Episode 87: How to plan your career change – with Mark Herschberg of The Career Toolkit

Author of “The Career Toolkit” Mark Herschberg explains how you build the road map to enable you to start planning your career change.

Today’s guest

Mark Herschberg of The Career Toolkit

Website: The Career Toolkit Book

LinkedIn: Mark Herschberg

Facebook: The Career Toolkit

Twitter: @CareerToolkitBk

Instagram: @thecareertoolkit

From tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems, Mark Herschberg 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 and computer science, and a M.Eng. in electrical engineering and 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.

What you’ll learn in this episode

  • [02:03] Mark explains the origins of his book and who the target audience is.
  • [06:42] Looking at your long term career options rather than just the next job.
  • [08:00] Finding out unwritten skills required for jobs by networking with people in the industry.
  • [08:59] Using intermediate roles to make the transition into the career you want.
  • [10:08] How to identify the qualifications and skills you need for specific roles.
  • [10:38] Figuring out whether you need to go back to school.
  • [11:41] Taking alternate paths to get to your career destination.
  • [13:30] Mapping out your career path by looking at gaps in your knowledge or skill set.
  • [15:02] Approaching connections to help you identify potential intermediate roles.
  • [16:23] Qualifications which can give you a broad scope of opportunity.
  • [18:58] Understanding where a career path will take you and how to orient yourself to it.
  • [20:32] Identifying sub-professions that would suit you more.
  • [21:46] Ensuring you have multiple paths to divert and change course to.
  • [23:10] Having a broader view of adjacent industries to see what may impact you.
  • [24:18] Recognising trends within your role or industry to determine potential future job risks.
  • [27:03] The importance of looking at your projected income as well as short term.
  • [28:36] How not to get sidetracked and ensure that you’re aligned to your goals.
  • [30:50] Recognising what motivates you so you can effectively measure your progress.
  • [31:46] Figuring out the need for an accountability coach or partner.
  • [32:57] Using your network to get in contact with people that can help.

Resources mentioned in this episode

Please note that some of these are affiliate links and we may get a small commission in the event that you make a purchase.  This helps us to cover our expenses and is at no additional cost to you.

To see the resources recommended by all our guests, visit the Resources page.

Episode 87: How to plan your career change - with Mark Herschberg of The Career Toolkit

Jeremy Cline 0:00
You've figured out what you want to be, you've done the coaching, you've done the introspection, you've got a really good idea what you want to do with your career. Thing is, you're doing something completely different at the moment. So, how do you get from one to the other? How do you get from A to B? That's what we talk about in this episode. I'm Jeremy Cline. And this is Change Work Life.

Jeremy Cline 0:34
Hello, and welcome to the Change Work Life podcast, the show that's all about beating the Sunday evening blues and enjoying Mondays again. Now, we've spoken a lot on the podcast about how you find your path, how you identify the career that's right for you. But once you've done that, how do you actually go about getting there? How do you figure out the plan? How do you figure out the steps you need to take? To answer all these questions, I'm delighted to be joined by Mark Herschberg. Mark is an instructor at MIT, he's a consultant Chief Technology Officer at various different companies, he's a ballroom dancer, and he's the author of the Career Toolkit: Essential Skills For Success That No One Taught You. Mike, welcome to the show.

Mark Herschberg 1:14
Thank you for having me. It's a pleasure to be here today.

Jeremy Cline 1:16
Mark, against that backdrop, if someone at a drinks party asks you what you do, what do you tell them?

Mark Herschberg 1:22
Well, it's always context specific, but typically, I say right now a fractional CTO, so I build and fix start-up companies. And currently, because I am off promoting my book, I'm doing it fractional. So, that gives me time to help each company a little bit and a little time for myself to go on this virtual book tour.

Jeremy Cline 1:41
When you say fractional, I mean, how thinly do you spread yourself?

Mark Herschberg 1:44
It has varied. Sometimes it's as little as a couple hours a week. Typically, it's on the order of about two days a week per client, and some are just project-based, and some are longer term.

Jeremy Cline 1:56
And how did you come to write the book? What was your journey that took you up to putting pen to paper or fingers to keyboard?

