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Navigating The Workforce Through Networking With Claire Bossong


Are you struggling to get a job? Especially in today’s pandemic landscape, it can be hard to nail down the job of your dreams, but fear not! On today’s show, Claire Bossong holds the answer: networking! Claire is the District Director at State Representative Tom Bennett. She sits down with Rosie Zilinskas today to share how networking can help you get to where you want to be. Tune in to learn more about landing your dream job. Claire and Rosie also discuss time-blocking and the challenges of being in politics as a female and a Millennial.



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Navigating The Workforce Through Networking With Claire Bossong

We are talking to Claire Bossong, and we are going to showcase how Millennials are navigating the workforce. Let me tell you a little bit about Claire. She is 22 years old in 2022, and lives on a small farm in a rural community. She attended the University of Illinois at Urbana-Champagne, where she studied Agricultural and Consumer Economics with a concentration in Public Policy and Law with a minor in Animal Sciences. She is working as a District Director for an Illinois State Representative and plans to move forward in her political career. You will hear from Claire about the challenges of getting a job during a pandemic, being in politics as a female and as a Millennial.



Claire, welcome to the show. I know that you went to the University of Illinois as I did too. The Alma Mater, the University of Illinois, has a saying. Do you know what that saying is, by any chance?


There are a few that I have in my mind, but let’s hear what you are thinking.


It says, “To the happy children of the future, those of the past, send greetings.” I love that saying because I know that many women before me paved the way for women like myself, and I want to do that for women coming up behind me. I know that you and I have been talking for quite a while now, probably a couple of years, and you became employed. I want to start by asking you how difficult was it for you to navigate, trying to get a job during a pandemic, being your first job, and being a Millennial? Tell me about that.


First of all, thank you for having me. I’m super excited for you and to do this for other women to listen, and I’m excited to listen as well. Job searching was difficult. I still imagine that it is, even though I am employed. I started applying for jobs while I was still in college. I graduated in December 2020, a few months before that. I did for several months into 2021 with no luck.


I was applying in multiple states on multiple different job search engines and mailing applications. I’m doing all things like that. I decided to substitute teach while I was doing that for a source of a little income. I know how crazy it was for teachers during the pandemic, but still, I wanted to help out in my community with that.


I did not even apply for the job that I had. It fell on my lap. I can’t even attest to where I would be without this moment that fell in my lap. I got lucky, and not a lot of people do. I have had friends that applied for hundreds of jobs and searched for over a year. They do not get the one that they are looking for. They end up settling, and they are not as happy with where they could be with what they got their degree. It was frustrating. To say the least, I do not think I had it as bad as a lot of other people, but it is a hard time for everyone now. I do not know when it is going to get better job-wise. In Illinois, unemployment is lowering. That is a good thing, but we will see where it goes.


You said a couple of things that I wanted to go back to. You said that a couple of your friends were applying. Did you say hundreds of jobs?


I have friends that were in the 80 to 100 range. I was probably in the 60 to 80 range because there are easier ways to apply for jobs online. You put your resume in, click and send. It is easy to get up to that amount of applications, but to not be hearing back from half of those 80 to 100 jobs is crazy. You do not know if you could have made it or if they hired someone else. It is an endless waiting game for something that you were excited for.


You and I did some networking. How good were you at networking?


Thanks to my mother, I’m good at networking. I like to talk to people. I can pretty much talk to anybody about whatever. That has been helpful. The choice of an industry that I have chosen to go into is the political world. It is all about networking, all about meeting people. If you are quiet, do not like to talk, and do not put yourself out there, you are not going to go as far as someone who is constantly networking. That comes easy to me. It does not for a lot of people, especially during the pandemic. When you can’t be meeting people face-to-face, you have to do it over Zoom and LinkedIn, work that takes a little bit more time and effort to set up meetings and things like that.


Networking is getting multiple people who want to help to get you where you’re supposed to be. – Claire Bossong Share on X


The reason why I was asking is through my research, and a couple of organizations that I belong to, is that networking is the number one way of being fortunate to get a job. Networking is the number one tip of the day now. You and I have had multiple conversations over the last couple of years. To your point, not everybody, either one, knows that networking is the best way for you to obtain a job or two, how to do networking properly. When it comes to networking, you have to make sure that you are putting out feelers to as many people as you can, and try to talk to them for 15 to 20 minutes. Is that something that you were doing?


