Think of my ongoing exchanges with artist Thomas Campbell about how years of patient, thoughtful creative endeavour led him to his opus Yi-Wo:

Or last year’s chat with director Lucy Walker about how she developed the multi-award-winning Mountain Queen:

Then there’s my discussion with about his decades-long quest to bring his recent novel American Tiger to life:

And that’s just in the last year.

To this list, you can add my recent live Kendal Mountain Festival conversation with Oscar-winning filmmaker Orlando von Einsiedel.

On paper, Orlando’s remarkable career represents the summit of modern documentary filmmaking.

With Virunga, The White Helmets, The Lost Children, and his forthcoming The Cycle of Love, Orlando’s films have shaped the visual and emotional language of contemporary non-fiction storytelling in ways that will resonate for years.

And from the outside, this looks like the creative promised land. Surely Orlando is now in a position to name his price and call his own creative shots?

What emerged from our conversation, instead, was yet another pitiless reminder of what it actually takes to sustain a creative career. Even when you’ve got an Oscar on the CV.

Here are my key creative lessons from this vital conversation…

Insights is the Looking Sideways section, exclusively for my paid subscribing community.

It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been making a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

• How can I spend more time doing the things I’m passionate about?

• What does a ‘successful’ creative life actually look like?

Here are a few recent Insights articles to whet your appetite:

1. Creative careers are never secure - even if you’ve won an Oscar

The simple, sobering reality that uncertainty never disappears, no matter what level of ‘success’ you attain, was perhaps the most important lesson of the entire conversation.

Read more

Over the last three years, I’ve been lucky enough to work closely with this week’s guest contributor Bronwen Foster-Butler; both through my work at All Conditions Media (Finisterre are one of our clients), and through some of the recent talks on marketing and activism I’ve been hosting at events like MADFest (above) and Kendal’s Outdoor Connections (below)

And during that time, I’ve learned a few key things about Bronwen.

Firstly, she doesn’t take this whole thing too seriously; a very important quality in an industry full of self-important, self-aggrandising Kool Aid drinkers.

Secondly, and perhaps most crucially, she’s incredibly good at her job. This might seem like a rather obvious point. But as you learn when you’ve worked with brands and marketing and PR types as long as I have, it is actually pretty rare.

(I wrote an entire piece about outdoor industry’s tendency to engage in vapid, uninspiring groupthink a couple of years ago, which you can read below:)

Thirdly - and related to the above point - Bronwen understands that any successful career, in any field, has a few universal elements in common.

Which is what she goes into today, and the piece you’re about to read contains some illuminating lessons from her time working with Finisterre, lululemon, Burberry and PANGAIA.

Hopefully, you can take these learnings and apply them to your own creative and work situations.

Insights is the Looking Sideways section, exclusively for my paid subscribing community.

It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been making a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

• How can I spend more time doing the things I’m passionate about?

• What does a ‘successful’ creative life actually look like?

Here are a few recent Insights articles to whet your appetite:

This week only - get full Insights access for only £32. It’s usually £65! Hit the button below….

Redeem here!

Before we get started, here’s how I got here. My first job was in the boot room of the rental shop at my local ski hill, Snow Valley, in Barrie, Ontario.

If you ask me, there is nowhere more exciting in a ski resort than a boot room. Why? Because the majority of people in there are about to try skiing or snowboarding for the very first time. And at Snow Valley, we had a LOT of beginners, thanks to the resort’s famous Discover Skiing and Snowboarding programmes. At one point, the resort boasted the biggest ski school in Canada, despite only having a vert of 85m and three chairlifts.

This experience taught me to appreciate being a beginner, and to respect anyone trying something for the very first time.

From the boot room, I eventually became a CASI Level 2 snowboard instructor, coaching at Whistler-Blackcomb, teaching with Roxy Freestyle women’s only camps, and volunteering with the Burton Chill programme.

At some point, I moved to the UK and spent over 21 years living and working in London. My marketing career began in ad-land, at JWT, the world’s first ad agency, before I moved client side with Burberry. I was Lululemon’s first European brand hire, and then helped build the material science brand PANGAIA.

I had a short stint at a beautiful yet flawed Russian brand called Voylok (we launched 10 days before Russia invaded Ukraine - now there was a harsh lesson in branding!), before finally landing at Finisterre, where I’ve been for the past three-and-a-half years. I now live full time in Devon with my family.

I’m still learning so much each day that it’s difficult to list out the things I’ve learned up to now. If you ask me next week, this list is likely to change. But for now, here are the six things I’ve learned along the way.

1. Don’t let your job become your identity

When I first joined Lululemon, I remember a few people saying, “You were born for this job”.

Well, I think I took that to heart. At Lululemon, we had a brand muse called Ocean, and my life so closely followed hers that I thought it gave me licence to treat the brand like it was my own. At the same time, and far more dangerously, I allowed myself to become the brand. For years, I felt I WAS the brand.

What did this look like in practice? When decisions were made at senior levels about the brand, I would take them personally. And when the time came for me to finally cut the cord leave, I felt as though I was leaving a part of my own identity behind.

“This is something I see a lot in outdoor and lifestyle brands. When the product is part of an activity or hobby you especially love, it’s all too easy to let the job become your identity, and to let your own sense of self-worth get caught up in this, too”.

In recent years, I’ve learned a lot from my Gen Z colleagues, but perhaps nothing more so than the importance of having boundaries. I love the work I do with Finisterre, and I love the brand. But at the same time, I’m still myself. I’m a terrible surfer, a proud Devon dweller (yes, I put the cream on first), and a sucker for pop culture, which means memes are my love language.

2. ‘Having it all’ isn’t a destination and means something different to everybody.

I think this is especially relevant to working mums, who are still essentially told that we simply cannot ‘have it all’. Or that ‘having it all’ means attempting to have a meaningful and rewarding career while also being a mother as defined by archaic standards.

This was something I really struggled with when I became a mother for the first time, because the societal archetype of the ‘Great Mum’ did not match up to my own experience or the way I wanted to live my life.

