Freelancing

For the past two years, I have had a full-time job in Jamaica while wanting to become a freelancer. I wanted to set my own schedule, travel the world on speaking engagements, and inspire others to break out of the traditional career paths and forge a new way. But I was too afraid to let go of the security of a monthly check: I had over $60,000 of debt from Harvard Business School, and I put all my savings towards paying off other consumer debt I had built up while at school. There was no financial cushion.

Before I jumped ship, I had to get very specific on what I wanted to do, what I was good at, and what people would pay me to do. It took the past two years for me to figure this out.

  1. What I want: I want to be a writer and to live in Europe for short periods each year. I had wanted to be a writer until the second to last year of high school, when I decided I should put my brain to something more prestigious, like economics and business. Any business I set up now will allow me to develop my writing life and spend at least one month each year somewhere in Europe.
  2. What people would pay me to do: Jamaican businesses have an unmet demand for help with strategic planning, financial projections, and developing formal business plans to take to banks and investors to raise capital. My current company does all this, and I will most likely set myself up as an outsourced resource for the company, in addition to taking on special projects.
  3. What I am good at: I am good at building a strong network and getting people to believe in my abilities and to want to do business with me. I regularly sit down to lunch with the biggest CEOs in Kingston and convert a high percentage of clients that I have a face-to-face meeting with. The problem is I currently don’t sit down with clients enough.

I have been asked many times over the past two years why I didn’t set up my own business immediately after moving back from HBS. The answer is this: I had to get very specific about what I wanted out of life and build the roadmap for getting there first, before I felt comfortable with becoming an entrepreneur. Now I recognize that I don’t want to build an empire, I want to live a full, interesting life with the freedom to do what I want, when I want. I am finally ready to become the CEO of Me, Inc.

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4 comments

  1. Good vibes Lis. Life is what we make it, and ain’t nothing impossible. Your goal seems similar to mine, details differ and the career path to get there different, but more or less very similar targets and visions as to what “work” and life should be. Forge ahead. I’ll see you when we get there.

    1. Thanks! We have to take the opportunity to do this while we’re young with few commitments.

  2. I have toyed with the idea of sticking it to the 9-5 thanks for the guidance re: what questions to ask myself. I think I just need the faith

    1. It helps to have a community of people who did it successfully that you can look towards whenever the fears start creeping in. For me, they are Marie Forleo (http://marieforleo.com) and my good friend Kaneisha Grayson (http://kaneisha.com).

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