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.

Alma Ramirez

I graduated from art school in 2008, and I was sure I loved art, I enjoyed painting but I was experiencing a major burned out. Being creatively blocked I stopped creating for a few years. I didn’t feel I had a voice in art or a particular style. I was trained in a very classical academy working on realism and the human figure. I enjoyed the process but it wasn’t me. I was searching for something that I could share with the world but nothing seemed meaningful at that time. Read more>>

Paty Johnston

I was at a job that I didn’t like and every single week I thought about quitting. One day I was courageous enough and decided to leave that job and open up my own business. It was the most unlikely business that I could be in a mechanic shop. I opened it off with $2000, and they were all of the savings that I had in my life. I used $1000 to pay for the first month’s rent and the other $1000 to buy a brand new computer. Read more>>

Kayo SinnedOut

A problem that I personally faced in my business is being consistent and staying motivated. This is something I think every creative goes through at least once in the journey and it could be for different reasons. Someone bigger than you might be stealing your designs or way of creating or you are just having a creative lag and can’t come up with any ideas. The way I go about it is instead of looking at those things as bad and bringing me down, I use it as motivation that i’m doing the right thing. Also sometimes we need a little break to reset and gather our minds together. A break is never bad unless you gain nothing from it. Read more>>

Breonna Brooks

Hi my name is Bronna but in the creative community I am known as Thebrooksimpact. My creative journey has been a long line from studying fashion merchandising at Texas Woman’s University as well as spending some time learning about fashion in London and Paris the creative world has taken me on a roller coaster ride. And at one point I even found myself being sued by Model. In my world I believe that everything is an experience and it’s all about the way that you look at things and although some might see this as a negative thing this lawsuit landed me on television. Read more>>

James Chapman

We started Plain Sight to improve the way connections were made in-person, but we launched it just 4 months prior to the start of a global pandemic that prevented people from gathering in-person. So, as you can imagine we had to learn how to pivot and do so quickly in an ever-changing world with a small team and a small budget. While the pandemic was totally unpredictable, we knew that we still had technology that we could repurpose until the time came for us to be able to use again for our core mission. Read more>>

Terance Shipman

The most unexpected problems I’ve faced in this book publishing journey has been getting people to leave reviews and simply buy books from the website. Reviews for an author are very important. They can drive your sells up. One of the hardest things has been just getting people to leave one. It can be friends, family members or strangers, asking them to leave a review and them doing is amazingly hard. Read more>>

Brian Lettieri

The world of E-commerce from a PPC & SEO view is ever evolving so there are always unexpected issues to overcome. Being able to buy ad space and rank for terms organically with Google and other major platforms is something that evolved in the last 10 years. When scaling that space as algorithms shift it can tank business models built around it which is why companies in this space always need to be learning. When executed well it’s also what makes this space extremely rewarding. Read more>>

Satoya Pollard

Some of the most unexpected challenges that I’ve experienced as a hairstylist is having what’s called, a slow season. My slow season is typically during the summer months because a lot of natural clients are wearing braids due to the summer heat. One thing that I did was create different packages that would be beneficial to my regular clients. This advice was given to me by a salon owner and it truly helped. I already have packages curated for clients who needed a little extra TLC. The newer packages focused on treatments that will be beneficial for clientele who are coming out of summer protective styling. Read more>>

Dimitris Gazonas

Unexpected problems: 1) Money required Starting out in digital marketing seems so easy and carefree. There are a lot of opportunities out there that require “little to no investment”. Others say you can get started for a very small investment. What a bunch of crap that is! Whoever says you can make money with little or no investment is scamming you. Every business venture requires cash as a car needs gas to move. It is the single most important component in a business. You go into business to make money. You invest money and get a return. Read more>>

Jearlean Taylor

My life has had some unexpected outcomes. I guess you can say “life” happened. At the tender age of 3 years old I developed a rare form of cancer (Rhabdomyosarcoma). It was because of the location of the tumors and chemo & radiation, I had to undergo ostomy surgery, which left me with two permanent ostomy bags. I was cancer free a year after my diagnosis and treatments, but 2 ostomy bags. Read more>>

Drew Stier

I was already planning to stay at Chris’s family home for spring break from college, but when Covid-19 shut down the dorms, we realized we would be living together for a much longer period. We spent the first few weeks working on an EP Chris had written inspired by our first real experiences going out in New York City earlier in the year, but after a few weeks the music we were making began to shift into something darker and earthier, more in tune with the bleak times and the woodiness of our surroundings. Read more>>

Devin Gatling

Some of the most unexpected problems I’ve faced as a creative on my journey are a few things lol but to narrow it down to the most important for me would probably be miscommunication / expectations. a bit of backstory about communication / exceptions, for starters would be the act of getting the vision out of whomever i’m working with communicated to me properly in order to execute on the vision. Yeah im skilled at what I do but I’ve had years if practice at it so my process these days are thoughtless & transitioning to working with people, Read more>>

Jaye Backus

I didn’t realize it at the time, but I started my business in a scarcity mindset and didn’t think much about what it would be like to actually own a business. I desperately wanted the flexibility to work on my own creative projects and was anxious to leave my old job to free up my time. I focused on short term goals and I gave very little thought to longterm affects of my business decisions. This led to a near 100% booking rate (I accepted every inquiry that came through my inbox – good or bad) and ultimately, a hand injury from overuse. As my offerings and products evolved I never shook the desperation and it permeated through every part of my business. Read more>>

Marcelle Folk

My business faced the pandemic unexpectedly. It started as a side business back in November 2016. By February 2020, I left my federal government job to pursue events full time because there were so many signs that we were ready for that leap. Three weeks later, everything shut down due to the pandemic. Events canceled left and right, and we gave full refunds to clients (even though the contracts only allowed 50% refunds). But our morals and ethics forced us to give back every penny we could. Read more>>

Megan Vaughan

The hardest thing about being a business owner is keeping your mind open to reimagining what your business looks like in order to keep it viable and current. In March 2020, Vaughan Cheese exclusively offered in-person events and sold wholesale to restaurants. It was projected to be our business’s biggest month yet. In a single day, every one of our accounts closed and every event canceled. We found ourselves with tens of thousands of perishable goods and no revenue streams. Read more>>

ROMIRA YOUNG

Two words. The pandemic. I was not expecting this. It’s like one day, business was booming, we were meeting people from all over the country, and hosting large groups, monthly, and the next thing you know, the world completely shut down. Over the past two years, we’ve experienced more growing pains than what some would consider normal. While I can look back, and know that each test served us well, and taught me how to handle tough challenges, sometimes I wish the lessons we had to endure were much lighter. Read more>>