How To Find a New Career Before It’s Too Late

Listen to this episode

S1: So where are you working right now?

S2: I am working at a restaurant here in Kansas City. Things are kind of up in the air in the restaurant world right now. So I’m just trying to find someplace that, you know, makes me feel safe where I can also contribute and make money. Because it’s a scary time.

S3: Welcome to How to. I’m Charles Stuart. More than 40 million people have filed for unemployment in the last few months. And for many people, this is a really rough time. But for some, this is also a period that’s helped them realize they never really liked their jobs in the first place or it’s prompted some people to start thinking maybe this is the nudge I need to find something new. But how do you do that when you’ve been doing the same thing for years or decades? How do you jump into a new career when you’re not in your early 20s and fresh out of college? That’s what this week’s listener is wondering.

Advertisement

S2: My name’s Danny. I’m a 38 year old single guy who wants to change careers.

S3: And because I wasted so much time, I feel a little too old to start completely at the bottom.

S4: You know, are they going to want to hire an intern? You know, that’s 40. That might not be able to contribute fully to the company.

S1: Donny has goals. He wants to find a girlfriend and settle down and have a family. And the first step, he thinks, is getting a better career because it’s hard to build a real life when you’re working nights and weekends. And so he wants to get out of the restaurant industry, but he worries it’s too late for him.

Advertisement
Advertisement
Advertisement
Advertisement

S4: I think a lot of it has to do with my lack of further education. I did eventually get my associate’s degree, but I don’t have a bachelors degree. Some of it’s connections, you know, the old saying it’s not what you know, it’s who you know. And then some of it’s just I. I don’t think that maybe they see that I have enough management experience.

S5: So so we we thought this is a really interesting question and a really important one right now, because there’s so many people who are looking for new jobs or who are trying to figure out how to transition. And so we reached out to Jessi Hempel, who’s a friend of mine and a podcast host at LinkedIn with a podcast. Hello, Monday. So, Jesse, you’re kind of like a guru right now of of thinking about work and thinking about how to get jobs and thinking about what we ought to to value in jobs.

Advertisement

S6: You can’t see me blushing over here. I think the word guru is a bit overstated. So for the last year and a half, I’ve been hosting this podcast called Hello Monday that really looks at the changing nature of work. Can when I started doing this, I thought this is going to be a show about I don’t know how to negotiate well, how to plan your time during a day to move up the ranks in your office. But it turned out to be a show about aspiration and inspiration, about what we’re really looking for when we’re looking for meaningful work. Very often it’s not what we imagine and about how we can proactively get there regardless of our background.

Advertisement
Advertisement
Advertisement

S7: On today’s show, Jesse will give Donnie advice on how to find the job is right for him, and she’ll give us some of the secrets that we can use to find the perfect career. Stay with us.

S1: So how many jobs have you had over the last, say, your 20s and 30s?

S4: A lot. I’ve worked in over 20 restaurants. I picked up a couple of different side gigs here and there did some marketing and promotions for a while. So probably closer to 30 jobs.

S1: Donny says that his nomadic work life and his late start in finding a career can be traced back to a couple of rough patches from when he was young. That really ended up shaping his path forward.

Advertisement

S2: My parents got divorced when I was very young. Mom moved back to California. Dad stayed in Oklahoma. And then it was just kind of a shuffle for me, really. There were times where my mom couldn’t afford me or I’d go live with grandma and grandpa. We spent a year in Minnesota. I wasn’t really ever in the same school for more than two years until I went to junior high school.

S1: Never really clicked for Donny. And then when he was 19, his mom passed away.

S4: It really kind of destroyed all my preconceived notions of what I was going to do and where I was going to go.

S2: I ended up getting my JD. I went to college for a little bit. Started working in a restaurant. Turned 21. That’s that’s kind of when when things took a little bit of a turn.

Advertisement

S4: You know, obviously, I was allowed to drink at that point in my mom’s health issues where, you know, she drank herself to to her death. So I just kind of bounced. Restaurant, a restaurant, couple other pretty cool jobs, added radio for a while. But that that was just another invitation to to get invited to the cool parties and meet the bands and drink and do more drugs. And I never took care of the pain that I that I carried around with me. So once I moved to Kansas City, I’ve just been working in restaurants for 15 years.

Advertisement
Advertisement
Advertisement

S5: And have you enjoyed that? Like, has it been a rewarding career for you?

