Can I Make A Living Doing What I Love?

The following is an excerpt from a newsletter published April 4th, 2024


In cursive letters "tout est possible" is spray painted on a wooden fence. There are overgrown bushes the background.

I've had versions of the do-what-you-love, follow-your-passion conversation with myself and clients for years.

While I can't answer this question for you, I can have a conversation about it.

Here's what comes to mind for me. 

As always, reply and let me know what comes to mind for you.

 

— Is this the most interesting (or useful!) question? 

I've watched many people, myself included, back themselves into a corner and go through years of sludge and stagnation trying to “find their passion/purpose”. (Funny how we put so much emphasis on preemptively answering questions that can only be answered by living them…)

It's OK for a question to have no clear answer, but if the question you're asking immediately puts you in sludge, shame, or stagnation… try asking a different one.

How about….

  • Can I make money doing meaningful work? Work where I’m respected, encouraged to explore my potential, and well compensated?

  • Can I set my life up to be able to pursue my creative passions or vocation, regardless if I’m paid for it or not?

  • Can I make a living within the limits of my mental/physical health, or caregiving responsibilities?

The questions we ask shape the answers we get.  

If we want better/different answers, we need to ask better/different questions.  

 

— Creative fulfillment doesn't have to come from paid work 

If creative expression is a high value of yours and you're lucky enough to choose what you do with most of your time… let's first and foremost make sure your life is set up to fulfill that need.

What structures, practices, or rhythms best honour your need for creative expression? A just-for-you hobby/practice? A community activity? A business, or a portion of your work within that business?

If there's anything you can't not do, it's worth setting your life up so you can always do that thing even if you're not getting paid for it.

(!!)

 

— Consider mutuality: business is not a self-indulgent act

I do not believe that business is a self-indulgent endeavour. A business is, by definition, a relationship between you and others. Hopefully a consenting, non-exploitative relationship, one that requires we work within the overlap of “what I need/love” and “what others need/value”. 

It's common to swing out to either side and think too much about ourselves or too much about others. In reality, your business is the generative, ever-shifting third space between the two. 

This is why business is such a beautiful expression of creation and, yes, why it's so challenging. It's not static, it's not just about you, it requires us to be in the messy muck of life. 

 

— What if my art is my business?

This is a tough one, and I'd genuinely like to hear what you think.

What about the artists (musicians, painters, writers, weavers, etc.) who seem to make a living doing whatever they want? Whose sole driving force seems to be creative/self-expression?

Are they being self-indulgent, but lucky enough to get paid for it? Or by going far enough into themselves are they hitting on a resonate, universal truth that invites others back in?

I think that second bit is true, and, I think that as soon as we're in business we're also having to consider needs beyond our own. If the artist isn't doing the broader audience consideration and bridge-building (marketing, money, & sales), someone else in the business is (a manager, partner, etc.). 

You also never know how much support an artist is getting (financial and otherwise) that allows them the material/emotional safety to do what they do. 

I think the most important part here is to explore your own expectations and assumptions. What are you assuming is true? What else might be true? 

 

— Explore underlying needs

Sometimes the strong-yet-vague desire to DO WHAT WE LOVE!! is actually a cry out from a pile of unmet needs. What parts of you, your values, or needs are currently not getting expressed or are actively getting overridden?

If you want to stay in your work long-term, there needs to be room for you in your work.

It's worth exploring the specifics of what “doing what you love” would mean. What would you do with your days? Who would you be? How would you feel as a result? Is there any way you can give yourself some of that feeling now, within your current setup?

Tip 💡: In general, anytime you're experiencing loud emotions/desires/swings ("I'm burning down my business! I'm leaving this relationship!") listen for what needs aren't being met, or what expectations are going unsaid. Our bodies tend to shout at us when we don't listen to the whispers.

 

— How can you make your current work more meaningful, enjoyable, or sustainable?

Assuming we're not dealing with a get-out-now situation… it's worth asking what shifts you could make within your current work to allow for more of you.

It's a common growth pattern to table-flip what's not working ("I quit!"), pursue a shiny passion, and realize that the same growth edges that were holding us back in our last job show up here also (i.e. self doubt, communicating our needs/expectations to others…etc.).

Wherever you go and whatever you do… all your glorious humanity will follow :).

Remember ❤️: Pursuing work we love is about so much more than the work itself—it's about how we show up to the work, who we work with, how we treat ourselves and others, and how we meet each others needs. 

 

— Do you love your Tuesdays?

Perhaps a more productive guiding question is how can I make a living and love my Tuesdays?

Aka your most average, boring day. Not the shiny day where you won the award or signed the lease or booked the contract… but your run-of-the-mill weekday. What would it mean to make that good?

When shaping your work/business—and by extension your life—it's useful to zoom out and consider how you want your life to feel in general. 

 

— Finally, honour the tension.

If you are unable to make a living doing the work that is most meaningful to you—or that you know would have the most impact on the world—that is almost certainly not a failing on you but a symptom of a failing system.

Please, please make room for your idealism and your dreaming (and share these dreams with people who are safe enough to allow for their fullness!). Keep holding yourself and the world to a higher standard. But don't be so hard on yourself when you're inevitably pulled between the tension of how things are and your knowing of how things could be.

We live life here, in this messy middle. Between our dreams of the future and the stark reality of the present. 

(Parker J. Palmer calls this “standing in the tragic gap”.) 

  

Maybe someday, or for various seasons of life, you'll be able to make a living “doing what you love”.

How very blessed we are if that's true. In the meantime, as much as possible—don't let one stop you from the other (making art at the expense of making a living, or making a living at the expense of making your art). 

 

Rooting for you, always,

— Kate


P.S. Today's header photo says, “tout est possible” which translates to “everything is possible”. A bright spot from a walk on a tough day. 

P.P.S. SPRINGGG!! A playlist for spring.


Kate Smalley

Kate Smalley is a small business advisor, facilitator, and educator based in Toronto, Canada. She writes about growth and business development for principled, industry-shaping entrepreneurs.

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