#164 – Facing Your Entrepreneurial Fears with Lauree Ostrofsky

Click on the button below to listen to this episode of the Start Fierce Business Podcast.

Lauree Ostrofsky founder of Simple Leap has a background in tech PR, helping open source startups break through the noise.

For the last 11 years, she’s been an author, speaker, and coach with Simply Leap helping A students — the hard workers and dependable friends among us — leap into fulfilling work. Many of them are entrepreneurs and facing the fear of going out on their own, of searching for the “right” choice, and of potentially disappointing people they respect by following their heart.

In this podcast episode, we discuss doing things in business even though we’re afraid to do them. We also talk about finding support for the things we’re doing so people don’t project their fears on us.

Basically owning a business is just doing research constantly. - Lauree Ostrofsky Click To Tweet

In This Episode of the Start Fierce Business Podcast:

  • Lauree shares her entrepreneur origin story.
  • We talk about doing things afraid in business.
  • We also discuss why she’d like to have lunch with Warren Buffet.
  • As well as how to figure out where to get the support for the scary things happening in your life without allowing people to project their fears onto you.

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Note: Transcripts are created automatically and are not 100% accurate. However, they help our visitors find relevant content using our website’s search feature.

Welcome to the show. Lauree. Thank you tell me about yourself outside of your business. Yeah, so I am when it when people look at my business card, it is an author, speaker, coach and hugger. So I would say outside of my business, I go on HUD tours where I announced on social media where I’m going to be and walking around a city or a town that I’m in, and if I’m near you, and near your office, I’m happy to stop in and give you a hug. And I don’t necessarily hug strangers as much as I hug people I care about encourage other people to show the people in their lives, how they feel and hug like a minute. So I have like a hug all on my website and I post about them all the time. But that really isn’t isn’t my business but I feel like it’s such a great message and and something I feel really passionate about. So that’s that’s who I am.

Okay, well, tell me about your business and how you got started with that? Yeah, sure. So I have been a coach now for nearly 12 years. And I the origin story of how I got into was I was climbing the corporate ladder in my 20s and being very diligent, making my parents proud. And I was doing everything right. I worked in Manhattan at a marketing firm and had a fiance and my apartment and you know, all that stuff was feeling like it wasn’t it wasn’t really what I was meant to be doing. But I didn’t know what to do next.

And I spent a weekend like trying to figure it out and say, and, and basically looking at my saving the cow and wondering how long could I go out on my own and kind of figure something out before I needed to go back and get another job figured everything out over the weekend showed up on Monday morning.

To have a meeting with my boss, but I had a doctor’s appointment that morning first because I had this ear infection that I gotten on a business trip. And luckily I had the meetings in those order because I was meeting with the doctor and it was not an ear infection. It was actually a brain tumor. So I was diagnosed with a brain tumor at 87 and had a bunch of surgeries and my life took a very different path. But in the process of the brain tumor and surgeries and being in the hospital bed. That was the moment actually I decided I was going to coach and I was going to decide decided that based on my experience of how much control we still have, how much power we still have, even in moments that feel out of our control, like like a brain tumor, like being in the hospital, like divorce, like losing a job, you know, there are these big moments in our lives.

