622: Career Change at 50: From “Too Old to Change” to Multiple Options (3 Real Stories)

Scott Anthony Barlow 00:00

At 25, career change feels exciting. At 50, it feels terrifying.

Scott Ingham 00:06

I've been doing the same job for about 18-19 years, and I'm like, you know, I'm getting towards, you know, an age where people don't normally switch jobs unless they're forced out the door.

Scott Anthony Barlow 00:20

It's not normal to change work after 50 because people fear they'd have to start over, or that it's risky, or that employers won't value their decades of experience. But what if those fears were just distracting you from a far greater game?

Bob Kalish 00:35

I'm reaching my, you know, into my 50s now. What did I want to do, right, with the last 10 years? What do I want to do next? What's going to fulfill me? And it just kind of keeps building momentum. Building momentum.

Scott Anthony Barlow 00:51

What if the experience you've accumulated at this stage in life meant that it was actually the best possible time to make a change that benefits you?

Scott Ingham 00:58

I was just like, "This is what I'm looking for in a position, in a company, in a company culture."

Carolyn 01:04

I absolutely love the team I'm working on.

Scott Anthony Barlow 01:07

Career change after 50 doesn't have to mean starting over from zero. It also doesn't have to be risky. In this episode of the Happen To Your Career podcast, we're going to cover why some of the most successful career transitions happen after 50 years old. I'm going to share three different stories that challenge everything you think you know about career change later in life. You'll hear from Scott, who left pharmaceutical sales after 18 years in his early 50s. Carolyn, an engineer with 35 years of experience, who left engineering entirely before finding a way back to what she truly loved. And Bob, he stepped away from a 24 year career leading restaurants to experiment with consulting. Each took a very different approach. One made a strategic industry shift. Another returned to her core passion within the same field. The third, turned his expertise into a portfolio of opportunities. Their stories are going to help you answer something that I get asked about all the time. If you're miserable at work but have decades invested in your career, shouldn't you completely change directions, or is there a way to shift what you're doing while leveraging what you've already built?

Scott Ingham 02:17

I was just like, "Hey, I've been doing the same job for about 18-19 years." And I'm like, you know, I'm getting towards, you know, an age where people don't normally switch jobs unless they're forced out the door. And so he was a great help in that, and always redirecting my mind, my set on that. And I think that was one of the, you know, most important things. And part of, you know, being part of the process is having a coach, is having, you know, someone like him, because you could easily get frustrated doing the legwork yourself, and then be like, "I'm too old to do this. I might as well just stick it out."

Scott Anthony Barlow 03:02

So this is exactly the mental trap that catches so many people after 50, the assumption that age automatically limits your options. But here's what Scott discovered about the reactions he got when he announced his decision to change careers.

Scott Ingham 03:17

Usually people, typically in their early 50s, are like they're, you know, they're gonna stick it out. And I told all my friends that I was doing this and reaching out to people, and they're like, "You're crazy."

Scott Anthony Barlow 03:28

Sound familiar? The people around us often become our biggest obstacle to change, not because they're trying to hurt us, but because they're projecting their own fears, their own concerns, often coming from a place of care, but that limits our situation. Because the reality is, we've got people, left and right, who are in their 50s and 60s and 70s that are not completely happy with where they're at and feel like they're sort of stuck. Often the reality is, you might be surrounded by other people in their 50s or 60s or 70s, and they might have good advice, but that advice is also filled with their own views and own ways of looking at it, and they often can't see outside that. And that's where looking at experiences like Scott's. It reveals something crucial about how we think about career change after decades in one field.

Scott Ingham 04:22

I think that stigma is still out there where, like, when I left my accounting job, the company was, to work at that company at that time, was a very sought after job. And most people that started in there, they started, and they put their 30 years in, and then they were done, and they walked out the door. And I wasn't like that. I think a lot of people were like thinking I was crazy because I left, and I totally did, you know, 180 and changed industry. I mean, something totally different than my career. So, yeah... So, and then, you know, I started this, and the same thing happened after, you know, putting 18 years into, you know, this company that my previous company, and telling people I left, they thought I was kidding when I was saying I was leaving and starting. And, you know, it was interesting because most of the responses I got were people were making excuses for why they were staying in the role they were staying, which indicated to me that they were unhappy with what they're doing, but unwilling to make that change. And so, it does take a lot of effort to do that. There's no doubt about that.