Mark Herschberg 2:03
The book was quite unplanned on multiple levels. It began about 21 years ago, when I first started hiring. And when I would interview candidates, I'd ask them a technical question, that might be a technology question for software engineers, or a marketing question for marketers. So, 'technical' we're using broadly. They'd give me that technical answer, they understood their discipline. But then I would ask a question like, 'What makes someone a good teammate? What are the qualities you look for in a leader?', and I would get blank stares, because we've never trained people to think about these issues. And I realised I needed to think about them to get where I wanted to go. So I had actively sought out the answers. And as I was going on this journey, developing myself and discovering other people were not really focused on these questions, MIT was pulling together a similar programme. And so, I reached out and said, 'I've been working on this within my company, I've been working on training programmes, can I help you out?' They said, 'Yes, please, come help us develop a programme.' And then they asked me to come teach the programme, which I've been doing now for the past 20 years. And from having done this at MIT and elsewhere for over two decades, I realised this is a broad challenge, and I wanted to take the content we had and put out there, not just for MIT students, because it's not just their challenge. This is something we all face. And so, I turned it into a book.

Jeremy Cline 3:17
And when you were writing the book, who did you have in mind? Who is your sort of ideal reader?

Mark Herschberg 3:21
It's hard to narrow that down. I say I'm targeting people 20 to 40. So, I'm catching people right out of college through the earlier part of their career, but I have met time and again people in their 40s, 50s, even in their 60s, who have said, 'I don't know how to network, I don't know how to negotiate. Oh, I really need to learn this stuff, I wish I had learned it 20 years ago.' So, it really is universal across experience levels and across different disciplines.

Jeremy Cline 3:51
And it covers a fairly broad range of topics. I mean, you've mentioned networking and lots of other things. I mean, the contents is quite a sight to behold. I mean, were you conscious that you could end up writing pretty much on every single topic on every single chapter? And how do you condense all that into something manageable, into one volume?

Mark Herschberg 4:11
That is indeed a challenge. The reason I decided to go in this direction and choose a broad book instead of deep is for two reasons. First, the list of topics, this isn't just, well, Mark thinks this is important. This comes from feedback that MIT and other universities have gotten from corporations, saying, 'These are the skills we're looking for, but we're unable to find.' And so, I wanted to make sure I addressed all those, to make someone well-rounded and really effective and attractive to different jobs in corporate America, as well as if they want to start their own type of company. But then, the other reason is because these skills really build upon each other. A good leader knows how to negotiate. A good negotiator knows how to communicate. The skills all help reinforce each other, and that's something that you don't get in one of these narrow books. So, when I tackle each topic, in each chapter you get what is the kind of mental shift, what is the change in how you perceive it to recognise opportunities and recognise places where you can apply this, outside most people's more narrow, traditional definitions, and then what are actual tips, but then I end each chapter with, here are next steps to go further, including I reference probably about two dozen books within mine, for people to go further and explore more.

Jeremy Cline 5:26
I really like this idea of kind of reinforcing things and not treating everything in isolation. I think that's a very, very powerful idea and that just makes perfect sense. You mentioned next steps, which segues rather nicely into the topic I wanted to discuss with you. So, probably good idea if I come up with a case study here. See, you've got someone who's, I don't know, they're in their late 30s, say, they have been a lawyer for the past 15 years. They know they don't want to carry on being a lawyer. And they've already been through the introspection, the coaching, they've worked out what their values are, they've worked out what they're good at, what they're not good at, their transferable skills, and they have identified that they would like to be, let's try and pick something which sounds reasonable and which will help with our conversation, but I don't know, they've decided to be a web developer, say, for example. I'm guessing if they've decided to be a web developer, they've probably been messing around a little bit with that, but maybe not in any kind of serious way. Or maybe they haven't, they've just kind of identified that they've really got that sort of brain and now they've learned about it, they've discovered that that would be a really good thing to do. They've got no meaningful experience in it. Having had the realisation, having thought, 'Yep, this is what I want to do', how do they make it a reality? What's the first step they should take?

Mark Herschberg 6:42
When looking at your career plan, a lot of people focus just on the next job. And one of the things that I teach is you want to take that long-term view, you want to look out ahead 5, 10, even 20 years, if possible. And given that goal, you want to work backwards. So, start with that goal. Start with, I want to be a web developer, and then say, 'What are the skills I need to be a successful web developer?' Now, some are obvious, some we can get right from the job description. Well, you need to know how to write software in certain technologies. But then, there are other skills that might be unwritten that can go along with that. So, for example, law is traditionally a very solo practice. Even when you're in a big law firm, a lot of lawyers, they work independently and just kind of report in, whereas software engineering, contrary to popular belief, it's actually very much a team-based activity. It's very collaborative. So, team skills are actually pretty important. If you're not used to that team collaboration, that might be another skill that's not explicitly listed in a job description, but from talking to engineers, you'll discover, okay, teamwork is important.

