Love Your Work

In raw numbers, I've made a "profit" on the podcast. But, as I broke down in my latest income report, my "wage" was about $6 an hour. My podcast comprised about 5% of my income over these eight years, and took much more than that portion of my time and energy.

Of course, I don't think about whether the podcast was worth it in terms of an hourly rate. Creative work happens in Extremistan, not Mediocristan, and I've made massive life choices to be free to explore creatively without worrying so much what I'm earning in the short-term.

But there are many different ways to make a podcast a solid business, and none of them worked for me, for various reasons.

Here are some of these business models, as they apply to the "thought-leader" space (I'll ignore the more entertainment/infotainment space that podcasts like Gimlet's inhabit).

1. Be so massively famous, you can pick-and-choose advertisers, while demanding a lot of money. This is where Tim Ferriss and Joe Rogan are. They both started with large platforms, and applied whatever talents that helped them earn those platforms to make their podcasts huge. After more than fifteen years as a creator, I have a modest platform, but orders of magnitude smaller.
2. Build a "content machine" that manufactures ad slots. I won't name names, but you've heard these podcasts. They're formulaic and don't seem to discern much who they have as a guest, nor what sponsors they accept. This business model is why my inbox is still full of pitches – they think I actually want more guests, because more guests would mean more ad slots. It takes a very rare set of circumstances for me to be excited to interview someone.
3. Share information that directly helps people make money. If you have tactical and actionable information that's useful to professionals in a specific industry, you can charge for premium podcast content. I'm not as interested in the tactical and actionable as I am in the abstract and exploratory.
4. Cover a niche topic. If you have a leading podcast about a very specific topic, advertisers within that niche will be willing to pay high rates to reach that audience. I didn't want to build my podcast according to a specific topic – more on that later.
5. Have a "back-end" business. If you have a thriving consulting business, or training programs to sell, you can attract more clients and customers through your podcast. As I wrote in my ten-year reflections, "I want to make a living creating. I don't want creating to be merely a marketing strategy for other things. Is that completely insane?"

I flirted with success in a few of these business models. Early on, I hoped my podcast would be famous enough to pick and choose advertisers at high rates. For a while, it looked like I had a chance. I was approached by a podcast network, and I had some reputable advertisers such as LinkedIn, Skillshare, Casper, Audible, Pittney Bowes, and University of California. Various times, I thought I was on the cusp of my "big break" – such as when Love Your Work was featured on the Apple Podcasts home screen.

But the more I tried to go the "get famous" route, the louder the siren-song of the "content machine" route got. There were plenty of opportunities to do "interview swaps" with hosts I wasn't interested in interviewing. There were a few advertisers that had money, but whose products felt sleazy. Joining a podcast network would have pressured me to crank out content even if I didn't feel like it. There was (and still is) the never-ending stream of pitch emails for guests. I had too much wax in my ears to go the "content machine" route.

Not included in my lifetime revenue-estimates for Love Your Work is money I made through the "back-end business" route. I was somewhat comfortable with this model, but I haven't made a course in years, as I've been focused on writing books. And as bad a business as people say writing books is, it's better than making a podcast.

The podcast has helped me sell books in more ways than one. One way is that people who listened to the podcast bought my books. The other way is, making my podcast helped me write my books.

This brings me to the reason I kept making my podcast, even after I realized it wasn't a good business.

In my sixteen years experimenting with different business models as an independent creator, I've settled on one thing that works: Make for what making makes you.

If making a podcast, writing a book, sending a weekly newsletter – you name it – merely makes you money, and doesn't make you who you want to be, what's the point?

Sure, sometimes you don't feel like creating, and you do it anyway. Yes, sometimes you pick one project over another because you think it will be more lucrative. But you can only redirect the river that is your creativity so much before it overflows and returns to its natural path.

When I started Love Your Work, and was struggling to make it big enough to work with an ad model, even if I wasn't bringing in lots of ad revenue, I was still connecting with and learning from my guests. It was an incredible privilege to have in-depth conversations with people like Seth Godin, Elise Bauer, and David Allen. It was like having my own personal advisory board of heroes.

