The Creative Entrepreneur’s Guide To Failing Fast & Forward


It’s a word most creative entrepreneurs don’t want to associate with their business. 

And it’s understandable!

Failure often triggers negative thoughts and memories (especially from school days when we received red pen marks on exams).

It’s no wonder most of us try our darndest to avoid failure and save ourselves the discomfort!

But I want to let you in on some insider information. 

In the mic-drop-worthy words of Arianna Huffington,

“Failure isn’t the opposite of success, it’s part of success.” 

And I’ll be honest. 

When I first saw this quote, the recovering perfectionist in me cringed. 

For DECADES of my life, I had poured tons of time and energy into avoiding failure at all costs!

  • “fixing” a design for the millionth time, only to decide that the original version was better
  • double triple checking my calculations on a straightforward budget report (even though I had them right all along)
  • obsessing over business decisions with a laundry list of pros and cons that still left me paralyzed

Because I didn’t want to mess up or be embarrassed by a mistake! 

You see…

I associated failure with my self-worth. Somewhere along the way I had convinced myself that if I failed at something, I was, by association, a failure.

And it took a long time for me to realize that this deep-set belief was completely FALSE.

In fact, once I started my business I learned, failure is actually inevitable in entrepreneurship.

As soon as I developed a healthier relationship with failure, I was able to see that while mistakes may cause me to stumble temporarily, my failures have the potential to make me and my business stronger in the long run!

The key was to fail often, fail fast, and fail forward

But what does that really mean?

In this guide, we will explore the concept of failing fast and forward so that you can implement this approach in your creative business. Ultimately you’ll develop a better relationship with failure so that you can learn from your mistakes and propel your business forward.

Ready to fail fast and forward in your creative business? 

I promise it’s not as scary as it sounds!

What is Failing Fast and Forward?

Failing fast and forward is a mindset that encourages creative entrepreneurs to experiment, take risks, and learn from their mistakes quickly. 

The idea is to fail early in the process so that you can make adjustments and pivot before investing too much time and money into an idea that isn’t going to work for you or your business.

Instead of fearing failure, failing fast and forward encourages you to embrace setbacks and adversity as a natural part of the entrepreneurial journey. 

When you allow yourself to see failure in this light, you can gain valuable insights that can help you refine your ideas, improve your processes, and ultimately, achieve success.

In my business, this looks like…

  • failing often so that I can get comfortable with NOT doing things perfectly. It also allows me to collect data about all the options that DON’T work. 

  • failing fast, meaning I have learned to course correct when my initial idea stalls so I don’t waste precious time on something that isn’t panning out. 

  • and finally, failing forward (rather than staying stuck) so I can let my mistakes, errors, and misjudgments push me toward the next better idea. 

While every business is unique and each entrepreneur will approach failure differently, there are a few tried and true tips that can make this process feel more attainable and less daunting! 

Keep reading to learn how I coach my clients to successfully embrace and overcome failure!

How To Successfully Fail Fast & Forward

So how can YOU start to approach failure from a new perspective? It all starts with a willingness to adapt, shift your mindset, and commit to the practice!

  1. Shift your mindset. 

    Failing fast and forward isn’t something you can just turn on or off. It’s an intentional mindset. And shifting your mindset takes time and commitment. Unlearning all of your feelings about failure isn’t going to happen overnight! So, I encourage you to be patient with yourself as you reestablish your relationship with failure.  
  1. Take Messy Action.

    One of the best ways to practice leaning into failure is to do things in your business before you feel 100% ready! Often this means you will need to expect to fail, make mistakes, stumble, or figure things out on the fly. Instead of thinking of this as something to be avoided, it can become something you try to do regularly. As a self-proclaimed recovering perfectionist, this has been a game changer in my business. Instead of sitting on a great idea because I don’t feel like it’s totally polished yet, I am better able to put things out there, see what does and doesn’t work, reiterate, and build an even stronger idea in the process!
  1. Look for the lesson instead of the setback

    In the past, I viewed failure as a problem to be avoided at all costs. Now, when I fail, I look for the lesson. Instead of beating myself up, I like to think that I’ve learned one more way that doesn’t produce the results I want (sort of like a “what-not-to-do!”)⁣. It brings to mind this Thomas Edison quote, 

    “I have not failed 10,000 times. I have not failed once. I have succeeded in proving that those 10,000 ways will not work. When I have eliminated the ways that will not work, I will find the way that will work.”

