Entrepreneur Diaries

I made something that took on a life of its own. It surprises me every day and gets me teary-eyed just thinking about it. 

I’m talking about The Squad 🎉, my soul crew of eccentric entrepreneurs determined to lift our families, communities, and ourselves with the beauty of our work and the abundance it creates.

We’re the gorgeous black sheep escapees of the systems designed to crush us into conformity or shut us out entirely. We’re not looking for a seat at your table, we’re building our own damn banquet halls. We’re doing business radically differently: informed consent is our top marketing value. And believe you me, our ethics are making us abundant AF, not trapping us on the economic struggle bus. We’re rested, well-nourished, ecstatic from taking mid-day breaks to skate on the beach or swim in the river, and our nails are perfect- because we don’t neglect ourselves or our needs in order to scale our businesses. We know our joy is important. We make ourselves known & heard, and we’re OK with triggering the fuck out of the wrong people as we validate and empower our people.

If this sounds like a magical business oasis filled with magnificent muses, it’s because it is. But it’s no fairy tale.

And 3 years ago, when I opened my business, I never would have guessed that such a place could come from my humble stylings. Because, 3 years ago…

… My nervous system was absolutely shot.

… I still thought some authority figure needed to give me permission for absolutely everything.

… I’d been on the struggle bus forever and I didn’t even know there was hope of ever getting off.

… I was so used to being undervalued I hadn’t yet built the belief that there were people out there more than willing to pay me properly.

… I still believed the “rules of business” and the concept of professionalism that had been drilled into me in corporate.

… I hadn’t yet realized that just because I was skilled or capable of doing something that people were willing to pay me for didn’t mean I actually wanted to do it.

… I hadn’t clarified my desire for my business beyond proving some mothafuckas wrong.

Wow, listing that out just slapped me in the face with what a massive personal transformation I’ve undergone between February 2021 and now, at the tail end of June 2024.

I want to tell you the tale of how The Squad came to be. Because it feels like a freaking miracle, but I learned how to set the conditions to make such miracles possible. 

May this story bring you hope and inspire you to take stock of the beauty you create around you. ❤️

Isa Opts Out

Oops, I Started a Business

In February 2021, at the height of the COVID-19 Pandemic: I rage quit my cushy corporate job when I found out how much less I was being paid than the mens.

I had no clue what I would do next.

It was an uncharacteristically impulsive move. I’d been there for nearly 6 years, I’d just been promoted, and I was in the midst of building out my own team that I had hand-picked and personally trained. I’d poured a lot of my energy, time, talent, and dignity into conjuring a profitable empire for someone else in an industry I found unexciting and too drunk on unchecked power for its own good. And I never even got to enjoy the fruits of my labors. In a word and an expletive: it fucking sucked.

Driving home one night, I was bombarded with a sudden loud and insistent idea: “I already built a marketing agency for someone else. Why not just do it for myself?”

I was aghast at my own audacity, the words of my former boss echoing in my head about how I didn’t do it alone and how much I was overvaluing my skillset.

Not to mention a lifetime of toxic conditioning from patriarchy, racist systems, neurotypical society, heteronormativity, and abusive relationships- all of which were deeply invested in me accepting the belief that I mattered less than other people, that I was a nuisance or a burden whenever I wasn’t conforming, and that even if I was being harmed or oppressed- me speaking up about it was actually the greater injustice.

Where. The fuck. Did I get the nerve to just… opt out? To say, “Fuck a seat at your table. I’m building my own damn table.”

I still don’t know what possessed me. But I’m so glad it did.

So, I did it for myself. I cashed out my 401K and opened my own agency with about 36 marketing services, a few contractors I adored, a big investment in a business mentor & entrepreneurship container, and a metric shit ton of constant anxiety.

…And, I had so much to learn.

“Away” Isn’t a Direction

But like, What Do I want?

The first few clients & leads I attracted were variations of my former boss: nickel and diming, trying to squeeze more work out of me than what was paid for, or going with the male-led agency even though they liked my proposal better because they were worried about the longevity of my new business.

(Rage footnote: They were going to ask my competitors to execute the vision I pitched in my proposal until one of them grew a conscience and asked me how much I’d charge to allow them to do so. Spoiler alert: the fee I responded with was expensive. I didn’t get paid and I never heard from them again.)

At the beginning of my busines, I was confronted again & again with what I didn’t want. 