Talking to them helped me learn how to go off the beaten path and find my calling. I was able to find patterns in their stories that I could apply to my own life and career. I would be a completely different person today if I hadn't had those conversations.

But there came a point when doing interviews was no longer serving me the way it once had. It was when I had gained the confidence – thanks to my previous guests – to explore further my own ideas.

That's when I stopped interviewing guests, so I'd have more time to explore. Love Your Work shifted from my personal advisory board to my personal sounding board – a sort of "open mic," where I fleshed out ideas. I got to see how it felt to effortfully explore each idea. I got to hear how they sounded when I read them aloud. I got to feel how they resonated (or didn't) with others.

A couple years after I started Love Your Work, I started writing a book called Getting Art Done. Getting Art Done turned out to be three books, two of which I've published. Love Your Work has been there to help me explore the ideas in these books. The Heart to Start was full of conversations from my early guests, and came from my very real struggles in gaining the confidence to take my ideas seriously enough to pursue them. Mind Management, Not Time Management came from my very real struggles to harness my creative energy and push my ideas forward.

As I work on the final book in the Getting Art Done trilogy, Finish What Matters, I'm asking myself, What struggle does this book come from? Clearly, I've finished a lot of creative work: three books, over two-hundred consecutive weekly newsletters, and over three-hundred episodes of this podcast. But as I've dwelt on that final word in the title, matters, I'm asking myself if I'm really working on what matters?

Love Your Work and Getting Art Done have been an exploration in creative productivity. But at some point, writing about Resistance becomes a form of Resistance. I don't feel I've reached that point yet, but I don't want to. If I'm going to learn enough to write Finish What Matters, I have to really test my ideas of what matters.

I've probably explored enough ideas, through Love Your Work, that I want to develop further in Finish What Matters. But for the time being, I need space to explore what matters. That's the biggest reason I'm quitting Love Your Work. I had considered doing so in the past, but I kept hoping I'd know What's Next before I quit. I've come to realize that I can't know What's Next until I have the space to explore.

It's a little scary to have that void. But it's also exciting. Furthermore, I've faced The Void many times before: when I started on my own, after finishing each book, and a little bit after each podcast episode or newsletter. What's scarier now than facing the void is that I'll stick with what's safe, and distract myself into dying with my best creations inside me.

I could just say I'm taking a break, or not say anything at all and stop until I felt inspired to make a new episode. I've talked before about how I struggle to burn my boats and close doors. So, I'm calling it quits, knowing I could always drop another episode in the feed down the line if I wanted to. But I hope I find something that matters more, before that ever happens.

Thank you for listening to Love Your Work. Thank you especially to my Patreon supporters, who can of course feel free to stop supporting, or keep supporting for the bonus content, and to support What's Next. To learn What's Next once I find it, be sure to subscribe to my newsletter at kdv.co.

One last time, thank you. Thank you, thank you, thank you.

Image: Pierrot Lunaire by Paul Klee

David Kadavy is author of Mind Management, Not Time Management, The Heart to Start and Design for Hackers. Through the Love Your Work podcast, his Love Mondays newsletter, and self-publishing coaching David helps you make it as a creative.

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Show notes: https://kadavy.net/blog/posts/quit-podcasting/

I was in Rome last month, visiting some Raphael paintings to research my next book, and stopped by the Sistine Chapel.

I've spent a good amount of time studying what Michelangelo painted on that ceiling. There are lots of high-resolution images on Wikipedia.

But seeing a picture is nothing like the experience of seeing the Sistine Chapel. You've invested thousands of dollars and spent fifteen hours on planes. You're jet-lagged and your feet ache from walking 20,000 steps. You're hot.

When you enter, guards order you to keep moving, so you won't block the door. They corral you to the center, and you can finally look up.

When you hear wine experts can't tell between white and red wine, you imagine the following: Professional sommeliers are blindfolded, and directed to taste two wines. They then make an informed guess which is white, and which is red. In this imaginary scenario, they get it right half the time – as well as if they had flipped a coin.