Advertisement

S4: It is satisfying in a way. I can walk into a room and make friends. So that translates really well, especially behind the bar. But at the end of the day, it’s just like, you know, none of those people are actually my friends. And do you still drink? I do not. I will have two years of sobriety on July 17th. Congratulations. Yeah. Thank you. And what’s the best job you ever have? I was a patient care assistant at University Hospital here. It’s pretty much the lowest of the low level nursing skill jobs. But I loved it. It was it was taking care of people, you know, when they really, really needed somebody to be a helping hand. That was really rewarding. But the pay wasn’t sustainable, is it?

Advertisement

S5: Is there one moment that stands out like what was your best stay at that job?

S4: We got a guy who had had a stroke. Gentleman was probably in his 50s. He was a really, really tall, just kind of one of those like Paul Bunyan looking dudes. And he couldn’t talk. He’d be trying to communicate and he’d say, you know, might, might, might, might. And we tried to whiteboard where we write stuff down. And we were both frustrated, like to the point of tears. And it is time for my shift to be over. And I started to walk out of the room. And as I got into the hallway, I just kind of turned around and I went back in there and I said, listen, I don’t care how long it takes, you and I are gonna find a way to communicate. And I came back the next day and seven o’clock I knocked on his door and I said, hey, I’m here. And over the next couple weeks, we formed a really good relationship where we could communicate. And he always wanted to make sure that I was coming back the next day. And, you know, I think about that guy a lot. When I get into difficult situations.

Advertisement
Advertisement
Advertisement

S7: So, Don, he’s had a few setbacks, but he also knows what he’s good at. He’s great with people. He’s dedicated and persistent, and he’s eager to make up for lost time. So what do you do with that? How do you reinvent yourself when you’re approaching 40? That’s where Jessi Hempel comes in.

S8: The thing that struck me the most about what I heard Danny say was like this idea that he had wasted time along the way. And I felt like that myself at every turn because I never quite knew what I was going for. And I didn’t understand how all the mistakes I made along the way were setting me up to be smart about the things that I care about now.

Advertisement

S1: So for someone like Donny, right. Who’s facing this problem that a lot of people are facing. I think the first order question is kind of how should he be thinking about this?

S6: Well, as I listen to Danny, I was so struck by the aspects of his character that he has going for him. He is clearly somebody who is hard, knocks in life, have season 10 and who has an incredible amount of compassion for other people. And so when he says, like, I wasted so much time, my first reaction to that is you didn’t waste that time. You had a crash course in humanity. You you developed yourself. It might not have a degree attached to it, but what he got from that period of time is going to set himself up well for the next part of his career.

S7: This is the first rule. Recognize that your life experiences and your people skills, those are just as important as a college diploma. Employers want those skills. They need them. And being a salesperson or specializing in customer service. Those are the things we learn in life, not in school. The trick, though, is figuring out how to communicate those skills to a new potential boss.

Advertisement
Advertisement
Advertisement

S5: I think that reframing it that way. A crash course in humanity. I think that’s beautifully said. But how do you prove that to somebody before you can even get through the door? Because I’m imagining that when you submit your resume, Donna, you got you got twenty five different jobs over the last decade. For some people, that’s like a big warning sign. Right. But but just you’re exactly right. That’s actually like. That’s actually a way of saying this is someone who can like is adaptable. This is someone who’s resilient. This is someone who can walk into a new situation and thrive.

S6: I think in Danny’s case, a resumé is not his most powerful tool. He needs to spend time with you and it won’t take a lot of time before you’re pretty committed to his success. I can tell that. And so I would say spend your time developing relationships. This is a time for networking. And Danny is a person who is primed to develop a network. How do we do that?

S5: Because I know that you’ve spoken to a number of scientists and researchers who spend time thinking about, like the practicalities of networking. What do we know about how we ought to be networking, particularly during a time like this, when we actually can’t network in person?

S6: So right now, it’s a really amazing time to make new relationships that can serve you. And the reason is because we’ve all just been through something that’s left a lot of us a little more vulnerable, a little more nervous about the world, a little bit more in flux. And when people are in flux, they’re more open to new connections. And so whereas a year ago, if you called somebody you didn’t know out of the blue and said, hey, let’s do this thing together, maybe they’d be busy. But today, this moment, they probably have a little bit more free time or at least a little bit more emotional space to consider having a meeting with somebody new.

Advertisement
Advertisement
Advertisement

S7: This is our next rule. Now is actually a great time for networking. As long as you think about how to help the person you’re trying to network with rather than just helping yourself. People are nervous right now and they’re lonely. And so when we contact them, we should be aware of those feelings and anxieties. Expand your network by making real, authentic connections to daddy.

