What if the problem isn’t your budget—but your income? When cutting expenses isn’t enough, it’s time to rethink how money actually works. This episode breaks down practical, realistic ways to earn more without burning out.

Episode Title

When Budgeting Isn’t Enough: How to Earn More Without Working Yourself to Death

Episode Summary

This episode wraps up a multi-part series on money by shifting the focus from cutting expenses to increasing income. After learning how to budget, categorize spending, and manage money responsibly, the conversation turns to a hard truth: sometimes the math simply doesn’t work without earning more. Drawing from personal experience and insights inspired by Tiffany Aliche and How to Get Good with Money, the episode explores why income is tied to value, replaceability, and visibility—not effort alone. It reframes earning more money as a strategic, skill-based process rather than a moral judgment or measure of self-worth.

Top Topics Covered

Why Working Harder Isn’t the Answer

The episode explains why long hours and exhaustion don’t automatically translate into higher pay. Income is connected to market value, how specialized a role is, and how easily someone can be replaced. Understanding this removes shame and helps people think more clearly about their options.

Asking for a Raise—With Evidence

Rather than emotional appeals, raises should be approached with data. A “brag folder” becomes a powerful tool for tracking accomplishments, customer impact, time saved, and problems solved. This evidence makes performance visible and reduces anxiety during reviews and salary conversations.

Becoming Harder to Replace

Learning one critical skill deeply can change an entire career trajectory. Specialization, not job titles or degrees, often creates leverage. The episode highlights how focusing on overlooked problems or difficult tasks can dramatically increase stability and income.

Recognizing Hidden Skills

Skills aren’t just technical. Teaching, organizing, calming upset people, troubleshooting, and managing projects all carry real value. Personal life experiences—like leading volunteers or handling conflict—count and can be translated into paid work.

Side Hustles That Don’t Drain Your Life

Side income doesn’t have to mean building an empire. The episode explores low-setup, low-stress options that align with existing strengths, from short-term projects to platform-based work that fits into real life.

Key Takeaways

Making more money isn’t mysterious—it’s strategic. Income grows when skills, needs, and visibility align. The most powerful step is taking responsibility for understanding personal value and learning how to place it wisely. Whether through negotiating pay, building expertise, changing roles, or adding a small side income, progress comes from intentional, realistic action. When expenses can’t shrink further, increasing income becomes the other half of the equation—and it’s one that can be approached one small step at a time.

What other ways can we solve our money problems? That’s what we’re going to talk about today.

Hi, this is Jill from the Northwoods, talking about life issues one small step at a time. Or maybe a life issue is not wearing lime green. I’m starting to think that’s true.

So we’ve been talking about this series on money—how to think about money differently, to budget money, and then going on to think about how we put money in different categories.

Wrapping up this series, that’s talking about Tiffany Elise’s book, *How to Get Good with Money*. She’s the Budgetnista. She is on YouTube, and she has a podcast, and she talks about how regular people can get good with money.

We’ve talked about how we can figure out how to budget money and how we can save money. But maybe the question is, how do we make more money? That’s another option for us.

And there are some very practical, grounded ways where we can sometimes just look to make more money when the math just doesn’t work otherwise. This topic, like I said, is tricky, especially when it comes to money. There’s a lot of emotions built up into this, and it can create comparisons with other people and frustration and resentment and shame.

I was on the shame boat. I was embarrassed that I was so poor and I couldn’t pay my bills and I couldn’t save money. And I started doing things about it one step at a time.

Now, I mentioned that part of it was me gaining control of my money and putting it in different categories and different accounts that I had. But one of it is that when I bought this house, I saved the money to put the down payment on, and I got some money from Grandma to put the money down for this house.

But then it quickly became clear to me I couldn’t afford this house, and I was going to probably lose it. Or the first time a roof went bad or the furnace went bad, I couldn’t afford to do this. I was living very close to the margin.

And so the one question I asked myself was, what can I do to earn more money? That was the only way out. I couldn’t cut my bills any more than I had already done.

And maybe you think to yourself, can I make more money? Can I ask for more money? Or can I work just as hard? You know, I was. I was working really hard. You know, at some point I had three jobs, and it wasn’t enough. It just still was not enough.

