Reimagining Business: Why We’re Taking a Break

Did you know that our cells regenerate every 7 years? That’s kinda like saying we’re not the same people as we were 7 years ago…

I think the same can be applied to business, as well.

This year, The Quirky Pineapple Studio quietly celebrated 7 years of full-time business.

7 years running a location-independent marketing agency.

7 years building brand awareness in English and Spanish, worldwide.

7 years working with small businesses, founders, thought leaders, and more to leverage their stories and connect with their audience using copywriting and content marketing.

And while it’s a bit frightening to be here, writing this blog post, I think it’s time to finally admit that this post has been in the making for almost 2 years.

So, to celebrate 7 years of The Quirky Pineapple Studio and share what’s next, let’s walk down memory lane together. I’ll explain a little more about the decision to take a break and hit pause.

Cassandra Le leading an inclusive marketing workshop

From “Travel Blog” to Multicultural Creative Marketing Agency

I started The Quirky Pineapple as a blog in 2014, during my senior year of college. The goal was to document my senior year, what life would look like heading out in the ‘real world’, and my lifestyle changes as I got a full-time job and started building my career.

Funnily enough, that didn’t happen.

Instead, I took a ‘gap year’ to move to Spain and teach English abroad through the program, Auxiliares de Conversación with the Spanish government. What was supposed to be an ‘early-20s’ lifestyle blog about career growth shifted into a travel blog.

I documented life abroad, what it was like to be Asian-American in Spain, had a popular blog series interviewing intercultural and international couples, and even shared my own stories of being in an international and intercultural relationship.

Then when I realized teaching English wasn’t my ‘calling’ and becoming a full-time blogger (the term Creator didn’t exist then!) was not viable to the lifestyle I wanted to have, I packed my bags and moved back to the USA and secured a full-time role in my home area. The blog had another pivot and shifted from pure travel to ‘lifestyle transitions’, learning to work in corporate America, and little dabbles in entrepreneurship.

At the end of 2017, I had researched enough about ‘how to make money online’, ‘how to offer services’, and ‘how to start an online business’ (back when those weren’t very popular) and decided… I’m quitting my full-time corporate job, turning my blog into a marketing studio, and packed my bags to move back to Spain.

My mission has always been to have a business that supported my lifestyle, one that allowed me to travel the world, meet people, and support them in creating intentional time and space for their relationships – either with themselves or their communities. The Quirky Pineapple Studio’s mission has always been to help people, brands, and organizations share their stories to create deeper connections.

Since then, The Quirky Pineapple Studio has evolved and grown in ways I could have never imagined!

In these past 7 years,

  • We’ve grown to a team of 5, with 2 full-time employees and 3 contractors, and also downsized
  • I doubled my full-time corporate salary (bringing in 100K+€ in revenue)
  • Branched into different income streams (memberships, masterminds, workshops, digital products, and 1:1 services)
  • Hosted 2 retreats (in Colombia and Spain)
  • Traveled the world and met with clients in their home countries
  • Hosted workshops in English and Spanish (online and in-person)
  • Had an (unsuccessful) merch line (hah… that’s a story for another day)
  • Supported my lifestyle thanks to the business alone
  • Employed my partner!!

And so much more… that if I listed them all, I might start crying and this blog post would be even LONGER.

Of course, the original plan was to scale the business… turn it into a leading marketing agency, and grow a team of multicultural, creative marketers…

Unfortunately, after 2 difficult years (2023-2024), there have been many whispers, nudges, and pulls telling me that my original plan wasn’t really the plan anymore. Truthfully, I tried to ignore that very loud voice, yet quiet intuitive pull that I needed a break, and The Quirky Pineapple Studio needed one, too.

The (accidental) Sabbatical turned Adult Gap Year… now, Career Break?

Let’s just be honest, shall we?

I was not prepared for the drastic shifts in the marketing industry and felt I was at a crossroads between two decisions:

  1. Scale up and grow The Quirky Pineapple Studio into a leading marketing agency, pitching proposals for large contracts, and hiring a full-time team
  2. Or… scale back and reassess the offers, services, and price points we have to create a competitive advantage with AI

I chose to scale back due to many reasons, some include evolving goals, burn-out, industry shifts, and my own values and ‘dream lifestyle’.

In reality, with a big market shift to ‘quantity’ over ‘quality’ content and changing client expectations around marketing budget, as well as marketing results…

I had to decide what my next steps were going to be so that me and The Quirky Pineapple Studio could continue to offer value, provide services, and do so at a level that matched my goals and desires, as well as what clients wanted.

2023 started off as the year we were set to scale and grow, I planned on hiring up to 2 more writers, and by April 2023 I saw that the market was changing and I needed to make some decisions. Unfortunately, when you’re emotionally attached to your business and your identity is wrapped within it, making decisions for your well-being ends up getting procrastinated.

And in 2024, my decision was still put off until life decided to force my hand. In March 2024 I flew home to be with family and while there, celebrated my maternal grandmother’s life and grieved her loss. I’ll be honest with y’all – I had a bit of a ‘WTF’ life crisis moment dealing with death and the interconnection of it. I decided to scale the business back even more, resulting in what I’ve been calling an accidental sabbatical turned adult gap year.

