I always enjoy getting to speak to groups of people trying to untangle money, work, values, and how to be ok and have enough – according to you – in this environment and world.

Plus a really good group will get me preaching on my soapbox – and that’s how we got this video.

This lively recording is from a workshop I did in May 2026 for my podcast co-host Pippi Kessler’s Next Step Circle workshop, a monthly community for people working through a career change. 

Pippi asked me to prepare a lesson, and there were incredible questions from the group, which means this 27-minute video lecture covers:

• How to loosen some of the hard feelings many of us have about money
• How to make more money [when you dislike money] 
• how to save money when it flies out of your account
• Ways to think about balancing paid work and less-paid soul work
• Money envy, scarcity, and our relationship to struggling
• Why wanting to have enough is ok
• A reframe to think about retirement
• Ways to give your money jobs and why that’s a hack to meeting your goals
• Deciding between higher paid freelancing and having a salary dayjob

The transcript is below – and, if you want to join Pippi’s group [which was fullllll of delightful people I would 100% want to go through a life change with], the details are here, or join here!

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VIDEO TRANSCRIPT: How do I make more money and have enough, Next Step Circle May 2026 lesson selections.

[00:00:00] how do you make more money when you don’t like making money?

What do I say to people? The first thing most of us don’t do things that we don’t like and don’t wanna do. So if you’re like, “You know what? Part of me wants to make money, and part of me thinks that everyone who makes money is an evil rat bastard,” there’s always gonna be some struggle in there.

And I think just acknowledging that and saying that is helpful, because it can help us with some of the self-judgment that comes in. I work with a lot of activists, movement people, queer folks, people who work cooperatives, democratic workplaces. just the best art weirdos.

I come out of activist and queer organizing cultures and communities, and there’s a lot of really well-earned distaste and distrust about certain things that money represents, and how it’s used inequitably and [00:01:00] unfairly, and all the things that we know. And when it comes time for us to be like I think I need some more money,” if what we carry with us is the belief that there’s no way to make money ethically or, anyone who makes money is a rat bastard, it’s going to be harder than it might otherwise.

I’m not saying you have to, shift your mindset to worship money. But what I am saying is if, is that it’s hard to do things that we judge, and it’s hard to do things that we are suspicious of, for good reason, right? And I spend a lot of time with people investigating what’s underneath some of these questions and investigating this in terms of thinking about do I want my best friend or my partner or my nibling to be resourced to have something they want to be able to do, pay to go to school?

take care of their, health and wellness in the ways that they see most fit. fill [00:02:00] in the blank, right? Often the answer becomes like yeah, of course I want my best friend or my partner or my nibling to have these things.” And so then we have to start getting into this nice murky gray area where money could actually help us do some good stuff, which is different than saying, “This is a wonderful system of capitalism.”

No, you do not have to say that. But it’s also true that money helps us resource getting things done, It can allow us to do things for ourselves, for others. So when we’re asking ourselves, “I think I need to make more money,” one little piece that’s really helpful, we don’t have to, but one piece that’s helpful is to be like what if money isn’t the worst possible part of this?

What if money is the tool and the resource that’s gonna facilitate this thing I’m trying to do,” right? We start to loosen some of the hard, well-earned hard feelings that a lot of us can have about money. [00:03:00] So that’s one piece. When I wanna make more money, it’s a lot harder if you’re like, “But I hate money,”

And then when people say, “I wanna make more money I’m getting okay with it. I’m working on it,” the next thing I start to ask them is how much more money do you wanna make?” It’s really different to say, “I wanna make more money” versus, “I want to have $1,000 more a month.”

It’s really different. One is tactical and one is more like squishy and aspirational. It’s okay to be squishy and aspirational, but It’s harder to figure out the steps towards a squishy and aspirational thing. So if you’re thinking to yourself, “I wanna make more money,” I would deeply encourage you to put a number in your mind, even if that number is like a best guesstimate or y- you just pick from your gut because our brains are these beautiful narrative machines, and when we give the narrative more detail, [00:04:00] we can start to make plans around it.

Number three, I wanna make more money, I would say specifically for what?” Like how specific can you get? And I wanna name,It can be really challenging to do this kind of, specific imagination work when we have experienced marginalization or living with limited resources.