Jeremy Cline 7:48
So, just on that point, how do you, I mean, this person might not have realised that team skills is an important part of it, how do you know what you don't know? How do you find out these sorts of things, what other skills are necessary?

Mark Herschberg 8:01
You begin by speaking to people in the field, because reading job descriptions tells you one thing, but when you actually talk to practitioners, they're going to tell you what it's really like. They're going to tell you what a typical week is like. The example I usually give is actually law, because we all grew up watching legal programmes on TV, right? Pick whatever generation you are, you have the law show you love watching, and it's always dramatic in the courtroom. But actual law has very little to do with the inside of a courtroom. And if you are thinking about being a lawyer, talk to actual lawyers and say, 'What do you really do?' And they'll tell you, 'I go into a courtroom maybe twice a year.' And so, you realise, 'Okay, it's not going to be that exciting drama, oh, it's really sitting in my office doing lots of research, okay, that's helpful to understand.' So, speak to people in the industry. That's where you get the most information. Ask them, 'Tell me what your job is like. In a typical week, where are you spending your time? What are your challenges?' That's going to illuminate it much better. And so, then once we have that understanding, you begin to map out how you start to address that shortcoming. Now, that could be by taking classes, could be reading books, listening to podcasts, getting training, getting coaching, it could also be looking for intermediary jobs. So, for example, lawyer to web developer, one possible intermediary option is going from lawyer to a product manager within a legal tech company. Because in this first step, you don't need to be as strong as a technical person. You don't need to know how to write code yet. The fact that it's a legal tech company, your legal background can help you be a product manager, you understand the customer very well because you've been one, but now you're getting closer to the engineers. So, you might want to map out an intermediate step. Depending on how far you are, you may or may not need that intermediate step. And then, of course, in some cases, you can just literally go back to school and come out with a degree or certificate that reorients you to the new career.

Jeremy Cline 9:58
When it comes to the qualifications, how do you identify what you're going to need? And especially, for some people, the idea of going back to school and the costs that may be involved, that's going to put a lot of people off.

Mark Herschberg 10:09
In terms of identifying what you need, this comes from reading those job descriptions and talking to people and hearing about what are the skills, asking literal questions such as, 'What are the skills you'd recommend for someone going into this role? What do you look for in a candidate? What do you wish you knew when you first started this career that maybe no one told you?' So, there's a series of questions you can ask to explore and uncover this and generate that list. And of course, talking to different people, you'll start to get different perspectives and can triangulate down on it. To your question about going back to school, that is certainly an important calculation, spending $100,000 plus to go get an MBA or get a law degree or a master's degree in certain cases, that's an investment we can afford to take when we're 26 and we have a full career that's going to pay off that debt. And we know that this investment will increase our overall opportunity. If you're 42, and you're already at a decent level of earnings, losing that income, investing in that change, may not be as cost effective. And this is an important calculation that you need to do.

Jeremy Cline 11:16
What about identifying alternative means of getting to the same result? I mean, is there sometimes only one path, or are there alternatives? So, you know, maybe the 26-year-old would go and do the master's at university, but the 42-year-old, who has the level of salary, and who probably also has the responsibilities, the children, the mortgage, that sort of thing, how do they explore what alternatives there might be?

Mark Herschberg 11:42
This is an important question, because there is almost never a single path. There are typically multiple paths to get to the same place. And equally importantly, when you create this plan, it is not set in stone. Don't think, 'Okay, I have this three-year plan to get from where I am today to that dream job, and I have to follow it. And when I get bumps along the way, oh, this is just a setback.' You can take alternate routes, right? What happens when we hit some traffic as we're driving somewhere? We look for a different path to get there. And the same thing is true in our career plan. So, you might discover there are a few different paths and you begin down a path. And as you go down it, you're going to learn more, you're going to have a better understanding, six months, a year in, you're going to potentially revise that plan, or other opportunities might come along that you didn't even know about ahead of time. Or you might discover some of the next potential steps on the path are no longer quite as appealing now that you're a little further in it. So, I encourage people, as they execute on their plan, every six or twelve months, you want to sit down and revise that plan. You want to look back and say, 'Along this path, what skills have I now added to my skill set? What have I achieved? How much closer am I? And does this change the opportunities before me? Do I need to alter the path because I now see a better one?'

Jeremy Cline 12:59
The answer to this question, I'm certain, is, 'It depends.' But if you're just starting out down this path, and maybe you're in a career which you're desperate to get out of, how long realistically should you kind of set yourself up for in your mind for, 'Well, I'm probably still going to be doing this job for dot dot dot period of time before I start making what looks like, you know, more meaningful changes to where I'm actually working'?