In a couple of my classes that dealt with policy, government and things like that, we were taught how to do a coffee chat or networking chats. The coffee is going out and getting coffee with people, which I have not yet able to do in real life, but we do the coffee chats over Zoom and things like that. 10 to 15 minutes, have your questions lined up, 1 or 2 questions.


In the political field, people do not have time. If they are squeezing in the 10 to 15 minutes to meet with you, that means a lot. You’ve got to get through your question and hope that will lead you to another person who will lead you to ten more other people, and that is what networking is. It is getting someone or multiple people who want to help to get you where you are supposed to be.


You said your job fell in your lap, but your networking may have happened or helped it. How did you end up getting your job?


I was applying for jobs. I’m not getting any luck, and through the grapevine, someone had heard that I went to U of I, and I was studying for Public Policy and Law Government somewhere along that line. They called my mom, “Has your daughter had any interest in this field? We are looking for someone to fill a position as soon as possible.” I took it at the first jump I interviewed. I did not hesitate hardly at all to take it. That is people knowing or hearing about where I went to school that got me the job and the major that I was in as well.


Going to the University of Illinois did not hurt at all. In your age demographic and knowing some of your friends, have most of your friends been able to gain employment?


Most of my friends have. A few of them have completely switched the job area that they were going into. Not because it was necessarily hard to find a job in that area, but because they tried it and they did not like it. They are going back to school, or they are doing something that maybe they are not as interested in while they are trying to figure out what they want to do.


I do not know why it is that all my friends. We all eventually did find where we were supposed to be. It does not work out like that for everybody. I know there are some people that are still searching for jobs, but I have a friend who is an engineer. She works in Chicago. I do not know if that is a booming industry now. That could be, that is why she got a job. I have a few friends that are going to be teachers. They are looking for help there. It is not necessarily the hardest industry to get into now. They need the help. My friends and I have been lucky.


I graduated from U of I a long time ago. Do you have any resources or help from the university in order to get a job?


LinkedIn is the number one resource that I used while I was in college. I had no idea what that was until probably my junior or senior year, when I started looking for those jobs and internships. The University of Illinois has their own LinkedIn. You can network based on your major, class and all different things. I thought that was awesome. Even reaching out to my old professors and my mentors or my academic advisor to see if there are any other resources that they can give me, that is also networking. Those are probably the main two that I have used from U of I.


NWB 3 | Networking
Networking: It’s good to write things down and get them out there instead of just having them in your head and forgetting about something you wanted to do.


You are in the political industry. Tell me a little bit about some of the challenges that you have encountered already, and you have only been in the industry since June 2021. Have you come across any challenges as a Millennial and female in the political industry?


In the political industry, they are seeing more minority groups and more females joining the forces than they did several years ago. It is way better than it was, but it can always be better. I come from a small rural community. As far as I’m concerned, I do not think there has ever been a female representative for my district and probably the surrounding ones. That is the way it has been.


The men were the political figures back then, and it is stuck around the rural communities. My age does not help because older generations seem to think that the younger generations do not know what they are talking about, and we are ruining the political industry, let alone ruining the United States or the world, whatever they like to believe.


When I was answering the phones, trying to help people, they said, “You sound young. Do you even know what you are talking about?” I’m like, “I know what I’m talking about. I have been doing this, and this is what I studied at school.” That has been a struggle is in get people to trust me and get them to get out of that mindset that women are as capable as men in this position, and it does not take a certain person to do this job.


That is interesting that they point out that you are young. One of the things that I always recommend for younger women, no matter what their job is, if someone comments on their age, is to graze over or do not even acknowledge it, or do not even know that you necessarily have to say, “I do know what I’m talking about,” but say, “Thank you for noticing.” Graze over that if you address it or especially, do not say your age because you lose credibility, even if you have only been in your position since June 2021. They do not need to know that you have been in your position since June 2021. You need to hold down as much credibility as possible. As far as your love of politics, because that is what brought you here, what do you love about politics?


It is a never dull moment in my office, especially in Illinois. There is a lot going on. People from different states have a lot to say about Illinois. It is a progressive state. It is one of the first states to get anything done that is happening in the news right now. It is always changing. There are always new topics, bills, laws, and things that people need to get through.


