30 Warning Signs That Spell Failure for Your Creative Business

You’ve probably wondered if you have what it takes.

Is your creative business doomed?

Is your creative business doomed?

You love creating, whether it’s plucking out a story or a song, producing a new show, capturing a sunrise to preserve a moment forever, or crafting that silver into wearable art.

But when it comes to making good money at what you do?

That’s a different story.

There are so many things that you’re juggling, and they’re all important.

It’s easy to let things the things you don’t like to do slide, to rationalize or make excuses, or to tell yourself you’ll get around to them someday.

On top of that, you have to deal with all those nagging fears and doubts –

  •  “I’m not good at business,”
  •  ”I don’t think I can ever learn to manage all this,”
  •  “There’s just no money in music/photography/poetry,” or the big one,
  •  “Does it really matter what I do? Would anyone even notice if I quit?”

We’ve all been there.

The hard truth? You can’t know for sure

I can’t tell you if you have what it takes to reach whatever success means to you. No one can. But the reality is that there are warning signs that your dream business is on shaky ground, and it wouldn’t be fair for me to lie and tell you otherwise.

These are some of the most common mistakes creative entrepreneurs make. Many of these are traps I fell into myself at one time, and some I still work on.

The good news is that none of these signs are a death sentence and all are fixable – but don’t fool yourself. They are critical. If you ignore any of these areas long enough, they’ll cause a great deal of pain and heartache – and maybe spell the end of your dream.

As you read through these points, understand that none of these make you a failure personally. They just mean that your business could fail if you don’t take them seriously.

Signs you’re sabotaging yourself

Do you ever feel like you’d do just fine if you could only get out of your own damned way? Here are just a few ways you might be holding yourself back.

1. You let doubt paralyze you

You’re uncertain, inconsistent, and haphazard when it comes to getting your work out into the world. You waver in your commitment and don’t take your calling seriously. You let the highs and lows of being artistic and creative get to you – and as a result, you don’t put out a constant stream of work.

2. You try too hard to be noticed

You come across as desperate and needy when you’re networking with peers or influencers. Maybe you’re not consciously aware of it, or maybe you realize too late that you wish you had approached a conversation or introduction differently. You focus on thoughts like, “If only I could get this person’s attention, I know they’d help me,” “If only they saw my work, I know they’d love it,” “If only I had an agent/manager/an appearance on America’s Got Talent, my troubles would be over,” etc.

3. You don’t keep your promises

You give your word to your customers, clients, peers, mentors, family, or yourself but then don’t follow through. You haven’t built a reputation of trustworthiness and you’re okay with that. You tell yourself it doesn’t matter.

4. You long for the glory days of the past

It’s true, music venues don’t pay like they used to, the gallery system has changed, and traditional book publishing looks nothing like it did years ago. The world and the economy are different. But you spend more time on wishful thinking than on adjusting to the new realities.

5. You wait for inspiration

You only work when the muse hits you, instead of sitting down at the same time every day to work.

6. You procrastinate instead of doing what you know needs to be done

You have a litany of excuses and stories that you tell yourself and others about why you just can’t get your work done, why you can’t get organized, or why you can’t find time. But if you’re honest with yourself, you know there are distractions you could cut out or ways you could better manage your time.

7. You’re not persistent

You give up quickly when situations get too difficult, instead of finding ways around, over, or through constraints and roadblocks. You don’t persevere, and you interpret hardships as a sign that you should be doing something else.

8. You can’t ask for help

You try to be Superman or Wonder Woman, and struggle with asking for guidance or assistance from friends, peers, or mentors. You try to do everything yourself, even minor things, when you know your time is probably better spent on strategic activities that will grow your business.

9. You have no clear vision for your life or future

Lewis Carroll said, “If you don’t know where you are going, any road will get you there.”

You haven’t taken the time to spell out your goals for your personal life or your business. You take a meandering approach, just reacting to opportunities, with a vague sense that you’re not really where you want to be.

10. You don’t communicate your mission, your passion, or the reason you are driven to create

You don’t know or can’t explain why you do what you do or why it matters to other people. You wish your audience was more excited about your work – but at the same time you’re afraid to stand for anything. You try to make everyone happy and to be all things to all people.

