1st Generation Entrepreneur and 1st Generation College Student

'I am the master of my fate: I am the captain of my soul." - Invictus


For as long as I can remember, my parents had preached about the importance of education and their dream for my siblings and I to attend college in order for us to have a better life than they experienced. I would like to say I was marred by fear but the excitement of change was enough to convince me to apply to a local arts college (with the hopes of having a Fame-like experience). You learn fast that as the first in your family to attend college you are now the great-hope. They don’t know that you are learning on the job, trying to figure out what a bursar is while listening to peers unconsciously brag on how their parent or older sibling was helping them along the process. The pressure to succeed is indescribable.  You can feel as if you are in a silo when problems arise because the idea of calling home with problems would disappoint the dream so you do what you must to make it happen.

Fast-forward six years, not only did I finish college but I also completed an accelerated graduate program and landed a ‘good’ job making more money starting than both my parents. I did it! I made the dream come to life and I was the pride of my family. My mother would somehow find a way to let complete strangers know I had a master’s degree. Cashiers at the grocery store. The waitress during dinner. The crossing guard. And now, any issue involving paperwork had to be reviewed by me. Bills. Disputes. Late pizza deliveries. I would remind my mom I wasn’t a lawyer. I had completed two degree programs, none of which offered a business course but it didn’t matter. If I approved of a situation or product, it was golden. They were proud until I did the unspeakable. In 2006, I quit my good paying job to pursue my new dream of becoming an entrepreneur. It was my new dream because the initial dream was to finish school and get a job. But you soon learn as a 1st generational graduate is, the idea of possibility goes beyond ‘a good job.’ It teaches you that any amount of time and determination, you can take an image, floating comfortably in your head and introduce it to the world. Completing college and graduate school gave me something I wasn’t expecting to gain; gumption. Coming into a world where I felt I had few accessible resources and coming out on top didn’t eliminate fear completely but it introduced a willingness to try.

While sitting on the fence determining whether to leave my current position for another job or to leave to create a business, my co-worker and I had a meeting with Mama Kaye, aka ‘Moses’. I nicknamed Mama Kaye, Moses after Harriet Tubman because we truly feel as if she led us off the plantation and she was pivotal to my strength and ability to take the first step towards entrepreneurship. Mama Kaye had volunteered with our organization and has the type of personality and spirit you can’t ignore. She has an accomplished background but most importantly, she was an entrepreneur and explained how not having a 9-5 works in the real world. As my co-worker and I leaned in to hear the answer to this great unknown, she told us something I will never forget: we would be OK. Surprisingly, that was enough. She explained, you will go into survival mode and if business is slow, you will temp or work part-time but keep moving forward on the business. Done. The world was my oyster.

This coming February will make my eighth anniversary as an entrepreneur and to offer a quick synopsis of what the experience as a 1st generation entrepreneur has been like, I’ve started a blog called How2FailAtBusiness. I’ve had some really good years and some really horrible years but I’m still OK. Unlike starting college, starting a business didn’t come with a bursar office and my nonprofit management training became a hindrance for accounts payable or what I renamed, accounts delay-able. Worst of all, I lost my great-hope status. My parents who had always taught us that we could do anything we put our minds too could not wrap their heads around why in the hell would someone with multiple degrees and a business moving at glacier speed wouldn’t just get a job and a paycheck? But I couldn’t. I knew too much and my faith in myself was greater than my material needs. I figured, no one explained to me the first year of college what a bursar was and no one explained there is another side to the joys of entrepreneurship flaked with failures and misdirection’s. Business was moving slower than I had liked but nothing great without sacrifice, right? So when I had to file bankruptcy last year because a complicated medical procedure cleaned me out financially, I thought, it can’t end like this.

As a 1st Generation Entrepreneur I was back in the silo I had felt as a 1st Generation College Student, except the excitement I once wore as a badge of honor was now fear. And the gumption is had acquired was plagued with embarrassment. I would read stories of entrepreneurs who had fallen on hard times and how hard it was for them to go to their families and ask for help but I was the help in my family when I had a 9-5 job. As an entrepreneur, I was a burden and definitely not OK.

Its been about a year since I filed and to say its been an uphill battle is an understatement. College offered a cheering squad in the form of instructors. In graduate school, we were a cohort with a ‘leave no man behind mentality.’ As a lone entrepreneur, the fight and drive you need to persevere is completely internal. I can say, I am thankful for my spiritual base and look forward to my daily devotionals the same way I used to look forward to a speeding-spree at Nordstrom’s. I understand, as William Ernest Henley taught me in poetry class, ‘I am the master of my fate’ and as one bad grade didn’t dismiss my chances of receiving my degree; my entrepreneurial misdirection is simply a detour to figuring out the correct path, as I, and many other 1st generation college students have done and 1st generation entrepreneurs can not help but to do.  

“It matters not how strait the gate,

How charged with punishments the scroll.

I am the master of my fate:

I am the captain of my soul.” 

 — William Ernest Henley

Dawn Callahan, known as America’s Favorite Business Test Dummy, is an advisor to entrepreneurs and blogger at How2FailAtBusiness.com. She is also special contributor on KPFT-FM Houston, Money Matters Monday’s.

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