And I still am gonna invite us to attempt to do some of it as specific as we can. For what specifically do you want money? Seriously, y’all, I coach people on money every week. This is something that we spend a lot of time with and need to slow down with. So I encourage you to, be slow and kind and gentle with yourself when you’re trying to get these specifics.

Because we’re really doing is we’re saying, “What needs have I not yet met? What dreams do I want to be able to make real? What is actually important to [00:05:00] me that maybe feels out of reach right now?” That’s the question we’re asking when we’re saying, “To what ends?” or, “Why do I want to make more money?”

And I’ll just give a couple examples, so I’m not being theoretical. But that could be getting pregnant having a commitment ceremony with a partner going to get more education buying a home, right? It could be some of these, bigger, chunkier life goals. But it could also be I wanna get acupuncture every month, or I wanna send my spouse to get a massage ’cause

She needs more massages, it could be I wanna be able to go to the local collectively owned queer feminist bookstore and buy two books every time I go, right? I wanna be able to support my friend’s business and buy from them. On and on.

These are just a couple examples, … Hopefully you can imagine that the list for you is gonna be specific and custom to you, and your family and your [00:06:00] communities and what’s important to you and what you need. But how do I make more money? we start to think about what do I wanna make more money for?

And then the last little practical, tactical piece is on what timeline? There are some things that we want more money for that are just “When I get there, I’m there.” There are some things that are really time-bound. I wanna start a program that starts in October, and I need two grand to put down my deposit,

That’s,That’s the whole story right there. How much- For what? On what timeline? Because it is easier to say, “I need to figure out getting two grand by October ’cause I wanna start this program,” as opposed to, “I need more money.” Do y’all feel the difference?

Because our little tactical smart brains can start to work with, “I need two grand by October for this program.” We have the why, our motivation. We have the what, how much, and our [00:07:00] timeline. and we can start making action plans and trying things. I like to tell this story how in 20- oh, God, a while ago, I started, saving up for a motorcycle.

I really wanted a motorcycle. I didn’t have a timeline. I was just like, “When I get there, I’m there.” And I was living on, maybe 30 grand a year in Brooklyn, and it was tight. But I really wanted a motorcycle, and I was like h- I, first off, I could just deny that I want this and never figure it out,” but what changes if I challenge myself to say, “This is figureoutable.

I can meet this desire that I have”? And so I just did the old-fashioned 20 bucks a week in an envelope method. I knew I was gonna end up buying the freaking thing on Craigslist and eventually, it took three years, but when I got there, and then I took my little envelope of 20s and, met some random [00:08:00] and bought their Honda Rebel from them.

It was small enough to be achievable. I was motivated to keep making it happen, and that was a method that worked for me that felt like it could meet where I was with how I was making money at that time. If I’d wanted to do it faster, if I’d had a timeline, I wanna ride to Baltimore to see some friends, I might have taken a different approach,

How much money? For what specifically? On what timeline? These are our tools when we’re trying to figure out how to make more money. sometimes we’re making money towards goals that end: buy a motorcycle, right? Put a deposit for a program. Sometimes we’re trying to make more money because life is just more expensive than it was last year, and last year it was more expensive than it was the year for before, et cetera,

We’re trying to make more substantive, ongoing shifts in our overall earning. It’s still really useful to say, “What’s the difference of what I’m earning today versus what [00:09:00] I really think would be more supportive for me?” It’s still really useful to say for what. I wanna be able to spend 200 bucks a week on groceries instead of 125, Getting specific really helps us.

So what I’m saying about how do you make more money is that there’s certainly many different ways to figure it out. what I’m pulling in here is, first we have to not secretly not wanna make more money on some level.

Again, that just makes it harder. It’s still doable. People do it, but it is harder. And then when we figure out for what, our tactical, practical brains start to come in. I wanna give an example. I work with a lot of small business owners who are, one-on-one service providers therapists, acupuncturists coaches,

And hypothetical, this is no [00:10:00] one actual person, but this is, a common version of what I hear. It’s, “All right, I’m seeing “20 clients a week,” “and every client pays me $100, and so I’m able to make $2,000 a week.

And I have my business expenses, and I have to save for taxes, so I have maybe, I’m just making the math easy, “$1,000 a week to pay myself after all this other stuff is getting paid for, my studio rent, et cetera, et cetera.” And we kind of work together to figure that out, and then we can look at the numbers and say, “Okay, looks like you’re able to pay yourself about $4,000 a month, $1,000 a week.

