2 Must’s For An Aging Creative


I’m what you would call a fashion head. I’m open-minded when it comes to fashion yet I grew up poor and rarely had new clothes.

Being raised in the age of baggy jeans — a fashion era I honestly thought would never fade. I was so ashamed by the fact we always shopped in thrift stores. But I remember the day I realized that getting pants from the men’s section in a second-hand store was my “cheat code” to the baggy jeans look.

There was also the “sta-flo” period that created such heavily starched jeans that they would stand up on their own. The 501 Levi style hit and then one day, fitted jeans were the thing. As a southern hip hop head, I believe Kanye and Pharrell are the forefathers of ushering in skinny jeans.  I remember being skeptical and thinking, “Is this going to stick?”

Yep, it did.

Over the years, I’ve become the go-to person for others because of my take on fashion. In fact, at one point I was responsible for over half of the shoes in my wife’s closet.

The influencers of fashion had my attention. I remember watching a show with my wife called Rip the Runway, and I predicted the rise of the Michael Kors and the demise of Jessica Simpson labels. I saw somebody with a fedora and remember saying to myself that if those hats become accessible, I was going to find a way to wear them.

This moment changed my whole look.

I planned to wear the nappy fro with the fedora and call it the “trap hipster” look. I remember the first time I posted my pic with my new style. The text messages poured in from friends clowning me. I would send out new press pics with my new vibe and promoters, booking agencies, and artists. They would say, “Bro, what are you doing?!”

Now, four years later, almost every artist I know has worn a fedora at one point or has an image that resembles my press pics. There is liberty in being different and trying something new. It gives you a confidence you didn’t know you possessed or desired.

So what is the aging creative to do amidst all the change?

Here are two things I believe will allow God to use you to your highest creative potential:



Everybody has a squad. I use to live in Oklahoma where hunting is a common pastime. However, I’m a black man who grew up in the hood and guns were never really for sport (Well, never mind).

I look like a rapper everywhere I go, and I would frequent a store called Bass Pro with my kids because they liked the lake outside the store. As outlandish as that may sound to some, visiting this store would always introduce me to new stuff that was not in my world.

For example, I never understood the hype for a boat until I visited that place (LOL). A few years ago I was hanging with a family, and the husband expressed his desire for a boat, despite his wife’s initial displeasure with the idea. My Bass Pro experience provided me with a connection point to understanding his passion for a boating hobby.

This experience taught me the value of going places you don’t fit.

My advice is always to put yourself in a world outside your immediate circle, even though your friends will laugh at you privately or publicly. This idea helps you build healthier relationships and challenges the cliques around you. So if something different calls you, you know you can tolerate the reality of being an outcast.



The older you get, the more you find comfort in being right. Though creativity is a grey area that requires flexibility because a bad idea today can be a good idea tomorrow.

Also, there are no bad ideas, but there are underdeveloped ideas.

The older you get, the less you control what is cool. Most of us don’t want to admit how much our identity comes from being able to laugh at somebody who is “uncool.” When we can’t as a creative, it makes us feel insecure and causes us to withdraw to a place where we can define what is right and wrong for ourselves.

As an adult, you see this during creative meetings where older people become sarcastic about the cultural difference of the previous generation or proceed to reminisce about Blockbuster while belittling Netflix. This creative finger-pointing shuts you off from new ideas because it allows self-righteousness to win.

But in reality, being right is overrated.



Anthony Flagg


Christian Music Artist