Tonka Talk Community and Connection

Imposter Syndrome: Ask Kelly!

• Natalie Webster

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Are you wrestling with feelings of being a fraud or fake in your career? Here's an episode you don't want to miss. We explore the phenomenon of imposter syndrome with Kelly Olsen, a local entrepreneur who shares personal experiences and advice on handling this challenge. 

Kelly emphasizes the importance of humility, asking for help, and retaining a childlike curiosity. This conversation is a treasure trove of advice for anyone grappling with this pervasive issue.

Email your questions about entrepreneurship to Natalie@tonkatalk.com and each Monday Kelly Olsen will answer them on Monday's Ask Kelly! 

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Speaker 1:

Hello, I'm Natalie Webster and this is Tonka Doc, where we talk about community and connection and on Mondays Kelly Olson joins us and we do our segment. We like to call Ask Kelly. Kelly Olson, if you don't know, is a local entrepreneur here in the Twin Cities. She's done multiple projects. You'll learn more about that as we go along but we thought we would do this as an opportunity for our community to reach out. If you have an idea, you have a business idea, or you have aspirations to be an entrepreneur but you don't know where to start. Maybe you're struggling with something and getting something going in the community business, nonprofit, whatever it is you can go ahead and email in at natalie at tonkacom and just put in the subject Ask Kelly, ask all your questions and on Mondays Kelly Olson is going to address them.

Speaker 2:

You're making me feel like peppermint patty on peanuts, with a little advice two cents, that's right.

Speaker 1:

Or what it's worth. That's right, I have to switch my glasses, okay. So today, our first question which I think is very interesting and I wouldn't be surprised if a lot of you can relate to this it's how do I overcome imposter syndrome? But if you're not familiar, imposter syndrome is just that. It's that feeling sometimes we get when you're doing a job and you're even good at your job and it's going along, but you just get this feeling of like I'm a fraud, I'm a fake, even though you're not Unlike that, like Tinder swindler or something like that. I believe those people never have imposter syndrome. No, they really don't.

Speaker 2:

Actually, this is a really great question because I think we all feel that at times. But what I thought was really interesting my mother-in-law was the CEO of Great Clips for many, many years and it was probably two weeks before she was about to retire. She said oh my gosh, I might actually make it to retirement before people figure out that I don't know what I'm doing. Wow, I just think it's something that stays with most of us throughout our career. But I actually think certainly you want to feel confident in what you're doing, but I think it's actually healthy to feel like, hey, I don't know everything here, and it keeps you a little bit humble and willing, I hope, to ask for advice where it's needed.

Speaker 1:

When you run into that, and it's so interesting to me that somebody like your mother-in-law, who held such an amazing position over a humongous company even she experienced that, and it sounds like she experienced it up until the end of her career when she retired.

Speaker 2:

In fact she probably would have me correct you on the retirement phrase. She calls this her performant. She's going to do what she prefers now.

Speaker 1:

I like that. I want to get to my performant yes.

Speaker 2:

I feel like I'm already there.

Speaker 1:

True, I feel like if we do get to do some really fun things, or I should say we create some really fun projects and things and bring people into it, do you, when you run into that and have those moments where it's that imposter syndrome, is there anything for you? How do you pull yourself out of that?

Speaker 2:

Gosh, you know what one thing I Think. I'm pretty upfront about the fact that you know a lot of these things I've never done before. Yeah so I don't feel like I'm standing behind a wall of where people really have an expectation that I'm gonna have every answer Sure, so I think that that really lessens the burden.

Speaker 1:

I'm not.

Speaker 2:

I'm not out there saying I'm the expert in everything.

Speaker 1:

That's a really good point and that's really true, and that's it. We kind of talked about that last time too the willingness to be able to ask for help and say, hey, I'm not totally sure how to do this, I want to do this, and I find it really interesting and that's why I think you're the perfect person for this segment, because you have done so many things for the first time, things that you just never thought you were we be doing, being where you were in real estate before and then you bought a bakery and, and just from there, these different things. You've executive produced a show that got nominated for a regional Emmy I mean, it's just first thing up Developing a hotel on Lake Minnetonka things that you've not done before.

Speaker 2:

I ran a gymnastics gym in my 20s.

