What People Dont Tell You About Making More Money

I used to think that making more money would solve all of my problems. I’d think, “If only I made more money, everything would be better!”

Prior to freelancing, I was a nonprofit die-hard — my highest salary being $38,000, six years ago. In the years since then, my income plummeted. I struggled to find work and my last nonprofit job left me with a $30,000 salary.

I had the crazy idea that I was worth way more than that and that working for myself would actually mean making more money. It didn’t happen right away, but nine months into my freelance adventure, I started seeing a shift. Now, over a year later I can say I’ve more than doubled my income.

It’s been great. But now that I make more money, I realize I have a whole new set of issues. I’ve been hesitant to write this post, as making more money is a GOOD PROBLEM and I realize that, but I want to write about it as the thoughts and feelings that have come along with it have been surprising.

1. I feel guilty for making more money

This may seem silly, but I actually feel some guilt for making more money. Even though I knew I deserved to make more money, I still feel guilty. I thought I was supposed to be the perpetual low-paid worker, the working-class warrior. Upon further reflection, I wonder if I feel guilty, because for so long I judged/was jealous of wealthier people. I thought they couldn’t understand what real struggles were like and how embarrassing it is to take on any gig you can get, even if it means walking an invisible dog or cleaning someone else’s underwear #truestory.

2. I feel like a total fraud sometimes

Last week I visited family in LA and it was awesome. I took advantage of having a flexible schedule and spent time with friends and family. While I was there, my mom remarked on how seemingly quick everything has happened for me. “Yeah, it has,” I muttered.

Because of this, sometimes I feel like a total and complete fraud. My blog is a public record and you can go back to the start of my blog and read my lamentations of making $1,300 per month and struggling to find work. You can read about side-hustle fails and the crazy things I’ve done for money.

I’m in a better place now and I can actually turn down work. I can be picky. And it feels freaking weird. I’m still the same person I was, just a little smarter and tad wiser. But sometimes I feel like a fraud. Somehow being low-income felt under the radar — not noticeable (a very interesting observation indeed). Being more “successful” feels a lot more vulnerable. I have further to fall.

3. I’m terrified of things going back to the way they were

I’ve realized that reality is ever-fluctuating. We are always changing, growing. Life is full of ebbs and flows, successes and failures. A few years ago, I would do anything it takes to get by. I went on food stamps even though I was so ashamed of it, I worked as a housecleaner, and took every gig I could find.

It was honest, decent work. But I never want to go back to that place. Ever. The shame, fear, and depression I felt were so consuming.

Every day I work so hard, because I know that a loss of a big client, or a bruise on my reputation could lead me closer back to that place. And I’m scared. I don’t want to ever go back there.

Then I feel guilty about that. What was so wrong with that work, that place? Who am I to judge? As I mentioned, there are a lot of complicated feelings around this money thing.

4. I feel like I always want to be more generous

When you’re the broke friend, and your friends know it, they’ll never expect you to pay for things or to go out of your way to spend money. Now that I know my financial situation is better than some of my friends (for the first time ever), I feel like I always want to be more generous and pick up their tab.

I want to do things I couldn’t do. I feel like I should pay because I make more. I love being generous, but obviously that can’t be a long-term, all-the-time strategy.

5. I have to work harder than ever before

Make no mistakes, making more money is hard work. I’ve had an insane learning curve the past year and had to make a lot of difficult decisions to get here. I’ve had to say goodbye to clients that are my friends, I’ve had to say no, when I felt like I should’ve said yes, and find the courage to speak up when I really wanted to hide.

Being your own boss and earning more is fantastic, but I’m a one-woman show. I’m customer service, client services, marketing, admin, and more all rolled into one.

I’ve learned that running your own business feels a lot like you’re an elementary school student in college and you’re studying your butt off to try and catch up.

Bottom Line

Don’t get me wrong, making more money is fantastic. There’s no way in hell I’d be able to put nearly $4,000 to debt last month without it. It’s helping me reach my dreams and goals at a pace I didn’t think possible.