First of all, you as a person are not measured by how much money you make. But your paychecks are tied to a value in the marketplace for the kind of work you do. But not only that, how easily it would be to replace you, to be honest with you.

So if you are someone who is washing floors, easy to find someone who can also wash floors. If you are working in specialized software, you’re a little harder to replace.

And so you have to start really thinking strategically. What kind of value in the marketplace am I providing, and how easily replaced am I? They’re two very, very different things.

But the one thing that you can understand about all of this is that we’re, like I said, paid based on the value, how hard we are to replace, and how visible that value is.

I have been in situations before where my participation in the company was very valuable. And like I said, this is not arrogant. I just was the 36th employee of the company. I knew how everything worked. I’m not easily replaced because I knew everything. I knew everything because I was there at that company from the very beginning.

But, you know, the question is, how visible is that? How much do people know that?

So it’s not exactly effort, and it’s not how hard you work, and it’s not based on how good you are or how tired you are. A lot of people think that they should get paid a lot of money for doing jobs that are just not in those categories.

And once I accepted this and realized that I had to take personal responsibility for my own income, I started treating it a lot more strategically than I had.

And so this is where the part of the book gets really interesting. Trying to earn more money is not necessarily about working harder, working more hours, you know, losing your life so that you’re not around people anymore. But instead becoming more intentional about the money you’re earning and what you’re doing.

So some things that you can do are pretty obvious. You can go in and ask for a raise. And it’s uncomfortable. People hate doing it. I know I would hate doing it. I did it once in my life, and it turned out okay.

But it was kind of funny, because I said to my boss, I said, “I’m not making enough money, to be quite blunt with you. I have retirement problems. I’m trying to fix my retirement, and I’m not going to make it.”

And it’s because of the amount of money I’m making. It determines how much money I can put away for retirement and how much percentages of money that I can give to my retirement, to other things.

And the boss said something to the extent, “Well, you’ve gotten raises every year.”

And I said, “I know that, but we just had 6% inflation. And if you get a 3% raise, you’re 3% down. And that means that you will not probably see the money that you earned in realistic terms a year ago for at least another four more years.”

“And so I am not surviving on this. You know, I can survive. I can pay my bills. But I have to do more because I do eventually have to retire.”

And I did get a raise. It wasn’t emotional. It was evidential.

Like I said, I was a key person. I had been at the company for a really long time. I knew everything about this particular piece of software. I wasn’t begging. I was presenting the facts that I was able to do things that other people weren’t able to do in that company, just because I knew everything about the software.

And she came up with this idea about a brag book. And it’s hard for us to brag about ourselves. At least it’s hard for me.

And so what you do is you create a folder of your accomplishments. And I call this—actually, it was Em who called it this, but I now call it this—the BLT folder. I don’t know why it’s called that. I have no idea.

But anytime a customer complimented me, someone said something nice about me, a project completed successfully, I solved a big problem, I saved the company time or money, I did something—it goes into that folder.

And that folder essentially was used for two purposes. One, it was used for my annual review. So when it came time for my annual reviews, I had a lot of fodder about how I saved.

Because my job was to travel around the United States and help customers who were in particularly bad situations get out of it. You know, they’re stuck. They don’t know what to do. They lost money. They’re not using the software successfully. They’re trying to get some sort of a grant, and they’re not able to do that because they’re not using the software well.

And I was able to go into every hospital and help them out. I was sort of like the rescue person. And there were not many people in my company who, one, could do that. There were a few people who could do that, but I was the one who was willing to travel enough to go make that happen.

And we had one customer who hadn’t upgraded for 15 releases. And we were going to cut their contract off and say, “You can’t have the software anymore because you’re not upgrading the software.”

My job was, within a one-month period of time, to go live in this other state, help that customer. I trained every person. I trained the leadership on how to use the software. I showed them how to use the software to get this very important grant. I got them upgraded 15 different upgrades, trained them on the new version of it, and got them rolling in a month period of time.

There were not many people in that company who could do that. And that’s not boastful. That is just, like I said, a reality. And someone who was willing to live in another place for a month to make that happen.

