PR Mark Herschberg | The Career Toolkit


Many people say we need a lot of different skills for our career path, but has anyone ever actually taught you these skills? That’s what Mark Herschberg discusses today. Mark is a CTPO, Speaker, MIT Instructor, and Author of The Career Toolkit, Essential Skills for Success That No One Taught You. In this episode, Mark shares the career skills, tools, and approaches that are often undervalued and underutilized but are actually essential, especially in this generation. He also discusses in-depth resilience and what it looks like in the tech world. Tune in now and learn the essentials for your career path!


Show Notes:

  • [01:27] Mark Herschberg’s Past
  • [08:28] Renaissance Weekend
  • [12:47] Pivot
  • [15:18] MIT’s Career Success Accelerator: The 10 Essential Skills
  • [15:29] Section 1, Chapter 1: Career Planning
  • [15:49] Section 1, Chapter 2: Working Effectively
  • [16:01] Section 1, Chapter 3: Interviewing
  • [16:25] Section 2, Chapter 1: Leadership and Management
  • [16:32] Section 3, Chapters 1-4: Communication, Networking, Negotiations, Ethics
  • [18:05] Leadership is Not Atomic
  • [19:40] The Reason Behind the Bankruptcy Code
  • [23:17] Why We Have Rules
  • [31:08] How Companies Approach Culture
  • [44:52] There Is A Change

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The Career Toolkit: Essential Skills For A Resilient Career In The Tech World With Mark Herschberg

On this episode, I have Mark Herschberg. Mark is the author of The Career Toolkit: Essential Skills for Success That No One Taught You. Educated at MIT, Mark has spent his career launching and fixing new ventures and startups, Fortune 500s and academia. He’s developed new software languages, online marketplaces, and new authentication systems and tracked criminals and terrorists on the dark web. Mark helped create MIT’s career success accelerator, where he’s taught for more than twenty years. You’re going to love this conversation with Mark Herschberg. Enjoy.

I’m rubbing my hands together because I already can tell that there’s going to be so much meat to what you and I can talk about. It’s going to be a question of how much is going to be enough to satiate us without either of us becoming so bloated that we want to take a nap afterward. Your bio is extensive, and your history is impressive and all that. My question to you is, what’s one thing that is not a part of that introduction, your standard bio, that you would like people to know about you at the start of our conversation?

I’ll throw in a little extra. I don’t know if you really need to know it, but I do some standup comedy. I started doing it years ago just to challenge myself. I’ve done a lot of public speaking, but comedy is a different type of public speaking I had never done before. I always like to push myself. I always like to grow, so I started doing that.

You’re surprising me. I didn’t know that. I didn’t expect to hear you say that. I can feel the terror. I am a keynote speaker on a daily, weekly, monthly, and yearly basis. I speak to audiences all over the globe by thousands, yet just the thought of standing up in front of a room full of people and with a goal that I lead them in laughter. I’ve done this with audiences before. I actually did this with an audience of lawyers at a bar association meeting that I led, one of these continuing legal ed things. I’m a fully recovered attorney myself now, having spent eighteen years doing that work. I led them in an intentional laughter session for a couple of minutes we would be laughing together. Otherwise, to create laughter in a space through storytelling and things terrifies me. You got to let us know. Mark, how has that been going for you? What has that been like?

It took me by surprise when I started because I thought, “I’m a reasonably funny guy. I post funny comments on Facebook sometimes, so I’m going to go do this. I’ve done public speaking. I have no problem doing that. Let me go up and do some comedy.” What I learned very quickly is a few things are subtly different. First, standup comedy, as one of my coaches said, “You’re not going for smiles. You’re going for belly laughs.” You have to have a laugh-out-loud moment every roughly 30 to 60 seconds to keep them going. Not just, “That was cute.” No. Laugh out loud. The other thing as public speakers, we know our content, but we also know you don’t memorize it word for word.

You have your flow, and it needs to feel natural, but when it comes to comedy, you need to have it memorized, not just word for word, syllable for syllable. Emphasizing the right syllable, increasing or decreasing a pause, or even changing a word from a one-syllable word, those subtle changes can make or break a joke. I never appreciated that before.

PR Mark Herschberg | The Career Toolkit

The Career Toolkit: Subtle changes like emphasizing the right syllable, increasing or decreasing a pause, or even changing a word from a one-syllable word can make or break a joke.


It’s working with a bunch of other great comedians that, over the years, I learned this. I learned to get my timing better. My timing is still my biggest weakness, but it’s been very informative. What’s great is that when I do my more commercial speaking gigs, when I speak to companies or conferences, I’ve always had some humor I could fire off a quip. Now when I have more intentional humor, I’ve learned how to construct that part better and bring in these new additional skills to elevate the other work that I do.

I got to keep going down on this track for a little while longer. I know we have an agenda about this other business conversation. We’re going to talk about tech startups and career tools and business tools for leadership management. We are not going to go there yet. First of all, when you do a set, I want to know how long is a typical set for you when you get up there and go and what is the typical content you’re bringing out.

