Your Self-Employment Mentality: The Real Reason You’re Not Making Money

This post is from Careful Cents contributor Erin, who owns the blog Journey to Saving. Over the next six months she’s documenting her backwards journey to self-employment.

Having the correct mentality when it comes to self-employment seems easy when you first think about it, but like many things in life, it’s much more difficult when put into action. If you’re not mentally prepared, you might be taken by surprise.

In the short time I’ve been self-employed, there have been a few large mental hurdles I’ve overcome in order to avoid business depression. I love that Carrie has highlighted this issue because it’s certainly real, and something that we don’t often think about when starting out as a solopreneur.

If you’ve found yourself in a funk with your business, I want to let you know you’re not alone. Self-employment is hard, and takes a thick skin and attitude of perseverance to keep going.

There will be many times you want to quit, give up, get a “real” job, and find work that easily pays the bills but makes you unhappy.

That’s why I’m sharing the wrong mentalities of being self-employed, that I’ve discovered for myself, and how you can overcome them, too.

Wrong mentality #1: Lost in self-doubt

Self-doubt is by far one of the biggest struggles faced by solopreneurs. Imposter syndrome is brought up a lot, and I think I’m in good company when I say it’s because we’re sometimes in disbelief that, as artists and creatives, we get paid to do things we love.

As a result, we wonder if we’re good enough. We wonder if our work really matters. We wonder if we’re making the right decisions.

All this self-doubt can eat away at you, and negatively affect your work.

  • If you think you’re not good enough, you won’t try hard enough to get clients.
  • If you don’t think your work matters, you won’t have the motivation needed to grow your business.
  • If you’re questioning your decisions, you’ll be holding yourself back from taking risks. (You won’t grow as a person or as a business without taking some risks.)

Worst of all, if you’re already doubting yourself, then the doubt of others can seep in. I’m very grateful my friends and family have been supportive of me, but I know that’s not the case for everyone.

Overcoming this mentality: Have confidence. Confidence, direction, passion — these are all important characteristics solopreneurs need to have. Without them, you’ll feel lost, depressed, and possibly worthless.

Those are harsh words, but they were very true for me in the beginning of my self-employed career. Since I began a backwards journey, with no clients, it was difficult to derive feelings of worth when I was making next to nothing.

The best solution that I found is to go back to your “why”. Why did you start on this path in the first place? Figure out if it has stayed the same, or if it has changed.

When you know your purpose and you’re driven, self-doubt rises to the surface less often. It’s not always a question of knowing what you’re doing, but a question of why you’re doing it.

Wrong mentality #2: Feeling guilty

Have you felt guilty for such amazing opportunities coming your way? For being able to get paid to do things you enjoy? This is likely because self-doubt is telling you that you don’t deserve it.

It’s easy to let the guilt get to you, and guilt can often leads to self-sabotaging behavior — which isn’t good for you or your business.

I’m not quite sure where this mentality is manifested from, but I know I’ve felt similarly many times in my life. When good things come my way, I tend to dismiss them. I rarely celebrate. I don’t take time to record what I’ve accomplished. Where’s the fun in that?

Overcoming this mentality: As solopreneurs and freelancers, we work our tails off day in and day out. Whether we’re hustling on the side, or working 60+ hours a week, we’re constantly focused on growth and making a living.

So who are we to say we don’t deserve it?

It’s time to give yourself credit and simply enjoy the opportunities you’ve been given. Stop questioning them, and asking why you’re one of the “lucky” ones, because it often has nothing to do with luck, and everything to do with dedication.

Wrong mentality #3: Thinking work is scarce

Before I explain this one, I want to say this is a perfectly valid mentality to have. Freelancing is often characterized as feast or famine, whether you’ve experienced it yet or not.

But staying in this mentality is only going to do damage, and hinder you from going to the next level. Nothing good comes from mentally closing doors to opportunities.

That’s exactly what happens when you start to say;

Work has dried up. I wonder if I’ll be able to find other clients. There are so many other freelancers out there who offer the same services as I do. What makes me any better?

That negative self-talk is only going to make you less likely to pitch your services confidently, or want to go out and try at all.

Overcoming this mentality: Be a go-getter! Take a leap and the net will appear. Have faith that there are enough opportunities to go around. I’ve recently started to turn down work, and I’ve only been at this for about five months.

There’s been a huge shift to developing an online presence for businesses, and that means there are plenty of opportunities for those in content marketing, social media, web design, SEO, copywriting, etc.

