How To Thrive Through The Uncertainty Of Your Creative Business

In January of 2015, my Better Lettering Course (a $20 basic course on hand-lettering) made me $5,100/month of (virtually) passive income.

Basically one blog post on my site was getting an unbelievable amount of traffic from Pinterest and it was converting to sales of the course. My gifts/talents/products were aligned with a need in the market, plus I had an effective marketing machine that was pumping life into my business. Times were good, and I actually thought to myself, I think I’m getting the hang of this independent business thing.

Fast forward to yesterday when I pulled the financials from September (I do this every month separately from my bookkeeper to keep myself actively evaluating my business revenue and deciding which projects to focus on and which to let go of.)

Do you know how much income that same lettering course pulled in for September 2016? $460.

$5,100/month to $460/month.

Quite a difference from the basically full-time salary it was creating for me throughout last year.

Now, thankfully I’ve been smart enough to diversify my revenue over the past two years so my business health doesn’t hinge on the sustained success of one product. 

But I wanted to share these numbers with you guys to illustrate a very important lesson in running a creative business, one that I don’t see enough people talking about online: The market is ALWAYS changing.

As artists and creatives, we often want to operate in an ideal world where we can simply create what we want to create, build an audience of devoted patrons, and watch the money follow.

(Let me be clear, I still VERY much advocate for making this kind of idealism the primary approach. We’ll never even come close to creating an ideal life/career for ourselves if we don’t start by aiming high and believing in what’s possible.)

BUT, I also believe we have to temper that idealism with the pragmatism of what actually works in business and what will actually bring us money.

I believe that delicate balance is the cost of entry for the immense privilege of earning a living solely from your passion. The truth is that we can’t go on creating our heart’s work if we don’t have money to sustain us. So while money will never be a primary driver for me, the financials have to be stable in order to give me the space and oxygen I need to create.

Which is exactly why it can be so terrifying when a once stable source of business revenue stops being stable.

Turns out, there’s actually a biological basis for this fear. See, humans CRAVE certainty. When faced with uncertainty, our brain’s go into a state of defense. Here’s a particularly interesting passage on the subject from Psychology Today:

“A sense of uncertainty about the future generates a strong threat or 'alert' response in your limbic system. Your brain detects something is wrong, and your ability to focus on other issues diminishes. Your brain doesn't like uncertainty - it's like a type of pain, something to be avoided. Certainty on the other hand feels rewarding, and we tend to steer toward it, even when it might be better for us to remain uncertain.” 
- David Rock, Psychology Today

Did you catch that? To our brains, uncertainty basically equals pain.

To make that uncertainty even more complicated, not only is the market a moving target, but WE are a moving target ourselves. What we want today may not be what we want tomorrow.

What I value right now in my life above all else -- flexibility, freedom, experimentation -- may not be what I value in five years when, let’s say, I’m starting a family.

So that’s the core challenge of running a creative biz: the market is always changing, and YOU are always changing. Either way, what worked yesterday won't work today, and that leaves us in a perpetual state of uncertainty.

The challenge of running a creative biz: the market is always changing & YOU are always changing.


To my creative business owners out there (or aspiring creative business owners), does this hit home with you? Can you relate to that sense of anxiety that comes when something that was once solid ground for you becomes dust beneath your feet?

Maybe it’s a revenue stream that takes a downturn. Maybe it’s social media growth that suddenly stalls. Maybe it’s a launch plan that worked a year ago but is no longer connecting.

Or… maybe the uncertainty is stemming more from the moving target within. Maybe you no longer feel connected to a creative project you started a year ago. Maybe your values have changed and now you don’t feel aligned with what you’re producing in your business.

In either case, the question remains:

How do you thrive when the game changes on you?

Well, I certainly don’t have all the answers, but after contemplating this quite a bit, here’s the advice I’ve been giving myself.

Tips for Thriving Through the Uncertainty of Business:

1. Learn to love the puzzle.

The unfortunate truth is that the uncertainty of “the puzzle” will never end. This mixed up rubik’s cube where all the variables are constantly changing -- you, the market, social media, technology -- will never stop changing. Though we’re hard-wired to seek out certainty, we have to come to terms with the fact that we live in an uncertain world.

Part of being an effective business owner is learning to love and appreciate that constant flux. To find joy in the variety of it all and to let the puzzle feed your curiosity. Can it be exhausting and frustrating sometimes? Sure. But, flip the script for a moment and it can also be fun and interesting and incredibly rewarding when you see yourself solving level after level of the complicated puzzle.

2. Don’t let your uncertainty turn into self-doubt.

When we’re facing the unknown, it’s natural to feel fear. But unfortunately, what so many of us creatives do in response to that fear is we make it say something about US. When things go changing on us, it’s our immediate reaction to suddenly question all that we are or all that we’ve ever done, as if any wins we’ve had to that point weren’t a reflection of our capability but instead a fluke.

I could have let the change in my lettering course revenue affect my confidence in my own work. “The course must not be that good. People don’t want to learn from me anymore.” Ummm…. Over 3,000 students seem to disagree. Instead of letting the uncertainty of the future turn into self-doubt, I was able to look at all the revenue that product has brought me over the years and let it FEED my confidence, not diminish it.

3. Make your internal metrics as clearly defined as your external metrics.

This is HUGE one. It’s so much easier to define and measure our success with external metrics. Followers, dollars, subscribers… these are all NUMBERS and numbers are well within the comfy, non-painful certainty camp. That’s why we cling to them. They feel like a concrete, REAL reflection of the health of our business.

But what happens when you’re ONLY measuring your business health or success with metrics that reflect external factors? If you’re defining your success only based on how the market responds to you, you’re placing all the power into the hands of something you can’t control.

You can’t control how people respond to your art or your business offerings or your products. You can only create, experiment, observe, learn, and grow. If you’re only measuring your success by the level of market validation, then you put yourself at risk to be disappointed every time you try something that doesn’t work. (Which, as I’ve pointed out, is almost 100% certain to happen in the life of your business given how ever-changing the market is.)

Instead, we have to soften those expectations and external metrics with inner ones. So, ask yourself: how can you measure whether your business is meeting your internal desires and values? Can you count the amount of mornings you’re able to take 15 minutes for a gratitude practice? Can you do it in the number of hours you’re working, or the number of times you create something that feels scary?

The external metrics may feel real and satisfying to our need for certainty, but the internal metrics -- the ones that tell you you’re fulfilling the deep, true desires of your most vibrant life -- are the ones that bring important context to those numbers. I’m perfectly happy to see a drop in my revenue if it means I’m working less hours, taking more breaks, and stretching myself creatively.

This week, your challenge is to write down your own internal metric system.

Next time you find yourself in that spiral of uncertainty when something in your business stops working the way you thought it would, I want you to first come back to that metric system and remind yourself to also measure your internal alignment. Find peace in the fact that at a core level, you’re still making decisions aligned with your true self.

THEN, remind yourself that business is merely one complex puzzle after the next. Keep changing one variable at a time until you land on something that IS working again. (And prepare yourself for the moment when that too changes yet again.)

We live in a time when it’s easier than ever to create a business around who you really are and the things you love. BUT, that’s doesn’t mean it’s EASY. It will never be easy. And I’m starting to think that could be part of the fun of it. 😄

I hope this week’s letter was helpful. I haven’t dedicated an entire letter to a business topic in a while! I love sharing this ever-evolving journey with you guys, so THANK YOU for reading week after week.