S6: Have you ever. Have you ever taken the time to do an informational interview with someone at one of the companies that you’ve applied for? I have not. Well, so this might be the first thing that I might suggest for you. One of the ways that people are often considered for jobs than companies is that they’re referred by people they know within those companies. How would it feel to you to just ask someone for a cup of coffee to hear about what their day to day job is like that would feel normal and comfortable?

S4: It might be a little awkward day to make that request, but it is a little awkward the first time you do it right.

S6: So I’ll often begin by saying I just want to understand what other opportunities are out there that I haven’t really thought through.

S7: This is our next networking tip. Ask people if they’ll talk to you, even if it’s awkward to make the request and then just ask them for advice because everyone loves giving advice. It’s easy to give. It doesn’t cost anything. And it makes us feel like a genius when someone says they want to pick our brain. But it’s important to find the right people to ask advice.

S3: And sometimes that takes some creative thinking.

Advertisement
Advertisement
Advertisement

S6: Scientists say, from my own experience, when I wanted to become a magazine writer, I went into Barnes and Noble because this was back when Barnes and Noble actually had racks and racks of magazines.

S8: And I would take the method of a magazine and I would count up three from the bottom because I would figure anybody at the top of that masthead is too important to talk to me and they’re not going to take my call. And anyone at the very bottom isn’t going to know a thing about how the place works. But if you get somebody who is just close enough to the bottom that they feel really important that you’ve called them, they’ll take your call and explain exactly how the place works. And I suspect every organization has their equivalent of that person.

S5: I love that. That is so great. So, Sudani, if you were trying to do something similar to what’s a new job where you think you could find someone to give you some some insights? Have you applied for any jobs lately?

S4: I have applied for for many, many different positions. I just I sent an application and the other day for for a job that I think I’d be well suited for the tech company that that builds platforms for tacos, for restaurants. So it’s a sales job where I’d be talking to restaurant owners and general managers about optimizing their to go sales.

S1: Huh. And if if you wanted to reach out to someone in that company, what would you do?

S4: Yeah, the the new restaurant that I’m working in, I looked at. They’re there to go tablet and it’s the same company. So I could I could find that rep that that set up that account and say, hey, you know, I’m working for this restaurant. You set up an account. I’d like to know more about what you do, because that person is very likely in the very role that I applied for.

Advertisement
Advertisement
Advertisement

S5: Yeah. That’s a great idea. And in fact, you might even be in a position where they want to talk to you because you’re a client to write their perspective. It’s like, oh, I get to do more business with these folks. But but, B, I imagine that getting a getting a referral from an existing salesperson to say, hey, look, I met this guy, he could be a great salesperson for us. That’s probably going to be be much stronger than just sending in your resumé and hoping that hoping that it catches someone’s eye. Yeah, this actually reminds me of something I used to do when I was applying for jobs. I would always make sure to FedEx my cover letter and resume to the hiring manager because I knew that they were more likely to open a FedEx envelope because, you know, everyone loves getting like a an expensive FedEx in the mail. Right. And that meant that they would at the very least, hold my application in their hands. Okay, so then then there’s this next question, Jessee, which is so let’s say Donny does that he sort of finds a connection. He knows that the the person in charge of hiring is actually going to look at his resumé because he’s been recommended by the the existing sales person there. And Donny had mentioned that he feels like one of the big weaknesses of his resume, of his applications is that he doesn’t have a bachelors degree. What do you think he should do? We’ll get that answer and hear more about how to handle weaknesses in our resumes right after this quick break.

S3: Hey, everyone, if you like this show and you’re looking for more help to manage the difficult problems in your life, you should check out the Savvy Psychologist podcast. Dr. JDA will provide short, actionable tips and evidence based research to help you develop a healthier emotional life. If you’ve been feeling overwhelmed lately, you should check out a recent episode, Eight Strategies to Handle Anxiety and Settle Your Mind. And she also covers topics like How to Say No Without Feeling Guilty and how to manage grief and loss and how to get better quality sleep. Dr. Wu’s practical advice can help you be happier and healthier and most importantly yourself, just search for savvy psychologist wherever you get your podcasts.

Advertisement
Advertisement
Advertisement

S1: We’re back with our job seeker, Donny, in our expert, Jessi Hempel, host of LinkedIn hello, Monday podcast. And Donny is a lot of interesting life experience, but he’s worried that he’s going to have trouble overcoming his lack of a bachelors degree.