Signs you lack perspective on your craft

It can be hard to see yourself as others see you. You might be harder on yourself than you would be on friends who are in the same situations, or you might be wearing rose-colored glasses when it comes to your skill level.

11. You know your work isn’t good enough yet but you won’t change your approach

Your skill level isn’t where you’d like it to be, but you’re not seeking out the best resources you can find, studying with the best teachers you can afford, practicing by yourself, or putting your work in front of your audience. You either avoid feedback completely, resist any feedback that’s not good, or take everything everyone says to heart and become confused trying to act on it. You’d rather stay comfortable.

12. You’re overly confident

You don’t continuously learn about your craft or business. You think that because you have so much experience that you don’t need feedback from experts. You blame your lack of success on situations outside yourself, like you’ve just never been in the right place at the right time.

13. You don’t share your work because you’re embarrassed

You lack confidence and you let that fear stop you from showing your creative projects to anyone. As a result, you’re not growing as an artist. You don’t see that growth comes from moving ahead despite your fears.

Signs you don’t really understand marketing

There have been plenty of unscrupulous businesses who have given marketing a bad name, but without it, you can’t sell your work. Have you experienced any of these pitfalls?

14. You see marketing as sleazy

You’re afraid to come across as a pushy car salesman. You don’t see yourself simply as an artist who is communicating and building genuine relationships with friends who need what you offer. You tell yourself that you hate marketing, that you’re no good at it, and that it somehow cheapens your work and diminishes your ability to be truly creative and artistic.

15. You have no email list or a small, neglected one

You know you need to build your list but you haven’t taken it seriously. You offer no value outside of newsletters or updates, and you have no irresistible incentive for people to sign up to your list.

16. You haven’t communicated with your email list for months

You think about it, but you just never get around to it. You’ve become a bit complacent and comfortable doing business as usual, and you just can’t make yourself get in there, come up with something interesting and engaging to say, and hit the “send” button.

17. You waste huge amounts of time on social media

You parrot what you see others doing on Facebook, Twitter, Pinterest, or Instagram, without any clear strategy. You have a vague goal of trying to increase sales or get people to come to your events or shows, but you proceed without bothering to try to learn to use social media effectively.

18. You don’t have business cards

When you talk to people in person, they’re supportive and interested in what you’re doing. Then they ask for your card, but you don’t have one. You don’t appear to take your business seriously and have no way for people to follow up with you, sign up to your list, or keep in touch.

Signs your online presence is weak

Your website matters. New fans, whether you meet them in person on online, will want to learn more about you and keep in touch. You need a way to foster that relationship. You could be missing opportunities if you say “yes” to any of these points.

19. You’re ashamed of your website

The last time you made any major changes was 7 years ago when a friend who knew HTML helped you out. You suspect your site is confusing to people and you’re sure it could be optimized but you let uncertainty and indecision keep you from doing anything about it.

20. Your updates and posts on social media are mostly about yourself

You let people know what you have and what you’re doing, but you don’t try to figure out what resonates best with your followers. You don’t ask what things they most want to hear or learn from you or what they love most about what you do so you can give them more of it.

21. You’re not getting a reaction

You have few comments and very little interaction, excitement, or engagement on your blog posts or social media profiles. You don’t know how to increase that interaction or grow your web traffic so you just keep posting on your own sites and hoping that someday it will take off. Secretly (or not so secretly) you suspect that what you’re doing isn’t working.

22. You don’t update your website consistently

You don’t post new content regularly or keep your pages up-to-date. You won’t consider blogging or video blogging to build relationships with your audience, establish your expertise with the visitors to your site, or to help them decide that you’re the person they want to work with or buy from. Your site looks much the same as it did a few years ago.

23. You don’t own your own domain name

Your site is hosted as a subdomain on another larger site, or your main web presence is your social media profiles. The minute the company that owns your site goes out of business or decides you did something inappropriate, your website could be lost.

24. You don’t have a website at all

You know that it’s so easy today to have an affordable, professional-looking website, yet you resist. Maybe you can’t get past the technical barriers. Or – maybe you have a vision in your head of the most perfect, amazing site ever but you think that you can’t get what you really want, so you’d rather have nothing.

