32: How to make a career change after 50

Some of the most listened to episodes of Career Switch Podcast are those that feature guests who’ve switched industries or professions after age 50. So, I decided to dedicate an entire episode to making a career change when you’re over 50. 

I speak with Penny Kastaris, executive coach and senior consultant with Right Management Talent Solutions, a company that offers career transition services.

Penny is a young Boomer, who helps over-50 clients with their career change, whether they know what they want to pursue next or are lost.

In this episode, Penny addresses the most frequent concerns she hears from her clients and offers her best advice for making an over-50 career switch.


Resources:

Assessment tests: Hogan, Birkman, Myers-Briggs

BetterUp: Changing Careers at 50? Here’s Everything You Need to Know

Indeed: Should You Make a Career Change at 50? Tips on How to Do It Successfully

Monster: The After-50 Career Change

Yahoo: How to Make a Career Change After 50

Additional Over-50 Episodes:
 Ep 4: Aged out: Making a career switch at over 50
Ep 16: Starting a new career after 50
Ep 18: The pros and cons of being a full-time author
Ep 21: A side hustle results in a career switch
Ep 23: How being bilingual helps your new career
Ep 41: Pursuing your passion at any age

Music credit: TimMoor from Pixabay

Podcast info:
What's your career switch? What do you think about this episode and the show? Tell us at careerswitchpod.com. Follow us on Instagram, Facebook, and LinkedIn.

Transcript

Lixandra: Hi, everyone. I'm Lixandra Urresta, and this is Career Switch Podcast. This show is here to encourage you to take action with whatever career change you're considering or working on. Maybe you're trying to switch industries or professions or break out on your own and start a business. In some episodes, I talk to people who've made their own career switch, whether by choice or circumstance. They share the good, the bad, and the truth about their journey, including what worked for them and what didn't. In other episodes, I speak with experts who offer their best career advice on challenges that can come up during the process of making a career change. After all, it takes guts to switch things up, and it's not easy. However, it is possible. 

So, I hope you hear something in this episode, an idea, a suggestion, a piece of advice that'll spur you into action with your own career switch, whether it's taking that first bold step or trying something new. Welcome. I'm glad you're here. 

Some of the most listened episodes of Career Switch podcast are those that feature guests who've made their career switch after age 50. So I decided to dedicate an entire episode to making a career change when you're over 50. Here to help is Penny Kostaris, executive coach and senior consultant with Wright Management Talent Solutions, a company that offers career transition services. Penny is not shy about calling herself a young boomer, and she knows firsthand how to transition through the different phases and market changes of one's career life cycle. She began her career in journalism, media, and marketing, and eventually made her way into talent management and human resources. Today, as an executive coach, Penny helps clients who are over 50 switch industries and professions. In this episode, she offers her best advice for making an over-50 career switch. 

Hi Penny, thanks for joining us today. Let's dive in. What state of mind do your over 50 clients have when they start working with you on making a career switch?

Penny: That is an excellent question. And I must say there are different answers, just like there are different people. For some people, they really embrace it and it's like, oh, all right, now this is the first chance I could really do what I wanna do and I might not have some of the constraints I had in the past. And for others, it could be a scarier process where they're dipping their toe in the water and just wondering how they are gonna compete both with their skills and people from different generational groups.

Lixandra: Let's talk about both groups. First, for those clients who see being over 50 as an asset, what advantages do they have?

Penny: You know, there's actually a lot. If you listen to AARP or a lot of the other research that's coming out, they're thought of more stable, more reliant, less likely to go someone and not show up for work or, you know, be off every Monday and Friday. So that reliability, their breadth of experiences could be a really strong plus.

Lixandra: And for those clients who see being over 50 as a disadvantage, what are they worried about?

Penny: You know, a lot of really natural things, especially if they haven't been in a situation where they had to look for another job before or had many years of service. Some fear over is there going to be ageism? Are my especially computer skills up to date? What if my manager, the hiring manager, is younger than me? How am I going to fit into a certain group? And here again, we don't want to generalize, but usually what happens is, yes, there's misperceptions of everybody, and there is even different biases in the market, but we don't have to accept that. So, for example, One of the individuals that we were working with was the age of the grandfather of these two partners that started up the business. And what he was asked in an interview is, well, are you going to feel comfortable with all these much younger people around you? And he said, not only am I going to feel comfortable, what I'm going to give you is to make sure that your financials are in place so you can pay them. Because many, many startups that could be very profitable, they can't always make payroll. So he said, try me out, try me out a few months. If it doesn't work out, it doesn't work out. And three years later, he's still the CFO in this startup.