This is an important question. I don’t go to traditional comedy clubs. I don’t know how well I would deal with hecklers. That’s a very important skill that I have not yet tested. I typically do sets that are, sometimes I have to keep them short when I’m part of a group doing it. It might be as short as three minutes. We try to go for about 5, 6, or 8 minutes. That’s usually a good set for me.

The professional comedians who are doing 20-minute, 30-minute sets, or 1-hour-long sets. The comedy I do is a lot of monologues. I’ve got friends who do different types of things. Imagine I was standing up on that late-night talk show. I am pulling in from the headlines, things that have gone on, and that goes into my monologue.

It means I’m changing it very rapidly because it gets stale and out of date. You might be able to use something for weeks or months. The other thing, the group that I primarily do this with, is a group similar to a TED Talk audience. The great thing is I can make references to the periodic table, Chaucer, or some other reference that probably would not work in your average comedy club but works well for this very educated audience.

It’s a bit like a curated karaoke night for a group of folks that are there to support one another. Is that fair?

That is fair. I do it with a group called Renaissance Weekend, which is like a version of TED Talks. You’ve got extremely educated people and very supportive people. They’re never going to boo me. They’re never going to pull me off the stage. They will applaud me even if I screw up. There is a safety net, which is nice because I’m still early in my comedy progression.

Have you ever done a TED Talk?

I have not, and I don’t have a desire to.

You don’t have a desire to.


I’ll just say this, whether you don’t, or maybe someday you do. For you, you chose this as a challenge, and standup comedy is probably one of the greatest feats of a daredevil that I can imagine. Literally walking on a tightrope. To me, it’s at that level. Doing a TED Talk is something I have had the experience of doing, and actually, a part of our company trains people to deliver TED Talks.

In part because that was a challenge for me similar to the one you chose for yourself. I’ve been speaking to audiences for many years all over the globe. To have a set, in this case, a TED talk for that time period was eighteen minutes. Now, they’re 8 minutes and 12 minutes, and stuff like that. When I did mine, it was pretty standard with eighteen minutes.

To have an eighteen-minute talk end to end, completely not just memorizing, it’s embodiment is what it is. You are embodying the words, the message, the intonation, all the variants, pauses, and dynamics. Every aspect of it. The facial expression. The whole thing at a certain point, maybe midway through the process of crafting it. Figuring out what I wanted to talk about, all of it.

I said to my wife, “I don’t know if I can go through with this. I don’t know if I can do it. I don’t know if I have enough brain cells left, frankly, to actually pull this thing off.” It was just magical. It was a completely different dynamic than other forms of public speaking. I’m going to give this some consideration. For a lot of reasons, it’s a very strong process. People right now going, “When are we going to get to the business stuff?” This is interesting. Give me something I can use with my team.

This all relates. If you think about what we’ve just done. We’re both professional speakers, so we’re used to going up and having unstructured. Whether it’s a TED talk or a comedy set, it’s very structured. We’re stretching ourselves in new directions. Just like before you go onto the field, before you play a sport, you’re stretching yourself. You’re pushing your muscles in new directions, so you’re warmed up and ready to play and be active.

By stretching yourself, by putting yourself in certain arbitrary constraints, I have to have this word for word. The pauses really do matter here. That feels artificial. What happens is when we are in a meeting or standing up before our peers at the whiteboard, and we’re doing a more spontaneous talk, we’ve stretched ourselves. We’ve pushed ourselves in these directions, and we’ve got some of that latent muscle memory within us that we can apply to our daily practice at work.

What we’ve just been talking about, it seems like it was fun, but we’re talking about building up skills. We haven’t talked about speaking, comedy, and formal prepared talks, but this idea applies in all sorts of areas. Pushing yourself in some direction gives you the flexibility to be more productive and agile in your work.

Pushing yourself in some direction gives you the flexibility to be more productive and agile in your work. Share on X

It does. It’s not an either/or as well. It’s “yes, and,” both. This ability to get into a structured mode and be able to succeed with a structure is so vitally important, as well as the capacity to utilize what is in the space. There is one of the things when we were working with folks that wanted to do less structured talks.

For example, a talk where you’re not memorizing every word, even in a keynote. As you said, all of us that do keynote work, understand that there’s a structure and a theme following a certain through line, but we’re not going to say exactly the same thing each and every time. You have to read the energy in a room.

The most effective public speakers are those that don’t come out there like a robot but rather truly read the energy in the room and then can adjust or be agile, as you said, a shameless plug for my book, Pivot, be able to pivot at the moment and utilize what it is. That principle comes from improv.

One of the other things that might challenge you, and I’ve done a bit of, but want to certainly do more of, is getting involved in improv groups. It’s the concept that you basically take everything as “yes, and.” If somebody says something and you say yes, you move with that thing. You utilize what is in the moment, whether it’s the physicality of what’s happening, or the words, or the tone, or any of those things, the pace, and you simply take it to the next level. You think about it as an entrepreneur. Here’s our segue into business entrepreneurship. Being an inventor, a startup founder, and all aspects of innovation involve that same capacity to “yes, and.”

