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  • Michelle Mekky

5 Signs It's Time to Fly Solo

Updated: Mar 20


Real talk: entrepreneurship isn’t for everyone.


It’s become trendy in recent years, but the truth is it’s incredibly difficult. There are no guarantees. It requires sacrifice and heartache. I always warn friends who are considering a career in entrepreneurship of the difficulties that lie ahead.


That said, if you’ve got an entrepreneurial spirit, it will be the best thing you ever do.


I didn’t grow up thinking I wanted to start my own company. I’ve explored several career paths in my life, but I never thought I wanted to be an entrepreneur. I first thought I wanted to be a reporter, then I explored being a television anchor, and then I wanted to work in PR. I never quite imagined running my own agency until I was somewhat forced into it—like a calling. I woke up one day and realized I was a veteran in the industry. It took me years to gain the experience necessary to realize what was missing in traditional PR, and to gain the confidence to fill those holes myself, but once I was ready, I just knew.


Today, I truly love my job. I have so much fun working with clients and gaining publicity for them. There’s a reason entrepreneurship is trendy. As an entrepreneur, you are incredibly powerful. You can create anything. Your decisions and your time are entirely your own. But that reality is scary, too, and I personally wouldn’t have been equipped for this job even five years ago. At the end of the day, anyone can be an entrepreneur, but that doesn’t mean everyone should be.


Are you thinking of going off on your own? Here are five signs it might be right for you:

  1. You’ve achieved all you can at your current company. A sure sign you’re ready to move on is when you don’t see any clear paths for growth in your current position. When you’ve accomplished all you can and you can’t imagine where you’re going to go next. I spent years as the second-in-command at various companies. I always felt content as the number two—or rather, I thought I was content. A turning point for me was realizing that I wasn’t energized by the idea of becoming number one at that particular company. I felt I had done it all. Deep down, I knew there was truly nothing more to achieve there. I had hit the glass ceiling, so to speak.

  2. You aren’t excited about moving on to any of your competitors. Sure, you’re ready to move on. But should you start looking for another job in the same industry? If you’re not excited by the prospect of working for any of your competitors, it’s a good indicator you should move on. I had a pretty good sense of who the other major players in the industry were, and even though I was very curious to see how they run their businesses, I was more excited at the thought of seeing what I could do on my own. I always have respect for anyone in my industry who runs a business and is successful at it. I am actually in awe of those before me who have grown to sizes I can’t even fathom. But I was itching to see if I could really do it.

  3. You’re a veteran in the industry. There are plenty of successful entrepreneurs who aren’t veterans in their respective fields. But in my case, waking up and realizing I was one of the most experienced members of the PR industry gave me the confidence I needed to know I could thrive on my own. I knew the industry inside and out. Others respected me. I knew I could build something great.

  4. You want to create your own thing. This is the mark of anyone with a true entrepreneurial spirit. If you’re experienced and creative enough to come up with innovative solutions to pain points in the market, and no one is solving them, you’ve got a good foundation for your business. The key here, though, is that your ideas aren’t being received at your current company. No matter how often you bring them up, they aren’t being taken into consideration. If you think it’s time to create your own thing, then do it.

  5. You’re open to encouragement. Listen to those who know you best. They see things that you’re unable to see in yourself. My friends, family, mentors, and mentees all told me that I needed to start my own business. A moment I’ll never forget is when I got lunch with one of my mentees, who had started her own incredibly successful agency in her 20s. She told me that I was a major reason she had had the guts to do that. It was an eye-opening moment for me that perhaps I knew more than I thought I did. I didn’t have the confidence to believe them at first, but when I started to have the inkling of desire to go off on my own, I thought back to all those times others had seen the magic in me, and decided to take the leap.

Ultimately, if your heart is telling you to go off on your own, you won’t be able to logic your way out of it. The ultimate indicator that you’re ready to go solo is that you can’t stop thinking about it. In hindsight, I think I was destined to become an entrepreneur. I was always the hardest working person wherever I worked - and you have to have that fire to be an entrepreneur. You have to have passion that goes beyond the typical person. I couldn’t stop thinking about what I would do differently for years. What would I do if I was the CEO? How could we have served this client better? Would I have the answers? For me, going off on my own wasn’t random or out of the blue, I just finally listened to those obsessive thoughts. And finally believed in myself.


The reason entrepreneurship is so scary is because it feels like there is no safety net. But here’s the secret: there is.


That safety net is you. When you’re ready to trust yourself entirely, going off on your own will be the most rewarding thing you’ll ever do.

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2020 Silver Trumpet Award Business to Consumer, Joe's Imports Opening
2020 Silver Trumpet Award Non-Profit, ​Komen Chicago ​Race for the Cure​ Campaign​

2020 Stevie® Award Winner for Agency of the Year

2020 Agency Elite Top 100

2020 National Bulldog PR Awards, Komen Chicago Race for the Cure Campaign

2020 Official Member of the Forbes Agency Council

2020 IPRN (International PR Network) Member

2020 Expertise, Best PR Firms in Chicago

2019 Golden Trumpet Award Winner for Media Relations (Abt Electronics)

2019 Golden Trumpet Award Winner for Advocacy (Komen Chicago)

2019 National Business Enterprise (WBENC) Certified 

2018 Stevie® Award Winner for Women in Business, Entrepreneur of the Year

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