If it were true wine experts couldn't tell between white and red wine, the implication would be that the experience of tasting wine is separate from other aspects of the wine. That the color, the shape of the glass, the bottle, the label, and even the price of the wine are all insignificant. That they all distract from the only thing that matters: the taste of the wine.

There's some psychophysiological trigger that gets pulled when you tilt your head back. Maybe it stimulates your pituitary gland. When you have your head back and are taking in the images on the Sistine Chapel ceiling, you feel vulnerable. (You literally are vulnerable. You can't see what's going on around you. You'd be easy to physically attack.)

What you see is overwhelming. As you try to focus your attention on some detail, some other portion of the imagery calls out and redirects your attention. This happens again and again.

After a while, your neck needs a rest, and you return your gaze to eye-level. And this is almost as cool as the ceiling: You see other people with their heads back, their eyes wide, mouths agape, hands on hearts, tears in eyes. You hear languages and see faces from all over the world. You realize they all, too, have invested thousands of dollars and spent fifteen hours on planes. They, too, are jet-lagged and hot and have walked 20,000 steps.

You can look at pictures of the Sistine Chapel ceiling on the internet. You can experience it in VR. In many ways, this is better than going to the Sistine Chapel. You can take as much time as you want, and look as close as you want. You don't have to spend thousands of dollars and fifteen hours on a plane, take time off work, or even crane back your neck.

But seeing the Sistine Chapel ceiling on the internet or even VR is only better than seeing it in person, in the way that a spoonful of granulated sugar when you're starving is better than a hypothetical burger in another iteration of the multiverse.

We've seen an explosion of AI capabilities in recent months. That has a lot of people worried about what it means to be a creator. Why do we need humans to write, for example, if ChatGPT can write?

The reason ChatGPT's writing is impressive is the same reason there's still a place for things created by humans.

Anyone old enough to have been on the internet in the heyday of America Online in the 1990s will remember this: When you were in a chat room, most the conversations were about being in a chat room: How long have you been on the internet? Isn't the internet cool? What other chat rooms do you like? Part of the appeal of the question "ASL?" – Age, Sex, Location? – was marveling over the fact you were chatting in real-time with a stranger several states away.

Or maybe you remember when Uber or Lyft first came to your town. For the first year or two, likely every conversation you had with a driver was about how long they had been driving, about how quickly the service had grown in your town, which is better – Uber or Lyft?, or which nearby cities got which services first.

The first few months ChatGPT was out, it was seemingly the only thing anyone on the internet talked about. But it wasn't because ChatGPT's writing was amazing. ChatGPT is a bad writer's idea of a good writer. It was because of the story: Wow, my computer is writing!

Now that much of the novelty of ChatGPT has worn off, many of us are falling into the Trough of Disillusionment on the Gartner Hype Cycle. We're realizing ChatGPT is like a talking dog: It's impressive the dog can appear to talk, but it's not talking – it's just saying the words it's been taught. ChatGPT is very useful in some situations, but not as many as we had originally hoped.

What made us talk about the internet while on the internet, talk about Uber while in Ubers, and talk about ChatGPT while chatting with ChatGPT was the story. Once the story behind the internet or Uber wore off, we started to appreciate them for their own utility.

Part of what's cool about seeing the Sistine Chapel ceiling in VR is that – we're seeing it in VR. But even if that weren't impressive, what would still be impressive about the paintings would be more than just that they're amazing paintings. It's incredible to us a human could paint such a massive expanse. We think about the stories and myths of Michelangelo, up on that scaffolding, painting in isolation. Part of our appreciation of the Sistine Chapel ceiling lies outside the ceiling itself. While marveling at it, we can't help but think of Michelangelo's other masterpieces, such as the David or the Pietà.

Lloyd Richards spent fourteen years writing Stone Maidens, and had almost no sales for decades. Suddenly, he sold 65,000 copies in a month. He was interviewed on the TODAY show, and got a book deal with a major publisher.

How did he do it? His daughter made a TikTok account. The first video showed Lloyd at his desk, and explained what a good dad he was, how hard he had worked on Stone Maidens, and how great it would be if he made some sales. Then the #BookTok community did the rest.

