156: 8 Idea Generation Strategies
8 Dec 2025 · 24 min
Jenny Blake shares eight ways to generate content ideas when inspiration is low. Keep a collection bucket for random thoughts, capture personal stories while they're fresh, ask your audience questions, combine ideas in new ways, take contrarian angles on trends, challenge common quotes, spot emerging signals, and write a love letter to who you're making for.
Questions this episode answers
January 10 (recording date mentioned in episode).
January 20, 2023.
Chapters
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
I had such high hopes for that magical two weeks after the holidays, after I had traveled to see Family of deep rest and reflection, thinking about the New Year. And then bam. The day I got home I got hit with another terrible cold. I tested negative for Covid, but I was completely laid flat. That marked the third time in practically as many months. There was an article in the newspaper that said New Yorkers are sick of being sick and I get a little wary of this marketing around the triple demic, but nonetheless I had had a personal triple demic crisis of my own because the week of Thanksgiving I was completely laid out. I won't even say burnt out, I just couldn't work. Then I got a really bad cold and my immune system must have been down because after that trip slammed again and that third time I couldn't smell or taste again. Even though I tested negative for Covid, which to date I still don't even know if I've had it. I haven't had that antibody test. This is a long way of telling you that I am just coming out of that. I recording this today on January 10th, 10 days before this episode will go live. I have not officially kicked off my work year yet that will start tomorrow on January 11th. So I did a good job of keeping a very clear schedule, thank goodness. But I've had so many people ask, oh, what are your goals for the first quarter? What are your goals for the year? What reflection exercises have you been doing? What are you most excited about? And I was so sick over New Year's Eve, New Year's Day, and then just recovering and trying to bounce back and get to any sort of semblance of normal feeling and thinking that I don't have any good answers. So when I knew that I was coming in to record this episode, once again, I found myself in a position of feeling a little bit blah or meh. What am I gonna record? What am I gonna talk about? Any of you who produce content regularly can relate, whether it's a newsletter, writing articles, podcasting, whatever your format. If you see creating content as an important part of putting yourself out there and building your business, then I know you can relate. This is my 18th year of trying to semi regularly put things out in public. What I call ongoing public original thinking. And you better believe that in those 18 years I have major dips, especially coming out of a cold and in the cold here in New York. But coming out of a cold and just having that reduced energy and reduced sense of inspiration, reduced sense of being in any sort of flow at all, I need to then lean on some surefire strategies when it's time to record. As I've shared in previous episodes on accountability, when I know that I have solo episodes due to the production team, I'm accountable to the team. And then I also book recording space in New York. So that also keeps me accountable because I've paid for that space and I don't want to cancel. I don't want to fritter away the time once I get into the studio. Today I'm sharing eight of my Go to Strategies for Idea Generation. And before we start, I want to say thank you. Because in a meta example, the idea for this episode came from those of you who downloaded OR accessed the FreeTime toolkit and said that one of the things if I could wave a magic wand and help you, it would be with idea generation. So I'm taking my own advice, a little bit of my own medicine here that gave me the idea to create this episode for you and win. Win. If you want to check out the FreeTime Toolkit and you haven't already, visit itsfreetime.com Toolkit. That's itsfreetime.com ToolKit. Let's dive in.
Strategy number one. You've heard me talk about this many times now. Create a collection bucket. I did a walkthrough with Cal Newport for this. We'll put a link in the show notes once it goes live on his end because this was for his community. It was in response to him saying that he has good collection systems for when he's working on a book or an article, but not necessarily for anything that comes in outside of a specific scope or project. And so we did a little call in episode where I called in and walked him through how I created a collection bucket in Notion and how I use it when I'm reading for curating, clipping things, saving on the go ideas. It collects everything. That's why I call it a collection bucket. I will link to a loom walkthrough of my collection bucket in the show notes and again keep an eye out on Cal's platform Deep questions, maybe even the YouTube channel because I did do some screen sharing. He did a good job of kind of asking me where I wasn't clear follow up questions of exactly how something works or why I set it up a certain way. You can also check out the episode on FreeTime111 with Tiago Forte where we talk about building a second brain. And if you really want to dive deep in this, it's a method called the Zettelkasten method. Sometimes it's called a commonplace book or a slipbox. These have been around since the 1600s that we know of, maybe even earlier. There's a fantastic book called how to Take Smart Notes that set me completely off of my notion collection Bucket strategy. Now in that book they actually talk about having a physical collection bucket. Authors like Ryan Holiday and Liz Gilbert talk about keeping index cards in a shoebox when they're working on a next book or project. I like to have mine digital because I like it in the cloud. I like to access it from any device while I'm on the go and have it all there. And I also use the notion just like Evernote has a web clip feature. So if I'm reading an article in a browser window or even on my phone, I can easily send that article to get clipped into this one. Catch All Collection Bucket. So the reason this is strategy number one is that if you have a collection bucket and and you set a little goal for yourself to collect one or two snippets a day. Whether it's an idea, a quote, a highlight from your book, you're reading a personal anecdote or story, an idea that's original to you that you have while you're walking or showering, commuting, put it all in there. Because then when it comes time to sit down and create content, you have this whole wealth of idea ingredients to draw from.
