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Start a Business Before You Feel Ready | Do Small Business like a Big Boss · Do Small Business Like a Big Boss Podcast

• SBBB Dalka Riversie Audio: I had left a job to take another job and it was supposed to be a huge step up. It was a chaos. I was there for six weeks. It was awful. And it doesn't make me a bad person to say no, and it doesn't make me a bad person to do the work that I do, get paid fairly and I thought if they are tanking, I will succeed. Welcome to Do Small Business Like a Big Boss, where we explore the real stories, hard earned lessons, and game. Changing strategies of entrepreneurs who've moved beyond the side hustle and build businesses that scale with confidence. I'm your host, Aisha Jorge Massingill, your small business legal guy. Let's dive in. What up, bosses? Welcome to the latest episode of Do Small Business Like a Big Boss. I am your host, Aisha Jorge Massingill, your small business legal guide. And today I'd like to welcome Jessica Delka to the show. Jessica is the owner and founder of Chicago Planner Magazine, an approachable, no fluff resource for events and hospitality industry in Chicago. She started it while working in restaurants and hotels, simply as a way to learn the events world and has kept it going through a pandemic. And several big name event jobs. With a background in advertising and PR and a career designing events for 500 Fortune 500 executives, celebrities, athletes, politicians, Jessica knows how to build a business connecting people. Today we're talking about starting before you feel ready, wearing every hat, and building your own thing alongside a full-time job. And maybe we'll even talk about whether she's met President Obama. Welcome, Jessica. Thank you so much for having me, Aisha. That was such an incredible intro. You made me sound amazing. You are amazing. And now we're gonna allow our listeners and viewers to find out why. So today you're at the helm of the Chicago Planner magazine, but you studied advertising, PR and media buying, all those other things. I always ask, at what point did you have a spark to think, I wanna build something of my own? I think that's a great question and I appreciate you asking it because I think a lot of people have this feeling of, well, I have this idea when I'm at work. Well, I feel like I know how to execute this. But it can be hard to feel like you either have the autonomy to do it or it's scary to go out on your own. So for me, I actually started Chicago Planner Magazine as just like a little blog called the Chicago event planner, because as you mentioned, I had an advertising and PR background. But I was suddenly I started op I opened for Mastro Steakhouse in Chicago and we were doing big events. they hired me as the hostess because they saw my experience. They're like, you've never worked in restaurants. And I didn't understand when you are at the top level fine dining. a lot of people have master's degrees. And I don't think people realize how educated a lot of high-end servers are. And so we were doing dinners for really big names. we would have the CEO of Boeing come in on the regular. We had, I once ended up doing a dinner for Michael Jordan and his family. So you have to know what you're doing. And I was like, what if I just take my writing skills and my, you know, kind of education background that's more communications focused and offer to interview people or just try to use this as an education tool. And and that evolved and it it became something where I was like, I think I want to give this a try. And it's not to say that it's easy, but I think when you're somebody who always wants to be at the next level, you realize that you have to make that decision for yourself. And you can't always let other people define who you get to be based on their own experience or how they think you should be. And I found that very limiting at times. So I think that was my main driver. Yeah, thank you for that. what I have found in my experience is that people are very open bleeding their fears onto you when you share your dream. And and I recall one time where was like having this networking meeting with this guy who was a general counsel of an organization and I said, Hey, I aspire to be a general counsel one day. And he basically spent the next fifteen minutes telling me all the reasons why I would never be a general counsel. And I would I I affectionally referred to him as the dream killer. 'Cause I'm just like, I left there so deflated. And then, you talk to family members and you're like, hey, I'm trying to try to do this. I'm t well, that hey, you're not gonna make a lot of money or how just all the things, in terms of their own fear. So what did you tap into, I guess, not to take on some of the concerns that other people may have had about your decision to, you know, get out on your own? I think there was a point where I realized in multiple jobs where I had really good relationships with a lot of people who were at my level or lower, but where I started to get friction was people who were above me or management. And not everyone, of course, I worked with some incredible people, but you realize when you kind of strip it back, you're like, why are you not approving this idea or why don't you want to hear anything? And you start to realize they don't want to be challenged. Because everybody wants to look good. Everybody wants the promotion. And it's hard to strike that balance of making someone else look good as part of your role and then having someone