"I Feel Behind in My Career. Help!"

0:00Have you ever watched a former colleague's career, or I guess anybody's career, and wished you made the decisions that they did? for the past 20 years, someone has done that with me. And I had no idea until just a few weeks ago, which is when I got this email from a guy I worked with at my very first job. He had been watching what I've done, and he's been regretting what he's done. And he wanted to know if I had any advice. And I did. Because I happen to host another podcast. You're listening here to Problem Solvers, which I host every week. But I also have a show called Help Wanted, where me and my friend Nicole Lappin, who is a best-selling money expert, we bring people on the show, people who have some kind of work problem, who have reached out to us by DM or email or whatever, and we talk them through it.

0:56And we try to come up with some kind of solution. And that's not all we do on the show. We have other episodes where we share our own experiences. Recently, I talked Nicole through her anxiety about sales because we've been doing a lot of sales recently for the show. There's a lot there, but the core of it, the heart of it is definitely just helping people and talking them through their problems that I think a lot of other people face too. So on this episode of Problem Solvers, what I want to do for you is play the episode of Help Wanted, where we talked to my former colleague from 20 years ago who felt just so lost.

1:36But as we would discover, he actually had a lot more that he could do that he wasn't even realizing. But it was right there. So that's what we're going to play for you on this episode of Problem Solvers. It is Help Wanted. You can find Help Wanted wherever you get podcasts, wherever you're listening to this one, just search for Help Wanted. But here is this episode.

2:06This is Help Wanted, the show that tackles all the big work questions you cannot ask anyone else. I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine. And I'm New York Times bestselling author and money expert, Nicole Lapid. The helpline is open. Nicole, do you stalk any of your former colleagues? Like, stalk, stalk? Not in a illegal way, but, you know, you pay attention to them on social. They don't know that you know what they've been up to for the last 20 years. Yeah, I mean, not like in a weird way. I also try to limit social media time. And I do generally think comparison is the thief of joy.

2:46But yeah, for sure. Especially when you feel like you're in shitty places, then I go like check on my ex-boyfriends and they're like wives. We've all gone in the rabbit holes of people from yesteryear. Yeah. And I think that what you just said there, the comparison is the thief of joy is perfect because that's exactly what can happen is that here you are, you were at the same moment in time as someone else and then paths diverged. And it's so easy to look at what they did and maybe think, oh, did I make the wrong step? Like sliding doors vibes. Career sliding doors. And that is exactly what we're gonna hear today because I got an email recently from a guy that I worked with at my first job 20 years ago who I have not talked to since.

3:39And we're about to talk to him because he feels like he wishes he made some of the decisions that I made. Little does he know you don't wish you made some of the decisions you made. I don't think we're going to get into that, but let's hear from him. Sean, here's a thing I wouldn't have said 20 years ago because it didn't exist 20 years ago. I don't think podcasting existed 20 years ago. Welcome to Help Wanted. Thank you, Jason. I've been talking to everybody I work with now, like how I'm going to be talking with a guy today and 20 years ago, we were like almost the exact same position. We had both graduated from college.

4:18We're both starting our new career in the field of journalism at a small town newspaper. But things have definitely taken different paths for us. How did we end up in such different ways? And that's not to say your way is much better than my way or, you know, that I'm unsuccessful. But there are things that I wish maybe I would have done differently. So my question is now, how could I catch up? I haven't made the best career decisions in the past. And some other things have happened that have kind of made it so that I'm not where I want to be as far as my career goes. I really appreciate you reaching out and being that honest and vulnerable.

4:57And I think that what you're describing is something that a lot of people relate to. So you had originally reached out to me with a kind of summary of what had happened over the last 20 years. So why don't you share that with us so that we understand what you mean by you hadn't always made the best career decisions and where you are now so that we can start to talk through what matters to you and what to do next. And also, if you have any embarrassing stories about Jason along the way, please feel free to insert those. So if we go to the Wayback Machine to the Gardner News 20 years ago. Jason and I were both young reporters.

