Making the Leap from School Teacher to Full-Time Food Blogger with Lindsay Ostrom

The Transcript

Making the Leap from School Teacher to Full-Time Food Blogger with Lindsay Ostrom

Jonny Nastor: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at HacktheEntrepreneur.com/Rainmaker.

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: Welcome back to Hack the Entrepreneur. I am so glad you decided to join me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today is a blogger, food enthusiast, and entrepreneur. Along with her husband and business partner, they’ve created Pinch of Yum and Food Blogger Pro. My guest spent the last five years teaching elementary school by day and blogging about food by night. She always went back and forth about becoming a full-time blogger. But in June 2014, she officially made the jump to living this crazy, work-for-yourself-and-talk-about-food-online dream.

Now, let’s hack Lindsay Ostrom.

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Welcome back to Hack the Entrepreneur. Today, we have another brilliant entrepreneur. Lindsay, welcome to the show.

Lindsay Ostrom: Thank you. Thanks for having me.

Jonny Nastor: It’s my pleasure. Lindsay, let’s just jump straight into this.

Lindsay Ostrom: Let’s do it.

Jonny Nastor: Lindsay, as an entrepreneur, can you tell me what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Letting Go of the Scarcity Mentality

Lindsay Ostrom: Right off the bat, you hit me with a hard one. I think one of the biggest things that I’ve done, or that we’ve done, I guess I should say — my husband and I do these businesses together — is letting go of this scarcity mentality. It’s probably true across all different types of blogs and businesses. But with food blogging, it’s gotten increasingly competitive. There are more and more food blogs starting, and people who are rising up as these really, really talented people in the food space online.

It’s really easy to start to be comparative and competitive and to feel like “I’m not as good at this particular thing as so-and-so is.” For me, one of the most important things that I’ve done to be able to move past that tension is to get over this scarcity mindset, that “there’s only so many people,” and holding tightly to this idea that “it has to be me,” or “I have to be the best,” or “I have to have the most followers.” I think when you let go of that it frees you up to do better work.

Jonny Nastor: “Letting go of this scarcity mentality.” You are in, like you said, a very, very competitive space. Would you think that online, in these sorts of markets that you’re in — in a business podcast, I’ve entered a super, super heated space — do you think that maybe competition, as we know it or as we knew it, doesn’t even exist anymore?

Lindsay Ostrom: Can you explain what you mean by that a little bit more?

Jonny Nastor: To me, if somebody is going to read Pinch of Yum, they’re not just going to read Pinch of Yum. They’re going to read probably 20 other food blogs because they’re obsessed with them. People who listen to business podcasts, it’s not like, “Well, I have my favorite. I’m never listening to another one. When Jon comes out with one next year, I’m never going to listen to it.” They’re obsessed with it. People get really into what they’re into. Does that make sense?

Lindsay Ostrom: Yeah, for sure. That’s something we talk about a lot. I think it’s that same idea of, as we always say, “A rising tide lifts all ships.” Just the idea that as we get better, and as people around us get better, the industry as a whole becomes a better place for food bloggers and people who are doing this.

Like you said, the more people that are reading blogs, the more people that are making food and trying new recipes, in one perspective, it can seem like competition from one blog or website to another. It also is a good thing, because it fuels people’s interest in food. Then, they’re more likely to find us, because that’s the resource that we’re providing. I definitely think there’s truth to that.

Jonny Nastor: Excellent. You were a fourth-grade teacher. I believe you spent five years teaching, and on the side — or at night or on weekends — blogging, until you could finally go, just this past year, full-time. You had gone to school. You had gone through the whole process to get a good teaching job. What made you want to veer off of that path and try something else?

Lindsay Ostrom: I think our story with starting Pinch of Yum and building this as a business is so atypical, because it was never started with an intention to make it into a business or make it into something. When I started it, I never ever had the idea that “I’m going to leave my teaching job and do this.” It was like, “I have spare time on the weekends, and I like to cook dinner when I get home from work in the evenings.” It was this natural outpouring or putting on a display of the things that I was passionate about, this creative outlet that served as just a hobby.