else take your ideas and they get to ascend, but they're gonna keep you down. And I think some of that is where I was like, you know what? If if they can do all these things and they're using my ideas or they don't have all of these pieces that I think might be necessary for that level in leadership, but they're doing it anyway. Why can't I do it anyway? and not do it in a way where I have to push others down. But I felt so empowered by the people who love to work with me. I mean, I literally saw somebody last week at a networking event who I hadn't seen in almost a decade. And he gave me the biggest hug and he said, It was so great to see you. And, knowing that you can leave that positive impact on other people, I think should be a motivator to say, a lot of people deserve better. And maybe I'm the person to do that. There's a lot to unpack there in terms of you know, I think it's very common in in corporate America in particular for people to take your ideas without attribution, but the inverse is not true. I bet if your ideas weren't great and they were disaster that those people the first thing be Yeah, that was Jessica. Right. Yeah, there's that too. So, you always want to be a good employee, but you don't want it to be so good that it's at your own expense. Yeah. because to me it's just like, what would it have taken that person to say, hey, and this fantastic idea that Jessica came up with is blah, blah, blah. So they still get to they get to actually look brilliant. for working with you and bringing you along and presenting a great idea. But I just think there's some people who are just not great leaders and and it's their again this idea of their own insecurity. so while you were working in the restaurants and at the hotels and you're you know, some of the thing is like the challenge of building stuff on the side. What did your days and nights and week, especially like in the hospitality, you know, how are you sleeping or just conducting everyday life and getting your work done on both sides? I think in full honesty, at that point in my early twenties, I was very career focused. I didn't date a lot. I didn't I knew people who are married with kids and I was like, I don't even know if I've had a real relationship yet, because I will go to work and I would spend time with friends. It's not like I would never go out, but I would come home and usually write. There was a point in time where Over the course of a few years, I could count on my hand the number of times I even turned on the TV. And that's not my life now. I'm I think I do try to value a little bit more work-life balance. I have incredible respect for anybody who has a full-time job and a family and they're either going back to school, they're doing something on the side, because I really tried to make the most of the years where I didn't have as much responsibility to other people. And so I think that helped me get to a certain level. But I will say that, when the pandemic hit, everyone was forced to be inside. There were times where I was at three networking events in a day and I would just hit everything and I would try to see as many people and hand out as many business cards. And I think that got me to a certain point. But then you also have to decide your time, right? Like is this actually the most effective way to spend my time? And am I really honing in on the right audience. And so I think in what I'm calling Chicago Planner 2.0, it's not about doing the most, it's about being the most efficient. I really love that. I have shared on the program previously that one of the things that I ask myself whenever I'm going to any kind of like event or something that requires my in-person attendance is was that time well spent? And so, you know, we were talking a little bit before the show. I'm just coming over from an event with our local economic development authority and I'm meeting small business owners and I'm talking to the guy next to me and he's like, Did you get any good leads out of it? And, you know, I said, listen, when you're talking to other small business owners, it's a slow burn. So it's not like anyone is saying, I'm gonna buy the widget here. But at the end of it, I always feel like for that particular entity, it was time well spent. And the funny thing is this is my second year doing this particular event. And now people are coming in and we're like, hey, I know you. And we are developing like my my word on the back end of 2026 is sticky. Like my desire is to be sticky with people, like that, you know, they start to go, because you know, we all want to be top of mind and blah, blah, blah. So for you, how did you what was your process for deciding, I'm gonna go to this event, I'm gonna go pass on this event. I need to rest today. No, today I have to push through. tell me about your process for that. Yeah, I think that's such I love you using the word sticky, Aisha, because I I feel that too. And I think a lot of times I will explain to people, you know, they'll say, Well, are you getting paid to do that? And it's like it's a like you said, a slow burn. There are people where it's been years before you kind of see that turnaround. But the hard thing is, you can't as an individual or a small business come out with the brand recognition of a Nike, right? Or pick a big business. And so people really, ironically, are less trustful of smaller investments that they don't know. They're gonna they're more likely to spend five hundred dollars buying the hoodies and the shoes than they are coming to your business even