5:33I felt pretty successful there. If you've had to pick the ace of the staff at the time, it was me over Jason. I agree. I covered City Hall in our main city. I wrote massive amounts of stories. Jason already had big eyes back then. This was his stepping stone for sure. For me, it was my hometown newspaper. I always kind of feel a connection with my employers, like I'm very loyal in that way. And I had like this idealist view of local journalism and the battle we're fighting and the public service that we're providing. I was happy to be a local news reporter because it was so important. You were at the paper.

6:14You were very committed to it. At some point, you must have made a decision to leave because of some reason. Tell us, like, why did you leave and what did you decide to do next? The primary reason was money. When I started at the newspaper, I think I made$10 an hour. This is 20 years ago. When I left, I think I was making$12 an hour. And it just, it wasn't feasible. So like I said, I had a lot of relationships in the community from being a reporter. And one of those was at the police department and they had openings for police dispatcher. And to me at the time, the pay, I think it was like 40 ,000, which was significantly really more than I was making, you know, and I liked the people there.

6:54I had a good relationship. I'm like, okay, I will do that. So I took that position. I worked overtime. You know, I think I made$50 ,000 a year to me at that time. It was, it was good money. Yeah. You know, it's funny, Sean, just for what it's worth is that if we're tracking the two careers, I remember making$20 ,000 in that first job that you and I worked at together. And then my next job paid$40 ,000. So if you were getting 50, then your next career move was more financially savvy in a way than mine. Yeah. So I get the job at the police department. I immediately know I'm not doing this for the rest of my life.

7:28It was very monotonous. My favorite part of my job is I got to be an advisor for the Explorers program, which was a program that taught law enforcement to local high school kids. I really like working with kids. And I said, I should be a teacher. In Massachusetts, you don't have to have a teaching degree. You just have to pass the test. There's two tests you have to take. I passed both of them and I had my teaching license. I had a hard time finding a job for a while. And eventually I found a non-traditional school. My salary is$30 ,000 a year. I went backwards, but I'm like, that's okay. I'm a teacher now.

8:03It will work itself out. I start to find a lot of success at my job. A few years in, I get nominated for an award, a national teaching award. I created an organic garden for my students. We called it the Fresh Start Organic Garden. And it's amazing. And then the school was sold to another organization. The culture definitely changed. Fast forward three years and I can't really do it anymore. Like the kids have changed. And a former boss of mine is a principal at a public school and they had no opening. And I applied for that job and I got it. The salary at that position was$63 ,000 a year. I'll just fill in because I know what happens next.

8:41Because you told me, which is that you end up leaving teaching and then you became a paralegal. and you told me in your message to me that you were disappointed when after studying to be a paralegal and getting a job as a paralegal that it wasn't paying as much as you had hoped that it would, right? So that's the moment that you're in right now is that you've made a shift, got into the arena, and then discovered that there wasn't as much money as you wanted. Just to put a fine point on it, Right now, you said you're making$26 an hour, which I think translates to an annual salary of about$54 ,000 a year.

9:21Is that right? Yes. When you told me that you were a paralegal and that's what you were making, I went onto Google and I just Googled average paralegal salary in Massachusetts. The first thing that came up told me that the average paralegal salary in Massachusetts where you live is$58 ,000, which is not that far off from what you're making. Had you done any of that kind of research to know what you were getting into before you did it? Not really. So this was my research. I talked to an uncle that I have when my career change was happening. He's actually, he's very smart. And he said, you know, what do you like doing?

9:59And we talked about things I like doing. He goes, have you ever thought about being a paralegal? He says, I think they make like$75 ,000 a year. And me, I said, well, he's very smart. He knows what he's talking about. Yeah, but Sean, you're very smart, too. And you are a journalist and you know how to use Google. Yeah. Is there like maybe some mental disconnect or is it like that you don't want to really know? In my mind, I always kind of find ways to justify like, well, if they're doing the average paralegal in Massachusetts and they're including Boston and Boston's rates are going to be much higher than the rates in Worcester or the rates in Gardner.

