An Interview With Lauren Holliday

A College Dropout Making Six Figures

This past week I had the pleasure of spending 30 minutes talking with renowned freelance writer and founder of Freelanship, a full-stack marketplace.

A Little Backstory

Lauren went to college for Journalism, and yet had hopes to start a club — I know, there’s a clear disconnect here!

She realized in 2012 that college simply wasn’t for her, and decided the only way to get what she wanted out of life was to go into business for herself. Rather than starting a club, she decided to pitch Freelanship to Y Combinator, a seed company for business startups.

And from there, we begin our interview!

1. Lauren, what was the worst moment in your entrepreneurial life?

When my co-founder gave up on Freelanship. At the time, it seemed like the worst moment of my life. I realized that it’s probably my fault. I put a lot of pressure on him and tried moving too fast.

2. Looking back on it now, what did you learn from that experience?

I learned that I need to stop trying to find the “perfect team” and just get things done myself. I also learned that I can’t count on anyone or anything to work as hard as I do, and that’s a lesson I’m still learning today. I love working with teams, but it doesn’t always work out that way.

3. What was a big “AH-HA!” moment for you? When did it click that this entrepreneurship/freelance thing might be right for you?

I’ve really always been a salesy, go-getter kind of person. Even as a child, I always pushed to be number one in my class for things like raffle ticket sales. I guess it really clicked when I realized I couldn’t take being micromanaged for the rest of my life. I love building things and taking on challenging projects, which is probably why traditional employment didn’t interest me.

4. What are one or two personal habits you feel contribute the most to your success?

I’d say perseverance and an obsessive focus on specific things. Besides that, I read somewhere that you should physically move to three separate places and get one major task done at each place, and I implement that idea in my life pretty often.

Pro Tip: FOCUS stands for “Follow One Course Until Successful” and is a common theme among every successful person.

5. What’s the best piece of advice you’ve ever gotten?

I’ve got three. Adopt a can’t count on anything mindset. Use good judgment. Send a lot of emails.

Oh, and a quote from John Wooden regarding my “Can’t count on anything” mindest:

“You can lose when you outscore somebody in a game, and you can win when you’re outscored.”

6. What is one book you would recommend everyone reads? Why?

For anyone in their 20’s, I highly recommend The Defining Decade. I’ve read that book several times and it really motivates me to get my ass in gear every time. It talks about how what you accomplish in your 20’s, from your finances to your relationship, sets the stage for the rest of your life.

I also highly recommend How to Win Friends and Influence People by Dale Carnegie.

See below for the author of The Defining Moment, Meg Jay’s TED.

7. Can you give one parting piece of guidance to anyone who may be reading this?

As my dad told me, “Do what you love and the money will follow.”

So many people just want to make money and do things fast. I understand — in freelancing you have to take on clients and works you don’t love, but you work your way to something you love. As long as you’re on the path to get there, you’re doing good. Not taking a chance and not trying is a big mistake.

8. Lauren, thanks for taking the time to talk with us. What are some ways the readers might be able to get in touch with you?

Obviously, you can find me at freelanship.com. I also run a website called hackthejobhunt.com. Finally, follow me on Twitter and Medium.