“This began before I even went on maternity leave, when I was told that I’d have to choose between a promotion and becoming a mother. And when I had the audacity to cut my maternity leave short and return to work early, there were plenty of opinions floated my way about how I was sacrificing my children’s well-being by putting my career first”.

Here’s the rub: I am a better mother because of my job. I’m also better at my job because I’m a mother.

For me, ‘having it all’ isn’t a destination. It’s about balancing my life each and every day.

3. Leadership isn’t about perfection

Early in my career, I thought that great leadership was something that I would attain, and it would be smooth going from that point. I’d have it nailed and then my own work could finish whilst I fearlessly led others forward.

Instead, what I’ve learned time and time again is that leadership isn’t something you ‘get’ once. It’s a daily practice. It’s about learning, unlearning, listening, experimenting, and then listening some more.

Every single day I think about what kind of leader I want to be, and I don’t always get it right.

“True leadership is knowing when you’ve fucked up and then figuring out how to go back and fix it: whether that’s a bad decision, a relationship, or trust”.

The leaders who inspire me the most are the ones who have got it wrong more than right, but who have cleaned up their messes along the way.

4. Allow others to contribute to your success

As a Leo, third-child, type-A personality AND millennial, I spent the first half of my career/life caring far too much about my own personal success and what others thought about me, and not nearly enough time asking myself what I could learn from others.

“What changed this picture? A great manager told me that I needed to stop being afraid of letting others contribute to my success – and that I would be far more successful if I did so”.

What this means for me in practice is understanding how to enrol others so that they are as excited and passionate about a project as I am.

It’s about stopping and listening – taking on other people’s opinions, thoughts, ideas, and experiences, and allowing them to make something even richer. Above all, it’s about recognising that my team’s success is my success.

5. As a leader, your job is to have the questions, not the answers

Related: for a long time, I thought that being in a senior position meant that I should be the one with all the answers.

That was until another great leader (the wonderful Duke Stump) taught me a simple lesson: that a leader’s job is to create the conditions for their team to thrive. Nothing else. What does this mean in practice? That you should be the person with the questions, not the answers.

It takes a lot of confidence to pull this off, and I still find myself stumbling into the all-too-easy trap of giving my team the answer rather than posing the questions.

But then I try again, and remind myself that asking the right questions will get a far better answer, each and every time.

Bonus! Know when to leave

No job has a set timeframe. Which is why you need to understand when it is time to move on. If you’re bored, and find you can do your job with your eyes closed, it’s time to move on. Yes - even if you love the brand or company!

In my case, I’ve found that staying too long can have profoundly negative impacts, whether that’s entitlement or discontent; or, in the worst case, toxicity and poor health.

“I’ve stayed too long in two of my jobs. In the first instance, I spent the last year in my role feeling frustrated and underappreciated. In the second instance, it meant that I ended up on medication and in therapy”.

Your body will tell you when you’re done – listen to it.

Enjoy the Insights piece? Anything resonate? Let me know using the button below!

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Reading regularly continues to be important for my mental health, especially when it comes to winning a few small victories in the ongoing battle against digital distraction. And it was a pretty good reading year, thanks to some great books and two long-ish trips away, during which I deleted all social apps, and made sure I had some good books to hand.

As ever, I kept a record of everything I read in 2025 in a regularly updated reading list, which you can see here. Inspired by reader/subscriber Tim LeRoy, I also began a Looking Sideways book store.

Buy anything from here and you’ll be supporting independent UK book stores (ie not paying for Jeff Bezos’ next rocket), as well as helping finance Looking Sideways (I get a 10% commission) in a really simple way. Win/win, right?

As is now a Looking Sideways tradition, I’m ending the year by sharing the five books I’ve enjoyed the most.

Want to discuss any of my selections, or share any of your own 2025 reads? Click here or let me know in the comments:

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1. Mayflies, by Andrew O’Hagan

One of the things I am really enjoying about getting old is how much your long-term friendships deepen and take on new dimensions.

And I get older, I realise that the friendships I formed in my teens were an attempt to create a surrogate family after the demise of my actual one.

It’s one reason why I have always taken friendship so seriously, and do what I can to support and be loyal to my friends.

And it’s why I think I enjoyed Mayflies so much. It is an elegant, elegiac treatise on the peculiarities of male friendship, and our blokey reluctance to deal with our own mortality, which made me reflect deeply on how I view these topics. And if that isn’t the job of art, I don’t know what is.

Buy it here.

2. Stoner, by John Williams

“There are wars and defeats and victories of the human race that are not military and that are not recorded in the annals of history”.

I loved Butcher’s Crossing and Augustus, the other John Williams books I’ve read, but this beautiful paean to an ordinary life completely floored me.

I’m sure anybody else who’s read it will understand what I mean. Who’s out there?

More here.

3. Death of an Ordinary Man, by Sarah Perry

“He was in some ways a very ordinary man, but as he began to die, it became clear how extraordinary he was”.

Another thing about getting older: the unavoidable realities that are death and sickness.

In our society in particular we appear to be uniquely, historically unwilling to acknowledge these mundane inevitabilities. Which is one reason why I loved Sarah Perry’s new book, a remarkable and very moving examination of the death of her father-in-law.

As with everything Sarah Perry writes, there’s a liturgical, deeply compassionate note to this devastating book that reminded me, in this case, of CS Lewis or Montaigne. It’s that good.

More here.

4. I Am Dynamite! by Sue Prideaux

I really didn’t expect this biography of German philosopher Freidrich Nietzsche to be so beautifully written and riotously entertaining.

It’s also a welcome and frequently hilarious reminder that even greats like Nietzsche were basically petty creative egomanics; constantly worrying about why their friends hadn’t fed back on their latest work, how on earth they were going to raise money for their next project, and why nobody would review their book, and so on.

