The Convex Bet: Why Running a Photography Business at a Loss Makes Perfect Sense

I make approximately £3,000 a year from 32,000 images. After travel costs, I'm operating at a loss. Any business advisor would tell me to quit. Any efficiency consultant would want to "fix" my operation. They'd both be wrong.

What looks like failure under conventional business metrics is actually a sophisticated bet on randomness—one that provides financial optionality, intellectual stimulation, and genuine freedom. Understanding why requires understanding a concept the writer Nassim Nicholas Taleb calls "antifragility."

The Paradox of the Losing Bet

Let me lay out the economics plainly. I'm a press photographer with Westminster and Downing Street access. I attend around 70 sessions in London annually, plus another 25 local assignments in Brentwood, Southend, and Epping. Travel costs alone run perhaps £2,000-3,000 per year. Revenue: £3,000. The arithmetic is not encouraging.

But here's what that arithmetic misses: I'm not trying to make £3,000 predictably. I'm maintaining exposure to rare, high-value events that could return multiples of my annual costs in a single image. This year's best-performing image returned £500. My modal image sells for £20 or sits unsold. That's not a bug in my business model—it's the entire point.

Standard business thinking tries to maximize average returns. But in news photography, average returns are meaningless. What matters is whether you're positioned when the non-average event occurs.

What Antifragility Actually Means

Most people think antifragility means resilience—the ability to withstand shocks. It doesn't. Resilient systems resist damage. Antifragile systems actually gain from volatility, randomness, and disorder.

News photography has inherent antifragile structure, but only if you set it up correctly. You need:

1. Small, repeated, bounded losses - I can't lose more than £30-50 on any given day (travel, time opportunity cost)

2. Exposure to unlimited gains - A single image could return £500, £2,000, or more if genuinely historic

3. Benefit from volatility - Political chaos is bad for predictable businesses but excellent for news photography

4. No catastrophic downside - Unlike leveraged businesses, I can't go bankrupt from this work

The payoff curve is nonlinear. I lose small amounts repeatedly, but occasionally gain large amounts. That asymmetry—where losses are capped but gains are not—is the signature of convexity.

Compare this to the institutional photographer on salary: fixed high costs, predictable output required, gains capped at their salary level, exposed to catastrophic downside (redundancy). They've eliminated randomness, which sounds prudent but actually eliminates the source of value in news. When a national paper laid off its entire photography staff, those photographers had optimized for "stability" right into fragility.

The Option Premium (And Its Hidden Costs)

Each day at Westminster is an option. I pay a premium (travel costs, time) for the right—but not obligation—to capture whatever happens. Most days, nothing happens. The option expires worthless. That's supposed to happen.

Standard options theory explains why this still makes sense. When I attend Prime Minister's Questions, I'm paying perhaps £35 in travel and six hours of time for exposure to whatever occurs. Most sessions are routine. But I was there when Boris Johnson resigned. I was there when Formula One visited Downing Street. I captured Fei-Fei Li, the AI researcher, at a moment when her presence signaled policy directions most photographers missed.

What the theory doesn't mention is that maintaining this optionality comes with costs that don't appear in any textbook. Downing Street, for instance, has no toilet facilities for the press. None. This becomes an increasingly significant consideration for a 67-year-old during four-hour waits for ministerial arrivals. Strategic planning of coffee consumption becomes a skill in its own right.

Then there's the minor indignity of becoming a news item yourself. I once fell asleep while waiting in Downing Street—not surprising given the interminable delays that characterize political theater—and was photographed by a colleague. The image circulated. Professional hazard, I suppose, though it does rather undermine one's dignity as a serious documentarian of state affairs.

There was also the occasion when someone attempted to steal my camera bag outside the Cabinet Office. In retrospect, this was perhaps the ultimate validation of the equipment's value, though at the time it was simply alarming. The would-be thief clearly understood the asymmetric payoff structure better than most business consultants.

And every so often, you're challenged by armed police outside Portcullis House despite having credentials, because you've positioned yourself in a spot they've decided requires additional scrutiny. Being questioned by officers with automatic weapons provides a certain clarity about the seriousness of the environment you're working in. It's humbling, if nothing else.

