Exploring Second Careers

Anita Brick: Hi, this is Anita Brick with CareerCast at Chicago Booth. Today we're delighted to be speaking with Libby Gill. Libby was a senior vice president at Universal Studios, a vice president at Sony Pictures Entertainment and Turner Broadcasting, and was also the PR and branding brain behind the launch of the Dr. Phil Show in 2000. Libby left the corporate world and founded Libby Gill & Company, which focuses on creating client success through powerful personal and business brands.

Libby is an internationally respected executive coach, employee engagement expert, and best-selling author. Her clients include Microsoft, Pfizer, the Boeing Company, PricewaterhouseCoopers, and many more. The list was just so long, Libby. I just had to cut it down because they want to hear from you, not from me. As I said, Libby is the best-selling author of Traveling Hopefully: How to Lose Your Baggage and Jumpstart Your Life.

She has shared her success strategies on the Today Show, the New York Times, the Wall Street Journal, and many, many other publications. Thank you for doing this. I know you're very busy and you have lots of things going on.

Libby Gill: Oh, my pleasure.

Anita Brick: So people talk about second careers. How would you define a second career?

Libby Gill: Well, it's funny, it's a little bit of a misnomer because a second career could be second, it could be fourth, it could be a side career. It's anything that you do as an adjunct to after or alongside what you consider your primary vocation. That could include a transition from the corporate world, as I did going from the corporate world to becoming an entrepreneur.

It also includes people back from the military who are leaving service and now going into some form of the business sector, whether that's for a corporation or on their own. It could be people who have been laid off and now have to find another career. Parents, either stay-at-home moms or stay-at-home dads who are going back into the workforce.

And of course, the most obvious, but not necessarily the biggest, group of all of them are the retirees. There's so many studies out about retirees who don't want to retire.

Anita Brick: Right.

Libby Gill: I think 75 percent of people say they'll never retire, and with good reason, since very few of us have the money saved for that. So all of those could be considered second careers or second acts, however you want to term it.

Anita Brick: When you think of the audience listening today, it could be someone who is in his or her 20s, having gone to business school and thinking about what to do next or—I actually got an email, because we were doing this career strategy workshop for alumni, and the email came back from someone and he said, I'm 102. Will this still apply to me?

So I think there's a broad range. I don't know that a 102-year-old is listening to this, but I think it could be a whole lot of things. There's so much out there and so many possibilities. How does one get started, and how does one filter to come up with some manageable number of career paths?

Libby Gill: The first and the most obvious thing to look at is what do you really want to do? Not everybody—and certainly at age 102, very unlikely you're going to be president of the United States, or an astronaut or a professional ballerina or any of those kinds of things. And by the way, there's a healthy argument for avocation, which I also think is a sort of a lost art and a lost passion in this country in terms of career.

Look at what your heart is telling you. Do the mental and the sort of gut-level soul searching, find out what you're good at. That's the first step. And that was something we didn't really mention about people with second careers, people who have a passion to do something else. And either they know what that else is, or they just know they're not satisfied doing what they're doing any longer.

I mean, sometimes you hit age 40 or 50 and think, wow, I've been doing this for the past 20 or 25 years. It's time to either do something that I feel is of greater service or greater meaning to me, or more creative, or has less people involved. That's the first step. What do you want to do? What kind of environment do you want to be in?

What kind of skills and passions can you tap into? What are you good at? And then of course, we're talking business. So what is the marketplace out there? What's the outlook for all of those things? It's a lot to think about.

Anita Brick: I think it's true. And one of the Evening MBA students asked a question, and I think it fits in quite well here: “I have worked in the field for the past six years, only to find that the future possibilities are disappearing. I now find myself unsure regarding my career path. What types of strategies or thought processes would you recommend to someone in my situation regarding research or finding attractive new career opportunities?”

Someone who maybe is feeling a little defeated because pursued his passion and now the avenues have dried up.

