Enough Playing It Safe

Introducing STILL GOING: Notes from a life in progress

Portrait of the artist, painting the artist, in progress…as ever.

My life vision, first consciously conceived at 12 years old, was to travel, be a writer and a rock star – and to have as much sex as possible. Now, at nearly 70, those pre-teen goals haven’t changed that much. They’ve been added to, such as “stay healthy” but basically, I am still pursuing – and have reached, to varying degrees – those goals.

OK, maybe not the “rock star” part, though I’ve certainly lived the rock ’n’ roll lifestyle, interviewed a lot of real ones, and even made a couple of my own albums. I once wanted to be “famous,” before that was the dream of every teen with an Instagram account, and Andy Warhol’s “15 minutes of fame” prediction came irritatingly true.

I’ve even had my fame, “local hero” division, as a high-profile newspaper columnist, and a radio “personality” for a season. But fame was always a crappy metric, so I’ve let that one go, along with the whole “rock star” thing.

Hell, “rock” itself isn’t even a thing any more. I’ve outlived even that.

This June I will turn 70, and while I’m none-too-happy about that milestone, it beats the alternative. So I can happily say that I have achieved my goals.

Now the question is, what do you do after your dreams come true?

I could rest on my laurels, and I do. Still, I hesitate to say I’m “retired” – though there’s a good bit of that in my days. Nevertheless, the urges to write, to create, and certainly, to travel – not to mention f@#k – have not left me. So now I, like any good actor, have to ask: “What’s my motivation?”

I recently got some motivation from an unexpected source: While visiting a couple of old friends in SoCal, I got an earful from one who doesn’t hold back in her opinions. She critiqued this Substack, saying that it was too much about me, or as certain old friends have long said, “it’s all about you.” I like to think that isn’t entirely true – there are a few countries and other people in there as well – but I took her point. (Her girlfriend noted, however, that she nevertheless reads all of my posts.)

Still, her comment resonated because I have felt my own dissatisfaction with this Substack for some time now. My last post, covering the last month of travel, skimmed over the surface so blithely that I wouldn’t blame anyone for wondering: Is that all there is? Is it just a lot of movement? Not that there’s anything wrong with that, exactly, but…at my age, shouldn’t there be something a bit more…substantial?

A writer whose Substack I follow, the marvelous generalist Ted Gioia, in The Honest Broker, posted just this morning about a writer I have long admired: Michel de Montaigne (1533-92). My reading of him has been relatively minimal, but of all the books I used to have – a whole library in my last real home – his is one of the few I have kept.

As Gioia wrote of the great essayist, “Montaigne only wanted to be himself, and help us see the world through his eyes – and he had confidence that this was just as valuable as any declaration from established authorities.” Given that Montaigne spent most of his life ensconced in the family castle – at a time when “established authorities” ran his world, totally – this was confidence, indeed.

It resonated with me, though Montaigne’s life and my own could hardly be more different. I’m not an aristocrat in a castle tower, but I’ve got options and a life that even an aristocrat like Montaigne couldn’t have imagined. I am not a tenth the writer Montaigne was. Nor am I terribly confident that the world needs my reflections. My credentials are modest.

But I am living consciously – maybe even a bit self-consciously – which means that I have been paying attention, living my life as close to my vision as I can, following my desires and dreams in ways that have cost myself (and to be honest, a few others) dearly, and I continue to pursue new adventures, even as I age into the last act of my life.

I created this life over several long, occasionally difficult decades. It didn’t just happen. And although I like to make it look easy, it wasn’t. And although I’ve had a long career as a newspaper and radio journalist, written books, recorded albums of my own songs, and even written and performed a one man show, my real achievement has been my life. It is the thing I am most proud of, and I love sharing it here.

That is, to the degree I do.

However, despite my friend’s critique of it being “all about me” – a phrase I’ve heard more than once from my nearest-and-dearest – for me, this Substack hasn’t been enough about me.

That is, this Substack has come to be a sort of extended postcard, full of exotic locales and a high-velocity life that has gradually become an overgrown Instagram post. Not that there’s anything wrong with that, but as a creator, I want it to be more.

More what has been the question.

I have considered writing more about all the wonderful people I meet, which would be completely legit. This Substack has been poorer for their absence, although they have certainly made my life richer. I just don’t feel as though it is my place to write anyone else’s life story. I am always aware of others’ privacy, and my journalistic training means that I can’t just flippantly write about someone else’s life or statements, and I always feel as though I have to do all the things the right journalistic way.