Stone Maidens is apparently a good book. But it's no better today than it was all those years it didn't sell. Most the comments on Lloyd's TikTok account – which now has over 400,000 followers – aren't about what a great book Stone Maidens is. They're about how Lloyd seems like such a nice guy, or how excited each commenter is to have contributed to his success.

The study that started the myth that wine experts can't taste the difference between white and red wine didn't show that. The participants in the study literally weren't allowed to describe the two wines the same way – they couldn't use the same word for one as the other. It wasn't blindfolded – it was a white wine versus the same wine, dyed red. The study wasn't about taste at all: Participants weren't allowed to taste the wine – they were only allowed to smell. And wine experts? That depends on your definition of "expert". They were undergraduate students, studying wine. They knew more than most of us, but were far from the top echelon of wine professionals. Most damning for this myth was that the same study casually mentions doing an informal blind test: The success rate of their participants in distinguishing the taste of white versus red wine: 70%.

That this myth is false shouldn't detract from the point that even if it were true, it wouldn't matter. What the authors of this study found was not that wine enthusiasts couldn't tell between white and red wine, but that the appearance of a wine as white or red shaped their perceptions of the smell of the wine.

Once you bake a cake, you can't turn it back into flour, sugar, butter, and eggs. You can't extract the taste of a wine from the color, the bottle, your mental image of where the grapes were grown and how the wine was made, or even the occasion for which you bought the wine. Something made by an AI can be awesome, either because it's really good at doing what it's supposed to, or because you appreciate it was made by an AI. Something made by a human is often awesome because of the story of the human who made it, and the story you as a human live as you interact with it.

If you want to be relevant in the age of AI, learn how to bake your story into the product. Because AI can't bake.

Image: Figures on a Beach by Louis Marcoussis

David Kadavy is author of Mind Management, Not Time Management, The Heart to Start and Design for Hackers. Through the Love Your Work podcast, his Love Mondays newsletter, and self-publishing coaching David helps you make it as a creative.

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Show notes: https://kadavy.net/blog/posts/ai-cant-bake/

In Isaiah Berlin's 1953 essay, "The Hedgehog and the Fox," he quotes the ancient Greek poet, Archilochus:

The fox knows many things, but the hedgehog knows one thing.

Berlin describes this as "one of the deepest differences which divide writers and thinkers, and, it may be, human beings in general."

According to Berlin, hedgehogs relate everything to a single central vision. Foxes pursue many ends, often unrelated or even contradictory.

If you're a hedgehog, you explain the world through a focused belief or area of expertise. Maybe you're a chemist, and you see everything as chemical reactions. Maybe you're highly religious, and everything is "God's will."

If you're a fox, you explain the world through a variety of lenses. You may try on conflicting beliefs for size, or use your knowledge in a wide variety of fields to understand the world. You explain things as From this perspective, X. But on the other hand, Y. It's also worth considering Z.

Even though this dichotomy Berlin presented has spread far and wide, his essay is mostly about Leo Tolstoy, and the tension between his fox-like tendencies and hedgehog-like aspirations. In Tolstoy's War and Peace, he writes:

In historic events the so-called great men are labels giving names to events, and like labels they have but the smallest connection with the event itself. Every act of theirs, which appears to them an act of their own will, is in an historical sense involuntary and is related to the whole course of history and predestined from eternity.

In War and Peace, Tolstoy presents characters who act as if they have control over the events of history. In Tolstoy's view, the events that make history are too complex to be controlled. Extending this theory outside historical events, Tolstoy also writes:

When an apple has ripened and falls, why does it fall? Because of its attraction to the earth, because its stalk withers, because it is dried by the sun, because it grows heavier, because the wind shakes it, or because the boy standing below wants to eat it? Nothing is the cause. All this is only the coincidence of conditions in which all vital organic and elemental events occur.

Is Tolstoy a fox, or a hedgehog? He acknowledges the complexity with which various events are linked – which is very fox-like. But he also seems convinced these events are so integrated with one another that nothing can change them. They're "predetermined" – a "coincidence of conditions."

A true hedgehog might have a simple explanation, such as that gravity caused the apple to fall. Tolstoy loved concrete facts and causes, such as the pull of gravity, yet still yearned to find some universal law that could be used to predict the future.