I enjoyed it so much I wrote this really lengthy blog about it, which you can read here:

More here

5. Fire Weather, by John Vaillant

John Vaillant’s account of the Fort McMurray fire is the best book I’ve ever read about our chronic addiction to fossil fuels, the way that this has shaped our recent history, and the devastating havoc this voracious behaviour has wreaked on the environment.

It’s the perfect companion piece to Lucy Walker’s Bring Your Own Brigade, which we discussed at length in our episode 248 conversation earlier this year.

More here.

Read something I should add to my 2025 list? Any books you particularly enjoyed this year that you’d like to share? Just want to geek out on reading and books with other members of the Looking Sideways community? You know what to do….

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As regulars will know, I’m on a mission to help my Insights paid subscribers find their own answers to two fundamental questions:

How can I spend more time doing the things I’m passionate about?

What does a ‘successful’ creative career really look like?

That was the thinking behind my three-part series on the reality of earning money as a freelance creative.

If you missed this the first time around, catch up below:

As this and subsequent series were so popular, I’m back with another two-parter discussing the reality of how freelancers - in this case film-makers - actually earn a living.

Last week, we heard from film-maker and internet sensation Johno Verity, and Ellie Green of Summit Fever Media, on the reality of their freelance lives as film-makers. Catch up with this one here:

Now, this week, I’m chatting to Rebecca Coley, director of the brilliant Point of Change documentary, and fast-rising surf photographer and film-maker Samuel Howard.

Read on and, as ever, let me know what you think in the comments below

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1. Rebecca Coley

What do you say when people ask you what you do for a living?

Usually, I say I am a filmmaker. If they’re interested and I have time, I explain more, but it is easiest to say that for starters. People usually say, “Anything I’ve seen”, and then I feel like I’m rubbish! Lol. So I sometimes want to avoid getting into it as I am a director and I make films, but I also do lots of other things too...

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As regulars will know, I’m on a mission to help my Insights paid subscribers find their own answers to two fundamental questions:

How can I spend more time doing the things I’m passionate about?

What does a ‘successful’ creative career really look like?

That was the thinking behind my three-part series on the reality of earning money as a freelance creative.

If you missed this the first time around, catch up below:

As this and subsequent series were so popular, I’m back with another two-parter discussing the reality of how freelancers - in this case film-makers - actually earn a living.

Beyond the paid subscriber jump: read on for this latest instalment with Johno Verity and Ellie Green of Summit Fever Media.

Subscribe now

1. Johno Verity

What do you say when people ask you what you do for a living?

DP, Director of Photography. Sometimes this makes me cringe, as I think it sounds a bit grandiose, although I think that’s what I am. I also make money from my social media channels. Does this make me an influencer?

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I go back a long, long way with this week’s guest contributor Jon Weaver.

He’a a dear friend, and also one of the few absolutely trusted people I go to for advice about my own career and creative pursuits.

Maybe it’s because I think there are a lot of parallels in the way we’ve approached our own careers, both of which have been varied and, to put it mildly, multi-faceted. (Incidentally, I believe this is the reality of most creative careers, especially in our industry)

But I also think it’s because we share the view that ‘creativity’ is about problem-solving, and it can ultimately mean whatever you want it to.

And that’s one of the things I’ve always admired about Jon. Whatever situation he’s in, he’s found a way of turning it to his advantage so he can continue to follow his creative interests and instincts.

Sure, this has led him to independent creative endeavours such as his Anti-Blueprint Project books, or his brilliant Substack, in which he analyses brands and marketing campaigns.

But it’s also mainly evident in the work he and his teams produce under his leadership and direction. Look at Db’s recent creative ad campaigns, for example. Or the Pack Heavy Chase Light book, above.

Or the Db Fund, a project I’ve collaborated with Jon on for the past four years.

This is also the reality of the creative life for most of us: we have to carve out of own opportunities for creative expression based upon the circumstances at hand. The workplace is an absolutely key part of that.

It’s why I enjoy the continuing intellectual challenge of running my agency All Conditions Media; fundamentally, as I have said elsewhere, I see this as a creative process as much as it is an entrepreneurial one.

As you’ll see when you read this piece, such creative pragmatism has also been the foundation of Jon’s career. As such, the learnings he shares here are so pertinent to anybody looking to make the most of their current situation, or find fulfilment in their own working life.

This ‘creativity is where you find it’ ethos is at the heart of Jon’s career, and is what I asked him to explore in this Insights piece.

Insights is the Looking Sideways section, exclusively for my paid subscribing community.

It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been pissing about for a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

• How can I spend more time doing the things I’m passionate about?

• What does a ‘successful’ creative life actually look like?

Here are a few recent Insights articles to whet your appetite:

Matt asked me to write this piece and it instantly got me thinking back over the last 20 years - what I wish I’d known earlier, and what things I need to constantly remind myself about.

To set the stage: I currently work with Db leading the marketing team. Before this, I worked at Nike on the brand side across football, the womens’ category, training, and snowboarding. My career proper started even earlier, at Burton Snowboards in Innsbruck.

Along the way, I've always had things going on the side: writing for Whitelines for Matt, making videos, writing my book The Anti-Blueprint Project, building drinks brand ūmmi Kombucha with some friends, and now writing a Substack exploring how brands grow.

Here are five things I’ve learned during that time. I hope you find them useful!

1. Learn to speak in public

Now that I have kids, I try to show them that there's nothing to fear when it comes to speaking in front of others. It's one of the greatest career accelerators I know - especially once you're in a large or growing company. The ability to convey your ideas clearly, and to get others to believe in what you're saying, is a huge advantage.

It's the same in sport: the great managers in football are usually the ones who can get others to believe in their ideas. So start as soon as you can, get comfortable with it, and keep honing the skill.

And while we're on it: keep learning in general. Keep thinking about what skills you could pick up or master. Last year I took on our digital business for a few months, and I'll happily admit I was a total rookie in that regard.

But I loved learning all about digital marketing - something that wasn't even around when I was at university.

Damn, I sound old.