if you're asking them for three hundred dollars, right? I think that's the small business struggle. And so you really have to be present. And I think even if I had to start from scratch, I'd probably be at more events than I am now. But part of those really spending many years is that I look at an event and I'm like, if I've gone before, do I know half the room already? And I wouldn't have that decision if I hadn't put in a different type of hard work when I was younger. And so I don't want to necessarily invalidate some of that, but I do think that we are also in a little bit of a different world. And I have this discussion. With other business leaders and especially associations, people who are putting on networking events, because they're saying, how do we get people to come? Because people have so many distractions, so many options. And so it's not just me deciding is this gonna be the right people, but it's everyone else. And so I think when I'm looking at something, I look at who's the audience. Is it overall like you're talking about the economics event you went to? that so I think you really have to step outside of your own industry because if you only go to your own industry events, it gets to be a little bit too small small problems, right? Yeah. Yeah. So I try to see what's going to be an efficient way to expand my horizon to the right market. And if it's repetitive, like I've gotten to the point where there's Chicago has a really high density of associations. They may even have the largest in the country. We have a lot of associations here. So, maybe I hit those once a year. You know, I don't necessarily have time to go to every single event every person has, but I do want to keep in touch with the organizers and the right people. So that's kind of a long winded. But you know, there's just I think it it you have to decide what's right for you as well. Well we're gonna take a quick pause. But my boss is listen, If this conversation is giving you something, do me a favor. I need you to hit like, follow the show, and subscribe, whatever you're listening or watching. It's totally free. Takes you two seconds, and it's how we keep bringing you guests like Jessica, who's been amazing. Okay, back to it. I'm curious, I wanna go back a little bit just because I'm an aspiring writer and I'm getting ready to launch on this journey. How do you carve out time? tell me a little bit about your writing process. do you 'cause you said some point you turn the TV off or whatever, but what's your writing process when you have to get stuff done? I think writing is challenging to switch with what I do because I was initially like a creative writer. I was first published when I was ten years old. And I had something it like I think later it might have been like it was interesting, but I did it from the ages ten to twenty. I would get a poem published every year. And I w really came from that creative writing. And, you know, I still remember taking a writing class in college. And I was red inking everyone's paper more than the professor because I was like, this is what a semicolon is. This is how you use dash, you know, and had a story where everybody literally we would critique each other and all anybody said to me is what happens next. And so my mom has been after me to write a book. But I think that it's what I've really learned is there's a big difference in writing style when you are writing either B2B, when you're representing any kind of business or corporation, and even social media, because those are all their own entities. And I find that when I'm doing a lot of business things, like of course I have a lot of meetings, I go to events, I we have like over forty PR firms that we work with. So it you really have to switch it off. And there are days where if I can tell my brain is in writing mode, I might if it's not a big deal, I'll cancel whatever I had on my to-do list. I'm like, I'm gonna write it. I'm gonna write it right now before the feeling goes away. because I think for me, you do need to have it to be I feel like to be a business owner, you have to really have the capacity to co compartmentalize. And so that can still be hard if you're trying to do something that's just almost of your own essence, right? You have to shut out all of the notifications and everybody's input and things like that. So it doesn't always mean going to a quiet space, but I love a notebook. Sometimes I will manually write something because I also think it is hard to not get a ding. And even on your laptop, who you know, I'll at least like I I mean there is literally like I have like 50 notebooks. I have so so many. And it's just because I think you need a little bit of separation. and while that may not be the case for everybody, to me, I'm I'm old school. I love my quiet corner and a notebook. I l I absolutely love that. And I know for me, the the idea of like in your brain, you have certain window to achieve a certain kind of task is really important. So like for me. I am a workout in the morning girl. That's when my brain is primed to go do that thing. When I get to the end of the day, I feel the weight of the day. All I want to do is sit down. I don't want to do nothing. I have people in my life that they love working out in the afternoon, the evening. And I'm like, I don't know how you do it. Cause by the end of the day, I'm done. And it's the same thing with work. as a lawyer, one of my big pet peeves when I was in corporate, it's like, can you take a quick look at this? It should only take you a second. And I