According to Berlin:

It is not merely that the fox knows many things. The fox accepts that he can only know many things and that the unity of reality must escape his grasp.

And this was Tolstoy's downfall. Early in his life, he presented profound insights about the world through novels such as War and Peace and Anna Karenina. That was very fox-like. Later in his life, he struggled to condense his deep knowledge about the world and human behavior into overarching theories about moral and ethical issues. As Berlin once wrote to a friend, Tolstoy was "a fox who terribly believed in hedgehogs and wished to vivisect himself into one."

Other thinkers Berlin classifies as foxes include Aristotle, Goethe, and Shakespeare. Other thinkers Berlin classifies as hedgehogs include Dante, Dostoevsky, and Plato.

What does knowing many things have to do with actual foxes? What does knowing one big thing have to do with actual hedgehogs? A fox is nimble and clever. It can run fast, climb trees, dig holes, swim across rivers, stalk prey, or hide from predators. A hedgehog mostly relies upon its ability to roll into a ball and ward off intruders.

What are the consequences of being a fox or a hedgehog? According to Phil Tetlock, foxes are better at telling the future, while hedgehogs get more credit for telling the future.

In Tetlock's 2005 book, Expert Political Judgement, he shared his findings from forecasting tournaments he held in the 1980s and 90s. Experts made 30,000 predictions about political events such as wars, economic growth, and election results. Then Tetlock tracked the performances of those predictions.

What he found led to the U.S. intelligence community holding forecasting tournaments, tracking more than one million forecasts. Tetlock's own Good Judgement Project won the forecasting tournament, outperforming even intelligence analysts with access to classified data.

These forecasting tournaments have shown that whether someone can make accurate predictions about the future doesn't depend upon their field of expertise, their status within the field, their political affiliation, or philosophical beliefs. It doesn't matter if you're a political scientist, a journalist, a historian, or have experience implementing policies. As the intelligence community's forecasting tournaments have shown, it doesn't even matter if you have access to classified information.

What matters is your style of reasoning: Foxes make more accurate predictions than hedgehogs.

Across the board, experts were barely better than chance at predicting what would or wouldn't happen. Will a new tax plan spur or slow the economy? Will the Cold War end? Will Iran run a nuclear test? Generally, it didn't matter if they were an economist, an expert on the Soviet Union, or a political scientist. That didn't guarantee they'd be better than chance at predicting what would happen. What did matter is whether they thought like a fox.

Foxes are skeptical of grand schemes – the sort of "theories of everything" Tolstoy had hoped to construct. They didn't see predicting events as a top-down, deductive process. They saw it as a bottom-up, inductive process – stitching together diverse and conflicting sources of information.

Foxes were curious and open-minded. They didn't go with the tribe. A liberal fox would be more open to thinking the Cold War could have gone on longer with a second Carter administration. A conservative fox would be more open to believing the Cold War could have ended just as quickly under Carter as it did under Reagan.

Foxes were less prone to hindsight bias – less likely to remember their inaccurate predictions as accurate. They were less prone to the bias of cognitive conservatism – maintaining their beliefs after making an inaccurate prediction. As one fox said:

Whenever I start to feel certain I am right... a little voice inside tells me to start worrying. —A "fox"

As for inaccurate predictions, one simple test tracked with whether an expert made accurate predictions: a Google search. If an expert was more famous – as evinced by having more results show up on Google when searching their name – they tended to be less accurate.

Think about the talking-head people that get called onto MSNBC or Fox News (pun, albeit inaccurate, not intended) to make quick comments on the economy, wars, and elections – those people. Experts who made more media appearances, and got more gigs consulting with governments and businesses, were actually less accurate at making predictions than their colleagues who were toiling in obscurity. And these experts who were more successful – in terms of media appearances and consulting gigs – also tended to be hedgehogs.

Hedgehogs see making predictions as a top-down deductive process. They're more likely to make sweeping generalizations. They take the "one big thing" they know – say, being an expert on the Soviet Union – and view everything through that lens. Even if it's to explain something in other domains.