I have always been interested in the government, the way it works, and the history behind it all. I’m like, “What can I do to fix that?” Eventually, someday I would love to be in the room where it happens. I love Hamilton. I got that quote from Hamilton, but I do not see a lot of young kids my age, young political-minded people that want to change for the better. My goal is, “What can I do to make the world a better place or the United States a better place than what it is or what it has been in the past few years?”


We have a lot of younger women like AOC. She is in New York. It is nice to see some women in prominent positions in the government that are opening up minds to at least expose people to other ideas and thoughts because, especially some of the older generations, sometimes are set in their ways that it is okay for someone else to have their own opinion even if you do not agree with it. You still have to be respectful of the opinion. Are there many women that are coming into the political landscape?


It is hard to say now. There are a few in Illinois that I’m seeing shift because this is an election year. There are a few women running for Senate and Congresswoman, which is awesome. I have met a few of them. The few that are in the House, I know their names right away because I’m always watching what they are doing and seeing what example they are setting for me as well as any other young girl who thinks what they are doing is awesome.


In your office or in your district, are there female mentors that you are working with? How does that work?


To understand more of the processes, constantly ask questions. – Claire Bossong Share on X


I talked to a lady about possibly getting in a group for women who like politics and the government. It is a whole year-long series. It is an all-women group, but they prefer the younger generations to get in there and learn about the things that go on in Springfield. They take us out to Washington DC and all around the state. I’m looking forward to that. There are Republican and Democratic women groups around any state that people can join. I am in a smaller town, so I do not have any direct mentorship in my field, but the group that I’m looking to be a part of and apply for is going to be awesome for me.


I was going to say pretty much anybody, and it does not matter how old you are, but especially for the younger women, it is important to have a mentor because, at this point in your career, you do not know what you do not know. I wholeheartedly believe that as a woman, I need to help those other women that are coming up behind me. It does not even necessarily have to be a woman if there are not any women in your district, but to have a mentor, especially a woman, is going to be phenomenal for you to figure out. They can teach you the ropes and especially in politics. How long is this mentorship program?


It is a whole year, and they will do different things one week in a month, that could be a couple of days of online workshops and things like that.


Along those lines, continuing education is important. I wholeheartedly believe that continuing education is one of the ways for you to open your mind and learn other things. I know you are going to be doing the mentorship program, but are there any other things that you are doing now, such as books, listening to podcasts, or anything like that, that expose you to other ideas?


I have started reading again. In between high school and college, I was reading my textbooks and things like that. I did not have time to sit down and read a book. I loved reading in high school. I have started reading a little bit different things than what I was in high school, but I do listen to a few podcasts. I have not recently because I have been busy.


There is also a community college in our district, close to my house. We get a catalog of what classes they have. There are $25 for an hour. You go in and there are History, Genealogy, how to travel for cheap, and different exciting little classes that are interesting to me that I have thought about doing. They are not necessarily a skill, but it is an exciting, different opportunity.


We are shifting a little bit to goals. Do you have written goals? Do you have a plan for your career? What have you thought about where you are going to be? Let’s not even go three years, just a year from now.


This is an election year. That is high stakes for anybody in the political world because if their representative does not get reelected, you are out of a job. We are hoping that he stays, but the districts are also changing this year with the census. More people are moving out of the state. The districts are all changing. He is moving up North.


I’m looking for opportunities up there to work for him and his new part of the district. It is a different world up North than it is in my small town. I’m looking forward to that getting familiarized with different people, even if it is an hour North of me, a new place by myself, not at home, meeting new people. That is my short-term one year where I’m hoping to be, but there are political aspirations in the next several years.


It gives you exposure to a whole other realm of individuals or situations like the city itself. That is going to be great. Do you have written goals down?


NWB 3 | Networking
Networking: Constantly network with people over meetings. Get your name out there.


I’m a big goal writer and a big planner. I’m very organized, so I love to have everything written out. I struggle sometimes if things do not go exactly how I have it written down, but that is one of the things that I’m working on is learning to adjust and adapt. It is good to have things written down and get them out there instead of having them in your head and forgetting about something that you thought you wanted to do.


People who are covering goals down are much more successful than those people that have no goals or have them in their heads swimming around. You had said something about if your representative does not get reelected, you are out of a job. Is that what you said? What is your plan B then if that happens?