Speaker 1:

Yeah, we're in a gym, yeah do you find that each of these experiences because it's something you've not done Do you feel that it kind of helps a little bit with that those those feelings we get when we fill imposter syndrome because you know like Okay, I've not, we have to enter into this unknown any time we do anything and, as we know, it's that unknown area where it can be very uncomfortable and it's easy to default to Nope, I'm just gonna stay here in my box because I know that and those feelings are comfortable. But what I see you do a lot is you go outside of that and I feel like that's like kind of where you live. Do you think it's because you've done these different things Multiple times and and have been fairly successful at it?

Speaker 2:

Um, I really think, as a kid, you really you don't know anything yet, right?

Speaker 2:

Yeah you're trying everything for the first time and you're asking a lot of questions and then the feedback that you get most of the time you just accept it, right, yeah. So I think if you can hang on to that sort of childlike curiosity, hang on to a little bit of the creativity that's sort of innate to us when we're children, and you can just push that forward, I don't feel like there was ever this finish line where I felt like, oh, now I've graduated and I should know everything. Oh, now I've done this and now I should know everything.

Speaker 2:

It just feels like a continuation of that and maybe that's why I still love to play so much, because yeah.

Speaker 1:

I'm trying to hold on to it. Yeah, I think so, and that's a really good point, maintaining your curiosity, even, I think, in Coming up against if there's any opposition, because sometimes we have ideas and some people can't handle those ideas.

Speaker 2:

That has never happened to me. Never, not one time.

Speaker 1:

I'm sure no one's ever gone. Well, no, you can't do that, but you're right having that. Even then, if you approach that with curiosity, you're like, okay, well, tell me more about that and I've heard you say this a lot, I've seen her in situations and she'll just tell the person okay, tell me more about that. You can tell you're trying to understand it. You don't try to, you're not fighting it, you're trying to understand it. And what's interesting in that process of understanding the other person starts to kind of understand it more.

Speaker 1:

It reminds me of when my son was little. I Would take him to that. There was an indoor playground at Eden Prairie Mall and he'd play with other kids and he was probably like about five, five or six and I watched this kid come up to him and say hey, who's an older kid I think he was closer tonight what's your, what's your name? And my son says spider-man. And the kid goes you're not spider-man, what's your name? And my son's like I'm spider-man. No, you're not, you're not spider-man. My son was yeah, I'm spider-man. And then my son says what's your name? The kid goes Batman, and they and they went off and and they played.

Speaker 1:

And I just thought huh, that is just such a great analogy of sometimes, the things in life that we run into and how we can get other people to kind of join us in the fun and have a different way of seeing it. Now the next question is dear Kelly, what would you consider to be three important habits for an entrepreneur? Three important habits?

Speaker 2:

This is a really tough one for me, because I'm not inherently someone who has a lot of habits in general. I do things differently almost every day or in a different order, but I do think that allows you to, just by you know, driving a different way. You know on your way home or doing you know, trying to see something from a different angle, ordering something different off the menu.

Speaker 2:

I think each of those things they help you to keep yourself from looking at something from only one angle. I think you really need to look at things from a lot of different angles if you're going to be an entrepreneur. And I think another thing that people you know maybe get stuck in a little bit is when they really get married to their own idea and they have a hard time taking that feedback, and we were just talking about that.

Speaker 2:

You know, sometimes I come up with an idea and I think it's amazing and then I ask a few questions and I understand that my paradigm is completely different than what the situation allows. For I think about my mother-in-law and I, in a larger group, volunteer for an organization in South Africa that helps women start their own businesses and they provide microloans and financing and training. But the first time I went there I looked around and I went. You know, they're making all this really cool stuff. How you know we should just have them. You know we'll build a website and we'll have them ship it here to the US. They can be bringing more money into the community and then the people here will be getting these really authentic. You know handmade crafts, and the person I was talking to said you know, that's great, but the streets here don't actually have names and there's no, you know, unless you told somebody to turn at the fence and go down to the fourth house on the right.

Speaker 2:

You know it. Just there's no infrastructure there yet, at least at that point in time was no infrastructure for it, and I thought, oh yeah, it's. You know, if you're taking your set of ideas from the life that you've lived and the experiences that you've had, and then you're going into a completely foreign environment, you need to be first prepared to ask a lot of questions, be prepared to listen and be prepared to like really absorb that information and be willing to make changes. Habits, though.

