The Second Product

I woke up last Saturday, sat down at my desk, and opened six browser tabs. One for each product I'm actively running.

• DailyPhotoTips needed a complete overhaul along with new content.
• Preflight needed a bug fixed before someone opened a GitHub issue about it.
• My blog had a half-finished draft staring at me (this article, actually).
• Hyperfocal was waiting for me to make a decision about pricing.
• DailyTips.dev needed some decisions on content and lead magnets.
• TheDailyPreset needed me to create five to ten new presets for our photography audience.
• And finally, my friend Gavin gave me a website, BestAIThings, that also needed my attention.

I closed the laptop and took the dog for a walk instead.

This is the second product problem. The logistics of running multiple things are just project management. The real problem is psychological. Every product you own is a version of you, and switching between them means switching identities. Your brain absolutely hates it.

Is the Identity Tax Real?

When I'm working on DailyPhotoTips, I'm thinking like a photographer and a newsletter operator. I'm thinking about open rates, seasonal content, what presets are trending, what our audience wants to see this week. I'm in creator mode, thinking visually, thinking about what inspires people to pick up their cameras.

When I switch to Preflight, I become a different person entirely. Now I'm thinking about CLI ergonomics, GitHub issues, developer experience, and whether my Go code is idiomatic enough that someone won't roast me in a pull request. I'm in engineer mode, thinking about edge cases and documentation and whether the README actually explains what the tool does.

When I open DailyTips.dev, I shift again. Different audience, different tone, different content strategy. Developers don't want the same thing photographers want. The lead magnets are different, the email cadence is different, the entire value proposition lives in a different universe.

When I sit down to write on my personal blog, yet another shift. Now I'm the person who thinks about behavioral psychology and business philosophy and tries to connect them in ways that don't sound like a LinkedIn post.

And then there's Hyperfocal, which needs product thinking. And TheDailyPreset, which needs creative work. And BestAIThings, which needs… honestly, I haven't figured that out yet. And oh, there's other I haven't even mentioned in this article. The list is long.

They're all different mental models, different audiences, different success metrics, different versions of me, and the transition cost between them is enormous.

Psychologists have studied this under the umbrella of "role conflict."

When people occupy multiple roles with competing demands, the cognitive overhead of switching between them produces measurable declines in performance and satisfaction. The research consistently shows that fragmentation burns people out faster than volume ever does.

Every time I switch products, there's a fifteen to twenty minute ramp-up where I'm not fully in either world. I'm still thinking about the email I should have sent to photographers while trying to debug a webhook integration for Preflight. The residue of the last identity lingers while the new one boots up.

Multiply that transition cost by seven products and several switches per day, and you start to understand why some weeks feel incredibly busy but nothing actually moves forward.

You end the week exhausted, open your task list, and realize you made incremental progress on everything and meaningful progress on nothing.

Having a Product Portfolio

Each product creates just enough progress to justify its existence but never enough to demand your full attention.

The photography business generates real revenue. DailyPhotoTips and TheDailyPreset are the proven engines, the things that actually pay bills and have proven distribution behind them. Over a decade of audience building, newsletter growth, partnerships, and the SEO kept building.

Those earn their place in the portfolio through cold hard math.

But the other projects? They each have their own gravitational pull.

Preflight has users who send nice emails and nice open source traction. DailyTips.dev represents an audience I understand deeply because I am that audience. Hyperfocal is an idea I've been excited about for a while. BestAIThings landed in my lap through a friendship, which I'm extremely grateful for.

Every single one of them has a case for existing. And that's exactly the problem.

I wrote about the endowment effect in a previous article. We overvalue things simply because we own them.

That emotional investment inflates the perceived value of each project far beyond what the market data supports.

The research goes deeper than mugs though. Studies on the interaction between the endowment effect and sunk cost fallacy show that this is a measurable cognitive distortion, one that makes people continue investing in things they already own, even when the evidence says they shouldn't.

The more effort you've put in, the harder it becomes to accurately assess whether that effort is producing returns.

So you keep them all alive. You water seven plants instead of letting five die so two can thrive, and you tell yourself you're being strategic when really you're being sentimental.

Growth Penalty

The math on this is unforgiving too.

DailyPhotoTips works because Brett and I gave it years of focused attention. Not months. Freakin' years.