In other words, to plus whatever is happening, not to waste any of what’s going on, but actually utilize it. When we’re living in a world of tremendous change and disruption like we are now, at least some of the conversation is, “How do you yes, and? How do you plus everything that’s happening in the world now, so 3 or 5 years from now, you, your business, and your teams are thriving well beyond even the point that they might be thriving?”

I’d love to get a sense from you. You’ve been a tech startup. You are a founder. You’ve not just studied at MIT, but you’ve been a professor there. You’ve taught there. If you are educating a group of young founders right now, let’s tease out some of the most important tools that young founders may need to have that they don’t maybe have because it wasn’t taught to them. It’s certainly not maybe taught in business school or what have you. Can we start there? Is that okay, Mark?

Let’s start with a high-level set of skills but also a mentality particular to founders. There are ten skills that we have seen over and over again when universities survey employers, when large recruiting firms survey employers, and when companies internally do assessments. Over and over, we see a consistent set of skills listed.

If you look from one list to another, they might use slightly different terms. They might say, “It’s fourteen things. It’s eight things,” depends how they break it down. Here’s what we’ve done in the class I teach at MIT, which I refer to as MIT’s Career Success Accelerator. In the book I created, I break them into 3 sections and 10 skills. Let’s run through what those are. Section one, Careers. Chapter one, Career Planning: How to Create and Execute a Career Plan. Now, even if you’re a founder, you still need one. You might say, “I’m not getting promoted. There’s no new title.” It’s not just about the title. It’s about your capabilities and competencies. Create a plan to improve and get there.

Promotion is not just about the title; it's about your capabilities and competencies. Share on X

Chapter two, Working Effectively. We’ve been taught in school how to get the right answer and stick it in a box. In the real world, there is no box. It’s about knowing the right questions to ask and dealing with corporate culture and politics. Those are very important skills that we never talk about. Chapter three, Interviewing. There’s lots of content, “How do you answer this question? How to make a good resume?” but we’re never trained how to interview other people. Many of us, certainly founders, not just leaders, even peers, have to interview our peers. No one’s taught us how to do that.

Second section, Leadership and Management. It’s the basics of leadership, and then management, I look at from the people side and the process side. The third section has four chapters. Communication, Networking, Negotiations, and Ethics. Time and again, we see these skills come up. If you’re founder, in particular, the most important thing is to recognize that whatever you’re doing, it’s not just you. It feels that way. We’re the person trying to get everything done, and the buck stops here. You need to recognize that it is your team, and it’s not what you can do. It’s what the whole team can do, whatever anyone on the team can lead you forward to, and you have to take more of that team mentality.

That makes total sense. I probably missed something. This is taking me back to my college days when I would literally be looking at my right or my left. My left actually now my wife, then my only helpful girlfriend. I would look at her and said, “Did you get ten things? I only got eight.” Here’s what I got. Mark, I got career planning, working effectively, interviewing, leadership and management. Maybe that was two things, not one. Communications, networking, negotiations, and ethics. What did I miss?

Leadership, people management, process management.

Got it. Thank you. This is good. Somebody out there is going, “I didn’t get it either.” That’s perfect. I’m going to ask you some questions about this professor. If you had to pick one thing, you’re on a desert island, one tool, one skill you could take with you. Is there one that would be more important than anything else there?

I get asked this a lot. It’s a really important question. One of my most popular articles is titled, Leadership is Not Atomic because it’s not leadership. More important than communication, more important than something else. If you are going to be a good leader, you need to learn how to negotiate with other parties. If you’re going to be a good negotiator, you need to learn how to communicate, how to set your position, and how to listen to others. All these skills build upon each other. You can’t just say, “This one skill in isolation” I know I’m bypassing a question a bit, but they build upon each other.

PR Mark Herschberg | The Career Toolkit

The Career Toolkit: If you are going to be a good leader, you need to learn how to negotiate with other parties. If you’re going to be a good negotiator, you need to learn how to communicate, how to set your position, and how to listen to others. All these skills build upon each other.


Now, I get to do what I did pretty well as an attorney for many years. That is to take the opposite side of it, the contrary position. I’m going to pick ethics, which is an interesting thing for me. I had a conversation earlier. I’m drawing on what’s in the space for me. When I was a lawyer, I made a lot of money, and I don’t have any shame about saying that. I was not terribly fulfilled. I was at the beginning of my career. I was a bankruptcy attorney at the start.

It might sound funny because you go, “All you’re doing is dealing with people and situations that went bad and went sideways. That’s how it ended up in bankruptcy. What’s so great about that?” I’ll just say that the relief that I was able to provide to business owners and folks in that space was phenomenal. I understand why they created a Bankruptcy Code because it truly is a way to clean the slate. Nobody wakes up in the morning and goes, “I want to scuttle my business today. I want to ruin all my relationships with everybody I borrowed money from. I want to lose everybody’s money.” Nobody does that.