What’s not getting covered in that $4,000 a month? where’s the gap?” They might say, really wanna save up to go traveling with my best friend.” We can start to get specific. When are you gonna travel? Where are you gonna go? Hypothetical person is like, “Yeah, I really wanna be able to go to,” Mexico City and [00:11:00] Oaxaca.

I wanna go for two weeks. I wanna be able to, stay places da. We can estimate that maybe they need to save $3,000 for this big, magical, special trip. Okay, great. When do you wanna go? In six months. Okay, great. I need $3,000 in six months for something that’s really meaningful to me, trip with my best friend.

So we’re gonna break it down and say, all right, looks like you need to make another $500 a month after taxes and expenses and then you’re gonna have that money saved. so then we get to get practical. Okay, how do you make another 500 bucks a month? Is it seeing five more clients? Might be one option, right?

Is it having a group project that you do, Is it, getting a job somewhere where you can get 500 bucks a month, There’s actually lots of different creative… Is it babysitting? Is it selling stuff on Facebook Marketplace? is it digging around in the savings bonds that you got [00:12:00] at your bat mitzvah?

There’s different ways we can start to figure out where that money might be when we start to break it down. And I think it is also useful to recall that, when you work for yourself, if you have a savings goal, you need to be able to, earn, more ’cause we’re gonna be paying taxes on things like that, of course.

We don’t wanna forget. But there’s something that’s also really gorgeous and life-affirming about saying, “There’s a thing. I really wanna be able to do it. I can figure out how to get there.” And what I love in particular with people who are trying to set up a time-bound savings goal is to say, what if you just made some tweaks to how you’re earning and what you’re doing so that extra 500 bucks a month is ongoing?

And so first you’ve got this goal about saving for this trip with your best friend, but afterwards, what might it look like if that 500 bucks a month went into something else that you need or want, Saving for an emergency fund, getting your car’s brakes fixed, [00:13:00] adopting a dog with your partner, fill in the blank, y’all. The thing about life is that there’s endless things we could resource. There’s not endless resources to resource them with, of course, so we’re always getting to be in a place of discernment and and prioritization, right? What’s most important right now? What’s possible right now?

I also wanna talk about giving away and sharing money, which I think is, a very important values-based approach to resources.

And it’s beautiful, and I love it, and I’m not about to sit here and be like, “Don’t do it.” You should totally fucking do it. If giving money and sharing resources is part of your value system, do that, Live into your values in that way. and I just wanna say, if you’re a person who cares about that, when you have a little more money, you can do even more of it,

Money isn’t actually a toxic thing. It could let you do more of something that’s already important to you. I always wanna [00:14:00] shout out the, very beautiful working class, interdependence value of, sharing what we have even when, the pot feels limited.

I feel like I get a lot of this question, which is, “Who am I if I have enough money?” I know who I am if I’m struggling. I know who I am if I’m commiserating. I know who I am if I’m, passing that 20, 30 bucks around, to, the GoFundMe.

Goddess bless that 20, 30 bucks we all keep moving around for real. but am I different if I’m not struggling with this piece? The answer, of course, is only if you wanna be different, we can change regardless of how much money we have or don’t have, right? But sometimes there’s, this inherent assumption that having different resources over the course of our life changes who we [00:15:00] are.

Moving out of a place of scarcity totally is scary. it’s the difference between an identity shift and a relationship with our identity We don’t have to change when we have more money, but we feel like we might be somebody else. My relationship with my identity. That’s real.

Something else people find really useful I know I’ve found this really helpful, is that money from different sources has different jobs. So maybe my money from my day job is saving for travel and going into my retirement and paying for my other treats or whatnot,

And then that’s my regular recurring, I know what this money is money. And then money that kind of comes in erratically, I do some consulting, I sell something on Facebook Marketplace, I do a random art show, then maybe that goes to a different goal, right? Something that’s more long-term or special.

It can be nice to be like, ooh, the, I got all the money for my motorcycle project from doing [00:16:00] theater. This rules. Like we’re allowed to have positive feelings about the energy of money And it can actually sometimes be really cool to create that positive story about where you got the money for something.

But you don’t have to have some gorgeous positive story to be allowed to save money and have money, right? Just to be clear. Sometimes we just have to work a job ’cause we need income to survive in America and healthcare, and that’s okay.

