Starving Artist No More Blog

012: Be Willing to Be Bad at Business

daily habits entrepreneurship gratitude mindset money management Jan 17, 2023
Starving Artist No More | Jennifer Jill Araya
012: Be Willing to Be Bad at Business

As artists, we are good at our craft. We’ve spent years honing and perfecting our skills, and our art is an area of our lives over which we have mastery. Sure, we’re always learning and growing, but the refined skills are there. When it comes to our art, we know what we’re doing. But being a creative entrepreneur is about more than just our art; that pesky little “entrepreneur” part is tagged on there. What about the entrepreneurial skills and concepts we need to be good at that part of what we do? They’re a little harder to come by. Today, we’re going to talk about how you can acquire the business skills you need to be a thriving creative entrepreneur, but I’ll give you a quick hint: it starts by being willing to be bad at it. In order to be good at business, you must first be willing to be bad at business.


Hello and welcome, thriving artists! This is episode 12 of the Starving Artist No More podcast, and I am your host, Jennifer Jill Araya. I am so glad you’re joining me for today’s discussion about being willing to be bad at business. I’m excited to share with you my thoughts around the skills and abilities you need to grow your business.

But first, I want to mention that I have a free resource available for you on my website, If the business side of your business is something you struggle with, then you probably also struggle to manage your business finances, and I really think this resource can help. You can get the free guide, titled “Say Goodbye to Feast or Famine: Three Financial Must-Haves for Creative Entrepreneurs,” by filling out the form on my website. The guide will walk you through three incredibly powerful steps you can take to better manage your business finances so that both you and your business can thrive. Just navigate to and fill out the form to get the guide sent directly to your inbox.

And with that, let’s jump right on in to the topic of today’s episode: be willing to be bad at business. The concept for this podcast episode came to me when a friend sent me an article by Austin Kleon. Austin Kleon is the author of the book Steal Like an Artist, which is on my 2023 business reading list, and he also wrote the companion Steal Like an Artist Journal, which I’m going to be working my way through during 2023. (In fact, I filled in my second page just last night.)

At any rate, back to the article. The article my friend forwarded to me is titled “30-Day Challenge,” and it’s all about the importance of consistency in mastering any craft. You’ve probably heard the story of Jerry Seinfeld’s daily practice of writing jokes. Every day, he writes a joke and then puts a big X on the calendar for that day’s date. As Seinfeld says, “After a few days you’ll have a chain. Just keep at it and the chain will grow longer every day. You’ll like seeing that chain, especially when you get a few weeks under your belt. Your only job is to not break the chain.”

This is such good advice for how to improve in your craft and how to grow your skills as an artist! There are several habits related to my artistic work that I maintain on a daily basis so that I can make sure I am always growing and evolving as an artist. I enjoyed reading Kleon’s article about the importance of daily habits for artists.

But this was all information I’d heard before. Seinfeld’s “Don’t Break the Chain” method of working to get better at something has been talked about widely since early on in his career. I’ve read numerous other articles and books that reference the concept. I appreciated Kleon’s article about it, and it was a good reminder of important principles about growing and improving as an artist, but it didn’t tell me anything new …

… until I got almost to the end of the article, and Kleon wrote something that really hit home for me. Here’s what he said: “To get good at something, you first have to be willing to be bad. So don’t practice to get good, practice to suck less!”

I read that line, and I had to read it again and again a few more times to really process what it meant. It really struck a chord with me. To get good at something, you have to first be willing to be bad. So don't practice to get good. Practice to suck less, to be less bad.

As creatives, we're used to being excellent, to pursuing perfection, in our art. I’ll use myself as an example. Bouts of imposter syndrome aside, I know I’m good at my craft. I have studied and applied myself for years to build the performing and acting skills I use every day to do what I do, and I know I’m good at it. That doesn’t mean I’m content to rest on my laurels; I’m always working to improve at what I do, to get as close as possible to that unattainable descriptor of “perfect” in my work. I’m never satisfied with where I am and always want to keep growing as an artist. But I also have the confidence that comes from being a working artist who has spent my entire life learning to do what I do. I know I’m good, or I wouldn’t be working to make a living doing it.

