My Journey From Saying 'Adios' To My Corporate Job, To Becoming A Freelance Cultural Storyteller And Writer

Lola Rosario

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Published: April 29th, 2023

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Lola Rosario

Founder, Lola's Lines

Founders

Employees

Lola's Lines

lolaslines.com

from Loíza, Puerto Rico

started December 2022

Founders

Employees

Discover what tools Lola recommends to grow your business!

platform

Canva

Mailerlite

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Instagram

Twitter

Medium

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Google Sheets

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Calendly

payments

Paypal

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Unsplash

other

Grammarly

Zoom

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Hola! I’m the barefoot creative behind Lola’s Lines, a copywriting and content creation service based in Loíza, Borikén (aka Puerto Rico). For the copy side of the business, I work with clients to highlight their brand’s uniqueness, sharing my motto: ‘Swapping clichés for an unapologetically bold copy.’

The content creation end is all about cultural storytelling, feminism, and raising awareness on social justice issues. Here’s where I incorporate my culture’s rich African and Indigenous heritages, along with travels to 35 countries for endless inspiration.

Since starting this journey and saying ‘adios’ to corporate, my mental health has improved dramatically (no more dreading the office Mondays). Not only that but launching the business means flexing my creative brain - nearly non-stop. After decades behind a desk, I now have wings and the freedom to enjoy a very different kind of life.

Art imitating life. Lola with Levación, by renowned Puerto Rican sculptor, Samuel Lind

What's your backstory and how did you come up with the idea?

After nearly 20 years in the corporate grind, in December 2019, I walked away from a cushy banking compliance gig to start my travel blog, La Trekista. I wish I could say it went super smoothly - it didn’t. But then in February 2020, something happened that changed everything.

A close friend and former banking colleague needing a French-to-English partial literary translation asked to hire me. It was only one chapter of Bassidiki Coulibaly’s existential analysis in his book, Du Crime d’être Noir (The Crime of Being Black), but I was elated.

That translation project and travel blogging got me brainstorming ways to turn writing into a viable freelance business. Then I remembered reading about the importance of taking your existing skills and transitioning them to your new line of work. In my former banking career, I’d worked at a half-dozen European institutions - a French bank, a well-known German multinational, a Dutch financial institution, and a Scandinavian company. My role as a Regulatory Compliance Analyst and Customer Due Diligence Officer meant I brought research, client liaison, and fraud investigative skills to my new entrepreneurial endeavor.

But there was more. Having worked for 18 months as a Spanish and French Medical Interpreter, along with a brief tango shoe sales business I had over a decade ago offered more for my toolbox.

All of these played a role in formulating my new business venture. Rather than discouraging self-talk, I used my diverse background as self-motivation.

Take us through the process of building the first version of your product.

The point of copywriting and content creation is to sell your creativity in words. The original concept behind Lola’s Lines was to craft uniquely inspirational quotes using nature and the feminine divine as a fundamental backdrop. I would then post these on Instagram to create a buzz. I also created an Etsy shop to sell a gratitude journal and affirmation cards.

None of these got much traction and rather than expend too much effort in those areas, I decided to bag the inspirational quotes idea and switch to something I had been paid for a few months prior: ghost copywriting for clients marketing their brands.

Crafting ghost copy is tricky because you don’t get your name credited to the work. Still, I realized I had a better chance of expanding on a proven skillset - I just needed to find a twist. Thinking about what I wanted Lola’s Lines to reflect, it hit me.

Just be me - writing from an unapologetically feminist and bold Caribbean Latina perspective. It’s accurate, honest, and simple. It also serves as a reminder that my work is not for everyone - and I’m absolutely comfortable with it!

Describe the process of launching the business.

There’s a general consensus that you need a website presence to build your brand. Since I knew I was going to hire a graphic designer, and that would take some time, I figured the quickest way to get started immediately would be to set up Instagram and Twitter accounts.

I went full throttle on those initially to start building an audience, but it takes time to get followers - that’s not something I didn’t already know. So, I took advantage of those two social media platforms to post and tweet almost daily. All of this was before I made the switch I mentioned earlier - scrapping the inspirational quotes. The engagement was initially slow on both platforms, so instead of getting frustrated, I went back to Medium with Plan B.