Speaker 1:

I digress Now on the Habit Front that is something that I would say I think is a habit for you, because I've seen you do it even with the hotel project, where we hosted different public feedback sessions and ran them. You know, ran ideas by them of hey, we were thinking of doing this, what do you think about that, what do you think about this, and then got that feedback from them and some of it was very different from maybe kind of what the original plan was, and I've seen you make changes then to these plans to fit what people are looking for. So maybe it is that being willing to, being willing to listen.

Speaker 2:

I mean really I think as an entrepreneur, really the goal should be to be solving some kind of a problem or filling a hole in the market. So I think you really do need to be honest about if you really get too married to your idea in the beginning and you aren't prepared to listen. You might build this amazing thing that doesn't have an audience or doesn't have a client or a customer.

Speaker 2:

So that would be, you know something, definitely to practice up on your listening skills. Another one is, for me, let all the things marinate during the day. I'm gathering information all during the day and then I try to really clear my head before I go to sleep and just fall asleep. And I mean obviously, natalie, you know this because I'm usually sending an email in the middle of the night. But I wake up in the middle of the night and I have an idea. It becomes really clear for me what I need to do moving forward, and I will grab my phone and I will scribble down furious notes or I will email the team in the middle of the night. Hopefully they all have turned off their notifications.

Speaker 1:

Oh yeah, I always put my phone silent when I go to bed. That's why I've always said go ahead and reach out, tell my real estate clients that too. I'm like, if you have a thought or something in the middle of the night, text me, because my phone will be on, do not disturb, but then I'll get it and you don't lose that. Some people keep a notepad next to their bed and do a similar thing. I'm curious how do you clear your head at night? Do you have kind of a routine that you do, or is it just kind of just sitting there and Like, literally just okay, I'm kind of finding this quiet time.

Speaker 2:

Well, interestingly, when, when I was in kindergarten, they pulled me out of class and they did some kind of test and they were, like we're gonna put you in this group and they're they called it high potential at the time and All it was then was once a week you went down to the library. There may be six kids there, and in this case it was just me and two. There were five other kids, but they were all quite a bit older than I was, so but in that group they, you know, were just saying that they've identified these kids as potentially, you know, just having a different learning style. So that's how I would relate it today. But they taught us how to Really had color. It was like a lead meditation, almost so interesting.

Speaker 2:

Um, I Remember doing that from the time I was really young. Then I was probably six or seven when I learned how to do it. But you know, it was just really Focusing on all the different parts of your body and just letting them relax and gosh, I can even remember being really little and you know when they teach you in, you know to Stop, drop and roll like you were ever on fire and then all of a sudden you're a little kid and you really think gosh, at some point in my life I am going to be on fire.

Speaker 2:

Exactly so that became a lot of anxiety for me.

Speaker 2:

Like I, even you know, I thought about the house burning down or whatever but you know, in this meditation I had learned how to kind of isolate the different parts of my body and I thought, you know what? I'm just gonna pretend that I am reaching down to my toes with a big strainer and I'm gonna strain all of the negative thoughts and all of the negative energy all the way up until I get all the way To the top of my head and I'm gonna tie that bundle together and I'm gonna throw it out into a black hole and outer space. Because this is the way my six year old brain worked, but it works actually, even as an adult. To just think about clearing your mind and clearing out all that negative energy, I really I don't watch scary movies, I don't watch scary things.

Speaker 2:

I don't watch the news before I go to bed, you know, I just try to keep as many positive thoughts in my brain as yeah, humanly possible.

Speaker 1:

And I think that's a really good habit. That's kind of like a really good third habit we're talking about on this question. That's so interesting to me that that was when you were in kindergarten, because you hear these days about schools where they're doing that with children, encouraging them to meditate and what it does for them is absolutely amazing that they would have done that back then. Yeah, that was the early 80s. Yeah, that was really really ahead of their time.

Speaker 2:

So what if you're out there, the people who put that on?

Speaker 1:

yeah, and what? And you look at all these years later that if you've been doing that this whole time, that I think really hits home as a habit that you've used that entire time Not going to bed with all these negative, negative thoughts, getting rid of it, and you know, like you said, woken up with those ideas.

Speaker 2:

I think it's just really clear space for your your brain to be doing the thinking at night.