So again, that was for me to be able to present that to the bosses. When it comes time for your reviews, then you’re not relying on memory. You’re showing evidence of your importance. And that right there will remove anxiety.

Because I forget myself. When I’m writing myself reviews for the annual performance reviews, I forget what things I did. You know, I had traveled so many places that having this BLT folder allowed me to just remember the good things I had been doing in that company.

And then the next step is to make yourself less replaceable. If raises aren’t possible, or maybe the raises aren’t enough, the next step is, how do I become harder to replace? What skills do I bring to this that other people can’t?

It’s not necessarily like degrees or anything like that. It’s about what crucial thing can I do for this company that nobody else can do.

You might be learning a new tool or a new technical skill. Or improve—like I said, I had a writing problem. I wasn’t a very good writer, so I took classes on becoming a better writer.

But what I did was I picked key operations within the software that people didn’t understand. They didn’t know how to implement. Customers got tripped up on them more than anything else. And I decided to become an expert on this problem.

And that is what allowed me then to travel all over the United States, helping people with this one particular issue. It was my learned skill, and it made me invaluable.

So I went from being someone who was in support to someone who knew something that nobody else knew in the depth that I knew it in. So that translates into better job stability, and then it also translates into better raises once you get into that position.

And I think a lot of people—and I thought this myself—they think, “Well, I don’t really have any skills.” And that is never true.

Skills aren’t just about job titles. They may include a lot of things like organizing, teaching, explaining, calming people down who are upset, good writing, troubleshooting, coordinating, project management.

There are some skills that are just invaluable that people can do that aren’t necessarily these very detailed technical types of skills.

And so you think about that when you’re kind of looking at it. You can also look at some of the things that you’ve done in your personal life too.

Have you ever managed a team of volunteers? Well, that’s leadership.

Have you ever handled really upset customers? Back in the day, I used to work for Microsoft, and I became a technical team lead, and I was also the only manager who worked on the graveyard shift. That meant every time someone was angry, that call came to me.

And so I learned how to become good at handling very angry people. I had people who were actually providing threats and being very upset, and being able to talk them down.

Maybe you’ve organized events. You were some kind of an artist, and so for your college you organized an art event or some charity event or a fun run or something like that.

Or maybe you’re very good at supporting other people and being a leader to those. All those types of skills count, and skills equal more money.

And when we look at these skills, you have to take a look at it, and now you can start being strategic about it. Which of these skills I have could bring in more money?

You know, can I ask for a different role? Can I apply for a different role internally? Maybe I switch companies. Maybe I do something on the side. I get a side hustle that I’m good at, that I like doing.

And not everyone needs to have a podcasting empire or something like that. But maybe something that could just bring in a little extra income. Maybe something that you can work for just a few hours. Maybe one skill that you’re uniquely good at.

That’s enough to just bring in a little bit of money.

And a lot of times people—I hate to say it like this because I don’t like getting new jobs. I’m very much a loyal person when it comes to whatever job I’m working on. But honestly, people have made the most money when they move to other companies.

And it’s unfortunate that we don’t value the employees we have. We force people into moving into different jobs. So, you know, kind of keep that in mind. But that is a possibility.

So when I realized I couldn’t afford this house, the company I worked for loved me. They were promoting me. They wanted me to be a contract manager. They were doing all sorts of things.

But the money was never going to be much bigger until I got into a much higher level, and that was going to take years.

And so I left. I left, and I worked for the hard company, which immediately gave me a huge raise. But it was very difficult. I didn’t have any free time, and I spent barely any time in this house, which is hilarious that I got the job to get the house.

But it then put me on a track that I was no longer on before. Now, instead of sort of being a managerial person, I was a system administrator. It was a higher-end job, and it had a lot of room for growth.

I could get certified, which I did, in Windows Server and a lot of different Citrix and a number of other things. And so it led my path to doing that.

I realized because I couldn’t afford this house, I had to get a new job, and I did.

So there are ways of going about it that you can do in order to make money.

This last one about side hustles is kind of interesting, because we are sort of living in this side hustle culture now. And they can be helpful. You know, it’s something that you could do. They shouldn’t make your life miserable.

