11: How to Optimize for Revenue and Joy
8 Dec 2025 · 25 min
Jenny Blake on balancing income and fulfillment for entrepreneurs. Build steady recurring revenue like monthly retainers to fund bigger bets. Design a daily happiness formula with meditation and delayed email, then tie your numeric goals to concrete purpose and lifestyle.
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Hi, I'm Jenny Blake, your host of the Pivot Podcast and author of the book Turn what's Working for you into what's Next, which comes out with Portfolio Penguin in September of 2016.
In this podcast I talk with peak performers to reverse engineer their most successful career. Pivots interview experts on what it takes to be agile in a rapidly evolving economy and open the kimono on what happens behind the scenes of my book and business. You can learn to capitalize on risk, fear and uncertainty as the doorways of opportunity. My promise is that you will leave every episode with practical tips, tools and tactics. For show notes from this episode, visit JennyBlake Me podcast.
If change is the only constant, then let's get better at it. Here we go.
I want to talk about something that comes up very frequently with my coaching clients and other entrepreneurs, and that's how to optimize for revenue and joy at the same time. If joy is not your thing, you can replace that with any value that's important to you and that can sometimes seem to be in conflict or even in an inverse relationship to to revenue. If you've ever heard the phrase from the movie Office Space Case of the Mondays, then you'll know the feeling. When you're doing work that no longer energizes you, and yet you think that maybe you have to keep doing things that way in order to earn money. Today's podcast will be mostly for entrepreneurs and solopreneurs, or really anyone with a side hustle that you're trying to monetize at any level. It doesn't have to be your full time job, it could just be a temporary project where you're hoping to earn a little cash. And I will say this is relevant to people who work for someone else as well. I don't mean to exclude you in that population. You just have to be a little more creative about how you frame some of these conversations with your manager. When I was thinking about this equation and let me just say, everything I'm going to share today has come from my own strength struggles with this question and I was thinking about, you know, so often I think people assume that there is an inverse relationship, that if we think of revenue and joy on a seesaw, when revenue goes up, the joy goes down. You got to work really hard and do all the right things in order to earn a living. But similarly, if you just optimize for joy or passion or purpose or art or creativity, that we assume revenue goes down. And that's the starving artist mode. I would say most people today, so many of us are working on entrepreneurial ventures of some kind at some level. It does not matter again if it's your full time thing, but we all want to optimize for both of these things. I don't think anyone aspires to be the starving artist, nor is that a sustainable way to live or a sustainable way to serve. You know, if you really want to make a big impact on the world, first you've got to take care of yourself. And that's the difference between what I call selfish with a little S and a big S. Selfish with a little S is important. You've got to think about yourself. You've got to think about optimizing for revenue so that you can build a sustainable business that allows you to not only get your basic needs met, but ideally an overabundance so that you have more to give more time, energy and money to spend and create the lifestyle that you really want so that ultimately you can be the best possible family member, partner, friend, community member, and serving the world at large. So I think it's really important to get this figured out.
I will say that I have the blessing and the curse where if I'm not deriving joy, if I'm not enjoying something I'm doing or it does not feel lined up with my purpose, which is to be as helpful as possible to as many people as possible. I really resisted. I almost can't do the work. And the reason I say that's a curse, it feels like a whiny thing to say, a first world problem. Oh, wan. I don't like this. I can't do it. But I really ran up against this very strongly when I was at Google. My job was perfect on paper, it really was. I was doing coaching and career development and managing authors at Google. But the daily nuts and bolts, the daily tasks that I was doing, I would say about 20% felt like they truly fell in my zone of genius. Working with others, speaking, presenting, teaching, building things, and the rest felt more.