I don’t want to do that any more. I was a journalist for a long time, but am no longer, and I have no desire to return to that profession. Truth be told, me being a journalist was a bit of an accident; what I wanted was to be a writer who writes about whatever he likes, and a songwriter, and even a memoirist (my 2013 one man show, Underwater: The 100 Year Flood, was about my life, and my father’s death). So I split the difference by writing about my opinions of music for much of my career – for which I am grateful – but even that always felt a bit second-hand.

I wanted to be the creator, not the critic. I didn’t just want to write about others’ creations, others’ explorations of the depths of the self. I worry that my frustrated artist nature gave my criticism a hint of jealousy that I’m not proud of. In other words, I wanted to dive deeper – and I didn’t.

I still don’t dig so deep, at least not on this Substack, which is ostensibly about my life, but mostly skims the surface, eager to entertain, and to a lesser degree, to impress. But it doesn’t do what good creators do, what good artists do; it doesn’t dig down into life, into the things that have shaped mine, and thus – the memoirist hopes – might help the reader understand their own life, and self, a bit more.

Is this ego? Is this even possible? Well, yes and yes. The ego part – the fear of making it “all about me,” or of appearing a “narcissist” (a word that has been flung in my direction by those who should know better) – has kept me from stating my truth, even as I have lived it aggressively.

I’ve just kept most of the juicy bits, let alone the parts that might shock or offend, hidden. Lots of hiding here, which I have to admit is a theme in my life. Despite my inclination to take chances, to travel broadly, I have kept many of the deeper, maybe darker, aspects of my life out of public view. I have played it safe. And good artists don’t do that.

I want to be a good artist.

I know music well, from both sides now, I know travel well, and I know a lot of people well. I wouldn’t want to have lived without any of them. (OK, I could have done without a few.) But what I know best is my own life, which, to be frank, is more interesting to me than anything else. I don’t think I’m unusual in that. Certainly not among artists!

I’ve worked at making it interesting, to myself, and perhaps, by extension, to others. And some of the most interesting things I didn’t work at at all, but interesting things befell me. (OK, I could have done without a few of those, too.)

But if I don’t put the real thing out there, how do I know that it actually is interesting? How do I know that I have learned anything, let alone offered anyone else the chance? More importantly, how can I know that this life, lived through all manner of (largely hidden) storm and stress, is going to have any impact beyond “nice life, Dave”? If I never put it out there, I’ll never know.

And time is running out. Really. The end is far, far closer than the beginning. I can feel it in my bones. I see it in my friends.

I have learned a thing or two in that time, and perhaps some of what I’ve learned could be useful, especially to those younger than I am (which is, at this point, nearly everyone). Maybe I can, with some reflection, write something that could inspire, as well as inform and entertain.

I have come to the conclusion that sharing is at least worth a try, that someone could learn from my many mistakes, or be inspired by some of my successes. Or be inspired by my mistakes, some of which have been truly spectacular, or at least amusing. In retrospect.

This is not all magnanimity on my part; I am kinda bored by merely reciting a list of places I’ve visited, which is perhaps why it took me a month to get around even to catching you up a couple of weeks ago. I’ve always written long postcards, and long Substacks, but of what use is any of that if it’s all length and no depth? (Ahem.)

How can I still, as a writer as well as a man, grow? Is it too late for me? Is there any point? What does being an (almost!) 70-year-old writer look like these days? What does being this old, and living like a 22-year-old – or a 12-year-old’s dream – look like? What does this 70-year-old writer look like – look at – in 2026?

These are some of the things that I’ve been thinking about as I wander. These are the thoughts that have stopped me writing much lately. I don’t want to impress you so much any more; I want to inspire you. I want you to look at my life and not (just) be entertained; and I certainly don’t want you to be jealous.

I want you to be encouraged. If I can do it, you can too. If I can survive that, then you can, too. Perhaps I have earned the credibility – and a portion of Montaigne’s confidence – to at least offer it.

Or maybe not: Just writing this feels like jumping off a cliff into the unknown; it’s scary. The voices that want to keep me safe are shouting: “Don’t give ‘em any ammunition!” “You could be setting yourself up for humiliation!” And especially, “Who do you think you are?”

But sod it, as my Anglo friends say. I’ve jumped off cliffs before, whether it was getting married, or coming out, or getting on a stage, or moving to New York, or Berlin, or Saigon – and I’ve survived. Or better.

You can, too.

So…that’s where I want to go now. I barely know what it means. The fact that it scares me almost guarantees that it’s worth doing. Fingers crossed.

I hope you want to come with me. I will still write about my travels, probably more often in a revived Weekend Confidential, but in the main posts, I plan to go deeper.

So, here comes Still Going: Notes from a life in progress. How it will develop is anyone’s guess.

Just don’t expect Montaigne!

Onward.