And even though we feel powerless, there was a lot of power that I found in that moment. And I realized if I can help other people recognize the power they still have in every moment of their life, that that would probably be like the best job ever. So that is the moment I became a coach and I got a year long certification and really started from there. And then kind of added speaking and, and being an author kind of to that over the years. So was that the moment that you knew you were an entrepreneur? Or was that something you realized before you had your job? You know, I don’t know if this is true for your listeners. But I feel like I knew I was an entrepreneur, it got it’s easier to say when I look back like the moments even kind of from childhood where I would like think about how he would do it my own way or I didn’t want to do something just because everybody else was doing it. But really the I would say the moment that I was an entrepreneur was was after my surgeries. I was still going through my coaching certification. And instead of going back to my day job, I actually started consulting with a virtual PR agency. So there are five of us who worked virtual and we kind of build clients as a business. But one of us was kind of like the main client person and kind of paid all of us as consultants. And so that was the moment where I realized what an entrepreneur meant because I was working from home I had to set my own hours I had to pay quarterly taxes and like what that meant and I feel like that was such a really interesting education for me of what like the entrepreneur life like Oh, I can’t leave the TV on during the day because like, I can’t get anything done. Like I I needed to learn some really important things that then led to me like really owning and running a business later and what’s been your greatest challenge as an entrepreneur I would say it’s pretty similar to the clients that I Serve n. And that is worrying about quote unquote, quote getting it right like making the right next choice or when I put out a new service or product, like if it’s the right one, or if I’m doing the right thing worth I could and what’s the flip side of that I could get it wrong. And I think that like black and white thinking can really get in our way from actually trial and error, which is all research. Basically owning a business is just doing research constantly. Okay, so that didn’t work or that’s what people responded to. So I would say, like, kind of just reminding myself about research, and then it can be so much lighter than it is, is it’s one of the things that I keep going back to. Yeah, it’s all the tests none of us really know what we’re doing.

That’s right. Yeah. And we will it’s out there and people responded to it and we you know her you know, have feedback so, and you can always do it again Yeah.

What works for one person? You might read about it, and it really worked well for someone, it might not work for you. You have a different audience and your audience doesn’t resonate well with it. Or you might not be good at blogging. Maybe you’re better at talking. Or maybe you’re better at doing videos. Yeah, you’re absolutely right. Yeah. Like, and you, you have to be true to you. So we connected on Twitter over the topic of fear and how it holds people back from all types of things. Can you talk more about that? Yeah, sure. So, um, yeah, fear is so it’s so interesting because it hides in thing and it hides you know what I’ve already mentioned? Like the get it right, or I have to get it right. Or what if I get it wrong? Or what if I disappoint someone people that I respect and care about, like my friends and family? Like what if they’re disappointed or surprised or shocked or something, you know, so there’s this Like fear can, like, lurk and hide in these things that we tell ourselves or that we worry about what. And, and really, I think I think one of the things that was kind of like, not wrong, but like a problem with social media is that like this stuff around being fearless, and there’s just so many means and things about how we need to be fearless. And the truth is, I don’t think we can ever get rid of fear. I think that fear is part of our lives. And there are so many authors and things that have said that it’s like, so it’s actually our relationship here that needs to change, we need to be like you. So one of the things I say to myself in the middle of the night when I worrying is that oh, this is what’s happening. This is when I usually worry Okay, so this is normal. Like I know tell myself that at 3am so I can get back to sleep as opposed to Oh my God, I’m afraid what am I going to do about it, like not being afraid of fear, but like acknowledging it as normal and helps it helps the relationship with it change Yeah, I love that because I know for a live People, even for myself, it’s been something that has been a hurdle, but I’ve learned to do think frayed.

When I was a freelancer, and then I went back and well, I got like a freelance gig. That was like, long term that turned into a job. And then I got used to the income. And when I became co founder in my startup, and it was time for me to go full time with my startup. It was my last day at the office. And I, I was crying because I was afraid like, well, I had reason to be afraid, right? Because my, my salary was only guaranteed for six months. And here I am a year and a half later and still going so awesome. Congratulations through that. Yeah, I did it afraid I could have just been like, let me just do this part time but I was like, No, I have to do it. And I didn’t tell anyone. I did not tell my friends or my family that.