I would imagine you can say something similar about yourself. Sure, you might struggle more with certain aspects of your craft than with others – what artist doesn’t? And I have no doubt that you deal with attacks of the imposter syndrome monster sometimes, like we all do. And sure, you are almost certainly better at certain techniques or in certain areas of what you do than in others. But you’re probably very rarely truly, completely, totally bad at your art. You might have an off day now and then, but you’re not bad at what you do. Otherwise you wouldn’t be doing it. As artists, we're often not used to being less than good, and certainly we're not used to being bad at what we do. The pursuit of excellence is such an integral part of what it means to be an artist.

And yet, so many creatives are bad at business! We excel in one area, in our art, but that mastery goes out the window when it comes to our business. Balance sheets – what’s that? Financial management – help me, please! Marketing and advertising – how do I do this? Project management – I’m floundering!

As a whole, we creative entrepreneurs are bad at business. It’s not something that many of us were trained to do, and we don’t know what we don’t know. We often struggle with the basic skills we need to manage the business side of our business. And when we are so good at another aspect of our work, the creative, artistic aspect, it’s really hard to swallow that we’re so bad at something else that is so integral to our lives as artists.

However, that comparison leaves out something really important: we forget that we weren't always excellent at our art. Sure, we may be excellent at our art now, but that wasn’t always the case! We had the same awful beginnings and cringe-worthy kid performances as everyone else. We were bad at our art long before we were good. The difference is that we kept working at it day after day, week after week, year after year. We sought the help of teachers or mentors or training programs. We practiced and we learned, and then we practiced and learned some more. Before we were good at our art, we were bad, and we kept doing it anyway.

Now it’s time to do that for the business side of our work. We need to practice and learn, and then we need to practice and learn some more. We need to be ok being bad at business, and when we are bad, we need to keep doing it anyway. We can’t expect ourselves to be good at business, especially not at the beginning.

Many creative entrepreneurs that I know stick their head in the sand and ignore the parts of their business that they find difficult and that they lack the skills to handle. When it comes to the business side of their business, they do what they know how to do and ignore the rest. But this isn’t a productive strategy. There’s a reason the phrase “stick your head in the sand” has a bad connotation!

I want you to build a business that is thriving and that will support you for years to come in all of the ways that you need support: personally, creatively, and financially. You can’t do that if you ignore everything about your business that you can’t complete easily.

But when you first start to address those tough areas of your business, you’ll probably struggle. Scratch that – you’ll definitely struggle. After all, if those business tasks were easy for you, you’d have been doing them all along, and they wouldn’t be “tough” for you. So this is where you need to be willing to be bad. Be willing to start, even though you feel like you’re making a mess of things. Be willing to attempt the tasks that are your stumbling blocks. Be willing to be bad at them. And as you go, don’t worry about being good at those tasks. Just focus on being less bad. Work at them so that you suck less. Practice your business skills the same way you practice your artistic skills.

I hear you asking me: “How do you practice to get better at business? I know how to practice and improve in my artistic craft, but I don’t have a clue about how I can practice at business.”

Never fear. I’m going to give you some strategies so you can practice being less bad at the business side of your business.

The first and most important part of practicing at your business, of being willing to be bad, is to accept that you are going to have to do things before you’re ready. You’re going to have to take action even when taking action is the absolute last thing you want to do, and when you don’t feel ready to do it. Most creatives will never feel completely ready to take action in their business, so if you wait until you’re ready, you won’t ever do it. Do it before you’re ready. Be willing to do it, even though you will most likely be bad at it.

It's the third week of January when this episode is being recorded and initially being released, and my 2023 strategic plan for my business is fresh in my mind as I’m working on this episode. Even for me, a creative entrepreneurship coach, there are plenty of actions that my business goals require me to take that I don’t feel at all ready for. One of my priorities for my business coaching business in 2023 is to write, film, and release a full suite of online courses about various aspects of creative entrepreneurship. I’ve taken plenty of online courses in my life, but I’ve never produced one myself! This is something about which I know next to nothing.