    Instead of seeing failure as the end of the path, I see it as a stepping stone to my next big success.⁣
  1. Practice, practice, practice.

    At the end of the day failing fast and forward is a skill and skills can be learned! Just like you had to practice to become an expert designer, artist, or writer, you have to practice HOW you fail. You probably won’t feel comfortable with failure right away, but take time to notice the failure, sit with the feeling, explore different options, and persevere through adversity! 

    One of my favorite ways to practice failing was inspired by Sara Blakely (the founder of Spanx). In an interview she explains how her father used to ask her and her siblings one question every night at the dinner table. Instead of asking what they had succeeded at, he would ask, “what did you fail at today?” She claims this exercise inspired her entrepreneurial spirit and reframed failure for her. My husband and I loved the practice so much, we’ve incorporated it into our own nightly ritual with our 2 kids! We’ve found it to be a powerful way to encourage them (and ourselves) to keep trying, even if they don’t succeed at something right away!

COO Tip: Journaling is one of my favorite tools both in my personal life and business! If writing is helpful to you, you may even reflect on your failures as a journaling prompt! Consider the facts (what happened) as a way to stop blaming yourself, making up false stories, or blowing things out of proportion. Then, journal about how the failure FEELS in your mind and body (Do you feel overwhelmed? Tense?). Lastly, think about your next steps forward: “What can I learn from this experience?”

Benefits of Failing Fast and Forward

Learning to fail fast and forward actually has some seriously tangible perks for your creative business! If you need some extra incentive to start embracing the power of failure, here are 4 major benefits you won’t want to miss out on!

  1. Save time and money. By failing fast and forward, you can work efficiently by investing less time or energy into an idea that may not work. When things aren’t panning out the way you’d hoped (aka the idea “fails”) It’s all about the ability to make a decision quickly so that you can pivot as needed! 
  1. Learn to trust yourself. Failing fast and forward is definitely more of a learned art than a proven science. Figuring out when to shift gears may not always be obvious. It can be hard to tell if you’re throwing in the towel too soon or hanging onto wishful thinking for too long!  But, the more you allow yourself to fail and try again, the better you’ll be able to trust your instincts and make informed, experienced decisions for you and your business. With each failure, you gain valuable insights that can often help you make better decisions in the future.
  1. Take healthy risks! When you play it safe, you limit the possibilities for your business. When you regularly take leaps, experiment, and allow yourself to be  curious, innovation and creativity can thrive! Starting a business is a risk in and of itself. And the most successful businesses are the ones that are willing to “color outside the lines,” do things differently, and push the boundaries of the status quo. When you put yourself out there, you can often come up with new ideas that can set your business apart from others in your industry or niche. Big things happen when you allow yourself to take chances!
  1. Build your resilience. Entrepreneurship is a long game. It requires steadfast focus, patience, and commitment. If failure gets you down and keeps you down, you are much more likely to give up on your business dreams altogether! Instead of hitting a wall and realizing your initial plans didn’t work out, if you can shift, adapt, and pivot, you’re much more likely to course correct and find a business plan that actually works for you, your audience, and your goals! Cultivating a growth mindset (vs. a fixed mindset) will serve you well throughout your entrepreneurial journey.

So not only can failing fast and forward save time and money, but you’ll also learn to lean into your intuition, take strategic chances, and build your growth mindset. Furthermore, as a creative, failing fast and forward actually fuels creativity! It can allow you to see things from new perspectives and make connections you may have otherwise missed!

Don’t be afraid to try, fail, and try again – it’s all part of the process!

The Difference Between Failing & Quitting

In truth, I believe there is no such thing as failure in business as long as you don’t give up!

Because you can only TRULY fail if you quit.

I don’t mean this in a toxic positivity way, but I genuinely believe that nothing is ever really a failure if you learn from it and build further from that knowledge.

If you keep going and keep trying, any failure (no matter how big or small) is just a pit stop, not a hard stop.⁣

So, keep going. 

Failure may not feel fun at the moment, but it’s not the end of the road.

I’ll leave you with this quote,

“Don’t be afraid to start over. This time you’re not starting from scratch, you’re starting from experience.” – Unknown

Need support?

Early on, failing fast and forward may not come naturally. 

That’s where I step in. 

Have a pesky problem, a tough decision, or a serious case of analysis paralysis in your creative business? I can help! 

I offer 90-minute Clarity Calls to help you bust through your toughest challenges quickly, efficiently, and as pain-free as possible! Click here to schedule your call today!


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