🤬 To be overworked & underpaid

🤬 To have my work disrespected & undervalued

🤬 To have to answer to or even just regularly interact with obliviously privileged corporate dude bros

🤬 Endless done-for-you work I found boring or overwhelming

🤬 “Make it go viral” type of requests

🤬 Men booking my 1:1 marketing consultations just to hit on me

One day, my business mentor, Cera Byer, said, “Away isn’t a direction.” And it changed my freaking life.

It finally became clear to me that I needed to figure out what I DID want.

But, given my conditioning, this was a lot harder than it sounds. I’d been taught my needs were burdensome and actually personal failings on my part. I was completely dissociated from my wants. 

Just Cuz I Can Doesn’t Mean I Should

I Don’t Want To Do It For You

I realized I’d been confusing “can do” with “want to.” Spoiler alert: they aren’t the same thing. At all.

I can do a lot of stuff. I can do less stuff really well. I enjoy doing still less. I want to do less still.

From 36 services, I whittled it down to 5 and counting (as in, subtracting)- and everything in my business got better.

Similarly, I can help many different types of businesses and people with their marketing. That pool gets narrower when I factor in who I am particularly suited to serve. It gets still narrower when I’m honest about who I actually enjoy working & interacting with regularly.

I narrowed down my client personas from anyone who would pay (the things money terror will get even a seasoned marketer who knows better to do 😅) to small business baddies & rebellious personal brands in the fields of health, wellness, the creative arts, social justice, and fellow creative agencies. When I did, everything in my business got better.

And the more I attracted my people, the more I realized how much mainstream business containers and marketing strategies were undeserving them.

My clients are smart AF. Creative AF. Uniquely talented AF.

But something emotional kept happening when it was time to tell people what they had on offer. It got worse whenever they didn’t get the sales & engagement results they wanted- and most would default to interpreting this data as “I’m not good enough.” Marketing brought up the self-worth wounds they didn’t even know they had. Sales exacerbated their scarcity mindset, money terror, and poverty shame. Criticism shot holes through their faith that their goals were achievable and within their reach. Entrepreneurship was forcing them to confront all sorts of unprocessed trauma and long-repressed grief, rage, and shame when realizing how deeply the systems they thought they were forced to conform to had wounded them the second they realized they could opt out.

Agency feels deeply foreign to those who are used to having their power stripped away over and over again. 

All the rules change. Like if you woke up one day and gravity stopped applying to you.

The world- and yourself- feel alarmingly unfamiliar.

They don’t tell you this enough, but the road to empowerment is challenging, scary, & confronting.

And this is why Isa the Marketing Confidence Cheerleader was born. Because my clients need & appreciate more than just traditional marketing consulting. As your Cheerleader, I’ll hold your hand on the scary road to fully claiming your power. I’ll help you imagine a better way. I’ll validate that your dreams are worth the pain of growth. I’ll make places for you to rage and grieve the systems of oppression you’re leaving behind. I’ll make places where your messiness, your noncomformity, your inconvenient emotional experiences will be met with love. And I’ll help you find the song you can sing when nothing is holding you back. I’ll remind you as many times as you need that you deserve to be heard. And when you are, your people will find you. The money will find you. The support will find you. New beauty will spring up around you.

So, I hesitantly started referring to myself as the Marketing Confidence Cheerleader and selling 1:1 appointments with me as a sort of hybrid pocket marketing director and confidence fluffer.

I was nervous AF, I’d made up Marketing Confidence Cheerleading after all. Would anyone want it? 

It turns out, yes. A whole lot of people did.

Massive Unlearning

Leaving the “Shoulds” & Systems That Have Done Me Dirty

In fact, my clients told me they’d been waiting for someone like me to offer something like this.

And by “like me” and “like this” they meant all the things I’d been told were “unprofessional” to talk about for so long. In my “safe” jobs, so much of my identity, so many of my experiences were deemed too “political” to share and still expect to sell anything.

Lies.

When my soul-aligned clients started working with me, they’d leave me reviews like this one from bonafide punk goddess Star Matriarch:

“Isa's marketing services have been what I needed for so long. As a BIPOC creative with a host of personal 'issues' surrounding marketing and branding, I greatly appreciate the compassion, empathy, support, AND creativity she's provided. She's worth her weight in gold.”

Clients would tell me they finally had the courage to launch their business, to market an offer they’d been worried was too “weird.” They’d tell me I boosted their confidence enough for them to raise the price and then they sold more than ever before. Some would even tell me that I’d helped them out of a deep dark gloom.

And I realized I loved being their cheerleader. More than strategy. More than analytics. More than making creative campaigns. More than boosting SEO. More than copywriting even- my first love which got me into marketing in the first place.

