Career Change: Taking the First Step

When it comes to your career, you may get to a point where you’re not sure what the next step is. How do you figure it out? In this week’s episode, we talk about how I took my first step to a career change in hopes this episode helps you prepare for your next step!

It’s now been a couple months since I’ve had a job and I have to say I’m starting to allow myself to enjoy it a little bit. But a big part of that is because I know this is a temporary situation. As part of my journey to figure out what’s next in my career, I’ve hired a career coach to help me figure out my options not only within the advertising field, but potential other career paths my skills would translate. So if you’ve ever had a difficult time figuring out what’s next and didn’t know where to start, or considered hiring a career coach, then this one’s for you! Let’s dive in. 

Overcoming the Guilt

First I have to admit, it feels great to not be working right now. Sorry, not sorry. I’ve been consistently working since I was fifteen years old. I took one semester off my first year of college, but other than that, I’ve consistently had a job. I never took time after college. I never took a sabbatical. So here I am, eighteen years into my career taking a much needed break. 

At first, because I was laid off and not expecting this break, I had a lot of guilt. Guilt for not having a paycheck coming in because like many elder Millennials, my Boomer parents always instilled in me the importance of earning a steady paycheck. Guilt for putting that added burden on my husband because while he has been super supportive, I’ve also been financially independent since I was twenty-one years old and depending on another makes me uncomfortable. And one of the most surprising feeling, guilt for having free time. 

I’ve long been aware that our culture is one that celebrates being “busy”. It’s like this constant competition, who can be more busy. People love to share how busy they are too. They wear it like a badge of honor. Having free time is considered a luxury. Someone that has too much free time is considered lazy. So now that I’m not working, I obviously have more free time. Yes, this podcast takes up at least one to two days a week of “work hours”, but other than that, my time is my own. 

At first, I kept myself as busy as a job would. Even though I wasn’t clocking in and out, I was finding enough to do to keep myself busy for the whole day. Whether it was researching things for the baby, planning our anniversary weekend, running errands or cooking – I would wake up at around 7:30am and was busy until dinnertime. The weather started getting nicer and I realized that most days I wasn’t even leaving the house other than to walk my French bulldog Ginza. 

Allowing Myself Joy

In a conversation with Christian one night, he told me that I needed to enjoy my summer. And  you know what? He was right! Not only had I never just taken time off, but this would be the last time I didn’t really have a lot of responsibility before the baby came. When would be the next time I would be able to just wake up whenever I wanted, and do what I wanted for a summer? Next summer, we’ll have an amazing little girl. I’ll be working again. I’ll have to create a schedule around the needs of others. But right now? Right now my time is still my time. The weather is finally nice, and I can spend my days how I want to – not how I have to. Christian was right, I should take advantage of this time! 

First thing I started doing was to stop the internal self-talk that I “should be doing something”. Instead, I thought about my week in four chunks. Morning, Afternoon, Night and Weekend. The reality is I’m the only one I know that isn’t working so the reality is during the day, it’s not like I can call up a friend and go do something. But that didn’t mean I couldn’t have fun. 

So during the morning, I would be productive. This includes my workouts, which I’m still keeping up with six days a week well into my second trimester thank you very much. I even signed up for the July challenge at my pilates studio to do ten workouts in a month. That doesn’t sound like a lot, but pilates on reformer machines is no joke, especially pregnant, so four weeks of 2-3 classes really exhausts your muscles. Outside of pilates, I do Peloton cardio classes, mostly bike, or outdoor power-walking. After my workout, I spend the rest of the morning getting shit done. Some mornings this means writing a podcast episode or recording one. Some this means going grocery shopping, doing laundry or running errands. Whatever needs to be done, I do this in the morning. I actually have quite the morning routine at this point, wake up, feed Ginza, have a protein smoothie, workout, shower, eat breakfast, get shit done until lunch. 

After lunch, I use the rest of the afternoon to do something fun. One day I took Ginza to Montrose dog beach. She loves the beach. Not really going in the water, but sticking her feet in and sitting on the towel and watching other dogs. She’s a July baby, so I get it. I love the beach too. One day I went kayaking on the Chicago river, against Christian’s wishes. He was concerned I was going to fall in but who falls in? I am really. Especially on the kayaks you rent. They’’re made for beginners and are very stable. And I wouldn’t consider myself a beginner kayak. I know how to maneuver and have kayaked a lot – including multiple times on the Chicago river. I have to say if you are a beginner, the Chicago river isn’t really where I’d start. It is more difficult than your typical calm lake. You have lots of boat traffic and currents to deal with and can be challenging for a beginner. But will they fall in? Most likely not. You’d have to stand up to fall in for the most part and if you’re standing up on a kayak, then you deserve to get wet. Sorry. 

One day I just took Ginza to a park and sat in the shade, read a book and threw her a frisbee for the afternoon. It was lovely. And I’ve started to own my free time. I don’t feel bad for having it anymore and there are no apologies if I want to spend my morning watching Wimbledon because why not? I can. I’m going to take full advantage of this time I have left where I’m not yet a mother with all that responsibility and I can just have fun! Well, as much fun you can have in the summer without drinking. 