That I only had six months of guaranteed salary. Oh my god, you did it. Right. Because, you know, I, I talked about that in both of my books. Like, you have to think about the people that you’re surrounding and like, what they can handle and what you can handle back from them, right? Like, there are people who love you and support you, but like they’re afraid and you do not want to take on their fear. So, like, you need to talk to them when you’re ready to handle whatever it is that they’re going to say. And that means surrounding yourself with people in the meantime, who can handle it like that doesn’t mean that you don’t love people in your life. And actually, just me like, you know, things are sensitive, like, especially early on in the startup it’s like you’re sensitive like this is still new like and treat it that way. treat it with that kind of tenderness and yourself with that same kind of kindness. Yeah, I didn’t even tell anyone until like after the six months passed and the crazy or part was that my daughter was hold and then she for high school she wanted to go public high school so I was like, wow, I have to move to a better school district. So two months in, I moved and I definitely, but the right if I didn’t have a salary, so I did that. And when I signed the lease, I was like, but I’m still here. But I had to do it. Afraid It was so scary, but it’s like you said, like, I had to be aware of the people that were in my life. And I had to realize that they were gonna put their fears on me. And I didn’t want that because I was already afraid enough. Yeah, yeah. Yeah, you don’t need Yeah, yeah. And and, and so you say, do it afraid and, you know, my first book is I’m scared and doing it anyway, because it’s true. It’s like you can be afraid and you can keep going. Like those two things can be true at the same time. And it’s actually really liberating to realize that because I think there’s so Many of us who have made really safe choices like when we’re younger, and you know, out of out of fear or out of that we’ve made safe choices in the past. And when you start making choices that push you out of your comfort zone course you’re going to be afraid you’re actually it would actually be wrong to assume that you’re going to be fine. Doing was an entrepreneur pretty much everything is scary because everything is new territory. Yeah, and just a disclaimer, if people that are listening, I am not telling you to quit your job. I I was freelancing for years I have really good contacts with people that I know I could have gone back to backup plan. I could have broken my lease and moved in with my parents like so there were things that I could have done that wouldn’t have been comfortable so I wasn’t like all the way crazy so yeah, don’t quit your job today. And you’re not prepared just because you heard my story so i’ll i’ll ditto what you just said.

Because I built my coaching business on the side for nearly five years while I was consulting with that virtual company I was talking about and like, I really did build it before I jumped completely. And so I’m right there with you. Like, there are a lot of people who are like, totally going for it and like, okay, you know that, you know, as long as you think about your cushion first. And But yeah, I mean, it’s also you can also be smart and be successful, building it over time and being really methodical about it. Yeah, exactly. So aside from not wanting to work for someone else, and aside from your family, what’s your why I think similar what I was saying about being in the hospital bed, like when I realized that no matter what is happening in our lives, that we still have real choices. And I think you Cindy, you were just telling a really great story about yourself and about your daughter and kind of what was happening in your world like things happen in our lives and No matter what is happening, we have a choice. What we tell ourselves about what’s happening, like the words that we use, what we, what we tell ourselves, an article about it, how we feel about it, what we do about it, and the people we surround ourselves with. So there’s like a lot of power that we still have, even if stuff is happening around us. And I think that that propels me forward. Actually, every time I say those words, it propels me forward to say, and I feel like I’m doing the right thing because I’m I’m empowering people. And that feels like a really strong lie. If you could have lunch with one business thought leader, who would it be it’s a toss up so I think my first answer was Warren Buffett because he seems well i don’t know i don’t think i have to have a why for that because it’s a warren buffett and and my second one is um. is Denise are spelled Thomas Lucky Bitch. If you guys know her. She’s Australian, I believe and she does a lot.

My mindset for women entrepreneurs stuff and I really I like listening to all of her blog posts and stuff like that. And I feel like she’s. And this is probably true for a lot of podcasts, there’s a bloggers and stuff like you seem really outgoing, but then most of us are introverts because we’re writing and producing at home. So I would want to have lunch with her, because she has really interesting things today. And I say, and I think she’s also an introvert at heart. And so that would be cool to have lunch with, you know, it’s so funny. I work in a co working space and they’re always bringing in people to do talks and and sometimes we have to do pitches in front of investors for competitions and stuff, right. And one time my business partners, one of my business partners saw me present our, our pitch deck just to one person and he’s like, you know it really well you should do it for the competition. I was like, No. Are you crazy? He’s like, Yeah, but you haven’t.

