Celebrating a Decade of Being an Entrepreneur


Today marks 10 years of being in business for myself. On August 15, 2003 I invested $100 into a financial services business thinking it would be something I would do “on the side”. A decade later, it is something that I love and am passionate about. Although I’ve built a nationwide business, I feel like there is so much more to accomplish and I am just getting started!

I didn’t always think of my career in terms of being an entrepreneur; I just knew that I wanted to have my own business. I had worked for a graphic design firm, and while I was doing something I loved, I wasn’t working on projects that were meaningful to me. I was making money for other people doing work for other people! But how could I strike out on my own? I tried starting my own graphic design business. I tried starting my own jewelry design business. Each time, I loved what I was doing, loved making my own hours, loved only taking on projects that interested me. Each time, I reached the same impasse: Now that I’m doing this, how to I become successful? Each time, I was stumped.

Perhaps the biggest challenge of entrepreneurship is having the courage to let go of the tree trunk and climb out onto the limb– that’s where the fruit grows! The next biggest challenge is the one I found myself facing: Once you get out on the limb, how do you climb to the top? Where is the path? Who is going to call out and tell you the easiest branches to grab, or even stretch out a hand to help pull you up?

That’s the perceived advantage of working a traditional job: In most cases, there’s a clear-cut path to the top. You can see and understand what you’d need to do to get promoted and be successful. There’s a timeline. There’s a process. There’s a ladder. But your progress up the ladder is fully dependent on other people permitting your to climb higher or getting out of the way of your climb. Your progress to the top of the tree is up to you and only you, but there’s not a prescribed way of climbing.

When I stumbled into my current job as a personal finance coach, I was only 20 years old. I was an independent business owner, but I operated through a larger company. I treated it like just another way to make money until I realized two important things: I really enjoyed helping other people improve their financial situation, and, most excitingly, that this combined the freedom to climb the tree at my own pace and a plan to get to the top. It awarded initiative, but in a predictable way that led, step-wise, to success. Everything I loved about being my own boss and all the security of a traditional job…? It was the perfect match for me.

Most entrepreneurs don’t experience that same winning combination of freedom and support. So what can they do to increase their chances of success? Here are a few tips:

  • Find a mentor. Unless you’re doing something totally off the wall, chances are there are others who have been successful in a similar or complementary field, or maybe there’s an entrepreneur you’ve long admired. Contact them, and offer to buy them a drink or take them to lunch, in exchange for picking their brain. People love to talk about themselves, and any savvy businessperson won’t shy away from a professional connection! Social media has done wonders for breaking down communications barriers. You can easily tweet at the CEO of a successful company, so take advantage of it.
  • Figure out another way in. If you’ve done your homework, you’ve identified a target market for your product or service, but it’s worth brainstorming about other businesses or organizations who have access to potential clients or customers. If you run a pet grooming service, you’re probably targeting dog owners in your area, but have you talked to all the veterinarians who are in a fantastic position to promote you? What about offering discounted services to an animal shelter, or a coupon to everyone who adopts a dog? Taking a few hours to really get creative about your channels can pay off!


  • Be your biggest fan. You are your business, so be excited about it! Not saying you have to be a walking commercial, but the more people who know what you do, the more likely it is you’ll get business from referrals. Perhaps whomever you’re talking to doesn’t need your product or service, but their friend/mother/sister/priest/hairdresser might!


Forging your career with your own two hands isn’t easy, but it is incredibly rewarding, both personally and professionally: I know I can overcome any obstacle; I know I can be self-sufficient. Perhaps most rewarding is that fact that my success now allows me to help others on the same path, to reach down and help an ambitious climber grasp the next branch.

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