None of these experiences appear in my cost-benefit analysis. But they're part of the option premium—the unglamorous reality of maintaining positioning for rare valuable events.

The amateur mistake is calculating success rate: "I attended 70 Westminster sessions but only sold images from 15, so my hit rate is 21%."

The correct analysis asks: what was the payoff asymmetry? If those 15 sessions returned £2,000 on £2,500 in total annual costs, the average arithmetic looks poor. But if one of those sessions could have returned £5,000 for a genuinely historic moment, I'm not paying for average returns. I'm paying for exposure to the tail of the distribution.

You can't capture the resignation of a Prime Minister if you optimized yourself out of Westminster six months earlier for "efficiency." Though you might have avoided being photographed asleep, which is something.

Why Efficiency Metrics Destroy Value

Every conventional business metric would make my operation worse:

Revenue per hour worked? If I optimized for this, I'd stop attending routine sessions where "nothing happens." But I can't predict which routine session will suddenly become historic. Optimizing for efficiency would systematically remove me from optionality. It would also mean I'd miss out on all the character-building experiences like bladder management strategy and negotiations with armed police officers.

Conversion rate (images shot vs. images sold)? Maximizing this would mean only shooting obvious moments everyone else is shooting. The competitive advantage lies in being positioned for non-obvious significance—which means accepting lower conversion rates and the occasional stolen nap.

Cost reduction? Cutting travel costs means attending fewer sessions, which reduces my exposure to rare high-value events. The cost isn't waste; it's the option premium. Plus you miss the entertainment value of watching someone try to steal professional camera equipment in one of the most heavily surveilled locations in Britain.

The metrics that actually matter:

• Am I maintaining access to high-optionality environments?

• When I do capture value, what's the payoff multiple?

• Are my costs bounded so that losses can't eliminate me?

• Am I positioned for the kind of randomness that benefits me rather than harms me?

• Have I worked out where the nearest public toilet is?

My £3,000 revenue is essentially irrelevant to whether this is working. The real question is: am I still in the game when something genuinely historic occurs?

The Barbell Strategy

Taleb describes the barbell strategy: extreme safety on one side, extreme risk-seeking on the other, nothing in the middle.

My practice follows this pattern:

Safe end: No debt, minimal fixed costs, no staff, no studio rent, no equipment financing beyond what I choose. I can walk away tomorrow. My pension is secure. Photography income is non-essential. Maximum protection against ruin.

Risk end: Maximum exposure to rare, high-value events through Westminster credentials and Downing Street access. I'm not trying to predict which session will produce news, just ensuring I'm present when it does. Even if that means standing outside the Cabinet Office long enough to become a target for opportunistic theft.

Avoid the middle: I'm not trying to be "somewhat profitable" or "moderately efficient" or generate "steady income." Those middle strategies would reduce my exposure to valuable tail events. The photographer who optimizes for steady £100/day revenue will systematically miss the positioning needed for the £5,000 image. They'll also avoid being challenged by armed police, but you can't have everything.

This structure is antifragile: I cannot be ruined by the downside, but I'm fully exposed to the upside.

Skin in the Game and Real Learning

I have complete skin in the game. Every positioning decision has direct consequences. Wrong call about which session to attend? I eat the cost. Right call? I capture the gain. No corporate buffer, no salary to cushion mistakes.

This creates genuine learning that can't be taught from textbooks. Over twelve years and thousands of decisions, I've developed judgment about:

• Which types of sessions have higher option value (Budget days, Prime Minister's Questions, crisis periods vs. routine arrivals)

• How to recognize non-obvious newsworthiness before it's widely understood

• Where to position physically for coverage

• What actually sells versus what seems significant in the moment

• Which coffee shops near Westminster have the most reliable facilities

• How to explain to armed police that yes, you're supposed to be here

• The optimal angle for sleeping while appearing merely contemplative

When Fei-Fei Li appeared at Downing Street, most photographers wouldn't have known who she was or why her presence mattered. My recognition came from understanding AI policy directions, not from predicting her specific appearance. That's information asymmetry converted to value—but only because I was positioned to exploit it.

This calibration only develops through repeated exposure to consequences. The salaried photographer, insulated from direct feedback, never develops this refined judgment. They shoot what their editor requests, and whether it sells is someone else's problem. They also probably have access to better facilities and don't risk becoming subjects of colleague's photography while catching forty winks.

