Are People Please Tendencies Holding You Back?

My husband cringes a little every time he watches me bake. Although he’s no chef himself, whenever I toss garlic into the cast iron pan with a regular spoon rather than the Pampered Chef adjustable measuring spoon I insisted we buy or sprinkle baking powder into the cookies, he becomes visibly uncomfortable at my lack of calculation. But really, what kind of psychopath measures vanilla instead of sloshing it into the bowl?! I digress.

I’m an eyeball-it kind of person in the kitchen — and it took me years to become unapologetic about that approach.

While I love to cook now, I didn’t grow up cooking. Through no fault of my parents, I grew up in a time where TV dinners were the it thing. They were the food my parents thought I was supposed to eat, so that’s what we did. A quick zap of soggy chicken nuggets and syrupy cinnamon apples. Dinner was served.  

When moving to Denmark, the only thing my new Danish family asked of me was to cook one meal a week. Can you believe that out of a huge international move, that request to cook was perhaps the thing I was most nervous about? 

The nerves quickly settled when I shared my ignorance in the kitchen. Instead, the family I was living with would sit in the kitchen sipping wine while they showed me how to cook from scratch. First, I learned how to peel potatoes with a knife (if you know, you know). Then, how to chop an onion. Then, how to scrape the brown bits off the bottom of a pan and make gravy. 

It was cozy. It was fun. Perhaps that’s why I like it so much now. 

I’ve unearthed a side of me that had been buried by all the “supposed tos.” 

Now, I cook my way — careless but measured, calculated but consistently ditching the measuring spoon like the unapologetic rule-breaker I am. 

While it’s all fun and games, and I can ignore those cringey stares from my husband today, it wasn’t always that way. 

As I was cooking up a paleo chicken pad thai last night, I thought about how far I’ve come in the kitchen and how long it took to become that Swedish Danish chef. The parallels between that journey and business-building are undeniable.

Now…not as much.  

What would happen if you could lean into a side of you that’s been buried for far too long by the shoulds and supposed tos of the business world and do things your way, no matter how someone else peered on?

Over the summer, during my period of reinventing myself, I realized that I had buried my light among all the business advice I’d received over the years. I was showing up in a way that felt aligned with how others who didn’t travel often or weren’t the full-time caregivers of their family were building their businesses.

If you’re here, you’re like me. You want to live an unconventional life of travel now. You want to have a calculated but careless adventure. You want a life and business that feels good rather than fits into a mold of how everyone else approaches their world.

Reaching that end can feel harder than meets the eye. So much more goes into figuring out what your way looks like in business while simultaneously ignoring the barrage of advice from online gurus, self-proclaimed experts, and side-eyeing onlookers. 

If you’re feeling this heaviness and are ready to take the basket off your business light so you can shine into the world, here is a quick three-step exercise on how to reconnect with what your way looks like.

I did this recently while watching my kid’s jiujitsu class, then promptly went outside to share pictures of my results with a few biz buddies, so while it’s easy and fast, it’s also enlightening and will fire you up.

Grab a pen and your favorite notebook, then sit down and journal for a few minutes.

I like to think of businesses as campfires we invite others to join us around. With that visual in mind:

In less metaphorical terms, what’s your why? Although that phrase is grossly overused, it’s important to think through. Without a foundation for knowing why you’re here getting uncomfortable each day with the unknown, uncertainty, and sometimes lack of understanding from others, it’s hard to uncover your unique approach to business — the one that’ll feel crazy good to you when you nail it and bring so much clarity. Even if this exercise feels tired, humor yourself and me on it again. Write down your why. 

Shameless plug: If you need help reconnecting with your vision for your business, my co-author, Kristin Gudenkauf’s part in our bestselling book Discovering Something Greater can help too.

When I went through this exercise, I looked through the lens of my sister company, Cruisin’ + Campfires. Here’s what I wrote down:

Consumers are emotional creatures. We don’t make decisions flippantly. We think through them. We feel our way into them. 

As evidence, stroke victims who have had the emotional response portion of their brain impacted after a medical event have a harder time making future decisions. That’s because we must know how we’ll feel on the other side of the decision to decide what we need. 

This one step is why so many people revert to the comfort of doing what the online experts and gurus tell them to. They trust that those people, who have walked the walk before, already know what the outcome will be and will know how they will feel. 

That blind trust is a dangerous thing and has caused far too many people to invest heavily in programs that don’t offer results. The course might teach what’s worked well for someone else, but in practice, it doesn’t feel great for you. It’s not doing business your way. It’s doing business by following someone else’s recipe.

For this step, write down how you want your why to feel for you and your customers in action.

Here’s what I jotted down for this step when conducting this exercise for Cruisin’ + Campfires:

Ready for your light to shine? Here’s where we connect the dots. 

For each bullet-pointed feeling you and your customers desire, write down what that feeling looks like in the real world. In doing so, you move away from nebulous concepts to specific ideas that you can implement immediately in your business. 

Here’s how mine fleshed out:

While I’m not investing thousands of dollars to run out and create all of these products and designs immediately (product-market fit needs to happen first), I have them all on my radar. I see where I want my company to go. I am clear, confident, and consciously making choices that will honor my vision rather than the “supposed tos.”

I recently conducted this exercise for Roadpreneur and am steadily shifting how I show up for you. As you might’ve guessed, it’s not the conventional online business style, and I like it that way. 

One shift I’m making is adding a new Feature Friday column. 

This column will feature stories from fellow Roadpreneurs who are doing really cool things with their business-building journey, breaking norms, showing up as themselves, and building a life they love in the process. Through reading these stories, we can feel inspired to continue on our journey, be encouraged by others’ successes, and learn from others’ failures (we’ve all got ‘em). 

Those stories will all be free for you to read each Friday. 

If you want to continue receiving the how-to guidance, journal prompts, and more tactical information as you see here — plus more that I’ll soon be adding under the hood, like discounts on the MANY courses I’m releasing in 2024, private coaching sessions, and priority to be featured in this new column — you’ll need to upgrade to become a paid subscriber. For the cost of a cup of coffee each month, you’ll get business advice designed for unconventional entrepreneurs. 

Subscribe now. The price will go up in January when the new column is released, but if you join today, you’ll lock in this price of only $5/month (or less if you pay annually). 

Here’s to you: committing to a life of adventure, doing things your way, and challenging everything you’ve been told you’re “supposed to” do.