When we’re thinking about things like retirement money, which I know, retirement, LOL, America, the environment. I know. And I think of putting money to retirement.

My friend Gail has this amazing way of talking about it where she says, “You’re betting on the shadow future.” What does she mean by that? when I’m putting money into retirement, I don’t really want the capitalist system of AI overlords to continue to make money. I really… I don’t. and if that whole system crumbles and all of my stocks and money goes away, I’m actually happy because that [00:17:00] terrible system has fallen apart.

But if that system doesn’t crumble, I’m betting on the shadow future where these triflers still keep making money, and then in 30 years when I’m even somehow more gray, I have some money and I can spread it to, my friends and family and community, right? And so I’m betting on the shadow future.

I’m happy with either outcome. This is what I think about when it comes to, putting money towards retirement. So if I especially, when we’re younger in life, 20s, 30s, even 40s, retirement money has a long time to do its thing.

It’s really worthwhile to put even, a little bit of money towards it. And if you’re somebody who has a job that offers a match to your retirement,please contribute to meet the match because you’re doubling your money. It’s really hard to double your money. This lets you do it.

scarcity shows up in at least two ways, probably more. One [00:18:00] is real reality scarcity,

not having enough money to have the things you need, And, knowing what that looks like, feels like, embodying that. Scarcity can be this really real lived experience that we can be tactical and practical about,

And we can say to meet mybasic requirements,” hypothetical, “I need $5,000 a month to pay my mortgage, to get my kids in daycare, to pay for all the stuff. this is just what life costs right now. So if I have less than that, I’m operating in practical scarcity.”

And then we can make some plans around that, right? Create runway to go from one job to another to make sure that those practical needs are met. I think about that as a teeter-totter, When people want to transition from careers. Sometimes we have this short period where we’re, actually working a little bit too much because we’re trying to make the teeter-totter move.

I’m still bringing in the money from my old job. I’m trying to bring up the income from the other job. or I’m saving six months of my costs so that I can hit the ground running and start making money [00:19:00] with a new project or career while still not being in practical scarcity, not able to pay my mortgage.

And then there’s projected scarcity or the scarcity that we are trained to be afraid of in American society. whether that’s scarcity for ourselves or we look at other people or we read stories about people in scarcity and we’re like, “Oh, my God. I don’t want that.”

And I think those two kind of smash up against each other, right? If you’ve experienced scarcity or you’re looking at something practical like stopping bringing in your income, that is very real. You wanna be able to have a place to live, have food. Addressing that isn’t mindset.

It’s realistic and strategic. But then there’s also this totally, fear-mongering thing that happens that’s “In America, you don’t wanna be poor. Look what we do to our poor people,” and any of us who’ve ever been poor, it fucking sucks. And but that’s the fear factor piece.

So I think differentiating the two can be really helpful. Which scarcity am I like thinking about right now? Is it [00:20:00] actually me being wise and discerning and making sure that I’m not going to enter into a scarce environment? Or is it me listening to these stories about how if I don’t have a corporate job, everything’s gonna fall apart?

‘Cause there’s tons of self-employed people across the US, right? In creative and non-creative fields.

If any of us are people who figured out how to have some reliable, decent chunk of time in our lives where we can do a thing that we love, that’s the life hack unlocked, right?

‘ how do I actually save money?

the second I get it, I just spend it. there’s two things. Number one, many of us have a, habitual relationship to where our money is. What do I mean by that? If my money’s in Venmo, I’m treating it a certain kind of way. If my money’s in my checking account, I’m treating it a certain kind of way.

Oh, look, how much money’s in my checking account? Great, I have money I’ll spend it. So sometimes we have to get ahead of ourselves and our habits and our norms, [00:21:00] and put the money somewhere else that we have a habitual not spending relationship to. my paycheck hits or my client pays me, and I move a certain amount of money to savings.

Out of sight, out of mind. I’m not like, “Oh, yay, I have this,” right? I put it somewhere else where my relationship to it is different. I think that’s when we do have a little extra income, that’s the hack, right? How do I save money? I just put it where I cannot be tempted to get myself a little treat. right?