I have not thought about plan B, which is bad on my part because I’m excited for him. I think he is going to do well, but nobody knows in any district and any state. I have been tossing up the idea of going to Springfield or Chicago. Those are big political hubs in the state of Illinois. I eventually went to get to DC. The pandemic has not allowed me to yet, but that would be another avenue that I have looked into as well. That was one of the avenues I was looking into while I was applying for jobs this past spring of 2021.


I do recall you and me having a conversation about you moving out to DC. We will see what happens with this pandemic. Going back to the challenges, question, and being a Millennial woman in politics, you said being young is one of the challenges. What other challenges have you encountered?


A lot of people do not understand why I enjoy where I’m at. First of all, “Illinois is corrupt. It is crazy. Why would you ever want to be put in a position where you are getting yelled at?” That is my passion. I do not question anybody else’s passion. It is what interests me, what in my brain and my body that I like about it. I like history. History is a part of government and politics. People are questioning what I’m doing and what my purpose is. That is a big challenge for me.


That is not even a challenge. The people that do not know what their purpose is, are the people that have challenges. You are lucky because you are already doing something that you love. Honestly, that is probably half the battle for everybody that is in a job. There is a statistic out there that says that 70% of people are not happy in the work that they do. They are trudging in the day in and day out, not liking their job.


There is so much time to be in a job that you do not like. That is always one of the things that I recommend is if you are looking for a job, try to focus on something that you love. You are lucky that you love politics. I understand the question from people as far as like, “What are you doing? It is politics.” If you love it, go for it. Do what you love. It does not feel like you are working because you are having fun.


In the insurance industry, 95% of people fall into the insurance. It is like, “I fell into it because of my dad or some family members in the business.” I went to U of I. My degree was in External Science, which is all insurance-based. I’m one of the few people that went to school for insurance, and I’m still in insurance. When you love it, you love it. That is fantastic. What about networks like networking in your area with Millennials? Do you do a lot of networking with your age group?


There are not many opportunities around here for that. I feel like, at least that I do not know, there is some group about an hour away that has a young professional network. They will do after-hours events, and those have been shut down due to COVID. I have not had a chance to get to those, but I know that they are canceled for the next several months. Immediately in my community, there are not many opportunities for that.


In those situations, you are going to have to come up with your way of networking with other individuals, even though it is over Zoom. You and I have never met in real life, but I hope to meet in real life once this pandemic is over. At the very least, are you trying to network via Zoom anywhere in the world?


Work smarter, not harder. There’s always a better way to do things, especially now with technology. – Claire Bossong Share on X


I have not because of the new job and getting used to things, but I’m constantly networking with people over meetings and getting my name out there. It is not necessarily my peers, but it is people in the political world or any constituents that have problems. We are having meetings, trying to figure out a bill for them, and figure out solutions that I consider that networking because they see my face, they see my name, and they are going to remember that I helped them instead of answering a phone call.


What have you done if you have a constituent that is angry and agitated? How are you as a professional conducting yourself to mitigate those situations?


I had worked for a Congressman before. I worked for my State Representative Congressman and women. They are on a much bigger scale and a state politician because the whole United States is watching them as opposed to you do not care about other states than your own. That was an interesting job. I did get yelled at a lot on the phone, and that was when I was in college.


I did not know what to say. I would usually direct them to a supervisor, but now I’m by myself in this whole office. I’m the supervisor. Luckily, my boss does not get those phone calls often. He is a great guy. He tries his best, but I have had some instances where I have to say, “I’m helping you now. I’m just the messenger. I know that you are upset. There are tightened emotions during this time, the pandemic has caused a lot to people, but we need to calm down so that I can help you as best as I can with your situation and see if I can somehow find a solution for you and with the state.”


That is a great way to put it and put them more at ease that you are trying to help them because you are the partner. It is great that you do not have another supervisor that you can rely on because that makes you be more of a problem solver. That is good because a lot of times, people run to their boss with, “I have this problem,” but they do not come up with solutions, and you almost do not have a choice. You have to come up with solutions because you are the only one there.


That is going to be a great learning curve for you because you are quickly going to realize how to put people at ease. I worked with this woman years ago. She worked with brokers and brokers sometimes brought problems and issues. Her whole idea is to kill them with kindness. The more calm you are, it de-escalates the situation. If you are doing that already, that is fantastic. How many people do you think you have to deal with on a regular basis?