Lixandra: So that's a case that shows how experience can be a definite advantage.

Penny: Yeah. And you know what? I love that movie with De Niro, which is the intern where the intern was someone that was retired, but it just goes to show that there is so much value in our experiences and we do not have to be limited to any age to be successful in today's market.

Lixandra: Going back to the second group, those who see being over 50 as a disadvantage, how do you address some of their concerns such as learning new skills and ageism?

Penny: The really big thing that we work in our practice at Wright Management Talent Solutions, and in my particular practice, is having a whole person mentality, meaning that we talk about facts, we talk about strategies, we talk about markets, but we also make it safe for people to talk about their feelings. So it's really asking those questions in a safe environment. You know, what is it exactly that you're concerned about? So let's take those separate items that you talked about. Again, we don't want to generalize. I have friends that are like 15 years older than me, even though I'm a boomer and their tech skills are unbelievable. But if it's a skill gap, then we talk about how building that muscle and not only building that muscle, but going to the targeted industries that they'd love to work in and see what those industries are using. So it's not only you're enhancing your learning, but you're becoming more marketable. And then looking at the age situation as well, you know, sometimes people will say something like, oh, it's age discrimination. And sometimes it is, but a lot of times it isn't. Those other times when it isn't is because individuals may need to make their branding stronger so that it's a better fit for the hiring organization and also fight against any kind of preconceived stereotypes or misinformation. I had a situation where a former president of a major hotel chain was competing with MBAs right out of school. In his profile, both on LinkedIn and other places, we talked about, hey, talk about that you're a pilot. Talk about that you're an avid sports person and you play tennis. So whatever those stereotypes are about being exhausted or not knowing about technology, you want to be able to counter that so that you have the best shot at the best fit job at the best fit compensation level.

Lixandra: When we first spoke, you also mentioned tech bias. How do you help your over 50 clients with tech bias?

Penny: So the first thing I try to do is get a sense from them on what their comfort level is. You know, if they're uncomfortable, what is it exactly that concerns them? Is it something that will help from a skill point of view? Is it just because they've done things a different way? I noticed in my own environment, and I'm dating myself here, but when a lot of the smartphones first came out, what I noticed with my friends that had kids, they were much more limber when it came to texting because none of their kids would use the phone for voice. They'd all use it for text. So that skill then got transferred to other platforms as well. To clarify, it's understanding the root causes of their concern. Is it a learning situation or a learning gap? We address that. And then finally, just practice and your approach. I know that even in many cases of brilliant people that I worked with, it was like, oh, gross. Now I have to learn a bunch of new things. But if we remember a time when we were little kids, and even if we fell 10 times and we were learning how to walk, everything was an adventure. So changing that mindset and, hey, this is going to be cool. I'm going to learn something, even if I don't get it immediately. And guess what? This means I'm going to take back my power and also be able to have a higher level of longevity in my career and better compensation. Total different mindset than I can't believe I have to learn this new app.

Lixandra: I like the suggestion you made when we first spoke that you should pull out your iPad or some other high tech device during an interview. Tell us about that.

Penny: Yeah, I love this. All right. It's a little theatrical, but sometimes the way to break down biases is by showing, not just telling. So, for example, if you're the most senior age person in an organization, You can come in and when they first start the conversation, you don't know if they're thinking how technical is Penny, but even saying something like, I'm so happy to be here. I'm just double checking that I've got both my watch email on off as well as my iPad. It will show them right away. Another example of that, not age related, but gender related, is we had a terrifically strong project manager. It happens that this person came out of the high end of candies and chocolates, but was going into the rough and tumble real estate and construction market in New York. Now, this person, if you looked at him, they're not even a hundred pounds soaking wet. So one of the things I had suggested that they do both on their LinkedIn and in answering some of the questions is to say that they were a sergeant in the Navy and they had something like 600 men reporting to them. So they know this person, even though they look petite, has a lot of grit that they're coming from. And that also is a way of reversing some of those unfounded misunderstandings, stereotypes, any of the above. And you know what? I personally, when I go into interviews, I love having the opportunity of turning around a perspective. There are some people, there's nothing you can do. You can stand on your head. You can walk on water. They're just too ingrained into the vision of who they want. But there's this big metal group of people that you're going to be memorable with. If you are able to clearly identify their work needs and how you fit into that, even if you look different and sound different than who they originally thought they wanted.