Mark Herschberg 13:26
You're right, it depends. But let's talk about what it depends on, because that's the important answer here. It depends on the gap between where you are today, and the skill set and experience that you need to be where you want to be tomorrow. When you look at that gap, that gap might just be, 'Oh, I'm just short of experience, I just need to gain a project experience. I just need to have some experience maybe managing some people for six months, I'm gonna ask my boss, can I help lead this project.' It might be knowledge of a particular area or technology. But it might be a number of different things, it might be knowledge of a discipline, might be knowledge of tools, might be experience doing certain types of projects. And when you get that larger map, you're going to say, 'I can't tackle it all tomorrow. I can't suddenly learn all this in just two weeks. So, I'm going to lay out a plan, how do I spend the first three months learning this skill, the next six months gaining that experience', and map out that plan, that again, will be altered as you go, that you want to reflect upon partway and readjust as you go down the path.

Jeremy Cline 14:30
I wanted to come back to this idea you talked about, sort of intermediate careers, so the things which are kind of the halfway points between where you want to get to. Now, you came up with a brilliant example, which I would never have thought of, lawyer to web developer, so becoming a product developer in a legal services company. How do you go about identifying what these intermediate jobs might be, particularly if you're first contemplating this change, and you just can't see these things which might act as these points as you're on your way?

Mark Herschberg 15:03
I think of it a lot like in a bowling alley, you want to knock down adjacent pins as you're trying to get to that final pin, right? But you have to understand what that set-up of pins looks like, which is, of course, your question. And this comes from exploring the area. When you're looking to enter a profession, whether it's your current profession and you just want to grow in your current profession, especially if you're recently out of school, if you're inexperienced, or if you're looking to get to a new profession, you want to speak to people in that industry. And when you ask about the job that they do, ask about other jobs. Ask, 'Who do you tend to work with? Oh, you're in engineering? Who do you work with? Oh, I hear you work a lot with product people.' You're gonna hear that from all the engineers. They don't work as much with salespeople or finance people. But they work a lot with product, sometimes with marketing. And so, you're going to hear about these adjacent jobs, about who they work with. You can explore and ask people in those adjacent jobs, 'Hey, I've been hearing a lot about product management. I'm curious to learn a little about that.' And then, you can start to map out what that set of bowling pins looks like. And you can create that map that's going to show you some potential paths to go from where you are to where you want to wind up.

Jeremy Cline 16:12
What happens if those potential paths really don't appeal to you? You've got your heart set on being a web developer and spending however long in some kind of client facing product development role, or whatever it might be, just really doesn't appeal.

Mark Herschberg 16:25
This is where school often acts as a reset button. No matter what you may have studied in school, you could be a teacher, a consultant, a salesperson. If you go to law school, you come out as a lawyer. Pretty much everyone out of law school, you're qualified as a lawyer. MBAs tend to be this much more diverse reset button. With an MBA, it doesn't matter what you were going in, you can come out and you can be a consultant, you can be a marketer, you can be a strategist, MBAs have really a diverse exit strategy, as opposed to law, in which you come out and you're focused on law. So, you can go back to school, you can go take some web development courses. And when I say school, this might be a formal University Graduate Programme, this might be some online certification school, but certainly look at the qualifications, look at their placement rate. And when you come out, after you've invested a certain amount of time, you are now qualified for that job. And I want to be hesitant here because in web development, there are so many schools lately, this is my area, so many schools that will train you to be a coder, and really, it's a three-month, six-month programme where they're training you at such a low basic level. I know for myself and a lot of other CTOs, we don't think most people right out of those programmes are qualified. So, if you do invest the time and resources, look at the placement rate, look at where people wind up, look at starting salaries, to make sure that is acceptable to you. And then also, obviously, look further down the road as you go on this new career path, what will salaries be like not just out of school, but 5, 10, 20 years down the road?

Jeremy Cline 17:58
Presumably you can also use your conversations with people in the industry about what qualifications are looked upon favourably, not favourably, will give you a good start, will require a bit more work, that sort of thing.

Mark Herschberg 18:11
Absolutely. Asking people is really the best way to gain information, because for all the blogs and podcasts and everything else, it's going to start to give you a direction to go in, but really, it's those conversations that are going to give you a much richer picture to understand what the job and what the industry is really like.

