Cameron Herold recounts a three-and-a-half-month reset (May 15–Aug 31) during which he unplugged, journaled, and inventoried his career. He identified that he loved coaching, networking, and speaking, chose to stop running operational companies, and moved into fractional COO and mentorship roles (early clients: Karen Stewart of Fairway Divorce; Ken Sim of Nurse Next Door; Razor Solomon of Ilive Rewards). That shift culminated in founding the COO Alliance, an exclusive community for COOs to skill up the second-in-command.
Chapters
I was a fractional COO for Karen Steward from Calgary who ran Fairway Divorce. I was a fractional COO for Ken Sim with Nurse Next Door in Vancouver. And I was a fractional COO for any Razor Solomon from Toronto who built Ilive Rewards. Those three were my first coaching clients. And then that began. Kind of what I do today. And now I have an organization that's exclusively for the COO. I was being mentored by the COO at Starbucks, and I was getting coached for about 18 months by Greg Johnson, who was the incoming CEO at Starbucks. And one of the things Greg had me do when I left got junk mid May, 18 years ago, he had me read the book the Artist's Way. And he had me every morning wake up and just journal for 15 minutes a day. And I took from May 15 until August 31 off, I didn't check any emails for three and a half months, didn't reply to any phone messages. I didn't go for lunch or breakfast or dinner with anybody who was in business unless they promised to never talk about their company or business. Like, so I would go golfing with like a CEO, but we only talked about life. And so for three and a half months, I really ripped off the band aid and forced myself to decompress. That was a really healthy thing for me. So what I did in that period was I journaled. I did lifelines, I did mind maps, I made lists of every company that I'd ever run, every entrepreneurial venture I'd ever had, every project I'd ever led, every business area, what those business areas had done that had reported into me, all my failures, all my successes, all my lessons. I had about 57 lessons that I learned that I kind of documented, really internal lessons. And I came up with lists of things I loved and things I hated and things I sucked at and things I was great at. And what it kind of netted out at was I loved coaching, I love networking, I love speaking, I love helping entrepreneurs make their visions come true. Everything else I'm either really good at or okay at, but I don't love. And so I just decided to designed my world around that, decided to never run an operational company anymore. And I decided to work behind the scenes with CEOs. And I. So I called my first brand the Back Pocket coo, which was way before fractional roles existed. But I was basically a fractional coo. And I was a fractional COO for Karen Stewart from Calgary, who ran Fairway Divorce. In Vancouver. And I was a fractional COO for any Razor Solomon from Toronto who built iloverwards. Those three were my first coaching clients that behind the scenes, I helped them scale, build brands, put systems in place, and then that began, kind of what I do today. And now I have an organization that's exclusively for the coo, so no entrepreneurs are allowed to join. And then I run a community now called the COO alliance as a community to skill up the second in command for all these crazy entrepreneurs.