During this time, I’ve done some pretty amazing things (not related to work) and also questioned a lot about work, and grieved what I thought I wanted work and the business to be.

I suppose I can distill why The Quirky Pineapple Studio is taking a break into 5 reasons:

  1. Burn-Out: I got burnt out in my business and trying to keep up with it. I ended up creating a monster I constantly had to feed and that was depleting my creative energy.
  2. Lack of Systems: As my business grew, my systems were being stretched and I had some real growing pains. Ultimately, I didn’t have the business infrastructure to support my growth, which led to burnout.
  3. A Bully Client: I’m not blaming them and I take full responsibility I should have set better boundaries and let go of this client early on (and probably shouldn’t have accepted the project). I worked with the client for 4 months which completely made me question my knowledge, expertise, and value. This resulted in my self-love and confidence sinking to an all-time low.
  4. Uncoupling Work & Identity: During the past 2 years, I’ve had many WTF moments and started uncoupling my identity with my work and my business. It made me re-evaluate everything I was doing and how I was doing it.
  5. Life: Life sometimes just happens and it required me to dedicate more time to supporting my family in times of grief and just heal/rest after years of grinding to build the previous iteration of The Quirky Pineapple Studio.

It took 2 years for me to come to terms with this decision and truly be at peace with it! Not saying that I didn’t feel *some type of way* writing out this monstrous blog post! I am excited to step away from The Quirky Pineapple Studio for some time so that I can re-evaluate our direction and business model and then make a more aligned and purposeful decision with intention.

new year business planning with a brand strategist at The Quirky Pineapple Studio

What Next for The Quirky Pineapple Studio and Myself?

While we’re not starting completely from scratch, we will be starting fresh.

This means that I am doing lots of restrategizing and reimagining for myself and the business.

Some of the questions I’m asking myself are:

  • What does life look like when I’m 40 or 50 years old? 
  • What type of work do I want to be doing and what is the impact I’m having?
  • What is a business model that can truly support my lifestyle, especially if ‘life happens’ and I need to jump in to support the people closest to me?
  • How can I build something that is equal parts spacious, creative, and joyful, while also making the impact I imagine?
  • Where do I fit into the world, as a Founder, and where does The Quirky Pineapple Studio fit into the world of business?

It’s bittersweet to say goodbye to a business that I built from the ground up to support my current lifestyle. It’s sad to say goodbye to a business that gave me so much and has supported so many people…

But what I do know is that I have years of experience doing what I do, The Quirky Pineapple Studio is built on a deep mission and vision, and while we are both beginning again, it does not negate all of that experience and expertise we have… We are simply bringing this along into our next journey.

I’m excited to bring you all on this journey if you’d still like to be part of our ether! I’m eager and inspired to reimagine a business that truly supports ME and MY LIFE while also providing the tools and resources so that YOU can also build something that supports you and your life.

(R)Evolutionize your Industry Content Marketing

Stay Connected as we Shift & Relaunch

To everyone we’ve worked with, collaborated with, and more over the past 7 years, THANK YOU.

Thank you to the folks who referred us, shared about us, supported us, and were part of our international and global community – we’re so grateful and appreciative of this space. I am so proud of the community that we have, the type of marketing we share and offer, and the impact that it has on our clients and their businesses.

This isn’t a total goodbye, just a pause for a while so we can do greater things in the future.

If you’d like to stay connected – here are the best places:

The Quirky Pineapple Studio

Stay in touch with me, Cassandra!

If The Quirky Pineapple Studio has helped you in any way, I’d love to hear how! If you’d like, you can send us an email (hello[@]thequirkypineapple.com) to share or drop a comment on Instagram.

If you made it all the way down here, whew… you’re a real VIPiña! Thank you, again, for all of your support these past 7 years! I would love to have you join the next chapter of The Quirky Pineapple Studio and what we’ve got planned for the future.

See you sometime soon, we just don’t know when yet. And as always, stay quirky.

Signing off for now, Cassandra 💖

P.S. Here’s the research about our cells regenerating every 7 years. Technically, our bodies don’t replace themselves every 7 years, nor are we entirely ‘different’ people from the inside out… but, that’s not very inspiring is it? A lot can happen in 7 years!

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1 thought on “Reimagining Business: Why We’re Taking a Break”

  1. You didn’t have to break down your reasons or process to get to this decision, but it was extremely insightful to read about it. Wishing you an exciting experience as you navigate through this new part of your journey — what a way to start 2025!

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brand strategist with pineapple, copywriter holding pineapple, the quirky pineapple studio

Welcome!

The Quirky Pineapple Studio (2017-2025) agency doors have closed, but our blog is still up and running with great business and marketing resources to help you apply a culturally competent and liberatory marketing strategy.

Connect with me (hi, it’s Cassandra!) for freelance brand strategy and marketing consulting, copywriting, or speaking opportunities.