#132: Why You Should Do More of What Scares You

All of us are born with a great sense of wonder, courage and boldness.

As toddlers, we have tremendous curiosity. And we’re not afraid to explore and to express our creative spirit.

But somewhere along the way, fear begins to rule our lives.

Fear of looking stupid. Fear of rejection. Fear of criticism. Fear of failing.

We begin to lose our confidence. We stop taking chances. We start playing small.

At times, we may even start to feel like a fraud.

Fortunately, there are many things we can do to turn this tide and regain our confidence. And one of them is to get into the habit of doing more of what scares us.

In this episode, you’ll hear from writer and copywriter Leilani Haywood. Leilani explains how she deliberately does things that scare her in order to grow personally and professionally. And she talks about how this practice has enabled her to launch and grow a thriving freelance business.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about yourself

Leilani Haywood owns Haywood Marketing and Communications, a boutique editorial, social media and copywriting company that serves a diverse group of clients.

How long have you been freelancing?

Leilani started freelancing in journalism school. One of her professors challenged her class to sent query letters to magazines. She sent out ten query letters and landed two assignments.

She’s been writing for local business papers, magazines, and business owners ever since.

What was your day job when you were freelancing on the side?

She started as a newspaper reporter covering politics. Later, she shifted to public relations, then writing scripts for video production. She’s worked as an acquisitions editor for an editorial company and as a writer for an IT division of a university. She also worked as a copywriter for an insurance company.

Every position she’s held opened new doors in freelance writing.

Why did you decide to go out on your own?

At the end of 2008, a combination of circumstances led to her leaving her job. She had daughter with special needs and needed a more flexible schedule. At the time, she had a stressful job as a copywriter for an ad agency.

The ad agency CEO put her through an eight-week boot camp to learn about social media and blogging. It occurred to her that small- and medium-size businesses might want these services at a more affordable price.

At the same time, she was offered a contract with a major financial services firm. She accepted the contract and used it as a way to launch her business.

Doing what scares you has been a key ingredient of your success. Why do you feel it’s important?

Leilani didn’t realize how fearful she was until she started down this path. She was scared to get up in front of a room of strangers and talk about what she does and what she can do for them.

But a friend advised her to do a presentation for a group of business owners. By the end of the presentation, she had ten appointments—and half of those became clients. That presentation group launched the social media side of her business.

Leilani feared that her rate was going to be too high. But whenever she presented her rate, it turned out not to be a big deal. It became her new normal.

She had to get past her fear of networking and talking to people, which required a mindset shift.

To network without fear, you need to shift your mindset from landing clients to building relationships.

She’s no longer afraid to ask lots of questions. Getting project details at the beginning has been really beneficial.

Leilani was fearful of using the phone for prospecting. She created a spreadsheet of prospects and set aside a few hours every week to make calls. She saw prospecting as something that many freelancers neglect, so she was motivated to work on it.

When did you start to realize that it was good to do these scary things?

After Leilani did that first presentation—and it resulted in ten appointments—the benefit of stepping out of her comfort zone was clear.

Do you continue to push beyond your comfort zone?

Recently, Leilani resurrected her newsletter, which scares her! She listens to Ed’s podcast and others for motivation and ideas.

Every week, she tries to spend some time working on her business, not just in her business. Invariably, these activities take her out of her comfort zone.

Often, the real benefit of getting out of your comfort zone is that it stretches your boundaries.

Doing what scares you helps you grow personally and professionally.

What do you hope to accomplish in your business over the next two or three years?

Eventually, Leilani would like to spend more time developing strategy for clients and training their staff to do the work. She would like to land some larger writing projects.

Do you charge by the hour? Or do you price by packages?

Ninety-percent of Leilani’s work is retainer based. Her packages include social media, website copy and a newsletter.

For some assignments, such as e-books, she charge an hourly rate, based on the market.

To come up with these rates, she Googled around to see what people in her area were charging for similar services.

How can listeners learn more about you?

Leilani Haywood on LinkedIn

Leilani Haywood on Twitter