I found that cheerleading filled me with energy rather than drained it. I’ve still never had a single cheerleading session that I dreaded.

And I couldn’t help but notice the difference between delivering on cheerleading and delivering on the traditional marketing done-for-you services. Mind you, these done-for-you services were ones that people were more than willing to pay me for and that I could do and do well. But it was a major, undeniable difference. 

Though several mentors advised me to double down on these services because they would be the most profitable, I leaned into Cheerleading.

As Marketing Confidence Cheerleading started taking off, I’d have periodic anxiety bursts about how it felt too good to be true. How could it be real that I could make a living doing something I totally made up? How could that possibly be allowed?

Luckily, I had one of my favorite scenes from one of my favorite movies to soothe me: it's from The Princess Bride where Wesley & Princess Buttercup are running into the Fire Swamp to evade Prince Humperdink’s army.

“We’ll never survive!” laments Princess Buttercup.

“Nonsense!” Wesley says cheerfully. “You’re only saying that because no one ever has!”

This is basically my attitude now.

Bolstered by Cera, my business coach, and the powerful pull to keep exploring this strange Cheerleading brain-child of mine, I kept going… and fucking up. A lot.

Wobbly Path to Empowerment

The choice to drop victim mentality was harder than I thought

Giving myself what I wanted was unfamiliar AF. People paying, celebrating, and validating me felt unfamiliar, AF.

And so my nervous system promptly went haywire- and I started making some interesting um, choices.

Humans are hardwired to correlate familiarity with safety- however linked the two may or may not be.

So while I was highly familiar with being locked on the struggle bus and longing to get off- when I actually did stumble into a world full of freedom, rainbows & butterflies, my body confused it for extreme, imminent danger.

The very same month I made the highest ever profit in my business, I was getting in deeper with a man who would scream at me for everything from rollerskating to having exes to loving my dog more than I loved him.

That’s right, I’d rage quit, conjured a profitable business out of thin freaking air, gone no-contact and moved 1,000 miles away from my controlling family, signed a bunch of perfectly aligned clients… and promptly chained myself to a man who felt entitled to tell me what to wear and where I wasn’t allowed to go and who I wasn’t allowed to talk to and what I wasn’t allowed to believe. Even how I wasn’t allowed to feel!

If you’re going, “What the hell, Isa??!” You’re not the first, LOL. I confused a lot of people with this period of my life.

I have learned to have a lot of compassion for that Isa. She clearly had a lot of trauma she hadn’t yet worked through.

Faced with her very first taste of true freedom, she panicked and unconsciously sought to regain the familiar dynamic of being controlled that she’d been trying to escape her whole life. It wasn’t a conscious thing. It was a lizard brain survival instinct thing.

Thank goodness I had community to snap me out of it. And remind me that there was so much more and better ahead of me than behind me.

But that radioactive relationship took a huge toll. It took 3 times for the break-up to stick. And the meaner and more controlling and more stalker-y he got, the less I was able to show up for my beloved business. It was all I could do to barely stay on top of existing client work. Marketing my Cheerleading services? Forget it.

To no one’s surprise, my sales took a nose dive and I got to cope with money stress on top of everything else. It took 3 months of deep focus on my marketing post-break-up for my finances to recover.

In that time, I was also going to therapy, talking to my coach, and trying to figure out what the hell had happened. Why had I self-sabotaged that hardcore right on the precipice of major success?

Here’s the uncomfotable truth: for me to go from victim to empowered boss-ass bitch who answers to no man- my old identity, one that I’d been at home in for more than 30 years, had to die. And that was scary AF.

I didn’t know the empowered version of myself yet, and I was afraid to meet her. Because to become her, I knew so many things would have to change. I’d need some really strong boundaries that I’d be willing to enforce even if they hurt or disappointed people. Even if my success triggered people and sparked negative reactions. Even if it became less easy to like and empathize with me. Even if it meant a lot more people would be paying attention to me and wanting a lot more from me than I was willing to give.

I’d have to reject my oldest strategy for staying safe: staying small and appeasing until I stopped being perceived as a threat.

Of course the Isa I used to be was afraid. I was about to turn her world right-side up. But since I’d been living in the Upside Down my whole life, right-side up was disorienting and alien AF.

I would have given up so many times if I didn’t have support from people who had made or were making this journey themselves.

I am Triggering & Inconvenient

And also inspiring, galvanizing, & utterly lovable

I used to believe that if I just explained it well enough, if I just comported myself impeccably enough- I’d be able to get anyone to understand where I was coming from and empathize.