Signs you have unhealthy attitudes toward money

Make sure that these common traps aren’t holding you back from earning a good income.

25. You don’t know what it is that makes people open their wallets and buy from you

You don’t fully understand the emotions that make people act, the benefits they get from your work, or the value that you offer them. As a result, you’re unable to tap into those emotional drivers and increase your sales.

26. You are a master of one-night stands (when it comes to sales)

You have no marketing materials or systems in place to follow up with buyers that make it easy for people to remember you, find you, and buy from you again. You look at shows or events as one-shot sales deals instead of the beginning of a great, long-lasting relationship.

27. You underestimate the length of time that it takes to build a business that can support you

You only want to do your creative work and so you’re relying on one income stream, but you’re barely making it. You’re ready to throw in the towel because you think it can’t be done.

28. You’ve rarely sold anything outside of family and friends

You’re afraid to make offers or to ask for money for your work. Somewhere in the back of your mind, you might believe you don’t deserve to be paid well.

29. You don’t make it easy for people to buy from you

You have completed work, but it’s not organized or easy to find or explain. Potential customers don’t buy because you either have too few choices or because they’re overwhelmed. You base your product offerings on what your competitors are doing. You don’t have an exclusive, high-end offer because you don’t believe you can create work that’s worth a higher price tag.

30. Your books, customer lists, accounting systems, and follow-up systems are a mess

You feel like you’re constantly reacting and fighting fires. You’ve got stacks of unsorted papers just piling up. You’re always scrambling and racing to beat deadlines. You know that any increase in business would overwhelm you. You don’t have the systems in place for growth.

What this all means

I’d love to tell you that making money in creative fields is easy. I’d love to give you permission to spend all your time on social media because it will help you grow a fantastic, thriving business. I’d love to give you an “easy button” that puts cash into your bank account while you sleep.

Heck, I’d buy that “easy button” myself! 😉

But that’s not how it works, and that’s not really what you’re here for either.

I’ve made many of the mistakes on this list. I learned, I persevered, I found great people to help me – and you can do the same.

If you’ve read this far it’s because you care. You want the real scoop and you’re willing to figure this stuff out.

If you’re wondering, worried you don’t have what it takes to achieve your goals, that’s a good sign.

If you wake up at 3AM and can’t fall asleep for the same reason, that’s even better.

You’re one of the few who are willing to do what it takes, however long it takes.

If you’re doing good work, I guarantee people will want it.

Don’t give up. It’s a hard road, but it is doable, and the results are so worth it.

So what are you waiting for? Pick one thing you’ve been putting off dealing with and get it into shape.

Get started today!

And if you know you need help, work with me one-on-one. I have a couple of slots still open. None of us does this alone!

Photo credit – Kevin Trotman, FlickrCC

About Leanne Regalla

Leanne is a writer and musician and the founder of Make Creativity Pay. She's on a mission to help creatives of all types to pursue their art without going broke, living in their cars, or starving to death.


  1. Stacie says:

    Just wanted to give you a quick thank you…your writing is wonderful, your messages are completely relevant and helpful, and I really appreciate that you have listened to yourself regarding your gifts and are such a service to those of us that create.

  2. Sumitha says:

    Gosh, Leanna!!! I both hate you and love you for this list. Too many of these hit too close to home to be comfortable, an yet, I needed to read it spelled out so I can “get the hell out of my own damned way!”. Thank you.

  3. Ellen says:

    Great post Leanne, and as Sumitha above, a little close to the bone at times 🙂 Very good reminders to keep us on the straight and narrow (and if you find that ‘easy button’ let us know!!!)

  4. Donna says:

    Excellent post filled with the realities of what it is to “make creativity pay”.

  5. Donna says:

    Pushed my “post comment” too soon. #3 is huge. I have watched several friends try to get a business up and running; who don’t keep their promises. They were all stay-at-home-moms who wanted to start a business; and had good business ideas. They justified it by saying, “People should understand I am busy with my kids”. That’s not living in reality. The only reaction consumers have is that the business didn’t deliver the promise, and they go elsewhere. Business is work, not a hobby.

