The BEST Career Advice From Chicago’s Leading Ladies

Today is your lucky day kids. I took the very best of Work Smarter, Not Harder (January – March) and squeezed it into one potent glass of BOSS LADY JUICE. So drink it up. It will do your body real good. Oh. And you’re welcome.

How Chicago Boss Ladies landed their current position:

1. I created my own position. Hustle hard, don’t make excuses, take risks, believe in yourself and in your choices without apology. If you do this, you will always stand out and rise above the competition. –Jessica Zweig of SimplyBe and jessicazweig.com
2. I actually started out as a Realtor for 15 years.  When the market crashed and then I went through a divorce, I realized that real estate was not where my passion was. It was time to do something I loved and could leave my signature mark with. I immediately started my blog, Eat Travel Rock, and soon after began interviewing some of the biggest names in music at the famous Joe’s Bar. I was asked to star in 2 country music videos and I hosted a show called Food Junkie: Chicago.  I realized that being on-camera was the route I wanted to take. Next, I worked on having creative control of  my own content…. And ETR TV was born.  I’ve just never had the mindset that I can’t do whatever I set my intention to.  I know that if I work hard and persevere, I can make it far in this crazy, new career in entertainment.  There have been wonderful people along the way to support me, and then some not-so-nice people.  I don’t let the latter derail me and instead stay positive. –Kelly Rizzo of Eat.Travel.Rock and regular on VH1’s Big Morning Buzz
3. I moved to Chicago in 2009 after being a morning anchor in Texas. The position I wanted got dropped because of the crashing economy. I was stuck in a new city and no job. I started my talk show to keep my demo-reel current. Within the first year of the talk show I realized this was my true calling. I LOVED TALK TV… I did real estate video on the side to fund my talk show and one day I was filming a house for a NBC employee. She introduced me to her boss and 3 months later they picked up my talk show. –Whitney Reynolds of the Whitney Reynolds Show
4. I worked in the insurance industry for seven years. I hated my career choice. I felt so depressed in this compartment of my life, it hurt my heart sometimes. “This can not be it!” I thought. I tried to get out so many times too. I applied for marketing positions, event planning opportunities, the works. But companies wouldn’t give me the time of day due to my lack of experience. I thought I was stuck in insurance forever and would never get out. Trust me, it is NEVER too late to be happy, even when you have no hope. Little did I know the blog I started 3 years out of school (for a creative outlet) would be my ticket out. But it took SEVEN years of hard work to get me to where I am today. After I gained a little following, networked my tush off and upped my content, companies began reaching out to me for projects and collaborations. It was at this point I realized I could be paid for doing what I love. –Nicole Regan of Cedar & Rush (me!)

Morning routines:

1. The first thing I do every morning is tell my husband that I love him. It’s the best way to start my day! – Jenn Lake, VP of Zapwater Public Relations and Blogger of Sharade Style

The best way to get your foot in the door of your dream job:

1. The key is to network. It’s important to genuinely be interested in the people you meet with. Don’t just set up coffee dates to get somewhere or make a new “connection.” –Katie Niemiec of Little Black Blog
2. Create your own dream job. There are no doors. Only windows. Don’t wait for someone else to call the shots on your life. –Jessica Zweig of SimplyBe and jessicazweig.com
3. Networking is paramount.  It really is ALL about who you know.  I’m a hustler and constantly making connections and pitching my ideas.  I have no fear of being told no, and I will constantly reach out to CEOs of record labels and Executive Producers of networks with my ideas.  You can’t be afraid of “no” or afraid to talk to anyone! –Kelly Rizzo of Eat.Travel.Rock and regular on VH1’s Big Morning Buzz
4. If the door doesn’t open, find the window. Nothing about my career journey is normal. Who would have thought at 23 I’d start a talk show?  And at 29, still own it, have a staff and be expanding to new markets monthly?  –Whitney Reynolds of the Whitney Reynolds Show
5. Having determination and a dream will get anyone the job they have always wanted. But networking is key! I recommend working a job in your career of choice (even if it is not your favorite position) because you learn other perspectives that will later help you in a higher up position. –Katie Schuppler founder and stylist of KS Style Consulting, Fashion Speak blog and bracelet and cuff brand Belt & Wire.
6. Doing something I love without knowing where it would take me is how I did it. But there are many paths to the same place. If you love something, submerge yourself in it. Go to events, meet people with similar interests or in that field, connect with people and become an expert on your own. I cannot tell you where it will lead you, but I promise you will figure it out with patience and consistency. It took me SEVEN years to get here. There are no shortcuts in life. –Nicole Regan of Cedar & Rush (me!)