I absolutely do not feel ready to leap into this project and see it through to completion, but I’m going to do it anyway. I’m going to work on those online courses, even though I don’t feel ready for it. I’m going to be willing to be bad so that I have the opportunity to learn and grow and improve, and hopefully, at the end of that iterative process of practicing and learning and growing and improving, I’ll have a good product that I’m proud to release into the world. But if I’m not willing to do it before I feel ready, if I’m not willing to be bad, then I won’t ever get started, and nothing will ever happen and nothing will ever change, and the end of 2023 will come and I won’t have a suite of online courses available to help creative entrepreneurs as they work to build a business that meets their needs. None of the good things I have in mind can happen without the first step: me doing something before I feel ready to do it.

When you’re looking at a big looming task in your business, one that you don’t feel ready to tackle, what internal block is telling you that you’re not ready? What keeps you from making change? What excuse do you use? My most frequent excuse when I’m faced with a business task I don’t feel ready to handle is “I don’t have time,” but most often, that’s not actually true. I do have time to do the hard things that will get my business moving in the direction I want. I have time to dive into the monumental task of developing that suite of online courses I mentioned.

But I procrastinate. Instead of working on the “online course” tasks on my to-do list, I fill my time with unimportant, non-urgent tasks. It’s my way of avoiding – of procrastinating – on the hard things I really need to do.

What excuse do you tell yourself? Doing some self-examination work in that area may allow you to figure out ways to help yourself feel more ready to take on these difficult business projects.

But the truth is that even with that internal work, there are just some business tasks that you’re never going to feel completely ready to take on. Some business undertakings just feel so big and so overwhelming to us that even if we do all the mindset work to examine and address our hang-ups and excuses, we’re never going to feel fully equipped and fully prepared to take them on. It’s a fact of life that the “entrepreneur” part of being a creative entrepreneur is going to force you to stretch and grow in ways you don’t want to, and don’t feel ready to, stretch and grow.

What do you not feel ready to do in your business? If you did year-end goal-planning for your business a few weeks ago and worked on a strategic plan for this year, what actions are required by that strategic plan? Are you ready to take those actions? If your answer is no – which, if you really took the time to put together a strategic plan for your business that stretches you and forces you to grow in truly amazing ways, then your answer should be no, at least for some of those actions – if your answer is no, that you do not feel ready to take those actions, then I encourage you to get started anyway. Don’t wait until you feel ready to move your business forward. That’s a recipe for never going anywhere with your business. Take action before you’re ready. Be willing to be bad.

Once you’ve taken that first step, that of getting started before you feel ready, the next thing to focus on is your mindset as you’re doing the work, as you work on those pesky “trouble” spots in your business. Change your mindset from one that fears failure to one that rejoices in failure. Failure is a good thing! Failure means you’ve determined what doesn’t work, bringing you closer to what does work. As Thomas Edison famously said, “I have not failed 10,000 times – I’ve successfully found 10,000 ways that will not work.”

When you take that scary leap and try something in your business, only to have that thing not work out the way you’d hoped, you have not failed. You’ve just determined what doesn’t work so that you can eventually determine what does work! And you wouldn’t have ever figured that out without first trying and failing. You don’t know whether or not a given strategy in your business will work until you try it.

Figure out what all of the wrong marketing strategies are for your business so that you can eventually identify one that is right. Take the risks that allow you to determine what projects are the wrong types of projects for you so that you can figure out what projects are the right ones, which ones do fall within your creative and financial sweet spot such that you are doing your absolute best work and being paid your highest rate while doing so. Discover the project management systems that don’t work for you and your business so you can figure out what you do need from a project management system and can find one that meets all of your criteria. Learn what administrative tasks aren’t necessary for your particular business so that you can see what administrative tasks are truly necessary for your business to grow and thrive.