2. Figure out how you work best and create your schedule around that

One thing I only realised about five years ago is that I work really well from around 5:30am–8am: before the house wakes up, before people start texting and calling, and before I start overthinking.

I find this time incredibly valuable. I'll usually try to get an hour or so of work done then, and I'm always surprised at what I can achieve in that focused hour versus a whole interrupted day.

The challenge - especially if you're required to work strict office hours - is finding a way to build a schedule that allows for this flexibility.

But with good communication, you can do it, as most people prefer productive teammates over people who are just ‘there’.

3. You work for a boss, not a company

It sounds like a cliché. But if you have a boss that cares, that stage of your career will feel way more rewarding- and chances are, more successful - because they're invested in getting the best out of you.

Sure, the company name looks great on the résumé. But for personal growth, it's always about the person you work for.

That usually means someone who is not trying to prove too much, who is comfortable in themselves, who knows what's going on behind the scenes in your life and, importantly, will give you a chance.

I've been lucky enough to work for a couple of amazing bosses. One in particular stands out - she was the person who gave us the news that Nike was shutting down the snowboarding department, which at the time was obviously devastating.

It would have been easy to resent her for that, but I can tell you: all the people affected by that move would still have run through a brick wall for her the next day, such was our admiration for her leadership style.

4. Focus on a couple of things

At any company, there's always a lot going on: fires to put out, drama to deal with, actual work that needs shipping.

Ultimately, you need to prioritise what makes a difference for you and the company. An exercise I’ve found useful in this regard (and what I often say to people who are struggling) is to ask myself the following question: how much of what is occupying your day would make your CV?

I’m willing to bet: not much. So think about the one or two things you’d put on your CV or LinkedIn in five years time, and own those things. Make them the most successful thing you do.

I had a period at Nike where I really struggled with this. Every year my feedback basically said ‘He’s a really nice guy, always helping everyone’ - which is code for ‘he needs to own something’.

Two things helped me shift:

a) I read Essentialism by Greg McKeown, which contains an amazing piece of advice. If you keep getting asked to take on more projects and you've hit capacity; the next time your boss asks, you say: "Yes, of course I can help - which of my other eight priorities should I drop to make space for this?"

That was a lightbulb moment for me. Now, I always prefer someone to help me think in terms of priorities instead of just letting projects slip. That's something I tell my team today.

b) I searched for an unloved category at Nike to own. That ended up, quite randomly, being sports bras and tights.

For a couple of years I could tell you more about bra support levels (depending on the workout) than anyone else on the brand team.

At one point we were doing insights work and I even brought in Joe Carlino (who made the snowboard movie Never Not for Nike) to help out, which was a fun full-circle moment.

But most importantly, it gave me a project I could own and push forward, which was hugely beneficial to my career in the long run.

5. Create momentum—and make your boss look good from it

Think about a football team going through a tough patch. Sometimes commentators say: "Just stop the bleeding." Tighten the defence, then start scoring.

I find the same applies to marketing: get a couple of small wins under your belt, share them with your team, and let momentum build. Momentum breeds momentum. Before you know it, you're achieving big things.

People often think brands or companies need to make massive splashes. Yes, sometimes you do. But it's like basketball: everyone remembers Michael Jordan's game-winning shots; but they forget the other 32 points he scored that night to give the Bulls the chance to win in the first place.

Building a successful work environment for you and your peers is about stacking wins and building momentum - or creating ‘a snowball effect’, as I call it on my Substack - until the whole thing is flying downhill with unstoppable velocity.

As you get wins, as you hold events, as you deliver results; keep information flowing to your boss. It could be a weekly recap email, or a monthly update at an All-Hands. It might feel like boasting, but most of us forget to mention the everyday things that actually matter.

And remember: your boss has a boss too, so make their life easier by giving them good stories to share upwards. A quick story: we once did an event in London with Phil Young - epic training, great vibe. Afterward, everyone went to the pub. Around 1am, Joe Carlino sent over a three-minute event recap he'd already edited together. The whole pub went nuts watching it.

That's how you build momentum and keep the energy alive. Whatever format you choose - weekly update, monthly recap - set a rhythm and stick to it.

Bonus! Earn a job, don't apply for a job

Often I see people spending their time complaining. Why they don't I have a certain role? Why aren't I getting paid more? If you let them, they'll drain hours of your day with this talk. So you can only imagine how full of this their own days are.

But the reality I've found is this: the best way to get a new role - or earn a promotion - is to step up and take on new tasks outside your usual remit so that people see you as the person who owns that thing.

As an example: when I started at Burton, I was an intern for 9 months, maybe even a year, on €600 a month. Was it fairly paid? No. Was it a great way to get my foot in the door and earn experience? 100% yes. I turned that role into the European Marketing Manager position by organising a few events, managing some team stuff, and building it into something much bigger.

I've had similar experiences at Db. Before I was CMO, I had already taken on the responsibility of leading the marketing team. Not in terms of title or pay - I just stepped in because we saw a gap, and a chance to help the business move forward by moving the current marketing lead into a more strategic role, and then I had an opportunity to prove I could lead.

I know these days there's more of a culture around demanding what you feel you deserve - and yes, everyone should fight for their package. But I'd always rather work with someone who's picking up slack and owning things, rather than with someone who's spending their energy complaining.

At the end of the day, every boss has too much on their plate. Ask them: "Where do you need help? What information, recaps, decks, research do you need?"

Chances are, there's something they want to get to but don't have the bandwidth. That's where you can step in.

I hope you found this useful! My DMs are always open on Substack, LinkedIn or Instagram if you have specific questions.

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If you’re new here - welcome! I appear to have picked up a lot of new subscribers during my brief summer hiatus. If you’re wondering what all this is about, Looking Sideways is where I examine the creative life through the lens of surfing, skateboarding, snowboarding and other related endeavours.

Looking Sidewa…

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Halfway through the reading year, I thought I’d share the five books I’ve enjoyed the most this year - a couple of novels, a biography, and an instant none-fiction classic among them.