10:35That's fine. I'm not going to drive to Boston to be a paralegal because I'd be spending so much money on the commute and my quality of life would be less. Maybe I have a hard time thinking, like, if I look that up, is it going to be accurate for me? Maybe. But that's also like, you know, people that don't step on a scale because they don't want to know. Like, also, maybe the scale is messed up. Maybe it's on a slant or maybe it's like a weird scale or maybe it's a digital scale or I don't know. Maybe it's like that's not the real number or something like that. And so I think some of this stuff is just like the enemy between your ears or like maybe something that's keeping you from actually knowing the truth.

11:15And I'd love to figure out what that is. Part of the reason maybe that I hold on to jobs is maybe some of that fear as well. Like I definitely could have left my job at the private nonprofit school many years before I did. And I think part of it was maybe it was insecurity about, well, I didn't go to school for teaching. Am I going to be able to go to another school and be okay? I wonder if part of the reason that you're doing this in the way that you're doing it is because of the fear of not having a plan and therefore feeling lost. Because what you have told us throughout this story of being a journalist and then being a police dispatcher and then being a teacher and then being a paralegal is that it sounds like what you did was you felt like you needed something else, something presented itself, and then you just ran towards it, which is totally understandable because the alternative is to say, oh, no, I don't know what to do, and then spend a lot of time thinking about it and researching it and talking to people and marinating in this lostness of not knowing where to go.

12:25And that is a hard place to be. An easier place to be is to say, ah, I'll go over there. And then, of course, the problem is that you discover what you didn't know when you're already there instead of before you went there. Does that resonate? It absolutely does. I can even tell you, Jason, I went to school for one year to get my paralegal certificate because I had the opportunity to do so. Applied for jobs as soon as I finished. And I took my second job offer. And I did that because I'm scared. Like, I need to get a job. And if we go way back, Jason, we talk about how our past diverged. I don't want to make a pity party for me, but I think our backgrounds are pretty different as well.

13:06I don't know your full background, but I know that, you know, your parents seem to be okay. I remember your dad was a dentist. Again, I don't want to... No, it's a good memory. Yeah. I think that this is an important thing that you bring up that I know Nicole can speak very intelligently to. So say what you're saying, because you're right. So my dad passed away when I was 20 years old and my mom wasn't in my life. So I was in college when my father passed away. My stepmother basically kicked me out of my house while I was still in college. Like I came home one weekend from college and she goes, your stuff's packed up.

13:35I don't know what you're doing, but you can't stay here. I was in a situation where I needed to have a job. I needed to know what was going on because I didn't have a safety net where if I went a significant amount of time without working, that I would feel like I'd be surviving. But I think that's a big thing. It's like, Jason, you maybe had more of an opportunity when we were starting out back then, like, hey, if I take a chance and something doesn't work out, I'm going to be okay. You are absolutely correct in that I grew up with two very supportive parents. My dad was a dentist, made good money.

14:11They did not roll out the red carpet for me on everything, but I knew that I could take risks in my career. And if something didn't work out, that I had a safety net. That without question enabled me to act bolder than I know some other people were able to. So Nicole knows exactly where Sean is coming from. Let's connect on this. I would love to be adopted by Roy Pfeiffer as the Pfeiffer clan. They are a fantastic family. I also didn't have that. My father died of an overdose when I was 11. My mother peaced out. I had no safety net. I resonate with this story a lot. I felt like I never had a couch to go back to.

14:53There was no plan B. There was no option. There still isn't. And it still drives me and scares me. And so for me, the way I've approached it is that I have actually optimized more for money because I've had to. And I've tried to go in saying that that is not a sellout, which is another episode of ours situation, but it's something that I need to get. It's not a nice to have. It's a need to have. And so I'm wondering, like, if we you and I kind of had a similar start in life, I would say. Is that fair? Yeah. And I also started in journalism and quickly realized that you can't make money there. But beyond that, I think that the next moves were driven by the necessity to take care of myself.

15:42So I'm curious, when you started talking with others, did you ever just sit with yourself and say, what did you want to do? Yeah, I mean, I'm not afraid to follow the things that I want to do. So actually, when I started in college, I was a business major. And I started working at the college newspaper, like in the business office, and they wanted to start a business page. And I said, I'll do it, even though I didn't study journalism. And I really liked it. And then so I added journalism as my second major. And I was actually still in college when I pretty much started working full time at the Gardner News.