The second strategy. And this might fall under number one. The collection bucket is specifically around personal anecdotes or stories. My favorite resource for this is a book called Storyworthy Hat Tip to Leanne Hughes, who I first heard the author on her podcast first time facilitator. The author's name is Matthew Dix and he says that our homework for life is every day to capture a story, a personal story, and specifically a moment of transformation. It doesn't always have to be for the better. It could be five seconds where we have an insight or an aha about ourselves, or a pang of regret or guilt or nostalgia or anything at all. Something that might seem ordinary in our day. But by reflecting every day in this homework for life, we think, what was a moment that really moved me? Or where I changed a little bit? Or where I had an aha moment? I don't always hit it every day, but I do try to capture a few seconds storyworthy snippets in my collection Bucket, but that are specifically personal insights or anecdotes at least a couple times a week. I also refer to this as capturing truth while it's fresh and or share when it's solved. So in the past I've done an episode called when the Financial Tides Recede. That's the truth while it's fresh because I was in the midst of investing a lot of money in building out this brand new free time book and brand and so my truth while it's fresh is me right in the moment of that feeling. When the financial tides recede, how do I think about it? How do I stay calm? How do I surrender to what's going on? How do I not rush to fill the gaps by doing a lot of activity just out of a sense of scarcity? So that's a good example of truth while it's fresh. Or, and, and, or it could be either way, share when it's solved. So I don't know. I'm never going to solve the issue of financial tides surging and receding because that's the way of life, that's the flow. Sometimes it's going to be really robust. Other times we're in a recession or a pandemic and things recede. But sharing something, when you have solved it or you've found a partial solution or a strategy, a way of coping with something, just something that you've made it through to some kind of other side and you can look back and share some strategies. I mean, today to go meta again, I was feeling just on the other side of being sick, uninspired. What am I going to talk about today? Okay, well, how do I generate ideas? So I went and looked what questions were coming up most frequently in the free time toolkit. And we'll get to that in the Next item number three of always be listening. That's what gave me the idea. And so now here this episode is partly me sharing how I solved my own feeling of being a little bit uninspired or unsure of what to create. And by the way, sometimes this question of idea generation, it gets a little harder the longer a project has been going. Because, for example, brainstorming the first 10 solo episodes of the Free Time podcast in a way were much, much easier than trying to brainstorm. Now, as we're approaching 200, it's kind of there's a sense of oh shoot, well, I've already said the really big stuff. Now what? Or I already wrote the entire book and there's over 150 podcast episodes. Now what am I going to talk about? And so it's also trying to find angles or ways to keep it fresh. And the personal stories I do think help a lot and also diving into specific aspects of maybe bigger or broader topics that have already been covered.
Number three, Always Be Listening. This was a chapter of Free Time, the book I I have what I call Always be Listening ABL forms throughout my business. Anything that you do when you interact with the website or communicate usually has some kind of listening question. So for example, to access the FreeTime toolkit, yes, you put your name and your email, but you also say if I, Jenny, could wave a magic wand and help you fix one thing in your business, what would it be? Or if you download the Author toolkit that's@itsfreetime.com authors there's a similar question. What's your biggest question when it comes to the book writing or publishing process, you can always be listening in so many ways. I even have listener submission forms and I have if you want to submit a question via voice memo@itsfreetime.com ask there are all these ways I outline more of them in the book where I have little listening moments throughout ways that you can interact with my platforms. What that enables me to do is always have a steady stream of what's on your mind. How can I be most helpful? Another way that you can draw inspiration and ideas is what are your friends or your community members asking you most frequently? So what are the FAQs? And I even find that yes, I do a lot of listening from the broader community. Maybe people reply to an email newsletter or submit something for the podcast or but actually a good source of ideas are introductions from mutual friends or people reaching out that I know loosely who say I'm just wondering about different book publishing options. What should I do and I usually recommend people could leave me a question in Voxer. I try to connect with them asynchronously, but as those start to pile up I think okay, maybe I need to just sit down and record an episode on this or create content around this that I can share more easily because I keep getting asked the same question.