was like, mm. How long do you know? How how do you know how long it's gonna take me? It is a different kind of work when you are reviewing something for someone and giving it the attention it deserves. So you gotta be like in the environmental space, the mental space, all of that space to get that kind of thing done. So I love what you what you said about that, even making space for yourself by canceling other things when you 'cause you're like Carpe Diem, it's yes, you know, like seize it now. So you just again you're doing all these side things and everything. Was there a time when you're saying, hey, this is feeling like a real business? I'm a big girl. can you identify a time or or a season where it started to feel like that for you? I can be really transparent about this in a way that most people wouldn't be. I had left a job to take another job and it was supposed to be a huge step up. It was a chaos. I was there for six weeks. It was awful. And I was like, I've had it. And that was it. It wasn't like this moment of inspiration. It was a moment of exhaustion where I was like, people cannot be this crazy. I cannot deal with this anymore. And so you will not find that job anywhere on my resume. I did meet a couple of amazing people I'm still in touch with through that job, but I was just like, This has to be it. And I think I that was a moment where after seeing someone who own this business that I had thought was much more impactful. It was supposed to be more of a international position for me. And I thought, if they are tanking, I will succeed. So I after that was over, after that six weeks, I was like, that's it. I'm doing it for me. Good for you. So so we actually have a little bit of of that in common where I was at a job, I wasn't happy, I left to go get another job. And I was like, this is the same I'm not. And then I had a little thing where one of my kids was he was in some pretty serious stuff and I had to fly out to support him. And I asked them, I need a little breathing space for the next couple of days. I'm not accessible. did they try to access me? And I had a Zoom meeting and I'm in a hotel in Texas. And I hung up the phone and I said, hell no. And I had actually planned a much longer tale to launch my business. But it was in that moment moment I knew. And and I was telling the story to a friend last night and I said, and I woke up the next day and I had the peace that surpasses all understanding. there was no panic, my God, what have you done? It was like, nope. Time to go. And and I had a call of my boss and I was like, Yeah, I'm I'm going. I'll give you guys a long tail. And I gave them like six weeks to wind everything down. But I've never been so sure of something professionally. in my life. So I wish that for everyone watching and listening, that when you do get to the point where you're ready to go, that you have peace about it because you just know this is the thing that has to happen. But in your early days while you're writing and you're designing and you're doing socials and all that stuff, did you find that there was one hat or duty that was the hardest to wear or juggle as you were building? I think the hardest part in the early days is I don't think I started out digital and I don't think people at in twenty twenty six remember how little digital we had back in twenty sixteen. and even from twenty twelve. I spent so much time explaining to people in leadership roles what digital was. They could not and some of it is because, you know, yeah, sure the younger people working for them knew what it was. But I remember sitting on the phone with someone and literally saying, How do you look up something. Do you go to Google and look on your phone or do you still go to a phone book? And they were like, well, I use my phone. I'm like, that's what digital is. And so prior to 2020 and that time frame of when I decided to start full time, that was honestly the hardest part. Yeah. But let me ask you this woman of so many notebooks, did you ever have a thought about a paper magazine rather than digital? Well, to be fully transparent, digital was more accessible and affordable, right? Yeah. I know it's super expensive. It is. And so last year we did print one of our issues, our holiday guide. It's one of the most popular things that we do. And so we got it in print. And next year I am looking at doing the quarterly issues as printed. We're still kind of figuring all that out. and I think that it's also part of a mix because the constant fight between print and digital is how are people finding you? Because it's either circulation, but people, I think now we're almost coming back full circle because people are so inundated digitally that it's overwhelming, right? Like you now they put ads inside of ads and you're like, I'm just trying to get to this end product. And so I am noticing that there is sort of this desire for that 90s nostalgia that people keep talking about and this analog where what you want is what you get. however, how do still people are searching and now we've got AI that's getting thrown into the mix whether people want it or not. And so you really are, it's not even about which is right and which is wrong. It's about if people are relying on you to get a message out, what is actually going to be successful, not just for myself, but for my clients. I I love the hybrid mix to so I love the fact that you I mean like pay for the get one sent to me when you do your your quarterly edition. so I did read where you gave some advice that said basically like get