I think that we saw the tension build on that as I loved what I was doing with teaching. I still am really passionate about education and really felt like that was meaningful work for me. When the blog started to actually become a thing that was earning money, and it was a business more than just a hobby, that’s when we started to feel this tension of “Okay, what do we really want to be doing?” We see this sky’s-the-limit mentality with the blog, but I also loved what I was doing. It was really hard.

There was probably, I would say, a year and a half to two years of time when the blog income had surpassed the income that I was making teaching, but it was too hard for me to leave teaching. It wasn’t just about the starting of a business, and “I can’t wait to leave teaching and all that.” Honestly, in a million years, I never would have guessed that it would have been here.

I know it’s not for everybody and it doesn’t work that way for everybody, but for us, that’s contributed to this success that we’ve had with the business because it’s this idea of the happiness advantage. I’m doing work I love, and I’m just doing this blog as a hobby. It’s a labor of love. I’m willing to work on it all the time because it feels like a hobby. It doesn’t feel like something that I’m a slave to this thing because I have to be. It was just something I really enjoyed. That was the primary motivation for me working on it for the first three to four years.

Jonny Nastor: “The happiness advantage.” I like that.

Lindsay Ostrom: There’s actually a book that I read that’s called The Happiness Advantage. I can’t remember the author off the top of my head. It’s a really good book. It’s this concept of the importance of investing in your own happiness and doing the things that you love and how positively that correlates with your performance in your work and in your life in general. A really good book. I’d recommend that.

Jonny Nastor: That’s excellent. You never thought that you would do this as a business, yet it’s not luck involved. Did you or your husband have experience in blogging? If not, where did you figure this whole process out?

Lindsay Ostrom: I think a lot of it is just trial and error. That’s actually contributed or been a huge part of why we’ve ended up building the businesses the way we have. When we started, there weren’t a lot of resources available as far as how you can make a food blog into a business.

I think my husband was really interested in that. For him, that was in line with the happiness advantage. He was very interested in that, wanted to learn about that, and had these ideas. But I had the actual platform, the actual blog for him to try these different things out.

Together, we started trying out these things that he was hearing, not necessarily about food blogging. The message we heard pretty clearly about food blogging was, “You can’t make this into your living. This cannot be done.” For him, he’s like, “I don’t know. I think we should try this through trial and error,” and figuring out what’s worked and what hasn’t worked.

Sharing that, then, has really been a huge part of how we’ve built our businesses, and really valuing transparency: “This is what works, and this is what doesn’t.” We know that’s valuable information for people, and we know that’s something that we can anchor our business around.

When we started, for me, I don’t even think I knew what a blog was or like that was a thing. It was really this marriage in more ways than one — because we’re literally married, my husband and I — but this marriage of my excitement about food and my willingness to show up every day and post and developing this platform, and his interest in the strategy side of it in terms of building it as a business. The coming together of both of those was how that process looked.

Jonny Nastor: Excellent. ‘Trial and error’ — you seem to keep mentioning this. As human beings, as entrepreneurs, business owners, bloggers, whatever you want to call it, one of our greatest struggles is the fear of being wrong, making mistakes, and having those errors that could cause our businesses to fail.

Lindsay, can you walk me through how to go through one of these errors in your business and not have it completely side-swipe you so that you can move ahead like you need to?

Accepting the Tension of Being an Online Entrepreneur

Lindsay Ostrom: I think that it’s a really hard thing, but it’s a really important mentality to have. For me, it’s not something I’m naturally good at, like overcoming the self-doubt. That’s not something I’m naturally very good at. I think people have this perception: “If you’re doing this, you must be really confident. You must feel good about every single thing that you do.” That’s really not the case.

For me, the key has been in accepting that tension. Not only accepting that, but saying, “Everything that we do, whether successful in its performance or not successful, everything is moving us forward in some way, even if it’s wrong, even if it’s a mistake, because then we’re learning from that.” We’re able to say, “Hey, look, that really flopped. Next time, this is what I’m going to do differently.” It sounds so overly simplistic: “You just learn from your mistakes!”