But is there a skill that you already have that you could do to make an extra little money that requires very little setup and won’t drain your energy?

I have a friend of mine who’s a project manager, and she’s fantastic at it. And, you know, can she help with small projects here and there so that she’s not working another full-time job, but she’s able to organize something for someone, and they would pay her a little extra money to do it?

Or I had another friend who created a business on her own so that she could help people out in ways that she was particularly skilled at helping people out.

And it’s funny because it’s not something I ever thought about. You know, it’s almost like having another hand and another arm. And it’s amazing that my friend thought of this, and I’m so proud of her.

But, you know, that’s the idea. Is there something that you can do, some way that you can take a skill or talent you have?

You know, in some sense, I sort of look at this podcast like this. I’m not making money at it, and I’m not making money at it right now. But maybe someday I will, and it’ll be helpful to me when I get into that position.

But, you know, again, is there a way that you can take something that you’re already good at and make it kind of into a side job for yourself? Maybe it’s something that you would actually like doing more than your main job.

But that’s the idea.

So the part I want to leave you with is essentially that making money is not a mystery. It’s not something that other people have to learn how to do.

The idea is that making money is something straightforward enough. It’s uncomfortable at times, and it’s hard to get new jobs. And a lot of people, like me, never want to change jobs.

In the end, it’s really just knowing what you’re good at and understanding what other people need, and then just connecting those two together.

It reminds me of the ikigai thing, right? What do you love doing? What are you really good at? And what do other people pay you to do?

And when you can find that, that’s what makes you the most valuable of all, because you have unique skills and talents. You’re kind of a mixed bag of traits that not every person has.

And so how can you make that happen?

You know, for me, like I said, it was being an extrovert who liked to talk to people, who’s willing to travel and listen to people and their problems, and then help them solve those problems.

That was the skill set I brought to that job, and it made me popular.

Essentially, they started a whole consulting arm of the business because a couple customers said to leadership, “If we could just borrow Jill for a month, I know we could get this done.”

And so I was the very first consultant in the consulting arm of the company. And it made me more valuable.

So make a list. A really long list. Every skill, every ability, everything people ask you for help with. And then put a checkmark next to those things that could potentially earn you money.

It’s maybe no action yet, but it will give you that ability to look for jobs or look for side hustles that will make you more money, that will make you valuable, that will make your time valuable.

And your skills, they do matter.

It’s about finding out who you already are and then learning how you can place that wisely enough so that you can make money.

And again, small steps matter. Whether you’re changing to a different full-time job or you’re picking a side hustle, this is a way that you can take your value and make it into something more.

So that equals the other side of the budget. If you can’t fix the bills and you can’t fix the reliable bills and the unreliable bills, maybe you fix the income part of it too.

Keep that in mind, because there are two equations to that.

Keep in mind the other way too: if you’re making a good deal of money and you’re never quite getting ahead, you’re probably spending too much money. So there are two sides of this equation.

And one other point about making money on a side hustle is there are a lot of basically online experiences that people are looking for help with.

There’s TaskRabbit, and there are a couple others where you can rent yourself out. If you’re a good web designer, if you’re a good artist, if you have the ability to edit people’s podcasts for them—I always thought about that too. Like, I could go in and start editing other people’s podcasts.

You know, even if you want to just take care of people’s pets. I thought about doing this too because I love animals, but I can’t have many animals.

And so there’s a place called Rover. I’ve used this site. That’s who took care of my cats when I traveled in my previous job. There’s Wag.

And then you get to hang out with people’s pets, go for walks with them, play with the dogs and the cats, and enjoy it.

I had a great person who did this for me, and I tipped the heck out of her because she noticed one of the cats was not feeling well. She thought he seemed kind of down. So she went home, got a book, and she just spent a couple hours reading on my couch so the cat could cuddle with her.

And boy, you want to know that I tipped the heck out of her when I got home.

So there are things that you can do that even if you don’t want to start a company or have a podcast or do a side hustle, there are a lot of side hustle companies out there that will let you do the thing you’re great at for a little extra income.

So give that some thought too.