Defining on my future needs

Part of my todos during this time is trying to figure out what the heck is next for my career. As part of collecting unemployment, I have to apply for jobs every week. So I am looking at jobs on LinkedIn and job boards, but nothing is really standing out to me. There are some interesting options, but I’m just not sure what is next. Maybe that’s because I know I’m not currently looking to start a new job before the baby comes, so maybe I’m just not in the headspace. Maybe it’s because I’m still recovering from burnout. Maybe it’s because I just am not sure if I want to stay in advertising, or I’m curious about what else is out there. 

With all this uncertainty, the one thing I am sure of is what I want out of my next role when I go back. I’ve been thinking about it a lot over the last couple months because unlike other jobs I’ve taken, this next role will have an impact on more than just me and Christian. When I go back to work, hopefully in February or March, we’ll have our baby girl to think about. To be clear, I don’t mean that I want to take a role that is part-time or not at a demotion because I’ll be a new mom. I’ve worked really hard to get where I’m at and build my skillset to where it is. It isn’t fair to me to go backwards because I chose to have a child. 

If I stay in advertising, I know the drill. Advertising isn’t a nine-to-five job. I will have to work weekends. I will have to work nights. I will have some travel involved. All of these instances mean that, like a lot of working moms, there will be times when I will miss something. I will disappoint her. She will be upset with me at some point for missing something. 

Hopefully I can be like mom my in this sense. My mom was a working mom and while she did miss some things, it seemed like she was always there for the times that mattered. I was a busy kid. I was always playing some sport and therefore if my parents were working, it was very hard for them to be at every single thing. Take my cheerleading competitions for example. Cheerleading is not only a sport for your kids, it’s a lifestyle. It takes a lot of time out of the day. On competition days alone, I’d be up before the sun came up. I’d head to a teammate’s house where the moms would all be doing our hair in a specific way. Because in competition, we all had to be the exact same. Same hairdo, socks the same way, shoes the same. If anything was different, we would get points deducted. 

My mom usually wasn’t the one to take me to my cheerleading competitions. That was usually my dad. So he’d wake up, take me to the house and sit there, engrossed in a cloud of hairspray, for hours waiting to even go to the competition. When we were all ready, we’d head to some gymnasium where our parents would have to wait around in uncomfortable bleachers pretty much all day waiting for our three minute performance. Then they had to wait around for additional hours for the trophy ceremony. Don’t worry, there were refreshments they could purchase – like half cold hotdogs, chips and pop sold by some students. While I’m sure there were a million things these parents could think of to do other than spend an entire Saturday in a stuffy gymnasium with techno music blasting and cheerleaders screaming for eight to ten hours, in a way, I think my dad liked it. 

Almost all of the parents were women. Maybe the other dads figured out a way to get out of this responsibility, I’m not sure. I’m sure they thought of something – like the lawn needed to be cut or some other typically masculine chore his wife had been up his ass about doing but he waited until it enabled him to get out of a worse fate for him to oblige. With the lack of testosterone in the gym, my dad pretty much the most popular kid in school, surrounded by women just hanging on his every word. They all just thought he was the best dad around, probably because they couldn’t get their husband to come. So for them to see a man here instead of his wife, well that was something special. You mix this along with the fact my dad has the uncanny ability to make friends with literally anyone – and he turned these eight to ten hours of a competitive cheerleading competition into his own campaign for world’s number one dad. Now that I’m going to be a parent, I think they could have treated our parents better at these competitions. If you’re going to have refreshments, can they also have some healthy options? Could they get a bloody mary or a mimosa or something? If my daughter chooses cheerleading, I hope this much has changed at least. 

While I mom may have missed a lot of my cheerleading competitions, she never missed a birthday or a graduation or some other even that I felt was critical to her being there. I don’t look back at her absence as a negative, like my brother. He still holds it against her. As I look ahead, I started to wonder why I didn’t have the same reaction. And then I remember “take your kid to work day”. Remember those? When you’d go to your parent’s job? My mom was an interior designer for Walter E Smithe, a well-known, high end, local custom furniture store in the Chicagoland area. I loved going to her “take you kid to work day”. They’d always have activities for us to do like coloring contests or one time they even had an animal petting situation in the parking lot where we held a boa constructor and had a tarantula crawl up our leg (if we wanted to). But most of all, I loved sitting in her office watching her work. While it could be boring, and I’m sure I complained, I loved seeing her be so important to other people. Her phone ringing or people stopping by to ask her questions. Her books of fabrics and textiles laying all around as she helped a client. Plus, the elegance she possessed while doing all of this. My mom has always been quite fashionable and beautiful. You could tell others around her thought so as she commanded every room she walked into. That was my mom. Powerful, smart, accomplished, elegant and inspiring to this young girl. 