The newsletter grew because we published consistently. Then the partnerships developed because we showed up, and the SEO worked because the content kept accumulating.

Every piece of that flywheel required sustained effort pointed in one single direction.

I wrote about this in Hey, Nobody's Coming. Distribution adds up over time, but only if you feed it consistently.

You know how it goes. The first 1,000 subscribers are brutal, and the next 10,000 are easier. But you have to survive the brutal part first, and the brutal part can last years.

Now imagine splitting that same effort across seven directions. Each product gets maybe 10-15% of your creative energy on a good week. None of them get the sustained attention that creates good returns. You're present everywhere and focused nowhere.

I've seen this play out in my own numbers.

The products that get consistent attention grow while the ones that get sporadic bursts of effort flatline.

Not because they're bad ideas (well, maybe some of them are, but that's beside the point), but because none of them get fed consistently enough to grow. Growth requires focus, and a multi-product portfolio is where focus goes to die.

I know the math. I've written about it. I've told other people that showing up consistently is the whole game. And yet here I am, spreading myself across seven things, watching the growth curves flatten on many of them because none of them get the attention density that DailyPhotoTips got during its growth years.

The diversification that feels responsible is often the riskiest strategy of all. Every bet gets diluted until none of them have enough behind them to pay off.

Why We Keep Doing It Anyway

If the math is so clear, why do builders keep accumulating products instead of focusing?

Because each new product solves a different emotional problem, and we don't like admitting that ¯\_(ツ)_/¯

The first product you build teaches you that you can build. The second product proves the first wasn't a fluke. The third product lets you explore a different identity. By the fourth, you've developed a pattern that feels like strategy but is actually compulsion.

I wrote about this compulsion in Human Ambition. Every single time I finish something, I start thinking about the next thing. The itch doesn't go away.

Money is part of the motivation, but it's not the whole thing. There's craft, recognition, impact, and this weird inability to sit still that I've stopped trying to diagnose.

The multi-product portfolio scratches all of these itches simultaneously. Photography scratches the creative itch, dev tools scratch the engineering itch, writing scratches the thinking itch, and a new project from a friend scratches the novelty itch.

Each product serves a psychological function that has nothing to do with business strategy.

And because each one meets a different need, none of them feel dispensable. Killing one doesn't just remove a product from your portfolio. It removes a source of identity and meaning.

This is why the standard advice of "just focus" bounces off most multi-product builders. It's technically correct and psychologically naive. You can't just tell someone to stop doing the thing that makes them feel like themselves.

But you can learn to be honest about which products are serving your business and which ones are serving your ego. That distinction is where the real work lives.

Decision Fatigue Layer

On top of the identity-switching, there's a layer of meta-decisions that drains you before you've done any actual work.

Every morning I sit down and negotiate with myself about what to work on.

• Which product has the most urgent need?
• Which one has the highest potential upside?
• Which one will I regret ignoring?
• Which one am I in the mood for?

That last one is such a trap, it's just avoidance really. You gravitate toward the product that's most fun to work on, which is almost never the one that needs you the most.

I catch myself doing this constantly. Preflight is fun to hack on, writing blog posts is creatively satisfying, creating presets for TheDailyPreset is almost meditative.

So those things get my best hours while the harder, less enjoyable decisions on other products get pushed to the afternoon when my brain is already cooked.

The research on decision fatigue is well-documented. Every choice depletes cognitive resources, and the quality of subsequent decisions deteriorates. Hey, did you know that judges grant parole at significantly higher rates in the morning than in the afternoon?

The decisions don't change, the decision-makers just get tired.

By the time you've decided what to work on, negotiated with yourself about priorities, and context-switched into the right headspace, you've burned through a significant chunk of your best thinking for the day. And you haven't shipped a single thing.

People with one product don't have this problem. They wake up and build the thing, the clarity is automatic, and the energy goes straight into execution instead of allocation. That's an advantage that's invisible until you've experienced the alternative.

Honest Triage

I've tried a lot of systems for managing multiple products. From color-coded calendars to time-blocking, theme days where Monday is photography and Tuesday is dev tools, and even elaborate Notion dashboards tracking progress across everything.

Most of them were sophisticated ways to avoid the actual hard decision, which is admitting that not everything deserves equal attention.

What actually works is ugly and simple. I sort everything into three buckets, and I force myself to do it honestly.