Taleb argues that only those with skin in the game develop accurate models of reality. Everyone else is theorizing without consequences.

The Value of Unique Positioning

Here's a counterintuitive truth I've learned: some of my most interesting photographs—though not necessarily my most profitable—have come when I've been alone or with just one other photographer in Downing Street, outside the Cabinet Office, or on College Green.

The packed press pen at major events produces competent, professional images that dozens of other photographers also capture. The market is flooded. Everyone has essentially the same shot, taken from roughly the same position, at the same moment. The value of any individual image in that scenario approaches zero, regardless of technical quality.

But show up on a quiet day when something unexpected happens, and you might be the only photographer there. Or one of two. That scarcity creates value in a way that technical excellence alone never can.

The images I'm most satisfied with—the ones that feel genuinely mine rather than just another version of what everyone else got—tend to come from these moments. A minister arriving unexpectedly when I happened to be positioned outside the Cabinet Office. An impromptu statement on College Green when most photographers had already left. The quiet interactions that happen when official proceedings have ended but people are still present.

These aren't necessarily the images that return £500. Often they sell modestly or not at all. But they represent something the crowded, choreographed moments don't: unique visual documentation of moments others didn't capture. That's where genuine value lives, even if the market doesn't always immediately recognize it.

This is another form of optionality. By maintaining presence even when it's not "optimal" by attendance numbers, I'm exposed to the rare moments when being the only photographer there transforms an unremarkable scene into something with actual scarcity value. You can't predict these moments. You can only be positioned to capture them when they occur. Though being the only photographer there also means you're the only target if someone's looking to nick equipment, so there's that trade-off.

The institutional photographer, working to a schedule of predicted high-value events, systematically misses this entire category. They're optimized for the packed press pen, not for the quiet Tuesday afternoon when something interesting happens and there's no one else there to document it. Or to fall asleep and become the story themselves.

The Intangible Payoffs

Here's where the conventional cost-benefit analysis really breaks down. At 67, with 35 years of senior HR experience behind me, I'm not optimizing for income. I'm optimizing for life quality and cognitive function.

The work provides:

Intellectual stimulation: Pattern recognition, news judgment, political analysis, understanding power dynamics. Every session requires active thinking about what matters and why. But equally valuable are the conversations—with broadcast crews waiting for the same moment, with other photographers comparing notes on equipment and technique, with journalists analyzing what they've just witnessed. These aren't casual chats. They're exchanges with people who are themselves intelligent observers, often with specialist knowledge I lack. A cameraman explains why they're positioned for a particular angle. A political correspondent shares context about backroom tensions that haven't yet surfaced publicly. Another photographer discusses the technical challenge of shooting in difficult light while we're both solving the same problem in real time.

Over twelve years, some of these encounters have developed into genuine friendships—people I now recognize across the press pen, whose judgment I've come to respect, who remember previous conversations and pick up threads from weeks earlier. Some of whom have photographic evidence of me sleeping on the job, but we don't talk about that.

Physical activity: 70 days in London means 70 days of walking, standing, positioning, carrying equipment. Plus 25 local assignments. This is structured exercise that doesn't feel like exercise, embedded in purposeful activity. Though the bladder control challenges add an element of physical discipline that most fitness regimes don't include.

Fresh air and engagement: Hours outside, in the flow of events rather than isolated at home. The social dimension matters more than I initially recognized. There's a community in the press pen—not intimate, but real. Shared dark humor about delayed arrivals, collective problem-solving when security changes access routes, the particular camaraderie of people who've stood in the cold together waiting for something that may not happen. Mutual understanding about the indignities of working without facilities. The knowledge that everyone has been challenged by police at least once despite having perfectly valid credentials.

Autonomy: Every decision about where to go, when to shoot, what to submit is mine. No boss, no schedule imposed from outside, no requirement to attend anything. The freedom to position myself is itself valuable. Even if that positioning occasionally attracts unwanted attention from either thieves or security.