Yeah, maybe she missed sitting in bleachers all day to see my performance. She would always watch the VHS of it later that my dad recorded. It wasn’t that she wasn’t interested, but her whole life didn’t revolve solely around us kids. And I don’t say that in a bad way at all. She had her career and also her hobbies like playing soccer with friends in an over forty league. Which seemed so old at the time. I was like – how are these old women running around playing soccer? Now that I’m approaching the big four-zero, I realize that of course they could play soccer! They’re so young! 

This admiration I felt watching my mom work is what I want for my daughter. Maybe I won’t be there for everything. But I will be there when it counts. In the meantime, I want her to see me living a fulfilled life. I want her to see me with my own hobbies, with a career I love and with a social network that supports me. Because I want the same thing for her when she’s older. 

I may not know what my next title will be, but I know I have some requirements. I want a role that excites me. If I’m going to spend eight plus hours a day away from my baby girl, I want a role that fulfills a different part of me. That allows me to be creative. That challenges my mind on a daily basis. That continues to force me to grow and evolve. And a role that helps me gain new perspective. I want increased flexibility and some control over my schedule so I never have to miss something that’s really important to her. Ideally, I’d like a hybrid work environment so I can be home some days when she gets home from school but other days I can connect with colleagues in the office. I don’t mind some travel, but probably not more than 30% to ensure I am not gone for too long of stretches but I get my airline status so our family vacations are more enjoyable at the airport. Above all, I want to be passionate about my role so when I do disappoint her, she sees that I’m not missing it for some miserable job where I’m just there for the paycheck. 

Enlisting a Career Coach

This next step feels more than just another role. It needs to be something that will make the mommy guilt worth it. It very well could be in advertising, but maybe it’s not. As I scrolled through job listings, nothing was really jumping out at me and I realized that I may need some outside help to figure out where to go next. I had spoken to some colleagues in the business but most of their advice was either to convince me to work with them again or another aspect of advertising. And maybe that is where I’ll end up. But what if this is an opportunity to start something completely new? I only know what I know – and that’s advertising. But I can’t imagine my skills don’t translate elsewhere. 

I decided to enlist a career coach to help me navigate this next chapter in hopes of getting clarity to help focus my search when I’m ready but also to give me perspective outside my industry on potential opportunities. I did some research and selected a firm in Chicago that is female owned and has a very good reputation. I elected a package that includes me taking a three hour evaluation test called “Highlands Ability Battery” and then you meet with a coach to walk through your results, opportunities etc. 

From there, I’ll work with a professional resume writer that will help get my resume noticed, focus it for the best possible outcome and help with my LinkedIn profile and cover letter to highlight my strengths for the roles I’m interested in. I realized that I’ve never really had practice with my resume and cover letter writing. Every role I’ve had has come from those reaching out to me. I’ve never gotten a job from submitting a resume. Therefore I’ve also never had to adjust my resume and cover letter for a particular role. At this point in my career, I realize it’s important for me to highlight my skills in a way that stands out within my competitive set. This will be even more important if I shift away from advertising as I’ll have to translate my skills to be relevant for the role. 

My goal is to work with the career coach and resume writer in the summer and early fall before the baby comes in mid-October (if she’s not early). Then I can focus on the little one through the holidays and in January start to use my new resume and knowledge of what roles I want to go after to enter the marketplace. My hope is to get back to work mid-February or March which would give me the full three month maternity leave I would have expected from a role. It also would mean I would be without a role for almost a year. Wow, how time flies! I can imagine I’ll be ready to get back to a normal adult life by then!

Taking that first step

Taking this time for myself allows me to enjoy the last summer before motherhood in a way I never thought I’d be able to. I can focus on myself and my needs above all else for one more summer before I have a child to look after. It also gives me the headspace to really figure out what I want to do next. I realize my privilege in being able to hire an outside party to help me take this first step, and I’m so thankful for that. I think it will really help me build the confidence I need to take that next step. The confidence that it’s not only the right role for me, but for my family. What better time to do that then now? When I have the time and when I have probably the lowest level of stress I’ve ever had in my adulthood life. I may not have the answers yet, but it feels great to have taken that first step to figuring it out. 

So now it’s your turn? What can you do today to help you start to figure out your next step? Is it hiring a career coach? Is it considering what about your role you love and looking for roles that offer those same aspects? Is it reaching out to colleagues and getting a better sense of available opportunities? Whatever your next step is, take some time to consider what you want in a role. What qualities will make you happy? What do you need to make it all worth it?  

Thank you so much for joining me today. Please rate and review this podcast on Apple Podcasts. Join me on my social channels to get more content and inspiration. You can follow My Almost Midlife Crisis on TikTok, Instagram, Facebook and Twitter. You can also check out my new YouTube channel with videos of the episodes and shorts to keep you entertained all week. Subscribe wherever you get your podcasts to make sure you are always up to date on the latest episodes and sign up to get the written transcripts delivered right to your inbox at 

Until next time!

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