Speaker 1:

Mm-hmm, oh, I love that one. That's a good one. All right, here is another one. Dear Kelly, when you have an idea, how do you develop it? Do you have set steps of? First I come up with a name, then I find a URL which is, you know, a website address? I Think what this person is looking for is kind of like what's your process to go from Back of the napkin kind of idea, because you've talked about that before on Tonka talk where you'll You'll get an idea, and it's literally on the back of a napkin. In fact, I've seen these napkins on our desk. We don't throw anything away off of off of your desk because sometimes you just don't know what on there that you've scribbled on it's usually like a Piece of paper and there's something written this way and something sideways, and maybe something more a little bit upside down.

Speaker 1:

Yeah, do you have a process to go from. When you get an idea to is it, do you find yourself following the same routine in Terms of how you set it up, I think. I think that's kind of what they're looking for, is they're kind of a series of steps that you, that you take okay.

Speaker 2:

So most of the time I Will get an idea and, like I said, first thing I'm usually doing is scribbling it down. It's a lot of times really an inopportune time to be scribbling it down, like the middle of the night, or you know, I'll be just in conversation with someone and I think actually there's a lot of ideas that come up this way You're in conversation with someone, you're talking, they're giving input, it's leading down a path, and all of a sudden you go, oh my gosh, that's a really great idea. And I think for a lot of people they leave it there and Usually I'm like no, no, that really is a really great idea. And then I will, I will scribble it down, and a Lot of times I do love to think about a name first, not always, but I like to think about a name because it really draws me and it makes it feel more real.

Speaker 2:

But I try not to get married to the name until I find out that there's a domain available that's going to work for it. So I used to just go straight to GoDaddy and I'm typing all the things in, but now I go to Instant Domain Search because you can type in three, four letters and it's going to tell you this is available or it's not available. You can just keep editing until you find something that does work, which is actually how I came up with shortlist properties.

Speaker 1:

Oh, I was wondering. I know we're going through the process and this is our real estate brokerage of names and there were a few different names and then next we know you had this great name logo, everything.

Speaker 2:

Oh, that's another one. Then after that, after I get the domain, then I go to Smashing Logo and I go and I just play around until I find something that fits.

Speaker 2:

But really I think brand is a lot more important than I maybe understood in my early career. You need to make sure that you have identified who is your target audience and what is it you're trying to communicate. And then that needs to live through all of the ways that you communicate. So it needs to be in your logo, it needs to be in all of your social media posts, it needs to be in all of your marketing materials.

Speaker 2:

So I would say, if you're a company who says, gosh, we are really playful and we're really fun and we're really X and Y and Z, you don't want to be putting out these super sort of somber serious posts. Do you want to make sure that everything kind of follows that whole brand guideline that you've built for yourself? So, as far as process, a lot of it's very organic, but most of the time we do then end up in a brainstorming session, either myself doing it on my own or doing it with a group or our team. Sometimes I like to think about who's the audience and if I know anybody in my sphere that fits that audience, I reach out to them and try to get advice, or if I can bring them in on the brainstorm, that's even better. But like I was saying before, we put down all the good ideas, we put down all the bad ideas and we really try not to edit that until we actually put everything down.

Speaker 1:

That is a really key point.

Speaker 1:

That's something I've learned in working with you is I've done brainstorming before on my own, but I would edit it as I go and you always say, no, we're just brainstorming, we're putting everything down, there's no bad ideas, and I have tested out this theory with her Like really, how about this? But you're right, there's something about not editing yourself and allowing yourself to just kind of just go through that creative process, and there's something that I feel in my experience it opens up your creativity because you remove this idea that there's a wrong answer.

Speaker 2:

Well, I think when you're in school and the teacher is asking a question, you're sitting there like I think I have the answer. Maybe you raise your hand, but it feels like there's a little bit of shame in shouting out the wrong thing.

Speaker 1:

Yes.

Speaker 2:

So I think when you go into a brainstorm session and you understand that we're all operating on the same set of rules here, where there's no wrong answer, then I think that opens the door for you to really expand into a different part of your brain.

Speaker 1:

I think you're right and I've seen that happen and it does really change the thinking when you get it through your head and honestly it was, I know, the first few times it was difficult for me to make that switch and go.