It just wasn't as aligned. I was good at it, but let's say not great, not totally lit up. And ultimately that's what led to my decision to leave. And then once I built my own business, it's been four years now. There have been periods where I couldn't stay what I was doing. I remember I was gonna relaunch my build you'd business course and I had launched the first one very successfully. It was great. People made tons of progress. I use these tools often with my coaching clients, but I could not bring myself to look at the to do list. I just dreaded everything on it. When it came to relaunching and marketing it again. Ultimately, I used that resistance as a sign that I was not going to relaunch it at all. And I had done quite a bit of prep work, but I hit so such a wall that it let me know at that point it's not just a matter of laziness. It truly was not the right next move for me. And that sparked really a year, if not two years of not launching anything until I recently just relaunched or not relaunched, launched my momentum program. So the reason I say that that's a blessing is that you will know the feeling when you're doing something based on shoulds, based on only optimizing for revenue or money, it's not really sustainable. There will be a part of you that kicks in that says, I just don't know how much longer I can do this. And of course, we all have to be willing to buckle down and get shit done when finances are tight. At that point, when you need to pay the rent, of course we're all going to do what it takes. But let's say once that level is taken care of, I think it's so critical to at least ask the question, how can I optimize for revenue and joy again? Replace that with whatever value is most important to you. At the same time, if we don't ask the question, we are just going to assume that it's not possible and build these subpar businesses and side projects. When I think about the seesaw that I want to create and that I actually operate based on, instead of having revenue and joy in opposition to each other, I put them on one side of the seesaw together and and shoulds on the other side. I notice that as the shoulds go up, my revenue and joy goes down. And that doesn't work for me. And the more that I try and do what I should do or how, quote everyone else is doing things online, I get hives. You know, I can't do that and I notice. And when I can feel when my revenue enjoy goes down and my shoulds and my resistance go up, I know that something is off. So what I'm going to share now is actual tactical tips for how to optimize for revenue and how to optimize for joy. And I want you to be the one to hold the question and the possibility that both are possible at the same time. If you ask how can I optimize for both at once, you will come up with more creative solutions. And for me this is not a one and done scenario either. I have to stop midway through projects and ask how am I doing? I will often get to a fork in the road where the path that I had originally set out starts to feel bogged down, weighed down by sheds and I have to stop and regroup. And that even happened with momentum. I had built enough of the idea and then I got really blocked around what platform to use and whether I should use wishlist member plugin or build some custom solution or ning or something else and ultimately I want something else altogether or. And the whole point was I really had to stop and sit with it and say what format is going to bring me the most enjoyment both to build, market and maintain. So that's actually three things. All right, so let's get into revenue. There are three things I want to talk about here. Steady cash flow, making bigger bets, and then direct versus indirect revenue.
First, one of the biggest lessons that I learned that smacked me upside the head that almost led to me folding my business was the importance of creating steady cash flow. And this may sound obvious to all of you listening, but unfortunately it was not that obvious to me and it wasn't in the books that I was reading and it wasn't even in my conversations with other coaches. One on one. Coaching had been my biggest source of income. It has been really sometimes with speaking, but speaking goes up and down. And what happened was when I first started running my own business, I was bringing on clients in a project based capacity. So for one or three months at a time. And many would extend beyond the three months, but many didn't. Many felt like, okay, great, I should be done by now, right? And what happened was I was billing at so many oddball times of the year, I never really knew when income was going to come in. Some engagements got extended and stretched out and my income really wasn't predictable. Then at the end of 2013, I had been living in New York two years and it came to be that I had to move in order to stay. And so my rent doubled overnight, but my business income did not double with it. This was terrifying to me. I did not know how I was going to pay the rent and having project based billing did not make that any easier. And I was able to earn a lot for speaking gigs I was doing in the range of five to $10,000. That's fantastic when it's a big keynote. But I would get paid sometimes four months after the engagement just because of going through the rigmarole of the internal finance departments. So that was obviously not going to pay the rent either. And this time really forced me to think about how can I create steady recurring cash flow. I ended up switching all my coaching clients to a monthly retainer format where I would bill on the first of the month the same amount. Everyone had a recurring day and time, and I would do three sessions a month. This was hugely helpful because at least got everyone on the billing cycle of the first of every month. And that worked for them too. They could cancel at any time. Some would go three, some six. Some have been with me three years, three and six months to specify. So that was a huge step forward of creating cash flow. It took the pressure off of when I would get paid from some of these other more random gigs and even course and product launches. Another way of creating cash flow is a membership site. So actually, about a year and a half before I launched Momentum, I created something called Brilliance Barter, which I only piloted with former coaching clients. And that was really fun. It showed me that there is value to creating community. Some of the ideas I used in Brilliance Barter I have carried over to Momentum, some I haven't. But at the time that I had just moved, creating Brilliance Barter was really important. It was a way to create again recurring revenue and cash flow in smaller amounts than people who were wanting to hire me for one on one coaching directly. So that was an effort at scaling my time and my services, but in a way that still felt really enjoyable to me. And these are with some of my favorite people. You know, I love my coaching clients and we already had great rapport. So that was an example of taking people I had already worked with and creating something for them that both of us again can benefit from that ongoing predictability, structure, commitment and accountability.