    • Yes, Donna, great point! I’m not a parent but I do have family, friends, and another business that demand my attention. It’s always a challenge to juggle all the demands on our time and still run our businesses well.

  6. Stephane says:

    Hi Leanne! Thank you for this list, I nearly hit the jackpot: 25 out of 30…

    • Oh, my… Stephane, don’t be too hard on yourself! If it’s any consolation, I also can still say “yes” to some of these now. Many more of these points are things I dealt with in the past.

      The most important thing is that you’re aware. Change doesn’t come over night. Just keep these things in mind and keep plugging away at them. It does get easier, trust me. 😉 And none of us are perfect!

      • Stephane says:

        You are right, I should be kinder to myself, as I’ve just re-connected to my creativity after a decade. I am still struggling to find my own style and that intelligent, non-redundant something to offer to the world, with a reduced impact on the environmenent.
        So I guess I shouldn’t be reading articles about how to market my art before it’s ready! My inner revolution should be over within a few months. I’m coming!

        Thank you for your warm answer, Leanne.

  7. What an extensive list, Leanne! Great job!!

  8. Paul Kaliher says:


    Thank you for your great list of 30 things not to do. It should be a checklist that every creative who dreams of making a living from their work (and any other small business person) refers to in order to make sure they are doing the opposite of each item on the list.

    Though I have participated in the art show and gallery scene, I do agree that things are different now than they used to be. I have made more money writing and self-publishing information products that help creative people and those who want their own home based business.

    Thanks again for a great post.


  9. Stef Gonzaga says:

    I’ve still a long way to go with #’s 25-30, but I’ve a positive attitude towards learning and a strong desire to know all there is about making sales, marketing authentically, and getting my readers to support my work and my vision. That, I believe, puts me a small step higher and one step closer towards my goal as a creative writer.

    Leanne, I can see that you’re offering coaching for creatives who want to take their businesses to the next level. For those who can’t afford to pay for coaching, what would you suggest would be the next best alternative?

    • Good question, Stef. There are actually many options.

      I would follow the people you are interested in working with everywhere you can. On their blogs as well as on social media. Read all the books they recommend. Participate in any free webinars, etc. and make sure you bring good questions to ask. Participate in communities – ask questions and help others. Often you’ll get great advice from the community as well as good feedback from your mentors.

      And actually, the benefit you get from a good mentor will be worth the investment. IOW, let’s say you do some part-time work, or sell something you don’t need anymore, to afford to work with someone. Your mentor should give you practical advice that you can implement right away that will put you on the path to earning more in the future, if not right away (and often it will pay for itself sooner). So good coaching will pay for itself, if you do the work.

      Look at coaching as an investment rather than an expense. But do expect results, not just warm fuzzy feelings. And do test the waters first – meaning, make sure you are getting solid value from a small or no monetary investment before you make the jump to something bigger.

      Hope this helps. It’s a topic that’s on my list to write about. 😉

      And yes, it seems you’re on the right path. Stay the course!

  10. Melissa Thatcher says:

    Excellent post, and very concise. I picked number 10 to work on. Mission, passion, focus…Off to do my work. Thanks for the info Leanne.


  11. Susan Jones says:


    What I love about this Leanne is that you have written the truth in a way that hurts but is palatable. 🙂

    I recognise a few of these from when I used to work as a musician and a composer. And there’s a few that are issues now. (I made a note to go back and look at those. :-))

    Thanks for taking the time to write this.

  12. Leanne, what a great list of things to watch out for! Like others have said already, I’m guilty of quite a few myself . . . but hey, awareness is the first step to overcoming them, and that’s what this post does. I appreciate your candor very much (“I can’t tell you if you have what it takes to reach whatever success means to you. No one can.”), and yes, you have a way of making some very hard truths palatable in a way that gives us hope for meeting them head-on. I agree with Brenda above that this is a great reminder list for the wall or bulletin board. 🙂 Awesome post!

    • Thanks, Michelle! Yes, I’ve seen in my own life many times how much awareness helps. We don’t have to change the world in a day, but change does come when we just open our eyes.

