Pushing the boundaries of your earning potential - #IMadeTheAsk with Kristin Wong

Welcome to the #IMadeTheAsk entrepreneur spotlight series, where we share the stories of entrepreneurs and small business owners who have made the ask...and lived to tell the tale.

Read on to learn about Kristin's business journey, how she succeeded at tripling her freelance income, and why finding the courage to make the ask isn't just about your own business.

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Tell us a bit about yourself, and your journey as an entrepreneur.

I'm a freelance writer, journalist, and author of Get Money: Live the Life You Want, Not Just the Life You Can Afford. I regularly write for the New York Times, New York magazine's The Cut, and Lifehacker. I moved to Los Angeles in 2010 to pursue a writing career, fully expecting to be the stereotypical starving artist. For a while, I did fit this stereotype: I earned next to nothing for my writing, and eventually came to expect this as normal. One year, I decided to start asking for more money. It was a simple experiment to see how far I could push the boundaries of my earning potential. Asking changed everything. In just a couple of years, I tripled my freelance income. I started making more money than I ever had in my life. Forcing myself to make the ask played a huge part in that.


What's an Ask that you chickened out of making...and regret?

Recently, I started working for a new client who paid more than I've ever been paid. After tossing out their rate, they asked, "does that work for you?" It was the perfect opportunity for me to say, "Actually, would a rate of X work for you?" But I was so impressed with the rate they tossed out, that I immediately said, "Yes! That's great! Of course!" and immediately regretted it. It's still a good rate, and my girlfriends all agreed that they would have done the same thing. But I feel like a truly smart negotiator would have forced themselves to ask anyway. I think that's how you REALLY get to the next level with your professional value: always ask. I think this is especially true for creative workers and women, who have a tendency to undervalue themselves.


What's the Ask that you're most proud of making - whether or not it worked out.

The first time I worked with a major media outlet, I was so excited to get the gig, I honestly would have done the work for free. (Not good!) So when they suggested a rate that was below my usual, I was only a little bit disappointed. I was worried about asking them for more money, because I didn't want to risk losing the gig, but I did it anyway. And they said no. But it was the most liberating experience, ever, because I had done everything I could to push the limit of my earning potential with that client. I had asked. And, of course, I didn't lose the gig. It doesn't hurt to ask!

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Which Ask has been the biggest win for you - professionally or personally?

I once asked a regular client for a rate that was almost twice what I was making. They immediately said yes and it increased my monthly income quite a bit. While this was a big win, it also made me realize how long and how much I'd been underpaid.


What's your #1 piece of advice for other entrepreneurs or business owners who are gearing up to #maketheask?

Remember: by making the ask, you're making it easier for others to make the ask, too. This is especially true for women, who are perceived differently than men when they speak up for themselves and negotiate. So if you're a woman asking for a raise or asking for a higher rate or salary, you're making it more common for women to speak up and advocate for themselves.