Speaker 1:

I can be vulnerable and open with my ideas and when you're not editing, it's just there's this free flow of it. It really is this creative process. So for your process it's, you've, like you said, you have an idea. You kind of take a look at branding and the URL, having being able to have a website that's related to what you're thinking, and then you build it out for there from there. So it's interesting to me because it seems like it all starts with that core brand and then bringing in people. So, say, if it's an idea for pets, maybe you talk to people who have pets and you flush it out more and more. And it's interesting the way these questions flow is it really kind of goes back to you know three important habits, like you were saying being curious, not being afraid to ask questions, and that self care of really getting your mind quieted and getting rid of those negative energies from the day, because anybody walking through life, especially if you're trying to do anything slightly outside the box.

Speaker 2:

Yeah, you really do have to kind of let some of that just roll off your back, because people are bringing to the table their set of experiences, right, and they don't always know exactly what you're trying to do. They maybe heard the first little piece of it and made a snap judgment about whether or not that was going to work or not work.

Speaker 2:

One thing that was really hard for me when I was getting started was taking the negative feedback. I mean, there are some people who you really okay, this person has experience in this area and I really needed to tune into this. And then there are some other people who a lot of times there are people who are really close to you in life but they're warriors. You know, they're really concerned. Maybe there's a little skeptical, maybe they're. I sometimes I think of them as pessimists, but I think most of the time if you ask them they just say they're realists. But a lot of that time those people they're really trying to like help you avoid some catastrophe.

Speaker 2:

They really feel like they're trying to protect you from this thing, and I'm not saying you should go out and take unnecessary risks by any means, but I do think so. When my it was gosh, I'm trying to think maybe 2007, I was throwing a birthday party for my late husband's mother and we wanted a cake for someone to jump out of for her as a gag at the party, and we couldn't find one. So we looked online and we found all of these people who were also looking for cakes for people to jump out of. But you could only rent one if you lived within so many miles of Las Vegas and it was like 300 bucks for the weekend and I'm like that's way too expensive. And so we went back and we made this cake and then we had someone jump out of it dressed in costume for her birthday and it was hilarious. We all had a great time. It was a really memorable moment.

Speaker 2:

And then we thought, gosh, you know that wasn't that hard and there were all these people who were looking for these cakes. Maybe we should just put together a little GoDaddy website five pages, put it together myself. It was not great, but it did the job. We started getting an order a day without doing any marketing at all. You know, three weeks later my husband passed away. But then when I maybe a year after that I said you know, gosh, that was kind of fun and it felt good to be part of everyone's celebration and they were all excited. So I redesigned it, I got a patent on it and then we started, you know, selling them on this website and we were selling them to Dubai and Wow.

Speaker 1:

Yeah, you got a patent on it, right.

Speaker 2:

A patent? Yeah, germany, canada, australia. I couldn't believe how many people were jumping out of cakes in Australia. But anyway, like I said, that was just a little small idea and I didn't have any experience in manufacturing or patents. That was my first patent, but it was just being willing. Seeing this whole in the market, seeing a need, also seeing how fun it was for everyone who was you know we had some great, great feedback on those.

Speaker 2:

I had a 17 year old kid reach out and say, hey, I wanna jump out of a cake to invite my girlfriend to prom. Oh, you know like I sent it out and then three days later I get a text message. It's like 11 o'clock at night. She said, yes, oh, it was just. We had a soldier jump out of one to surprise his wife when he came back from serving. So we had some really great yeah, really great stories through that. But I think you know this willingness to step out into the unknown, where maybe you don't really actually have any experience, but being willing to learn is a good spot to start.

Speaker 1:

Yeah, that is. Those are really really good answers. It's a good thing this is on video because I don't have to take notes. Yeah Well, thank you so much again for another awesome Ask Kelly. You're welcome. Go ahead and email Natalie at TonkaTalkcom and just put in the subject Ask Kelly, because then we'll know where to put that and on Mondays we'll go through these questions, We'll get to as many of them as we can and we can pick a brain on how to get your idea going, how to maybe create some community around it. The great thing about this is the more you talk about and you share your idea and what you want to get going, because we have such a large community, you never know, we might know someone that can work with you on that. It's just we want to do this basically in the spirit of just creating more community and finding more connection for people.

Speaker 2:

Absolutely. I love being a connector, trying to put people with the people they need to make their ideas and dreams happen.

Speaker 1:

Oh yeah, dream job. Well, thank you everyone else Welcome.

Speaker 2:

thank you, Nat.

Speaker 1:

I'll talk to you later. Bye.

People on this episode

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Natalie Webster

Host
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Kelly Olsen

Co-host