Fresh from being named best sports journalist at the Voyager media awards, Dylan Cleaver reflects on a year out on his own.
This story first appeared on The Bounce, a Substack newsletter by Dylan Cleaver.
One year and one day ago a personal essay appeared on The Spinoff titled Why I left traditional sports journalism behind to start a newsletter about sports. Simultaneously, on the Substack platform, the same essay appeared under the headline, Some breaking news I want to share with you: Introducing The Bounce, a newsletter on sport, the business of sport and other things loosely related to sport.
For much of the previous 25 years, I had written stories, filed them, forgotten them and moved on to the next. This one, I had no choice but to stick around and wait for a reaction. I had a new email address and if my inbox wasn’t being exercised, then I was in a bit of trouble.
It was exciting, but also terrifying. That fear was encapsulated in this paragraph from the introductory essay: “Even the seemingly simple task of writing a ‘welcome note’ has been an energising exercise. Also a slightly discomfiting one – as a salaried man for so long, it’s a little weird asking for your money, your private equity if you will.”
The discomfiture has never really left. I still feel awkward about including a donation button in my newsletters but I have to remind myself that this is it, this is how I have chosen to make my living. And my much valued subscribers support that decision and I hope will continue to do so.
Apparently one of the most common recurring nightmares, even after leaving school, is turning up to class and discovering you forgot to put pants on. Charlatans and psychologists alike have made money trying to interpret that dream but my recurring nightmare in the lead-up to September 6, 2021, didn’t require any deep analysis.
What if nobody subscribes?
That would be my naked-in-class moment.
So when my inbox started “pinging” that morning it was an enormous sense of relief and that evening I sat at my desk and enjoyed a beer.
It was also, as I would learn, deceptive. The relief almost instantly circles back to fear. It just goes by a different name: responsibility.
Now that people are paying me, I have to deliver, and what exactly does delivery look like? How often? How long? What time? What topics?
Sure, there was a long-term vision statement in that opening essay, but how do I actually go about making the following paragraphs something more than delusions of grandeur.
“I’m attracted to the idea that The Bounce is no one thing. There will be opinion, there will be critical analysis both fervent and sober, there will be narratives and features, profiles and oral histories. There will be reviews, listicles and links to some of the best sports journalism from around the globe. There will be reportage from on the ground. I will get to cricket tests, to rugby tests, and to a bunch of other stuff.
“In the future I’d love to explore The Bounce: Podcast; I see live chats and panel discussions. What I’d really love, however, would be for The Bounce to evolve into a platform for emerging voices and some of my favourite sports thinkers and writers.”
I look back at those paragraphs now and alternatively grin and blench. I’ve kept my word on some things (opinion, links, reviews, independence, why-the-hell-did-I-push-publish…), dipped infrequently into others (narratives/ features/ profiles, provide a platform for other writers, listicles) and failed in others (oral histories, The Bounce podcast, emerging writers, reportage from the ground).
In fact, one of the key lessons from this first year has been not to promise the moon if you haven’t built a launchpad. It’s not the only lesson or, for the high-performance sports community, learning. Here are some others, in no particular order.
- Setting up a sports “generalist” newsletter was ambitious. The most common form of negative feedback is along the lines of, “not enough [fill in your favourite sport]”. I can’t get angry at this because it’s how humans work. We want more of what we like and less of what we’re not interested in, so if league, basketball, netball or athletics is your thing – and they are very fine things – you’re at best only mildly interested in an appraisal of Tom Latham’s really, really weird test career. Sometimes I wonder if I should have marked my particular sporting obsessions more clearly on the box.
- Writing a specialist cricket or rugby newsletter would drive me mad, however, because although they’re the sports I’m habitually drawn to watch, most sports and the rich stories within them fascinate me. Not UFC though, can’t stand it.
- I should have worked harder to establish a social media presence before embarking on a newsletter. It is the most effective way of sharing, but there’s also a part of me that thinks if I spent too long on social media I would by now have abandoned this dystopia and decamped to a cave near the mouth of the Tongapōrutu River where I’d spend my nights replaying the 1992 Cricket World Cup semifinal in my head.
- While I love the autonomy, you really know you’re on your own when a Friday evening email with “I reserve all rights” lands with a thud. While that potential legal crisis was nipped in the bud, it did press home the idea that occasionally another set of eyes would be handy.
- I also feel this way when I read back over my mistakes and clunky syntax. No matter how diligent you tell yourself you’ll be, there are times when you have to push publish before you’ve fine-tooth-combed a piece and it always comes back to bite. Sometimes even when you’ve given yourself a full half hour to edit, errors slip through. Sorry.
- Understand how tax works before starting out on your own.
- People love reading when the All Blacks lose.
- You’d be amazed how quickly a year can come around when you’re having fun.
The biggest lesson of all is something deeper and a little harder to articulate without sounding like a cereal-box careers adviser, but I’ll give it a go.
Sometimes you have to take a leap into the unknown. I understand the egotism in that; not everybody is in a position to leave a job for an uncertain future and not everyone is provided the softest of soft landings as I was by the Substack Pro programme (from a purely financial perspective, my step into the unknown starts today).
But freaking yourself out can have rewards that won’t show up on anybody’s GST returns.
When I started in the media last century, I made a promise to myself that I wouldn’t hang around too long in one place. Five years was the arbitrary target I set myself. I’d noticed early on that newsroom recalcitrants and malcontents tended to be the ones who had been there the longest. I swore I wasn’t going to be that guy until all of a sudden, 17 years into my five-year stint at the Herald, I had become that guy.
Some of the big issues facing sports journalism bothered the hell out of me, but so did the little, petty things. A byline being dropped off here or a story not running there was a sign the world was against me rather than just a mundane fact of newsroom life.
I needed an environment where I couldn’t blame others; an environment to rediscover my passion for sportswriting. The Bounce did that much quicker than I could anticipate and I hope it remains a big part of what I do for a long time yet.
I suspect it’s going to be easier to get to live sport – out damned Covid – but I don’t know quite how I’ll get there.
I don’t know whether I will get bulk “unsubscribes” over the next couple of days as the annual renewals for the early adopters come up.
I do know that I still get a buzz and am incredibly grateful every time “New paid subscription for The Bounce” pops up in my alerts. If that was you, I felt like giving you a hug, but it’s probably better for everyone that you got an auto-generated reply instead.
There’s still so much I want to do. There’s still so much I said I’d do!
I’d love readers to stick around for another year to see if I manage to squeeze out an oral history of something, anything.
As for now, I was going to leave with the same two words I left with 366 days ago – “stay tuned” – but at the last minute I thought of a better sign-off.
Thanks.