Hedgehogs are more-biased about the world, and about themselves. They were more likely than foxes to remember inaccurate predictions they had made, as accurate. They were more likely to remember as inaccurate, predictions their opponents made that were accurate. Rather than change their beliefs, when presented with challenging evidence hedgehog's beliefs got stronger.

It's tempting to take that and run with it: The close-minded hedgehogs of the world are inaccurate. Success doesn't track with skill. Tetlock is careful to caution that hedgehogs aren't always worse than foxes at telling the future. Also, there are good reasons to be overconfident in predictions. As one hedgehog political pundit wrote to Tetlock:

You play a publish-or-perish game run by the rules of social science.... You are under the misapprehension that I play the same game. I don't. I fight to preserve my reputation in a cutthroat adversarial culture. I woo dumb-ass reporters who want glib sound bites. —"Hedgehog" political pundit

A hedgehog has a lot to gain from making bold predictions and being right, and nobody holds them accountable when they're wrong. But according to Tetlock, nothing in the data indicates hedgehogs and foxes are equally good forecasters who merely have different tastes for under- and over-prediction. As Tetlock says:

Quantitative and qualitative methods converge on a common conclusion: foxes have better judgement than hedgehogs. —Phil Tetlock, Expert Political Judgement

As bad as hedgehogs look now, there are some real benefits to hedgehogs. They're more-focused. They don't get as distracted when a situation is ambiguous. So, hedgehogs are more decisive. They're harder to manipulate in a negotiation, and more willing to make controversial decisions that could make enemies. And that confidence can help them lead others.

Overall, hedgehogs are better at getting their messages heard. Given the mechanics of media today, that means the messages we hear from either side of the political spectrum are those of the hedgehogs. Hedgehog thinking makes better sound bites, satisfies the human desire for clarity and certainty, and is easier for algorithms to categorize and distribute. The medium is the message, and nuance is cut out of the messages by the characteristics of the mediums. Which increases polarization.

But, there is hope for the foxes. While the media landscape is still dominated by hedgehog messages that work as social media clips, there are more channels with more room for intellectually-honest discourse: blogs, podcasts, and books. And if many a ChatGPT conversation is any indication, the algorithms may get more sophisticated and remind us, "it's important to consider...."

If you're a hedgehog, you're lucky: What you have to say has a better chance of being heard. But it will have a better chance of being correct if you think like a fox once in a while: consider different angles, and assume you're wrong.

If you're a fox, you have your work cut out for you: You may have important – and accurate – things to say, but they have less a chance of being heard. Your message will travel farther if you think like a hedgehog once in a while: assume you're right, cut out the asides, and say it with confidence.

Image: Fox in the Reeds by Ohara Koson

David Kadavy is author of Mind Management, Not Time Management, The Heart to Start and Design for Hackers. Through the Love Your Work podcast, his Love Mondays newsletter, and self-publishing coaching David helps you make it as a creative.

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Show notes: https://kadavy.net/blog/posts/hedgehogs-foxes/

I've experienced, "too many ideas, must pick one," many times. I still often do. I of course answered this question in the AMA, but here I'll answer more in-depth. This is the thought process I guide myself through when I'm in the land of "too many ideas, must pick one."

There are three assumptions embedded in, "too many ideas, must pick one."

1. All these ideas are equally likely to succeed.
2. I'm equally capable of succeeding at each of these ideas.
3. I can't work on multiple ideas at once.

Let's look at each of those.

If you feel you have too many ideas, you must think they're equally likely to succeed, which is the first assumption. That might not sound correct at first, but think about it. If you were starving, and only allowed to eat one of various sandwiches, you would probably pick the biggest and most calorie-rich.

You might not be able to tell so easily which is the biggest and most calorie-rich sandwich. In fact, there may be other factors that play into your decision. Maybe the avocado and pork belly sandwich is the most calorie-rich, but you're craving roasted duck in this moment, and there happens to be a roasted-duck sandwich amongst the selections.

While satisfying your hunger is one objective of choosing a sandwich, there are other goals in mind, such as satisfying cravings, which may compete with one another. If you have a hard time deciding amongst all the sandwiches, you expect eating one sandwich to be equally likely to succeed as eating any of the others.

