About Drew Tolbert
Big questions. Small-town Alabama.
I’m an Alabama author, speaker, and storyteller who spends an unreasonable amount of time asking one question:
How did THAT become THIS?
Who I am
I’m Drew Tolbert. I grew up in Corner, Alabama, a tiny rural community where directions could involve a church, a county line, and occasionally a landmark you probably should not put on a tourism brochure.
These days I live in Pell City, Alabama, and write about the strange little chains that turn ordinary moments into entire lives.
A conversation becomes a job. A job leads to a person. A family story becomes a tradition. Five forgettable minutes become something you would give anything to have back.
That is the stuff I keep coming back to.
I like pulling the thread
Most things have a story underneath the story.
A rule everybody follows had a first day. A family tradition started with somebody. Two people can remember the same event differently without either one necessarily lying. A tiny decision can travel twenty years before you finally understand what it changed.
I like starting with something ordinary, weird, funny, or slightly suspicious and following it farther than a reasonable person probably would.
Sometimes that becomes an essay.
Sometimes it becomes a novel.
Sometimes it becomes a keynote.
And sometimes I just end up three browser tabs deep wondering why we still say “hang up the phone.”
What I write
I write in a few different forms, but the curiosity underneath them is usually the same.
- Fiction — Character-driven stories about time, choices, relationships, and what happens when one small moment changes everything.
- Personal stories and essays — Writing about memory, small-town life, strange assumptions, family stories, ordinary decisions, and the things we call normal without remembering why.
- Humor and observations — The stories that begin with something ridiculous and somehow end up making a point.
I’m less interested in handing people conclusions than I am in finding a question interesting enough that we both want to follow it.
Books
I’m the author of the Oak Tree Series, including Under the Oak Tree, Leaving the Oak Tree, and Beyond the Oak Tree.
The series began with a simple question about time:
What if a few minutes had gone differently?
That question became a coming-of-age story involving friendship, regret, time travel, and the consequences of trying to change what has already happened.
I’m also writing Cornered, a humorous memoir about growing up in rural Alabama and discovering that the seemingly meaningless details of a life rarely stay meaningless.
Its central idea is simple:
Nothing is isolated. One small thing compounds.
Speaking
My speaking follows the same pattern as my writing.
Start with a story. Pull the thread. See where it goes. Then ask what it means.
I speak to businesses, chambers, associations, schools, civic groups, churches, nonprofits, and community organizations about the origin stories, memories, decisions, and ordinary moments that quietly shape the way we work and live.
My signature keynote, Why Do We Do It That Way?, looks at the rules, habits, traditions, and systems we inherit without always remembering why they started.
Other talks explore memory, small decisions, unfinished stories, and the five ordinary minutes that may eventually mean everything.
The weird résumé behind all of this
Writing and speaking are not the only strange stops on the road.
Professionally, I work as a workforce management consultant inside the contact center industry, helping organizations rethink how they schedule people, organize work, and solve operational problems.
Before that, I managed sales teams, worked as a private investigator, trained in crime scene investigation and fingerprint science, and spent enough time at Domino’s to become unusually fast at making pizza.
None of those things looked connected while I was doing them.
Looking backward, they make considerably more sense.
Which, honestly, is kind of the point of everything I write.
Still an Alabama story
Alabama is more than the setting for my work.
Growing up in Corner shaped the way I notice people, family stories, churches, small towns, strange traditions, and the little details that outsiders might walk right past.
Living in Pell City keeps me close to the kind of communities I still enjoy writing and speaking about.
Small places contain enormous stories if you pay attention long enough.
If you’re new here
You do not need to start by reading everything I have ever written.
That would be concerning.
Start with the books, browse an essay, check out the speaking page, or head to the Start Here page and see which rabbit hole looks interesting.