S6: Well, it’s interesting, Danny, because I think that I can tell you that one of the things that we are seeing at LinkedIn is that companies care less and less every year about bachelors degrees. In fact, Google recently said that a bachelor’s degree is no longer necessary and order to work there. And so it starts with you and your own self-confidence about your story. So if they do ask, well, why didn’t you get your B.A.? How would you answer that right now, Danny?

S4: That’s a tough question. I would say that my life circumstances at the time did not afford me the luxury to spend the extra years and the financial commitment to pursue higher education. Nailed it. But to get answer, that’s a great answer.

S6: You know why it’s a great answer? Because it is true and it is brief. You want to be clear. You want to be concise. You don’t need to give a lot of backstory. And in fact, if you give a lot of backstory, you flag that you have a discomfort with the situation.

S1: Danny, one of the interviews been like for you. Like, do you feel like you’ve done pretty well or or is that where you feel like you might be stumbling?

S4: You know, interviews generally go pretty well. The best interview I had was for the hospital where I had zero experience in healthcare. They had asked me what I would do with an angry patient, and I ended up quoting Yoda. Your fear leads to anger and anger leads to hate. You never asked. They said that was the that was the key to me getting the job.

Advertisement
Advertisement
Advertisement

S6: I think from how Danny describes in interview, I suspect that his natural skills give him a great foundation for interviewing. I think a couple of things might really help him strengthen that. One is that the most important thing that you can do when you’re interviewing is listen. Well, and that sounds like one of those things. So just listen well. But listening is really hard and it’s even harder when you’re nervous, which mostly we are when we interview and you do want to come off confident. But there is a fine line between confident and cocky at the same time as you let your personality shine through. You want a flag to them to communicate to them that you really respect the opportunity that they have on offer.

S7: Here’s our next rule. Be a good listener. Be attentive to both verbal and nonverbal cues and be ready to ask questions of your own. And when you ask a question which hopefully shows that you’ve been listening during the interview, try to make it something that conveys how lucky you would feel to get this job.

S6: Oh, here’s a question that I love. Tell me about the best work day that you had in your last job. And this is a great question, because if you say tell me about the thing you liked best about your last job, you’ll get a pat answer. But if you ask this question, people will begin to actually talk about the pieces of the process of the work that they like. And that tells you whether you’re actually going to like to do the job.

S5: And once the interview is over, remember, your ability to learn from it isn’t over.

Advertisement
Advertisement
Advertisement

S6: Let’s say Danny has been referred by a friend who works at the company or somebody who’s become a friend and doesn’t get the job. What will happen invariably is the hiring manager will go back and say he has a good interview, but he blah, blah, blah, blah, and you want to know what the blah, blah, blah, blah is. And so it’s a good thing to circle back with your friend and and and do it in a way that doesn’t put them on the spot. Thank them for the opportunity to interview and say what’s going to help me to get the next role. What did you learn?

S1: If a job interview doesn’t turn into a job offer, try to get as much feedback as you can to improve for the next one. Even when it’s painful to hear.

S6: And I would add that all of this is a numbers game to some degree in the same way that if you want to get married, you need to go out on a lot of dates. Finding a job is kind of like that. And I find when I talk to people that the people who run at it tend to burn out quickly. And Danny is in this great position right now because he’s got a paycheck. He has a job right now. And so one thing that I would think about in this process, too, is, is spacing this out. Choosing a dedicated period of time. You’re going to work on this. Maybe it’s two hours a day, three days a week, and working on it during that time and letting it go the rest of the time.

S1: OK, so let me ask you this other question, which is what kind of jobs should he be looking for? Jesse, as you’ve talked to people about hiring and as you’ve talked to people who have had these really interesting careers. What have you learned about what a career is supposed to be in our lives?