Scott Anthony Barlow 05:53

When everyone was projecting to Scott that a career change at his age was crazy and just a wild idea, how do we get the courage to go against the societal norm? We'll finally push Scott over the edge to actually make the change.

Scott Ingham 06:07

I think I just got finally sick and tired of dragging my feet. And there wasn't really a point in time, you know, a specific moment. I think I just was like, "I got to do this. It's either now or never to do this. And whatever happens, happens. And, you know, and we'll go from there." But I, at least, wanted to go down, you know, trying to do that. I think many of us out there who are not happy with our jobs, and it's so much easier just to continue doing what we're doing versus this is the big scary thing, and takes a lot of effort, but it's also very scary because there's a lot of change that goes on, whether you're staying in the same industry or you're totally, you know, switching.

Scott Anthony Barlow 07:00

It wasn't a dramatic moment at all. It was the cumulative weight of knowing that something had to change. So where then did Scott's career change take him after? I'm gonna let him tell you.

Scott Ingham 07:12

I kind of had to set my ego aside a little bit and reach out to people and, you know, ask them what they did, doing these, like informal interviews. And I felt like a little bit like, "Gosh, I've been in this industry, and I'm doing this, and I'm going to change now." And Phillip was like, "Who cares? Just, you know, get out there and get as much information." And after I did it one-two times, I started to do it like crazy. And people at the gym be like, "Hey, can I buy you a cup of coffee? And, you know, just kind of curious. I'm in the middle of looking, you know, a career transition, just kind of curious what you do." And people were, surprisingly, really willing to do that and take 5-10 minutes out of their time, whether it was a virtual coffee or a lot of people really were just like, "Yeah, let's meet up at, you know, Starbucks, and you know, we could talk at this time." And by letting people know and talking to people about what I was doing led me to where I'm at now, because it was someone were that knew someone that was hiring for this role. It's still in the medical industry. It's just a totally different therapeutic area, and a lot smaller company, a lot less red tape, and people know you. And so, I was basically just doing it, you know, an interview, and just kind of practicing and just kind of get to know the company a little bit, and know the position, and one interview led to the next, then led to the next. And, you know, I was texting Phillip along the way, I was like, "This is getting more serious as we go on." And I think my ability to just be curious about the position led me to, and obviously my skill set that, you know, sometimes I feel like doesn't, you know, have a lot of weight, had a lot of weight with this particular spot. And so I was awarded this spot where, you know, there was people with many, many, many more years of experience than what I had to give them in this certain area that didn't get awarded the position. I think what it was is, you know, in one of the exercises, I don't remember which one it was, so I apologize, but we're writing down exactly what I want, almost like the... it was like the ideal career day. There was bits and pieces that came out of that. And I think they were kind of shocked that, you know, this is what I'm looking for, and not like I was this person begging for the job or answering all the questions the way that they wanted. I had... I was just like, "This is what I'm looking for in a position, in a company, in a company culture." And I honestly think that was what sealed it for me.

Scott Anthony Barlow 10:43

Okay, let's look at Scott's strategic shift within healthcare sales, and how that compares to Carolyn's experience. After 35 years as a mechanical engineer, she was ready to leave engineering entirely. She had also eventually, along the way, moved into engineering leadership. But this most recent set of experiences had her burned out completely, and she was considering much more of an absolute, complete break than what Scott was considering. But her story took an unexpected turn. Here she is talking about questioning herself during her change.

Carolyn 11:20

I was doubting everything about myself. I failed in that role. I believed that was going to be a great opportunity for me, and that I was going to be able to make all these changes and implement stuff that I really believed in, that I felt strongly in, and I failed. And so what am I doing? There's definitely something wrong here, and what can I do going forward? Because it's not this is how I felt. I really did believe that it was me, you know, that it wasn't the wrong fit or anything like that. I thought it was just me not being capable of doing this job.