As with projects, "success" may come in many forms. We'll get to that in a bit.

If you feel you have too many ideas, you must think you're equally capable of succeeding at each of these ideas, which is the second assumption. If assumption one weren't correct, and you didn't feel each idea were equally likely to succeed, you would probably pick the one most likely to succeed. The avocado and pork belly sandwich would clearly be more filling than peanut butter and jelly.

Now, if you weren't equally capable of eating each of the sandwiches, that would make your decision easier. If you're choosing between avocado and pork belly and peanut butter and jelly, but you're a strict vegetarian, the decision is easy. Same if you're not a vegetarian, but allergic to peanuts.

But since you feel each idea is equally likely to succeed, and you feel you're equally capable of succeeding at all of them, you feel you have too many ideas.

As with projects, you may have little information about your capability of succeeding, which is why, for all you know, your capability to succeed is equal across all ideas. We'll untangle that later.

If you feel you have "too many ideas," you feel they're equally likely to succeed and you're equally capable of succeeding at each of them. If you feel you "must pick one," you feel you can't work on multiple ideas at once, which is the third assumption.

In our sandwich scenario, you've been told you have to pick one sandwich. If there's no one else around and the sandwiches will go to waste otherwise, you might as well taste all the sandwiches, then pick one. Or eat a little of each, until you're full. But, in that case, you wouldn't finish any of the sandwiches.

With all three of these assumptions, you're in a deadlock. Your ideas are equally likely to succeed, you're equally capable of succeeding at each, and you must pick one. Well, how can you pick one if they're all equally appealing ideas?

There are five questions that can help you challenge these assumptions:

1. What is success?
2. What is my risk profile?
3. What am I good at?
4. What's necessary to succeed?
5. What pain do I pick?

Let's look at each of these.

Success can come in many forms. Maybe you want to make the most money possible. Maybe you want the most freedom possible. Maybe you want to do what you're most passionate about.

You may feel each idea is equally likely to succeed, because each idea is likely to get a different kind of success. One sandwich will fill you up, another will taste great, still another seems like the healthy choice.

If you have a clearer picture of what forms of success are more important to you than others, your many ideas will no longer be "equally likely to succeed."

Not only can success come in many forms, it can come with various risk profiles. One idea may have a big chance of bringing you mild success. Another idea may have a small chance of bringing you wild success. The overall expected value of each idea may be the same, but the risk profiles may be very different. Some are sure bets, some are wildcards.

There are also various things you may risk in pursuing an idea. Mostly, what I call "TOM" – Time, Optionality, and Money. If you are young, healthy, and with no commitments, you have a lot of Optionality, but you might not have much Money. Making enough Money to live may take up much of your day-to-day Time. You can try a crazy idea, so long as it doesn't take up too much Time and Money. If you fail, you'll still have plenty of Optionality.

Or, you might want to make some changes that reduce your Optionality, but free up your Time. For example, I live in South America, which limits my options for anything requiring physical presence, but it has reduced my need for Money, thus freeing up my Time.

On the other hand, you may be in your sixties, retired after a successful career. You have plenty of Money and Time, but less Optionality than when you were in your twenties. You can only take on so many big projects in the rest of your life, and you may not have the energy you used to. But, you may feel you have nothing to lose by trying a wild idea.

If you have a clearer picture of what your risk profile is, not all your ideas will seem "equally likely to succeed."

Even if all your ideas seem equally likely to fit your definition of success and fit your risk profile, you're probably better at some things than others.

If you have a clear picture of what you're good at, the assumption that you're "equally capable of succeeding at each of these ideas" will no longer make sense.

It may be that you don't know what you're good at, likely because you don't feel you have information to tell you what you're good at. You probably have more information available than you think. Think about times in the past when someone was impressed with or complimented you on something you did, which came to you naturally. Or, ask your friends what they think you're good at.

If you really don't have information on what you're good at, relative to your many ideas, then the third assumption, "I can't work on multiple ideas at once," no longer makes sense. In this case, you can and should work on multiple ideas, to get an idea what you're good at. If you feel your ideas are too big to work on more than one, scale them back into smaller ideas. Don't fall for "The Fortress Fallacy," like I talked about in The Heart to Start. Instead of building a fortress, try building a cottage.