When you take a risk and it doesn’t work out, this is not a bad thing. This is a good thing. You now have more data with which you can make informed decisions the next time around. Your old, failure-averse mindset will try to drag you down by telling you that you’ve failed and that you’re a failure. Yes, you’ve failed, but that doesn’t make you a failure. Rather, that makes you a risk-taking, adventurous, growing, and learning entrepreneur. That failure has given you valuable information that you need to succeed in the future. It may be easier to never try, since that means you’ll never fail, but it also means you’ll never learn and you’ll never grow. Trying and not succeeding is always better than not trying at all.

The more you try and try and try again, and the more ways you find that don’t work, the closer you will be to finding the processes and systems that do work for you and your business, but I want to caution you: don’t get discouraged if you don’t see immediate results. Be content with gradual growth as you build your business skills. Don’t expect yourself to go from bad to good immediately.

Friedrich Nietzsche said, “He who would learn to fly one day must first learn to stand and walk and run and climb and dance; one cannot fly into flying.” You cannot expect yourself to jump into the difficult business tasks in front of you and immediately be good at them.

Again, this goes back to our experience as artists. We aren’t used to being bad at something we’re working to do. We’re used to people enjoying our work. We forget that our first recital as a young music student, or our first ever watercolor painting as a 7-year-old, or our first ever sculpture out of kids molding clay made in kindergarten, or our first short story written on construction paper in elementary school, wasn’t what anyone would call a masterpiece. Yes, people love and enjoy our artistic work now, but they didn’t always. We had to work at it. We had to take our raw talent and develop it, cultivating the skills and techniques that make us artists today. We had to be bad at our art before we could be good.

Expect to go through the same process as you work to eventually become good at business. You will be bad at business at first. In fact, you will be bad at business a lot and for a long time, long before you ever become even mediocre at it, and then even longer before you become good. You will try things in your business and they won’t work, or they won’t work they way you wanted them to work. So you’ll try again and again and again and again. You must first stand and walk and run and climb and dance in your growth as an entrepreneur, before you can learn to fly. Your growth will be gradual, but there will be growth. Every day, as you are consistent in your practice at business, you’ll suck a little less. Don’t worry about being good, just focus on being less bad. And you will be a little less bad every time you try and fail and try again, as you learn and grow.  

Being a creative entrepreneur is not always about big decisions and big actions. It’s often about the daily, weekly, monthly practice of taking action on the little things that you need to do, the tasks you need to address on an on-going basis to allow you and your business to thrive. It goes back to Seinfeld’s X’s in a chain on his calendar that I mentioned back at the beginning of the episode. Most artists know viscerally how important daily practice is for maintaining the high level of their craft, but daily habits can help you grow in your business skills, too. What are some daily, weekly, or monthly practices that you can use to keep your business growing and thriving?

To give you some ideas to get started, here are some of my regular practices. Hopefully hearing about the things I do regularly in my business will get your creative juices flowing as you think about how to incorporate habits into your growth and learning as an entrepreneur. Some of my daily practice tasks include

  • spending 20 minutes each morning writing for my podcast episodes and teaching curriculum,
  • taking care of my voice physically for my audiobook work, which usually includes warming up with vocal scales and exercises, or depending on how I’m feeling and what I have on my recording schedule for the day, it could also mean doing a vocal nebulizer treatment, or just drinking lots of water,
  • taking care of my body physically by working out or exercising, or sometimes just simply moving my body in some way,
  • writing in my gratitude journal so that I am able to keep myself positive and motivated about my creative work, which is a practice I talked about at length in episode 4 of this podcast,
  • staying current on my project management tasks so that I make sure I’m completing the things I need to complete that day for the creative projects currently on my plate, and
  • reading for a bit each night out of that month’s business growth book (which is something I’ll talk about more in a minute)