through the one step, make sure it works, and then you kind of layer on. But was there a time that you violated your own rules and then like tried the one step and then skipped and then had to like come back or just didn't work out the way that you thought it would? I think there are the things that didn't work out the way I thought, I think are more on the once you put something into the water and it's how people receive it. But that is actually where I realized that I you do have to do one thing and move on because I think the beautiful thing about small business is you can have that agility that large companies don't have and you're not just a cog in the machine recognizing that there's more cogs about to break the machine. But you can actually say, let's fix it. And so I find that you end up having the best product or whatever you're offering when you put something out there and wait to get some feedback. and I think it's important before you invest too much or ask others to invest too much. And it is like probably controversially, I'm a little bit against some of the venture capitalism because I'm thinking, why are you putting a hundred million dollars in something that hasn't had a proper market test? Right. And we're seeing some of these businesses. I think WeWork was a great example of that. I know they've tried to come back, but there are some industries where we're seeing that millions, if not billions, of dollars are being put in and it's like, Well, we did the math and it should work. It's like, Yeah, but you didn't think of these other factors that you know, would impact it and I there was somebody I studied abroad with, and I remember hearing him talk about the fact that he was walk working for this organization that helped provide clean water. And he said, you know, the one thing we didn't expect is where where we went into these places where they didn't always have clean water is they were used to the taste. And so they weren't drinking it once it was clean because it wasn't familiar to them. And I feel like that's an example that kind of resonates through business, is that you can have the best concept. But if people aren't receptive to it, it may not be for the reason you expect. And so if you you know, it doesn't mean that you have to be slow moving, but maybe that if you want to move within a certain timeline, the pieces are smaller. So you make sure everything is correct before you go and make it bigger. Man, that's so good. That's so good. Cause I I think one of the things that I see myself or other entrepreneurs struggle with is like, It's a great product. It's a great idea. But that's you and your mama that agree on that. Like that like Yeah, you know, and your daddy, your mom like, yeah, baby, that's good. That's a good one. But you're the only ones who think that. And I've been speaking a lot in different groups lately about your ability to understand your own value and that someone else's inability to see the value in what you're presenting to them doesn't necessarily have to be about you. It just may be about their inability to see it. But there is still like a psychological thing, like nobody loves me that you have to to grapple with when you're building. So I do love this like, let's have this proof of concept, see if it works, and then figure out like, that's a data point. The water tasted different. Is there something that we can do to adjust? And you're right, you can you can be more nimble as a small business owner to make that shift. And speaking of money, one of the things that I've heard you say is, I would you wish that you had known it was okay to prioritize money along with vision. and stop saying, Yes, I can do anything, I can take all the things. two sides, like, was there a time where you said yes to something that you regretted? Or when you said no and felt like really good about it, knew it was the right thing. I think the biggest turnaround for me was actually the pandemic because I went to Catholic school. I grew up in a way where in service to others was a really big message. And I took it to heart. And in hospitality, having that mindset serves you really well because there's nothing to me more gratifying than working really hard and then seeing the joy on someone's face like I remember one time I did a birthday dinner for a one-year-old, which why they had it a a big fancy place. That's their business. but like the the father came up to me, he goes, You know, this was one of the best events I've ever been a part of. And for his job, he's like, I've done events every year for different things, and this was the best. And that was one of the moments early on in my career where I was like, maybe this is for me, because it brought me joy to do it. And so I think that you get to this point where at what point does bringing other people joy or feeling like you're doing something well deplete you? And some of that is because it turns into something where people start to expect you to do something for free or they expect your services that they would pay for someone else and but they go, but you you know, you don't want to build the wrong reputation. and it's hard when you're starting out because I think especially as women and if you are a woman of color times ten, you're like always told that, you know, this is your lane, this is you shouldn't ask for more. We all know that we have to be twice as good to get half as much. And so you you absorb that to a point, but then you realize, hey, I still have to pay my bills, right? Your joy is not getting a cover