Scott Anthony Barlow 12:03

Carolyn's burnout in a leadership role had convinced her that she needed to abandon engineering completely. By the way, this is the norm. Often, when we are burnt out by something or been in it for a long time, we think we have to just throw it all out and start over. And it's usually not the right decision. She was so done with her field, though, that she couldn't imagine even staying in it. But through the process of examining what had worked in the past, what she loved–her strengths– she made a crucial discovery.

Carolyn 12:35

Analyzing what my strengths are, you know, going through the exercise and filling out, I think I did multiple different assessments to determine what my strengths are, and understanding what those are made me realize, "Okay, I was not in the wrong field after all. Engineering actually does." I know! It really does. And there were times in my career so I reflected, because you basically write down all of your jobs, and what was it about that job that energized you and that exercise really brought it home for me, that, you know, there were times in my career that I absolutely loved what I was doing, and I was energized by the type of work it was and it was satisfying.

Scott Anthony Barlow 13:23

Yes, of course, you learned that the problem wasn't engineering. It was actually the management pieces. She didn't enjoy that. More specifically, it was being in a role that took her away from her strengths and all the parts and pieces of engineering that did energize her. This realization led to a very specific distinction for Carolyn, and many people miss this.

Carolyn 13:23

I like to mentor people, not the same as managing people.

Scott Anthony Barlow 13:34

Two different activities. Potentially, completely, they can overlap, but they don't need to.

Carolyn 13:56

And they were overlapping, but I didn't realize that it was mentoring that actually brought me some happiness. You know, passing on this knowledge to the younger or less experienced engineers was something that really did give me a sense of happiness, or, you know, joy, whatever you want to call it, and I've gotten compliments from the people that I have mentored that, you know, I was very effective for them. I taught them a lot. They learned a lot from me. It was something that definitely we both got something out of. But once I stepped into straight up management, that's not what I was doing. So it gave me some perspective on what are the things that really would make me happy in a job.

Scott Anthony Barlow 14:53

This distinction between mentoring and managing became the key to Carolyn's solution. Your solution is gonna be different, by the way. But in her case, she didn't need to leave engineering. She needed to find an engineering role that emphasized mentoring and hands on technical work, rather than traditional management. And this led her to her current position, which listened to how she describes this.

Carolyn 15:18

I absolutely love the team I'm working on. I'm not the leader of the team. There's someone else who's worked there for a long time and kind of worked his way up from the bottom. He really has a lot of people skills, and I enjoy working with him, and he leads us, but he's not like my manager, so we have this great rapport, I guess. And there's one other person. We're a very small group. So three engineers or three people in the engineering group, I'm the only degree engineer, but that's not what matters to me. They have their own strengths that they bring to it.

Scott Anthony Barlow 15:54

So, yes, Carolyn stayed in engineering, but everything about how she works changed. She found a small team environment with a collaborative leadership where she could focus on the technical work and the mentoring, without the traditional management responsibilities or those things that she didn't really want. She even has a four day work week now, which is something that energizes her even more. Let's look at Bob Kalish's approach. The portfolio career. After 24 years as a restaurant chef, Bob didn't make one dramatic change. Instead, he began experimenting with building multiple streams of opportunity. Here's what he had to say about making a change after 50 years old.

Bob Kalish 16:36

Every second counts, right? And if you pause for a second, guess what, that's counted. Right? And, you know, it's a combination of that. And when you look at a timeline of your career, let alone your life, but let's just say your career, what do you want to do with, you know, as I'm reaching my, you know, into my 50s now, what did I want to do, right, with the last 10 years? What do I want to do next? What's going to fulfill me? And it just kind of keeps building momentum and building momentum. I'm not looking for my legacy part of my career, but that's what I find myself in, not about me, but can I leave it better than what I got? Right? And for the most part, I would say, we're going to try and hopefully we can influence one or two people. And I think that would be a win. One or two people. If everybody could influence one or two people in a way to make it better, you're winning. And, you know, one of my biggest, you know, influence in my life is my wife, and I remember her saying to me at one point, hey, you know, and this was when we're in our 40s, like, she said, "Hey, you know, let's think about where we want to retire to." And I was tired, and, you know, that's so far away, right? And I was... So the response I gave, "I don't know. What do you think of? The mountains? The beach?" And she goes, "No. What country?" And I was like, "Oh my god, I'm gonna have to think about thiss" But, you know, she's that person in my life that, you know, makes me think of the bigger picture. So, you know, that's... I've always looked at my life as kind of a timeline that you don't know when it ends, right? So you've got to, you know, I know at some point I want to retire. At some point. You know, when I first came on, my goal was simple, Scott. When I first came on and signed on, I wanted to just get that last patch of my career to retirement. If I had to drag it across the line on my back, that's what I was going to do. And one of your coaches changed my mindset so quick. And she said, "Well, what if you were doing the things you love to do with the people you love doing it with? Why would you want to retire?" And I was like, "Oh, boy, much like my wife, saying, 'what country?'" I felt like, you know what, I probably wouldn't want to retire if I was having fun with the people I wanted to have fun with, doing the things I wanted to do. So all of a sudden my mind started opening up again.