On a weekly basis, I make sure to

  • put together my weekly task list on Sunday night so that I know what my business priorities are for the week,
  • stay current on the networking and reach-outs required for both my business coaching business and my audiobook business,
  • check audition listings from the audiobook publishers and producers I work with so that I can submit myself for any audiobooks that might be right for me and my voice,
  • send out my newsletter for the week – I send out a narration newsletter every other week, and I send out a business coaching newsletter every other week, meaning that each week I’m writing and sending one of my newsletters so that I’m staying in touch with both my audiobook listener fans and the creative entrepreneurs who are part of the Starving Artist No More community, and
  • this last one I only do every other week, but I balance my business banking accounts, pay my business bills, send any invoices that I need to send, and make my budget category allocations based on the percentages that I’ve determined work for my business, following the process Mike Michalowizc outlines in his book, Profit First.

Every month, I do a monthly review. I take four hours out of my workday, either at the very end of the month or at very beginning of the next. My monthly review includes things like looking back over the projects for the past month and making a note of what projects creatively fulfilled me, and which ones didn’t. If there were any changes I could have made that would have made those projects more creatively fulfilling, I make note of that so I can incorporate that in the future. I think back over my marketing and networking efforts for the past month and evaluate what worked and what didn’t so that I can make adjustments to my marketing strategies as needed. In general, I look at the actions I took in my business and evaluate what worked and what didn’t. I want to learn from both the good and the bad as I’m planning for the coming month. Remember, if I failed at something, that doesn’t make me a failure. I just means I’ve found a strategy that doesn’t work, bringing me closer to finding one that does.

So using everything I learned in the past month, I look over my business’s strategic plan for the year and figure out when and how I’m going to do the things I need to do for the coming month to take advantage of the learning that happened in the past month. I create a map of the month for myself of what and how I’m going to approach in that coming month so that I can make sure I’m learning and growing to the best of my ability.

These are some of the daily, weekly, and monthly practices that work for me. What are some daily, weekly, and monthly practices you can establish for yourself that will help you grow as both a creative and as an entrepreneur? If you’re not worried about being bad at them, if you take away that mental block, what practices would you want to incorporate into your experience of being a creative entrepreneur?

So far, everything that I’ve talked about, all these tips for how to practice your business so that you can learn and grow and be less bad at it, are things that you do on your own. Doing things before you’re ready; changing your mindset so that you view failure as a good learning experience; expecting gradual growth rather than instant growth; and establishing daily, monthly, and weekly business growth strategies for yourself are all things that epitomize the “solo” part of “solopreneur.” But you’ve heard me say before that no man is an island, and no creative entrepreneur is an island. You and your business do not exist in a vacuum. You are not alone.

You can do all the things I just mentioned, and it will help you to grow as an entrepreneur, but it won’t take you the full distance. You can’t do this creative entrepreneurship thing by yourself. As creative entrepreneurs who are artists first and who are business owners second, frequently getting into the “business” side of things almost by happenstance, when it comes to our business, so often we don’t know what we don’t know. We have “unknown unknowns,” things we don’t realize we don’t know and that have the potential to come up and catch us unawares because we don’t even know enough to watch out for them.

Business is hard. There’s a reason that some people major in business in college, or spend their whole careers studying business and economics. And we don’t need to have that level of mastery of business concepts as a whole to be successful creative business owners, but we do need to do enough study of business to minimize our “unknown unknowns” so that we’re able to handle the ups and downs when they come. And in almost every case, we need other people to point out those “unknown unknowns,” to help us in our study of business.

Seeking support from those around you is the difference between truly growing and thriving and building a creative business that works, and simply existing as a creative business owner. There are lots of ways you can get the help of others, whether that’s joining Facebook groups or other social media groups for creatives in your industry, or being intentional about forming friendships and accountability relationships with colleagues in your industry or in your geographic area, or seeking a mentor to help guide you as you grow.

One of the best business decisions I ever made was developing a business accountability relationship with my two accountability partners, both of whom are amazing audiobook narrators and who are walking this creative entrepreneurship journey with me, and who also happen to be two of my best friends. I’m a member of several Facebook groups where I can get questions answered when I need that kind of support. And I’ve worked one-on-one with incredible business coaches and gone through some amazing group workshop programs that helped me identify those “unknown unknowns” in my business so that I could address problems in my business before they popped up.