Everything starts out as a great idea, and then the reality is that it’s not always a great idea, or the execution was off, or whatever. Sometimes those things end up in bankruptcy court. The relief was great. I felt fulfillment from that. I moved out of that into more commercial litigation. Ultimately, I would say there was a trade-off between the fulfillment side of things, including the financial fulfillment, and the ethical compromises that showed up in the space for me.

When I transitioned out of the law after eighteen years and began to do different work, which is what that book Pivot is all about, which is about career reinvention, I found what has sustained me and buoyed me ever since then. Even make sometimes more, sometimes less money than I did previously, that not being the most important thing.

Having a 10X fulfillment factor involved, “I’m so fulfilled by the work that I do, and this is interesting.” In finance, you want to move your bottom line exponentially, increase your turnover, and decrease your expenses. Very simple stuff. To me, I increased my fulfillment and decreased my ethical compromises in the work that I currently do, which is why a career was a great fit for me. I want to hear your thoughts on how deeply you dive into ethics with your folks and how important you feel it is to the success of a startup.

Sadly, our society is set up that ethics aren’t important and sometimes get in the way. If you think about cryptocurrencies, for example, think about companies like Airbnb or Uber. They very intentionally cross lines. Uber said, “We’re going to start up effectively a taxi service.” Taxi services are regulated by cities.

Say, I want to be a taxi driver. I have to pass certain tests and background checks. I have to show I’m competent and then get a license. There are some arguments about this term called rent-seeking in economics. They create these barriers. A New York taxi medallion. The license you needed to drive a New York taxi cab before 2008. It was going for around $750,000.

Think about what a taxi driver earns. They can’t afford to buy that. You take out a mortgage effectively. These are assets. Just like you got a mortgage for a house, you get a mortgage for this. We can argue about whether they were too restrictive and whether there were some inefficiencies in the space. Those might be valid arguments.

This company, Uber and others just said, “We’re going to outright ignore the rules, and we’re going to put drivers in cars. Here’s a thing. We’re so small. Who cares? Maybe they will shut us down two weeks from now. Okay. Probably we’re not even on a one’s radar.” By the time they got big enough and got on people’s radars, they had made enough money, raised enough, if not earned enough that they could then hire a team of lawyers to push back against it. What we’ve seen is, unfortunately, a lot of startups will say, “I’m just going to flout the law and hope I get away with it long enough until I can afford the lawyers who can give me a defense against it and push the boundaries.”

Ask for forgiveness instead of for permission.

I would say I do not do that. There’s a reason we have these rules. One of the things we’re seeing is there are reasons. We see problems with Uber drivers who assault their victims because we didn’t do background checks. This is a problem. Every regulation we have is because someone at some point did something wrong, and we need to be explicit about it.

As you grow up, whatever stage you are in a business, ethics are always the last thing we think about. “Are we making money? Is this sustainable? Can we do all these things? By the way, is this illegal? Is there a problem? It’s a little bit of a problem, but the amount of money compared to the amount of problem, I’m willing to overlook it.”

What we need to do is set up ethical guardrails, lines where we say, “Here are the boundaries.” If we start to get near that boundary, we take pause and say, “Wait a second. We’re getting close to this guardrail here. Let’s think about this. Should we be doing this? Maybe the guardrail is in the wrong place. We haven’t thought about this case, and it’s okay to move it.” You want to be conscientious. You need a priority. Set up those guardrails and talk about it with your teams, “As we get close to these boundaries, this is where we trip something, and then we have a discussion.”

Do you have an example of any of the startups that you’ve been involved in? I know there have been several where this has been a real consideration. Not just a thing that we teach in a class.

I’m trying to think about the ones I can speak about.

I was thinking that, too. I still wear the lawyer hat often. Scan and see if there’s something that comes up.

Here’s one mistake I made that I talk about. I was at a company. The VP of product sexually harassed one of his employees. It was a case I remember. I knew something was going on, but I didn’t have the details. He and I went out for a beer. He said, “Do you know what’s going on?” I’m like, “No.” Clearly, something’s off.

He told me a story and his statement. He had gotten a young woman to transfer into his group from a different group. They had been friendly. She transferred into his group. He apparently asked her out on a date. She said, “No.” It spiraled from there. His statement to me, I will never forget this. He said, “It wasn’t my fault. She was sending me signals.” This is stupid defense 101.

“It’s not my fault. It’s all her fault.” I was horrified by this, and I thought this was an open-and-shut case. He’s not denying it. He was very clear. There were some electronic records of this. I’ll wait for inevitably him to get fired. I was a few months into this job. I just started. The investigation went on, and they gave him a slap on the wrist.

In fact, he was temporarily removed from his position. He was not running a team. She left the company. A few months later, he’s running the team again. It shocked me. How did this not get resolved with him getting fired? I was still relatively new to the company. I didn’t want to change jobs so I stayed. It was a bad situation for me personally because I lost respect for him, and that was evident. Also, this was not a good organization to be part of.


I should have walked away earlier. That was to take on my part that my guardrail should have been if there is sexual harassment and there is not a clear, strong consequence for the person who created the infraction, what does that say about other decisions this company will make? As a slight epilogue, one of the CEO and this guy went on to do another company.