I heard a podcast once, I think it was on the Social Media Marketing podcast. It was about building a business and freeing yourself from this idea of making mistakes, and how making mistakes is a good thing. Bjork has this quote framed in his office, and I’m not going to remember who it’s by or anything at the moment. It’s about the idea that the award really goes not to the person who’s doing everything right, but to the person who is in the ring, actually falling down and getting back up every time. Even if you are failing, you’re actually succeeding, because you’re doing something. You’re moving forward, and then you’re learning from that.

For me, that’s a really hard mental shift, because my nature is very self-critical. I’m very much a doubter and a skeptic, but I think that’s super, super important. I feel like as I’ve been in this space more and more, I think that muscle in my brain has gotten stronger.

Jonny Nastor: Yes. I think from talking to so many people, as your husband says, that are in the ring getting knocked down, that it’s literally just a muscle that gets stronger the more you use it. I bet you if you thought about things that happened to you just in a given week in your business, like little failures and stumbles here and there that probably would have been so devastating three or four or five years ago, just to get over mentally, it gets easier. It really does. That’s smart. I like that.

It’s great that you have a team. There is literally such an awesome team that I’m sure if one person gets knocked down, the other one could be like, “It’s all right. Let’s just keep going. It’s cool. We’ve got this.”

Lindsay Ostrom: I think that’s a huge piece of that, being able to see a wrong as actually a good thing, or a fail as a positive and something you can learn from. I feel like part of it is just knowing yourself. For me, I know about myself that I’m not very good at that by myself. I always do better when I can talk to somebody about that or when I can process that somehow. It’s like, “Okay, just give me 10 minutes to talk about it, and then I feel better.”

The interesting thing is for Bjork, he’s the opposite. He’s like, “I don’t really want to talk about it. I just need to think about this for a while, and just be on my own,” which works out really great in a marriage. It’s just really good to know yourself and your strengths and weaknesses and how you process through stuff like that because you’re going to have to process through it. Figuring out what those things are and how you can do it to make those muscles stronger is really important. For me, it’s talking to people. That’s why it’s really great to have a team.

Jonny Nastor: Excellent. Let’s talk projects, if we can. ‘Projects’ is a loose term that can mean any sort of new thing you decide to take on in your business. Whether it’s moving from Pinch of Yum to also Food Blogger Pro, or writing some new ebooks, or as you said prior to the call, starting a new podcast. What’s the process you guys go through, at this point, to determine what a new project is that you guys should go all into and focus on?

The Importance of Setting Timelines and Goals in Your Business

Lindsay Ostrom: That’s a really good question. Right now, my husband and I together run both businesses. I manage Pinch of Yum, the day-to-day. He manages Food Blogger Pro day-to-day. Our process is very flexible. I wouldn’t say we have a really strong process at this point. But if we did, what it would look like, our usual, would be sitting down, having a meeting, probably once a month, and saying, “Here are the big things that we have on our minds.” It’s taking the big ideas, whether it would be for the next year or the next five years, getting all the ideas on an agenda, and then working through them with a timeline approach.

That’s what we did at our most recent meeting a couple of days ago. We took all these big ideas and laid them out. Literally, I just took a big piece of chart paper and drew out a timeline. Then, we said, “Where does it make sense for each of these things, and/or does it make sense at all?” Because one of the things that you can learn really quickly, and I’ve definitely learned as an entrepreneur, is that you’re just drowning in opportunity.

There’s an idea around every corner, and you have all these different great plans, and these great new things that you want to do. But it can become an analysis paralysis where you never actually take action on any of it, because you’re just thinking about all the ideas. We’ve really struggled with that a lot. I think this timeline approach is really helpful to us.