Libby Gill: This will sound sort of counterintuitive, but there's a little bit of a mourning process in here, and that's OK. You've got to acknowledge that you spent a lot of years, a lot of time and energy, possibly a lot of money going into this career. And the opportunities aren't where you thought they were. Forgive yourself for making a mistake or however you're viewing that.

And you now have that moment of, gee, that didn't work out, mourn it and then get ready to move on. My guess is, you know, some careers dry up overnight, whether they're technology based and something goes away or something new is replaced. All kinds of careers will come and go. But what you're good at, what your strengths are, what your … information, some of the technical information, may not be relevant in another career, but what you've learned and experienced as a professional is often transferable to another industry.

And I think people are very quick to assume that, gee, I'm working in healthcare, therefore I'm stuck in healthcare. My skills are very specific and I don't know where else I can take them. And particularly if you're coming from that place of feeling defeated or kind of kicking yourself a little bit for having made a mistake, you know, join the club.

There are many people who have gotten off the career path or made a detour somewhere, or just picked the wrong field, even if the field is still there. But they feel like, why did I choose that for myself? I mean, think about it. When you're maybe in your first or second year of college, picking a major seems monumental, and then many people just a couple of years after that, pick a career.

So picking one that's gone away or one that you have no passion for—that I hear actually more often than an industry that's gone away, but it's the same thing, so it's no longer a fit. So pick yourself up and let's get out there and find out what is.

Anita Brick: So I know you said that there are characteristics and skills and general experiences that are transferable in a tight market, which we find ourselves in right now. Employers are looking for perfection. How do you take those transferable skills that you see are transferable and really create a compelling message to help the employer take that kind of risk?

Libby Gill: That is an art. And you're right, it's an employer's market … marketplace right now. And it's much harder for the people out there looking for work, particularly in certain industries like the automotive industry, where people have been laid off in such vast numbers, they're all flooding the marketplace. What you need to do is open up your scope and look at your background in a much broader way than you've done before.

And I'll give you an example. I worked with a woman as a coach who was an engineer. She was a construction engineer, but she was a project manager, is what she really was. She didn't deal with the construction of the hospitals and those sorts of things that her company did. She managed ongoing projects. Looking at that, she assumed she was locked into a career in the construction industry for the rest of her life.

And again, it was one of those people who thought, you know, if I had it to do over again, I never would have picked this industry. Someone who was much more interested in pop culture and entertainment and the media. And she looked at that project management side of her career and her background, and was able to make a case for the fact that she understood strategy.

She understood working across divisions, different business units. She understood numbers, and she got a job in business development within a media corporation.

Anita Brick: Well, how did she convince them? It's a really different cultural environment. I mean, initially.

Libby Gill: Here's— the first sale is to you. So your fellow who wrote in, the first thing he's got to do after he's let go and had his, you know, cry and his beer or whatever he needs to do to understand that, OK, that door may have been closed. And also I would challenge that. I wonder if it's quite as closed as he thinks it is.

So that's one thing. Just to leave that on the table. Look at your background, whatever he worked in and he didn't say that. But were you in marketing and communications? Are you a great writer? Are you a strategist? Are you a financial person? Because there are those elements of business in virtually every industry. And look at what you've done.

If you target an industry, what are the current trends in that industry? Is it growing? I worked with a fellow also who was in contract government defense work, and it was installing computer systems, but on a Pentagon level. I mean, it was huge systems. And looking around for other businesses, what he did in the sort of overall strategic IT systems for companies was, at some scale, in almost every business.

So he began to look at businesses that were moving into his area in the Pacific Northwest—which were growing, which companies were leasing more office space, all of those things to get a sense of who was thriving, who was growing. And then the first sale, as I said, was to himself: yes, I can work outside of this narrow sort of business I've been in.

Where else might they need my management skills? And he had a lot of skills specific to finance and began just broadening out, talking to people, targeting a couple of industries. And that's an easy way to start for people who are trying to make a segue into another industry. It would be nice if you could open the door to all of them, but that can be very overwhelming.

