For the past few years, I’d had a nagging feeling that the work I’d been doing was not the work I was meant to be doing. I mean, I was pretty good at it and felt generously compensated for it, but it just never felt right. Maybe you’ve felt this before as well. 

After spending a summer of conversations and reflections, I’ve decided to commit to the pivot. I’m calling it the “commivot.” (Okay, maybe there’s a better word for it!)

As anyone who’s made a career pivot before knows, it’s scary. And just that much scarier when it means you’ll be venturing into the world of entrepreneurship.

If one does not know to which port one is sailing, no wind is favourable.


This post is about the process I went through in deciding to make the shift. I’ve been working with an incredible career coach, Andrea Fruhling, Founder of Doubleknot Works, and with her permission, I’ve shared how we created clarity for my next big move.

For those of you who are thinking about making a change, I hope you find this post helpful. It’s a personal account of my experience but I’ve tried to explain the activities so you can do them yourself.

And even if you aren’t in the process of shifting, I hope it helps spark some ideas on how you can craft a career that brings you more creativity and fun.

First, a bit of context.

For a year, I’d been talking to my former employer about the idea of moving on from the organization. The role in sales I’d been in for a couple of years just wasn’t for me. It was scary to talk about it to my boss but she was incredibly supportive of the idea, and we discussed a timeline for my transition.

What’s that saying about plans? Turns out they don’t always go as planned.

Long story short, the timeline was cut short when I was let go in May. As those who have experienced a layoff know this, it’s not easy being let go – even if you’d been planning on moving on at some point. And for a couple of weeks I was licking my wounds and relied on my friends and family for their support as I worked through my emotions.

Deep inside, I knew this was the right thing. Sure, it wasn’t my choice to leave at that time (especially during a global pandemic!) but I was all-in now. I was pushed off the plank and now I had to learn how to swim on my own. As cliche as it sounds, it’s a liberating feeling when you know you have your own destiny in your hands!

Reflection #1: What do you do for fun?

I started to work with Andrea in June. I decided to work with a career coach because I knew the pivoting process wouldn’t be easy. I’d be facing resistance everyday as my “lizard brain” would make me look for the safest and comfortable option. If I was going to commit to this transition, I was going to need help.

One of the first activities we did together was sharing what I do for fun in different situations. Instead of approaching situations in my default way, what if I could make decisions and face challenges in a fun or innovative way?

We looked at all aspects of my life including approaching unemployment, work life, going to the gym, podcasting and blogging, managing my finances, and my relationships. I wrote down what I typically do in my default mode followed by what I’d do if I was approaching it in a fun or innovative way.

What feels fun, creative and innovative for you?

One of the first few questions Andrea Fruhling, my career coach, asked me

As I worked on this list, a few themes emerged about myself:

  • I like variety in challenges and learning something new in the process. (If someone paid me to be a student for life, I’d take that offer in a heartbeat);
  • I enjoy collaborating with other people to identify the root cause of a problem and developing potential solutions;
  • I love the early stages of strategy development – brainstorming, discussing and planning;
  • I enjoy working in small teams that have a high level of trust and collaboration;
  • I love learning and using my discipline (probably my greatest strength) to diligently work towards acquiring a new skill;
  • I enjoy work that’s more “project based” as I get to start fresh with a new challenge I can tangle with.

These realizations weren’t new. I knew many of these things, but it was helpful to write them out and see the patterns emerge on a Google Doc. To add to that, asking myself the question “what work will be fun, innovative and creative for me?” became a powerful question to guide my career planning process.

Inspired by my conversations with my career coach, I mapped out my career journey thus far.

Reflection #2 – Prioritize what matters to you

The second activity that was really useful was ranking my Workplace Attractors. These are elements of work that drive our sense of fulfillment. She walked me through the list below and asked me to rank them in a pyramid structure.