I hadn’t yet accepted that there are many people in this world who, when feeling uncomfortable, will simply try to stamp out the source of their discomfort as quickly and efficiently as possible. Regardless of whether exploring their discomfort could lead to breakthroughs and growth.

Here is a list of things about myself that I have noticed make many people uncomfortable:

☄️ My confidence in my skills, talents, and myself as a person.

☄️ My decision to stop fighting for a seat at any table that doesn’t value me and build my own damn table - that’s bigger, better, and more beautiful - instead.

☄️ My financial independence.

☄️ My awareness of my beauty.

☄️ My conviction and passion.

☄️ My commitment to social justice, consent, and inclusivity.

☄️ My courage, rebelliousness, and refusal to blindly accept authority.

And here is a list of things about myself that I have noticed deeply attract people to me:

☄️ My confidence in my skills, talents, and myself as a person.

☄️ My decision to stop fighting for a seat at any table that doesn’t value me and build my own damn table - that’s bigger, better, and more beautiful - instead.

☄️ My financial independence.

☄️ My awareness of my beauty.

☄️ My conviction and passion.

☄️ My commitment to social justice, consent, and inclusivity.

☄️ My courage, rebelliousness, and refusal to blindly accept authority.

Yep, it’s the exact same list.

While some are busy shouting at me that I shouldn’t be the way I am, my people are looking to me for inspiration to give themselves permission to be as boldly and brilliantly themselves as possible.

It’s a painful thing to realize: that you can’t control how other people react to you, and that there is nothing you can do to make everyone happy.

It’s also an important rite of passage. Because as luminaries such as Tiffany Cheung & Alyssa Zander emphasize about the road to massive success: the more you are heard, the more you are seen, the more reactions you’ll be faced with. It is an absolutely essential entrepreneurial skill to be able to distinguish what is your shit and what is theirs. Just because people find you triggering doesn’t mean you’re wrong.

Just because people find you triggering doesn’t mean you should be quieter, or smaller, or even gentler in your phrasing.

*You* get to choose whether any adjustments are needed based on your own values and judgments.

Other peoples’ comfort is only something you can influence- never something you can control.

Everyone Loves a Cheerleader

But I can’t do this shit for free

I’ve gathered up these hard-won lessons like flowers to give to my clients.

I lovingly apply them like a soothing balm whenever the entrepreneurship journey feels unbearably hard, lonely, or painful.

I have vast emotional space to hold & breathe safety into. My Cheerleading clients treat it like an oasis. A place to shed burdens and masks and find their hope and stoke it.

And so many people want in. So many people want this from me. And it came so naturally to me, that it took ages for me to realize it was OK to ask for something in return.

My gifts felt like a burden when people would pull them out of me without asking for consent. Without giving anything back. Without gratitude or acknowledgment of what they’d taken.

It took a long time for me to put what felt like a fair price on my Cheerleading Services. But when I finally did, I felt galvanized. This could really work.

But, more people need this work and this support than can currently afford my 1:1 rate, so I began offering The Squad 🎉 as the group version of Marketing Confidence Cheerleading. 

I was doubly excited to try it as a group, because I was struck by how similar the blocks my Cheerleading clients were running into in regard to marketing their soul work. And all of them worried they were the only one to feel like that! I suspected finding connection with aligned community would really help.

I never could have guessed how much!

The Joy of Chosen Community

It’s taken on a life of its own.

The Squad 🎉became real in January 2024 with the most magnificent hodgepodge of money coaches, healers, private investigators, photographers, and artists.

Their mere presence inspired one another to fall deeper in love with their business, aim higher, and celebrate their growth.

They found themselves with the courage to try things they’d never tried before, bolstered by the loving and optional marketing structures offered to the group.

Each success feels like a win for all of us. Each mistake- something we all deserve to be loved through. Our growth as people draws as much acknowledgment and celebration as the growth of our profits.

The Squad 🎉is truly my happy place.

It’s what makes all the pain and struggle feel worth it. It’s what lets me know my people do exist and we need each other. I didn’t imagine my purpose, my unique medicine, my magic- all that was real before I had the living, breathing proof. My belief before it tangibly existed was well founded. And now I do get to have the living breathing proof. What an incredible feeling.

I want you to get to feel it too.

I don’t care how much you feel like you’re failing or messing up or falling short. If you have a dream, there is a reason. Realizing your vision is possible. And it goes so much more smoothly when you have aligned community to celebrate you, inspire & hype you up, and lovingly hold you accountable to your own vision, your own power, your own purpose.

If you’ve been longing for that kind of support, you’re cordially invited to The Squad 🎉.