  13. Thank you for this list, Leanne. I scored 9 out of 30. I thought I might totally panic if any of the things on your list was “me,” but looking at my own list, I actually feel better. Now I know exactly where all of my weak spots are, and I have some ideas on how to fix them. A great start would be carrying around the business cards I have so that, when my eye doctor asks where she can find my books, I can just hand her a card. 😉

    • I am SO GLAD you had that reaction, Elizabeth, because that’s exactly what I hoped for! There’s no need to get down on yourself, and it does no good anyway.

      I have been there myself when I’ve run out of business cards… DOH!!!

  14. Stacy Naquin says:

    Great post with tons of information! Guess it’s time for me to go down the checklist 😉

  15. epic fails says:

    First off I would like to say excellent blog! I had a quick
    question in which I’d like to ask if you do not mind.
    I was interested to know how you center yourself and clear your thoughts before
    writing. I’ve had a difficult time clearing my mind in getting
    my ideas out there. I do take pleasure in writing but it just seems like the first 10 to 15 minutes are lost just trying to figure out how to begin. Any recommendations or hints?
    Appreciate it!

    • Thanks so much!

      There are many things you can do to help yourself get started. Everyone goes through this, it’s just a matter of getting a system that works for you. One thing you might try is never sitting down to write without a plan. For example, before you stop writing the day before, give yourself a few points to start with the next day. I suggest having an outline or standard format to work from – it’s not that you can’t deviate from it, but you have a starting place. Try sitting down to work at the same time every day. It’s really all about forming good habits.

      Another thing that helps, if you need 10 minutes or so to warm your brain up, is to do something mindless. Do a few dishes or something, throw in a load of laundry, go for a short walk, but move and take that time to plan.

      Hope this helps!

  16. Gabriella says:

    Leanne, thank you so much, this is a great article and I can already see it’s going to be a brilliant checklist for all the things I have to fix and improve.

    I have a blog in Spanish (my main language) focused on writing and productivity, for writers. I’m sure my usual readers would really benefit from your article, but most of them aren’t great in English. May I translate your article on my blog so they could read it? Obviously I’d link back to your blog and give proper credit, plus any extra information you’d like me to include.

    • Hi Gabriella! Yes, of course… and let me know when it’s done, I have a lot of Spanish-speaking friends who will be interested in sharing it as well. I’ll email you. 🙂

  17. Carlaquarius says:

    Leanne this was fabulous! (And I just happened to wake up at 3am this morning! 😉 )

    Thank you for your mission. <3

  18. Mike Roy says:

    Wow, Leanne, what a cluster of of value-bombs you dropped with this post! I agree with every single one.
    Seeing these all together forces us to take a 30,000 foot view of our creative business and ask ourselves where we are. It’s also amazing how many of them simply require us to get up and take action. When we do, most resistance tends to crumble.
    Thanks for the great perspective.

  19. Some great advice. Finally designed and ordered some business cards after reading this post.

  20. Teri says:

    Thank you so much for doing the research for me! I have some work to do now! Very thorough post! Teri

  21. #26 and #30…ouch. Those are me. Thanks for this great post! I have a new website launching soon…so at least I can take #19 off the list!

    Thanks again Leanne!

    • Good for you, Rachel – and you’re welcome!

      All of this is a process. It takes time to knock all these things off your list. As long as you’re moving in the right direction, you’re in good shape. 🙂

  22. Marjie says:

    wow. Leanna. This is a most painful and compelling post! So many points here apply, and it’s no surprise. But bringing them out into the glaring light invites and encourages a response. I think the business cards need to be addressed immediately; we are a legitimate business and there’s no excuse–no matter how digital we are–for keeping the outdated cards hidden in a drawer. Time to bust this one out!

  23. Jason Meadows says:

    I feel like you can read my mind when I read your stuff. Like all of the thoughts deep inside my brain I fight but never tell to anyone else because I think I might be crazy and know they would never understand, it is all written down in your writing. Haha! It’s good to know I am not crazy and others experience the same things and thoughts as me.

  24. Thank you Leanne. I appreciate all the work you put into helping others.

  25. surinderleen says:

    If I am honest, I can say that your manifesto is not so attractive. However this post is very inspirational. I am wondering you have something that is attracting me to read you.
    May be it is your push to sell my products that could be books! I don’t know.
    Thanks a lot!


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