So if you think from—this fellow who wrote in, for example, if he's a marketing or whatever sales person in his industry and his industry's going away, take those skills. Look at whether it's healthcare, technology, communications, some other type of industry and see where his fit might be. Then you really need to begin to learn whatever you can about that industry, from who the major players are, what the jargon and the languages, what the buzzwords are, what kinds of people they're hiring.

And then, you know, then there's a whole process of networking and getting to know people. And—but you've got to start on a fairly small scale. And ideally, if you can stay at your job while you're doing this, that can give you the time and the money, the resources, kind of a foundation to launch that second career, that's absolutely the best way to do it.

It's like, go get a job while you've got a job, but this is much bigger. It may take a year to figure out what your next move is. So if anybody's in an industry like this fellow and thinks there won't be the opportunity in 10 years or a year or a couple decades from now, begin to branch out and see where else you might fit. That make sense?

Anita Brick: Yeah. Oh, it absolutely makes sense. And I think you're right. You have to sell yourself first because you'll never sell anybody else if you don't. What if you're in between jobs right now and you're feeling a little bit desperate? How do you still convey that confidence without really showing that desperation?

Libby Gill: It's a funny time we live in, for sure, and I really think this is a time—not to sound too California woo woo, even though that's where I am, in California—but you really need to get down to whatever is your best source of strength, whether that is your family, whether that is your faith, your working out, taking care of yourself, your health.

It's not time to allow yourself the luxury of falling apart because most of us can't afford that. If you're an entrepreneur, boy, you've got to really hustle and get much smarter about how you build and grow your business, how you retain the customers you have. And if you're in the corporate world or in between jobs, that can be so ego deflating.

Everything tells us it's the loser mentality. Because in this country particularly, we weigh our worth and we get our validation so much from the workplace, which is not like that in other parts of the world. You're who you are and what you do is what you do. You have to find ways to get around that with whatever is meaningful to you, whatever you value in your life, go back to that.

Well, you know, it's time to fill up on that kind of energy from your friends, family, people who believe in you and care about you. Get out a great book if that inspires you, get back to some sort of a religious or spiritual community. Start working out. I know, boy, I've got my workouts every single day just to feel like … I’ve got to stay healthy and in shape because this is a tough time.

So that's the first thing. Get yourself back on track and feeling good and not taking any of this personally because, you know, pick up today's paper, pick up any paper for the last two months or probably the foreseeable future. And there are many people in the same position. So toughen up, because there's no other easy way around all of this.

Anita Brick: Good point. And getting back to the same person or anyone who's contemplating a second career because of the reduced robustness of their current profession. What are some things that you advise people to do to assess the risks and viability of this new career?

Libby Gill: I like “reduced robustness,” by the way. It’s a fabulous sort of euphemism, and I like it. That's great. But that's very apt for many professions. Well, first of all, you've got to start doing your homework. You've got to really do the research. There's so many things available online from salary.com that tells you, you know, what people are making in different professions.

There are forecasting tools you need to Google that profession. You need to Google the long-range prognosis for these different industries, first of all, so that you have a basic idea of what the future holds in an industry that you're targeting. So get yourself educated enough with tools, books, online—you know, hit your local bookstore or library, or get online and really get yourself educated.

That's never been easier than it has been before. I mean, right now you can really learn a lot without setting foot outside. So do that and then begin talking to people. Then you begin to network with professionals. If you're looking at something where you want to go into a whole new direction, it may be time to get back to school, get some advanced training, another degree.

It may just be a simple class or two or a certification that you need. If you need to do that, get that started now. As soon as you begin to get that feeling—wow, reduced robustness has set in in my field, it's time to do some homework. Once you feel like you can communicate at a professional level with people in this other field, then get out there amongst them.

Start making phone calls, join professional organizations. I knew a fellow who wanted to be in a fairly obscure segment of the pharmaceutical world. He went—It was kind of a lofty research area and he didn't really know anything about that profession, and went to a conference and everybody's explaining what they do. And it was fairly complicated and esoteric, and he was the only person in the room not connected to that field, and at first was scared to death to kind of admit it, but then found out he became the object of everybody's attention because they were fascinated that he had made this wild left turn and that he was interested in their profession.

