How Matt Syrett Has Thrived With Many Careers (Archaeologist, Investor, Trader)

by | Feb 15, 2021

Meet Matt Syrett. He is one of the most fascinating people that we’ve profiled in this newsletter. He has had several different types of jobs across many sectors. His ability to “connect the dots” between different worlds is both intriguing and inspiring. He is also incredibly thoughtful and self-reflective, and you’ll find his commentary below illuminating.

Matt’s careers over the years:

  • Archaeologist
  • Technical director at interactive agency
  • Running product at an ad network
  • Branding statistician
  • Senior product manager at Amazon
  • Helped launch a robo-trading firm
  • Film producer, editor, and screenwriter

On his motivations for many careers

“Three forces shape my life with multiple careers: marketplace instability, deep intellectual curiosity, and my ability as a polymath. My career path has been plagued by a lack of job security. I’ve have never been in a place where I could trust being in the same job or even industry for very long. The good news for me is that I have the rare ability and desire to pick up new skills and even whole professions on-the-fly to reinvent myself.”

Advice for aspiring multi careerists

“The biggest challenge of this kind of life will be explaining your career. I hate being asked what I do for a living, or trying to get a hiring manager or headhunter to believe that I am right for a job. The world likes to fit people into discrete boxes, and struggles with people like myself who are shaped as a square, round, and triangular peg all at once. When I do find work, I tend to find jobs that are impossible to be fill by anyone else. Jobs that require an odd mix of skills that should not exist in nature.”

On overcoming obstacles

“Every career transformation is a gut-wrenching setback that you need to rework into an opportunity. A magic trick you need to figure out anew each time. You overcome by not giving in to the grief, imposter syndrome, panic, and shame that often comes with transition. When I lost my last traditional job, it was an emotional blow, but I found the next thing by going home and just answering the phone from an old friend. By the end of the conversation, I was helping her leave her own job, start a company, and as a bonus getting myself a new job within that company.”

On how having multiple careers are mutually beneficial

“Benefited me? Yes. I like to think that I am the jack-of-all-trades guy you want around if there is a zombie apocalypse. Multiple careers work only if you transfer skills and knowledge from one profession to the next. It is impossible to keep learning professions from nothing. You can maybe do it once, but mastery from scratch takes years while adaption of skills from one domain to the next can lead to mastery much faster.”

On managing personal time

“I have a couple of life rules that help:

  • I make a sit-down dinner for my family every night
  • I don’t work in my bed
  • I value my sleep
  • I don’t say no to requests for homework help from my kids.

I once had a boss who would chastise me for leaving work on-time every day. I confused him by leaving on time and still being highly productive. How did I do this? I started my day hours earlier than everyone else in the office, so I could have quality time with my family.”

On what he wishes he had learned earlier

“That it will be okay. Early on, the transformations and life balance would be so stressful for me, but as I got older, I have become better about it – not perfect, but better. Be open, work hard, and a new path tends to emerge – maybe not the one you thought, but it will come.”

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On what to read

“Everything. I have been successful at this, because I don’t have a quiet mind. Any given week, I am pursuing some piece of esoteric knowledge that could be used somewhere down the line or not. To pursue new professions, you have to have a hunger for knowledge. So… learn history, coding, how to knit, bartending, archery… just keep learning. I spent an entire year commuting on New York subways reading books on obscure historic disasters, so I could better understand leadership in crisis. ”







On dealing with the stigma of having many careers

“Absolutely, there is a stigma. And, I don’t think I have overcome it. Sometimes I think I am un-hirable for typical jobs based on the fact that it is so challenging to understand my mosaic career. Increasingly, I am trying to find ways of hiding my experience rather than showing it to potential employers, which is so sad to me.”

On what to share with others about your multi-careerism

“It is most often best to be like a chameleon – adapting to become like your environment. Don’t confuse your audience with the complexity of your career unless you have to.”

On how to sublimate your ego at your day job

“Make your work about achieving a larger goal that is important to you. Sublimate yourself to that goal and not the job – you are doing the banal work to feed your family, pay for your art, make the world better, or whatever. Banal work is banal, because it lacks meaning. Your life is banal if you lack meaning too. Make meaning and the banal is not so banal anymore.”

A Day in the Life

“Beyond waking up at 6 AM, having a family dinner, and getting to bed around 11 PM, I don’t have a typical day. Isn’t that the point of a hybrid career? If I am writing or programming, I tend to like to do this work in the morning when I am creatively freshest. Otherwise, I take things as they come allowing time for exercise and reflection on the way.”

On what else you should know

“I am able to have multiple careers because I am dyslexic. This learning ‘disability’ is an asset to me in this life, since it favors loose connective thinking and requires me to be creative to navigate a world not designed for how I think. Early in school, I saw what my brother went through after his formal diagnosis as dyslexic, so I endeavored early on to hide my learning difference out in the open by: learning autodidactically, to avoid being labeled as disabled, and finding creative ways to excel in subjects that did not come naturally. It has given me a scrappiness and flexibility I have needed to navigate so many different fields.”

Where to find Matt


Kabir Sehgal is a Multi Grammy & Latin Grammy Award winner, as well as New York Times bestselling author of sixteen books. His debut feature film production Fandango at the Wall is streaming on HBO Max. Follow: LinkedInInstagramFacebookTwitterSpotifyYouTube