He sexually harassed someone there. I happened to be talking about this first incident with some friends years later at a conference, and they had no idea. When word got out, he was at this other company. It came out he actually was dating an employee there as well, which got him still only a slap on the wrist. Later, when he crossed some other lines, he eventually got fired.

We see this. If someone is willing to cross one line, not with sexual harassment but with other things like, “I didn’t realize this wasn’t allowed,” or a gray area’s not obvious. Their intention was reasonable. That’s different. When someone is clearly crossing a line, as was this case, just walk away because they will do it again.

When someone is clearly crossing a line, just walk away because they will do it again. Share on X

I went to a movie with our youngest daughter the other evening. We saw the movie She Said. I won’t ruin anything for people who haven’t seen it, but it is about the New York Times coverage of Harvey Weinstein. At the same time, when New York Magazine was also with Ronan Farrow was also investigating.

What’s interesting there is that many of the people around Weinstein were aware. It’s a similar situation to the one you just described. People were aware. Perhaps enabling, not perhaps in many cases enabling that behavior because there were no consequences. It’s not the not doing something about it. It’s the not doing something about it that actually contributes to the ongoing damage.

Clearly, the board of directors or the organization itself has ever been brought up on any kind of charges as a result of it. That’s a conversation for a different episode. In seeing the movie, and of course, the movie is an artistic expression in someone’s opinion, I get that. It’s not necessarily black or white, but from everything we can tell, this is factually what occurred.

People turned their back on something and violated that ethical code. What I want to bring to the table for this discussion, in addition to the ten skills that you identified, there’s something that could be an eleventh that I want to bring up. I want to ask you. Where does culture fit into this? As you said, it’s in an organization where there’s some lack of vigilance about ethics where you’re willing to overlook something because somebody’s a performer.

They’re great at their job, but they also happen to be misogynists or racists, the best salesperson we’ve got, or whatever the case might be, or they’re the founder. That ethical violation or that sensibility creates a certain kind of culture. I think that’s what you were speaking to. The culture then takes on the smell of that sort of thing.

It does. I talk about culture in chapter two, Working Effectively. If you think about how companies approach culture, if you were to ask someone during the interview process, “What’s your company culture?” they’re going to point to their website where they say, “Here are our six values. Customer first. Always innovate. This and that.” Maybe that’s their culture. Maybe not.

Sometimes, it’s just what marketing puts up there. Sometimes they intend it, and they don’t always live it. Sometimes they do live it, but that’s not your full culture. Those are your values, but it’s not your culture. Your culture is how you operate day-to-day. Your culture is you don’t challenge the boss in the meeting. He doesn’t like it.

Your culture is, “We like to have open debate during meetings,” versus a culture of, “You should resolve this before the meeting. The meeting is where I’ll come together and rubber stamp it.” They’re both valid cultures, but they’re very different. I have one colleague who said his culture was whoever yelled the loudest wins. That’s how it works. Your culture may be one of, “We don’t really plan. Everything is fighting fires,” or culture of, “We have seventeen meetings to have the pre-meeting before the meeting for the planning meeting for the seventeen meetings afterward.”

Some people are nodding their head now and going, “That’s the culture I work in.”

Those are our cultures, and none of those are listed on your website. Most of them are not intentionally designed. They grow up organically. It’s fine to start organically, but then you want to be intentional, saying, “Is this a culture we want or do we need to intentionally change it?”

That intentionality is so powerful. The thing that I want to offer that maybe you make an asterisk or a bonus skill and I want to talk to you about is resilience. I don’t know if resilience shows up in any of these other ten or whether it’s truly a separate category. I want to get your take on that, Mark. Let’s start with how you define it, if you don’t mind.

The reason I’m doing that selfishly is because I can add you to the list of people we’ve asked that question to, which is over 5,000 folks who’ve taken our resilient leader assessment. That’s a way that we get to determine their definition through this three-minute assessment they take. I’m going to ask you more directly, how do you define resilience for yourself?

My definition comes from my friend, DJ Skelton. If you don’t know who DJ is, he was named GQ’s Badass of the Year. DJ is an incredible guy. He went to West Point and got wounded in Iraq. He is, I believe, the most wounded soldier to go back into the field, yet he is still one of the nicest people. Despite all the challenges he’s gone through, he is one of the nicest people I have ever had the privilege to know. He’s just an amazing person.

From all the physical and emotional setbacks he had to get back on the battlefield, from literally having his life nearly taken from him to get back on the battlefield, we’ve talked about resilience, and he’s definitely a better expert than I am. He gave me a very simple definition, which is resilience is how quickly you can get back to where you were. That’s how I think about resilience.

I say quick, but implied in that word is perhaps other cost. I might be able to do it in a few weeks. What’s the emotional toll it took to do it in a few weeks versus a few months to get back to where I am? Is it just, “Physically, I’m able to do something or a company’s backup to this revenue level?” Is it some of that other, “Are we emotionally there, or do we still have anxiety?” There are some subtleties in those words, but that starting definition is a good macro way to look at it.

