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Finding Purpose through Loss: Meet Gilly Cannon

Finding purpose through loss meet Gilly Cannon

As you know, I recently announced my upcoming RAIN Sessions, an interview series about Callings.

Here’s the plan: I’ll interview people and share their stories. I’ll meet virtually with folks called to their best work through tragedy, lay-off or firing, illness, inspiration, … you name it. The series will focus on real people’s real stories about how dark times (or bright vision) guided them to something different, bigger and better than they might have imagined.

I’m looking for success stories! I want to bask in inspiration. As you may know, I got sick and my healing process guides me and my work. I now help people find their own callings, their purpose, and take inspired action to create a love affair with their work. My health continues to gradually improve and I’m in love with my work and my clients, but I’m still healing and still working toward the new vision. I’d love to hear more success stories, more evidence for inspiration. And I think you might, too.

I might also use RAIN Sessions to spotlight clients — what they do, neat projects they completed, challenges they overcame– and other fun stuff.

Following is the first interview! I was mesmerized by Gilly Cannon’s story and the beautiful work that found her through loss. I’m honored to share her story with you. (Plus she’s got a gorgeous accent!)

Finding Purpose through Loss: Meet Gilly Cannon

Below you’ll find an outline of the answers Gilly provided prior to the interview (not a transcript). 

What kind of work did you do before you felt called to new work?

I was a Teacher, math specialist and principal in the UK and director of a learning support program in an International school in Hong Kong.

Was your prior work fulfilling? Did you excel at it?

Yes and yes in hindsight. It was also stressful and my confidence in myself was sorely lacking.

What occurred that made you change course?

Did you encounter something difficult, like tragedy, illness, burnout, getting fired or laid off? Or was is something positive like a jolt of inspiration, a powerful idea, or something so alluring that it demanded your attention?

Just before coming to the USA my father had died after a year’s battle with colon cancer in the UK. He was 59 when he died and I had traveled back and forth from Hong Kong 7 times in 1 year to see him. I had to prepare my 3 and 5 year old sons to say goodbye to him and support my sister who was fresh out of medical school working in the hospital as a doctor where my father was dying. My mom was 57 and we all felt we’d had a limb severed.

We moved to the USA for my husband’s job 2 years after my father’s death and 8 months after our 3rd so was born. I didn’t have the right to work for 8 years after we came, so I did a lot of volunteer work and a big piece of it was volunteering at a Hospice. I also created and started a community program in my Dad’s memory called Bringing Books of Comfort.

Did your purpose/calling come to you in a flash or was it a series of events, moments, insights?

It was a series of events and a yearning to understand where my father ‘was’ after he died. Books dropped off book shelves in airports like “Talking to Heaven”. I wasn’t afraid to sit with people who were dying or to have difficult conversations. I dreamt about my father telling me he was ok.  When I ached with the pain that he should have had more time, I heard a whisper saying he’d actually been given extra time and had lived longer than he should have.

I started the Book project, volunteered at a hospice visiting the dying. Then when I got my work permit, I was asked to work there managing the hospice volunteers. Suddenly my husband got very sick and needed brain surgery. As he recovered I realized I couldn’t take care of dying people since I was a full time caregiver in my own home. I knew another hospice had a grief support program and I went to volunteer with them offering Good Grief Clubs to grieving children in schools.

What are/were you called to say or do?

2 years after I started, the job came up for Directing the Bereavement programs. I was drawn back to the advert over and over, but it was full time and I still had young kids and a sick husband. So after speaking to the hospice professional who had trained me, totally out of character I emailed the executive director and asked if I could see her. I went and told her I would love to do the job but could only work part time. She said she was really looking for a full time person but perhaps I could do special projects.

2 days later, she called me and said she’d split the job in to 2 and would I like to apply for the Director of Children’s bereavement job. The rest is history. I am now in my DREAM job.

What do you do now?

I’m Director of Children’s Bereavement Services and a Life Coach -Trained by MBI

What actions did you take to shift into this new work? What did you let go of?

I volunteered in the area of work I wanted to be in professionally. I stepped way out of my comfort zone to go and ask for the job I wanted. And I had to let go of not having the ‘right’ qualifications. That limiting belief- “I’m not qualified enough.” rears it head often.

How do you define success? Where are you in relation to your definition?

My current job really is a meeting of my passions, calling and skills. I am in the sweet spot. Every day I use so many of the skills I’ve acquired from my education, counseling, life coaching, volunteering and volunteer coordination experience. When I look back at my resume, everything I have done was one step closer to this job.

What now wants to come through you and your work?

I am in a job I never thought I would be qualified to do. I want others to know it’s never too late to find what brings meaning into your life. Advocating for children’s needs at one of the most vulnerable times in their lives. Raising awareness about how children grieve and that children are often called the forgotten mourners who need support in their own right.

What legacy to you want to leave?

I need to think about this one. (Answered beautifully in the interview.)


Know someone who has been through a painful transition and found or created success in a new way? Is it you? Whether you know an interesting story you’d like to nominate or would be willing to share your own, I’d love to hear from you!

Email me at jennifer@rainmakerresume.com (or comment on this post), reach out via my Contact form, or give me a call. 406.530.9249. I can’t wait to hear your story. 

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