Jeremy Cline 18:29
To those people who are concerned that – they're fairly sure that they're going down the right path, but there's always going to be that lingering doubt that things might change, the industry might change, or however much research you've done, once you're actually there, it might not necessarily be all it's cracked up to be. So, how do you kind of stay motivated to go down this track, which could be quite hard work, against the backdrop of, 'Well, is it really still going to be the right thing for me?'

Mark Herschberg 18:59
This is why you want to ask people about their industry and their jobs, not just a job you're looking at today. So, a great example is consulting. I know a lot of people who right out of school said, 'Consulting, it sounds so sexy. You fly off to some city each week, you're staying in a nice hotel, you can expense all the dinners, isn't this great?' And it's exciting, you're working with other young people, and you can be a road warrior. And you're racking up all these frequent flyer miles. I have friends who love that. But then, when you're in your 40s and you have a family at home, the idea of spending four or five days on the road, now it's exhausting. Now it's, 'I just want to be home with my kids.' And so, it's important to understand, if I go down this path, where will this path take me in 10 or 20 years? What will that job be like? Not every consultant has to be on the road four or five days a week, but you want to make sure if you're going down this path, how do you orient yourself to one that doesn't travel as much, if that's not what you want to be doing in your 40s. So, you do need to be, it's like driving, you want to be looking ahead. Likewise, as you speak with people, ask them about what's happening in the industry, what are the changes, what are the trends, what do they think the industry will be like 5, 10 years down the road, because they have more experience than you do. And this is going to help set you up to recognise where are the opportunities and to avoid areas that might lead to a dead end.

Jeremy Cline 20:20
Is there always going to be an opportunity, rather than a dead end, even if you've decided that, 'Actually, I've decided that web development really isn't my thing', after having invested three years in the process of trying to get there?

Mark Herschberg 20:34
This is another 'it depends'. So, we'll take web development, and particularly, if you're thinking of web development as in, 'I am going to build websites', if you were to speak to someone like myself in the industry, I'm going to tell you, 'You're competing against web developers around the world.' If you're in a country like the US or UK with relatively high wages, understand there are developers who are working for $20, $15 or $10 an hour, who are going to be undercutting you in terms of pricing. Now, there's more advanced type of work, working for large corporations, building more sophisticated sites. But if you just want to build a site for the local construction company, a site for the dentist, you're going to be competing against other low-cost labour, and that's going to be a very difficult job to maintain over the long term. So, there might be, within a profession, certain aspects, certain almost sub-professions, certain areas where you might specialise in that might be better or worse.

Jeremy Cline 21:30
And what about if you've started to enter the new profession, you've gone a fair down that way and you've realised that, despite the exercises, despite the introspection at the start, you have unfortunately concluded that maybe it wasn't for you, where do you go from there?

Mark Herschberg 21:48
At that point, if you've created a rich enough plan, you know that's not just this one path, and you have these alternative paths. Now, the alternative path, we talked about how there are multiple paths leading to the goal, but likewise, any path doesn't only lead to one goal. Each path can take you potentially in multiple directions. And if you've done a good job exploring this, of talking to people, of mapping out different opportunities, you can divert, right? If I am heading, let's say to San Francisco, I'm driving from New York to San Francisco, and I quickly realise San Francisco is not really where I want to be, along the way, where my friend calls, I say, 'Oh, my god, this doesn't sound interesting anymore. Well, maybe I can divert a little and I can head to Las Vegas', right? It's in the same relative direction, I just make a small turn, a small course correction, and now I'm on a new path. And so, you want to make sure you have a clear map that's not just your one path, but multiple paths and where they can go.

Jeremy Cline 22:45
And I think that's a really important point, isn't it? That it's worth taking away that, even if you are apparently single-mindedly focused on a particular goal, it's worth just keeping things in the corner of your eye that might be a bit interesting, and you might suddenly think, 'Oh, okay, maybe that option is worth exploring a bit more', rather than just focusing on very much on the one path that you're doing.

Mark Herschberg 23:12
It's important to do this for a few reasons. One, as you note, it gives you some alternative options. The other, of course, is, what is most likely to impact your role? It's these adjacent roles, it's the people you work with, as they change their responsibilities, as they change their tools, their capabilities, it's going to impact where the lines are between you and them, and ultimately impact your job. So, you want to pay attention, not just with blinders on only to your profession, only to your industry, only to your role, but you want to look at adjacent ones, because they're the ones most likely to impact you.

Jeremy Cline 23:48
This is something that I've not really come across before, this idea, not of just looking at people who do the job that you want to do, but people who do the jobs around what you want to do, as you describe, in the adjacent roles. I'm sure most people haven't heard of this, but you've described two contexts where it could be really important. One, in the context of these adjacent roles might be a means by which you get to the end goal, but also as a means of understanding what the role might look like and how it might change in the future.