Access to information: Being physically present at Westminster provides understanding of political currents that no amount of media consumption replicates. I see who's talking to whom, read body language, observe the informal dynamics that don't make it to broadcast. And crucially, I hear the interpretation from people whose job is to understand these dynamics—the running commentary, the speculation, the pattern recognition from journalists who've covered politics for decades. This is distributed intelligence, freely shared in the moment because we're all trying to make sense of the same events.

Character development: Getting challenged by armed police builds character. So does having your camera bag targeted for theft in one of the most surveilled locations in Britain. And there's something humbling about being photographed asleep by your peers. These aren't experiences you'd seek out, but they're oddly valuable in retrospect.

These benefits don't appear on a profit-and-loss statement. Try to quantify "cognitive engagement at 67" or "autonomy in daily decision-making" or "being present at historic moments" or "friendships formed through shared professional practice" or "the satisfaction of capturing something no one else got" or "ability to maintain composure when armed officers question your credentials." You can't. But their absence has a cost that compounds over years.

If I spent those 95 days sitting at home, would I save £2,000 in travel costs? Yes. Would I be better off? Absolutely not. Would I have better toilet access? Undeniably. But you can't put a price on dignity anyway.

The Social Capital Hidden in the Numbers

There's another layer to this that becomes apparent only over time: the social capital accumulated through regular presence.

When you show up consistently, you become known. Other photographers recognize you, remember your name, start conversations. Some of them have compromising photographs of you sleeping, but that apparently doesn't disqualify you from professional respect. Broadcast crews know you're reliable for a quote or a perspective. Security staff recognize you and the credential checks become smoother—though apparently not smooth enough to prevent the occasional armed challenge, which keeps you alert.

This matters practically: when something unexpected happens, the people around you share information more freely with someone they know than with a stranger. "Cabinet Office just called an emergency meeting"—that kind of thing gets mentioned to people who've been standing in the cold together for two years, not to someone who shows up once. "Someone's trying to nick camera bags" also gets shared, which has practical value.

But it matters more than practically. Humans are social creatures, and having a professional identity that connects you to a community has psychological value that retirement often strips away. I'm not just "a retired HR director." I'm a working press photographer, part of a loose but real professional network, with colleagues who know my work and whose work I respect. Some of whom have documented my less dignified moments, but that's apparently what friends do.

The friendships aren't numerous—this isn't a social club—but they're genuine. Coffee before a session with another photographer discussing the political implications of a reshuffle. Comparing notes with a cameraman about how different news organizations are covering the same story. The colleague who remembers you mentioned kidney function issues months ago and asks how the latest results came back. The quiet agreement that we'll never speak of the sleeping incident again.

These connections have value that can't be reduced to revenue. They're antifragile in their own way—low maintenance, high resilience, occasionally providing unexpected value (a tip about an upcoming event, warning about increased security, or simply good conversation that makes waiting in the cold less tedious).

The Lindy Effect and Growing Value

My 32,000-image archive isn't just current inventory—it's accumulating value over time in ways that invert normal business depreciation.

Images from a decade ago of then-junior politicians become more valuable as those politicians rise to prominence. A backbencher photographed in 2015 who becomes Foreign Secretary in 2025—those early images appreciate. Routine meetings that seemed insignificant at the time gain historical context as preludes to major policy shifts.

This is antifragile behavior in time. Most business assets depreciate. My archive appreciates through:

• Subject career progression

• Historical context shifts

• Increasing scarcity (fewer photographers had access then)

• Narrative value for media retrospectives and profiles

• Unique documentation of moments others didn't capture

• Probably some images of me sleeping that will become valuable as cautionary examples

The "loss" I'm running might actually be building a long-term asset that compounds in non-obvious ways. I'm not trading time for current income; I'm building optionality that increases with age.

Taleb calls this the Lindy effect: things that have survived gain additional life expectancy. Every year my archive survives increases its expected future value. Every year I survive the various indignities of the profession adds to my credibility.

Where This Model Breaks

Intellectual honesty requires noting where the antifragility analogy fails:

Scale limitations: I can't easily scale this model. Adding another photographer doesn't double the optionality—it adds coordination costs and splits the upside. Though it might mean someone else gets photographed sleeping for a change.

Personal non-transferable benefits: The cognitive engagement, autonomy, and social connections are real but specific to my situation—retirement age, financially independent, seeking intellectual stimulation and professional community. Someone needing current income can't adopt this model directly. Someone younger might also have better bladder control, which changes the calculus.