We came up with a number to do a little blurb for our boss that says how many bills he wrote and how many people he has helped. This is not necessarily a people number, but it is how many cases that we have worked on and how many times we have had me on the phone. I have not been here since. It has not been all me, but my coworker, the woman before me, and me in 2021, helped 3,500 cases. It was a big number for us.


That means that you are helping 3,500 people that have problems. As I said before, you get an opportunity to problem-solve with them. I know your manager or your representative is there. Has he given you any tips on how to advance in your career or provide you with any insight on what you should be doing in your career now?


We have talked about it a little bit because he does know that someday when he is done that I could possibly be coming up and trying to take his seat, but I have not been able to go to Springfield, I think, only one time. I have not got to see anything in action, and I’m dying to go because that is right at my alley.


Once I get more of an opportunity there, he is willing to show me the processes. I do ask a lot of questions about why do you do this bill about. I’m constantly asking him questions to understand more of the processes that go into it. He is always willing to answer the questions and help me out there, but firsthand, I have not been able to see much.


NWB 3 | Networking
Networking: Asking questions is important so you will understand the big picture as to why you’re doing what you’re doing.


You are relatively new to politics. You asking questions is important because a lot of people maybe step into a position and are told, “You have to do this process.” They do the process without asking questions. When you do that, you may not understand the big picture as to why you are doing what you are doing.


Especially with a new set of eyes, you may not necessarily have to do what you have been doing because there is a better way nowadays, especially with technology and you going through U of I and me going through U of I. It is two completely different situations. I have a nephew and a sister who went to U of I. When he was going through U of I, it was funny because I got the alumni magazine, there was a picture of us at the armory, and it was all people registering.


At that time, when I was going to U of I, we had to go in person to the armory, and there were all these lines and the A through Z sign and whatever. In the picture that I was looking at when he was going to U of I, I was like, “This is the old way that we used to do it.” He was like, “It is all online now.” It is completely different. Is there a lot of technology that you are using in your position now?


I have helped out my colleague and my boss a lot with the technology side of things. It makes things easier because there were some things that they were doing before that I jumped in, and I was like, “There are many different better ways to do it.” I’m a hard worker anyway, but there is that saying, “Work smarter, not harder.”


When there is something easy that can be fixed technologically wise, that is where I stepped in and helped streamline things to make them easier. We usually use Google Docs, Google Mail, Google Sheets, and things like that. It is not a lot technology-based, but helping certain people try to figure that out to make it easier was a step for me.


I’m chuckling because when my oldest son is going to be 24 in 2021, and my daughter is going to be 21. When they were going through grade school, junior high, the whole Google Drive and all that stuff was up and coming. I was like, “You are doing what?” They had to teach me, and truth be told, my kids teach me a lot of the technology. I’m like, “Why did not you tell me I could do that on my phone?”


I wanted to point out that there is also what is called reverse mentorship. You are mentoring your boss. A lot of times, people do not realize that, I’m not going to say older, but more seasoned and tenure people can also be mentored by these younger generations that are coming up. Technologies are changing quickly. It is hard to keep up with technology.


When my kids were in junior high and high school, and I got them their first smartphone, I was trying to keep up and me tracking. After a while, I gave up because I could not keep up. I was like, “You are in high school. You figure it out. You are old enough to know what is right and wrong.” I will let you figure it out. That is a good point too because with a fresh set of eyes, you can see things completely different and mentor them. Claire, is there anything that you can think of that younger generations, and maybe even junior high or high school women, should be doing in this day and age in order to navigate the school system, college system, and get into a job?


My sister always told me that I was thinking about college way earlier than I should have been. Probably 6th or 7th grade, I was like, “U of I, that is where I’m going.” Some of my friends applied to U of I on a whim, but I was like, “This is the best school ever.” It is a big ten school. I was proud to go there. From probably sixth grade, I was in clubs as many as I could be. Few that you are interested in is a huge thing for junior high and high school women and all students to be a part of.


Get yourself involved, do something that you are interested in. It is never too early to start thinking about what you want to do. I have changed what I wanted to do since junior high to now, probably 2 or 3 times, getting interested, starting to think about what path you are going to be on and what groups or different people that you can talk to get on the right path.


