Jason Pfeiffer
speaker
203 appearances
4 recordings
1 series
first heard Nov 2024
last heard Dec 2024
Jason Pfeiffer’s voice in public audio — every appearance, attributed to the second.
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Appearances
This 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.
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. 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?
Career sliding doors. And that is exactly what we're going to 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. And we're about to talk to him because he feels like he wishes he made some of the decisions that I 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.
I really appreciate you reaching out and being that honest and vulnerable. And 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.
You were at the paper. You were very committed to it. At some point, you must have made a decision to leave because of some reason. Tell us, why did you leave and what did you decide to do next?
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.
I'll just fill in because I know what happens next because you told me which is that you ended 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. Is that right?
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?
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.
And 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.
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.
You are absolutely correct in that I grew up with two very supportive parents. My dad was a dentist, made good money. They 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.
It'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?
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