Be The Boss & The Employee In Your Creative Business

Before we jump in: This article was originally shared with my email community in November last year. I'm sharing it with you on the blog today in the hopes it may be of some encouragement and insight to you in your creative journey right now, and also give you a little sneak peak of what you can expect from Weekly Letters too. If you'd like to receive letters like this one straight to your inbox every other Sunday, you can sign up below. You'll also have access to over 100 past Weekly Letters too! 


There’s something I’ve been encouraging my clients to explore recently in their business and creative journey. I ask them:

"What would it look like to be the boss and the employee in your creative business?"

Because here’s the thing: I see my clients struggling over and over again with not feeling productive, feeling unsure of what to prioritise in their business, and feeling frustrated because they aren’t holding themselves accountable to the goals they set for themselves along the way.

With all the joys that come with being your own boss (being able to work in yoga pants from the sofa, being able to wake up whenever you want, never needing permission to take time off, the lack of limit on your earning potential) there are some struggles that come with this journey too.

Having no one to force us to work each workday - we have to be our own motivation and daily kick-up-the-ass

Having no one to tell us when we’re doing a good or a bad job apart from ourselves

The loneliness and isolation that comes from working by yourself at home all day

The financial stress of being in charge of every single penny you earn

The underlying constant fear that we’re not working hard enough, or achieving enough, in our business

Here’s what I’ve been wondering recently: most of us choose the path of self-employment because we never want to have a boss ever again, but then we may struggle to embrace being both the boss and the employee from now on. 

We have two roles in our business:

The CEO: We have to be the visionary, to spend a whole lot of time with our bigger picture, our business model, our business plan, and be thinking about the next 3-5 years and as much as we think about the next 3-5 months. We have to be able to make smart, brave, bold, and sometimes even risky decisions to keep the business moving forward - and we have to do all of this without letting our ego or fear get in the way. 

The employee down in the trenches making things happen each day: We have to show up, each day, and get stuff done. From emails, to admin, to client work, to content creation, networking, and everything else in between. It’s on us to show up and tick off all of those to-do’s and do the sometimes tedious daily tasks that help make the bigger picture for our business a reality.

And sometimes we're just naturally more comfortable in one role more than an other.

Maybe you love hashing out your business plan, setting big picture goals, and hanging out with your business vision and outlining how you can make that happen, but you struggle to stay focused when you’re down in the trenches each day getting stuff done. 

Maybe you’re more comfortable with the day-to-day in your business and showing up and bringing your creativity to life but you struggle to really have a bigger vision and plan for your business along the way.

My challenge for you today is this: explore what it would look like for you to be both the boss and the employee in your creative business.

As CEO, ask yourself:

  • Do I have a clear business plan and model guiding me along the way? If not, how can I prioritise some time to work on that?
  • What are the core areas of focus and priorities for the next 6-18 months in my business? What do I need to put in place to make the day-to-day running of my business more productive and focused?
  • What core goals do I want to work towards in my business in this season and how am I practically going to make them happen?

Hopefully what you can start to discover here is your bigger picture vision and plan for your business. And then as your own employee, it’s your job to manage the day-to-day responsibilities of your business, while ultimately following the guidance and vision of your CEO (which just happens to be yourself) too. 

By embracing both roles, not only are you making sure that you’re focused each workday, but you’re also making sure that your business is focused and connected to its bigger picture, instead of just getting lost in the day-to-day as you go. 

And the secret to making this work? Carve out time for both. Have a “CEO Day” at least once a month, if not every two weeks or so, so you can be constantly checking in with the business and making purposeful and intentional plans of action so you know each month, week, and day what needs to be done. Be comfortable with embracing both roles, and sooner or later it will hopefully become second nature to you. But don’t put pressure on yourself in your “CEO” role to have all of the answers - we never need 100% clarity to make things happen. Don’t let the unknowns and the things still left to discover hold you back from moving forward - because it’s by moving forward that we discover what’s next. 

Here's to being the boss and the employee in our creative business...

As always, I'm rooting for you!


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