Oh, the places you will go (Part 2): How to make it in America

Oh, the places you will go (Part 2):  How to make it in America

In my last post, I explained why I left my career on the corner of 63rd street, downstairs from a bar and next to a fried chicken joint.  In short, one day I came to the realization that I did not want to wake up, thirty years from now, angry with myself and everyone around me.   By that time I would have surely convinced myself that settling for a miserable career was the right thing to do.   Yet, doing so would have only made me a martyr in my own mind; to everyone else I’m sure I would have been a real beyotch.

…And I didn’t want to be a beyotch, at least not in this lifetime.   I’d much rather be happy, even if it meant that I would make less money.

I had to trust that if I could make a career for myself once, then surely I could do it again.

Yet, I’ve been wondering what separates the dreamers who succeed from those who merely fantasize and never act?  I have a dollar and a dream but somehow achieving success seems more complicated than that.   For this reason, I sought the advice of four people who have paved their own paths and have achieved success while doing it.

Meet the “Dream Team”

Lynnette Astair, Fashion, Art, and Celebrity Photographer; Visual and Performing Artist; Creative Director of CY Magazine; Up and Coming TV Show Producer and Host.

Jason Coleman, Executive Director of Project SYNCERE, an educational not-for-profit focused on exposing underserved children to curriculum in STEM (Science, Math, Engineering, and Technology) fields.

Jo-Ann Enwezor, Owner of Planet Maud Vintage & Co., an online fashion boutique specializing in vintage clothing and accessories.

Tiffani Murray, HR Technology Consultant, Social Media Expert, Author of the “Stuck on Stupid” Book Series, and Owner of ATM Enterprises.



I have no idea how to be a successful writer, I only have a wicked sense of humor (when I’m drunk) and an unique way with words (so, I’ve been told).  With the rapidly changing landscape of social media and PR, I recognize that more important than the words that I write is the way that I brand myself.   (And I know nothing about branding myself; I don’t even like men looking at my butt.)  So I was excited to turn to Lynnette Astaire, a photographer and artist, to understand how creativity and business can mix.

Dream Tip #1:  Be okay with others not understanding your vision

Lynnette’s passion for art and beauty permeates out of everything that she does, yet I wondered whether the decision to pursue an untraditional career came easily.   Lynnette explained,

“No one in my family is in arts & entertainment so it was a slight challenge when I decided to go to art school because they didn’t get the industry or lifestyle. My granny assumed I’d graduate and find someplace to be a photographer that would give me 2 weeks’ vacation a year and a gold watch at retirement --- and it doesn’t work that way!”

Dream Tip #2:  Successful entrepreneurs are at the mercy of their clients…and their employees

My favorite piece of advice came when asked about the most challenging aspect of running own her business.

“I think the biggest misconception about running your own business is that you stop working for other people. [If] anything you work more -- and often times the boss becomes a slave to the employees! If you’re about making money you will ALWAYS have to work for someone else but as your own business you get to dictate how and when that’s done.”

Dream Tip #3:  Take your business as serious as you take your craft

So why are there so many starving artists?  How can I keep myself from becoming one of them?

“Unfortunately most artists could give a shit about business, we just want to create. It’s an ongoing challenge to keep the creative juices flowing when you have to crunch numbers… [Learn] to monetize your gifts.”

For more information on Lynnette, go to www.lynnetteastaire.com or follow her on twitter @lynnetteastaire



As someone who has managed a not-for-profit, I wanted to profile Jason Coleman because of his organization’s unorthodox success in a city inundated with not-for-profits that are well-meaning, underfunded, and poorly managed.

In the short span of three years, Project SYNCERE has served over 1,500 of Chicago's youth and is now partnered with over 20 schools through the city. Its staff has grown from three directors to over 25 program instructors, all in the face of a recession and ever-decreasing school budgets.  For that reason, Project SYNCERE’s successful is a phenomenal feat.

So I wanted to know the Executive Director’s secret.   Was he sleeping with someone powerful and rich?  Did he have to rub elbows and smoke cigars with the city’s powerful elite?  To my astonishment, neither of my assumptions were correct.

Dream Tip #4:  Be passionate about your mission

Jason, who was a senior mechanical engineer for Motorola, enjoyed the benefits of a successful career but “didn’t like the fact that there weren't others that looked like [him] in the profession.”  Feeling frustrated with the number of minorities entering the technical fields, he recognized that he had the ability to expose underserved youth to STEM careers and to be a catalyst for the solution to this problem.

Dream Tip #5:  Be prepared to be broke…but only for a while

When asked about the most difficult part of leaving his corporate career, Jason replied that his biggest fear was “not knowing whether his ideas were going to work”.   As an unfunded organization, the three leading directors started out doing many of their programs for free and investing their own money to develop the market for the organization.   They also networked heavily with people that could connect them with larger networks of people who would one day need their services (including principals, schools, and elected officials).

Dream Tip #6:  Take care of your business so you can execute your vision

So what is the first step for someone wanting to start their own not-for-profit?

“[Apply] to become a 501c3, [this} is the first step in being able to receive and apply for grants. But for any business, you need to have a vision and goal set for what you want out of the business and develop a plan to make that vision reality.”

Dream Tip #7:  Pushing Past Rejection

With so many not-for-profits that fail within their first year, I asked Mr. Coleman to tell me what he thought was the biggest obstacle to success.

“The most difficult part was dealing with rejection…and not getting contracts with the schools to really jump start the business.  A lot of people told us that we were too expensive and that is way too much for programs, but we stuck with our plans and went out to more schools and talked with more people to help open up more doors for us.  It worked and we are now [functioning] as a thriving business”.

For more information on Project SYNCERE, visit their website at www.projectsyncere.org.


(Next:  Part Three – How to become a subject matter expert; How to start a retail business)


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    Kay S

    Kay Smith is a Chicago-based freelance writer and blogger who focuses on race, politics and urban culture. Having worked on public policy at the state, regional, city and community level, her opinions have been featured in the Chicago SunTimes and a host of news websites (under very mysterious sounding pseudonyms). Follow her on Twitter @kaywillsmith or contact her at kaywilliamsmith@gmail.com.

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