I heard this phrase once and it was so funny and spot on, I couldn’t UNHEAR it.

Quit “shoulding” all over yourself.

It’s cheeky but true!

The world of entrepreneurship will often leave you overwhelmed by options, “directions,” and advice! 

Not only are you responsible for keeping up with the logistics and tasks of running your own creative business, but you also can’t help but feel like there are a million and ten other things you should or could be doing… because… well, everyone else seems to be. 

It’s a classic case of keeping up with the Joneses. 

But in lieu of white picket fences and shiny new cars, entrepreneurs in the business space tend to compare profit margins and marketing hacks.

Truth is, reality is not always what it seems. 

And just because it seems like everybody and their brother’s jumping on the next social media fad or sales trend doesn’t mean you have to. 

Heck, it might not even make SENSE for you and your business in the first place!

But it’s easy to get sucked into the woulda, coulda, shouldas and start to feel like what you’re doing in your business isn’t quite enough.

However, when we let those “shoulds” drive the bus and dictate our decisions, we often end up building unaligned businesses that leave us feeling,

• depleted 
• unfulfilled
• and downright frustrated

This blog is all about sifting through the noise to understand what motivates us to take on tasks, why shoulds and coulds are dangerous when left unchecked, and how guilt and obligation influence our personal and professional decisions more often than most of us would like to admit.

You’ll walk away with actionable guidance to help you question those shoulds so you can be sure every decision you make is truly in your best interest and helping you meet your creative business goals. 

Why “Should” Is Often A Red Flag

When a “should”  is leaving you feeling guilty for not doing something or obligated to do something, it’s probably a red flag that it’s not the right move for YOU. 

Shoulds can also present themselves as “supposed to’s” which lead us to think that there is one way to do things in our businesses. 

Every time you hear yourself say or think these phrases, it’s like a little red flag reminding you to slow down and question this notion. 

When left unchecked, “shoulds” have the potential to…

• drain you of your creativity
• disempower you
• fill you with dread
• and even spike your anxiety

Most times the word “should” is a clear indicator that you’re following someone else’s script, blueprint, or plan and NOT your own. 

Without even realizing it, you’re given blanket advice about how to run your creative business 24/7/365. 

It’s present in social media posts, online courses, coaching programs, masterminds…heck, even blogs!

Much of these “shoulds” come from things like hustle culture, social expectations, (outdated and false) gender norms, prevalent myths, imposter syndrome, and stereotypes like the “starving artist.”

And while some advice may indeed be helpful and relevant to your business, only YOU can decide what truly resonates with your goals and values as a CEO.

Because there’s definitely NO one-size-fits-all way to be creative or run a creative business. 

What works for you is always the best way, no matter what. NOT the cookie-cutter, business-in-a-box approach.

The Dangers of “Could” In Your Creative Business

Aside from all the constant “shoulds” you’re bombarded with as a creative business owner, you may also experience a mountain of coulds that figuratively pile up in the back of your mind. 

It reminds me of the common expression, 

“Just because you COULD doesn’t mean you SHOULD.”

Coulds become shoulds, and shoulds only weigh you down!

Sure, you could jam-pack every spare minute of time on your calendar with additional tasks and projects. 

But productivity just for productivity’s sake isn’t smart business and it’s definitely not sustainable!

If you’re not careful, the countless number of “coulds” can fill up your calendar and to do list– FAST! 

Often the coulds are fueled by feeling like you need to prove yourself, optimize your time, or be as productive as humanly possible to be worthy of the life and business you’re striving for. 

The funny thing is, this approach — while first and foremost very unhealthy — also tends to backfire! 

When you’re focused on doing anything and everything you possibly COULD without considering why you’re taking those actions, you end up wasting your time instead of optimizing it! 

You see—

While I’m a big fan of time management hacks, I think we should be efficient with our time so we can reclaim it and enjoy life OUTSIDE of our work. 

Productivity isn’t the end goal in my book. 

Time is a finite resource and once it’s gone, it’s gone. And while there are always a million things you COULD be spending your time on creating, honing, or building in your business you have to be discerning with your time or you’ll never have enough of it!

