47. On Working Your Career Plan with Mark Herschberg

Overview

I was pleased to be joined by Mark Herschberg author of The Career Toolkit, Essential Skills for Success That No One Taught You, for a conversation on the importance of career planning and its ROI, assessing role and culture fit when job hunting, and the benefit of learning these essential skills throughout one’s career and with others in peer learning groups.

Mark is a model of being a multi-hyphenate, someone with a serious day job, an established "side gig," and many additional talents. He's certainly not one note and has a lot to share on career management from his 20 years of teaching at MIT's "career success accelerator."

In his book, via the accompanying app, and resources on his website, Mark offers a highly practical and insightful guide to the tools you need to manage a successful career over time. It's a toolkit you can pick up at any stage to support you in where you might be going next.

Thank you so much, Mark, for sharing all your great insights and learning with us!

More about Our Guest

Mark Herschberg is the author of The Career Toolkit, Essential Skills for Success That No One Taught You. From tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems, Mark has spent his career launching and developing new ventures at startups and Fortune 500s and in academia. He helped to start the Undergraduate Practice Opportunities Program, dubbed MIT’s “career success accelerator,” where he teaches annually. At MIT, he received a B.S. in physics, a B.S. in electrical engineering & computer science, and a M.Eng. in electrical engineering & computer science, focusing on cryptography. At Harvard Business School, Mark helped create a platform used to teach finance at prominent business schools. He also works with many non-profits, including Techie Youth and Plant A Million Corals. He was one of the top-ranked ballroom dancers in the country and now lives in New York City, where he is known for his social gatherings, including his annual Halloween party, as well as his diverse cufflink collection.

Topics Covered

  • We start by hearing Mark's own career story and what led to him establish expertise in the area of career management.

  • I probe on how he thinks about managing the two sides of his identity—being a Chief Technology Officer and being a career expert. In an honest reflection, he says that it does mean he has to put in twice the effort to brand himself in both these spaces, and yet still some people just aren't going to see him holistically.

  • Part of why Mark has this dual focus is that career planning isn't taught. He had the opportunity to fill this gap at MIT, his alma mater, and now more broadly with his book and speaking on the topic. Mark's advice—don't wing it! You wouldn't wing a project; why wing your career!

  • People get tripped up often with career planning, because they don’t think they can figure out where they want to be in the future. They tend to get overwhelmed instead of narrowing down choices. Mark offers questions in his book and on his resources page (see below for a link) to help people start to do just that, narrow down their choices.

  • I ask about having a longer-term vision vs. focusing closer in. He uses the analogy of a road trip. You'd never start driving without having a destination. For sure! So consider what you think your target might be and then backtrack your planning from there.

  • We talk about how Mark’s book and tools have application for people across all different stages of one’s career across the decades whether one is working in a company or going out on their own. As Mark notes, we are always growing in our roles and what those ask of us changes as we progress.

  • I love how Mark demonstrates in our conversation how career planning and investing time here delivers ROI. The payout will be there for the investment of time you put against career planning and management.

  • I ask Mark what the biggest blind spot people have around these skills, and he says that it’s that they think they can’t be learned. So, don’t stop yourself before you get started!

  • Given all the talk on the Great Resignation, I ask Mark about his section of his book about job optimization. I ask, because Adam Grant recently shared in a post that data shows when people leave for a new job, satisfaction and energy drop for over a year. Belonging dips, work-family conflict climbs. He notes that transitions can take a toll and suggests exploring ways to improve your job before you quit. Mark shares to first consider if one is unhappy is that driven by systemic or temporary factors. If you do want to optimize, think about whether or not the job is taking you where you want to go or think about other ways you can make the situation work for you.

  • Understanding a company’s culture is one of the areas that is often hard to uncover in job interviews and when seeking a new place to work. I love Mark’s tips here to uncover the true culture within an organization. First off he says to ignore what’s on the company’s website. Then he advises to ask the hiring manager to give you three adjectives to describe the culture and then ask them to provide an example that brings each to life. This is a great tip!!

  • Another top question to ask in an interview: if I were to ask the last person in this role what it was like and why they left, what would they say?

  • Mark shares what he has learned people tend to prioritize and what’s important at different stages of our careers.

  • I ask Mark if the parties he throws and is well known for are part of helping him recover and rejuvenate. Perhaps in part, but even more so they are a way for him to keep in touch with all the people he knows. What a great networking idea and approach! Take note!

  • His final piece of advice: create peer learning groups to learn these skills, and Mark offers a free tool on his website to help you create and manage these. Love this idea!

Resources Mentioned

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47. On Working Your Career Plan with Mark Herschberg

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2022Kathy OnetoRight Aspiration, Right Success