The No BS Guide on How to Deal with Awkward Conversations with Friends & Family

Mariah Carey is thawing out and there’s a chill in the air, which means it’s officially time for ye olde Family Get Togethers.

With more family time, you’re likely to encounter a few awkward or unsupportive conversations about your creative work, your biz, or (gasp), even money. 

(If you’re a creative work-for-yourselfer, you will find that people are endlessly fascinated by how much money you make! Ask me how I know.)

And all of this? It can drastically chip away at your that millionaire mindset that you're cultivating, especially if you're an entrepreneur starting or building a business.

It can make you doubt yourself, cause anxiety, and even open doors to more confusion later on, long after the party's over.

I was in my mid 20s, fresh out of grad school, when I dropped the bomb on my family that I was no longer going to become a well paid, tenure track Science professor, and instead, was going to go rogue and dive face first into a creative career. I was going to be a professional creative, and was the first person in my family who ever dared turn down the usual 9-5 lifestyle.

I’m one of the lucky ones. While most of my family didn’t quite grasp what creative entrepreneurship was all about, most of them gave me the benefit of the doubt. But not everyone supported my dreams. And more still simply didn’t understand what a creative life or biz even looked like.

Some of your people might be your cheerleader squad. If so, celebrate them!

But if you find yourself up against some judgy, frustrating, or perilous convos about your biz endeavours or your creative work, here are a few tips to help you out.

TIP #1: Let it be okay.

If you’re a creative soul in biz, don’t assume that others will get it.

Repeat after me: It’s safe to be misunderstood.

Needing to be understood all the time is a total money block, and it can keep you from voicing who you really are, which will always affect how you show up in your business and sell your work.

Why? We creatives are an odd bunch. We’re card-carrying weirdos, who usually have an entirely dialogue (or two) going on in our heads, and are oftentimes the most sensitive of the group. That’s not a liability, it’s a superpower.

Tis the season to remind yourself that understanding or support aren’t mandatory in your world, but respect is.

A lot of people might not get what you do, or the hows or whys behind why you’re chose a more unconventional creative life of entrepreneurship.

But guess what? They don’t need to GET it. Your creative work matters, regardless of what anyone says or doesn’t say about it.

Gift yourself the freedom of a boundary - they don't need to get you, and you don't need to twist yourself up to help them understand.

TIP #2: Remember who you are.

If you find yourself up against some passive aggressiveness around your work or choices, remember Who The Hell You Are. Think Mufasa, booming down from the clouds.

Make a note on your phone, or create an alarm or reminder. Why exactly did you start your business? Why does it matter to you that you share your creative voice and message with the world?

This is what matters, and having the reminders front and centre when things get awkward can be helpful.

TIP #3: Watch your brain.

You can't control others, but you do have agency over how you react. Awkward money or biz conversations are the perfect fodder to do some digging for those juicy money stories we cover in CMA.

As you navigate any awkward or unsupportive comments, observe yourself and your desire to respond defensively.

If someone says something like "It must be nice to have so much free time for your hobby/biz...", check in on your urge to defend yourself. 

You don’t need to justify anything - and honestly, sometimes simply reminding yourself of that fact are all you need to smile, nod, and change the conversation to something that's easier to navigate.

Here's the key:

The more any someone's comments shake you, the more you need to tend the parts of yourself that need it - especially your self belief.

You’ll probably find that the earlier along you are in your biz, the more likely criticism, confusion, or judgment is going to sting. And that’s okay!

Tend yourself first. If someone’s getting under your skin with their lack of support, get curious:

What about their attitude is touching a nerve?

Do you subconsciously believe them on some level? Do you need to do a little digging to unearth some inner blocks that are asking to be seen? Let your holiday time be an experiment, and allow these people to be mirrors for you and see what reflections are asking to be seen.

The truth is, as painful as unsupportive family/friends can be, it usually won’t touch you if you’re on solid footing within yourself about your own dreams. You may feel the pain of being unsupported, but it won’t shake your foundations.

Give yourself the chance to observe your reactions, and use them for good to reaffirm the inner work you're doing!

TIP #4: The Keating Pit Stop

This is a classic, tried-and-true move that rarely fails!

If Uncle Frank gets all up in your biz and starts demanding to know how much money you make, or “how that little book/business/basketweaving course of yours is coming along”, and you just can't get the subject changed, it's time for the pit stop.

I first read about this technique from a former FBI agent, who used it when cornered with questions that might blow his cover. Thankfully our stakes are much lower!

It's so simple.

The next time you find yourself in a conversation that's tough on your money mindset, excuse yourself, pop into the restroom and wait it out for a few. That's it!

Chances are, by the time you return, Uncle Frank will have moved on to top up his cheese plate, and you can bookend that conversation with him. 

It's your business. You're allowed to set boundaries around what you tell people! 

TIP #5: The Wikipedia Test

What if, instead of not supporting you, your loved ones are offering unsolicited biz advice? 

I can still remember the time someone told me I should ditch the kids’ books I was writing and “start writing real books to make some real money”. Last I checked, my books and money are entirely real! 

This can be well meaning, but also awkward, and it can also swing to resentment or mindset wobbles if you let it.

Whenever someone gives me advice in biz - whether it’s a well meaning family member or a less-than-kind comment from an acquaintance, I do what I call the Wikipedia test.

Ask yourself:

Would I trust this person as a valued source about my biz? My income? My creativity? More than that: Would I pay them for their guidance?

If no, thank them for their thoughts & file that one under “Not for Me” in your head.

Some people just like to offer advice - and it’s okay if it doesn’t fit you. And you definitely don’t need to inform them of that fact, either!

If it doesn't pay, it doesn't stay. And that means if it doesn’t help your joy, creativity, mindset, or well being, you get to set it aside.

That includes well intentioned but unhelpful comments from your family or friends. They aren’t your clients, your mentor, or your community, so it's safe to accept that you don't need to agree or resonate with them.

TIP #6: Bring a (virtual) buddy.

If you know you’re in for a tough time this holiday season, why not prepare yourself with some backup?

When I was starting my creative biz, I started a DM chain with a fellow writer, specifically so I could have a life raft over the holiday season.

We would text each other as needed, and even if it was just a quick eyeroll emoji of support, it made all the difference when I felt like an outcast for my career choice. 

Truth is, I'm well established now, but business can be lonely, and I still talk to my biz bestie almost everyday! 

It can be excruciating to feel different from everyone else in the room (especially when you're just starting out), and having the ability to check in with someone who gets the ins and outs of your reality can be so helpful.

Sidenote: If you need more support like this, join us in Creative Money Awakening - you will find your people!

The holidays can be a tough time in general for many reasons, but it's also a great time to check in on all those energetic leaks and boundaries you've got in place for your money mindset & business. 

Being an entrepreneur sometimes means you're going to feel like the odd one out, but guess what - that's not a bad thing!

It's not normal to start a business and share your creative work, but you didn't come here to be normal!

You came here to make waves, build wealth, and change the world with your message, so take steps this season to protect your money mindset & business. 

When it comes down to it, you can't let their questions, confusion, or well-meaning-but-bad advice deter you from your dream. Trying to please everybody is a shortcut to madness and a colossal time waste.

And between us? 

Nothing triggers some people like someone going after their dreams. Your creative biz goals might upset people, annoy them, or even trigger them.

But they’re not who you’re showing up for.

You are allowed to have a thriving, beautiful, money-making business doing what you love, and I am so here to help you make the journey as easy as possible.

Hop on my Epic Email list, and when you want my support, join us in Creative Money Awakening, where we do this deep inner work around creative money blocks every day. 

Here's to your richer life & biz!

Jess xox