Part B of the question is, where does it fit in the list of ten, if at all? Can I influence you to include that in your curriculum going forward? Let’s talk about that.

First, we said these are fuzzy. It’s not even clear where leadership end and communication begins. We also know that some people say, “No, these are six skills. No, they’re twenty-three skills.” It depends on where you draw the lines. I would say there are a lot of other skills that either fall under these buckets or maybe not even under these buckets that are still important.

We just don’t see them come up as much. Resilience would be one of them. You could argue flexibility and innovation. Certainly, we don’t want robots. We want people who can innovate. You might be saying, “You didn’t mention innovation.” I would say there are a number of other skills, but in some sense, they’re not quite as universal.

I’m not saying resilience is a niche skill. When you think about certain jobs or someone who’s a waiter, resilience probably is not quite as important to them. Whereas communication, being able to communicate with your customers would be. Understanding how to deliver customer value. Understanding the culture and the value you provide. That would be from chapter two, would be. You could argue waitstaff nowadays. They get yelled at by customers daily, and you need the resilience to deal with it. It might just be what lens you’re looking through.

Sure, and being on your feet for hours on end, making very little money, and then making ends meet, even in the face of that, which a lot of these folks have multiple jobs and maybe have kids at home. I don’t want to digress there. For now, I want to ask you, in your career, what was the most challenging time, and if it was a time or an event. To me, what I really want to get at is, was there a moment when you thought, “I may not make it through this. I may not get through. This might be the end of me, the end of my career.” Scanning your own experience in life, is there a moment that comes out for that?

I’ll give you two, and there are lessons from both. One of them, I took off the summer of 2008. I was consulting at the time. I said, “It’s the summer. The labor market slows down. I’ve got savings. I’m just going to relax this summer. I’ll start looking after Labor Day.” What happened in September 2008?

Lehman Brothers went bankrupt. That’s what happened.

Financial meltdown. Start of the Great Recession. The biggest financial challenge. The biggest labor challenge in a generation.

Maybe since the Great Depression.

Labor market dried up. There were just no jobs we had. I’m thinking, “I don’t have a job. I’ll just use all my savings. I have more savings, thankfully, but boy, this is not good.” I was walking along the street. I saw a street performer, a busker. He plays music on the street, and you put money in the cup. As I’m thinking, “What’s going to happen to me? How long am I going to be unemployed? Is this the Great Depression? Am I going to be out of work for five years? There go all my savings, and I’ll have to you give up my home.” I walked past this busker and looked and said, “I am so much better off than this person.”

I don’t mean that in a condescending way, but I thought, “I have a college degree. I can always take a lower-level job. I do have some savings. I’ve got my long-term retirement savings. I also have friends and family who are a part of my support system. I’m lucky I still have a good relationship with my parents, and they’re still alive. I know if the option was to sleep on the street or on their couch, they don’t want me moving back home, but they’re not going to have me sleep on the street.”

I have built up a safety net. Not just financially and educationally but with my support system. That was going to protect me. I said, “No matter how bad it gets, I’ve put in the work to put myself in a relatively bare position, economically, not in terms of our own self-worth and value, that I will be okay.” As a side note, the other thing I realize is every time I walk past a busker now, I always give them money. I said, “They are working harder than I am in some situations and have a lot less certainty.” I always give them a dollar.

That’s the first scenario.

The second one, I moved to New York. I had been living in Boston for about fourteen years. When I moved to New York, that was really a big transition for me. I moved in, and I was having trouble finding an apartment. The apartment I thought I had found was taking weeks around to get back to me. I’m like, “I don’t even have a place now. I might not get this one.”

I was staying with my girlfriend, who didn’t want me living with her at the time. On the job I took on day two, there were some strong red flags. I just knew on day two this was not going to work out. I gave up my apartment. I gave up the stability, the life I knew. I came down for a job that I knew wasn’t going to last. My girlfriend actually tried to break up with me. We had a volatile relationship on and off. I remember saying to her, “I gave up my apartment. This job may not work. You can’t break up with me right now.” She said, “Okay, fine.”

The job lasted a month. It was just, “Was I going to find a new job, or was he going to fire me?” It was a race for what that would be. He fired me first. Everything in my life was changing. It was a scary time. Thankfully again, I had built up all these support networks. It’s not just money in this case. Through my girlfriend, I got connected to a guy who connected me to a guy, and I got a VP of Engineering job that was even better than the job I came down for. If you do the work, build up your network, experience, education, skillset, and this capability, what you’re doing is you are creating a cushion or a safety net for when this volatility does hit you.

PR Mark Herschberg | The Career Toolkit

The Career Toolkit: If you do the work and build up your network, experience, education, skillset, and capability, you create a cushion or a safety net for when volatility hits you.


You couldn’t have done any better as a lead. I appreciate you doing that. The scenarios that you just described were the kind of scenarios that I envisioned when we started to research this book, Change Proof: Leveraging the Power of Uncertainty to Build Long-Term Resilience. How do you utilize the unknowns, the uncertainty that is ever more present in our experience nowadays?

