I was 5 years out of college, content with my job, satisfied with the money I was making, passionate enough about the career path I chose, but something felt like it was missing. All the ingredients were in the mix but the recipe just wasn't tasting right. I was hungry for more. I had an itch, an uncontrollable one. I knew I was meant for something else. What? I wasn't so sure.
I was working for a large apparel manufacturing company in NYC, my fourth job in the fashion industry since graduation, when my boss and my greatest mentor (I've had a few) took it upon herself to ask me some pretty profound questions about what I wanted out of life, not just my career. She encouraged me to hone in on one thing that I wanted to focus my energy on and challenged me to define my "why".
This whole concept of finding my "one thing" and thinking bigger about my purpose had me starving for answers. ONE THING? I can't even decide what to eat when I am literally starving. How am I supposed to pick one thing to focus my whole being on? What was worse than not being sure of the answer was being sure of what the answer was not. I felt like I should have been thinking, "I want to fill your role one day" or "I want to be promoted and have a powerful title". Neither of those were the things I was coming up with. I had something different in mind and I was more worried about "how" I was going to redirect my path.
For the first time in my life, I had to accept I didn't have all the answers. I knew two things; I did not want to continue in the direction I was headed and the voice inside me saying, "just go for it" would not shut up.
The only thing that made me more uncomfortable than admitting it to her, was admitting it to myself. But, I had to do something about it.
So, I started my very own business plan in the spring of 2017 and by the fall I debuted Island to East Side on November 10th, launch party and all, hosted by my best friend and her mom. I truly had absolutely no idea where this would go and how fast, but I believed it was going somewhere.
For almost 2 full years, I was working full time (in a very fast paced and high stress environment), building the ITES brand on nights and weekends, all while managing my hectic personal and social lifestyle. I finally left my job in September 2019 to pursue entrepreneurship full time. But getting there was no easy task.
I was trying to focus all my energy on my new venture, but I still had to manage that thing called my job which was becoming a daily energy suck. My relationship with my job was like a bad, toxic boyfriend. We had so much history, it made me really happy sometimes, but really sad other times. I would try to leave, but then something would happen and it would reel me back in. When it was good it was great, when it was bad it was miserable. But I accepted it for what it was - the good and the bad - and all along it helped me grow as a person. Come on, doesn't that sound exactly like that ex we all have?
Also like most relationships there's never a "right time" for anything. For example, when is the "right time" to move in together, get engaged, buy a house, or get married. It literally doesn't exist. Well neither does the "right time" to take a huge risk and leap of faith. You kind of just have to roll with it.
My close friends, family and fiancé would always ask, "What are you doing? When are you leaving your job?". I had no answers for them but I would fantasize about the day I quit nonstop. I guess that's why they say to be careful what you wish for because once I got to the point of it being realistic for me to run Island to East Side full time, I was scared sh*tless. Would I regret leaving? Would I want my job back? Would I be able to support myself? Would the business sustain itself? Would my lifestyle have to change? All of these questions filled my head for months on end.
Once I accepted I didn't have a crystal ball and neither did the 1254753 people I consulted with on this matter, I realized I would never know the answers to these questions unless I tried. I knew I had to quit to grow. Not only to grow my business, but also to grow as an individual. I would set deadlines for myself at work... let me finish this project, close this sale, launch this brand, you name it, I had all the excuses in the book to hang on a little longer. I agonized over the decision and to be quite honest, procrastinated pulling the trigger.
This might sound like the craziest cliche ever, but once I left, I didn't look back at all. How could that even be? A decision that caused me so much internal and external struggle finally was solidified and all of a sudden I forgot the distress it caused me. I guess the bright side is despite the fact it took forever and a day to get here, I at least know I made the right choice.
I don't want to say that anything about this has been easy, because it hasn't. If you think answering to a boss is hard try having to answer to yourself. Of course, I have the luxury of "making my own schedule" but that privilege also comes with a price. My work and my business is part of me. It is mine and I am a part of it. There's no separation of the two, they're connected. If you're asking yourself, well what about work life balance? Then you're probably not wired like me and that's ok. But if this is resonating with you in the slightest, I am writing this to encourage you to take the chance on yourself.
I don't think of work and life as a scale I need to balance, I think of it more as a wheel. I work, I play, I work while I play, and I play while I work. It never really stops - it just keeps spinning, and I love it. People always ask, what's the best part about owning your own business? For me, it's been the "wow" moments. The moments when the crazy thoughts you have about yourself and your business actually become things. I distinctly remember saying things like "When we do X amount in sales in a year, I'll be excited." Then X goal happens in a month. Or, when I dreamt that my commute to work would one day actually be me walking to my very own office. In fact, I even remember walking to the printer one terrible day at work while telling myself I was going to write about this once I transition into a full time entrepreneur, and look, here I am!
To look back and realize I have accomplished all those things, is pretty wild. It's made this journey even more worthwhile.
The same boss who made me search for my "why" (also known as my favorite boss ever) used to talk about "fire in the belly". She would use this phrase to refer to the people with guts, passion, and ambition. She had all three. I guess I did, too, part for which I definitely have her to thank. I also had that relentless voice in my belly. I'm here to tell you I am happy I listened to it. The first 8 months of entrepreneur life have been incredible.
My hope is that this blog sheds light on my journey, but more importantly empowers you to find your "why". If you have an itch, a fire in the belly, ignite it. And let it burn baby until you blow that sh*t up!
Jackie Sheehan Brady
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