Mark Herschberg 24:20
Absolutely. And this is where, if you're not paying attention to it, you can wind up basically being side-lined, right? All of our industries are constantly changing, constantly evolving. We see obvious cases where we're told, 'Oh, if you're driving a taxi, beware, because you're about to be displaced by driverless cars.' Those are the big changes, but we see for most of us a lot more subtle change. Let's take lawyers, for example. If you're a lawyer, and this is going to be a technology change, not a different role change, but typically role changes are driven by technological changes. If you're a lawyer, you would spend a lot of time reviewing contracts, right? Looking, researching prior case law. As technology gets better within legal tech, we get better checks. It's like spellcheck, but instead of just checking for the spelling mistakes, it's looking for, 'Hey, here's an issue. This is a common issue people make in this contract.' For example, 'This is multi-jurisdictional, this is two countries. You said dollars, do you want to be more explicit, US dollars versus Canadian dollars?' It's going to flag these things for you. That's going to make it easier for you to find and correct mistakes. Likewise, when researching case law, we all know search has gotten much better over the past 20 years. So, whereas you may have had to look through 50 cases, now you might be looking through eight. This is saving you time. What does that mean? Well, that means you need to hire fewer associates to do this type of work. It also means you have more time to focus on other types of skills, say client relationships or trial strategy. Recognising this trend, that more of the grunt work is going to be automated, means you should be focusing on these other skills if you want to stay relevant. Otherwise, you could be the best person at looking up case law, but sooner or later, that software is going to be better than you and your value to your law firm is going to greatly decrease.

Jeremy Cline 26:16
Which isn't to say that anyone can predict the future and work out what is going to happen, but it's just keeping an eye on these sorts of things, keeping an eye on these trends and so, you don't end up being, I don't know, Kodak or someone like that, whose business model just completely evaporates.

Mark Herschberg 26:33
Exactly. Just like companies have to stay on top of what's happening in my industry and pivot and recognise threats and opportunities, we as individuals have to do that within our particular profession.

Jeremy Cline 26:45
Going back to our lawyer who wants to be a web developer, what are the other obstacles that they might have to overcome on this path? And I say this not to put people off this kind of change, but so they're kind of forewarned, so they recognise that something is coming their way and it might be an obstacle, but it can be overcome.

Mark Herschberg 27:05
Well, it is important to recognise what the projected income is going to be like down the road. A lot of people are just focusing on the income of, 'Well, if I switch from this job to that job, how's this going to change my income?' And sure, it might be a step up, but if you're looking 10, 20 years down the road, look at what your income would be like in the future in both of these areas. Software engineers, for example, we have some of the highest starting salaries outside of university, right? Our graduates tend to get the highest first starting salary. But looking long-term, we flatten out fairly quickly. If money is the most important thing to you, then you might want to look at going to finance or law or working in sales, where you can really just blow it out of the water. So, software engineering, if you're just taking that narrow view of over the next two years, five years, it looks great. Long-term, compared to certain other professions, it might not be as appealing. Now, for most people, it's going to be sufficiently appealing, but it's understanding it within that larger context, what the path might look like going down, or as we said before, recognising if you're going to be on the road when you're in your 40s, is that something you really want to be doing?

Jeremy Cline 28:20
Okay, so that's about having an eye on not just the immediate next job, but what it might look like in five- or 10-years' time. Are there any other sort of typical obstacles or roadblocks that someone might come to, which might throw people off, might cause people to doubt that they're doing the right thing, but they can overcome?

Mark Herschberg 28:39
I'd say, beware of getting side-tracked. So, here's a typical example. You come out of university, you go into a consulting firm, and you don't really know what you want to do. You're just excited to be a consultant. And your boss says, 'Okay, I'm going to put you on a CPG project. That's consumer packaged goods. You're going to go help this company'. And you say, 'Okay, yeah, I'm just excited to be here.' So, you work on that project for 18 months, and you realise, 'Well, this isn't super exciting.' But your boss says, 'Hey, listen, I've got this other project, we really need you on this.' And you say, 'Okay, I want to be a good team player.' So, you spend another two years on CPG projects. You really want to get out of it, because you've been doing this for three and a half years, and you talk to your boss and your boss says, 'Okay, I understand, but listen, we've got this emergency, just do this one other project and I promise I'm gonna move you after that to the energy group if that's what you really want to do.' Say, okay, fine. So, you do this other project, your boss leaves the company, new boss comes in, you've now been working in CPG for five years. You say, 'Well, I want to go to energy.' And your new boss says, 'You're not an energy guy. You're a CPG guy. You've got this background. You've got this training. The energy team, they're not going to take you, they're going to take people who have energy backgrounds.' And you've now been pushed into an area, into a sub-specialty, and I'm giving consulting as an example, but I've seen this within different disciplines, you're now oriented in a certain area that you didn't intentionally plan to be. So, we have to be very conscious about the type of work we do, even within our industry, and make sure it's aligning to where we want to go.

