other items. It was not easy, but the point is the cities are entirely different. In Berlin, the transit is wonderful for a family and there was no need for a car. I found myself enjoying the duality of family life and a social life. I loved the music scene with favorite musicians touring and events hosted in Thai park.

My family, however, didn’t love Berlin. My oldest son in school was bullied both in international school and in German public school. My husband didn’t take the time and effort to learn the German language and struggled socially because of it. 

Ottawa, on the other hand, promised a great life for my boys where my husband could both speak the language and socialize. The boys could also enjoy the outdoors by fishing and hiking. Ottawa offers all four seasons and a fair amount of snow. This meant we could go to the nearby slopes or ice skate on the Rideau canal. 

Canadian schools offered french immersion and the boys could learn yet another language. This might seem trivial but the social scene is dismal. Very view artists tour in Ottawa. Restaurants have a narrow curve of culinary variety. We are, after all, foodies. I was conflicted.

I wasn’t finished with living in Europe. I felt my stay in Berlin was too short for many reasons. I wanted my kids to fully develop a second language. I still had so many places I wanted to visit. I also had felt part of a community in Berlin. I could get to many spots locally and run into someone I knew. We could have a chat and agree to meet up later. I also loved being part of the startup culture there. In hindsight, I wasn’t ready to leave and I left for my family, not for me. I felt I needed to sacrifice my choice for them and later found myself unhappy. 

Startup to Hyper-Growth Company

Being at a startup means that you are doing anything and everything that it takes to get it done. You stretch yourself thin and learn new skills on the fly. At Hubrick it was amazing. I learned how to support our teams with our Head of HR. I learned how to launch a pre-beta and a beta. I learned how to set up our product for algorithms with our data scientists. We also decided to launch a mobile app after the company was initially focused only on the web at the time. 

The impact was incredible and the outcomes were even more amazing. I could see our teams excited and our customers starting to use our products. We had done it and we were onto something. Unfortunately, three months later the company failed and closed shop based on the redirection from our CEO. This was the reason why I had left.

On the other hand, a hyper growth company is at a different stage. They had already IPO’d and were scaling fast. Every other Monday people were on board and before I knew it I had more context than 25% of the company within four months. By year one, I had 45% more context, experience and was one of four who had the most domain knowledge for our team’s accountabilities. There were so many new people. I spent most of my time onboarding others onto our teams rather than setting them up for success and providing support. However, at Shopify, you are rewarded for outcomes and not for supporting others. So I did find the company culture to be difficult. However, I’ll be honest, I loved both types of companies and in the past I’d also worked at corporations and consultancies. They all have their trade-offs and I find this shift was the least concerning. 

Design to Product Management

This was not a new shift for me and I find it hard to think that this would be a challenge alone. I have led five product managers previously as a CPO along with other disciplines like engineering, design, and marketing. I was seen as a great leader for the team and we grew our craft together as we shipped. I also worked closely defining product strategy, vision, features, and specs. As a product leader in a start-up in the early days it was much easier. I was responsible for the strategy and high level pitching to the board for fundraising. 

My shift as a product manager at Shopify was different because I became accountable in a domain I knew only a fraction about. The product management role is primarily accountable for the domain, business, and other competitors while working with engineers, marketing, and designers to deliver products. You are often spending your time gathering requirements and synthesizing information. Your day to day tools are documents, spreadsheets, and communication channels. Product managers often communicate the strategy and tactics while the designer is responsible for telling the story and showing the experience. You spend time in tools that help you research and craft stories. Switching from design to product management in a domain that I am not well versed in was a significant shift which leads to me discussing the next shift:

Social Platform to a Commerce Platform

This was the most difficult shift I ever experienced. I started working on software in 2004 at Nokia and we worked on connecting people. Later, I worked on T-mobile, Skype, Microsoft Teams, and Soundcloud. All of these have aspects of social media either through mobile devices, software platforms, or services. I understand how people communicate; the why, the what, and when. I’ve participated in years of research and design for these types of products. I’d become a domain expert over the course of fifteen years. 

Abruptly, I had changed my domain to commerce. This was 100% intentional because I wanted to learn. We had started to scratch the surface at Hubrick and with Shopify it offered a massive learning opportunity. Being a product manager in a new domain is a disaster. They say you can do this, and you can, but you need the support of your teams and your manager. I managed to gain domain knowledge but it took much longer than I had expected. While I would recommend others to do the same, I would not suggest so many shifts all at once. However, I have learned so much and I have no regrets.

As you can see, five shifts are incredibly hard!  I would recommend that if you are considering a shift- try one, two, or maybe no more than three at time. Five can be quite difficult. I’ve grown so much through these changes. 

I have had many people reach out to me for advice on this topic. They often start off by saying “You are amazing! You have reinvented yourself so many times”. I have grown as a leader. I suspect this is because I’ve experienced many shifts like these. If you do choose to take on a shift or several shifts, follow these posts. I’ll be sharing the practice of emotional agility tools and how Shopify helped me in this arena.