The idea was to leverage my Medium readership as a way to generate buzz around my business. I did a few things pre-launch. First, I posted a story introducing Lola’s Lines to let my 570+ followers know what I’d been up to. Then, I texted and spoke to everyone I could think of about it - my partner, friends, family, acquaintances, neighbors, and folks at cultural events.

Then, I updated my LinkedIn profile to highlight this new initiative. Though I have only 80 connections, every ounce of exposure is beneficial. LinkedIn has been great for connecting with other freelancers, researching companies, and pitching prospects.

The next part of the process was where the fun really began - brainstorming the layout and vibe of

the website. I knew I wanted it to showcase my dynamic personality and my vibrant Puerto Rican culture. So, I focused on three factors:

Colors - Bright & Warm
Nature - Evokes Calm & the Feminine Divine
Barefoot - Connecting with My Motherland, Borikén

For my travel blog, I use Bluehost. This time around, I wanted to try something different, so I went with DreamHost for its optimal speed time and server monitoring. As for the pricing differential, my choice was only a pinch cheaper. Being that I have limited coding experience, I hit Fiverr for a designer. Together, we tirelessly collaborated for nearly five weeks - much longer than I originally planned. But, in all fairness, Rohma (the web designer) met with two major setbacks while building out my site - she got infected with Covid, and also dealt with a Pakistan country-wide electric outage.

There was one mistake I made early on during the initial web planning phase, relating to a preferred minimalist aesthetic. Wanting to avoid having too many pages, and checking out no less than a dozen sites, I came across Copy Folio.

Seeing Carly Zumar’s layout, I liked what I saw and decided on only three pages (Welcome ~ Meet Me ~ Connect). One month later, I learned my lesson - nearly everyone on LinkedIn and other copywriter sites said you must have a portfolio page. And because I was more than satisfied with Rohma’s work, I re-hired her to add this fourth item to my site.

Now Lola’s Lines is nearly perfect (I don’t believe perfection exists). It meets the criteria I set from the beginning: a color scheme that breathes warmth onto each page, a sprinkling of Nature’s serenity, and being barefoot (a constant reminder that I am connected to this ancestral land).

As for initial startup costs, I kept a tight budget:

Dream Hosting & Domain: $36

Web design: $106

Marketing Coach: $60

Copywriting Courses/Subscriptions: $150

Since launch, what has worked to attract and retain customers?

Hard selling has never been my vibe. I believe one’s work speaks for itself. However, I also know running a business requires marketing, networking, and outreach. It means relationship building, and being willing to tap into the expertise of others. This last part is something I’m still learning.

So when a friend raved about one of her besties (a marketing coach), I was curious. It took me nearly 3 months to finally book an appointment. Of the many gems this coach imparted was a reminder that my brand is a direct reflection of me.

I keep this in mind with past clients by keeping in touch and letting them know of my gratitude for their business. This way if down the road they need content, hopefully, Lola’s Lines will be on their radar.

On the prospecting end, I look at it a bit differently. Rather than ‘selling myself,’ I think of it as ‘allowing them to potentially borrow a part of me.’ Typically, it starts with a reply to my cold (sometimes warm) pitch, to get an idea of my work, see samples, and my project rates (at times, per word - though I’m less keen on those).

Then it’s on to a discovery call (often less than a 20-minute Zoom or FaceTime) to set the details (guidelines, copy frequency, brand tone/target audience, contact persons) and any other logistics (e.g., payment, contract, # of revisions).

Sometimes, I’ll get contacted by a prospect who seemed enthusiastic about my pitch, but then suddenly they seem to ghost me. I’ll send a follow-up and get crickets. So annoying, but it happens. I’m still working on not taking it personally and moving on - it’s part of the business.

Be unafraid to ask people for help. You’d be surprised how many are eager to share their stories and to help guide you along the way.

As for prospecting new copywriting clients, I’m experimenting with different ways to market Lola’s Lines - a combination of LinkedIn networking, social media (IG & Twitter), and cold pitch emailing. Recently, I read about marketing sales ads - right here on Starter Story, so I am also considering it.

How are you doing today and what does the future look like?

2023 started out somewhat slow on the copywriting side. A few website glitches, slow marketing, and changes to my original niche focus all played a role.

On the content creation end, I was thrilled to grab a journalism opportunity at the Australian activist news outlet, Green Left. After pitching my story on Puerto Rico’s disaster gentrification, their editor reached out, agreeing to work with me on publishing the piece. That has been one of the biggest wins for my business, both professionally and personally. Knowing that my storytelling is reaching readers across many oceans is humbling.