The final strategy on this one. Number three for always be listening. You can also actively solicit submissions. There's nothing wrong with that. I've seen podcasters put out a two minute episode where they say it's time. Send me a question. I've heard podcasters say no one submitted questions last time. I really mean it. Let's try this again. You can send out to your email newsletter list. You can link to a survey, even just a three question survey and say what's on your mind? What's your biggest challenge at the moment? What would you love to see me talk more about? Or you can just have people hit reply and say, I would love to know. How can I be most helpful? So don't be afraid to also actively solicit submissions and say I'm generating my next batch of content. Fill in the blank newsletters, podcasts, articles and I want to hear from you what's on your mind.
We'll be right back just after this.
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Number four, something I call synthesis. Introducing a new concept by fusing ideas together or seeing what's missing out there. So I love to use metaphors. As you know, the power of a metaphor is being able to help people see something differently in almost like a mental shortcut. Saying this is like that. Even a recent episode I did on what's the low hanging watermelon in your business? We all know that corpse peak term, the low hanging fruit. Okay, but now I'm going to Put a twist on it. What's a low hanging watermelon? Something so big and juicy you're almost missing it because it's right in front of your face. And then I might borrow a metaphor from a friend, as I did in that episode, and say, but let's be sure that according to Mike Michalowicz's pumpkin plan, you're not watering a pumpkin that you shouldn't be. Like, he's all about removing small and medium sized pumpkins so you can grow only the big opportunities and focus on those and your very best clients. So that's just me having fun, trying to synthesize ideas, bring them together, take something from somewhere, mash it with something else, create my own little PB&J sandwich, Oreo cookie, whatever metaphor you want to use. Deli sandwich, Yummy soup. I often used to ask people, if you could be any kind of food, what would it be and why? And I always would say that I'm a chopped salad because I love to have a really robust salad. It's healthy with lots of little ingredients. So whenever you're in doubt, just think about what's a metaphor that relates to a problem or challenge or even a solution that I've recently figured out.
Number five, figure out how you are contrarian in some way to a trend or something in the news. So when everybody's talking about the great resignation, do you have some other angle on it or quiet quitting? Now, some people call this news jacking or trend jacking because, okay, there's something going viral like the royal family drama, okay, and then you come in with some angle or kind of contrarian perspective. I don't do this a lot. Sometimes I skip jumping on any kind of news trend because I find that it's not that evergreen or it's also noisier. There's so many people talking about quiet quitting or the great resignation that I don't really have anything original to add. But when I genuinely feel that I'm contrarian in some way, that I have a perspective that's different than what everyone else is saying or doing, such as running my business without social media even, that's much more common now than when I was first, first talking about it and my friend Alexander Franzen was talking about it even before that. That's an example where sometimes sharing a contrarian view that you have can give people their own permission of how they might want to do things differently. So I was kind of looking for ways that how am I an outlier? What am I doing or thinking that's different. And often the way that first shows up is kind of beating myself up. It's not like right away, oh, I think I'm somebody genius. Oh, I've really figured something out. Usually when I am contrarian in some way, it's. I'm thinking, what's wrong with me? Why can't I hack this? Why can't I handle this? Why am I so overwhelmed by all these inboxes? What does it mean? And then as I start to give myself permission to drop things altogether, that's when I might feel more comfortable sharing. Well, hey, I'm putting my foot down and saying, yes, you can run your business without being on social media. Sure, you're going to give up certain things and maybe you won't be everywhere on all platforms. Maybe people will miss you if they're searching for you there. But is that the end of the world? I'm not so sure.
