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Pictured: Charles Bradley, Soul Singer. Winner at the long game.
At a dinner party recently, I shared a theory about life that I'm starting to believe. It is this:

You can have anything you want, as long as you are not attached to 1) When it happens, 2) how it happens and 3) who and where it comes from. 

For example, if your goal is to be a successful musician, with at least 1,000 loyal fans (according to Chris Anderson's Long Tail theory) in two years, that is attainable and within your control.

However, if you want your first gospel trap album to sell 500,000 units in the next year, you're going to be disappointed. Not because there aren't 500,000 gospel trap fans (maybe there are), but you not only used a time constraint, but a means and method constraint (via sales of your first gospel trap album).

If you are determined to use a means and method constraint (by being a specific kind of artist with a specific product/output, delivered in a specific way), you may need to relax on the time constraint. But first-time success later in life can be just as satisfying, if not more, than peaking in your 20s and 30s.

If you are not familiar with the story of Charles Bradley, please watch his documentary Charles Bradley, Soul of America (2012) on Hulu (link) as soon as you can. After working odd jobs and performing at small shows and being a James Brown impersonator for over 40 years, he released his first album at the age of 63 on Daptone Records, to critical acclaim and success. 

Here are more of my favorite examples of creative success later in life: 

Death (band)- Released their first EP in 1973, didn't see success until 2009, 36 years later. A Band Called Death (2013), an awesome doc about their story, is also on Hulu (link)

Leslie Jones- Started performing stand-up in her mid-20s, didn't get her big break until she became the oldest new cast member to join Saturday Night Live at the age of 47. 

There are other great examples, of course. Hit me on Twitter with your favorite success later-in-life stories with the hashtag #HWLongGame

You don't have to wait decades to be successful, but keep in mind that being successful how you want to be, exactly the way you want to be, exactly when you want to be may limit your dreams and make your path shorter, and less fun. Be open to all of the ways your story can unfold. 

Your Partner in The Long Game,
Chakka AKA Dab Calloway
Highwater Weekly Picks 

  • Storytellers: THREAD at Yale is a gathering of professional journalists and storytellers across mediums (writing, film, photography, etc). Part workshop, part conference, applications are open to career storytellers at any level.  Deadline is April 1.
  • Chicago-based Media Makers- The Chicago Digital Media Production Fund is currently accepting new grant proposals. The Production Fund is intended to support digital media works (web series, transmedia projects, etc) that encourage social change.  The submission deadline is Monday, April 18.

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