Make sure you tell me what you’ve been reading this year in the comments….

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With my 250th episode of Looking Sideways on the horizon, and a rather large Substack milestone also looming, I’m sharing some classic old episodes and blogs from the archive, continuing with this piece on the art of interviewing, which I first published in February 2021.

I’ve taken the Insights paywall o…

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I have my 250th episode of Looking Sideways coming up! And I’m also very close to hitting a rather large Substack subscriber milestone, which itself feels like a nicely significant moment.

I’m celebrating these numbers because they’re the result of me turning up for this thing …

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As regulars will know, I’m on a mission to help my Insights paid subscribers find their own answers to two fundamental questions:

How can I spend more time doing the things I’m passionate about?

What does a ‘successful’ creative career really look like?

That was the thinking behind my three-part series on the reality of earning money as a freelance creative.

If you missed this the first time around, catch up below:

As this series was so popular, I’m back with another two-parter discussing the reality of how freelancers - in this case photographers - actually earn a living.

Catch up on the first part with Chris Burkard, Bella Rose Bunce, James Bowdon and Hannah Bailey below….

…and beyond the paid subscriber jump: read on for the latest instalment with Christa Funk, Nathan Gallagher, Bethany Mercer and James North, as well as my own thoughts on how AI will potentially impact creative careers such as photography, journalism and film-making - and how we should think about it.

Subscribe now

It’s amazing how quickly the creative and freelance landscapes have changed since I began this series last summer, and especially in the six short months since I posted the last instalment in December 2024.

Back then, I wrote:

“Photographers are in a particularly interesting position these days. Gone are those pre-digital days, when analogue syndication meant photographers could establish a niche for themselves while also making some proper cash.

The advent of digital scuppered that business model for all but those at the very top of the food chain”.

Since then, as we doubtless all recognise, the picture has changed even dramatically: thanks to the cultural, economic and geopolitical impact of events in America; and the insanely fast-paced encroachment of AI onto every aspect of the creative working life.

As Joe White put it in last week’s Insights post about commissioning creative work as a marketing manager:

“Budgets are shrinking, and AI is supposedly about to steal your lunch (though I’m not convinced). The mood is understandably pessimistic”.

Of course, as is the case with any technological advance on this scale, at this point it’s basically impossible to predict where we will end up.

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It’s only April, but I think I might already have a contender for my book of the year: I Am Dynamite!, Sue Prideaux’s fantastically-entertaining biography of German philosopher Friedrich Nietzsche

I stumbled across it via the always-excellent Five Books newsletter, which made a passing reference to the Nietzsche book in a glowing review of Prideaux’s more recent biography of Paul Gauguin.

It seemed like a good way to find out more about Nietzsche, somebody whose name is dropped frequently, but who I know next to nothing about.

But, more importantly, the tone of the review (another reason Five Books is one of my favourites) made me know I’d love Sue Prideaux’s writing.

And so it proved. Dry, cerebral, stylish, witty: Prideaux is clearly drawn to flawed historical egotists, and she has a lot of fun with a cast of brilliantly odd and entertaining characters. And, of course, she also does a great job of explaining why Nietzsche holds such an important place in the history of Western philosophy.

Still, by far the most interesting and entertaining aspect of I Am Dynamite! is the way Prideaux explores the tangled, narcissistic creative insecurities of Nietzsche and collaborators such as his one-time friend-turned-nemesis Richard Wagner.

It’s all there. The fragile egos. The deep need for validation. The wild mood swings between ‘Actually, this is pretty good!’ to ’Christ. This is shit’.

In other words: exactly the kind of neurotic energy I see in myself every time I sit down at ye olde laptop, or go to share my work in Insta.

Anyway, I enjoyed this book so much I ended up taking notes; which eventually evolved into this short piece.

Sure, there are a few reflections on the book itself, and a few thoughts on how Nietzsche’s views have a certain diabolical resonance today.

But mostly, it’s a reminder that the creative meltdown has a long and noble tradition - and that even history’s tortured geniuses were just trying to figure it out, like the rest of us.

1. Nietzsche was an early Blue Health adopter

“Never trust a thought that occurs to you indoors” - Friedrich Nietzsche, Ecce Homo

Nietzsche, Prideaux tells us, “did his best thinking in the open air. Place was vitally important to him.”

Swimming was a key passion, a “lifelong recreational delight.” A proto-cold dipper who, in another era, would deffo have worn his camo Dryrobe on the weekly Lidl run, I Am Dynamite! is full of references to what these days must by law be referred to as ‘wild swimming’.

At times of high stress, in a manner familiar to anybody who has looked at social media at any point in the last decade, it also endowed considerable mental health benefits - as in Bayreuth in 1872, when, overwrought by his falling-out with Richard and Cosima Wagner, he sought sanctuary in the garden of his friend Malwida von Meysenbug:

“He took long swims in the waters of the little river that flowed through the garden. It was a regime that did him so much good that … he had to admit that his soul could not help but submit.”

Equally vital to his wellbeing were his legendary rambles around the Alps. In the early years, intense, transformative conversations during epic Alpine walks with figures like Richard Wagner or Lou Salome helped shape his thinking.

Later, as he matured as a philosopher, these increasingly transcendental yomps were more solitary, but no less creatively essential.

With his eyesight failing, works like Thus Spoke Zarathustra were, Prideaux tells us, composed on the move, and:

“..divided into the small, intensely compressed sections that he could manage to organise while on his four- or six-hour walks and transfer into his notebooks without any practical help. The landscape of his inspiration took the path round the two little lakes of Silvaplana and Silsersee whose intensely turquoise water formed the shimmering floor to the luminous overhang of steep-sided mountains capped with eternal snows. It was a completely self-contained world…”

Little wonder that, towards the end of his life, a reflective Nietzsche concluded the following:

“Philosophy, as I have understood and lived it, is voluntary living in ice and high mountains.”