It's important to remember that what you're good at is not necessarily what you're best at, nor what you most enjoy. This will make more sense as we answer the last two questions that challenge the three assumptions.

In reality, you probably don't have a clear picture of how likely all your ideas are to succeed, nor how capable you are of succeeding at each. You have to ask of each, What's necessary to succeed?

What's necessary to succeed at an idea is usually very different from what attracts you to the idea in the first place. You may love to play music. You may even love to play music in front of an audience. But will you love driving around the country, sleeping in a van, lugging gear, and dealing with curmudgeonly AV techs at each venue? You may love the idea of signing books for adoring fans at the local Barnes & Noble. But will you love sitting in a room by yourself, writing several hours a day?

It's worth noting that what most people in a domain think is necessary to succeed may not be. Lots can change in the industry, and changes in the mechanics of media can open up opportunities to succeed without doing some things that were once necessary. For example, thanks to self-publishing, I don't have to write boring book proposals or get countless rejection letters to succeed as an author.

You may be really good at what's necessary to succeed at an idea that has a good chance of meeting your definition of success. But there may be some things necessary to succeed that you don't enjoy. That doesn't mean you shouldn't pursue the idea.

No matter what you do, there will be some parts of it you aren't crazy about – especially at first. When I was a kid, all I wanted to do was draw. But making a living at drawing as an adult doesn't fit my risk profile, and what's necessary to succeed would interfere with parts of my definition of success: I can't travel if I have to lug around supplies and artwork, and if I do all my work on a computer, then I'm chained to a computer.

I didn't used to like to write, but I found out I'm reasonably good at it. Forcing myself to write each morning was painful at first, but through building a writing habit, it's transformed into a strangely enjoyable sort of pain.

Additionally, there are parts of making a living writing that I don't like, or at least didn't at first. My first one-star review shook me for days, but now I can brush them off relatively quickly. Same with angry emails from readers. I used to really hate bookkeeping, but now that I write monthly income reports, I actually look forward to tallying up my earnings.

After all this, you may realize you don't have "too many ideas," and you don't really have to "pick one." If you don't feel you have enough information to form a clear picture of the odds of success and your capability of success, even after asking these five questions, then you need more information.

You get more information not by choosing one idea, but by pursuing many. You'll more clearly see what has a chance of succeeding and what you're capable of succeeding at, and choosing one – or several – will become easy.

Image: Stage Landscape by Paul Klee

David Kadavy is author of Mind Management, Not Time Management, The Heart to Start and Design for Hackers. Through the Love Your Work podcast, his Love Mondays newsletter, and self-publishing coaching David helps you make it as a creative.

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Show notes: https://kadavy.net/blog/posts/too-many-ideas/

Today I have a special episode for you. If you missed last month's AMA/Livestream, I'm delivering it right to your ears. In this AMA, I answered questions about:

• What's the best self-publishing platform, and how did I publish 100-Word Writing Habit, non standard-sized, outside of Amazon?
• Buenos Aires versus Medellín, which is better for mind management?
• How to pick a creative project when you have too many ideas?
• What's surprised me most in the past two years?
• What task management software do I use for mind management?
• How to focus on one project when you have multiple curiosities?
• How to keep from falling down a research rabbit-hole?
• How many half-formed ideas do I have captured somewhere?

There are some parts where I refer to visuals, for the best experience, watch on YouTube.

David Kadavy is author of Mind Management, Not Time Management, The Heart to Start and Design for Hackers. Through the Love Your Work podcast, his Love Mondays newsletter, and self-publishing coaching David helps you make it as a creative.

Follow David on:

• Twitter
• Instagram
• Facebook
• YouTube

• Apple Podcasts
• Overcast
• Spotify
• Stitcher
• YouTube
• RSS
• Email

I've been adding lots of new content to Patreon. Join the Patreon »

Show notes: http://kadavy.net/blog/posts/four-sources-of-shiny-object-syndrome/