Setting goals, making lists, and planning your day will help organize your work life and personal life. – Claire Bossong Share on X


The clubs helped me put a lot on my resume, especially coming from a small town where there are not a lot of opportunities. I wanted to make my resume as big as possible on my applications. Those clubs helped me out studying well. It helped me to get into U of I. You have to have good grades, but networking in high school was a big thing for me.


Getting people in the community to know who I was. I was talking to people, telling them what I wanted to do because they cared. People will ask me still now, “Are you doing politics?” I wanted to be a vet. They were like, “Are you still doing a vet?” They want to know where you are at and how you can help them or how they can help you. You just have to ask.


Those are keywords right there. You just have to ask. As a woman, one of the biggest lessons that I have learned throughout my career is that you have to ask for what you need because otherwise, how are people going to know? Sometimes you assume that people know what you need, and it is not until you verbalize it that is something happened. That is important.


Claire, this has been such a good conversation. I love that you are passionate about politics and you are in it to make a difference, not for the state but for the United States. You are going to go a long way, and I am excited to see where you are going. I am going to ask you to provide me with two actionable tips that you can recommend to our readers because my whole mission is to help women through career development. I want to make sure that we leave some actionable items to our readers. Do you have a couple of tips that you can provide?


We talked about them already. They are the ones that have got me to where I am now. We touched upon not being afraid of asking questions. If you think it is a dumb question, there is never a dumb question. Something that helps me whenever I think that is asking it in my head and playing with what I’m going to say to get it out correctly the first time, not to a point where I’m going to overthink the question, but saying, “This is how I’m going to ask it and not being afraid.”


You are holding yourself back when you do not ask any questions like we talked about and building on that. Do not be afraid to question anything. If you know you are right and something is going wrong, you have to be responsible and say something. It is an uncomfortable situation sometimes, but in my line of work, if somebody is doing something wrong that we are not supposed to be doing, I’m going to say something. It is better to say it than get somebody in trouble. That was my first one.


We also touched upon this a little bit but setting goals, making lists, and planning your day. I go to the extent of planning my whole entire day, every day. Some people cannot do that, and that is okay. I have a nice planner. It is pretty. I have stickers. It is a fun thing for me to do, but also I never forget things that I put in my planner. It helps organize your work life and your personal life. It is fun, but I do not think you can go wrong with planning in any work and any day-to-day life. When people have kids, you have to plan out appointments and things like that. Time blocking is a huge help in any industry.


This is interesting because, as far as technology is concerned, technology is fantastic and it is great, but it is constantly interrupting your day. To your point of time blocking, there is a great book that is called Deep Work by Cal Newport. He is a believer of doing focusing on one thing and shutting out everything else because you will be more productive if you sit down.


There is also another technique, the Pomodoro Technique, where you can sit down and do a timer for 25 minutes of one thing without any distractions and take a five-minute break. Those are production techniques. I have a pretty planner, and I love writing things. I’m also a list tucker and I love it when I can check something off my list. Thank you again for being here, Claire. Is there any social media handle where you hang out or anything like that?


I deleted my Twitter. I do not have Twitter. That was not good for me. It was a toxic environment, but I have my Instagram and LinkedIn, which I shared with both of you, but my Instagram now is @ClaireBoss_, and that is it.


Claire, thank you for being here. I appreciate our conversation. We’ve got some tremendous valuable tips here. Thank you very much.


Thank you.



What a valuable conversation we had with Claire. I wanted to recap her two tips. The first tip is do not be afraid to ask questions. Her second tip is do not be afraid to question anything. If you see something that does not sit quite well with you, ask why things are being done that way. Claire loves politics, and it is apparent that is her passion.


That is another thing that I want to remind you. Figure out what you love to do and see if you can find a paying job where you can use those skills that you love. There is that saying that says, “If you love what you do, you do not work a day in your life.” Seek a job where you can use the skills that you are great at and you love. From there, remember to be brave, be bold and take action. Until next time.



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About Claire Bossong

NWB 3 | NetworkingClaire Bossong is 22 and lives on a farm in a small, rural community. She attended the University of Illinois Urbana-Champaign where she studied Agricultural and Consumer Economics with a concentration in Public Policy and Law with a minor in Animal Sciences. She is currently working as a District Director for an Illinois State Representative with plans to move forward in her political career.