2. You can’t escape history

“History doesn’t repeat itself, but it often rhymes.” – Mark Twain

Like all philosophers, Nietzsche was thinking on the grandest scale of all, trying to understand the movements of history, the nature of creativity, and recurring patterns of human behaviour within the context of four thousand years of cultural thought and historical suffering.

Which is why his observations about the cyclical patterns of history - and how they influence creativity and civilisation - are a tad concerning in the context of the period we’re currently living through; in which technology, cultural anxiety, and political rage are combining in ways that would’ve had Nietzsche nodding grimly from the sidelines.

Case in point: the philosopher’s ongoing series of conversations with his pal Jacob Burckhardt, during which they reasoned that true creative energy often emerges out of societal extremes - especially violence and upheaval.

This, the pair decided, meant that “extreme barbarity is no cultural hiccup occurring only when a civilisation is sliding into decadence; rather, it is a necessary part of the fabric of creativity.”

In the end, they bleakly concluded, this inevitably leads to “demagogues armed with all the potentially terrible weapons provided by industrialisation, science and technology” wreaking barbarous havoc on society.

Remind you of anybody?

3. Even geniuses have to battle health issues

“Does the mind rule the body?/Or does the body rule the mind?/I dunno” - The Smiths

Nietzsche’s creative doggedness in the face of a truly grim list of health issues is almost comically bloody-minded.

Take the summer of 1872. His eyesight had deteriorated to the point where “light was agonising.” He spent his days in a darkened room, venturing out only when cloaked in a sunshade, thick-lensed green-tinted spectacles, and a beak-like visor jutting out over his forehead.

Things got worse. A prescription of “eyedrops of deadly nightshade” - yep - doubled the size of his pupils, turned the world into a “dancing blur,” and gave him such a grotesque appearance that even his closest friends recoiled.

For someone whose life revolved around reading and writing, this could have been a death blow. But with the help of his sister Elisabeth, who managed the domestic side of things, and his friend Carl von Gersdorff, who read aloud to him and helped organise his source material, Nietzsche carried on. More than that, he somehow turned this wretched episode to his advantage.

As Prideaux reports, von Gersdorff believed this laborious new method actually sharpened Nietzsche’s thinking: “both his material selection and his delivery were improved… which left Nietzsche speaking more clearly and eloquently, and with more concentration.”

Nietzsche, unsurprisingly, took it even further - casting the whole ordeal as a personal breakthrough:

“The illness gave me the right to change all my habits completely; it permitted, it required me to forget… my eyes alone put an end to my bookworm behaviour; I was redeemed from ‘the book’…. The greatest blessing I ever conferred upon myself.”

One to remember the next time the man-flu kicks in.

4. All creative people are fragile snowflakes

One of the joys of reading this book is the frequent and often hilarious reminder that even titans like Nietzsche and Wagner were basically stressed, petty creative egomaniacs - endlessly fretting over why their friends hadn’t fed back on their latest work, how they were going to fund their next project, why nobody would review their book, and so on.

Consider Nietzsche’s ongoing battle with his own planet-sized creative ego. On the one hand, he’s the epitome of the lone, questing intellectual - railing against newspapers as a destructive new technology destined to obliterate attention spans and distract the masses from serious thought.

On the other, he’s absolutely desperate for his first book, The Birth of Tragedy, to be reviewed. Anywhere. By anyone. When it finally is, he celebrates by buying fifty copies of the review.

No less relatable are the constant stresses about money and budgets.

Even Wagner - who’d been gifted one of the grandest houses in Switzerland by King Ludwig II, and given free rein to redesign the entire town of Bayreuth in his image (all at someone else’s expense) for his planned festival celebrating his own work (it still takes place every year) - never stopped worrying about how he was going to pay for his next project.

Above all, like every artistic person since the dawn of time, Nietzsche was quietly terrified that his work was rubbish.

As a result, he constantly sought validation from his peers — like the time he unwisely tried to win Wagner’s approval for his own amateurish musical compositions.

That Nietzsche was a brilliant musical improviser was unquestioned; so much so that one spontaneous performance apparently moved Cosima Wagner to tears.

Unfortunately, his famous pals were less enamoured with his ability as a composer, and when he wrote an original piece called Manfred Meditation as a Christmas present for Cosima, trouble ensued.

Using a devastating passive-aggressive tactic familiar to anybody wondering why their close friends haven’t liked or shared their latest work on Instagram or Facebook, Cosima and Richard Wagner disliked it so much they simply pretended it had never happened: even ignoring Nietzsche’s plaintive, ill-advised letters on the subject, in what has to be one of history’s more brutal ghostings.

Unfortunately for Nietzsche, his old friend Hans von Bülow had no such scruples, sending him a devastatingly frank critique, in which he described Manfred Meditation as:

“...the most extreme in fantastical extravagance, the most unedifying and least uplifting, the most anti-musical thing that I have come across in a long time in the way of notes put down on paper... More than once I had to ask myself: is this all some awful joke? Did you perhaps intend a parody of the so-called Music of the Future? Is it with conscious intent that you express an uninterrupted scorn for all the rules of tonal connection, from the highest syntax to the usually accepted orthography?”

As Sue Prideaux explains, the impact was devastating. Nietzsche didn’t leave the house for three months, and it would be decades before he dared share his music with anyone outside his immediate family.

5. If in doubt, self-publish

Considering how little he is understood or even read these days, Nietzsche’s influence has always been outsized. Perhaps it’s because he embodies one of the most romantic and poignant creative tropes of all: the questing artist who dies in obscurity, only for his work to be belatedly discovered and celebrated after death.

Success - of a kind - came early, thanks to the moderate reception of The Birth of Tragedy, which briefly caused a stir among Europe’s intellectual class.

From there, commercially if not creatively, it was downhill all the way. Some of the funniest (and most recognisable) relationships in I Am Dynamite! are between Nietzsche and his long-suffering publishers and editors - endlessly tearing their collective hair out as the writer disappears down ever-more quixotic paths, submitting commercially suicidal (and, by the end, illegible) manuscripts; torpedoing his already tiny audience with every release.