1. The engine

This is the product that generates revenue, has proven distribution, and grows with attention. For me, that's the photography business. DailyPhotoTips and TheDailyPreset together. This gets the most consistent time because the ROI is real and measurable.

It's not always the most exciting work, but excitement is a terrible resource allocation strategy.

2. The bet

This is one product, maybe two if they serve different audiences and don't compete for the same type of energy, that I believe could become the next engine with focused attention.

It has early signals too. Some users, some traction, a thesis I believe in. This gets dedicated blocks of creative time, protected from everything else. The discipline is keeping the number small enough that each bet actually gets the attention density it needs to grow.

Three bets is just another way to spread yourself thin. Two is a compromise I can live with if they pull from different parts of my brain. Right now I'm running two: DailyTips.dev and Hyperfocal. One is a developer newsletter that needs growth and the other is a photography tool that needs positioning and partnerships.

They don't overlap in audience or effort, which is the only reason I'm letting myself make both bets at once.

3. The rest

Everything else gets maintenance mode. Bug fixes if something breaks. Occasional updates if inspiration strikes. But no new creative energy, no ambitious roadmap, no guilt about not doing more. They exist, they run, they don't get my mornings.

Some of these will eventually get promoted to "the bet" if circumstances change. Some will get quietly wound down. But they don't get to pretend they're active projects when they're really just obligations I haven't let go of.

This framework sounds obvious written down. Living it is brutal.

Every time I put something in the maintenance bucket, the endowment effect screams that I'm making a mistake. That this one just needs a little more attention. That the breakthrough is right around the corner if I just give it another month.

It usually isn't. But my brain isn't interested in base rates. It's interested in protecting the things I've built.

The Kill Question

Deciding what to stop is worse than deciding what to work on. Way worse.

I keep coming back to a question I stole from a conversation with another founder: "If I weren't already doing this, would I start it today?"

The answer is clarifying in a way that's deeply uncomfortable.

Some projects I'd absolutely start again. The photography newsletters have proven distribution, proven revenue, and an audience that trusts us. My personal blog is generating exactly the kind of conversations and opportunities I want.

Those are easy.

But others? If someone described them to me at a coffee shop as their new idea, I'd probably nod politely and think "good luck with that." I'm only still running them because I already started. Ugh.

There's a related question that cuts even deeper: "Would I hire someone to run this?" If a product isn't valuable enough to pay someone else to maintain, why is it valuable enough to spend your own time on?

Your time isn't free just because you're not writing yourself a check.

The endowment effect makes this evaluation almost impossible to do honestly without external input. You need someone who isn't emotionally invested in your portfolio to ask you hard questions.

A co-founder, a peer, a mastermind group. Anyone who can look at your lineup and say "why are you still doing that one?" without you getting defensive.

Getting defensive is actually a useful signal. The projects I get most defensive about when questioned are often the ones with the weakest case. If the numbers spoke for themselves, I wouldn't need to defend them.

When Multiple Products Actually Work

I should be honest about the other side of this though.

Sometimes running multiple products is the right call, not just the sentimental one.

It works when the products share distribution.

DailyPhotoTips and TheDailyPreset serve the same audience through the same newsletter infrastructure. Working on one feeds the other and that's a portfolio with synergy, not just a collection of unrelated bets.

Those two also feed into Hyperfocal since, again, the audiences overlap.

It works when you've genuinely exhausted the growth levers on your primary product and additional attention has diminishing returns. If your main thing is running smoothly and growing steadily without constant intervention, the marginal hour might be better spent on something new.

It works when different products create a flywheel between audiences.

DailyTips.dev and my personal blog could theoretically feed each other. Developers who read my blog might subscribe to the newsletter. Newsletter subscribers might read the blog.

And sometimes it works when different products scratch different psychological needs in ways that are genuinely restorative rather than depleting.

The creative energy I bring to writing is different from the operational energy I bring to newsletter management, which is different from the engineering energy I bring to Preflight. Sometimes switching contexts is actually recharging rather than draining, as long as it's intentional rather than reactive.

But these are specific conditions, not blanket justifications.

Most of us aren't honestly evaluating whether our portfolio meets these criteria. We're just afraid to focus because focus means choosing, and choosing means accepting that some things won't get our best.

The Uncomfortable Math

I keep coming back to the same calculation.