Scott Anthony Barlow 19:34

This is a completely different approach, and what we might call the portfolio career. Rather than making one dramatic pivot, Bob began experimenting with many ways, multiple ways, to apply his restaurant expertise. And this experimentation mindset led him to explore how consulting could allow him to contribute his knowledge while working in an entirely new way.

Bob Kalish 19:55

And working with Megan a ton on this stuff of just sifting through, "What about this? What about that?" Kind of conversations and throwing breadcrumbs down, right? And me picking them up and running with the ball. I got to a point where that giving back piece was super important to me. I looked at things... I have life experiences. I have work experience. And how do I give them back in a way that's different than what I was doing? Okay? How can I help organizations? How can I help people? And consulting came up, and I was like, "You know, that might be a great opportunity for me to look at things in a different light."

Scott Anthony Barlow 20:57

Bob's approach involved extensive experimentation, what we call career experiments. He started having conversations with people across the restaurant and food industry. And during these conversations, Bob's goal was to get a feel for how a consulting chef worked, and if it seemed like something that would make him happy, if it would fill him up or fit his strengths or align with those parts and pieces that he knew he wanted in this next step.

Bob Kalish 21:23

As you go through the process, you just start trying to think of everything possible that you could possibly do and then scratch them off the list. Right? And for one reason or another, by doing that, you start... the career starts rising to the top, and getting rid of the "no's" to get to the "yes" is kind of the mentality behind it. And working with Megan a ton on this stuff of just sifting through, "What about this? What about that?" Kind of conversations and throwing breadcrumbs down, right? And me picking them up and running with the ball. I got to a point where that giving back piece was super important to me. I looked at things. I have life experiences. I have work experience. And how do I give them back in a way that's different than what I was doing? Okay? How can I help organizations? How can I help people? And consulting came up, and I was like, "You know, that might be a great opportunity for me to look at things in a different light." I think what I liked about it was not being emotionally attached to one thing for too long. And, you know, go in there, get the job done, move on to the next thing. There's a certain freedom about that in my mind that I enjoyed. I thought if, while I was consulting, I could make a positive influence in the dynamics in a kitchen if I could get the conversation going, which I previously mentioned, maybe I wasn't as good of a communicator as I needed to be an advocate for myself, if you will. If I could remove frustrations from the team, then maybe, you know, that might be something that would actually fulfill me. And, you know, one case at a time, you know, one job at a time. And so I kicked around the idea quite a bit, and it rides right alongside the coaching piece, right? They're kind of hand in hand, the way I see, the way I envision it.

Scott Anthony Barlow 24:03

Okay, so here's the key insight from Bob's experience. Career change after 50 doesn't have to mean picking one path and hoping it works. It actually doesn't have to mean anything that you think it means. Often you can experiment, you can build multiple relationships, you could create a portfolio of opportunities that all leverage your existing experience in different ways, or you can do something else that fits. But here's what all three of these stories have in common. They required confronting the unique challenges of career change after 50. Scott faced the time management challenge that many people with decades of experience face.

Bob Kalish 24:40

For me it was, I'll be honest, was the time management of it. Because I was working quite a few hours at work, obviously, you know, family obligations. So I had, I sat down with Phillip, and we did this schedule. I thought I had to spend these huge blocks of time in order to get stuff done, versus getting up, you know, a half hour early in the morning and, you know, doing 45 minutes before I went to work, and then squeezing time in the evening time and doing 45 minutes to end, versus, "Oh, I need to, you know, spend two and a half hours every day at night."