When we plot out, we take the most important pillar things that we feel are in line with our business and our goals for each of the businesses and then plot those out on a timeline and then say, “We actually don’t have time for this kind of side project, and/or it doesn’t align with where we’re going with this stuff.” That’s how we take the really high-level ideas and get them on the map.

From there, there’s a whole bunch of different project management stuff that we do. Bjork and I, like I said, we’re really different. We manage projects in different ways. In terms of us together brainstorming the big things, that’s our process at this point in many ways.

Jonny Nastor: “Drowning in opportunity,” which is absolutely true. It’s funny. Before people get started, it’s always “What should I do? What should I start? Where’s the ideas come from?” As your business grows, the opportunities literally fill your inbox and fill everything that you possibly do.

Lindsay Ostrom: I think even if it’s not opportunities from other people, it’s opportunities for your own to choose yourself to do this next project. It’s like, “We want to do this video thing. We want to do this podcast. We want to add this thing to the blog and have this branch of the business.” We drown ourselves in opportunity with all the different ideas that we can start to have.

I wasn’t that way to begin with. I’ve always seen Bjork as more of the idea guy and having all the ideas. I think now, the longer I’m in it, the more I feel that, and the more I feel, “Whoa, there’s so much stuff.” There’s so many things we want to do. Bjork and I recently read the book, Essentialism, which was a really good thing for us to read. It’s about saying ‘no’ to most things to be able to really hone in on what are the big things that are most important for your business and just for your life in general.

Jonny Nastor: I agree. Essentialism is an amazing book.

We’re going to end off on something I call ‘the entrepreneurial gap.’ You have transformed your life and your husband’s life from having that regular job to literally living a dream lifestyle, whether you think so or not. It’s an enviable position that you are in. You’ve got to spend a year in the Philippines teaching in an orphanage and doing amazing things. Right?

But the entrepreneurial gap is something that we, in our businesses and people with dreams and ambitions, we’re always looking ahead. We’re always setting goals one month, three months, six months, one year, five years down the path. When we hit those goals or even before we hit those goals, we set new loftier ones further into the future. But we don’t stop, turn around, and look at where we’ve come, what we’ve done, what we’ve accomplished.

Lindsay, could you please take this time right now for me and stop, turn around, and look at what you have accomplished and tell me how you feel about that?

Lindsay Ostrom: That’s a really cool question. I’ve never been asked a question like that before. That’s so great.

I feel really proud of it. I feel really proud of myself, because I didn’t start out with any interest or skills in the entrepreneurial realm. I think I’ve grown into this love of developing my brand and my business. I’ve learned a lot of things along the way. I feel really empowered to think that I did this. Obviously, we did it. My husband and I did it. That’s always been a passion for him, and it hasn’t always been a thing for me.

When I look back and see, “You built this. You’re now working from home doing this work that you love because of this.” It’s really surreal. It makes me feel empowered, honestly, when I think about it. I think, “If I can do this?” And if you’re listening, and you’re thinking some of these same thoughts — I never started out thinking of myself as an entrepreneur. Never. I was a teacher, and I love cooking, and all of that.

There’s so much that you can do as you lean into your passions and make that into something that you have a platform for. You can develop an audience, and whatever way that might look for you. I guess the message I would want to say is, “This is doable. If I can do this, this is so doable.” I feel really proud of myself for having come this far. That’s a really cool question. Thank you for asking that.

Jonny Nastor: Thanks for answering it like that. That was awesome. You should be really proud, because it’s enviable, and it’s really, truly awesome and impressive. Lindsay, we got to talk about you and your businesses in passing. Can you now lead the listener by telling them specifically where they can find out more about you?

Lindsay Ostrom: My blog is Pinch of Yum at PinchofYum.com. We have also a membership website that’s for food bloggers or people who want to start a food blog, and that’s FoodBloggerPro.com. On social media, my favorite social media outlets are Instagram and I’m @PinchofYum there. I’m also recently on Snaphat, which I feel cool about. That’s my handle there. I don’t even know if you call it a handle. That’s how new I am to Snapchat, but it’s ‘pinchofyum.’ And then all my other social channels are also PinchofYum. Wow, total dork moment.