my utilities and my rent or whatever mortgage, whatever you've got. And so when the pandemic hit, we watched everybody fall apart in an interesting way, whether it was an industry or there were just so many things happening. And it was a little bit it if I remember the way I remember is it felt a little more dog eat dog, where it's like, listen, I have to we don't know what's coming around the corner. We don't know how this is gonna how long this is gonna last. And you have to be a little bit sharper and you have to say no and you have to be better at identifying earlier When someone isn't planning to pay you, but they want to make feel like they are going to give you this great amount. And I think it forced me out of what I don't want to say a comfort zone, but what I had thought was right. And I realized that I'm not trying to take anything away from people, but I also shouldn't be run over, you know, by people who want to take advantage. And it doesn't make me a bad person. To say no, and it doesn't make me a bad person to do the work that I do, get paid fairly, because at the end of the day, I know that if given the opportunity, I'll try to do more good with it than bad. And I've just watched all these people get a bunch of money and not do good with it. So what's so wrong with me asking for a fair price? Preach. Listen. part of the whole structure of my firm is to make legal services accessible, not cheap, but accessible to small business owners. And it frustrates me to no end. This I'm, you know, I'm in a a million communities. So for the listeners, don't be in all the communities. Like your time is limited. But this woman says, hey, I know Aisha's the lawyer in the group, you know, my mom says that for my business, I need to get some legal service. But I need, but I don't really have budget for it. I need it to be on the cheap, cheap, cheap. And I ended up doing a voice note to the community. And I was like, if you want someone to give you side legal services, the quality of that is gonna be like is side stuff. You're gonna get their leftovers. And I have to eat and I have to feed my family. So, but y'all be the same ones that will go out and buy the purse and put it on layaway, the designer bag or whatever. But for someone else's profession they've poured their heart and soul in, you want the discount. And I I it's taken me some time to be be like, no, that that's a quick note. On the flip side, to your point about service, my beautiful aunt who raised me, who's now 82 years old, when I first started on this journey, one of the words of wisdom she gave me was be of service, period. So that being of service, but also respecting that you have a right to earn money and eat. Like no one should feel bad about that. So At any rate, that's my big my big rant for the day on that. No, I'm with you. And I I would up that to more my pet peeves is when people say, you know, when they talk about labor and they say unskilled labor and I say that's no such thing. It's patriarchy and it's capitalism at its worst. Because I don't know if you've ever tried to make some of those crazy coffee drinks that people say unskilled. But I tell you what, mine doesn't taste as good. You know, so If they're needed at a job, it's a skill. Because if it wasn't, it wouldn't be a job. So I think we really in every role, in every position, need to show respect to people working at every level because they're needed where they are. I I I grew up in the Bronx, very poor. And and so I'm very passionate about these kinds of things of like people who are out there just getting up every day and it ain't sexy, but they're getting it done. Absolutely. We are engaged there. They're getting it done. so okay, we're gonna get off our soapbox. We're gonna get back to the do a small business like a big boss. So eventually you are working with these Fortune 500 companies and these C suite executives. Were there any like big business habits or things that you borrowed as a new founder or owner and like brought over to your business? I think that the main thing I I think that there are nuances and I think the unexpected thing is that people think that someone in events, one that it's just parties. People don't understand how intense it can be and in when you're in corporate, there are people who are just right under the C suite and technically what they're doing is in the events world because it does tie into sales and things like that. But I think one of the most important things you can do is be well read across industries because I always say every company has a holiday party, right? Every type of business is going to do something where they're dealing with clients or they have an event that is important to their industry. And so the more you you know about this is how it goes in finance, but this is how people in sales and actually if you're in medical, and not that you have to be super knowledgeable about each, but the more that you can speak to someone's language that they use in-house, the more they trust you. And the one skill I've really worked to hone in on is how do you translate creativity into dollar value? I think that's one of the hardest things to do because people not everyone is conceptual and creative. And I feel like at my core, I'm a creative person who had to learn business. And so I really I think that was also part of the growth to the question before of what changed for you? And that's like, how do I get people to understand how many pieces are in this? It may be a thought process, but for me, it comes from X