Friday Reflections, Redefining Success

A couple of weeks ago, I was sitting around a cluster of cocktail tables, listening to a group of women talk about Passive Income. They were discussing strategy, sales, “making money while you sleep,” spreadsheets, mailing list, etc. etc. etc. As I listened to them speak, I felt so… lost. “How did I get here?” I wondered.

I walked home from the meeting with a terrible, sinking feeling in my stomach.

The truth is, I’m not a great salesperson. I’m not a strategist. I’m not skilled at “building a brand” or selling myself. If I’m being completely honest, I’m not sure if I want to be any of those things. I just want to be myself, for better or worse. I just want to be authentic, to follow my heart and see where that leads me.

I want to be creative. I want to make things with my hands. I want to travel. I want to play. I want be inspired by people. And, with this blog, I want to share my ideas and experience with whoever might be interested (which might, realistically, be only my best friend and my mom).

I don’t want to pre-plan my every move on social media. I don’t want to edit myself. Obviously, I want to put my best face forward (as much as possible) but I really hate the thought of doing anything simply because it can get me more Instagram followers or more Facebook likes. (That’s obvious by how low my number of followers is!)

I want to craft a meaningful life. I made the decision, a while back, to stop chasing success and start focusing on being happy. I think, subconsciously, I had always measured success in financial terms. If I had enough money to live the life I wanted, I thought, I would be successful and, in turn, I would be happy.

But the older I get, the more I realize that that’s just not the way it works. Sure, money buys comfort and security (which can go a long way towards making you feel happier) but it doesn’t make you happy. I’ve had years where I felt like I had enough money and I didn’t worry about how I would pay my bills and I’ve had years where I felt very poor. Looking back, I was no happier when I was financially secure than I was when I had barely enough to get by.

When my husband (then boyfriend) and I lived in New York City, I remember thinking to myself “I wonder how many days I can get by eating only peanut butter and jelly?” because I couldn’t afford to buy many groceries. When I look back on that time of struggle, I don’t think about how we didn’t have enough money to go see a movie or about how it felt like all of our classmates were killing it in their high-powered jobs while we were barely getting by. I think about how much fun we had. I think about rolling out a travel picnic table, on the floor, as our dinner table every night, because we didn’t have room for anything else. I think about how, as a special treat, we would walk to Whole Foods (the cheapest place for groceries in our neighborhood- no joke!) and buy $2 chocolate pudding cups. Sure, it was challenging, but we had a great time.

Fast forward 8 months later, we were living in Chicago, and I got a law job that paid me more than I had ever earned before. Suddenly I had money! Not a ton of money by any means (definitely not!) but enough to pay my half of our rent and make my law school loan payments with a little leftover for fun things. I should have felt like a success, according to my very narrow definition, but I didn’t. I felt miserable.

I hated the job. I felt like a peon that nobody cared about. I sat in silence for 8 hours a day, in a big room full of strangers who had no interest in getting to know me. I stared at a computer screen, clicked a mouse and felt like my soul was dying, bit by bit. When the paychecks arrived, I didn’t feel happy, I felt empty and disappointed. I felt so….lost. “How did I get here?” I wondered. Where had I made a wrong turn and how do I get back on track?

In the 4 years since that job, I have made significant changes in my life. I have redefined what success means (money be damned!) So, when I sat around those cocktail tables the other night, and that all-too-familiar feeling of being lost crept back in, I thought “This isn’t what I want.”

Don’t get me wrong- we all need to make money. We all need to pay our bills and buy groceries and plan for the future. There is absolutely nothing wrong with wanting to make money and wanting to be a success. What I’m trying to say is that, for me, it can’t be at the forefront of my mind. For me, financial success can’t be the driving force behind any of my endeavors. As soon as it is, I’ll be back to that sinking feeling.

The truth is that nobody knows what the future will bring. Nobody can be certain that the path that they are on will lead to fulfillment and success. All anyone can do is try to follow their heart and listen to that little voice inside.

For me, that little voice is saying that I never want to sell myself. I never want to be someone that I’m not. Maybe that means that I’ll never be a smashing success. Maybe it means that I’ll never be the boss lady.

Maybe that’s OK.


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