If I gave one product my full attention for a year, the way Brett and I gave DailyPhotoTips our attention when it was growing fastest, what would happen?

Something significant would probably happen. The photography business is living proof.

Over a decade of sustained effort turned Contrastly into a brand with over 100,000 subscribers before I sold it. DailyPhotoTips and TheDailyPreset are built on the same principles of showing up and gaining trust over time.

Now compare that to spreading the same effort across seven products for a year. Each one inches forward and none of them ever get past first gear. The portfolio grows linearly while a focused effort would grow exponentially.

Let's make this concrete though.

Say you have 40 productive hours in a week. Split across 7 products, each one gets about 5 to 6 hours.

That's one focused morning per product, if you're lucky. In those 6 hours, you can respond to some emails, fix a bug, maybe write a draft of something. You cannot do deep creative work, build meaningful features, or create the kind of content that actually accumulates into something.

Now give one product 30 of those hours and let the rest share the remaining 10 for basic maintenance. In 30 focused hours, you can ship a major feature, write three pieces of content, build a partnership, redesign an onboarding flow, and still have time to think strategically about where the product is going.

Damn, now we're talking!

6 scattered hours versus 30 focused hours doesn't produce 5x the output. It's closer to 20x, because deep work produces exponentially better results than shallow work.

Cal Newport's research on this is pretty well-established at this point. The ability to perform deep work is becoming increasingly rare and increasingly valuable.

Every product you add to your portfolio doesn't just divide your time. It divides the quality of your time.

The Guilt Economy

There's one more psychological dimension to this that I haven't seen anyone write about honestly. Every product in your portfolio generates guilt when you're not working on it.

Right now, as I write this article, Preflight needs a SaaS layer built on top of the open source CLI. DailyTips.dev is brand new and needs to grow faster. Hyperfocal needs better positioning and affiliate partnerships. BestAIThings needs infrastructure work and a strategy for the future.

Each of these represents a small, persistent weight. Individually manageable, but collectively crushing.

The guilt operates in the background like a resource-hungry app draining your battery. You're not actively thinking about the neglected products, but they're pulling at your attention, creating a low-grade anxiety that makes it harder to be fully present on whatever you are working on.

The insidious part is that the guilt feels productive. "I should be working on that other thing" feels like conscientiousness, like caring about your work. But it's actually sabotaging the work you're doing right now by splitting your attention between the present task and the imagined obligations of five other products.

The only cure for portfolio guilt is permission.

Permission to let things sit or to respond to that GitHub issue tomorrow, or next week, or never. Permission to acknowledge that a product in maintenance mode will survive without your constant attention.

This is harder than it sounds for people who built their identity around being responsive and present. But the alternative is being partially present on everything, which serves nobody.

Least of all yourself.

What I'm Actually Going to Do About It

I don't want to end this article with clean advice that sounds good and changes nothing. I've read too many pieces like that.

So here's what I'm actually going to do, written down publicly so I can't pretend I didn't say it.

I'm making two bets.

DailyTips.dev and Hyperfocal. I'm aware that earlier in this article I argued for keeping the number as small as possible, and two is already pushing it. But they serve completely different audiences and require different types of work, and I'd rather be honest about what I'm actually doing than write a cleaner narrative that I abandon by next week.

The photography business keeps running as the engine. It's earned that through over a decade of work.

My personal blog keeps going because this writing is what feeds everything else. It's how I think, how I build credibility, and how I connect with people who might eventually care about whatever I'm building. Not stopping is the whole game.

Everything else gets honest evaluation against the kill question.

If I wouldn't start it today, I need to either find a reason to keep it that goes beyond sunk cost, or let it go.

The endowment effect will tell me they all deserve attention. The math says most of them don't. 2 bets, not 7. That's the line I'm drawing, publicly, so I can't pretend I didn't say it.

The second product problem has almost nothing to do with the second product. The real problem is the story we tell ourselves to avoid the terrifying simplicity of focus.

It's easier to be busy across 7 things than to be committed to one, because commitment means the results are yours to own entirely. No diversification to hide behind. No "well, I was also working on these other things" to explain away a disappointing outcome.

The products that win are usually the ones whose builders could tolerate focusing on them long enough for growth to kick in.

I've proven I can do that once. Now I have to prove I can do it again, without the safety net of 6 other things to catch me if it doesn't work.

Time to pick.