Not that Old Dynamite himself cared. In fact, the less well-received his work was, the more he doubled down.

When his publisher Ernst Schmeitzner flat out refused to publish the fourth volume of his Thus Spoke Zarathustra series, Nietzsche cashed in part of his University of Basel pension and printed a meagre forty copies himself, distributing them to a small coterie of friends and colleagues - hardly any of whom acknowledged its existence.

By 1886, Nietzsche was eking out a bleak, peripatetic existence, living off that same meagre pension, and moving between small hotels in Turin, Sils-Maria, Florence, and Nice,

And yet, still, the revolutionary work continued, as Prideaux describes:

“Seen from the outside, Nietzsche's life during 1886 and 1887 looks quiet and harmless, but it was during this time that, with all the fury of the neglected prophet, he was examining the foundations of our moral and intellectual traditions and taking a hammer to them in the books of his mature philosophy.”

The result was his magnum opus, Beyond Good and Evil, which, once again, he decided to self-publish:

“As no publisher had the slightest interest in publishing his work, he would publish it himself. He would have it printed privately at his own expense in an edition of six hundred copies. If he sold three hundred, he would get his money back. Surely that was not impossible?”

In the end, it sold a mere 114.

Months later, Nietzsche would be certified insane. He spent the rest of his short life being shunted around various insane asylums, completely unaware that his work and ideas had finally achieved the global renown he always craved: let alone that he would eventually be considered one of the most influential figures in twentieth century culture, cited by everybody from Stanley Kubrick (see below) to Don King (true story).

And maybe that’s the thing to remember. Despite the illnesses, the rejection, the feuds, the mortifying reviews of his musical side hustles, and the shockingly poor sales figures - Nietzsche kept at it until the very end.

Something to keep in mind the next time you’re staring down a blinking cursor, or a half-finished side project, and wondering what on earth the point is.

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It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been pissing about for a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

How can I spend more time doing the things I’m passionate about?

What does a ‘successful’ creative life actually look like?

Find out more below.

Four years ago, I had the idea of trying to find a practical way to help new creatives and storytellers get into the industry.

Regular listeners to my podcast Looking Sideways will no doubt remember that this idea eventually became the brilliant Db Fund, which we first launched back in 2022.

So it was amazing to partner once again with my friends at Db on the second Db x Looking Sideways Fund, which we launched back in January 2025.

If you missed the official (ahem) announcement, catch up here:

Use my Db Journey discount code LOOKINGSIDEWAYS for a whopping 15% on any purchase.

As ever, the response to our call out for new creatives was completely incredible. We had hundreds of entries to this year’s Db Fund - so many, in fact, that it’s taken us far longer to get through them than we expected.

In this Herculean task, we’ve been aided by our brilliant judges: Pacha Light, Chris Burkard, and Luis Medearis; three Db-affiliated creatives who know a thing or two about conceptualising, financing, and distributing their own projects.

We’re currently whittling our longlist of 12 finalists down to a final shortlist of five, and we’ll be announcing those finalists soon.

In the meantime, back in February, I caught up with Chris, Pacha, Lu and Db CMO Jon Weaver for a live Creative Exchange.

As ever, this was a brilliantly insightful conversation during which our trio of judges gave us the lowdown on how they launched their own creative careers, as well as discussed what they’re looking for when choosing our five finalists.

Among other things, we discussed:

Safety in numbers: how Lu and his Technically Doing It crew have joined forces to offer brands a more compelling creative proposition.

“It was like someone flipped the lights back on.” - the lightbulb moment that reignited Chris Burkard’s creative passion.

“If you’re waiting for the perfect moment, you’ll be waiting forever. Just start.”

The story behind Ceibo, Pacha’s brilliant new film collaboration with Lucy Small and Maddie Meddings.

How the trio choose their own creative projects.

What they’ll be looking for when judging the Fund

Watch our conversation below:

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It’s eight weeks since I released The Announcement, and I continue to be amazed at the ongoing response.

In the last two weeks alone, I’ve been chatting about the show with Wavelength, The Adventure Podcast, The Ski Podcast, Bomb Snow, Adventure Magazine and Huck.

Here are a few of the notices the series has received since its release:

“Hits with truths you may not want to hear” Wavelength Magazine

“The definitive work on the subject of sustainable business” Surfer Magazine

“The current must-listen for anybody in the outdoor industry” Outdoor Industry Compass

“Examines the damage done by conventional modern philanthropy and how and why billionaires should stop using it as a platitude magnet and ego-boosting game. We need this now more than ever - you listening, Musk, Bezos, Zuckerberg?” Brooke Roberts-Islam, Techstyler/Forbes

“An exceptional series and highly recommended for anybody interested in what the future of capitalism looks like” Bronwen Foster-Butler, CMO, Finisterre

“A masterly podcast that unpacks the story of new ownership models in business” Erinch Sahan, Business Lead, Doughnut Economics Action Lab

“Captures the thinking on the future of evolutionary paths of business, markets and capitalism” John Elkington, Founder, Volans

I always hoped the series would find an audience, and it turns out the themes I explored in the three episodes (the democratic impact of unaccountable billionaires making decisions on behalf of the rest of us; the reality of the trade off between extractive capitalism and ‘business for good’; how we combat the climate crisis; the impact of corporate philanthropy) could not have been more timely - especially in the age of Trump and Musk.

All of which is why I have decided to evolve The Announcement into a standalone series - akin to my much-loved and much-missed Type 2 series - through which I’ll continue to explore these themes through new conversations, episodes, and investigations.

So how is this going to work?

As trailed for quite a while now, I’ll be releasing the longform versions of the interviews that formed the foundation of the series as planned.

Next week’s first follow-up episode with Carl Rhodes (in which I spoke to Carl for a second time, to get his take on billionaire influence in the context of Musk and Trump) will be free.

