Your Worst Case Scenario: Four Ways To Evaluate and Succeed

Your Worst Case Scenario: Four ways to evaluate and succeed when making decisions for your small creative business.

I was browsing one of the Facebook business groups that I am in the other day and noticed a post from a woman who was seeking advice on whether or not she should proceed with a new offering for her customers. She was “scared” to do it, in spite of it being something that she would love to do. 

It struck me immediately how strange that sounded. To be scared of trying something new. Scared of what? But I’ve been there, too. Usually these fears fall into a few categories:

  • Failure: Turning away customers, being ignored, not being able to deliver a solid product
  • Struggle: Not making enough money to support one’s lifestyle
  • Burnout: Not being able to maintain the work, not having free time
  • Disappointment: Letting down one’s family, fear of judgment from others

All of these scenarios are absolutely possible. But in the whole scheme of things, none of these are impossible to handle. We create these mildly uncomfortable worst case scenarios to talk ourselves out of taking risks, both in our businesses AND lives. We’d rather dream about the possibilities than actually pursue them and prove that they are possible (or not possible).

So what if you fail? You’ll feel bad for at least a little bit. Then you’ll get up and dust yourself off to either move on or fix what didn’t work. Because you will figure it out!

What is the worst case scenario? What if you let your imagination run wild, and then used logic to navigate back to reality? Here are four ways to wrap your brain around your worst case scenario and decide if it’s actually  that bad:

1. Write down every possible reason you can think of that your idea might not work out. Then list all the ways to recover from those possible outcomes. Use this worksheet to do it.

Writing things down always helps me cut through the crap. For example, 

Worst Case Scenario: If I launch this new product, I’ll be investing money into something that I have no idea if people will want. If I lose money on this I will disappoint my family and prove that I should get a day job.

Solution: If no one buys this, I will either change it or eliminate it from my offerings. The money will replenish because I will eventually find something that works. Trial and error are part of the process. My family will be proud of me for going after my goals.

Get very specific and write every thought that comes to mind, even those that kinda make you cringe a little. 

2. Develop a habit of constantly challenging your worst case scenario.

Our neighbor’s three-year-old son used to ask a bazillion questions every time we walked by their house. At first it was really cute. But eventually we started scurrying by without making eye contact because we just didn’t have the energy to explain our every move to a toddler.

Be the toddler to your fears. 

Are you sure this worst case scenario is likely? Has this happened to you before? If it has, what can you do to recover or change something about what you are doing to make the outcome bend more in your favor. And what if you are exactly right and the worst case scenario is definitely going to happen? Is it a deal breaker? Why?

3. Embrace the discomfort that comes with change.


Most of our fear-based decisions are based on information from our past (or a lack of information) and anticipation of the future. From past experiences, we know what the outcome will be for those experiences. Sometimes we will continue to do something that we know doesn’t feel right just because we know the outcome and can predict it. For something you’ve never done, you can spiral into doubt because you don’t know the outcome at all, good or bad.

Plus, change is hard. It can be really exciting once you get to the other side. Inevitably, though, there will be that adjustment period where things can be uncomfortable. That period can last for minutes, or for months, or much longer. You have to embrace wiggling around in discomfort while you figure out what you are doing. If you are always protecting yourself from any ounce of discomfort…well, then you are probably not moving forward. 

4. Practice curiosity instead of suspicion. 

tweet this!

Instead of assuming that it’s gonna be hard and disappointing to do things differently from the norm, imagine what it would be like if something really amazing resulted from it. What if it leads you to some other fantastic thing that you never would have discovered had you not given it your best shot? 

My husband and I are very different in the ways we approach risk. This difference often surfaces when we have discussions about our lives decades from now. My husband makes references to retirement, which is a weird idea to me. Retirement? Why would I retire if I’m always doing what I want? 

And I still don’t know for sure without a doubt what I want to be when I grow up. I find that to be really freaking exciting. There is no point where I plan to just stop, put my feet up, and have everything figured out.

The journey is the goal. Let the possibilities romance you.

This post was originally published on September 15, 2015 on

About the Author

Casey Sibley is the owner + artist behind Casey D. Sibley Art + Design, a studio specializing in vibrant pattern design for textiles and a lifestyle brand of accessories and home goods in a happy, modern style. She is passionate about living a happy life and encourages creative business owners to take charge and lead a life by their own design. You can follower her on everything social at @caseydsibley and visit her webiste at and