Credentialing barriers: Westminster access is credential-gated. My NUJ press card and decade of established access provide a moat. Without that, the option value disappears. Though the credentials apparently don't prevent occasional armed challenges, so there's a limit to their protective value.

Energy and aging: Unlike true antifragile systems that strengthen under stress, humans deplete with age. This model has a time horizon. At some point, the physical demands will exceed the benefits. The lack of facilities becomes more problematic with each passing year, not less.

Limited upside compared to other convex bets: While my downside is capped at £50/day (plus dignity), my upside is still bounded by image licensing economics. I'm not going to make £100,000 from a single image. Other convex structures (startup equity, certain financial options) have genuinely unlimited upside and probably better amenities.

The Deeper Pattern

What looks like an inefficient, loss-making photography operation is actually something else: a structured way to maintain optionality, cognitive engagement, physical activity, and social connection while retaining complete autonomy and exposure to potentially significant financial upside.

The £3,000 revenue versus £2,500 in costs is almost a rounding error in this analysis. The real returns are:

• Intellectual stimulation that compounds over years—both from the work itself and from conversations with intelligent professionals

• Physical activity embedded in purposeful work (including unexpected core strength from standing for hours)

• Exposure to rare but valuable financial events

• Autonomy in daily decision-making

• Access to information flows and the collective intelligence of the press community

• Positioning at the center of political narrative

• Professional friendships and loose-knit social networks that provide structure and meaning

• The satisfaction of capturing unique moments others missed

• Character development through various small humiliations

• An archive that appreciates over time

• Stories that become more entertaining in retrospect

Try to hire these benefits separately. How much would you pay for intellectual stimulation equivalent to 95 days annually of active news judgment and substantive professional conversation? For structured exercise that doesn't feel like exercise? For the freedom to make every positioning decision yourself? For front-row access to political events? For a professional community that recognizes your work and provides collegial support? For the creative satisfaction of documentation no one else achieved? For being challenged by armed police despite having valid credentials? For having your camera bag targeted by thieves? For being photographed asleep by colleagues?

Some of these have negative value individually. Collectively, they form something worth considerably more than the arithmetic suggests.

The arithmetic of £500 profit/loss is absurdly incomplete.

Why This Matters Beyond Photography

The broader lesson applies to any activity with convex payoffs—small costs, bounded downside, exposure to unlimited upside, benefits from volatility.

Most people optimize their lives for predictable, steady returns. Get a stable job. Eliminate risk. Maximize efficiency. Plan everything. Ensure access to adequate facilities.

But some of life's highest values come from exposing yourself to positive randomness while protecting against catastrophic downside:

• Having interesting conversations with strangers (small time cost, occasionally life-changing connection)

• Reading widely outside your field (mostly irrelevant information, occasionally transformative insight)

• Attending events where interesting people gather (usually uneventful, occasionally pivotal)

• Maintaining capabilities you rarely use (seems wasteful until the moment you need them)

• Showing up consistently in professional spaces where relationships develop organically over time

• Being present when everyone else has left—the unique opportunity often comes in the quiet moments

• Accepting small indignities for the occasional extraordinary payoff

The pattern is the same: accept small repeated "losses" to maintain exposure to rare high-value outcomes. Protect the downside absolutely. Let the upside take care of itself. Try not to fall asleep on camera.

Press photography happens to make this structure particularly visible because we can measure it in pounds and images. But the principle applies far more broadly than anyone looking at my £3,000 annual revenue would suspect.

When people ask why I'm still doing this "unsuccessful" photography business at 67, I could point to the cognitive benefits, the exercise, the fresh air, the autonomy, the friendships, the satisfaction of unique work. All true.

But the deeper answer is simpler: I'm in the antifragility business. And business is good, even when the accounts say otherwise. Even when I occasionally fall asleep on the job. Even when armed police question my credentials despite having seen me a hundred times before. Even when someone tries to steal my equipment in front of multiple security cameras.

These aren't bugs in the system. They're features. They're evidence that I'm positioned where interesting things happen—to politicians, to policy, and occasionally to me. That positioning has value that no spreadsheet will ever capture.