Jeremy Cline 30:14
What are some of the indicators of success? Because the process and path you've described, someone who's at the very start of that could look at that and think, 'You've got to be joking. I've got to wait five years, I've got to wait 10 years, I've got to do all these jobs which don't seem to necessarily bear that much relation to what I want to do. Okay, they're a bit closer, but maybe they're not. I've got my heart set on doing web development', in our example, 'I'm going to have to take classes, I'm going to have to do this, I'm going to have to do that, I'm going to have to do the other.' What wins can people look out for on the way to keep them motivated?

Mark Herschberg 30:52
It really depends on what's motivating you in the long run. The motivation for some people is amount of money that they're making, for other people it's the industry they're working in, or it's a type of company. Some people say, 'I'm just excited to be working at a start-up, or I want to work at big law. Once I'm in big law, I don't care what it is, but my foot's in the door. I'm now in big law, this is exciting.' Recognising what motivates you and what along the way do you feel like, 'Okay, I feel a step closer. I've gotten in the door, I've hit some salary level, I'm learning about this new type of industry or new skill', whatever it is that you define, but you want to make sure if you have that path, what are those steps, what are the things you're trying to achieve, and then you can measure your progress against that.

Jeremy Cline 31:37
How easy is it to do all of this by yourself, rather than with some kind of an accountability partner, be it a coach or, I don't know, a trusted friend or someone else you can discuss these sorts of things with?

Mark Herschberg 31:49
The need for a formal accountability partner is probably going to vary on your personality, whether you're self-directed, or it helps to have someone there making sure you're sticking to it. But in terms of just even planning this out, doing it on your own is very difficult. And this is why throughout you've heard me say talk to other people, talk to people in the industry, talk to people who might be alumni from your university. They're going to be, of course, in all sorts of different jobs, but you have that connection to them. Use your network to reach out to people in the target industry or target roles you're interested in. Potentially, talk to people in HR, especially if you're looking to transition within your own company, but talk to lots of people, because it's only through this exploration that you begin to fill out just how complex this change is, and create those paths that are going to be most effective.

Mark Herschberg 32:39
The idea of going to talk to other people in the industry is one that's come up a few times. But I'd be interested to hear your take on the person who's concerned, 'But I don't know anyone in that industry. And yes, I can look LinkedIn, but why on earth are people going to speak to me?' What's your take on how you approach people where you just don't think you have connections?

Mark Herschberg 33:01
This is a great example of why I wrote a book that is very broad, because while in Chapter One, we speak about creating these career plans, in Chapter Eight, we talk about networking, right? And your network, of course, is going to help you in this situation. It is not simply the people you know who are in your network, it's people known to people you know. So, don't think, 'Well, I don't know anyone.' Start asking your friends, 'I don't know any lawyers, do you know any lawyers? I'd love to sit down and speak with a lawyer who is involved in this type of law.' So, use your network. Your network is not just the people you know, it's your more diverse network, your second- and third-degree connections. And of course, if you're going through that trusted connection, it's easier. If you just cold called a stranger and said, 'Hi, I wanna meet you for coffee', the lawyer is gonna say, 'Well, that's great. I charge $400 an hour, so, happy to meet with you.' But if you're going through your friend, the lawyer will say, 'Sure, happy to get coffee, because our mutual connection's a good friend of mine.' This is also why I recommend looking at a university alumni database, because you have that common affiliation. You have that commonality, you can say, 'Oh, of course, yeah, you know, I remember what it was like when I was first out of school, or I'm just always happy to help an alum.' You could find other affinity groups. You mentioned at the start that I was a ballroom dancer. One great thing about ballroom dancing is ballroom dancers are not all software engineers, unlike, say, the software engineering companies I work for. Ballroom dancing, we have lawyers, we have doctors, we have marketers, so I meet a diverse range of people through my hobbies, and your hobbies or religious groups could lead you to an interesting, diverse set of people. And so, don't feel it's just people I know professionally. It really is broad. And if you start to sit down and explore who people you know might know, you'll find it's a pretty wide set.