Jonny Nastor: Very cool. I will link to your sites and your Instagram and stuff on the show notes, so everyone can track you down. Thank you for sharing with us today. Lindsay, thank you again so much for taking the time. Please keep doing what you’re doing, because it truly is awesome.

Lindsay Ostrom: Thank you so much, Jon. I really appreciate it.

Jonny Nastor: Lindsay, thank you so much. I appreciate you joining me. I appreciate your story and just your sincerity in what you’re doing. It was really, really fun to talk to you.

Lindsay has gone from teacher, this job that people spend a lot of time on. You go to school, get an education, and become a teacher. It’s typically not something you then move from to become a full-time blogger. I love it. It’s a brilliant story. To me, that just encompasses the power of the Internet and the way it changes people’s lives when they decide to step up and do it. I really love the story. It’s great, Lindsay.

Lindsay said a lot of smart things during our conversation. We spent about 24 minutes talking. There was a lot of stuff said and a lot of smart things. She really hit on a lot of really, really smart points. But she said one thing, didn’t she? She did. She said that one thing that really, really stuck out. Did you get it? Did you hear it? Let’s do it. Let’s find the hack.

Lindsay Ostrom: I think people have this perception that, “If you’re doing this, you must be really confident. You must feel good about every single thing that you do.” That’s really not the case.

I think the key has been in accepting that tension. Not only accepting that, but saying “Everything that we do, whether successful in its performance or not successful, everything is moving us forward.”

Jonny Nastor: And that’s the hack.

Lindsay, yes, thank you. It’s so true. It’s this weird perception people have of entrepreneurs, that we are super-confident people that can deal with all this stuff. We never second-guess ourselves. We never question our decisions. Yet internally, we just struggle with it all the time.

There’s this tension that’s always there that you need to learn to deal with. We’ve talked about this lots of times, but it’s so essential. This is the mindset of the entrepreneur. This is the only thing that makes us an entrepreneur, more so than a person who has yet to take that leap. We’ve learned to deal with it in our heads, this constant tension. We’ve learned to make it look like from the outside that we’re super-confident, but we’re typically not.

We don’t know what we’re doing. We’re making it up as we go. We’re willing to fail. We’re willing to screw up. We’re willing to embarrass ourselves. Yet somehow, we don’t care, although we do. It just seems like we don’t care, because when we do, we just get knocked over, and we get back up, and we do it again. It’s just the way it works. Honestly, we don’t know what we’re doing. Trust me, we don’t. We know after we do it. We don’t know while we’re doing it. We don’t know before we’re doing it. It’s just the way it is. It’s just key.

I’m glad Lindsay brought that up, because we don’t have this confidence that someone might think we do. It’s just the dealing with the tension.

Thank you Lindsay, so much, because talking to you, it sounds like you’re uber-confident, like you know what you’re doing. You know what your next steps are. I appreciate that you admit that there’s this internal struggle all the time. It’s not just you. It’s not just me. It’s all of us. We all deal with it. It’s being human and creating things that put us out there and put us out in front of people. That exposure is always going to cause that tension. You’ve just got to deal with it.

It’s fun. It really is. It sucks at times. It keeps you up at night. Sometimes, it wakes you up early in the morning, but it’s fun. What else have we got to do? Thank you so much, Lindsay.

This is fun. This is always fun. Why is this always so much fun? I don’t know. I’m so glad you’re out there. I honestly am. Stop by the website HacktheEntrepreneur.com if you haven’t yet. Even if you have, we’re always sending out updates. It’s a great place to be over there. You’ll get all my newsletters, if you would like. Come on, it’s great. Every Sunday afternoon, I’m sending out my work. Either way, I really appreciate you listening to the show, and I know there’s so many podcasts out there. It’s mind-blowing right now. It means so much that you are there listening to me and my guests talk about things that get us excited and fired up.

Thank you again, and have yourself a great day. Until next time, please keep hacking the entrepreneur.