Advertisement
Advertisement
Advertisement

S6: It’s a great question, particularly because I think there is this myth that exists that a career is supposed to be a complete fulfillment, this embodiment of who we are as people. And what I hear more frequently is that. People want purpose from their work. And people want economic stability. And it doesn’t always come in the package you expect it to come. A guy I know came to New York to be an actor and had some success. But then he took an inventory of those skills and he realized creativity, sort of thinking loosely about new ideas could be applied to software coding. And so he took a boot camp. It was a six month program. Cost him ten thousand dollars. He did not have ten thousand dollars. He borrowed it. He lived very frugally. And three years later, he is a very successful software programmer. And the interesting thing about it is that he finds that he’s using the same skills. But the thing that he thought he wanted to do with them didn’t bring him happiness. The thing that he’s doing with them now does that’s really, really interesting. And I think as I listen to Danny, I think I imagine that he is set up for a lot of success in the future, because already, as he talks about what he wants to do next, he acknowledges that it may be in sales, but that’s as close as he gets to boxing himself in. He understands that there are a lot of things he might be able to do that might bring him satisfaction. And that’s where you start who’s who’s happy, what they’re doing and who’s kind of like me out there.

Advertisement
Advertisement
Advertisement

S7: And this is the last rule. If you seek out people who seem happy in their jobs and in their lives. And you ask them how they got that way. You might learn about a career that never occurred to you. You never know what you’re going to learn or who you’ll learn it from.

S3: And once you do find those people, start networking from there. Danny, if you were to call someone tomorrow who seems like you.

S5: And it seems like they are happy at their job. Who would that person be? My friend Cynthia. Yeah. And if you called her and you said, you know, what other companies do you think I should apply to?

S1: Do you think that she would have some suggestions?

S4: I think that she’d be able to come up with a list. You know, she she’s been my biggest cheerleader throughout this process. She’s helped me off my resumé and she’s been very encouraging.

S6: So I wonder if she becomes a window into new relationships. If you say to Cynthia, OK. Now, can you give me one person to have a cup of coffee with? I bet she might she might be able to refer you to one person you don’t know.

S4: I can tell you exactly who she’d refer me to. She has a friend who’s a roaster. So she’d send me down to their coffee shop.

S6: So then you sit with the roaster and when you leave that meeting. What if you say to that person who’s the one person you know, I should have a cup of coffee with?

S1: Yeah, that makes a lot of sense. In other words, it’s easy to get hung up on finding a specific kind of job, but sometimes the best careers come from being flexible and curious and letting other people lead us to opportunities we never would have dreamed up on our own.

Advertisement
Advertisement
Advertisement

S6: You know, listening to you, I am just so impressed by your tenacity. Up until this point. And you’re still under 40, which I know might feel 38. Might feel old, but you’re still really toward the beginning of your career. You can take a lot of risk. It’s a good time to do that. And so my advice to you would be to see all that you are and all that you have and feel really good about it. As you look for the next thing, because the next thing will come, you’re doing all the right things.

S4: Yeah. Thank you very much. That’s very affirming.

S5: Yeah. And I will say, I know that there’s a lot of people listening who who are in very similar places to you, Danny. And and we’re scared and we’re anxious because we don’t know what’s going on with the economy. And it’s so hard to be home. And it feels like you work and you work and you send an application after application. And the stars just never align. That doesn’t mean that we’re not doing everything right. It only takes one person to say yes, right. It only takes one perfect date to find your spouse after 20 or 30 or 40 terrible first dates. And it only takes one person who has a job and is hiring to see how special you are and say you’re the right fit for this new job. Yeah. Looking forward to that day. We do talk about those horrible first dates. I’ve got a whole bunch of other if you want to do another episode to another show. Yeah, absolutely.

S3: Thank you to Donny for sharing your story with us. And it Jessi Hempel, for all of her fantastic advice, you should make sure to look for her podcast. Hello, Monday, which comes out every Monday from LinkedIn. And we check back in with Donny about a week and a half after he had talked to Jesse. And this is what he had to say. Hey, Charles, it’s been a really busy week since we’ve talked. I’m scheduling informational interviews. I’m doing a little bit of networking with some different groups that maybe I wouldn’t have thought of before. So that was really great advice. I want to thank you, Jesse, for helping me with that and really looking forward to what’s coming next. If you want to help us continue helping people like Donny, we would love to encourage you to sign up for Slate. Plus, it’s just thirty five dollars a year and it lets you listen to this and other podcasts ad free. You can find more information about it at Slate dot com slash. How to. Plus. Do you have a problem that we might be able to solve for you if you do? We want to hear about it. Send us a note at how to at Slate dot com. And we will do everything we can to try and help. How TOS executive producer is Derek John. Rachel Allen is a production assistant and married. Jacob is our engineer. Our theme music is by Hannah Brown. June Thomas is our senior managing producer and Alicia Montgomery is executive producer of Slate podcasts. Gabriel Roth is Slate’s editorial director for audio. I’m Charles Duhigg. Thanks for listening.