16:19I was a correspondent, but I was doing four or five stories a week while I was still in school. I'm also very much like I see something new that I like and I'm all about it, but I can easily get burned out. Things catch my eye and it's like, well, I want to do that now. That's also hurt me in my career because I think about I don't want to get sidetracked, but my wife, who I love dearly, she did not go to college, but she's bright. she got a job at a corporation when she was 20 years old. She's worked at that corporation since then. She's a mid-level manager now, and she makes like$70 ,000 a year.

16:58And it only happened because she stuck with it. I think that you are looking back at yourself somehow beating yourself up, which you shouldn't at all. You've had a very colored career that every step of the way sounds like you were really passionate about. So you're judging yourself by something you didn't optimize for at the time. So you're being too hard on yourself for that. Like throughout your career, it sounds like you didn't optimize for money, right? But now you're looking back and you're saying, well, like I wasn't successful because I didn't make a lot of money. But that wasn't the driving force of your moves.

17:32That's true. You're judging yourself for metrics you didn't even know at the time. That's not fair to Sean. Let's be nicer to Sean. Even now, like I'm super proud of my current position. So Jason, we talked about how I told you I make$26 an hour now. I started here less than three years ago and I started at$19 an hour. That's great progress. As we're eventually going to talk about how to think through what may be your next career change and what you want to do, do you have a number in your head of what you want to reach? Because Sean, I will tell you, Nicole and I both experienced this and continue to experience it, which is that no matter what your accomplishment is and no matter how much money you make, it suddenly does not seem like enough because there's always more that you could get.

18:18So at some point, you have to know what you're actually aiming for. Do you have that in your head? I think I like to make like$100 ,000 a year. Okay. Okay. I'm happy with everything about my job except money. You've now switched and you said, here's my goal. It's$100 ,000. Your goal in the past, when you were coming up in your career in your 20s, was not that. You didn't have that goal. And so now you're switching. So let's say, okay, let's appreciate our former self for what he did. He did an awesome job. He did the best he could with the information he had. And now moving forward, we have like a different goal.

18:51The point that Nicole is making is that you can't tell this negative story of yourself where the punchline of it is and now you're stuck or now you've wasted so much time. Rather, everything that you did served some kind of purpose. You were pursuing passions. You were interested in things. You learned a lot about what you want and what you don't want. And it now informs the next decisions that you make. The question now is, starting from right now, what do we do? Stick around. Help Wanted will be right back. And here's where we would have an ad. But because this was a Help Wanted show that's just been dropped onto the Problem Solvers feed, I'll just remind you, this is a show called Help Wanted.

19:42You can find it wherever you get podcasts. Just search for Help Wanted. All right, back to Help Wanted. Welcome back to Help Wanted. Let's get to it. Now I want to think through how you make more money. When you reached out, part of your wonder was, is it time to just make another career change? Just do something totally different again. And look, maybe it is if you want to totally just optimize for money. But also, before you do that, I would want to step back and say, all right, what do I have here in the world of paralegal? Can I look around and see what other paralegals are making and where and what it takes to get there?

20:24Maybe some sacrifices do have to be made. You, for example, said that you don't want to drive into Boston, but maybe if you start pushing yourself closer to Boston and taking a longer commute, it translates into more dollars and ultimately the balance there is better. Or maybe some of the skills that you've picked up in paralegal work actually translate really well to some adjacent field that doesn't require a full reboot of what you do, but that ultimately does pay better or gives you access to better paying employers or something like that. So have you looked into any of that? I have not. I mean, I find it very helpful to make a shaded part of a Venn diagram.

21:03Like, what do you do? What can you do? What are the skills you have? What are the opportunities have? And what do you want? And there's always going to be a shaded part. And if now what you want is money, what are the high paying things that combine your skills? Is it teaching other paralegals? Is it making a class or writing about it or something? Can you smush all of the things you have for the highest salary possible? Have you thought of that? No. So thank you. You're welcome. Let's think about it. Nicole makes an excellent point. You know how to do a lot of different things. The story of your career is actually one of accumulating a lot of skill sets.