Common mistake people make:

1. People tend to engage more with social media then in face to face conversations. – Monika Dixon, CEO and founder of Monika Dixon Public Relations
2. Being too quick to point out the faults of others! We are all imperfect and have blind spots. My greatest joy is supporting others. – Jenn Lake, VP of Zapwater Public Relations and Blogger of Sharade Style
3. Be willing to do anything asked of you when starting a new job. Wear lots of hats and never tell someone you “can’t” do something. Find a way to make it happen and you will be very valuable and successful to your employer. –Catie Keogh Emmy award winner Host and Executive Producer of NBC5’s 24/7 City Secrets
4. I am constantly receiving emails with grammatical and spelling errors, which I just naturally don’t take as seriously as ones that are typo-free. Spell check is a glorious thing.  –Jessica Schultz, 3rd grade teacher, two Master Degrees and head of several committees at Hinsdale Elementary School
5. BE PRESENT! Smile or say hi when passing someone in the office or when running errands. It makes you more visible, spreads positive energy, and may create a relationship that will benefit you in your journey to success. –Melissa Jones of TheCEOffice
6. As a blogger and even an entry level professional, I see many women playing the comparison game all to often. Whether it is comparing social media followers, to who is wearing what, to what company someone works for – everyone is always worried about what others are doing. I’ve learned how important it is to believe in my content, interests and self. Then share these with others. –Katie Niemiec of Little Black Blog
7. Being expectant. Entitlement. Thinking that success comes easy and that you don’t need to pay your dues.  Talk to anyone who has achieved a great level of success, financially or otherwise, and they will tell you it involved countless lost hours of sleep, rejection, failure, tears, immeasurable stress, fear and struggles they won’t ever talk about.  If you want to build your career, be willing to roll your sleeves up. And always, always remain grateful and humble. –Jessica Zweig of SimplyBe and jessicazweig.com
8. Not acting professionally.  It’s amazing to me how many people lack basic tenets of professionalism or courtesy.  Always respond promptly to emails or requests, always show up on time (or early) to meetings, etc.  And for the love of god, brush up on your grammar.  At least learn your pronouns and the difference between less and fewer! –Kelly Rizzo of Eat.Travel.Rock and regular on VH1’s Big Morning Buzz
9. Comparing themselves to others. There is always going to be someone smarter, taller, etc but there’s only one YOU. Don’t fall into the trap of comparison. Take stock in yourself. –Whitney Reynolds of the Whitney Reynolds Show
10. People aren’t curious enough. Every person and every place has a fascinating story. You just have to dig. I have found unlikely opportunities, connections and fascinating tidbits by asking how, why and when. Even with people I know quite well! Try it. It opens doors right in front of your face. –Nicole Regan of Cedar & Rush (me!)

How to make time for working out and staying healthy:

1. I make it a priority to workout. It relieves stress and makes me a tougher, stronger professional. – Jenn Lake, VP of Zapwater Public Relations and Blogger of Sharade Style
2. One of my favorite things in life is working out. It is my therapy so I try to work out in some form every day. I also follow a vegan lifestyle. As for cocktails, I try to keep “Drinking nights” to one or two a week. –Katie Schuppler founder and stylist of KS Style Consulting, Fashion Speak blog and bracelet and cuff brand Belt & Wire.
3. I schedule my workouts into my calendar and treat them the same way I do meetings and other appointments. –Jessica Zweig of SimplyBe and jessicazweig.com

Organizational resources:

1. One of my favorite developer blogs to read – Zoe Rooney – wrote this blog post on how she schedules projects. I’ve modified it to meet my needs but it definitely helped me budget time and steps with clients.  –Lindsay Humes, CEO & Founder of White Oak Creative
2. LISTS. I have lists everywhere. –Jessica Schultz, 3rd grade teacher, two Master Degrees and head of several committees at Hinsdale Elementary School
3. My favorite resources for staying organized include the following:1.) Evernote – My favorite app for projects. It syncs between your desktop, the web, and your mobile device so it is easy to file away any article, email, photo, or note into a folder for future reference. I then tag each file so when I do a search later it will pull all notes for that subject. Melissa Jones of TheCEOffice
   2.) Wunderlist – My favorite app for lists. I’m a list person and this app contains lists you can create for groceries, fall fashion, spring fashion, goals, gift ideas, places in Chicago to visit, etc. It syncs with the web and your mobile devices.
   3.) Whitney English Day Designer – She is a designer from Oklahoma and I have used her planner for 2 years. It’s heavy duty, but I love that each day includes a quote, gratitude section, and top three goals to achieve.
4. My best tips this year are:
   1.) Emily Ley Simplified Planner: This planner has changed my life. Its more of a lifestyle, rather than the planner. It’s so pretty and I love how Emily shows you how to use your planner in the beginning of the book. They sell out online but I found mine at Magnificent Milestones in Chicago.
   2.) Drugstore.com: I am terrible at remembering to purchase toothpaste, laundry detergent, cleaning supplies and other home goods. These little things can set you back significantly (laundry mountains, late night runs to the grocery store, nothing to wear, etc.). To conquer this set back, I setup an automatic monthly shipment to be delivered right to my door step. Life saver for me! –Nicole Regan of Cedar & Rush (me!)

Best advice:

1. Do not check your social media every hour! You will not be able to accomplish anything else. – Monika Dixon, CEO and founder of Monika Dixon Public Relations
2. Don’t let email suck you in. I am guilty of this sometimes. I could literally spend all day replying to emails as they come in – and then I don’t get any projects done. Check email a few times a day but don’t sit on it all day long. – Kit Graham of the Windy City Blogger Collective and The Kittchen, contributor to Coca Cola and author of The Gourmet Grilled Cheese Cookbook
3. Stress is something you put on yourself. My boyfriend said that to me all the time and it finally started to sink in. Once I identified and managed things that were causing me to stress, I got a lot more enjoyment out of my day-to-day. Nothing good came from talking about “being stressed” or “being busy”. –Lindsay Humes, CEO & Founder of White Oak Creative
4. Be authentic, kind and humble. Those qualities are invaluable – the ultimate gems. The moment you lose them, you’re just another bauble in the box. – Jenn Lake, VP of Zapwater Public Relations and Blogger of Sharade Style
5. Be kind, treat others how you would like to be treated, laugh a lot, smile more, take yoga and drink wine so you can do the splits when you are 70.  –Catie Keogh Emmy award winner Host and Executive Producer of NBC5’s 24/7 City Secrets
6. Goal set. You are your own best motivator! Whether my own goals are long-term (Jessica, go for that second Masters degree) or short-term (Jessica, finish grading those essays tonight so you can go out for a glass of wine with the girls tomorrow), I am constantly setting benchmarks and goals for myself. I function more effectively when I have a dangling carrot in front of me and something new to work toward. Goal setting helps me continue to grow both personally and professionally. –Jessica Schultz, 3rd grade teacher, two Master Degrees and head of several committees at Hinsdale Elementary School
7. You are the sum of those surrounding you. Choose your friends and associates wisely. Don’t participate in gossip. Associate with those that you can learn from and those that will push you to do better. –Melissa Jones of TheCEOffice
8. I think the biggest saying I’ve taken away from my experiences thus far, is everything happens for a reason. We might not understand it in the moment, but there is always a reason and a way that will make us more satisfied in the end.  –Katie Niemiec of Little Black Blog
9. Constantly educate yourself.  I recently got asked to create a Use Case for a technology roadmap for this global program I’m helping build. I had never heard of a ‘Use Case’ in my life and I’m not a techie in the slightest. But, instead of panicking and passing off the project to someone else, I spent three hours on Google teaching myself Use Cases. The Internet is the new MBA. There are incredible digital courses, programs, workshops, webinars, TedTalks and YouTube videos available on anything you crave to learn about. Read books. Attend lectures. Hang around people who are smarter than you. Don’t say: “I don’t know.” Say: “I don’t know yet.” And then ask questions, take action and assume some humility so you can grow. The moral of this story…when I presented my Use Case to the head of the IT department, she told me it was one of the best Use Cases she’d ever seen. Who knew? I certainly didn’t! Know that you don’t know everything, you never will, and constantly be open to learning. –Jessica Zweig of SimplyBe and jessicazweig.com
10. Be yourself.  I’ve become so much more liberated once I just decided that I need to be me.  Now life is a blast when I can just show the world my fun and silly side along with my professional and hardworking side.  I’ve stopped apologizing for doing what I want in my career. You should only surround yourself with people who share your vision and are supportive. –Kelly Rizzo of Eat.Travel.Rock and regular on VH1’s Big Morning Buzz
11. Being from the south, my grandmother’s motto was be sweeter than the tea you drink. Chicago is a big/ small town. Always be nice! –Whitney Reynolds of the Whitney Reynolds Show
12. Network, network, network. Meeting new people and asking them questions help you grow. No need to learn the hard way when you can ask the experts. If you don’t know anyone (like I did), go out there and meet people. Get uncomfortable. It will be awkward but get over it. Introduce others. Email a compliment or write a thank you note. Like I said, you will find opportunities or advice in the unlikeliest of places. If done genuinely, it’s an effective way to differentiate yourself. –Nicole Regan of Cedar & Rush (me!)