Once you have. So I encourage you, if you're running your own business, if you don't already really sit with what will create steady recurring cash flow that is so critical. And it's really the bridge and the foundation that allows you to go for some of these bigger bets. So that's the second thing I want to talk about. Big bets. There is nothing wrong with them. I'd say if there's a lot of risk involved and it's very unlikely, that would be a Hail Mary for some of you. You're building a course or a product or something that it's a bigger bet, but it's not. It doesn't have quite the uncertainty of a Hail Mary. The best big bets are what Nassim Taleb, author of Antifragile, would call asymmetric. A lot of potential upside with limited potential downside. Someone asked me recently if I was nervous about pitching my second book to publishers, and to be honest, not really, because it was a really asymmetric opportunity. If I got a book deal, fantastic. It's huge. It's like an achievement of a lifetime. It's so exciting. It's an incredible honor. But if I didn't get the book deal, at least not then when I was pitching In October of 2014.
My business didn't lose anything. I wasn't going to be out on the streets or anything. There was no impact to my business other than opportunity cost of what would have been possible.
When you have steady cash flow, then you move to these bigger bets and they're great. I am all for big bets. I'm really all for building big, audacious things, taking risks, not just going with the steady, predictable, sometimes more routine or hopefully not boring, but more routine income, and really building things. This is where creativity comes into play. And anytime you're going to build something new, the sheer fact that it hasn't been done means that there really isn't a roadmap. And what I find is there's also not always a roadmap for how I want to promote something. Launching things is not my, is not my favorite thing. It's just not. And I'm willing to do it. And when I'm really excited about a book or something like the Momentum community, of course I'm really excited to share it with everyone and I know that so many people can benefit and I'm overjoyed to bring people more into the fold of my work and how we can work together. But that said, I love building the product itself. I'm less inclined to, I don't know, jump out of bed to write sales page copy or newsletter launch automation sequences and all that rigorous. So for me, I'd say so critical that if I want to get something out the door at all and I really ran up against resistance, where at many points throughout building momentum, I would just think to myself, oh God, do I want to do this at all? You know, can I even. Do I? Why don't I just fold it right now? You know, because I would have such resistance. So at each of those marks, I had to ask myself, okay, how do I build this in a way that will optimize for revenue and joy, and how do I launch it in a way that will do that? So with your bigger bets, I encourage you to ask those questions and know that you will probably hit four or five forks in the road throughout the process where you need to revisit those questions. And not just for joy and enjoyment, but also for the revenue piece. Like, you've got to keep checking in. Do I. Is this going to produce something sustainable for me? Is the expected income going to be worth the effort and the time that I put into it?