I’m eternally grateful for this opportunity and realize the privilege of my current situation. Now that I’m at a different viewing point, I realize money can help solve a lot of problems, but not all of them.

Do any of these resonate with you?


Melanie is a freelance writer currently living in Portland, Oregon. She is passionate about education, financial literacy, and empowering people to take control of their finances. She writes about breaking up with debt, freelancing, and side hustle adventures at DearDebt.com.

Currently she puts more than 50% of her income towards debt, while living a frugal, fun life. In addition to her love of personal finance, art and music, she is also a karaoke master. Follow the adventure @DearDebtBlog.

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28 responses to “What People Don’t Tell You About Making More Money”

  1. Jim Wang says:

    FWIW, these are all normal feelings and it’s good that you recognize them for what they are. It’s easy to be consumed by them and to fall back to old ways. You worked hard for what you’ve achieved, don’t take that away from yourself.
    Jim Wang recently posted…How to Build an Opportunity FundMy Profile

  2. Tyler says:

    What a great post,

    I’ve been a semi regular reader for a while never a commenter but I just had to say how awesome this post it. My goal is to in the near future have a similar situation, I’m striving to do as much work as I can in order to work for myself in full knowledge of the amount of work involved in it. It’s interesting you talk about paying for others because I’m starting to be in that area now and have found myself paying for people who don’t even need me to just because I can and that is a dangerous place to be.

    Thanks for the article,

    • Melanie says:

      Hi Tyler! I’m so glad you decided to comment. And thanks for reading 🙂 I’m glad you are working your way up to more income. It is a dangerous place to always want to cover your friends. I totally believe in generosity, but in moderation. We still have to cover our financial bases and my retirement account is practically nonexistent.

  3. I can relate to all of these, but especially feeling like a fraud. The Mr. and I are always lamenting that we still feel like imposters, despite having been in our jobs for 13 years and 17 years respectively. I know, it’s crazy. Obviously we know what we’re doing, but we also think that virtually everyone feels like a fraud on some level. So I say — let’s all try to let that one go! We have enough to worry about without contending with impostor syndrome. 🙂
    Our Next Life recently posted…Why Married Early Retirees Should See Our Marriages As Our Most Important InvestmentsMy Profile

  4. Taylor says:

    Thank you for such an honest post! I actually feel quite similarly. For the past two years, I was broke. As a full-time college student with three part-time jobs, I still could barely make ends meet. (I was responsible for all of my expenses—tuition, rent, bills, everything.) There were so many nights I spent crying and unable to sleep because of stress. Fast forward to a few months after graduation, and I am now working a full-time office job with benefits. Although my salary isn’t huge, I’m making more than I ever dreamed possible in college. Although it’s awesome, I also feel guilty and scared that it won’t last. Thanks for sharing; it’s nice to know that someone else feels the same way.
    Taylor recently posted…High Maintenance on a Budget: How to Save $4,000 a Year on BeautyMy Profile

  5. I’m still at the point of thinking, “if I had more money, all my problems would be solved” so I can’t honestly say I’ve had any similar feelings.

    My income has increased over the years but I’m not sure I’ve ever felt guilty about it because I know it actually took the hard work to get where I am. I didn’t back stab, lie, cheat, our steak my way to where I am now.

    Also I think realizing ( and remembering) where you’ve come from and how easily you could be back there keeps you both humble and appreciative, which is a great thing.
    Shirria @ GDTH recently posted…3 helpful tips to save time in the morningMy Profile

    • Melanie says:

      Money will come your way…hard work does pay off, eventually. I am so appreciative for this change. It’s so interesting the different feelings I’m having though.

  6. NZ Muse says:

    Guilty, yep. Especially since my job isn’t really that hard!

    Fraud, yep. DO I really deserve this?

    Terrified, not quite, but definitely don’t want to go backwards.

    Want to be generous, yep.

    Work harder – ha, definitely not. The irony/beauty of leaving journalism is no longer being overworked and underpaid.
    NZ Muse recently posted…An ode to spousal unemploymentMy Profile

  7. And I read this and think, “If anyone “deserves” to be making more money, it’s Melanie.” You have worked hard to change the direction of your income path and there is nothing fraudulent or quick about that change. I tell clients all the time that they have the ability to make more money and change their financial path, but many of them don’t have the drive and determination to do it. You do, and I am so thankful that it’s paying off for you!

