For 33 years I worked in enterprise technology, twenty of them at Trader Joe’s as Director of Computer Operations and Technical Services. Then I left and wrote 113+ books under my own name and ghostwrote 54+ more for other people. Nobody predicts that sequence, and I have watched it work in a room more times than any credential I hold.
The pivot is the story. It always is. A career with one turn in it has a spine a book can hang on, and a career with none has a résumé. I think of it as a river. A river that runs straight is a canal, and nobody writes about canals. A river that bends has a reason at every bend, and the reasons are the book.
Does a crooked career disqualify you from writing a book?
Most executives with one think so. They changed fields, or left something they were good at, or arrived at the thing they are known for by accident, and they assume a book needs a cleaner protagonist. So they either do not write it, or they write the résumé version with the bends straightened out, and the résumé version is the one nobody finishes.
Nobody reads a memoir about a plan that worked. They read about the year that made no sense, the decision that looked wrong from outside and right from inside, and the moment the person realized the earlier career had been preparation for something they had not chosen yet. The crooked line is the only part of a career anybody learns from, because it is the only part where a decision was made.
What did running IT and writing books have in common?
It took me years to see it. Read the system. Find the fault. Fix it. A director of operations reads systems to find where the process failed, and then fixes it under a deadline with a board waiting. A ghostwriter reads a life to find where the story is, and it is almost always at a fault line, the place where something broke and a decision followed. The data center and the manuscript turned out to be the same job.
I found the thread late, and only by laying the careers out in order and asking what I had been doing in each one. That is what an interview does for a client. Nobody has asked you the question that surfaces yours yet, and until someone does, the careers look like unrelated jobs instead of one job in different costumes.
What is a strategic memoir?
Your decisions, arranged so a reader can use them. Story where the story earns it, argument where the story proves something. The reader finishes knowing what you know and how you came to know it, and the second part is what makes the first part credible. A book of conclusions is advice. A book of the decisions that produced the conclusions is evidence.
The crooked career is ideal material for it, because every bend is a decision with a before and after. Why did you leave the field you were good at? What did you carry into the next one? What did the second career teach you that the third one needed? Those are chapters, and they write themselves once the thread is found. I describe the form in the memoir ghostwriting material on this site.
How does the thread get found?
By telling it in sequence, out loud, to someone who is listening for the repeat. The interview is where the client says the same thing three times in three different jobs without noticing, and the writer notices. The repeat is the thread. In my case it was reading a system to find the fault. In a client’s case it is whatever they keep doing in every role, the thing they would do for free, the thing colleagues eventually stop asking about because they assume it is just how the person is.
That thing is the book’s spine. Once it is named, every career fits on it, and the bends stop looking like detours. They look like the river finding its way.
Who is this for?
Founders who came from somewhere else. Executives with a second act. Anyone whose LinkedIn headline took three lines because the earlier careers refused to disappear. The messier the line, the better the book, because the book is made of decisions and a messy line has more of them.
It is also for the executive who has been told the crooked line is a weakness and has spent years explaining it apologetically in interviews. The book is where the apology stops. Laid out in order with the thread named, the crooked line is the most persuasive thing about you, and the case studies include authors who discovered that in the interviews.
Why the Trader Joe’s years stay in the bio
Because they are the turn, and the turn is what makes a reader ask how. A bio that reads writer, writer, writer is a straight line and the eye slides off it. A bio that starts with twenty years running IT for a grocery chain and ends with 113+ books makes the reader want to know what happened in between, and that question is the beginning of a conversation. I keep it in because it is true and because it does the work a bio is for: it makes someone want to hear the rest.
Your version of that turn is somewhere in your history. The job that does not fit. The field you left. The thing you were good at and walked away from. Find it and put it first, and then write the book that explains how the river got from there to here.
The river
A canal is efficient and forgettable. A river is neither, and every town that matters was built on a bend in one, because the bend is where the water slows and the useful things collect. Careers work the same way. The bends are where the person slowed down and decided something, and those decisions are what a reader came for.
I would not trade the turn for a straighter line. It is the first bend, and the book runs downstream from it.
Bring the pivot you still cannot explain to the Book Discovery Intensive. One engagement. You leave with the spine of your book, and usually a title, because the thread is easier to see from outside than from inside the river. My LinkedIn messages are open, and that is the fastest way to start the conversation. Part of The Memoir Hub.
Systems, then books. One job, two costumes. That is the book.
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