Content Strategy Queen – Cassandra of The Quirky Pineapple Studio

Getting people excited about creating a grand strategy takes a lot of quirky thinking

Cassandra Le is one sassy lady on a creative mission. Bidding adios to corporate life in Washington, DC, she moved to Madrid to enjoy a life of eating tapas with her boyfriend and to start her own entrepreneurial empire, The Quirky Pineapple Studio – a virtual studio providing copywriting and content strategy services for businesses in the tourism, hospitality, and gastronomy industries. 

With more things going on than tapas on her plate, I managed to have a virtual lunchtime chat with the queen of quirk to find out how she made shizz happen for herself by kickstarting her own creative studio while also navigating life in a new homeland.

The quirky pineapple studio What was that moment like when you decided to throw in the towel for the corporate world and embark on creating your own digital nomad path with The Quirky Pineapple Studio?

Oh gosh, it was a feeling of relief, excitement, and kind of like “Oh shit, what have I done?” I had been working in corporate for a year and a half and knew that this wasn’t where I wanted to be but I was prolonging the feeling for so long because I thought if I kept giving corporate another chance tomorrow, next week, next month – it would get better. It didn’t get better.

I really tried to give corporate a shot but there was always a nagging gut feeling that this wasn’t my place. Becoming a “digital nomad” (or as I prefer to say location independent) was easier because I was moving back to a country I had lived in before and with my boyfriend after doing long-distance for so long! I was excited and eager to get started with my own business and becoming location independent!

You had previously been a travel blogger for over 10 years since you were a kid! Good on you for not spending all afternoon watching TV or playing games! So fast forward to today and you are a content strategist. Why the change in direction?

I have been blogging since I was 13 years old but it was never sustainable. It was a very heavy time-consuming hobby and activity that poured a lot of money and resources into, to try and have it grow to become a larger business – but it never took off. I also realized that as a travel & lifestyle blogger, I felt like I was just another billboard for brands and companies to go through to sell their products to my audience. I didn’t like the feeling of always having sponsored posts, ads, or campaigns and being the marketing vessel for people to sell their products.

I wanted to help brands, companies, people (in general) in a more direct way, which led me to change direction and become a copywriter and content strategist!

I knew I had skills that could be packaged and sold to really help people grow their brand, find their voice, and become more organized and streamlined with the content that they create, so becoming a copywriter and content strategist felt like the best option! These two titles combine what I love about writing and content creation that people actually need help with and is a direct way I can help others doing something that I love!

In your branding and how you convey yourself, it is evident to see you have a lot of sass – I love it. How do you think that impacted your business in being your authentic self?

You know, the funny thing is that I didn’t realise I was being sassy in my brand. I thought that the way I presented myself was “less sassy” but still feisty at times! I’ve had a lot of people share with me that they love the sass and they actually want to see more of it!

I think having the sass makes me relatable and more of an authority figure in my industry. I used to try and “hide” parts of my personality because I didn’t want to offend anyone or have someone “call me out” on an opinion I had because I hate confrontation! In the past months, I’ve realised that as a business owner – I need to take a stand and stand up for myself and my business because no one is going to respect me or take me seriously if I’m a pushover.

The sass has helped me step more boldly into who I am as a person and how I carry myself! I honestly think that if I didn’t have the sass, I wouldn’t be as confident or “sure of myself” like I am now. Of course, I struggle with insecurities like everyone but having my feistiness and sass to fall back on and take things as they come along, make it easier to always stay humble and honest.

I have been learning (and accepting) that I don’t have time for people who either want to change me, complain about me, or have something negative to say about who I am. I already work through my own insecurities, imposter syndrome, and jealousy issues in my field of work – I don’t need to surround myself with others who are bringing in negative energy into my little bubble. All it does is feed into unhealthy mindsets that I try to work through every day.

The quirky pineapple studio

What has been the biggest learning curve for you going out and doing your own thang?

The biggest learning curve is the amount of responsibility and diligence a business owner needs to have to pursue this!

When you work for yourself (and at home) you have NO accountability except with yourself.
If you get up late, no one’s there to say anything…
If you stay in pyjamas all day, you don’t have coworkers to say you look a little dirty…
If you don’t get all your work done or stay up until 4 am working, no one is there to set the boundary except yourself!

Being proactive in my business and personal life, with responsibility and diligence, has been the hardest thing I have needed to adapt to. I set my hours, I build my client experience, I am finding work and securing clients, I’m doing it all while also trying to live my life, be sociable, spend time with my boyfriend, and enjoy my new home! I’m still learning how to best structure and balance these two aspects but it’s definitely gotten better since the first few months I became my own boss for The Quirky Pineapple Studio.

Want more inspiration? Check out other People Making Shizz Happen

Its always challenging to go it alone and head into the unknown – what is the advice that you would give to those contemplating to make the change?

This is hard because I can give “practical advice” and then “soft advice”! I guess I’ll give both because they’re relevant and necessary.

The practical advice I would give someone is to figure out your means of living and decide how much money you need to save beforehand and how you plan on generating income. Of course, the first months will be slow, but this is when being proactive and constantly “forecasting” is important because you can’t arrive on the first of the month and think to yourself “Alright, I have no clients, how will I get clients for this month?”. You’ll be in the “feast and famine cycle” of having high fluxes and really low months in income.