Jeremy Cline 34:29
Mark, you've certainly given people an awful lot of food for thought here. If someone wants to follow up on any of the different aspects of this that we've talked about, then, obviously, apart from your own book, where might you suggest they take a look?

Mark Herschberg 35:02
Start by going to my website, the careertoolkitbook.com. Not only can you learn more information about the book, you can follow me on social media or contact me, you can go to the Resources page, where I recommend other resources you can use to go further on some of these topics. And you can also see how to download the free app, which is available in both Android and Apple stores. And it takes a lot of these techniques, and a lot of these tips, and puts it into a free app that sits in your pocket. I know when I read a book like this, I say, 'Wow, this is some great advice', and I forget it three weeks later. Because we all move on to something else. So, this is like a daily affirmation, the app's on your phone, you don't even have to open it. And it's gonna pop up a reminder, it's gonna pop up something like, 'Be sure to reach out to people from your college alumni network.' And you go, 'Oh, right, yeah, I remember, he said that, I'm supposed to do that.' And so, just once a day, it takes three seconds, it pops it up, you look at it, you swipe it away. Or if you're about to go into a networking event, or an interview or some other type of activity, you're not carrying my book with you. But now you've got the app, so you can open it up and quickly refresh on some of the tips. So, now you're ready to go into that event and make the most of it.

Jeremy Cline 36:10
And in terms specifically of the career planning bits, the working out how to get to the next steps, are there any on your recommended resources list that particularly leap out and point to that as a topic that people might want to explore?

Mark Herschberg 36:24
I'll mention first, there is, one of the downloads on the website includes a bunch of questions you should start asking about. But then, I recommend a number of other books. I would say for anyone who's thinking of a PhD, there is a wonderful book called A PhD Is Not Enough. And everyone thinking of a PhD, no matter what field you're in, you must read this book. And even if you are not a PhD, this is useful because it does illustrate how to think about leveraging what your domain expertise is, and how to use that to go further. But absolutely anyone doing graduate work, start with this book, it's a must read.

Jeremy Cline 37:02
Fantastic. Well, I'll definitely put a link to that. And I think you may have already mentioned it, but just as a reminder, where's the best place to find you and get hold of all your resources?

Mark Herschberg 37:11
The careertoolkitbook.com. And from there, you can see all my social media and other ways to follow me and contact me.

Jeremy Cline 37:18
Brilliant stuff. I will put links to those in the show notes as well. Mark, you've given us an awful lot of food for thought. Hopefully, some people have been inspired by this, not feeling despondent at the amount of work they might have to put into this. But hopefully they are inspired. Thank you so much for your time.

Mark Herschberg 37:33
Thank you for having me. I've enjoyed being here.

Jeremy Cline 37:36
Okay, what do you think of that interview with Mark Herschberg? Hope you enjoyed it. Mark talks a lot about connecting with people in the field that you're looking to move into, which is a theme that we've touched on in previous episodes. But the point about getting in touch with people who are in adjacent roles was something that I had not come across before. And I thought that was really interesting, especially in the context of trying to transition out. So, potentially using some of these adjacent roles is a stepping stone for where you want to get to. And as Mark said, it's also a really valuable way of getting to know who you might be working with, what are they like, what do those roles involve, what is, ultimately, working with them going to be like. It's also really worth taking away the point Mark made that there is never going to be just one single path. And using the example that Mark gave of setting out to drive to San Francisco, then getting diverted to Las Vegas, that's kind of okay, and having an eye out on the opportunities, seeing that things might not necessarily take you where you thought they were going to, but being open to these diversions, that's all good stuff. And I guess it really means trying to focus a bit more on the journey and not just the destination. Basically, let's enjoy the ride a little bit.

Jeremy Cline 38:47
There's a summary of what we talked about and a full transcript if you want to check out any of the points in more detail, along with a link to Mark's website and where you can get hold of a copy of his book, and they're all at changeworklife.com/87. That's changeworklife.com/87 for Episode 87. And if you haven't figured out where you want to get to, if you know you want to change career, but you just don't really know where to start yet, then do take a look at the exercises on my website which you'll find at changeworklife.com/happy, changeworklife.com/happy. There's a couple of exercises there which are designed as a starting point to start to ask yourself the sorts of questions that might help you, as you work out what it is that you want to do. So, do check out those exercises. As always, there's another great interview coming your way next week. So, subscribe if you haven't already done so and I can't wait to see you in the next episode. Cheers. Bye.

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