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The moment I left for college, for some reason, I no longer had a consistent sense of satisfaction. I can honestly recall one moment in time where I was completely satisfied with where my life was, where it was going and how my overall future looked. Yes, you read that right, one time only since high school. I was sitting on my couch in my home in New Jersey about 3-4 years ago, after a hard day at work for another law firm. I was watching television, my bills were paid on time, I was dating the man who would eventually become my husband, my social life was great and my family was healthy. I thought that the space I was in was perfect and it would only get better.

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Well, that feeling lasted for a short period of time as I was subsequently laid off, rented my home out to someone else, and moved in with some friends in an effort to save money. The initial plan was to move in with them to save money for an apartment I really wanted because I no longer liked the neighborhood where my home was located, but that’s not how it turned out. What started out to be a “well thought out and executed plan to justify moving to an expensive neighborhood” turned into a necessary move to not go broke. I was back to not being satisfied.

I am accustomed to being in a space of not being totally comfortable with where I am in life. In fact, it is more the norm for me than it is an anomaly. But what does that say about my perception on life, its successes and failures? Am I setting myself up for an eternity of feeling like I am “not quite there yet”? I mean, by all accounts it’s all good. I am a business owner who sets her own hours, I am married to a great man, we are expecting a baby in September, I was able to sell my house without owing the bank any money in this horrid housing market, my family and friends are great, and I love our new apartment. However, there is a pesky thorn in my side that is telling me, there is more out there, there is better to be had and done with my business, I have not arrived at my final destination.

Could I be making more money with my business? Hecky yeah!!! In fact, it is the only thing that I loathe about being an entrepreneur. You never really know where your next check is coming from and it can become frightening. I mean, when I got to the place where I could pay my mortgage, rent and other bills (on time), from the money I made from something I created, I ALMOST felt like I made it, until I did my taxes and started to compare what I earned working as an associate for someone else with what I bring home yearly now. There is no comparison, but for some strange reason, I am better off financially now than I was when I was making more money. It boggles my mind every time I think about it.

According to a recent AmericanExpress/Open Forum article, many entrepreneurs face the same feeling daily and that is the feeling that there is never “enough.” As noted by Michael Michalowicz, Entrepreneur and CEO of Provendus Group, “As you climb the mountain of financial success, you can see farther and farther. You see many taller mountains, and people are already climbing on them. So, no matter how successful you are at getting to the top of the mountain, you’ll feel you haven’t reached the top. You may just drive yourself crazy by continuously trying to reach the highest summit.”

He notes that the triggers for these feelings include:

  • Attempts to “Keep Up With the Joneses”,
  • Taking on More Financial Stress with Each Financial Success, and
  • Pursuing Money Instead of Pursuing Happiness

He was absolutely correct. While I was VERY close to a feeling of satisfaction and complacency several months ago, I was on the phone with my mother telling her about my day, what I was working on and assuring her that I was fine, she said something that jolted me back to my reality of “This Ain’t It”. She said, “You are nickel and diming it, time to think bigger and go for more. Do not be satisfied with where you are now, it’s just the beginning.” She was right.

Yes, I had reached a level of “success” for the first time in my career by being able to support myself and contribute to my family with my business. This was no easy feat. After years of not accepting my fate as an entrepreneur, and wondering what is next for me if I am not a W-2 employee, to finally being able to support my lifestyle , I thought I had made it. I was almost satisfied. I was almost to the point of feeling that I had “enough”.

Though I constantly wrestle with comparing my work day to the days of my friends who commute to a 9 to 5 every day and who know for a fact that their direct deposit will hit when it is supposed to, I have to accept that I am pursuing happiness and contentment instead of money. Work happiness, for me, happens to be working from home, on my schedule, doing what I want to do. As an entrepreneur, in order to stay on this path without feelings of inadequacy and/or failure, you have to keep that in perspective. The financial goals for your business will change with each season, and will be met; however, where you are now is exactly where you are supposed to be.

Rashida Maples, Esq. is Founder and Managing Partner of J. Maples & Associates ( . She has practiced Entertainment, Real Estate and Small Business Law for 9 years, handling both transactional and litigation matters. Her clients include R&B Artists Bilal and Olivia, NFL Superstar Ray Lewis, Fashion Powerhouse Harlem’s Fashion Row and Hirschfeld Properties, LLC.



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