How to conquer your inbox:

1. It’s all about prioritizing. I pay attention to emails from clients first. Those get most of my attention. My goal is to be easy to work with and I think that the number one key to being easy to work with is to be responsive. I never let an email from a client, or potential client, sit for more than half a day. If a client emails to say they want holiday content, I might just email to say that they can count me in, that I would love to take on the project, and that I will pitch specific ideas later – this way they hear back from me right away, but I have a little more time to flush out my ideas. – Kit Graham of the Windy City Blogger Collective and The Kittchen, contributor to Coca Cola and author of The Gourmet Grilled Cheese Cookbook
2. My inbox is kind of a like a to-do list. I’ve always viewed it like that. I keep my folders very organized (Admin, Clients, Financial, Premades, New Clients) and the subject lines to emails I send out. I also only work with two emails – a personal and a work one. I check email three times a day – morning, mid-day, and evening. I usually check it when I also need to write emails to clients on work I’ve completed. I used to check email throughout the day but I wasn’t getting as much done. –Lindsay Humes, CEO & Founder of White Oak Creative
3. I follow the File. Act. Trash system. 1.) As I open each email, I decide if I can respond to it immediately or not. If I can respond within 2 minutes, I do so immediately then file it away. I use folders a lot since I am a CYA lady. 2.) The emails that I can’t respond to immediately and require action I add a reminder flag that is a couple days prior to the due date. Then I categorize by project/subject. 3.)Then depending on the priority of a project/subject I will go back and filter my emails so that I only see emails that relate to that specific project and work through them. This really helps me stay organized and complete projects on time. –Melissa Jones of TheCEOffice
4. I’m currently reading Lara Casey’s book, Make It Happen, where I learned this tip about emails. She brings up the idea that if people see my emails coming in late at night or early in the morning, they will continue to converse at those times thinking I will always be available. Stopping at a certain point in the night definitely helps alleviate the unbalanced feeling that can bring. –Katie Niemiec of Little Black Blog
5. File, file, delete. Repeat.  I strive to keep it under 50. –Jessica Zweig of SimplyBe and jessicazweig.com
6. Folders! I have organize my inbox in a very special way. I tend to bcc myself on things that need to be followed up on or have a hard deadline. –Whitney Reynolds of the Whitney Reynolds Show
7. Game Changers: 1.) Automatic responder: Unfortunately I cannot and will not get to every email. I think this should be a last resort but it works for me. Saying I won’t get back with people upfront eliminates expectation and disappointment. Feel free to send me a blank email at cedarandrush@gmail.com to see what mine says! 2.) Unroll.Me: Unsubscribe from all email distribution lists in one click of a button. An AWESOME way to de-clutter and significantly decrease your email volume. You will be surprised how many emails you are subscribed to! 3.) Canned responses. If you find yourself writing the same thing over and over again, save it! I use Gmail and this trick saves me hours of response time. Even for personal emails! {Ex. “I would love to but I have plans that day” or “thanks for reaching out, let me get back with you”}. –Nicole Regan of Cedar & Rush (me!)

How to format emails:

1. I believe you can collect more bees with honey than vinegar. I always try to be pleasant but to the point. –Catie Keogh Emmy award winner Host and Executive Producer of NBC5’s 24/7 City Secrets
2. My 3 best tips are: 1.) I format my emails depending on the purpose of the email and who the recipient is. 2.) New business contact/acquaintance – warm greeting, action needed, warm closing. 3.) Business colleague/ongoing business partner – straight to the point. 4.) I prefer polite, direct emails. We all have a lot on our plates and I try to be conscious of others time. You want to make it as easy for the recipient as possible. This may mean including additional relevant details so there is not time wasted sending emails back and forth. –Melissa Jones of TheCEOffice
3. I just downloaded the Gmail app, Streak. It tracks your emails and lets you know if the recipient has seen or opened it yet. This is the best thing since sliced bread, people. You can bet when someone doesn’t respond and I know they saw it – I definitely follow up! –Katie Niemiec of Little Black Blog

