Steer Your Boat Which Way You Please, Captain!
Written by Heath Chan
I attended Bold at Work’s Good Work Design Circles in September 2024. When I came across their instagram post a few months prior, I thought it sounded interesting, and having had some experience being coached before, I thought why not give it a try.
As I recall what happened a year ago, it now occurs to me that the experience did give me support as a budding freelancer in the facilitation space.
To give a bit of context, I spent most of my 20s, unsure of what I wanted to do. After dropping out of the business degree program I was enrolled in (I felt so tired and dissatisfied of studying for exam grades), I decided to go out and explore. I tried out many different jobs - first F&B as a waiter, then bartending, working in a clinic, book-keeping, ops and admin at an architecture firm and finally 7 years doing ops for a small finance company. The people facing jobs were fun and I loved the connections I made with people. On the other hand, the back end jobs I did were very draining for me and I felt like a zombie those years. When I chose to go out to explore, I was tired of living in the same robotic way that I had lived for 12 years of schooling life. There was a desire to really live - to choose what I really wanted with idealism and a sense of adventure and curiosity. Up to this point, I still felt emptiness and a lack of agency.
When covid came, the emptiness reached a tipping point for me and it was showing in my interactions with people. I didn’t realise it then, but in many of my conversations with people I came across, I would be talking about this emptiness I felt. With every conversation I had, people would share with me their own experience or a story they heard from someone else that would give me another idea to try. Then someone I met on my journey suggested facilitation and coaching. This was a pivotal turning point for me and I began my journey into facilitation.
I realise now as I am writing, that I could end up writing a whole memoir if I don’t focus and structure this blogpost a bit more - haha. Ok, Heath- focus!
Heath as a freelance facilitator in schools
Which brings me to my time with Bold At Work. At the time I had been exploring facilitation as a freelancer mostly in schools for more than a year. It was still a very anxiety-inducing experience to stand up in front of a classroom of students - many of whom don’t want to go through another boring class and some with seemingly judging faces. I still went into every class feeling unsure of myself and needing to show that I knew what I was doing.
I had been for some coaching and already knew how it could change my trajectory towards something better so when I came across the good work design circles, I decided to try it out! I knew too by this time that a big part of enjoying my life was seeking out new experiences and perspectives.
When I walked into the co-working / cafe space in the CBD where the circle was being held, I felt very welcome. All the warm smiles and open hearts from this group of mostly girls and ladies. I think it was also the nature of the social and health space - which I realise now I love so much.
Heath and Karyn (coach), matched during GWDC
We had a group of about 10 -15 of us including coaches going through the frameworks for personality and industry matching. This was led by Jocelyn who I experienced as being very warm, bubbly and engaging. We met our own personal coaches who we had some say in choosing and I was matched with Karyn. Karyn felt very different from me and when I first met her, I was wondering whether it was a good fit. We had 3 sessions together and over those 3 sessions we met at a few cafes. In every conversation, while I did feel some resistance because of my perceived difference but I also noticed her difference in perspective and way of being helped me to see and try something different. My preferred way of connecting is to be open and vulnerable whereas Karyn was more professional in her boundaries. I recall that during a particularly difficult moment during one of our sessions, her words gave me strength and I could park the emotions arising within me and collect myself.
The sessions ended with a group sharing at another co-working/cafe space with us doing some activities together. The one I remember was where we drew and wrote out the life we want for ourselves and that helped me to connect back to what I really wanted in my life. It gave me clarity on the facilitation journey I was on. Although I did not have much experience and did not have confidence in my skills, facilitation was the craft I was willing to struggle for. The open sharing from all the participants and coaches created that space of safety and clarity.
Fast forward to a year later, facilitation is much more clearly a profession and vocation I see myself doing for the long term. Following the design circles, I became an associate facilitator with Bold and now get to learn and do meaningful work with other experienced and uniquely different facilitators. I have also connected with other facilitators and trainers in the social impact space who are actively pursuing causes that matter to them and that truly energises me.
From experimenting and adjusting along my journey as I gained more insight from the experiences I had and people I met, I feel like I am living in a way that suits my own preference for fluidity and agency, social connection and meaningful work.
The one thing I really appreciate about the good work design circles and bold at work community was seeing how there are many more options. Life doesn’t have to look like one path. As I think about this, an image of a river with many smaller tributaries branching off comes to mind. There are many paths to choose from. While going down the river, we can still look at the various options ahead of us, and choose which one to steer towards. Haha, that’s my cheesy metaphor! Hehe.
"Good Work Design Circles 2025 - Doors of Possibilities (Year End Edition)". The programme objective is to aid youths in designing their lives and careers by exploring their identities and skills, confronting challenges and prototyping their way to a fulfilling future. The program is a collaboration with NYC as part of Youth Capabilities Development initiative, with desired outcomes including career preparedness and mentoring, with a focus on supporting youths in jobs and the future of work.