Lixandra: Okay. A lot of my over 50 guests have had to make a career switch after getting laid off and they had to figure out what to do next. How do you help a client figure out their career switch?

Penny: There's several factors that go into that. The first factor is knowing yourself. Instead of necessarily just doing ambulance chasing, you know, I need to make 250,000 a year. So I'll just go into Google and see what kind of jobs do that. It's really knowing what your superpowers are. That's number one. The number two is going into the market and seeing what kind of jobs are in demand. And if there's something that you do have to really highlight that in a wonderful way that's relevant. And if it's something you don't have, can you pick it up as a skill? Can you volunteer? Is it less critical than something else that you do have? And the number three to help this all happen is there's also assessment. So there's assessments you could take out there. There's the Hogan, there's the Berkman, there's the Myers-Briggs type indicator. But I also use something simple, which is I ask my clients to make three columns. So the first column says, what are my superpowers?

Lixandra: How do you define superpowers?

Penny: OK, those are the things that if you were to talk to other people, they're like, oh, you do that really well. So what is it that really makes you stand out? I would start asking family and friends and maybe even people you worked with. Let's say my own case superpower that I have is I call it polite persistence. I don't beat people up and yell foul language for them to say, I'm here, I'm here. But I don't give up very easily. And that is also important in job search. And it's important with a lot of different types of jobs. So superpowers, think about any evaluations you had. What did people tell you about yourself? Is it a certain role you take on in the family? Like, you know, even though you're not the doctor, are you the one that helps your relatives with their insurance and navigating their medical stuff? Are you the one that's a great teacher? Whether they're your own kids or you're coaching, or whether you're coaching someone at work, even if your title is not supervisor or coach. So those superpowers are what are internal to you.

Lixandra: Okay, great. That covers the first column. What about the other two columns?

Penny: The next column is what you want to bring into your life, what you do want. You're going to look at not just the work itself, but do you want to be virtual? Do you want to be hybrid? Which means sometimes you're virtual and sometimes you're in office. you're not necessarily going to have 100% power over some of those things. But a lot of times people have more of a say than they think so. What kind of flexibility do you want in your job? What kind of work-life integration do you want in your job? You know, those are things that will inform you. So again, you're not just ambulance chasing, but you're coming up with a grid or some ideas that will offer you best fit and not feeling like you're just going to have to settle for anything because you're over 50. The third column is things that you want to avoid. Now in reality we know as adults you're not going to get everything you want and you're not going to be able to avoid everything you don't want. For example, I had a candidate love to travel, but had sick parents. And so her rule was she did not want to travel anywhere where she couldn't get back to Florida in less than a half a day. So if somebody said, look, I have this really great consulting gig in Dubai, but you got to be there two months straight, that would be a no.

Lixandra: Let's now look at the flip side. How do you coach your over 50 clients who do know what they want to do next career-wise?

Penny: The same way. The first thing I do, whether you're lost or whether you know exactly what you want, is to drill down and find out what is it specifically that makes you excited about being a teacher? So it's, first of all, clarifying what they're looking for, so we're on the same page and I don't have any unvetted assumptions, asking them how they're moving forward, if they are, what they're trying, what's been successful, and then also working with them on other strategies that the research has said is the most successful. And one of those things is called networking, because there's something like 70 to 85% of the jobs, even though there's a lot on LinkedIn, on the job boards, they're out there. Some of them are not even public. and the ones that are public, if you could give it a human face, a human connection, you're at an advantage. So first of all, what I try to do is demystify what networking is, because a lot of people are just plain intimidated by it. So I say, you know, you don't have to wear a tie. You don't have to put on lipstick. Networking is just talking to people. So we talk about there's like an A, B, and C group of individuals we know. The A are people you know well. Those are people that you're familiar with. You know, you don't have to do like this whole song and dance of my name is. No cold calls. They've known you. Maybe they've known you for years. And I've known people that they got their job leads through an a contact by just opening their mouths and saying they're looking for work that a contact didn't know. So let's say, Alexandra, you and I are both in the same jazzercise class or, you know, you're my next door neighbor. or you're a co-worker. So I would say something like, hey, we've worked together. You know, you really know who I am as a person, and I respect you as a talent. I just have a couple of questions for you as I'm trying to clarify where I want to go from here.