Your podcast and you talk to people all the time. Yeah, I’m at home staring at the wall or, you know, looking at cello like, and it’s only one person. It’s I’m not talking to a room full of people. Even though people are listening. I focus on my conversation with the person. I don’t think about the audience and I can’t do that in front of her. You’re totally right. Yeah, is a very different thing. Yeah, you get there, you’ll get there because I never saw myself as her. And I finally got to the point where it was, I knew what I wanted to say. And I knew the that like I felt so passionately about the thing that I wanted to say that I got through the fear of saying it in front of other people. That said, the first speech I gave actually hid in the women’s restroom right up until the point I was going on stage because I thought it might throw up and I figured why I was hiding in the restroom. Thinking Okay, just in case I throw up, I’ll be here and if not, I’ll just practice My speech for the whole time until the moment I have to go up so you know you can do doing it scared a scared and doing it anyway yet again you know when you’re ready go for it the first and only time I spoke in front of people were like you know in school I spoke in front of people but as an adult my friend invited me to this event and it was with young girls and I had to speak in front of people and I felt fine except like a few days before my face like breaks out in this style. And that’s when I found out that I had psoriasis and I haven’t gotten it since. Wow. Wow. Yeah, I couldn’t even hide it with makeup. So that was bad.

Wow. But I guess I’ve never I haven’t been that stress. Mm hmm. By that our bodies are so interesting. What happens, right? Like, oh my gosh, yeah. If we don’t listen, it gets louder. So So after that.

I was like, Yeah, I can’t talk. I’m not gonna do that again. And you found a way around it with this great podcast. So Exactly. Are you? Yeah. Um, what’s your favorite business book? And one I go back to often with clients is Strengths Finder, 2.0, I think it is. But it’s it’s also a lot online personality survey. And I love surveys. And so this survey was developed by the Gallup organization to use within, within businesses, but it also works I use it with clients often and it basically goes by the premise if you’re, if you don’t know about it, it goes by the premise that instead of you know, when we’re reviewed at work, instead of focusing on our weaknesses instead, what if we focused on our strengths and and our strengths really are things that we take for granted because it’s just how our mind works and just how we do things and always done them but it actually when when look From the outside, they’re actually things that that we take for granted that other people really value and like us for and would pay us for. And so kind of identifying those really helps shape the kind of careers that we take on and the kind of businesses that we build and the roles that we take within them, which, so I really like using it as a tool for myself, and for people I work with. Now, what’s your favorite internet resource or app that just makes life easier? Oh, my gosh, when someone told me about mile IQ, and it totally changed things. So mile IQ is is an app for doing your mileage, but it’s always on on your phones. You don’t have to remember to turn it on or whatever. And then you can just file things away as a business expense or or as a personal one. So it’s just made any kind of driving and and doing that kind of those kinds of expenses for my taxes so much easier. I think I just do that in in QuickBooks. Yep. Just Yeah probably kills my battery. Yeah exactly. Just plug in your phone while you’re driving. It’s all good right? You know and this is the first year that I have been using it instead of like manually jotting down my miles and I already have way more miles on it than I did last year and the whole year so I know I didn’t track everything last year yeah you’re totally right yeah and the the fact that it can just happen and not worry about it. Oh my gosh. such a relief where can listeners find you online? What are your social media handles? what’s your website? Yeah, so everything is is the same so I am simply leap on my website. Simply leap calm. My my books and workshops and stuff are all on that website and on social media. I’m pretty active on Instagram, Facebook, and Twitter. And all of those handles are simply bleep as well. Alright Lauree, thanks so much for sharing your story with us. today. No, it was a pleasure. Thank you, Cindy.