  1. Innovation (doing something new)
  2. Work Fit (finding work that fits my interest, values, etc.)
  3. Relationships (working in a group, interpersonal connections)
  4. Learning (opportunities for growth, professional development, new challenges)
  5. Contribution (sense of purpose and meaning and doing work that has meaning)
  6. Security (financial, having benefits, position security)
  7. Flexibility (time off for other needs and work/life balance)
  8. Recognition (being appreciated for what you’re doing)
  9. Responsibility (being trusted to take on responsibility)
  10. Location (physical space, healthy workspace)

After some back-and-forth, here’s what mine ended up looking like this:

What was surprising to me was how “Work Fit” landed at the very top of the pyramid.

In the past, I’d chosen to work for organizations because I believed in their mission. My first job out of university was in a small town in Mozambique doing microfinance work. I then followed that up working at a youth focused social enterprise. 

Making an impact (i.e. contribution) was an important part of my career story, but it turned into the only story I was telling myself. While I wouldn’t change a thing about my career journey so far, reflecting on this made me realize that I was sacrificing the other attractors for contribution.

So it makes sense that Work Fit now takes the top spot in my career search. I want to do work that lines up with my strengths and skill sets I want to develop. That’s not to say other elements are not important, but it’s important for me to prioritize the ones that will drive the most fulfillment in my next role. This will sustain enjoyment over the long term.

Reflection #3 – Connect emotionally with your path

The third and final activity we did was one that I’ll call “The Perspective Shift.”

Andrea asked me to set up my living room with three separate chairs. Each chair represented a potential career I was interested in. I’d been considering a wide variety of ideas including exploring design thinking, coaching/consulting, taking a mindfulness teacher certification, etc. 

As I sat in each chair, Andrea asked me to share how it felt being in that chair. Going through the process with each career option which allowed me to think about the aspects of work that got me excited. It also brought up potential questions I’d need to answer to better understand each option.

I have to admit, it felt a bit weird doing this activity. There were so many unknowns and it felt uncomfortable to talk about each career option when I hadn’t even taken the first step. Not to mention I’m in my living room talking to myself and a couple of empty chairs.

But looking back, I realized the point of the exercise was to feel what it might be like to commit to a path. We often ignore our feelings in favour of our thoughts. I’m particularly bad at this as I tend to over analyze and forget to trust my gut.

By visualizing what it might be like to go down a path, it helped me uncover a strong interest I had in a concept called design thinking. I didn’t know much about it but I knew it had to do something about using a process/framework for creative problem solving. Based on the “what I do for fun” exercise I had done earlier in this process, the idea of tackling different problems and understanding root causes got me very excited about exploring this topic further.

This is the real secret to life – to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play.

Alan Watts

In weeks following this activity, I took an introductory course on the topic from a leading design thinking agency in the world and started connecting with a variety of people who are in the space.

I was able to start answering the questions I had in my head about this topic and began to build more confidence that this was the right path forward. All it took was a bit of visualization and connecting with my gut feeling to get me started.

Three Key (+ One Bonus) Lessons

So there you have it – three reflections that helped me work through my commivot! There’s a lot that I shared above so I’ve summarized the key lessons learned below:

  1. Discover what your “North Star” is and remind yourself throughout the process. For me, it was about pursuing work that feels fun, creative and innovative. If you put aside making money, what might fun look like to you? If you could design your own role from scratch, what would you do?
  2. Do the Workplace Attractors exercise and stay true to the workplace attractors that are important to you right now. Be mindful of the “career story” that you’re telling yourself. E.g. I studied “x” so I have to be “x”. Many of the most successful people in the world started in a field that had no direct relation to the work they do today.
  3. Invest in a career coach. A good coach will be there to provide a framework, question unhelpful stories about yourself and hold you accountable to taking action. If Michael Jordan had a coach throughout his career, I’m pretty sure we should all have one too.
  4. Finally, be patient with yourself. Arriving at a decision to pivot took me time. Do the exercises, research your options and let your subconscious mind do work in the background. Build the courage to take that first step.

If you’re working on your own career pivot, I hope you found this useful. I’m happy to be a resource if you’d like to talk about it. Please feel free to reach me at

P.S. I’m running my first virtual design thinking workshop on Friday, October 2nd. (Yes, I’m putting my money where my mouth is!) If you’re interested in a simple process to inspire more creativity and collaboration at your next (remote) team meeting, I’m sure you’ll find it useful. You can learn more about the event and purchase your tickets here.