Lixandra: OK, and who are in the B and C groups?

Penny: B, that stands for bridge. B people That's someone that you know that knows someone else that you might not know. And a lot of the jobs happen because someone you know will introduce you to somebody else. Oh, you know what, that person was in my sorority or fraternity, or that person's my neighbor, or you know what, my cousin does that. So those are bridge people. They may or maybe they don't even have a job, but they can help you progress through your job search. And then the C people includes hiring managers, recruiters, people that can influence or hire you. So those are the three levels.

Lixandra: Now, you also help your clients come up with questions to ask when they network. What are some of those questions?

Penny: So I'll give you my top five and it doesn't have to be at any order. Every single time, try to ask for a reference. So at the end of the conversation, it shouldn't be the first one, like, who else should I talk to? At the beginning, before you even ask any questions, you need to frame it. So, hi, I'd love to talk to you, Mark, because I understand you're very strong in the animation field, and that's been in my interest. And then you followed up with something about you so they know you didn't just trip off the bus and you have some skills very, very short. And finally, you take them off the hook by saying, I don't expect you to get me my next job, but I'd love to get your insights. You want to lower the expectation and frame it. So again, the first thing I'd ask towards the end is who else should I be talking to? And may I use your name or, you know, I'm fine without using your name. So if they say, well, my ex spouse has openings, but he or she is not too happy with me. Yeah. Don't use their name. Or if they're a competitor, don't use their name. The other question that you want to ask is in a very conversational way, like, well, how did you ever get into that role or company? If you ask it in a way and you've already built rapport, that can decrease the stress from the other person because they're talking about themselves. But you also want to listen attentively if there's a certain recruiter they used or if there's a certain strategy that may be helpful to you as well. The third thing I like to ask about is fit. And you want to ask it in a way that doesn't sound parent to child. So you're not going to say something like, Hey, if I have a four 30 doctor's appointment, is that going to be a problem with me as the head of operations? No, you're going to have something like, tell me what the culture is like during crunch time in this organization. Hopefully they'll say, do you need FaceTime, what it's like, and that'll give you a clearer idea. You can also go into Glassdoor and, you know, see what their employees say. So it'll give you a clearer idea of what's going on. The other question that I would say, number four is market data. And this you need to ask to multiple people, you know, cause some people see everything with rose colored glasses and other things, you know, life sucks and then you die. But it's asking them what's hot and what's not in the industry. So you're going to look at your own interests and skillsets and obviously lead with those things that you do well, that are in demand in your targeted area. And then lastly, and this one you may not ask, I call this the sex, drugs and rock and roll question. It's around comp. You'd never say, Penny, how much do you make as a coach? That would be inappropriate. But if somebody came to me and say, look, everybody that I'm interviewing with wants me to give them a range of what I expect to make, where can I go that could get that kind of feedback? Or someone with my background and experience and skillset, what do you think would be in the range?

Lixandra: Okay, Penny, thanks so much for that crash course in networking. As we wrap up, what would you like to tell our listeners who are over 50 and are working on their career switch?

Penny: My biggest thing is for people not to be defined by the outside and to not be afraid to explore things that are better fits for them. If there's any time to reinvent yourself, the time is now, and especially those of us that are over 50.

Lixandra: Thanks to Penny Kostaras for being our guest today. Check out the show notes for resources and for episodes that feature guests who made their career switch after age 50. 

You can find links to the resources mentioned in this episode and more helpful information in the show notes and on our website, careerswitchpod.com. So what's your career switch? Are you motivated to take action after listening to this episode? Tell us at careerswitchpod.com. We'd love to know, along with any feedback you have about the show. Let us know too, if you'd like to be a guest. Follow us on Instagram, Facebook, and LinkedIn at careerswitchpod. And please rate, review, and share with your friends and colleagues. It'll help get the show out there. Thanks for listening today. Till next time.