Subsequent instalments with other Announcement contributors such as John Elkington, Imandeep Kauer, Audette Exel, Erinch Sahan, Markus Lux and Chuck Collins, will be exclusively for my paid Insights community.

Find out more about that below:

Insights is my new Looking Sideways section, exclusively for my paid subscribing community.

It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been pissing about for a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

• How can I spend more time doing the things I’m passionate about?

• What does a ‘successful’ creative life actually look like?

Here are a few recent Insights articles to whet your appetite:

In addition, I will be recording an ongoing series of follow-up interviews.

I’ll be speaking to people such as Jon Alexander about his book Citizens, and David Gelles about his biography of Chouinard, Dirtbag Billionaire. I’m also planning to follow up with Patagonia, to get their take on the series, and to ask them some of the questions listeners have posed since listening to the series.

These new episodes and conversations will be free for everybody, and I’m excited to see where this new strand of The Announcement leads.

Before all that - a follow-up blog on the creative lessons I’ve learned while making The Announcement.

As my Insights subscribers will know, I’ve also been posting a number of behind-the-scenes films over the months, in which I explored some of the thinking that went into the series.

In the last of these (which Insights subscribers can watch above) I began to explore what I learned during the making the series, and from the subsequent critical response.

I’ve now expanded these thoughts into the following blog, and I’d love to know what you think, and how this chimes with your own experiences of putting your own creative work out into the world.

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This is the third behind-the-scenes video diary for THE ANNOUNCEMENT, which is out a little later than anticipated. That’s because I just spent ten brilliant days in Sri Lanka on a total post-Announcement break (I posted a few highlights on that Insta post above).

With the entire series out for a few weeks now, and reactions from listeners and press continuing to come in, I’ve been reflecting on the reaction to the series, and the five standout things I’ve learned during the making of the show.

These are:

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Welcome to the second behind-the-scenes video diary for THE ANNOUNCEMENT. The entire series is out now, and it’s been brilliant this week seeing the response, especially from the world of sustainable business. It was always really important that this constituency took the documentary seriously, so I’m grateful to the influential thinkers in this space who has been sharing their thoughts, as below.

As ever, in this week’s behind-the-scenes video, I’m discussing what I got right, what I got wrong, criticism I’ve received, questions I’ve received, and delving into some of the decision-making behind this series.

You can watch the second one above - and if you’ve listened to episode 2 I’d love to know what you think.

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As you’ll know if you follow me on any social media platform, THE ANNOUNCEMENT is out! As I’ve detailed in many, many posts over the months, I’ve been working on this project for almost two years. So I’m very glad to get it finished. I’m also hugely grateful for all the comments and feedback from listeners and members of ye olde Looking Sideways Substack community.

For the next few weeks I am going to be releasing behind-the-scenes video diaries for each episode, where I discuss my thoughts on what I got right, what I got wrong, criticism I’ve received, questions I’ve received, and generally indulge in a little collective debrief.

You can watch the first one, above.

I’d also like these episode debriefs to be a space for the Insights community to discuss their own thoughts on the series and episodes, and the points and topics I raise in the diaries. You know what to do…

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I’ve spent the last couple of years writing, producing and recording this series, and I’m really proud of it. I’ve spoken to the people at Patagonia behind the decision; as well as World Bank economists, the academic who wrote the book on ‘Woke Capitalism’, and experts in sustainable finance, philanthropic capitalism, and US tax law.

The result is THE ANNOUNCEMENT. Here’s how I’m describing the whole series:

"Earth is our only shareholder.”

In September 2022, Patagonia's billionaire owner Yvon Chouinard relinquished control and made 'earth' the company's only shareholder.

But … what did this actually mean? Why did he do it? What about the scrutiny the company received? And is this really a critical moment in the history of capitalism, as Patagonia believe?

The Announcement is a new three-part podcast documentary series from Looking Sideways, hosted by Matt Barr.

This is a story about legacy, purpose, what we leave behind, and courageous people doing things differently.

It’s about capitalism, democracy, the movement of money, and the history of giving it away.

Above all, it’s about the power of symbolism, and the importance of storytelling when it comes to helping us get our heads around something as vast and conceptual as the climate crisis, and our own role in it.

Above is a trailer - made by the endlessly talented Owen Tozer, and with music by the great Ben Townsend, who wrote the score for the entire series.

I’d be hugely grateful for any help spreading the word with this when the time is right. The main series will be released in January 2025, although this week I’ll be sharing a special panel discussion about the series and its themes, recorded at Kendal and featuring my friends Steve Scott, Phil Young and Lauren MacCallum, exclusively for my Insights subscribers.

Big up to my friends, colleagues and family (especially Alima), who have been so supportive and such brilliant sounding boards as I’ve droned on about this for the past 24 months. And thanks to Patagonia and Gary Regester for the use of the Yvon Chouinard image in the trailer.

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As regulars will know, I’m on a mission to help my Insights paid subscribers find their own answers to two fundamental questions:

How can I spend more time doing the things I’m passionate about?

What does a ‘successful’ creative career really look like?

That was the thinking behind my three-part series on the reality of earning money as a freelance creative.

If you missed this the first time around, catch up below:

As this series was so popular, I’m back with another two-parter: discussing in this first instalment the reality of how freelance photographers make their money with Chris Burkard, Bella Rose Bunce, Hannah Bailey and James Bowden.

Photographers are in a particularly interesting position these days. Gone are those pre-digital days, when analogue syndication meant photographers could establish a niche for themselves while also making some proper cash.

The advent of digital scuppered that business model for all but those at the very top of the food chain.

For the rest of our lens-toting brethren, as my interviewees discuss, the reality of life as a photographer means a constant hustle of endless pitching and brand collabs; and finding a way of parlaying your talent into revenue in an increasing precarious media landscape.

As ever, expect the same intriguing and compelling mix of insight and vulnerability that has made this series such a hit (and look out for part 2, as well as future instalments on how journalists, film-makers, and activists make money, in 2025).

1. Chris Burkard

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