💌 What’s happening this week:

• Lazy or fear of burnout… here’s what I learned…

• Journaling prompt: An AI journaling prompt?!

• 32 Colonial detox ideas (to stick it to the system!!)

• My 2025 planner system (this needs to be updated!!)

Hi friend,

I didn’t expect the conversation I had with my parents about ‘not working very hard’ in my previous newsletter would resonate with so many of you!! 😭

Thank you for your replies and messages - I am behind on my inbox, so I will be responding to those soon!

Anyway, I’ve been ruminating a lot on this topic of ‘being lazy’ vs. my fear of burning out again… and why my parents think that I’m not working very hard and applying myself.

I think I’ll have to give some context to all of this, though…

When I started my previous business, The Quirky Pineapple Studio, I:

• Was 25 years old (wow, that’s really young LOL)

• Only had 1.5 years of corporate experience under my belt

• Recently moved to Spain permanently

• Was trying to make a name for myself (because no one knew who I was)

And I think for many years running that business, I operated in the zone of:

🤨 MUST prove to my parents that I made the right decision to quit my full-time job

🤨 MUST prove to my parents that I also made the right decision to move abroad

🤨 MUST prove to all the people who thought I was stupid for leaving everything

🤨 MUST prove to people that I am trustworthy, am an expert, and know what I’m doing (all in the name of getting clients)

🤨 MUST prove to others that I can make money MY way and not the traditional corporate career way, to show them that they’re wrong

As you can see, there’s a lil’ bit of a trend here… I was trying to prove myself A LOT. I will also say that at 25 years old, with no ‘real work experience’, I just had a whole different type of energy going into business!

I mean, I had way more energy back then to DO a lot of things that allowed me to scale the business, hire contractors, host workshops around the world, get featured in media outlets, all the fancy things…

When I look back at those years, in my mind… I WORKED MY ASS OFF. I worked HARD to make all of those things become a reality, to get to a point in the business where it paid for my lifestyle and home expenses, and even to employ my partner!

So when folks say I ‘don’t work hard’ now, I almost get a little triggered because… y’all… DID YOU NOT SEE THE PAST 8 YEARS?! I’ve been working hard!! 

Then, when the burnout hit, I had a week where I woke up and couldn’t move my neck because of stress, my mental health was at an all-time low, and I couldn’t sleep at night due to a lovely combination of anxiety + pressure + stress…

I started therapy, worked with a life coach, took an accidental sabbatical turned adult gap year, and then let my creativity play.

And this year, I’ll be honest… I’m working again and putting things into motion, but there’s a part of me holding myself back because a quiet voice in my head is thinking, “We cannot get back to burnout mode.”

Which has resulted in doing the bare minimum, dipping my toes in just enough into something to make it work, and celebrating my progress and efforts, all while knowing if I just applied myself a little more… I could do more. And not in that toxic productivity, hustle culture, bigger is better mentality - but I could be contributing more to build the lifestyle I want instead of living day-by-day with what I have.

I guess it’s nuanced, right?

I’m living in the present moment and creating pockets of joy and creativity for myself, but I am not laying TRUE foundations to thrive. I am a little past surviving, but not enough where I can actually make long-term decisions because I just ‘try a lot of things’ and don’t go deep with one to reap the benefits. 

For the past 2 years, I was afraid to LOCK IN (as I like to say lol) for fear of burning out again. So I made due with what I had, lived in the present moment, enjoyed creative flexibility, and celebrated all my small wins like they were big ones…

And now that I’m getting older, my parents are getting older, and I’m thinking about legacy (whoa, big word here) - what I have, although intentionally built and something I love, isn’t enough for the bigger vision I have…

Which means, I will need to work a little harder using the tools I have to avoid burnout and not be afraid to ‘go all in’... even if it sounds really scary.

Anyway, friend, I feel like this was a LONG ASS RAMBLE 😅 But if you felt similarly, I’d love to hear your perspective and what’s come up for you!

I don’t think I’m lazy, I just need to tell my body that it is safe to go all in and work hard now so that I can live my soft life at 40 or 45 years old (my delulu idea to retire by then… but currently not plausible with my income haha)

✍️ THIS WEEK’S JOURNALING PROMPT

Use this prompt with AI to turn it into your ‘reflection tool’:

“Act as my 90-year-old self. Based on everything I've shared, what advice would you give me?”

I actually found these prompts from Ali Abdaal on his Instagram and LOVED them! This is similar to what our most recent guest speaker shared about in the Plans to Progress Lounge and how we can use AI as reflection tools for productivity and goal-setting. After using this prompt, I followed up with a few more questions and then journaled on everything that came up. Let’s just say… ChatGPT really called me out 😫

💻 THINGS THAT STUCK OUT TO ME

• 32 COLONIAL-DETOX IDEAS: I loooooved this carousel I found from @oumnia.boualam and how we can detox ourselves from colonial language, routines, and habits. #4 and #15 are some of my favorites.

• LIFE ADVICE FOR CREATORS: I honestly wish someone had told me this when I was starting my own business back in 2017. This reel from @colinandsamir gives some solid advice about ‘quitting your job’ to make ‘creativity’ your full-time thing. Now that I have some semblance of regular jobs, it’s taken SO much pressure off me to monetize my creativity.

• WELLNESS HABITS TO START TODAY: LOVED this article from The Everygirl! Also, it felt good to know that I already have 3 of these habits built into my Notion dashboard and routine!

🗓 PREPARING FOR THE WEEK AHEAD

🌻 GOODIES YOU MIGHT HAVE MISSED

2025 Planner System | bullet journal, business planning, budgeting

I recorded this video at the beginning of 2025 with the idea to use 3 different planners - my bullet journal, a business planner, and a budget planner.

I’ll need to do an end-of-year review on these because let’s just say… I didn’t stick with all of the planners I have here 😅

🤝 HOW TO WORK TOGETHER

Want to work together to create time and space for intentional connections? Here are a few ways to do that through marketing support, journaling, and education.

• 📓PLANS TO PROGRESS MEMBERSHIP: A quarterly membership for big dreamers to intentionally plan each month with the accountability to transform your ideas into actionable steps and projects. Join us inside the Lounge here!

• ⭐ SIGNATURE BRAND & WEBSITE DESIGN + COPYWRITING PACKAGE: Get 2 brand strategists on your team to elevate your brand visuals, website, and messaging. We have 2 spots to start this summer. Learn more and apply here.

• 🇪🇸 JOIN ME IN SPAIN!! IN-PERSON PLANNING RETREAT: September 2026. Granada, Spain. 6 days, 5 nights. 10 spots available. Join us for an intentional week of cultural immersion, good food, and intentional time for planning and sharing with a group of like-minded people. Learn more and reserve your spot here.

A few small logistical things I’ve considered moving forward for the rest of the year:

• We are changing email platforms in September! The email address you will be receiving emails from will be coming from [email protected] 🎉

• I am considering dropping the cadence of this newsletter to 2x/month instead of 4, so that I have time to build out other projects (still need to think about this one)

• I’m building out 2 different projects, launching at the end of September - think planning templates, a peek behind my Creator/business journey, and some free monthly journaling time

When I tell you I had some sort of epiphany that I need to lock in to create my soft life, I had to hear that message probably 21824 times in various settings!! Whew… lots to sift through.

Until next time…

💖 #stayfierce,
Cassandra