Scott Anthony Barlow 25:26

Okay, this is crucial. You don't need massive blocks of time to work on your career change. When you're in your 50s, chances are high that you're busy or you're involved with a number of different things. You built an entire life, and you've got things to do. But luckily, small, consistent efforts compound over time. Scott also had to get his family on board.

Scott Ingham 25:48

I mean, my wife and I sat down each week together that we had a specified time that we sat down and I basically shared with her what I needed to do. I mean, she was part of this process so she knew each step of the way, but each week I would show her be like, "I need to get this done. It's going to take approximately this amount of time." And we would basically plan out our schedule for the week.

Scott Anthony Barlow 26:12

These weekly planning sessions with his spouse ensured that career change didn't become a source of family stress, but rather a shared project. This level of intentional communication is often what separates successful career change from those who get stuck along the way. Now, maybe the most important insight for anyone considering a career change after 50 comes from what Carolyn discovered. Many people believe they need to completely change fields, then what they actually need is to simply shift how they work within their field, really figuring out what an ideal role means for you. Carolyn puts it perfectly.

Carolyn 26:52

I found getting back to actual engineering was what I wanted to do. So re-centering myself in engineering and not necessarily the leadership side of it, and that's what I did. So that I could really leverage the strengths that I have that, you know, historically, had brought me happiness. So, and that is okay to step back. You don't have to just keep advancing and going on that career ladder that's basically pushing you into something that maybe you never really wanted.

Scott Anthony Barlow 27:25

In a culture obsessed with climbing the ladder, it's easy to get stuck on that same ladder, but sometimes the best career move is a lateral shift or even a step back. What really actually matters is not what direction you're moving. What matters is, does what you're moving to align better with the life that you're trying to build– your strengths, your interests and what you value the most. All three of our guests had to overcome what I call, the skills transfer myth. And that's the belief that your skills, your experiences, from one industry or occupation or company, it just won't transfer elsewhere. Scott discovered, of course, that this wasn't true.

Scott Ingham 28:06

I loved hearing those affirmations from Phillip, and that slowly helped me change my mind. And there was different modules through the course, too, that you know, where you write out your skill sets. And I thought, "Wait a second. These skills can be transferred anywhere."

Scott Anthony Barlow 28:28

It's crazy.

Scott Ingham 28:29

It's absolutely crazy. I'm like, "I thought I was, like, a one trick pony." I'm like, "I have a lot of skills that could be utilized", you know, with a finance background and in a sales background and in help building sales teams, I was like, "I could do a lot of different things that were out there."

Scott Anthony Barlow 28:49

As you might have guessed, this realization opened up possibilities that Scott never knew existed. The truth is, most of your skills are transferable. Usually, whatever percentage of your skills that you think are transferable is much, much higher than what you think. That's the consistent theme I've seen. You just need to reframe how you're thinking about them and maybe even get help presenting them a different way. So how do you decide whether to make a complete career change or find ways to shift within your current field or industry? Here's a couple of questions to ask yourself. First, is it the work itself that's the problem, or is it the environment, the culture, or the way you're being asked to do the work? Carolyn thought she hated engineering when she actually hated the management pieces. Second, when you look back at your career, what moments energized you the most? Those moments usually contain clues about what elements to preserve and which ones to build upon. Third, there are aspects of your current expertise that you could apply in new ways or in different contexts. Bob took his restaurant experience and created consulting and those types of opportunities. And finally, what experiments can you run while you're still in your current role? That way, you can test out different possibilities. You don't have to quit your job to start exploring other alternatives. Now, the great thing about career change after 50 is that you have something younger career changers don't– deep expertise often established networks, financial stability that allows for more strategic, rather than desperate decision making. Your decades of experience aren't a limitation, they're a competitive advantage. And the question here isn't whether or not you can afford to make a change at this stage. The question is whether you can afford not to.

Scott Anthony Barlow 30:41

If you want help with this, it's what we do every single day. It's what we love to do. Just drop me an email, Scott@happentoyourcareer.com, put 'Conversation' in the subject line. I'll connect you with the right person on my team. They'll have a conversation with you, and we'll figure out the very best way that we can help. Again, that's Scott@happentoyourcareer.com.