When I look back at the past two months as the Writer in Residence at Toronto Public Library, with a focus on journalism, I can’t help but Joker smile like a silly silly man. Meeting with writers and running weekly programming has been so incredibly fulfilling and nourishing, it feels surreal. Like, did I just meet with 30 writers to advise them on their careers? Did I run six seminars, workshops and panels without any major issues? Yes, yes I did. And I’m incredibly proud of what I believe I accomplished: Helping writers get a head start in their journalism career, or level up their standing as a freelance journalist. I’ve been doing this ad hoc as a writing coach for the past six years but to be thrust into a two-month intensive program for consultations and evening events…it was a different story. And one that I enjoy telling myself over and over again. Giving writers the opportunity to learn from my experience is exactly why I became a coach in the first place. I want to let you know what I learned about myself in the past two months and then I’ll share what I learned about ambitious and inquisitive writers. The more you share, the more you grow There was a moment in the middle of consultation session with a young journalist when it dawned on me: I was maturing as both an educator and coach with this residency. Writers are asking me questions that I don’t often get with my lesson plans, such as how to write a book proposal for non-fiction, and by researching the answers to these questions prior to our meetings, I’m developing new skills, too. Maybe one day that research into book proposals will come in handy when I get writing a book of my own (it’s on the bucket list, folks!). When I was hosting a panel discussion on my final night of programming, I grew as a journalist. To hear editors from the Globe, the Star and Toronto Life share candidly what they look for in a pitch, that was invaluable to me, and the audience, I later found out. While I curated this event for attendees, I also learned several lessons on how to pitch successfully, proving once again you can never be too experienced to stop professionally developing. There are no stupid questions What I admired about the writers who wanted to consult with me was their openness. I was worried they would be shy or unsure of themselves. Maybe they’d bury a question among a lengthy bio on what they do for a living, or why they just got into writing. But everyone was candid and down-to-earth, displaying an eager appetite to gobble up whatever I served. To extend the food metaphor, I was happy to give folks a menu of answers that they could select. If someone asked me how to get started as a journalist, I had to ask them a few things first. What is motivating them to work in media? Is it for the revenue, the craft, the hobbyism of it all? Does feature reporting interest them or wold they prefer to write Op-Eds? Once I saw how these writers recognize how there are no stupid questions, I began to reflect on how I have been quiet in writer conferences and staged events where other raised hands extended high above inquiring heads. I can get like that, an extroverted introvert here, I like to say, so sometimes I have to find the courage to be confident about my own curiosity into the trade I know and love. If you ever wondered if you should apply for a writig residency, let me reply with a resounding YES! It’s the kind of work that gives back the more you put into it. And you can’t go wrong with being around books all day.  

Pound the rock. No risk it, no biscuit. If you follow the NFL, you’ve heard these terms before. And if you follow the Tampa Bay Bucs (like I have, since 1998), then you know these terms come from two of the team’s most formidable coaches, Jon Gruden and Bruce Arians. While I knew about these football strategies when I was watching the Bucs win their Super Bowls in 2003 and 2021, I got a refreshing history lesson on their origin stories when I checked out the new Amazon Prime series Raise the Flags. Tracking the 50-year history of the Bucs, this eight-episode series reminded me of how Gruden preached the “pound the rock” philosophy to inspire his team to win their first Super Bowl. It was enlightening because I was too young to truly understand his take on resilient football back then. But now, I see how it relates to improving myself as a solopreneur. The same goes with Arians’ approach to aggressive play-calling. Be relentless When Gruden was hired to coach the Bucs in 2002, they were a hot mess. Their offense was stagnant despite having a top-tier defense, and they couldn’t close games. They needed a change at the top and Gruden’s hard-nosed focus on grit was just what the Bucs needed. He needed a metaphor to revitalize this struggling team. “Pound the rock!” he demanded from his team. What that meant was grit, adaptability, and accountability. They used the running game to hit the defensive line relentlessly, ensuring their pass game would open up later. On the defensive side, Gruden wanted his all-stars (such as Warren Sapp and John Lynch) to use their strength to bully the other team. Don’t give them an easy down, Gruden said. It came down to this tagline after Gruden made “pound the rock” the slogan for his squad: “If you hit a rock with a hammer 99 times and nothing happens, the 100th blow might finally shatter it.” This idea instantly resonated with me as a freelance journalist and solopreneur. I might not be able to win over an editor with my first pitch. I might have to “pound the rock” and be relentless with finding the right story for that specific news network. I can’t give up when I get that first rejection; if I followed that path, I would have never written 60 articles for BBC News, which weren’t interested in my first three pitches. Also, I “pound the rock” with my marketing initiatives. My first 99 LinkedIn posts may not be as popular as I wanted them to be, or reach the right clientele, but that 100th post just might. I can’t give up simply because something isn’t working (the exception to the rule is when I feel it’s important to pivot away from a strategy that is proven fruitless, as opposed to sticking to something I feel we eventually score with readers). Buckling down and continuing to market yourself is the self-discipline we solopreneurs need to instill into our everyday processes. Great rewards come with great risk I can honestly say I’ve lived a generally conservative life. I’m no daredevil, I don’t leap out of my comfort zone very often, my social vibe could be described as “chill and laissez-faire, with a dash of weirdness.” I’ve always been fine with that characterization until it came time to take a hard look at my freelance writing business. If you’re in the same solopreneur boat as me, we can’t be risk-averse. We have to try some things that might not work at first but, heck, at least we gave it a shot. That’s what Arians told his Bucs team in the early 2020s when he helmed the infamous Tom Brady-led squad that eventually won the Super Bowl. His term, “No risk it, no biscuit,” essentially means you can’t live scared. You can’t be conservative in how you live life or play football. On the field, Arians wanted to ensure his quarterback had two primary reads: one that can pick up a first down (the safe “biscuit”) and one that could end in a touchdown (the “risk”). Arians wanted to see those explosive 20-plus-yard plays. He encouraged his QB to throw long on third down, even if the first-down market was a few yards away. It doesn’t come as a surprise to learn that during his time with the Cardinals and Buccaneers, his quarterbacks (like Carson Palmer, Jameis Winston, and Brady) consistently ranked at the top of the NFL in Average Depth of Target. How does this circle back to my solopreneur journey? I’ve taken more risks and will continue to do so, especially in the realm of client acquisition. I used to think I would only write for news outlets big and small but I decided to branch out with my content marketing programs and PR business, two branches that can be seen as an aggressive move for a long-standing journalist. The reward, the biscuit, has been scrumptious. My revenue has increased, word-of-mouth buzz has spread to other clients, and I feel more fulfilled as a solopreneur. I have interests in more than just covering the news, and I love working with brands I respect and admire. If I never risked it by venturing outside my cozy zone, my bank account would look a lot flatter now. We should all take more long shots. Apply for that grant you don’t think you’ll get. Email that big-time editor running that wildly popular magazine. Approach a source you thought would be off limits. Find a new revenue stream that is outside your circle of familiarity but could nourish you both mentally and financially. Be open to possibilities. If you want to learn more about how I’ve been helping solopreneurs improve their own approaches to running a sustainable business, contact me anytime.