#145: Scared (Uncomfortable, Intimidated) and Doing It Anyway, with Lauree Ostrofsky

Today’s guest is Lauree Ostrofsky, who is a coach and speaker living in the Hudson Valley of New York state. Her business is called Simply Leap. Lauree’s clients are A-students and introverts wanting to feel more confident putting themselves out there in a bigger way, including in their own businesses. 

Lauree has written two books: a happy how-to called “Simply Leap: Seven Lessons on Facing Fear and Enjoying the Crap out of Your Life,” and “I’m scared & doing it anyway,” about reinventing her own life after being diagnosed with a brain tumor at 28. 

When Lauree was in the hospital with a brain tumor, she had an epiphany about how powerful humans are when we set our minds to something. She realized that while she couldn’t control this thing happening to her, humans do have some control over some aspects their lives even in hard times—the words we choose, the people we surround ourselves with. Lauree realized she wanted to help others recognize how powerful they are, so she decided to take a coaching certification program. 

Lauree shares some key messaging that she often discusses with her “A student” coaching clients, such as taking the pressure off yourselves. 

She talks about the need to “collect data” in our business. Don’t create a service or a program first. Collect the data first to see what your potential clients actually want from you. 

She also brainstorms with her clients their ideal work life and their ideal client. 

Societal pressure to be “fearless” can cause us to be unkind to ourselves. It’s OK to recognize that something is new and scary and different—but then find kind ways to help yourself through it. 

Fear is a good indicator that you’re on the right path. If you’re not scared to offer a new package or charge a higher price, it might not be that important. That fear shows that you really want that thing. 

Melanie asks about not having fear—does this mean we are taking the easy route, or being too comfortable? Lauree talks about how the easy route can be good, but we can also create stretch goals for ourselves. 

Lauree (who is a former marketer) and Melanie also talked about how to market our freelance businesses. Lauree says if people have already chosen to work with us, then marketing is already working. “Marketing isn’t this thing over there,” she says. “It’s already happening.” 

She encourages people to make a list of all the things that people thank you for, both in work and non-work situations. Write down their words. Do it for a week or two. You’ll see some of the same things that keep coming up, and some of THAT should go into your marketing. That shows you what the other person thinks about you, and that’s what marketing needs to be. 

For example, if you’re an accountant, you might think your value is related to being good at your job. But everyone might be thanking you for always having a smile on your face and having extended hours—that’s what you need to market. 

Lauree also talks about how we can brainstorm to figure out our ideal clients and what she calls “Jane Goodalling” your potential clients. 

Lauree ends the episode by reiterating that whatever our work is, that it can work for us. It’s OK to be scared. But be sure to seek out people who can help; you don’t have to figure all this out by yourself. 

Biz Bite: Create a “smile file.” 


Lauree’s website: Simply Leap
Lauree’s books
Lauree on Instagram 

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