You shared with us some of the more common ways that we experience uncertainty in both of those cases. You also gave us a very tangible way you can deal with uncertainty. That is to be creating resilience before you need it. As you described it, it’s a safety net. Some things are just language, and I’m using a different language, but the principle is very similar.

That’s the time when you work on your resilience. It’s not after the crisis has occurred. There are so many people who got really taken out by the pandemic because it came completely unexpected, and they didn’t know what to do. Similar to the global financial crisis. In September 2008, the world, as we know it, changed, and there was tremendous fear and great uncertainty.

Some people froze and panicked. Others had been planning for that eventuality. I know it sounds strange because it’s not that anybody has to be a soothsayer and have a crystal ball. Certainly, in business or any aspect of life, the way that I think I have a crystal ball is to assume that the shit is going to hit the fan. There is going to be chaos.

In fact, chaos is the norm. It’s the exception to that rule, “When everything is calm and peaceful, and whatnot.” Even in those times, I can’t be sure we’re maximizing our potential for growth because our greatest growth often comes when we’re the most unsure and uncertain. Like what you just described.

For that reason, professor, I would say that resilience is one of those things that’s baked into every success story. When you look at your own success, in many ways, it’s your capacity to have been resilient time and time again. That is to actually develop strength out of adversity. An adversity gain, if you will, or an uncertainty gain.

Others might be struggling simply to get back to normal. There’s no normal. There’s no going back to normal. Today is normal. Tomorrow will be a new normal and the next normal after that. It’s about how we continue to leverage everything that’s going on for some advantage or for some net gain. That’s how we leverage the future. That’s how it seems as no matter what happens, we always land on our feet. Some organizations are constantly finding opportunities and so opportunistic because they’re prepared ahead of time to do those pivots.

If you think about how the world works, when there is a change, the change may be net negative for some but will be net positive for others. Consider, for example, the travel space. Going back to when you and I were growing up, times like the 1980s, there were travel agencies. If you wanted to book a trip and not just, “I have to go fly to San Francisco,” but “I want to do a vacation,” you would call a travel agency.

When there is a change, the change may be a net negative for some but will be a net positive for others. Share on X

People who were not in the travel field, who want to get into it, said, “I have to build a travel agency, so I have to go get connections to all the different booking systems. I have to go market and convince people to call my travel agency. Even though we look like everyone else, fairly, we’re better.” That’s hard. That’s a lot of work.

In the ’90s, as the web grew up, all of a sudden, people said, “There’s a new way to do this. We can move everything online. You don’t need people. We’ll let the end consumer, the people booking a vacation, directly manage their vacation planning.” If you were running a travel agency at the time, you were in trouble.

Nowadays, travel agents are far less common. Travel agencies are much smaller, but there are a bunch of people who are not in the travel industry who said, “I can go in and capitalize on this opportunity.” Disruption could come from a technological change, sociological change, economic change, or legal change. There are all things that cause a change.

Every time there is a change, it can be painful typically for certain incumbents in some cases. You might be one of those incumbents. It can be an opportunity for other people. If you see yourself as one of those other people, you can not only get back to where you were, in the definition of resilience we used, but go further, as you’ve suggested. Get ahead. Change is opportunity.

Not bounce back, but bounce forward. As you said, without naming all the places, but to even naming a few, we don’t have to look much further than the EV space. The matter is you could be invested with your money, your job, or other things. In terms of combustion engines, gasoline, petroleum, oil, etc., all that’s good.

Just know that the disruption of the EV, of changes to battery power, solar, and other renewable energy sources, are not bad things. They may be disruptive things to you personally, but there are opportunities in all of those situations that are profound. The only question is whether or not there will be a moment when you are moving toward opportunity, or you’re resisting that change and holding on to what it is that you’ve invested in thus far.

In the book, Change Proof, what we use at the beginning is a rip current as the analogy that runs throughout the book as being an example of just that thing. When we’re caught in that rip current of change, many people’s first instinct that they have is to resist it. Meaning to swim against the current. I was a lifeguard for many years, so I come from personal experience in that area. That’s why we use that as the running analogy.

Ultimately, when you do that and try to resist that current, which you cannot successfully do, you will become depleted. You’ll become exhausted. That’s when you are more likely to drown. That’s where lifeguards recognize. That’s why we get in the water at that moment because we know what’s coming.

In life and in other areas of life, in business, there’s not always a lifeguard around to help pull you out when you’re wasting your energy, fighting something you cannot actually change as opposed to doing the things you said earlier, which is you can simply pivot and swim parallel to the shore, and then you swim perpendicular to the current of change. It’s an agile approach to it.

You can literally lie on your back and relax. Look at the clouds and the sun because that rip current will spit you out at a certain point, which is what it always does. Yes, you will have a little bit further to swim to get back to shore. You will not have any current that’s interfering with you, and you will save your energy, so you’ll be ready to do it. I got to tell you. I’ve enjoyed our conversation, Mark. Your book is called The Career Toolkit. Is that correct?

That’s right. The Career Toolkit: Essential Skills for Success That No One Taught You.