So if you’re tempted to add more to your workload, be sure to consider if you’re really gaining anything from this task, or if it’s simply a distraction that’s actually moving you further away from your goals.

I’ve found the best way to avoid this time trap is to get clear on your business vision, mission, and values so that you can set firm boundaries and understand what success in your work looks like. This will allow you to identify the actions that will truly move the needle for your creativity or for your business. 

The Role of Guilt in Entrepreneurship

It’s important that we unpack the underlying feelings of guilt that are often associated with the phrases, “I should,” “I could,” or “I’m supposed to.”

Guilt is a powerful teacher in life and in business. 

We simply need to listen and pay attention when it bubbles up. 

When used in a healthy way, guilt can help us rise to the occasion, take responsibility, and do the right thing in line with our personal morals.

However, some guilt is unwarranted and self-imposed. In fact, we often use guilt as a weapon against ourselves (hello, self-sabotage). 

When guilt comes with feelings of SHAME it is never serving you well and is often a signal that it’s time for you to reassess before you take further action in your business. 

After all, while it certainly won’t be sunshine and rainbows all the time, your creative business is meant to be fun and enjoyable not ridden with shame and guilt! 

When exploring “shoulds” and “coulds” in your business, always take time to do a pulse check and see if guilt is at the core of your desire to take that action.

If so, don’t be afraid to pivot and move in a direction that feels more authentic to you- even if that means blazing your own trail! 

How To Discern Your “Shoulds” From Your “Should Nots”

My clients are probably so tired of hearing me say this:

“Question all of your shoulds!” 

But I’m not a broken record just for the fun of it! 

Being critical of the things you think you’re supposed to do is crucial if you want to build the business of YOUR DREAMS– one that actually works for you!

Some “shoulds,” “coulds,” and “supposed to’s” may indeed be beneficial to you and your business. But how can you determine which ones to act on and which to let go of? 

The key is taking the time to unpack what is truly motivating your decision. 

I’ve collected these super tangible, actionable ways to question your “shoulds.”

1. Ask yourself where the “should” is coming from. 

Often this comes down to internal vs. external motivation (hint hint: guilt often plays a BIG role in this). Internal “shoulds” are often the most reliable. These may be positive commitments you’ve made to yourself or others that represent your values and desires. 

External “shoulds” can be a bit trickier! They often come from processes you’ve learned, stories you’ve inherited from your culture, or societal expectations. These motivators often stem from some kind of guilt or obligation– you may not even be aware of how deeply embedded these are in your psyche!

2. Ask yourself if the “should” would make a real difference in your business (and if so, how much). 

Take time to consider the consequences of this action— or inaction for that matter. Since this is a “should” you most likely haven’t taken action on it just yet, so maybe there’s an underlying reason why (whether you realize it or not). 

Pay attention to your resistance while also being honest with yourself about any consequences of your inaction. 

3. Prioritize your “shoulds.”

You may decide that some of those shoulds are legitimate, meaning they’re in alignment with your goals and values and feel like a good fit for your business. If this is the case, once you identify what you want to take action on, prioritize them accordingly. 

Some actions can probably wait until you have time to get around to them and will receive lower priority while others will feel high-priority and require your attention ASAP (we all have those super important to-do’s that we put off longer than we mean to. No shame, but let’s get it done!) It feels so much better to have those high-priority tasks off your plate. Creating a prioritization plan can help you make it happen without getting derailed by less essential tasks.

Understand what’s motivating the “should”, assess what impact the action will have on your business, and get your priorities straight to ensure that the things you feel you should be doing in your creative business are actually worth doing and have the positive influence you’re looking for!

Next Steps

I hope you feel encouraged to finally drop the “shoulds” in your creative business once and for all so you can shed the guilt and obligation and take actions that feel aligned and supportive instead! 

Keep in mind, as the owner of your business you are the boss so you get to call the shots! 

But if you still find yourself struggling to sift through the “shoulds” and “coulds” in your business, please know…

You’re not alone!

Decision paralysis is more common in the creative business world than you may think.

If you’re looking to gain clarity as an entrepreneur and develop the strategies to back your creative vision, my business course for creatives is for you.

Click here to learn more and be the first to know when the course is open for enrollment!