The soft advice is to decide what you’re in the first for. What’s your “why” for doing it all and if this is something you absolutely feel called to do. Becoming your own boss, creating a business, or being a digital nomad is not all travel escapades and beautiful landscapes. Why are you doing this, what’s the point, and how badly do you want it? If you can’t say “I REALLY F*CKING WANT THIS AND HAVE DREAMT ABOUT IT” then you might not make it to the other side and find the “success” you want.

Here’s an example: people asked me before I quit my corporate job and started on this entrepreneurial location independent journey if I had a “Plan B” for my business. They asked how long I was giving myself before I knew it was time to pull the plug and go back to a “regular job”.

A lot of people I talked to said that they set their timeframe to build their business and lifestyle from 6 months to 1 year. I honestly looked at them and told them that I never even considered that this wouldn’t work. Never did I consider a “Plan B” or think how much time I would give myself before pulling the plug on The Quirky Pineapple Studio. I don’t know if that’s stupid or naive, but to me, The Quirky Pineapple Studio is MY business and I am going to do all that I can to make damn sure it works and provides me the lifestyle that I want (btw, my lifestyle & business model may change but I know that this is what I want to do).

I found you on Instagram and so glad I did! Besides watching your very upbeat daily videos, your advice has been invaluable so gracias! I even hired you for your services! What do you think is a common mishap that people starting out their own business make?

I think the common mishap is wanting to do too much. I know this because it’s what I did, too! When I first started my business, I wanted to try and fit everything under an umbrella that I called “The Quirky Pineapple Studio” – offering strategy sessions, copywriting, content creation, and at one point, portrait photography. Most of the things that I listed out, in the beginning, were activities that I loved but didn’t make sense (i.e.: portrait photography).

I think we all need to go through that phase, though, because by trying and liking or totally hating, we learn what we’re good at, where we can give the most value, and how we can best help our clients with our talents!

When I work with clients who are starting their own business (usually in travel writing or transitioning their travel platform into something bigger) many times they try to add a lot of packages and services that don’t necessarily make sense for their brand or where they’re trying to transition their new brand.

My biggest advice for working through this mishap, in the beginning, is to sit down, make a list of all your marketable skills and then go through the list again to see what you actually LOVE doing. After making a list of everything you love, figure out how you can start offering it at your own angle and unique perspective!

The quirky pineapple

Because you work your own hours #freedom – how do you manage your daily routine with The Quirky Pineapple Studio?

When I first started, I was all over the place. I would work on one thing, then jump to another, and tried to fit everything into an 8 hour day. It never worked and most days I would also get distracted because I never made clear goals for myself or create any focus for my days – it was like opening my laptop and getting on the Internet, for nothing.

Now, I’ve created a daily/weekly routine that has been working for me and keeps me sane with The Quirky Pineapple Studio! For example, I theme my days based on tasks, so Mondays are for marketing, Tuesdays are for content, Wednesdays and Thursdays for client work, and Fridays are for admin and learning.

All my tasks during those days fall into each category, which makes it easier for me to stay focused and break up my time accordingly. Another trick I’ve found works for me is to wake up, get ready, make a coffee (or a glass of chocolate milk), and journal before getting to work or forcing myself not to check my emails immediately because it drains my energy. I also only take meetings 3 days a week, and never on Mondays or Fridays haha!

What is in the pipeline for you next – both in business and travels?

I’ve got so many ideas for The Quirky Pineapple Studio for the remainder of the year and to make 2019 even better! I can’t share everything (yet), but here are some projects I’m working on for the future!

Travels —> I’m currently travelling with a digital nomad program and will be Latin America for 2 months! As I’m writing this, I’m currently in Buenos Aires, Argentina and next month I’ll be in Santiago, Chile. Then, I’ll return back to Madrid before flying back to the United States for the month of January. Other than that, I don’t have any big travel plans for 2019 – yet!

Business —> I’ve got so many ideas that I would love to start implementing and testing for The Quirky Pineapple Studio! My biggest goals are to expand my team (can’t be a one-woman show forever) and growing my community online and in Madrid, Spain. I’ve got some ideas for more workshops, education, events, and maybe some products! I’m in the beginning stages of planning – but stay on the lookout!

I bet being the digital nomad you are, you have experienced a bunch of co-working spaces with a lot of creative vibes flowing. (Let’s not forget to mention good coffee too!) What is your favourite co-working cafe or space that you have visited?

This is so hard because I haven’t been to THAT many co-working spaces! Cafes though… I’ve got a huge list! My go-to cafes to do work for The Quirky Pineapple Studio include:

Virginia: Northside Social – the best lattes I’ve had with milk that’s steamed to perfection! Order yourself one of their large cookies to snack on with your latte!

Madrid: Boconó Cafe – practically on par with the coffee in Northside Social and with a little brown sugar (if that’s your thing) it really enhances the flavour of the coffee! Want breakfast? Get one of their avocado toasts, made with thick sliced bread, avocado, and topped with grated tomatoes. Sprinkle a little salt on top and you’re set!

You develop kickass content for The Quirky Pineapple Studio but what books do you like to read to get that inspiration happening?

Some that I’ve read that really helped with some inspiration include “You Are a Badass” by Jen Sincero and “Essentialism: The Disciplined Pursuit of Less” by Greg McKeown.

Follow Cassandra Making Shizz Happen:

Facebook, Twitter, Instagram, Website

Check out The Quirky Pineapple Studio – Your Soulful Branding Workbook: The Ultimate Guide to Creating a Soulful Personal Brand


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