For a great number of full-time employees—Millennials, in particular—joining the gig economy is an enchanting prospect. Only to be one of the adventurous digital nomads, taking to social media to share Southeast Asian adventures while working from Macbooks in coffee shops.
Being a member of the gig economy—as a freelancer and entrepreneur—affords many people the opportunity to quit their “real” jobs and travel the world while earning a living. It can also create a more appealing work-life fit through unparalled time and work-type flexibility.
To be clear, this lifestyle isn’t all rainbows and sunshine. The vast majority of participants in the gig economy work very hard and experience the chaotic ups-and-downs of self-employment. Moreover, Millennials who purposely choose gig employment are often frowned upon by more traditional employers, friends, and even family.
To be clear, the gig lifestyle isn’t all rainbows and sunshine. The vast majority of participants in the gig economy work very hard and experience the chaotic ups-and-downs of self-employment.
To shed more light on why so many of us are making this shift, I reached out to ten Millennials who left their jobs to join the gig economy and asked them to share exactly why they made the leap.
Selena and Jacob Taylor
In 2016, Selena and Jacob Taylor left their comfortable lifestyle in Los Angeles and set out to travel Europe for what they thought would be just three months. They used their complementary skill sets of writing and photography to document their adventures on Instagram. Fast forward nearly a year later, the couple live in Amsterdam where Selena is a part-time marketing consultant and Jacob freelances remotely as a videographer and photographer.
Now with more than 38,000 followers on Instagram, and a travel blog specializing in curated travel guides and beautiful photography, the couple behind Find Us Lost is getting noticed by brands. While now confident in their decision to leave Los Angeles, it wasn’t that easy at first. “We both tossed around the idea of living abroad in Europe at some point in our lives," Selena shares. We love traveling and knew if we had the opportunity to move abroad or travel and be financially secure, we’d take it. I was working full-time out of an office in Los Angeles, so it was a scary thought for me to just up and leave. Finally, we both reached a point where we said ‘let’s go for it.’ My biggest fear was putting ourselves in a situation where we’d be desperate for work, but that never happened. I truly believe if you’re passionate about a lifestyle change, you can make anything work.”
Their biggest struggle since making the leap to the gig economy? The need for new skills, says Jacob. “Growing our blog, Instagram brand, and freelance work has required learning new skills that were at one point completely foreign to us. Things constantly change and develop, so we’ve had to redo a lot of the original work that we spent long hours on. We’ve had to find a balance between wanting things to be perfect and being pragmatic—it’s a lesson we’ll carry as we continue to grow our business.”
“We’ve had to find a balance between wanting things to be perfect and being pragmatic—it’s a lesson we’ll carry as we continue to grow our business.” - Jacob Taylor
Tomas Laurinavicius is a lifestyle entrepreneur and blogger from Lithuania. Currently the creative partner at Just&Tom, Laurinavicius is also a content marketing and branding consultant to businesses like GoDaddy, Oberlo, and Designmodo. He built and recently sold a popular design blog, Despreneur, and now writes for Forbes, The Huffington Post, and Observer while currently traveling through Bali.
I asked Laurinavicius to share a bit about how he got started in the world of consulting. “I always dreamt of freedom,” he explains. “It was never about the money I make, but about the wealth of options in lifestyle and business. I started designing and blogging back in 2007 and worked hard to improve my skills and connect with people. Now, I have connections and work examples that sell better than I do.”
When it comes to his biggest struggle as an entrepreneur in the gig economy, Laurinavicius shares, “Selling out. Cash flow is ensuring that your business is functioning and can grow, so you must ensure there is money coming in. That’s very hard when you set out to change the world and consequently need to face reality, which means taking almost any client just to make sure you don’t go out of business. With time, it became easier to land clients who aligned with my values, but it’s one of the biggest challenges at the moment.”
For more about what Laurinavicius learned running Despreneur and traveling while working remotely, you can read his article on choosing what is right for you.
“I always dreamt of freedom. It was never about the money I make, but about the wealth of options in lifestyle and business.” - Tomas Laurinavicius
After graduating from college, Caroline Beaton worked as a secretary at a law firm, a marketing coordinator, and as an editor at Elephant Journal. When none of these full-time roles provided the kind of life she wanted to lead, Beaton decided to break out on her own. “I was certain that I wanted to be a writer, and I eventually got to a point where I knew I could make a living writing on my own, so that’s when I left."
Now, Beaton is a freelance speaker, cartoonist, and workplace psychology journalist, writing for more than 100,000 monthly readers across publications like Forbes, Inc, and Psychology Today.
Looking back, Beaton realizes there were several reasons why she was unsatisfied with "standard" employment. "The main being that most businesses are just so inefficient, and that frustrated me," she elaborates. "At my last day job, our CEO would come up with a project idea that would have taken me a day to finish if a bunch of different people weren’t involved—but instead the project would take months, or more commonly, never materialize. I’m an impatient doer by nature, and I felt like I could be accomplishing literally five times as much if I was doing it by myself. I work well on teams but I don’t enjoy being on teams. Departmental teamwork isn’t as fulfilling to me as bootstrapping something independently.”
Beaton offers solid advice on getting established as a freelance writer. “Start small. I wrote for random, small company blogs; then I began writing for a publication, Elephant Journal, that relies exclusively on reader submissions, so I had a better chance of getting accepted. I worked my way up byline-by-byline to Psychology Today and Huffington Post before I cold-pitched a column to the Forbes “30 Under 30” producer. Writing for big magazines takes a lot of work and a lot of rejection. My pitches are still rejected 14 out of 15 times from publications I don’t already have relationships with.”
Beaton also suggest that freelancers “pitch a niche” in order to get noticed. “Editors want to know why you’re qualified to write about a certain subject matter, and they need to be able to trust you with it. Whenever I send a column pitch email, I include what my beat would be about, why that publication could benefit from it, and 5-10 sample headlines.”
“I’m an impatient doer by nature, and I felt like I could be accomplishing literally five times as much if I was doing it by myself. I work well on teams but I don’t enjoy being on teams.” - Caroline Beaton
Talia Koren is an influencer marketing consultant, freelance writer, and former Elite Daily staff writer based in New York. She writes about personal finance, healthy habits, and content trends, and recently helped entrepreneur and award-winning writer Jared Kleinert with the launch of his book, 3 Billion Under 30, which chronicles the global contribution of Millennials.
Unlike many other freelancers, Koren didn’t land herself in the gig economy completely by choice. “I started freelancing after my whole team was cut from a large online publication. I do plan on freelancing for as long as possible because I now have the freedom to choose my clients, the work I do, and set my own pace. Freelancing also allows me to help my clients in the best ways I can, without the restriction of a job title or department.”
Koren’s biggest struggle since making the shift to the gig economy last year? “Learning how to manage my time! I have no problem sitting down, focusing, and getting to work. The problem is knowing when to take a break. I have to force myself to get out of WeWork or my home office (my bed) or else I'd just never stop working to go above and beyond for my clients.”
“Freelancing also allows me to help my clients in the best ways I can, without the restriction of a job title or department.” - Talia Koren
Alexandra Mandel currently contracts as Head of Community Growth for Unsettled, a coworking retreat company. Mandel also consults in sales and community growth for Summit Series—a gathering of innovators and creatives.
“I left my full-time role because I craved flexibility in my daily schedule and the freedom to work where I felt most comfortable and productive,” shares Mandel. “The hardest part for me was just having to be somewhere at a specific time, everyday. That makes me feel super spoiled to say, but we live in a world where we can take our laptop and work from anywhere. Why would I choose to instead be in an office in downtown San Francisco every day?”
In the beginning, building relationships was everything for growing her business. Mandel explains, “I worked my network to get my first two clients. I was three people removed from one of them and still was able to build enough credibility and trust to land it. Don't be shy to ask friends of friends, acquaintances, or family friends for intros. Lots of people are uncomfortable doing that, but what I've found is that if you make your intentions known and really go for it, people respect the hustle.”
“I left my full-time role because I craved flexibility in my daily schedule and the freedom to work where I felt most comfortable and productive.” - Alexandra Mandel
Even after graduating college with around $28,000 in student loan debt, Zina Kumok had it all paid off in three years—on an annual salary of just over $30,000. She’s been featured in Time, USA Today, and LifeHacker and now writes and speaks about personal finance.
Kumok didn’t join the gig economy because she wanted to sell all of her belongings and travel the world. As she explains, “Once I started making as much freelancing as I did in my full-time job, it made more sense to quit and see what I could do with a full 40-hours a week. I typically have between a dozen and 20 writing and content marketing clients in the financial space.”
As someone who’s personally been through and documented—on Debt Free After Three—the same struggles her readers are now dealing with, she has instant credibility in her industry. “I paid off my student loans in three years, and having a story like that makes me more recognizable to clients,” says Kumok. “People want to know that you've lived what you're writing about.”
Even still, the freelance life isn’t without its struggles. “Each month is different, so the hardest thing has been predicting where my business is going. I'd recommend that anyone interested in freelancing create an emergency fund so they don't go scavenging at the bottom when times are tough.”
“I'd recommend that anyone interested in freelancing create an emergency fund so they don't go scavenging at the bottom when times are tough.” - Zina Kumok
For half of the day, Justas Makus is the CEO at Just&Tom, the content marketing and branding consultancy he runs with Tomas Laurinavicius. The other half of the day, he’s a blogger for publications like Influencive, Business.com, and Entrepreneur.
Markus can’t imagine working for someone else, ever again. “I was working for a bank, and I didn't like it. So, I decided to start working online. I prefer to plan everything by myself. I can choose my own clients and it allows me to travel a lot. I've been to more than 40 countries, and now I'm skipping winter in Lithuania by living in Bali.”
Business wasn’t great in the beginning. Markus had a bumpy road to eventually working his way up to collaborating with companies like GoDaddy and Smashing Magazine. “The first year of freelancing was kind of hard because income was unstable. But after pushing through that difficult time, it was much easier. The more you write, the more people see you, and it's easier to get a job after putting in enough hours.”
“I can choose my own clients and it allows me to travel a lot. I've been to more than 40 countries, and now I'm skipping winter in Lithuania by living in Bali.” - Justas Markus
Dr. Aviva Hirschfeld Legatt
As the founder of VivED Consulting, Dr. Aviva Legatt coaches students one-on-one to apply for college. Legatt is an educator, was on the admissions committee at The Wharton School, and is an affiliated faculty member at the University of Pennsylvania. She now helps thousands of students get into their dream schools.
For Legatt, leaving her day job was a calculated risk with a clear safety net. “I quit my job as a university administrator in 2014 for a couple of reasons. One, I was in the last year of my doctoral program and knew I could finish my dissertation more quickly if I had more flexible hours. To make ends meet, I started freelancing for college admissions counseling companies and for Penn. If my freelance experiment failed, I had the safety net of finishing the doctoral program and finding another job. The second reason I wanted to leave my job is because I saw a better pathway for my personal and professional growth in starting a business versus working full-time in university administration. I craved more freedom and flexibility over my schedule, and to shape my choices of projects, collaborators, and professional development opportunities.”
With the highly personalized nature of her freelance business, Legatt has had her fair share of struggles along the way. “Because of how I got started, and given the personalized guidance I provide, it's been a struggle to scale. When you're a bootstrapping business owner, you always have to balance cash flow with the desire to invest in and scale the business. With a recent revamp of my website, better use of my email list, and soliciting feedback from customers, I'm working on new free content, including a new ebook, that will help me get critical information out to more people. My main goal for 2017 is to publish information and resources that add value to students and families. As I use this goal to guide my efforts, my business continues to grow.”
“I craved more freedom and flexibility over my schedule, and to shape my choices of projects, collaborators, and professional development opportunities.” - Dr. Aviva Hirschfeld Legatt
Brittany Ann Cool
By creating highly shareable short films, gifs, and visual content for global brands like Alaska Airlines, Lord & Taylor and Subaru, Brittany Ann Cool has built an impressive list of clients since starting her freelance journey at the age of 21.
Joining the gig economy wasn’t just about the lifestyle flexibility for Cool. When she was 21, she made the conscious decision to be a freelance photographer. “At the time, it was also an act of rebellion—mostly against the steady, secure, pigeonholing career track my parents insisted I go on. I was determined to make a living solely on individual creative endeavors. Photography is also a very physical job at times, and being at a desk all day did not interest me. After all, growing up I was the kid that couldn't sit still for very long.”
Despite her successes, there’s been a lot of hard work, adaptation, and learning behind the scenes. “I’m proud to say my clients have come to me specifically for my artistic direction, not because they need any run-of-the-mill photographer,” Cool shares. “I’m continuously staying up on trends and new software, and this has allowed me to expand the services I offer. I’ll admit, I still struggle with networking. My advice for freelancers is to get out there and meet people. It’s important to not only meet with potential clients, but to meet other people within your industry, and share information face-to-face. Working for yourself is often very isolating. The benefit of learning a new skill from co-workers does not always exist in the day-to-day life of a freelancer—go out and make valuable connections!”
“I was determined to make a living solely on individual creative endeavors. Photography is also a very physical job at times, and being at a desk all day did not interest me. ” - Brittany Ann Cool