Unemployable! shares with readers your unconventional career journey with refreshing honesty, sharp humor, and plenty of hard-earned perspective. At what point did you begin to recognize that your varied employment history could become the foundation for a book?

When I first drafted what eventually became Unemployable! it was 1998, and I was fresh out of graduate school. I was starry-eyed and excitedly seeking the BIG THING that would become my lifelong career. It didn’t take long before I had accumulated a LOT of rejection letters. At that time, I was 28 years old and already had quite a few interesting job titles in my past. I thought that I would write a job hunting manual while I was job hunting, and at the end, I would have a job, plus I’d have written a guide to help others! I planned to open each chapter with my cover letter and end each with that job’s rejection letter. I was searching in many fields already, as my varied background and interests (early-onset multipotentialitism) made me interested in the wide variety of industries I was capable of thriving in. As I talked to my classmates and friends, I found that my mindset was unique, at least in the way I spoke of it. But in conversation, I often ran into other people with a similar issue in finding just one career path, and I thought that my book would be a perfect vehicle for everyone out there who was trying to find their way.

Fast forward to a few years ago when I picked up the early outline of the book after setting it aside for decades. I had many more jobs and careers and paths behind me. Plus, I had accumulated the knowledge and wisdom that comes with aging. I realized that while I hadn’t changed at my core, job hunting had become a different beast over those years, and I wanted to tackle the subject from a new angle, one in which the reader feels seen and knows that while their trajectory may be wild, their achievements are no less valid. I had a lot of personal stories to add and decided to write it in a more narrative and conversational format, adding some tools along the way, instead of making it a straightforward job hunting manual. I think it’s by far the best (only) book I have published!

You’ve worked in a remarkable variety of fields. What have those different roles taught you about your strengths and abilities?

I can tongue-in-cheek list some things that make me a unique employee, like my ability to handle a giant snake, or blow things up, or find the perfect Halloween costume for you and your friends. While those are true, I think what a varied background has brought me is experience dealing with a lot of types of people in a ton of interesting settings. “Dealing with people” seems vague, though. I guess I would say it is more that I have learned to understand personalities, motivation, collaboration, and honesty. Some of these traits were observed in not-so-great settings, while others were shown to me by mentors and colleagues who were generous with their time and energy.

I think a strength that I have carried with me from the very beginning was my authenticity. Being true to myself didn’t always land the way I hoped, and was not always valued in an organization that was more rigid, but I have always tried to put my best foot forward, even when it was not well-received. Many people I have worked with over the years are still my friends, which to me says that they value ME and don’t care so much about inauthentic performances in the workplace. In the book, I talk about a very in-depth application process I went through recently, where I had to track down dozens of former coworkers and bosses to get them to talk to the interviewer about me. It was a very enlightening experience, one in which I was happy that I was able to go back 30+ years and still have so many people say that they think I was a good person, a good employee.

What challenges have you faced when explaining your diverse professional background to potential employers, and how can people with unconventional career paths better communicate the value of their transferable skills?

Getting my foot in the door to get an interview has been the hardest part. Especially as technology came online and resumes were scanned for certain items in order to get rid of outliers, like myself. One thing I am glad I did is form an LLC many years ago, where I can group a lot of my jobs and employers, with the length of employment remaining long enough to keep me as a candidate. I do know how to play the AI resume system and at least get a phone screening, which isn’t necessarily a skill I want to have or want to use, but it is the world we live in now.

Once in the room, or on Zoom, it is so much easier to talk about diversity and how it relates to their organization or position. So many components of jobs I have had relate to other jobs, but on paper, it doesn’t make sense. In a conversation, I think that I must intrigue people on some level, as they want to keep having conversations with me even if they aren’t immediately offering me a job. It could be that I promise I will bake sourdough if I am hired (yet another past career), and who doesn’t love sourdough?

To communicate the value, those who are able to talk to interviewers in person have an advantage because we multipotentialites are (imho) both interesting and engaging. Take your wide assortment of skills and experiences and channel them into concrete examples, moments you achieved a goal that show you understand the role. That’s something truly amazing. I know I give a lot of props to being someone with a nontraditional background, but I truly believe it is something outstanding that has been overlooked and needs to be seen as a valuable asset.

What changes would you like to see in the way employers evaluate candidates with employment gaps or unconventional backgrounds?

I have more than one chapter in my book about this question. There is a full chapter specifically for HR and recruiters, which is a bonus chapter I added even though my editor said that recruiters won’t be reading this type of book. I went ahead with it because I think recruiters have best friends or moms who will have read my book and want them to read it, especially the chapter I wrote just for them. (Hint: It makes a great gift!)

I digress. There are many changes I would love to see when a multipotentialite person like myself sends in a job application. First, I wish that AI did not screen for length of employment. I think this does a disservice to someone who is a very competent person who gets into a role and either masters it quickly or quickly realizes that the fit is wrong and moves on. The ability to know when things are not right is a key component of being an excellent employee, and will pay off in other ways, like being able to evaluate multiple issues within an organization and come up with solutions.

There’s an even simpler solution I will share with you here, directly from Chapter 55, “Mind the Gap,” in my book. It’s a freebie for anyone reading this interview. (You are welcome!) In an interview, I would love to hear, “Tell me about a time you were doing something other than working in this field.” Follow that up with “What did you learn from that?” I believe the insight that someone with a less normal career trajectory will bring to those answers tells a great deal more than “Tell me about a problem you solved at work.”

The big secret is, and I tell you this because I care deeply about everyone having positive experiences in their careers, that someone who is a multipotentialite or generalist is in fact the best and most engaged employee you can have. There are areas where the fit is wrong, but when it is right, there is a power and energy that comes along with trusting this type of person to represent your business. If I had my own business, I would first seek out people with a more varied background, as I think that the ability to find the stride and create excellent workplaces is a natural thing, making that organization unique, desirable, and amazing to be a part of.

Author Links: GoodReads | Website | Substack | Amazon