Photo Credit: Phillippe Diederich
When Opportunista Lorraine C. Ladish shared one of her philosophies on entrepreneurship – that it's riskier to work a 9-5 job than to run your own business – The Opportunista needed to learn more. Author and Founder of Viva Fifty Media LLC, Lorraine has been an entrepreneur nearly all her life. In fact, entrepreneurship has always been so deeply ingrained in Lorraine's DNA that she doesn't understand how not to be an entrepreneur.
This Opportunista shares how she bounced back from living on food stamps as a single mother of two by leveraging her talents as a writer and eventually launching her own media platform and personal website. Lorraine provides an education on how to monetize writing, blogging, and editing, and offers inspiration to push ourselves to keep going despite hitting that proverbial rock bottom.
I cannot imagine having to ask for a day off at an office, have limited vacation time, and make a fixed amount of money every month. I prefer the uncertainty of endless possibility over the false security of a paycheck any day.
Let’s meet Lorraine and learn from this Opportunista.
Name: Lorraine C. Ladish
Location: Sarasota, Florida
Title & Company: Author & Founder of Viva Fifty Media LLC
Industry: Digital Entrepreneurship
Education: Some college – Literature. Never graduated because of my years-long eating disorder. I don't see a good reason to go back to school now.
You’ve been an entrepreneur for nearly your entire life, with the exception of briefly working a few traditional jobs. What did your experiences working your 9-5 teach you about yourself, both personally and professionally?
My traditional jobs actually don't add up to a lot. The few times I tried to have a job at an office with a schedule, I simply couldn't stomach it. Even when it was in an industry, like advertising, that I enjoyed.
The simple fact of having to be somewhere at a certain time every single day and not be able to leave until a certain time, would make me physically and emotionally sick. I felt unmotivated, depressed, defeated. I realized this before I was 20, and I just knew in my heart that I was not 9-5 material. This was a day and age when there was no Internet and no cell phones. Faxes were just starting to be a thing. I believe I was ahead of my time in that sense. I found ways to use my skills – writing and translating – from home. I would work remotely for sound studios. I even showed them how I really was able to work for them from another city, in the days of couriers and the first electric typewriters. When the Internet came about, I was right at home, and when social media sprouted, I took to it immediately. It was my dream come true.
Now I continue to work on my own terms and make my own opportunities using tools I could not even imagine would be available to me as a young woman. To this day I cannot imagine having to ask for a day off at an office, have limited vacation time, and make a certain (fixed) amount of money every month. I prefer the uncertainty of endless possibility over the (false) security of a paycheck any day.
You lost your income, your savings, and your marriage during the Great Recession of 2008. You became a single mom on welfare. Would you share what happened? How did you manage to recover?
I have no qualms about sharing my struggles. We all go through them. I wrote this particular one as a book called REACH! from single mom on welfare to digital entrepreneur (available in English and Spanish on Amazon). I had moved from Spain to the US in 2004 with a four-month-old and a three-year-old. I had just published a book about pregnancy with one of the largest Spanish publishers, and I was not there to promote it because I had just followed my husband to Florida as he had accepted a job offer in the States. I realized I had to kick-start my career here. I didn't know anyone and most importantly, nobody knew me!
I quickly introduced myself to local publications like La Palma of the Palm Beach Post, and they interviewed me as an author. I offered myself as a freelance writer and collaborated with them for four years. I wrote features, book reviews, and a children's section. This is just one example of making my own opportunities.
My marriage was already in trouble by then, and in 2008 my then husband and I had done a couple of years of marriage counseling, self-improvement seminars, and had undergone a trial separation. He lost his job as an engineer several times and when the recession hit. I also lost my sources of income – mainly writing for print newspapers and writing books. Nobody had money for that. We had gone through our savings and racked up debt.
I felt I had nothing more to lose, so that's when at 45, I realized I didn't want to wake up at 50 realizing I had wasted my best years in a toxic relationship. I walked away with only my clothes, my books, my laptop, a box of heirloom jewelry belonging to my family in Spain, and my two girls.
Two months later I found myself applying for food stamps. I could not find any gigs or work in my field, and I had no experience and was too old to be say, a bartender or a server. Plus I had to take care of my kids. Those were tough times. I sold my family's jewelry to pay rent, was on the charity list at school for Christmas, and received help from friends and family. But they were difficult times.
I kept myself in good spirits by running (I've been a runner since I was a kid), dancing, and spending time with my children. Every night I would write a gratitude list – everything I was grateful for. Sometimes the list was filled with simple things, like someone smiled at me. Other times it was something larger, like when an acquaintance – a school teacher – gifted me the engagement rings and wedding rings of her two failed marriages, so that I could sell them and feed my girls. I will never forget that.
I climbed out of that when I realized that I was looking for work in the wrong places. Digital publications were starting to pop up. I'd been blogging for a while – my blog was called Success Diaries (it's still up), just to keep myself going. Someone on Facebook saw that I was a writer and told me he needed someone to write some blogs about coupon savings for his website. He only paid me $12 a pop, but I wrote them like they were literature.
From there I went on to write copy for business websites. I learned about SEO and how to write for online publications. I eventually applied for and got a long-term gig with About.com, owned by The New York Times. I became the expert in Spanish for the Latina moms section.
Not long after, an old contact reached out to ask whether I'd like to be the editor for the women's section of a new digital news site. And finally, I became editor-in-chief of an online publication called Mamiverse.com. All this happened in just a few years. I always worked as an independent contractor, and I made my way back into making a living with words, just in a different medium. Had I not realized the power of digital, I may still be on welfare!
You launched Viva Fifty! as a bilingual and multicultural community that celebrates the joys of midlife. What are the three most important lessons you learned in launching your business?