My short-term goals are to continue expanding my network of activist organizations focusing on our stories, the ones often palpably missing from mainstream media. Down the line, I might consider adding a poetry component to my services. After discussing the same with my marketing coach, I’ve been thinking of taking her advice.

Through starting the business, have you learned anything particularly helpful or advantageous?

One of my first mistakes was focusing solely on Instagram as my main marketing platform. I figured I could simply transfer the IG followers from my travel blog over to Lola’s Lines to get me started. What I hadn’t considered was that the majority of those folks weren’t interested in hiring me for copywriting and cultural storytelling.

These days, while I still maintain an IG presence, my focus leans heavier on Twitter and LinkedIn. Both social media outlets give me plenty of exposure with less time commitment (e.g., fewer hashtags, and no photos required). Another platform I’ve recently looked into is Reddit (shout out to Pat Walls for setting me onto that one - am still dabbling, but so far, am getting engagement traction on my posts).

One thing I’ve learned is to keep an open mind about opportunities. Just last month, the Senior Editor of Latino Rebels (an online media outlet where I’ve been published twice), reached out to me asking to do an Instagram Live to discuss culture and Loíza’s African heritage. I was really nervous because it was my first time. Latino Rebels has 209K followers - yikes!

As it turns out, the interview went fantastically, we had a blast! With that experience, I learned to (a) set fear aside and (b) know that connections often lead to additional opportunities.

What platform/tools do you use for your business?

Zoom - For client discovery calls, and interviews for my cultural journalistic work

Calendly - To keep me organized with setting appointments

Zoho - Client invoicing

PayPal - For client payments

Yoast - SEO Marketing Tool

Linktree - For sharing my brand across multiple platforms in one spot

Mailerlite - For email newsletters

WhatsApp - This is my go-to for instant message communication with clients/interviewees

Grammarly - As an aide for all things grammar, writing style-related

Google Docs - For drafting copy, interviews, and other creative content

What have been the most influential books, podcasts, or other resources?

One of my favorite podcasts is NPR’s Latino USA, because of the show’s (a) badass Latina Executive Producer, Journalist Maria Hinojosa, and (b) commitment to ‘report on issues lacking racial equity.’

Recently, I started reading the 3rd edition of ‘This Bridge Called My Back,’ a collection of stories, essays, letters, and poems by radical women of the non-dominant culture. Edited by Cherrie Moraga and Gloria Anzaldúa, it’s a compilation of writings by warrior activists who confront a feminist movement from which their voices were excluded.

Then there’s this classic I find myself returning to more often since launching Lola’s Lines - Don Miguel Ruiz’s ‘The Four Agreements.” It’s a book I first read over a decade ago, and his philosophies remain relevant today - in particular, I am learning in business it helps when you ‘Don’t Take Anything Personally.’ Another gem I live by is “Be Impeccable With Your Word.’

Advice for other entrepreneurs who want to get started or are just starting out?

When I took the plunge back in late 2019, I didn’t have a strategic game plan. I just figured people would flock to my travel blog and the money would roll in. But that didn’t happen. I soon realized there were a bunch of things at play - one crucial aspect was I wasn’t treating my business like a business.

So this time around, I built a different kind of blueprint - one that involves networking, marketing, and perseverance. It doesn’t happen overnight, and you’ll likely have moments when you just want to give up.

Two things that especially worked for me: (a) if funds are limited, seek out free or low-cost resources, and (b) connect with those in the industry. There are dozens of copywriting courses out there, but before shelling out your hard cash, remember that ‘free is your friend.’ Start by checking out newsletter sign-ups, free mini-courses, and budget-friendly ebooks.

Lastly, reach out to people already doing what you’re looking to get into. I’ve connected with others on LinkedIn. Try social media. Be unafraid to ask people for help. You’d be surprised how many are eager to share their stories and to help guide you along the way.

Are you looking to hire for certain positions right now?

Currently, I am keeping Lola’s Lines a solo endeavor. That said, I’m certainly up for connecting with other creatives - whether to brainstorm ideas, swap tips, or simply network. Folks can reach me via email: [email protected].

Where can we go to learn more?

As a social butterfly, I’m a big believer in connecting with others. And in my business, I know it’s crucial to be accessible. I invite others to chill with me at any of my playgrounds: