To continue our study of what freelance success looks like a few years in, we’re chatting with Lindsay Tigar, a ClearVoice contributor who’s carved out a niche here and elsewhere profiling boss women and their best practices. From negotiating better pay to identifying new marketable skills to hustling more effectively, Lindsay learns from women at the top of their game — and shares that knowledge with readers.

After launching her career in New York, she went full-time freelance around two years ago, thinking at first that it might be only for a year. Instead, she began to thrive after a few months, set up her own LLC and began to hire staff. Here’s a look at how she did it and her top lessons from the process.

Tell us about your transition from in-house editor to freelancer. What was the catalyst, and what was your exit strategy?

Two years ago I was working full-time at ClassPass, a fitness company based in New York City, as their editorial and content director. It was then a fitness startup.

I was employee number 39, and took the blog from zero writers to a team of 15 writers. By the time I left we had gone from publishing three times a week to publishing six times a day. I really loved working at ClassPass. (Hey, it was free fitness classes, so what’s not to love?) It was a really fulfilling experience, but I wanted to be my own boss. I wanted to dictate my own schedule, my own career. I didn’t want to have to go into an office every day.

I was lucky to be offered the opportunity to be part of Remote Year, which is a program that allows professionals to live in up to 12 different countries over 12 months. I said yes. I quit my job, and I went freelance full-time, I booked a one-way ticket to Croatia, and I started out on the journey to really amplify my freelance career, start my own business, and see where it would take me.

with remote traveling

With Remote Year, you started traveling at the same time as freelancing? But you had a support system of sorts, through the program. So what was it like?

The first three months, I was living in Croatia, Portugal and Czech Republic, so it was not only adjusting to whole different cultures, new languages, and a whole new group of people that I had never met… but it was also freelance full-time for the first time in my whole life.

It was really the first time that I was fully responsible for every piece of income that came in, invoicing, pitching, keeping up with all of the different parts of running your own business that nobody really tells you about. It was stressful but it was also exciting. It was when I learned how to kind of roll with the ebb and flow of freelance. One month you have a ton of clients, the next you have a slower month, and you take it as an opportunity to cold-pitch.

Now that you’ve been at this for a couple years, what would you tell people?

Quitting my full-time job was both one of the most liberating and terrifying things I’ve ever done – second only to going skydiving in Mexico – but for me, the biggest piece of advice for writers who are on the edge, figuring out do I quit my full-time job; do I make this my full-time employment? comes down to monetary. My best piece of advice is save up, till you’re ready to make that plunge.

You have to focus on building up a client base, with steady anchor clients, and magazines or other outlets that you have a ton of assignments for. Get that going for at least six months at $6,000 a month. When you’re starting out that seems like a ton. I think my first month freelancing I probably made $1,500. While that was amazing, it’s definitely not enough to sustain yourself in most of the country. So save up, and that way if you have a month where you’re making only $4,000, with the ebbs and flows, you have a sort of cushion to rely on.

think about it as a quarterly income

And is that a piece of advice that someone else gave you? Or if not, what was?

But the best piece of advice that anyone ever gave me was my old editor at NBC. She said when I went freelance, the best way to look at income is not on a monthly basis, which I think when you’re in a full-time job that’s how you think about it. You get a paycheck every two weeks, you know how much money you have every month, and you know how much you’re spending.

With freelance, if you look on a quarterly basis and you take the average of what you’re bringing in, it’s actually a lot easier and a lot more reflective of your income.

Talk to us about balancing lifestyle journalism with content marketing.

The little secret of becoming a full-time freelance writer is that nobody’s a full-time freelance journalist. No one gets to go to fancy hotels all the time and review them and get paid six figures. That’s just not how it works. So while I love travel writing and would say that’s a passion, what I love to write about, honestly the biggest part of my income is content marketing. And those were skills I was able to develop while working with ClassPass and for some other companies along the way.

While I was traveling I actually had clients located in Los Angeles, New York, and Florida. By helping those clients develop their copywriting, their brand voice, helping them rank for SEO terms through SEO writing, developing a blog schedule and cadence — those were really the big moneymakers that allowed me to live abroad and work for myself full-time while travel writing was a nice cherry on top.

clearvoice payment system

We agree that ClearVoice’s payment system is fab for the self-employed. Tell everyone about it!

When you become an entrepreneur, you’re not only Lindsay Tigar writer, journalist, editor. You’re also an accountant, an assistant, an associate. All the roles in one. And one of the most annoying parts of being a freelancer, and one that kills productivity, is having to continuously follow up on, please pay me for the work I completed for you.

What’s really wonderful about ClearVoice is that you get your assignment, accept it, and at the moment you submit your story, as long as it meets the qualifications for publication — word count, follow the instructions laid out in the outline — as soon as the story is approved by your editor, you get paid instantly. I think that’s something every freelancer can appreciate, considering we all are here to make money at the end of the day.

You’ve really started to own an interesting niche on ClearVoice and elsewhere lately. How did you find it?

When I was first starting my career at 22, I had just moved to NYC from North Carolina. Like a lot of young writers, I had lofty dreams and ambitions. I had 2 suitcases, 3,000 dollars, and a big will to succeed. I started sending out my resume everywhere, interviewing anywhere I could. My first job was actually at a small business magazine that was called the New York Enterprise Report — it’s now owned by Crain’s Business. That was the first time I got introduced to this big world of entrepreneurism.

I always knew I was going to be a writer, and that was going to be my path, but I had never really considered that it was something I could do for myself. When I was at this magazine, I fell in love with writing about entrepreneurs. That was really my first experience diving into entrepreneurism.

Over the years I would connect specifically with female entrepreneurs. I’m a big believer in equality – that’s something I openly talk about with all of my friends, whether it be income, taxes or negotiating your rate. So, I started chasing down and communicating with a bunch of entrepreneurs and cold-pitching them: Can I write your bio? Can I learn more about your business? 

lindsay tigar history

So that was at the beginning of your career. How did that background play into where you are now?

So as my freelance career grew I started getting introduced to different places, and eventually started writing for a couple of business sites, and eventually for ClearVoice where I’m able to profile my very favorite thing, which is other female writers.

Luckily, because I’ve been doing this for 8 years, I’ve been able to build quite a database of really inspiring women and entrepreneurs who have started amazing brands from nothing and grown them to big household names you would know and love. ClearVoice is one of the places I’m able to amplify their voices and their stories and hopefully inspire a whole new generation of boss ladies who are going to go for it.

Looking for writers who know how to cover the world? Hire vetted travel writers who are part of the ClearVoice Talent Network. Get started now!