First, it's most important to ship and ship fast, while you have the initial drive and passion. You can always fix things later. The website VivaFifty.com went live in a short period of time … and once it was out there, I was driven to create content for it and get all the social media handles up and going.
Second, it's important to know exactly what you are trying to create, and ignore naysayers. A lot of people questioned why I had “limited” myself to a certain age group. I didn't see it as limiting. I was simply doing what I felt compelled to while I filled a void in the digital space. There was no other bilingual blog for women over 50.
Third, you need to course-correct every few months, especially if you're working online. I eventually also launched my personal website LorraineCLadish.com as a blog. Some brands wanted to work with me, but not necessarily with the brand VivaFifty.com. I already had a following of younger women there, so it was easy to make the decision to branch out.
You’re an author of 17 books; contributor to major media entities like AARP and NBCNews; former Editor-in-Chief of Mamiverse; and a blogger. What advice do you have for entrepreneurs looking to monetize their writing, blogging, and/or editing as part of their ventures?
First of all, learn how to write. And by that I don't mean only how to spell and write a sentence that makes sense and is grammatically correct. I mean learn to create content regularly, and be both a writer and an editor. Learn how to create a story arch, and what the difference is between writing for a blog or for a news site. Learn to fact check. Learn to pitch. And learn to accept rejection and critique gracefully. Be easy to work with. Meet your deadlines. Never go missing when you're supposed to turn in an assignment.
Keep in mind that a "no" to a pitch means "no" to that pitch, not "no" to YOU. And keep pitching. Be relentless. Avoid badmouthing editors or publications via social media. Be professional. It's all really common sense, but it may be the least common of the senses.
What doesn't work is acting like a diva, defending work that can't be defended, and not being willing to work with an editor. If you want to command bigger bucks when writing online, you need to have a certain social media following and engagement. Good writing skills, being professional, and being able to promote your writing online is your ticket to getting paid to write.
Running multiple ventures can be all consuming. How have you increased your productivity as an entrepreneur?
By taking time off. This may sound counterproductive but it works for me. I now schedule my days around my yoga practice. By taking time to nurture myself. I'm wildly more focused when I sit down to work. I'm also learning to do different things at a different location. I'm writing a book for HarperCollins, and I only do this at the library or the bookstore, with Wi-Fi shut down. Then I drive back home and tackle all my other work responsibilities from my home office or even my backyard. I also plan my calendar a week ahead of time if possible. By allotting a specific day and sometimes time to each task, I avoid feeling overwhelmed. I also delegate now that I have the money to pay a small team.
What advice do you have for an aspiring entrepreneur who wants to be run her own business, but doesn’t yet have the idea?
To avoid thinking that your first idea has to be the ONE. I've had failed initiatives … but that only helps me realize what I'm not really interested in or perhaps not good at. For example, I created a line of jewelry for my business and thought it would be a success. Who knew I suck at sales like that. I enjoyed doing it, and I spent time, energy, and money. But if I hadn't done it, I would not know for a fact that retail is simply not my thing. I will do something with that jewelry. I still don't know what. But for now, I'm back doing what I do best and can monetize more easily – create content that informs and hopefully inspires.
What do you think are the skills and/or traits that entrepreneurs must have and why? How have you developed these?
I don't know about all entrepreneurs, but I personally learned to turn my weaknesses into great traits. For example, I have an addictive personality, and I have turned that into being prolific and consistent. I am also self-motivated, which I've always been even as a young kid. I don't need anyone to tell me how to manage my time or to get things done. Also, have patience, and realize that as Seth Godin says, “the long way is the real shortcut.”
Time will go by whether you pursue your passion or not. Pursue it. Now.
How do you manage being an entrepreneur with being a mom and wife?
I've always managed to combine my work with anything else in my life. I'm lucky that my husband (I'm happily remarried and have a blended family) is also a writer. We sometimes work on projects together, and he also has my back at home if I have to travel for business. That alone is a huge support. My kids are all teens and tweens so it's easier than when they were younger. If I managed to write books when my girls were crawling around my legs, imagine what I can do now that they are in middle and high school!
My eldest, 15, just asked me to drive her somewhere, and I told her I would as soon as I finish up this interview. I learn to work in bits and pieces here and there.
What do you love most about what you do?
That I get to make a full-time living writing and creating content. That I manage my own time. That I don't have to ask anyone for permission for anything. I can say yes or no to a client. I basically can make my own opportunities every single day. And I do. Are there bad moments too? Hell yeah. Every month or so, despite the fact that I'm allergic to having a regular job, I question whether I should in fact go find one. But that's usually when a client is late in paying, or I feel a bit burned out, or have writer's block. It eventually subsides, and I fall in love with my work all over again. I really thrive when I know something I said or wrote inspired someone.
How are you creating your own opportunities to live your best life?
By reinventing myself constantly. I have my down moments and doubts. We all do. But I haven't ever let that stop me from moving forward. I am always itching for a new project that will push my limits … my creative limits. I joke that I even made a seemingly big obstacle – my age – work for me. At 53, I make a living telling people how great it can be to be over 50. That sometimes surprises me.
Lorraine is The Opportunista.
Your would describe yourself as: Driven, relentless, curious.
Your kids would describe you as: A pain in the butt if you ask my eldest, 15. Inspirational if you ask my youngest, 12. Fun if you ask my stepson, 13.
The item on your bucket list that you’d like to cross off next: I don't really have a bucket list. I think what I really want to do is continue to live my life the way I do. I just wish to increase my income further, so that I can travel more with my kids and be there for them if they need it as they grow older.
Your favorite quote: Live by reasons, not excuses.
Best advice you’ve ever received: Fake it 'til you make it. I still do it.
Let me know in the comments: How has Lorraine’s story inspired you to build your own business
and create your own opportunities to live your best life?
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