That brings me to a third aspect of optimizing for revenue, which is direct versus indirect revenue generating activities. And this is something that comes up quite a bit with entrepreneurs and coaching clients I've worked with in the past who are launching new businesses. It's really easy to get confused between the two types of activities. And so I know a lot of entrepreneurs who, let's say when they're just starting out, will do indirect revenue generating activities. They'll spend a lot, a vast majority of their time focusing on writing newsletters, scheduling social media, writing blog posts, writing guest posts, creating free giveaways. Those are all great. They're going to build your list, they're going to build your community. They're fantastic. But they're indirect. They do not directly lead to a purchase. Whereas writing an email to your network saying, hey, I'm open for business, I'm taking on coaching clients, here's a special friend discount. I'm looking for five people. Here's who would be a great fit for me. Here's what services I provide, here's why I'm awesome. An email like that, which you can search for my network Madlib template or I'll link to it in the notes, that's a direct revenue generating activity because if somebody replies to that email, it's likely that they're interested in working with you. A direct revenue generating activity would be launching a course or product, not just a blog post leading to a newsletter leading to a course. And that's fine too. I'm all for having a strong funnel of how you engage with people once they come to your site. But when the question is how to pay the rent the next month. Go old school. I mean, we really forget for all the social media tips, tricks and tactics that are out there, you can pick up the phone and call people and often need to get on the phone to sell bigger clients. Whether it's for coaching or consulting or speaking. Those are things that will require a bit more work and a bit more personal touch. So consider in your own business and you can even observe over the course of a week, what are you doing that is directly leading to revenue and what are you doing that's indirect? And is that proportion of those two things and how you're spending your time appropriate? Don't let the indirect revenue generating activities consume everything such that you actually have no clue how you're going to earn a living. And then similarly, the direct revenue, direct revenue generating activities get creative again. You don't have to do what everyone else is doing, nor do you have to do it online. I really want to stress that because so many opportunities will come from network and I know the term networking is terrible for people, but just look back in your history, the jobs, clients and opportunities that you've received, I would imagine that so many came from someone you already knew in some way. Or in my case, I feel really lucky that because I've been blogging for a long time, people are sort of aware of what I'm doing. So they will come to me. People will often self support select. But I've been doing this online thing for 10 years now, so it's indirect. It's definitely indirect. It's not like in the first five years people were knocking down my door to come pay me money. I had to be really thoughtful about how I made it clear what my services were and who I was looking for. All right, so those are the three big things to think about for revenue, cash flow, bigger bets, and then direct versus indirect. Now I want to move on to joy. How do you optimize for joy or purpose or passion or whatever you want to put in that slot? There are two ways that I think about this. Joy on a daily basis and then project based purpose. Let's talk about daily. Daily to me is it's not just about what you're creating, but how it is so important to me that I work on projects where I'm going to actually enjoy the process of building it and launching it and maintaining it. And if that's not happening, something needs to change. So I think about my daily happiness formula. That's more broad. This is how I structure my time in general. So waking up in the morning, doing a 20 to 30 minute meditation, making coffee, reading a book for an hour or two, tackling my most important priorities, and then getting into coaching calls or email, but certainly not doing email first. I don't even check my email until about 11am Because I don't want it to consume my brain. That would be my happiness formula, let's say, for my morning routine. But think about in your work, what format, what time of day? How can you tackle these projects in a way that.
Nourishes you, that that motivates and energizes you? So how do you find that enjoyment? I'll give you another example with working on the Pivot book. It's so easy. And I'm sure you've heard authors either write or speak about, oh, writing a book, it's so hard. Or people will often say that to me, I can't even imagine that sounds so hard. And I'm really trying not to use that language because I don't want it to feel hard. I want to attach attack approach this project with a sense of fun and ease. And when it starts feeling hard, like trying to come up with a subtitle for example, I just return to that like it will come to me. I go back to my vision. What do I, what do I want to achieve? And then I just really ask myself, how can I work on this? How can I work on this next editing phase or whatever next phase I'm going into in a way that is brings a sense of fun and ease. And I chose those two words because I think we're all familiar with the grind, the hustle, the hard work. Those, at least for me, come more easily. So fun and ease are the ones I actually have to intentionally work in. I do feel that I have a strong purpose, but all it is when I really look into this in my meditation and I reflect, it's what I said earlier to be as helpful as possible to as many people as possible. That's never comes to me any clearer than that. When it becomes clearer is on a project based basis. So that's what I'm calling project based purpose, meaning my first website life after college. The mission statement was something like practical tips, tools and templates to help you focus on the big picture of your life, not just the details. And anybody who's reading Jenny Blake knows that that theme is consistent. On Jenny Blake, the subtitle or tagline was. Then I updated it to systems at the intersection of mind, body and business. When I'm working on the pivot book. The idea is to help someone leverage what's working to figure out what's next that's more specific. So each time I'm choosing what's the purpose of this project? Project, and I'm hooking onto that. And I have questioned.
I have questioned, should my life purpose statement be more specific? I don't think so. I really don't think it needs to be because. And by the way, if you want to borrow mine, how can I be most helpful to the most people? That can start very small. It can start with you and your loved ones, you and your community, you and your friends. It just does not have to be this enormous thing. And once you answer that question from a small group, you can expand it out into these concentric rings, larger and larger. And that way it takes the pressure off. And all you have to know is the answer to what's the purpose of this project that I'm building or this website or this course, or whatever it is, even this business, in this incarnation of it, what is the purpose? What do I want to achieve? What? What is my vision? What does smashing success look like a year from now? How do I want to feel both as I'm building it and a year from now? What are people saying when they come up to me and thank me for this thing that I've built? How am I impacting others lives?
Spending time with those vision questions can help you articulate the purpose. And if it doesn't come in a perfect pretty package right away, no problem. Just ask the question, how do I articulate this vision succinctly and powerfully? If you can ask the question and write it at the top of a piece of paper, the answer will come. I know that it will. Our brains are really good at that actually, that you, I call it like throw something in the chopper and your subconscious will go to work and it will come up later when your brain is usually in a relaxed state, like in the shower or walking or driving.
The other thing I want to say about this whole conversation is this concept I'm calling color by numbers. When you think about the vision, I hear a lot of people say goals that are actually more of a means than an end. So I'll hear them say something like, well, I want a thousand subscribers. Or I would want my website Traffic to be 10,000 visits a month, or even financial based. I want to earn $10,000 a month, but for what purpose? So if we look at the website traffic goals, add some color to those numbers. That's the Whole color my numbers concept. Is that why? What would having a thousand newsletter subscribers get you? Usually for entrepreneurs, it does eventually roll up to money. And I'm not saying that's why we're all in it. I'm just saying that yes, you want to build this thriving, awesome community of great people, but if you're in this at all to earn a living, then ultimately those numbers are leading to something. And even if you have a financial goal, okay, for what? What's important to you about that number that you chose? How does that affect your lifestyle? How would you feel? Do you need that exact number or can you do with less? Or do you actually need and truly in your heart of hearts want more? There's no right or wrong answer and there's no judgment. It's what lights you up. What is the number that gives you a feeling of excitement and resonance? Because if you can find that and you can articulate what is important to you about that in terms of your values and your vision, you're going to be so much more motivated to ride out the inevitable dips of any project or business. And I think that's really important when we talk about joy as well. Because of course every single second of every day is not going to be joyful. But if you're connected to that project based purpose, then we're all going to be more willing to do the tasks that we don't love as much because we know what it's in service of, we know why those smaller tasks are important and if we're really resisting or not skilled at them. You can always delegate or hire someone if that's an option for you, so you can get creative about how those things get done. But the point is that connecting to that vision and that project based practice purpose will help you ride out the phases of the work that you're not going to love as much. But the point is not, it's just stop what you're doing if the entire project is something that just doesn't get you going. Because ultimately I believe that it affects the end result of the project, of how you launch it, of how excited you are to talk about it. This is maybe more of my woo woo perspective, but I just don't even think it's a formula for success to do things you don't want to do. I think you'll be much more successful if you connect with what in your heart of hearts feels really thrilling and what feels like a challenging problem for you that you've been able to solve, that you can share with others. If you're getting annoyed by shoulds by how you should build something, it's very likely that other people are too. It's very likely that if you can solve that problem and do things differently, it will actually connect with people. And if it doesn't, fine. I always say decisions are data. If you do something that doesn't work but you loved doing it, at least you love doing it. Now you can tackle the piece about okay, well why didn't it work and what would I want to do differently?
That about wraps up our conversation on how to optimize for revenue and joy. I would love to hear from you in the comments on the blog at jennyblake me. Or you can send me a tweet @jennyblake. If you want to learn more about the book, that's@thepivotmethod.com and I would love to have you in the Momentum community. You can learn more and find out when doors open again@momentumcrew.com thank you so much for listening, everyone.
Thanks so much for listening to this episode of the Pivot Podcast. To learn more and get in touch, visit jennyblake Me, where I blog about systems at the intersection of mind, body and business. Or find me on Twitter Ennyblake. And remember, build first, then your courage will follow. Hasn't it always.
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