If you tracked with the last few posts you might have noticed some hints that I’ve been on a long and (often unnecessarily) arduous road to where I am today. In 2010 I made the commitment to write and publish a book every year for a decade. I invested every penny I could into getting those books into the hands of readers. That would last for nine published books before I realized I was pushing myself to the breaking point to reach an arbitrary goal, and writing was not paying the bills.
About the time I finished my first book in South Africa, I decided to commit to posting a photo every day for as long as I could as a way of keeping people back in the States apprised to my adventures abroad. I hoped there would be a broader interest. I got to well over 4,000 photos posted without missing a day before finally accepting that no one really cared.
But in 2016, as I tried to figure out how to break through the noise, I thought I’d mark the 2,000th photo of the day by dropping my first daily vlog. I would go on to make just shy of 1,200 of those in a row. Conversely, this did end up becoming a job, though I still had a long way to go to make it sustainable (2025 Jay here shaking his head over 2018 Jay’s entire thought process).
The point is, I’ve been trying really hard to make some sort of headway in the creative space for a long time now. I’ve put in a lot of reps. It’s been really hard. There have been a lot, and I mean a lot of signals that maybe it’s not for me. Maybe I’m not good enough. Maybe no one cares.
But there were little signs that people did care. And deep down I believed that I did have something to offer. If I can’t figure out how to do so, that is the only way in which I truly fail. So I never gave up. And I will not give up.
It might take you less time, and you might be much smarter or better connected/resourced than I was. I hope that it’s not so painful for you in any case. But when it is painful, that’s just part of the game. And if you have something to give, take heart. Don’t stop. You’ve got this - which is key, because you’re the only one who can.
This is a special series for Jay’s 40th year. To receive all posts straight to your inbox, be sure to subscribe.