If that last option, coaching and workshops, is something that interests you, I offer a one-on-one coaching program that is specifically designed to give individualized guidance to creative entrepreneurs who want to build a creative business that meets their needs: personally, creatively, and financially. I also offer a 3-month group workshop that provides wonderful group accountability and a supportive learning environment for creatives who want to take their creative business and help it grow into a business that truly works and that gives them the support they need. In fact, when this episode is originally releasing, the next session of my group workshop program starts next week, on January 25, 2023, and if you’re interested in joining in on that session of my group workshop program, you can find all the information on my website,

But I’m not the only creative business coach out there. If my offerings don’t seem like what you’re looking for, I encourage you to find a business coach or mentor who can help you in the way that you need. Working individually with someone who is further along the path you’re hoping to travel can often help you precisely pinpoint your individual “unknown unknowns” as it relates to your creative business so that you won’t have any roadblocks in your way as you work to grow and learn and thrive as a creative entrepreneur.

That said if a formal coaching, mentorship, or workshop program isn’t what you’re looking for right now, a less structured option is to get coaching from books. Yes, I’m an audiobook narrator and self-confessed book nerd, so books are almost always my go-to, but in this case, turning to books can make such a huge difference! You can use books to address your lack of knowledge about business.

Make a reading list for yourself of specific books that teach about the area of business that you’re currently struggling in, or the business topic that you simply feel like you don’t know enough about, and get “coaching” by working your way through those books and learning in the process. This is something I’ve done for several years now, and it has perennially been one of the most helpful tasks I’ve given myself in my business’s yearly strategic plan. Each year, I pick a topic to focus on for the year – past topics have been things like productivity and task management, project management, business financial management (which is the year I first read and implemented the Profit First system in my business, which was the single best business decision I ever made), and strategic planning and goal setting. Once I’ve selected a topic to learn about for the year, I then pick 12 books on that topic, one for each month of the year, and I read a little bit out of that month’s book every night before I go to bed. This business-focused reading plan has taught me so much and has allowed me to grow in amazing ways as a creative entrepreneur. My business reading plan this year is focused on marketing and branding, and I’m so excited about all of the ways I am going to improve my business knowledge as a result of the books I’m going to be reading over the next 12 months.

As a little sidenote, if you’re interested in my yearly business reading plan and would like me to talk more about it on a future episode of this podcast, let me know. I’m not necessarily planning to do that right now, but if you let me know that this is something you’d like to know more about, I’ll put an episode on that topic into my podcast episode lineup.

All of these strategies I’ve talked about today – doing things before you’re ready; changing your mindset so that you view failure as a good learning experience; expecting gradual growth rather than instant growth; establishing daily, monthly, and weekly business growth strategies for yourself; and seeking support from others – all of these things start with you first being willing to be bad. Don’t expect or require perfection from yourself in your creative business. Yes, strive for excellence in everything that you do, and especially in your artistic work. But be willing to try something out even if you’re bad at it. The only way to eventually get good at something is to first be bad at that something. You have to start somewhere. Don’t judge your starting point. Be willing to be bad at business. It’s the first step to eventually thriving.

Thank you so much for your time for this episode of the Starving Artist No More Podcast. I really hope today’s discussion helped broaden your perspective of what it means to be “good” at your work as a creative entrepreneur and helped you to know that you don’t have to be good at this whole “business” thing right away – or ever, for that matter! What’s important is that you make the attempt, not how good or not good you are at the tasks along the way. As always, I would love to hear any feedback or comments you have for me about this episode, or any episode, of this podcast. You can reach out to me via my website, If you found this podcast helpful, I would really appreciate a rating, review, or subscription, as that’s how listeners find new podcasts like this one. I wish you a wonderful week full of growth and learning in your creative business, even if that involves you being bad at the business tasks you’ve set before yourself. I can’t wait to see what you create.


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