As almost any entrepreneur or creative will tell you, unexpected problems are to be expected. Below, you’ll hear some incredible stories that highlight and illustrate the kinds of issues and problems entrepreneurs and creatives are dealing with everyday. It’s not easy, but the silver lining is that dealing with unexpected problems is one of the best ways to develop antifragility.

Shawn Morrison

Will You See Me?
Stories From the Streets

For more than 30 years I’ve had the privilege to work closely with those who struggle to survive. I’ve met the urban poor, those experiencing homelessness, individuals with mental health concerns, and persons struggling with addiction and substance abuse. Read More>>

Kwinetta Moore

One of the most unexpected challenges I faced in my business actually came during a time that was both really exciting and deeply personal. Last year, I launched a children’s book designed to teach little Black children about marketing and strategy — two things I’m incredibly passionate about. I poured a lot into that project. From writing and designing to building out the launch plan, I was fully invested because I believed (and still believe) representation in business education has to start early. Read More>>

Shackisha Clark

One of the most unexpected—and frankly disheartening—challenges I’ve faced in my career is dealing with individuals who expect high-quality professional work without being willing to pay for it. As a tax and financial professional, I’ve had clients who approach me, clearly aware of the value I bring, but they only want to pay if they “like” the outcome—even if that outcome is governed by legal facts and not my effort. Read More>> 

Brian Staugaard

Collecting the money owed for services rendered.

Im not a huge money driven person. I am in pursuit of my ideal life. Yes money is a through line, but its not what motivates me, my dreams of being in control of my time is what motivates me.

Money buys car parts, but what i enjoy is building the car itself. Read More>>

JEANNE ROREX BRIDGES

I might be the first artist you have interviewed who has had to fight the federal government to sell her work. My family has Cherokee blood, but my paternal and maternal grandparents chose not to the Dawes Commission Roll at the turn of the century. I respect their decisions because there were many reasons to NOT sign and only one to sign – to get free land. With that land allotment, you gave up your tribal citizenship and you and your children became wards of the United States Government. Read More>>

Monetia Smothers

June hasn’t been the kindest to me. A lot of things I planned had many twist and turns, people and scenario switch ups. But, through it all I also see the blessings and the lessons of it all. I recognize that God has been with us the whole time. And though it didn’t work out exactly how I may have visioned it definitely still happened. Which allows me to know everything takes persistence and patience. And to never give up on your goals. We may fall down but we get up! Read More>>

Hadar Greenberg

I started my business in 2015, shortly after the birth of my second child. It grew quickly—by 2019, I had a dedicated team of ten, a beautiful office space, and a strong base of clients I deeply valued. Business was thriving, and the future looked bright. Read More>>