Keeping an organized workspace:

1. Only make accessible what you use everyday. If you don’t use it everyday, don’t have it out.
   –Lindsay Humes, CEO & Founder of White Oak Creative
2. I always say if your desk is a mess, chances are that you are too. I recommend sorting your desk at the end of the day; it’s a great way to ensure a smooth start for the next. Also, invest in colorful, fun organization pieces (e.g. planners, staplers, folders, etc.). – Jenn Lake, VP of Zapwater Public Relations and Blogger of Sharade Style
3. Organization is definitely my strong suit. (Nicole and I were roommates in college and we won the “cleanest room” award in our sorority house sophomore year.) My biggest organizational tip is to simplify and minimize as much as possible. I try to go through my desk at work or closet at home a few times a year to purge and declutter. Once I am left with only the things I absolutely need, it is much easier to keep them organized–everything has its place. –Jessica Schultz, 3rd grade teacher, two Master Degrees and head of several committees at Hinsdale Elementary School
4. I think it’s most important to create a workspace that feels good to you. Go for positive energy over tidiness. –Jessica Zweig of SimplyBe and jessicazweig.com
5. Clean once a week. I go through my office and throw out old papers and do a one over weekly. I like fresh flowers on my desk, they help me stay inspired and I always have classical music playing. –Whitney Reynolds of the Whitney Reynolds Show

Favorites

Websites: PRWeek, Mashable,  PR Newser, The New Potato, Etsy, Lynda.com, Garance Dore, Fast Company, The Everygirl (2), WWD, CoolHunting, Thrillist, DNA Chicago, The Daily Skimm (2), Entrepreneur.com, Inc.com, GalaDarling.com, SheTakesOnTheWorld.com, TechCrunch.com, MindBodyGreen.com, DanielleLaPorte.com, TheDailyLove.com, AlexandraFranzen.com, Accessory Mercado, Influential Gal, Corals and Cognacs, Cup of Jo, Google Analytics, ShopBop.
Favorite Apps: Instagram (5), #nocrop, UberNewsstand, Uncrate, AfterLight (3), Buffer App, Uber, HouseSeven, Netflix, Dark Sky Google Maps, Popular Pays, FaceTune, SnapChat, Angel Numbers by Doreen Virtue, Shazam, Eater, Grubhub, GateGuru, FlightAware, Rhapsody, Pandora, Chicago Parking, Starbucks, Daily Quote, Snapchat, Snapseed, VSCO cam, Classpass.

Favorite Books: Setting the Table by Danny Meyer; Think Like a Freak by Steven D.Levitt & Stephen J.Dubner; The Tipping Point by Malcolm Gladwell (twice), Yes, Please by Amy Poehler, Bossy Pants by Tina Fey, Daring Greatly, How to Become CEO, Love & Respect, Make it Happen by Lara Casey, The Desire Map by Danielle LaPorte, Contagious by Jonah Berger, Launch by Jeff Walker, Growing into Grace by Mastin Kipp, GIRLBOSS by Sophia Amaruso, Master the Money Game by Tony Robbins and my favorite fiction book of all time is The Kite Runner, Cockpit Confidential– Patrick Smith,  Restaurant Man– Joe Bastianich, Medium Raw– Anthony Bourdain,  anything by Lee Strobel, Quest Study Bible, Etiquette by Emily Post, Southern Living Magazine, The Four Hour Work Week, The Happiness Project.

Favorite Resources: Cision, Radian6, Publicity Club of Chicago, The Business of Being Creative, Think Splendid, Feedly, Ms. Tech, YouTube, SocialTriggers.com, Simon Sinek, StartWithWhy.com, Eater, Rolling Stone, Wikipedia, drugstore.com; The Well, Savvy Business Owners {where entrepreneurs can freely and openly ask questions or seek advice. It’s awesome and anyone can join!}

Favorite Programs: Adobe Echosign (for signing documents), Microsoft Outlook, PowerPoint, Excel, Adobe Lightroom, Spotify, Photoshop, Streak, B-School, Blog That Converts by Derek Halpern, Reel Marketing Insider by James Wedmore, Blogstomp.

Favorite Resources: PowerSheets, Well Designed Year

Any tips or advice that stick out to you? Share your favorites below! Or share your own favorite tricks so we can all learn from each other.