PR Mark Herschberg | The Career Toolkit

The Career Toolkit by PR Mark Herschberg

I know there’s a lot of very important resources that you get access to through the book. It will be a small investment to purchase the book, but a lot of free resources come along with it. Mark is doing this from a very much heart-centered place, a place as an educator, as somebody who wants to see people succeed. He’s very busy with the startups that he’s involved in, as well as teaching, as well as that we are in the entrepreneurial space. We know what that’s all. Thank you for the work that you’re doing on behalf of others that want to succeed as well, Mark. Thank you so much for everything you brought to us. Here’s my very last question for you. Is there one thing you do on a ritual basis to help yourself recharge each day?

Nothing on a daily basis that’s structured. I just make sure there’s some downtime. There’s some time when between meetings, I relax. I let my mind go, watch TV, or do something where it’s not constantly on. You get that little bit of recharge.

You take the cognitive load, which we’re all having some increasing cognitive load for a variety of reasons that we speak about with some brain scientists that we’ve had on the show. We won’t revisit that now. It’s to let that cognitive unload, whether it’s for 5 or 10 minutes, even 5 minutes. The research is very clear.

Five-minute breaks between your meetings will cool your brain down. It’s amazing when they map this out. You get to see the different colors that represent the changes in the dendrites and neuro pathways in our brains. When we have 5 to 10 minutes of break in between things, our brains cool down, and it’s blue.

When we don’t have those breaks and those meetings are one after another, our brains are orange and red. We’re literally hot-headed. We cannot think as well. Cognitively, we’re in decline and depleted, and ultimately, it depletes our resilience. What you said, Mark, is magnificent. We all should be thinking about how we place those breaks, intentionally speaking.

Put those breaks into your day so that you know that you don’t have to get to the level of mental exhaustion that so many of us feel at the end of a typical day. If this conversation was meaningful, we want to hear about it. You can leave a comment or feedback of any kind at

If this is an episode that you think some other folks in your world, other leaders, other people who might benefit from hearing some of these things, please feel free to share this episode. We love it when you do that. We love it when you tell us you’ve shared it with your community. Apple Podcasts, or wherever you’re consuming this particular episode, please leave a review. They’re very helpful to us. It’s about the algorithm in some respects. When you leave a five-star review and leave out one of those kinds of things, what ends up happening is that this content gets shared more frequently with other folks. We very much appreciate your help in getting the message out. With that, I will say, have a beautiful day.

Whatever you’re doing, there are too many blessings to wish you, but I will wish you that you feel grateful at this moment for your life and for how things are going. Whatever work you’re doing to make things even better. Think about the things that Mark shared with us. Communicate effectively with people. Keep ethics at the front of your mind.

Be grateful for all of the things that are happening, whether they’re positive or maybe they’re not positive. Everything is net positive. If we’re preparing for any eventuality and making ourselves resilient to whatever change proof, then everything will be net positive. With that, I’ll say goodbye. Again, Mark, thank you so much for your time.

Thanks for having me on the show.

Mark and I certainly got into it. There are lots of interesting twists and turns in this conversation. I loved it. I loved the fact that he was so prepared to unpack those ten essential career skills and the fact that we were able to even supplement it. I thought he was very flexible in his approach, and we talked a lot about those particular skills.

We dove into specifically one of the skills and tools that are often underrated, undervalued, underused, and underutilized. That is with respect to ethics. I love how that came about, as well as talking in depth about resilience and what that looks like in the tech world, in the startup world, in the world of innovation, where Mark spent so much of his time.

We talked about comedy and improv, which was a very interesting way to start our conversation. I loved it. We dove into some aspects of culture and culture theory that are very important as well. From a business perspective, a leadership’s perspective, and an entrepreneurial perspective, this was a vital conversation.

It’s one that people will be enjoying and gaining a dividend for years to come. That’s a prediction because these are the kind of things that are not often taught in business schools but probably should be. Mark is certainly changing that at MIT, and I loved where we’re able to take our discussion.

I hope you enjoy the episode. If you love it, share it with a friend. Share it with somebody that you feel could use this kind of insight. As always, we appreciate your comments. You can go to and leave a comment. If you’ve not established your own resilience level and want to find out what your current baseline is for mental, emotional, physical, and spiritual resilience, it’s as simple as going to and getting your own score in less than three minutes. That’s the best part.

Get your score and get the resources and tools after that. Many of which are simply going to come to you in email form for free. It’s a no-brainer to do it. Figure out where you’re starting from so you can learn a little bit more about what it means to close the gap. Regain some of your motivation, inspiration, mojo, and productivity, and take care of yourself even better on the road ahead.


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About Masrk Herschberg

PR Mark Herschberg | The Career ToolkitMark is the author of The Career Toolkit, Essential Skills for Success That No One Taught You. Educated at MIT, Mark has spent his career launching and fixing new ventures at startups, Fortune 500s, and academia. He’s developed new software languages, online marketplaces, new authentication systems, and tracked criminals and terrorists on the dark web. Mark helped create MIT’s “Career Success Accelerator”, where he’s taught for twenty years.