number of years of experience or so many conversations. So how do I take this concept of what they want and show them the steps and show them the monetary value? Love that. so you I've heard you talk about valuing your time and you know, like, can we have a fifteen minute conversation instead of a whole hour? Why do you wanna meet with me? one of my old bosses, she would always like, I'm not gonna participate in a meeting unless there's an agenda. Like, what you're not gonna do is is waste my time. How do you decide what gets a spot on your calendar? I will say I try to make room for young and up and coming people on the industry. If somebody's like, I'm doing something for my school, can you, I'll say sure, I'll give you 15 minutes. Because I really do think that we have an obligation to the next generation to make them as good as they can be. But I also feel like by the time we have a calendar discussion, I should have asked you enough questions to understand what are you doing? Why did you reach out to me if that's the case? what are your goals and so essentially pre-qualify somebody before we go into that 15 minute meeting. And I really did I think in recent years switch to 15 minutes because I found that when I pre-qualified somebody enough to get to that next step, if it wasn't a warm lead, if it was just a cold outreach, that it's like then I've I always like there have been times where I'm like, well actually we're at 10 minutes and we're good. Thanks. Bye. You know, like I think that people respect it because they're busy too. I think people understand your value when you can get to the point. You know, like I I think as a Midwesterner, I know there are some people where culturally you're going to talk for a while and stuff. And then there's people who get right to the point. I will give you one minute of pleasanteries and then we'll get into it. You know what I mean? Like, okay, how are you? I hope you had a nice weekend. Now let's get to it. And I don't think it feels harsh because of the conversations we had before. They know I've asked all of these questions and I've probably looked into prepped for that meeting. And so I have my additional questions and I get right into it. And most times I can knock it out in 15. Yeah, that's so important. Like the key phrase for you said for me, like they know you've prepped for the meeting. Like, listen, y'all, you're asking for someone's time. It's a gift. Now, there may be a mutual, mutually beneficial relationship, but like be prepared. And if it says fifteen minutes, be prepared to make it fifteen minutes and like not hope that it drags on. That's the person's prerogative of whether they have time on the back end. But I just find a lot of times people don't tell me your whole life story since Moby Dick was a minnow. Like you asked for the time to talk about this thing. So to your point, a couple of pleasantries, but then like let's get it. I will say that the more serious the person, the more they appreciate that short meeting. It's somebody with nothing to say who's like, Do have an hour? No, I don't. No, no. And when I was in corporate, my my HR friends, I love y'all, but the whole I have a quick question. No, you don't. You ain't got no quick question. It's gonna be 45 minutes. I don't have time for quick question. And I'd be like you. No. Yes. Even in when I've moderated stuff and so they'll have a QA, the person who says quick question is the longest every event. And you're like all these questions and a short essay. All right, we're gonna take a little beat because every business owner listening knows that one contract, one client engagement, and one handshake deal can come back to bite you. That's why Cedric Andrews has put together a free legal risk assessment, a quick way to spot gaps before they cost you. Grab yours at smallbizleguide.com. That is biz with two Z legal guide. Go get protected and come on right back. All right. So we've talked about time management, being outside at events, straddling both worlds and and talking about y you know when it's time to to finally go. but are there, now that you're in it, are there different tools or parts of your routine that like you can't live without and help keep you on track? My calendar. I always say if it's not on my calendar, it doesn't exist. I say that same thing. Because I forget stuff now. So for real, for real. If it ain't there, it it doesn't exist. Yes. I get a lot of invites. There's a lot of overlap, especially when you work with me any kind of media. There's a lot of different media events happening. And so I have to put it down because otherwise it just c it'll all come crashing in. It is. It's it's crazy. it is a gut punch when I realize I have forgotten something because it's not on the calendar. And I'm just like scrambling. But do you are you someone who blocks your calendar by certain themes, like how we talked earlier about if you're in a writing mode, you want to be in that writing space, do you just take all the meetings on all the days or are there times where you block for certain things? I think it if I try to do that more if they're in person, because to me a virtual is much easier to knock out. It's basically the modern phone call, right? But when y I f and I forget because I get to be remote working for myself being primarily digital. And so I kind of get to set my schedule. And, you know, there was a time where I was in the office five days a week and you better be here by 8 30 or else. But you sometimes I forget like when you just hop on, like yeah, I'll