  8. I’ve felt this too, Melanie! For so long, I identified as the low paid person in the music business. And I was making less than $30K for the first few years of my career. Once I started earning more, I didn’t want anyone to know. Maybe I felt like I didn’t deserve it. Or any of the other reasons you’ve mentioned. But we’ve all worked hard to get to where we are. And we should be proud of ourselves, right? We all know how hard you’ve worked. And you absolutely deserve all of the success you’ve seen!
    Kate @ Cashville Skyline recently posted…My Seventh Net Worth OvershareMy Profile

  9. I can sort of understand all these feelings except the guilt for making more one…bring more money on! lol! One of my money issues is if things are going well, I’m waiting for the other shoe to drop. Why can’t I just enjoy it and say I deserve it? So I get where you’re coming from on the other feelings.
    Tonya@Budget and the Beach recently posted…Clarity+Action=ResultsMy Profile

  10. Hannah says:

    I can relate to some of these, but I’m not nearly as self-made as so many in the PF world, so I don’t actually feel like a fraud when I earn money, nor do I have the same level of fear that others express.

    One thing that I’m guessing you’ll learn soon is that you’ll want to continue to earn more money even when you don’t really need to. Earning money can be very addicting and very easy to put your hope in.

    • Melanie says:

      It’s so addicting! Now I want to make six figures lol. Before I would have never thought that was possible, but I want to keep upping my game. At what point is too much, though? And I need to relax and just be happy? It’s tough.

  11. I love this post Melanie! I used to feel guilty and like I wanted to pick up the tabs for my friends when I first finished college. I was working full-time and most of my friends were still in school and only working part-time. I don’t have that problem now as most of my friends are working and can afford their own drinks, etc. Plus I have debt to pay off, so that always keeps me from being as generous as I’d sometimes like to be.
    Kayla @ Shoeaholicnomore recently posted…5 Easy Ways to Reduce Your StressMy Profile

  12. I don’t know anyone who doesn’t feel like a fraud in some way. It definitely feels strange to be making more doing this kind of work than being at an office job, and I’m still surprised from time to time that people are paying me for writing! I also worry about it all ending abruptly.

    I think the first reason is interesting, though. You know you’ve hustled your butt off and your success is well-deserved! I came from a similar background – I figured I was destined for low-paying jobs my entire life. But I don’t feel guilty for earning more now. I’m happy I took action in leaving that “life” behind and forging my own path. I don’t think I’m entitled to it, but I’ve never questioned it, if that makes sense.
    Erin @ Journey to Saving recently posted…Being Grateful: Seventy-Seventh EditionMy Profile

    • Melanie says:

      I totally know the feeling. Wait, people PAY me to write? I thought I was also destined for low-paying jobs, so it feels weird now seeing what’s possible. Good, but still an adjustment.

  13. I love your transparency in this post. Money can evoke so many, emotions. I’ve definitely felt guilty about our income, and I’ve also felt guilty that I’ve chosen not to make money while I’m staying home with little kids. And I’m always torn over how much to be generous and how much to save/invest. I think the struggle means you’re thinking through things, though, and that is so important for both finances and emotions.
    Kalie @ Pretend to Be Poor recently posted…5 Ways to Win Your Lover (to Being More Frugal)My Profile

  14. I TOTALLY get the guilt thing. I’m in the same boat and do the same thing- tend to take jobs that really don’t pay me. Just wondered if you had advice about student loans? Are you on a basic repayment plan? IBR? PAYE? Any recommendations? I am just starting out knocking out my own $40k of loans and hubby will graduate soon with about $400k! yikes!
    Amber Masters recently posted…Debt UpdateMy Profile

    • Melanie says:

      Hey Amber. I’m on a Standard Repayment Plan. I recommend trying to pay off your loans as quickly as possible — for you that may mean being on IBR, but paying more if you can.

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