Or to, realize I’ve had enough little treats for the month based on what I’m trying to do with my money. the asterisk here is that sometimes if we’re operating in a kind of, income gap, like we don’t have enough income to cover our basic needs, then we’re gonna find ourselves transferring money back out of those savings with frequency, right?

and if that’s what’s happening, then that’s probably an indicator that there’s not quite enough income to cover basics, right? [00:22:00] Double asterisk if what you’re doing is transferring money out because you’re doing late night Instagram purchasing. That might be another flag. but then we can get ahead of ourselves as well, right?

Like, where am I spending money? What time? At one point I noticed, I was like, man, when I’m tired, like after 11:00 PM, if I’m just boop beep beeping on my phone, I need to just not let myself buy things because I will just… some other critter takes over my brain and I’m like, “It’s okay to buy random things on Instagram.”

what happened here? This is not who I am, right? So sometimes we have to understand ourselves and our habits so we can get around, what we’re doing.

You can afford anything, but you can’t afford everything, right? one rainbow highlighter is never gonna be the thing that breaks the bank, right? One gold glitter liquid eyeliner is never gonna be the thing.

it’s the amalgamation of the habits around them, right? So I’ll, I’m a big fan of,I never shame myself or anyone else for any, specific thing. The question is [00:23:00] always, do my habits reflect the outcomes I’m trying to get? That’s it. And sometimes when we get joy from spending money, it can be helpful to give ourselves, a little special, no guilt spending account.

separate checking account or a separate, Venmo or something, Just, some other place where the money is. Or sometimes dedicate one credit card to it if you are, good with your credit cards and pay them off, and won’t forget about it, And you can set yourself a number.

I have 150 bucks a month to spend on- Whatever, whatever that number is for you. it can help you scratch the itch. ooh, screenshot buying. We’ve got some hacks in the chat. Yeah, when I open my phone and there’s like a checkout screen on it, and I’m like, “Thank God I didn’t do that.

How many press-on nails does one femme need?” I ask myself. the funny thing with money is that there’s no absolutes, right? I can’t say to any of you, everyone needs $300 in [00:24:00] fun money a month, ’cause everybody’s income is so different. Everyone’s needs are so different,

our access needs, our wellness needs, it’s all different for all of us. but what we’re always looking at is, the proportion of what’s happening.

Okay, I wanna answer this question that Pippi called out. Does it make sense to do higher paying contract work that is not benefit earning or get a 9:00 to 5:00 that gives me health insurance with less opportunity to grow income?

My hot take is, a 9:00 to 5:00 that you can slightly underwork is the absolute life hack. because research shows that most of us peter out our, high level executive work after about, depending on who you are, four to six hours a day, right?

There’s just only so much, high level brain work that you can do. so when we’re doing a day job, we’re often doing, five to six hours of work, and then there’s, the wraparound work. I gotta check my Slack, I gotta check my email, I gotta walk here, I gotta [00:25:00] get to that meeting, et cetera, et cetera.

versus consulting, we really do need to be productive for the hours that we’re billing. And so I like to think of a consulting full day as, five, maybe six hours. and so not only do I need to be able to bill my full day rate in five, six hours, but I need to be able to add somewhere between, 30, 40, maybe 50% to add on healthcare, retirement, insurance, things that the job would pay for me that, consulting needs to pay for me otherwise, right?

This isn’t to say that consulting doesn’t work. There’s absolutely, consulting gigs that I’ve certainly had, where if I’m able to make a rate that is, 150 to 300 for consulting, I’m actually am able to, meet the rate that I would be getting if working at a day job,

But the rate we need for consulting is often a lot higher than you think because you’re not doing eight hours in a day. and I need to fill in my [00:26:00] healthcare, and I need to fill in my retirement, and my PTO, and my extra taxes,and, right?

So if I was working for somebody else expecting to make 50 bucks an hour, I would want to be consulting at 100. And no office coffee machine. I have to buy my own freaking Keurig. for some of us, this is great. I’ve embraced the opportunity to buy my own Keurig. I’m kind of like that.

but it’s also very legitimate to say, “Oh, wow, great way to think about it.” at the end of the day, what if I had my office job and then I was able to have an extra hour or two of brain space for my creative thing every day, And so again, this is gonna be about your priorities.

Are you excited about entrepreneurship? Some of us think it’s pretty fun and cool, And enjoy that. In that case, figuring out the path towards that higher earning contract work might be the way for you, right? And there’s no shade on that. If you enjoy it, it’s a really fun life. [00:27:00] If you don’t enjoy it, it’s not as fun.