21:49And you haven't actually stepped back and said, how do these things snap together in a way in which they're all useful? Perhaps that's something I should be doing. Let's snap it together. I love writing. I like teaching. I do like imparting my knowledge on others. And I don't know if that's different than teaching. I don't want to get into semantics. It's different teaching children, I think. Teaching adults is a different thing, especially if they have the desire to learn. Maybe I've always not wondered, like, are people going to want to hear what I have to say? Would they value what I have to teach them, I guess, is the question.

22:25Again, this goes back to not sticking at things for very long. Like, I can't say, Sean has been a paralegal for 20-plus years. Come learn from him. Sean, here's something that I think you should do. You should look around and see what problems you can solve for people. Perhaps part of the reasons that you feel insecure is because if you don't know the problems that you can solve for people, then all you're doing is showing up and demanding their attention. And you don't know if they're busy or if they have a need or why they would care about you. But if you know the problems that you can solve, then suddenly you see a role for yourself.

23:00So what would a problem be that you can solve? I don't know that much about the legal world, but I do know this because I've heard it from friends who are lawyers or who work in law firms that lawyers do not know how to write in a way that is not a complicated legal brief. They struggle with communication. And communicating in a way that is not a legal brief is an important thing that people need to know how to do. and that includes lawyers. And that's the reason why a lot of law firms actually hire outside consultants to teach their lawyers how to write like regular human beings. Now, here is you, someone who has worked professionally as a communicator in a plain English kind of way, who also has developed the skills of a teacher to teach skills to other people.

23:54And you are sitting in a law firm or you're at least sitting in an industry, I can't speak to your specific firm, these are people who are probably very aware that a shortcoming of theirs is their ability to communicate in a non-legal way. Now we have identified a problem and you as a solution. And it might be worth even just volunteering or coming up with some kind of system or something that you can introduce at your firm, see if people like it, maybe you become much more valuable there. Maybe you take on a totally different role there. Maybe you create a whole department there. Or maybe you become really valuable in a way that they love but aren't going to pay you for.

24:36But now you have something that you can take somewhere else and say, ah, I am doubly valuable. I'm a really good paralegal. And also, I run this program teaching the lawyers how to write. And now somebody is going to pay you a lot more. That is how you take somebody's problem and connect it to the snapping together of the skills that you have accrued. I really like that idea. The law firm here is part of an organization that does like seminars and things for lawyers. And during the seminars, they always have people that present their products and things like that. And I could picture myself presenting my products like how to write like a human.

25:13Yes. How to communicate effectively with your clients, you know, or even developing templates that explain processes, you know, like you're getting divorced. Here's what to expect. Totally. And by the way, one of my favorite online shopping sites these days is Fiverr and Upwork. I love these marketplaces where I can find a bunch of really easy freelancers who can do things for our business. And as I was looking for writers on there, actually, I saw a lot of offerings for freelance writers who were specializing either in business or in law who could write these articles that I've actually stumbled upon recently because I've been searching like how to make a convertible note for an LLC or something like that.

26:07And so all these like random law firms in like Wisconsin or wherever, like have an article explaining this. And I can guarantee you the people at that Wisconsin law firm are not writing it. I'm sure they outsource that to some writer on Fiverr, like you could be, who has a particular expertise in some area. And they're now using that to put on their website to optimize for SEO and all this other fun stuff to get customer acquisition. Theoretically, I could do that while still being committed to my current job. It's something that you can start and then see how it goes. And maybe it turns out that it's wildly successful and I don't need to be a paralegal, but maybe it doesn't.

26:48And it just means it's a way that I can get to that number that I need to be at. You haven't quite figured out how to make the boundaries of what you think work are more flexible. I realized that getting ahead and making the kind of money that I wanted required doing multiple kinds of work at the same time. The Gardner News was the only job, that first job that we worked at, the only job I ever worked at where I just did that job. After that, I have always, including right now, freelanced on the side of whatever full-time job that I had, always. And that was where my extra income came from and that's where my advancement opportunities came from because that's what got me in front of the next set of people that were going to create the next set of opportunities.