hop on in eight o'clock with somebody, especially when you're dealing with different time zones. But when you have to like get up and get there and you account for the travel time, even if it's a fifteen minute walk. But what if it runs over? And this, I find that, you go from being able to do eight meetings in a day if you have to push it to maybe you get three or four. And so since it's like if I'm going to spend that time to get to a certain location, do these steps, let's condense it. And so usually it's more based on do I have something outside of the office to do or more in person work to con to just make sure that then I can spread out my time the rest of the week with deliverables or whatever else I have. Cool. So I got only a couple, three more questions for you because in the spirit of time we're we're near the end of ours. but you talked about swapping the word success for accomplishments or happiness. When you think about the context of the magazine, you know, what is enough look like for you? Like what are you driving towards? I think that I would love to continue to grow and I think media is an interesting place. I also think events are interesting. I think that events are undervalued. and not to harp on the pandemic too much, but I think that was the first time the rest of the world got it because I've been talking to people for years about the work that we do. However, when suddenly people couldn't go to a wedding, they couldn't go celebrate anything. I remember when people were first coming back, I saw people at business conferences, networking events, literally running to hug somebody they hadn't seen. Even at work, right? Where you're like, I don't want to tire these people, I wanna go home. But it's part of human connection. And I think that's a huge part of what makes our society, our communities, and our economy. And so part of my goal isn't just to grow Chicago Planner Magazine. But it's to use Chicago Planner to help people understand the value of an industry that represents billions, if not trillions, of dollars, but is somehow considered less valued than finance or other established industries. Yeah, I love that. now I think I've read you said one of the most common reasons that people give up is not knowing who they are and what they want. You just t talked about the things that you want. If someone is in a, you know, that messy, scared first year right now, is there one or two things that you would tell them so that they could hold on and be encouraged? Yes. I think one of it is you're out here doing it because you either have had an experience or you have a feeling that is driving you in that direction. And there's a reason for it. And I think we don't always appreciate That what's needed isn't the same as everybody else. And it's really hard for people to wrap their head around something they haven't seen before. And that doesn't mean that you can't pay attention to your market, that you shouldn't be looking at the efficacy of your work. But it does mean that, even when I was talking about digital, people, if they haven't seen it, they're just like, Well, what is that? I don't get it. And so that can be a hard pathway to cut through. But if you know deep down that this is what it is. You have to be willing to take the scrapes and the hits, right? You have to be really resilient to people telling you no, to people not believing in you. But if you see that pathway forward, you can't let anything stop you. I love it. My my power word for this year, every year my gym, we pick a word and mine is relentless. So as tired as I am, I'm like, yo, we have to keep going. Let's go. The next event, the next function, you know, the net next networking thing, like. As tired as you are, you just got to keep going. All right. This is it. This is the question that I ask all my guests. When you hear the phrase, do small business like a big boss, what does it mean to you? I think it means honestly, being self defining. Because when you're a boss, when you look at people who are leaders, the main thing that they talk about and relate to is I did this, I set the standard, I created this amazing thing. And so when we think about why well, the reason I say, you know, I think people should acknowledge accomplishment in addition to success is success is ness tied to money. But when you think about impact, that has a much broader definition and it has a wider range of what that means. And so when you're a boss, you get to determine what your own impact is going to be. And that does not have to be defined by anybody else. Love it. Love it. And Jessica, where can we talk a lot about digital and opening up your phone, but where can the people find you in the Chicago Planner magazine? So it's just Chicago Planner Magazine.com for the website. I my Instagram is at Chicago Planner Mag. So just M-A-G short for magazine. And on LinkedIn you can find me at Jessica Delka. It's just my profile is me. I'm lucky enough to have an original enough name. And and my last name is D A L K A, even though it sounds different. and then, you know, I think yeah, Instagram and LinkedIn are kind of my main two, and then of course the website. Okay. Well, thank you so much. I have loved this conversation. Appreciate you giving your time and your talents to the good people today. Thank you so much for having me, Aisha. It was wonderful. Awesome. All right, bosses. Y'all know the deal. No matter what, build that dream messy, you can build that dream scared. Just don't build it small. We'll see you in the next episode.