Instead of locking yourself into the scarcity mindset, take stock of the work you have had over the past few months. Realize you’ve been able to make things work so far, and that’s no small feat.

Then realize there’s no reason you can’t keep going with it! Make your own opportunities. Reach out to people in your network — if they don’t know you’re looking for work, how can they send it your way?

Wrong mentality #4: Having limiting beliefs

Have you ever had an idea you were excited about, but brushed it off as unrealistic? Have you thought, “There’s no way.” “I can’t  — that’s impossible!”?

Have you been 100% positive you were meant to do something, but can’t pull the trigger because you don’t think it will work out? (We’re all guilty of this one.)

These are all examples of limiting beliefs. You’re directly limiting your opportunities and closing yourself off to possibilities because you don’t think they’ll translate to reality.

Not everything goes according to plan in life, sure, but how many times are you going to let that stop you? That’s not what makes a successful solopreneur.

Overcoming this mentality: The best thing to do is to get over it! Accept that things might not work out, but it’s worth a try anyway.

Many of the successful entrepreneurs you see in the media had crazy ideas at one time, too. The thing is, they acted on them.

If you feel called to do something important, to make a difference, or to help others, then do it. I’m not saying go all-in blindly, but stop letting limiting beliefs hold you back! All of us have amazing potential, we just need to unlock it.


I hope that addressing these wrong mentalities has been helpful to some of you. It’s so easy to get caught up in our thoughts at times.

But the important thing is to keep barreling through the negativity to get to where you want to be. Don’t be the obstacle that stops you from trying.

Have you ever been guilty of any of these mentalities? How do you get out of your own way?

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Read Comments

  • Comment Author image blank
    I am completely guilty of believing that work is scarce and there's no way there's enough to go around for everyone who wants to do what I do! I've really had to learn to have faith in myself, but I still struggle with that. This was a great reminder to keep me on track :) Thanks for the wise words, Erin!
    • Comment Author image blank
      Thanks, Kali! It's definitely easy to fall into that trap, but reading about the success of others has shown me that we can all make a living by doing similar things as we all have something different to offer. Having faith in your unique abilities really helps!
  • Comment Author image blank
    I am having trouble keeping up right now because there's so much work to be had, but I used to wonder about the scarcity of work for freelancers. I know you still have to be a go-getter to stay busy for a long period of time though, especially if freelancing is your FT job (or only job).
    • Comment Author image blank
      Good to know others are having a similar "problem"! I think it comes down to finding a groove and getting started. Things get easier as you progress and learn.
  • Comment Author image blank
    I so needed this post Erin. Thank you so much.I´ve been a full-time freelancer for about two months and I find myself struggling with limiting beliefs and feeling guilty. Your article is exactly what I need. I´ll print it and put in my office. Thank you.
    • Comment Author image blank
      Oh wow Corina, that's a huge compliment, thank you! So glad my words could help. =) Just know you have a whole community of us behind you if you ever need to connect - freelancing can be isolating, and I've found talking with others helps me gain clarity and stay sane!
  • Comment Author image blank
    wow. erin, i think you are in my full set of emotions and head space! your words are spot on, and cover so much of what i go through every day. thank you thank you thank you. this one is a going to be a constant re-read for me. best—susan
  • Comment Author image blank
    J.P. Choquette
    Great article--I could relate to so many of these "icky" mentalities. I also appreciate all the links to other subject (I know most if not all blogs do this, but to me it's like getting a prize in the bottom of my cereal box). I especially liked what you said about recognizing/celebrating what we've DONE instead of constantly worrying about what we haven't. Thanks!
  • Comment Author image blank
    I have been guilty of many of these. Once I started to actually value my work and time though, things have gotten much easier.
  • Comment Author image blank
    Jeffrey Hill
    Whew, this post really hit home. I'm in the early stages of self-employment (freelance writing) and I've struggled with every single bit included in this post. And it really ebbs and flows. Some days its daisies, sunshine and hope - other days its darkness, clouds and self-doubt. Just discovered your site and I'm really glad I did. This post is still helping people over a year after it was published. ;)
    • Comment Author image blank
      Hi Jeffrey, thanks for commenting! I'm glad the post was helpful and offers information to help you overcome some mindset issues. That's the biggest part of being self-employed, so when you can overcome that you'll be able to accomplish great things. :)