Number six, this is kind of related. Figuring out a trope or a common quote and then do you agree or disagree? There's just so much out there. I mean, just to give you a few examples that made it into the Free Time book. There is Benjamin Franklin's line that time is money. Well, it became the flap copy to the book where I say, time is not money, time is life force. Time is far more precious than money. Now, it came to my attention later, just recently, that maybe Ben Franklin also was getting at life is precious and time is even more precious than money. Later in the letter that he was writing. I'm not sure. I have not been able to find it yet. If you know of a passage like this, please let me know. In any case, we've certainly made it a common trope or idea, at least in the US that time is money. And so what does it look like if we go around that time is way more important than money. What does that mean? What does that look like? Another example that I share in the book is the you are the average of the five people you surround yourself by. Okay, is that true? And in what ways might that be true? For example, if all you care about is success and money, then you better surround yourself by four of the even more successful people than you are, and hopefully they're way wealthier and certainly wouldn't want anyone bringing your averages down. But what if you surrounded yourself by five of the kindest people you know? What would that look like? Or you just made sure that of the five people you most frequently surround yourself by, that they have good energy, that they Energize you. You better when you stop interacting with them than when you started. And so just at least exploring these ideas, because sometimes I'll think about a common phrase or trope and it makes me feel bad. And then I go, why is this making me feel bad? And that might mean that I have something to say or something to offer or a way to look at this differently. One more example here that I share in the book. I open one of the chapters by saying that line, the way you do one thing is the way you do everything. I can't tell you how many times I've thought about that, where I'm sort of getting really sloppy in a yoga pose. Like my nemesis pose is Bird of Paradise. I hate it. Half the time I just don't even attempt it. And I go, oh, shoot, this must mean that I'm lazy and I give up on things too quickly and I don't push through my discomfort and I have all these stories about it. And when I was writing Free Time, I thought to myself, how can this be true that the way we do one thing is the way we do everything? Isn't it more true that the way we do things that we love, that we enjoy, is so much more flowing and fun than the way we do things that we really hate to do? So I don't know. You know, sometimes I can make the case for both. That's why throughout the book pivot, I have all these pivot paradoxes. Like when the grass really is greener. You know, there are certain times that we have to acknowledge. We don't want to fall into a trap thinking the grass is always greener somewhere else. How do we find our joy now? How do we be present now? On the other hand, when it comes to career, sometimes the grass really is greener in another context. When you're meant to work for yourself, but you're currently working within a large organization, there are examples and counterpoints for some of these really common phrases. So at the very least, we could say for this one, number six, you could find a trope or common quote, agree or disagree, or at least identify a paradox within your field, within your expertise areas. What is a paradox? Where do you have to hold two truths at the same time?
Number seven, you could generate some content or ideas around trend forecasting and what I've learned about forecasting trends. And when I've asked people, how, what does it mean to be a futurist? They often say that it's already present in our reality. It's not some super far away thing, but maybe most people aren't seeing it or noticing yet. So you're hearing all the buzz and everyone's Talking about these ChatGPT tools and AI and what does it mean? What's it going to look like? I mean, I happen to think that half the LinkedIn posts within five years, if not much, much sooner, are going to be generated by various ChatGPT tools because it seems like it's quite aligned with generating, like business or career, I don't know, social posts in some weird way. But you could just ask what's here now that you're noticing first? Or what are you extra sensitive to? I'll link to some Pivot episodes with Professor Tom Guariello, who was talking about this, the publisher at Idea Press, Rohit Vargava, on identifying megatrends. And I also did an episode on lessons we can learn from Seinfeld and even Larry David of just how cranky they are because they notice. And then they name these little things, like there's a Larry David curb your enthusiasm skit on being a bad middle when you're seated at the middle of the table. And what happens to the whole group dinner dynamic when there's a bad middle versus a skilled middle facilitator. And that just cracked me up. So they have to have the sensitivity and or the crankiness to notice a common annoyance or thorn in your side and then they name it. That's what I find so brilliant.
The last one, number eight. When you really feel stuck, it is helpful to get quiet. Maybe you have a meditation practice, maybe not. But just getting quiet, taking five minutes, closing your eyes, maybe listening to some good music and seeing yourself instead as a channel. What wants to come through me? What can come through only me? How can I serve as a messenger? Another way that I think about and tap into a bigger collective consciousness is what is the love letter that I can write to my audience or my ideal customer? So instead of trying to create helpful content, what's the love letter? What's the thing that if I were writing to someone or sitting across from a dear friend in a coffee shop, I would just want to say to them to create some ease or joy or save them time. You know, these are the things I care about. Unburdening people, creating more freedom, just releasing what's weighing people down. That's kind of my vibe. You might have a different one, but a way that you love to serve. So when all else fails, surrender. I learned so much of this from Tosha Silver and her book outrageous openness that really stopped trying to push the river as the Zen saying goes. The pushing the content river and asking what wants to come through me? How can I serve as a messenger in this moment? What do I need to hear? What do I wish that I could read or listen to that doesn't exist right now? That would be so soothing or reassuring or inspiring or motivating. What do I need to hear and how can I be a messenger for others who might need to hear that exact same thing? I hope you found these helpful as always. I would love to hear from you. What are one of your go to idea generating strategies? Especially when you feel stuck or blah or meh. You know, we all know what it's like when you're on fire and your ideas are coming left and right. What do you do when you're stuck or you hit a dip or you've been generating content for so long that you feel like you've run out. Leave me a voice memo@itsfreetime.com Ask and we can do a follow up episode with your ideas. Thank you so much for being here and listening everybody. Have a beautiful rest of your day.
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