So people stepped up to help him and give him phone numbers, business cards, leads. So that's what you've got to do. And sometimes being the new kid on the block can be an advantage, as it was for him. But certainly you've got to put yourself out there where you can talk to people, set up those one-on-one informational interviews, and you've got to do that again.

It goes back to that sort of ego-deflating feeling of, gee, why should this person take my phone call? They don't know me from Adam. But as you network, it just becomes the snowball going downhill as you start to pick up that momentum. and you find one person who knows three people, and that person knows three more people.

And you really have to make that a career before you find that second career.

Anita Brick: To your point, one of the things that you can do, because one of the students asked, well, how do you really draw honest parallels between your past and where you want to go in the future? And I think that's exactly how you do it. I mean, you pay attention, you take notes, you engage with people. They can actually help you fill in the gaps.

Libby Gill: And it's not as hard as people think. I mean, if you are one human being, you were drawn to a profession for whatever reason. Now you're drawn to another. You're still the same person, and there is a way to simplify and articulate that message. And when I work with all my folks, my mantra is clarify, simplify, and execute.

So once you've clarified where that vision is, then you simplify the message so other people can get it, and then you execute your plan. You get out there and do the hard work and there's no magic formula for it. But there is some logic. When I left the entertainment world and, you know, my background was I worked in the television business for 20 years and became an executive coach, working with companies, working with individuals.

It was all about career excellence and how you could really find what you could bring to the workplace. I mean, for some people, that's kind of a— To me, it made eminent sense, and all I had to do was explain to people that the most significant part of my past career in entertainment—I liked working with the media, the strategy, all of that was great, and the perks and the pay and the comfort and security of a real job. That was great, a corporate job.

But for me, the real joy was in mentoring and tutoring my young staff—because I always had a bunch of young people, different generations—helping guide those people to professions of choice that they were passionate about, that they could succeed in.

And to me, that's what I took with me to coaching. So to me, that's kind of a no-brainer. It's not even a huge stretch, and presented that way, people get it immediately. So it's how to find those elements of your past career that create a throughline to your new career, and you get to try it out.

You get to work this language, this is your personal brand language, and you've got to work it and try it out on colleagues, family members, people close to you, your inner circle of people that you trust, and get some good feedback from them. And if you get a big “I don't know what you're talking about” and you get recurring themes like that, it requires a little bit more work and homework.

Anita Brick: I agree with you, because I think sometimes people say, well, I have my message and they just don't get it and they don't get it. You need to keep refining it so that you can engage. And I think if you do, like you said, people will still ask you questions that allow you to refine it to the point where, OK, I get it. When you went from “here's where I was” and then “here's my message as an executive coach,” it's very, very clear, right?

Libby Gill: And of course, I could easily muddy that up very quickly if I threw in all the other things that I do. I choose not to, because if I said, oh, when I do this podcast and I write these books and I do this …. no need to dilute it, you need to find out what that core message is. And like you said, they have to get it.

A message is two parts. It's what you say and what they hear. And if those two don't meet up, then you don't have your message. It's back to the drawing board to really work on that, because it is purely perception. They've got to hear what you think you're putting out. And I'm forever sending people out to go talk to five people in your inner circle.

And this is sometimes in personal life because what people do in their personal life always carries over into their profession. But go ask five of your trusted colleagues for some feedback, and ask them for three to five adjectives on how they would describe you to someone in the business world who doesn't know you. This doesn't give them a whole lot of room to editorialize, and it also doesn't allow you to lead them.

If five people are giving you three to five adjectives of how they would describe you, see where the common ground is. Are they all describing you in the same way? Are they all perceiving you completely differently? What are the strengths? What are the weaknesses? You begin to get a picture outside yourself, because we all have blind spots and it can be a great exercise.

It never ceases to amaze me how sometimes very intelligent and successful people can be incredibly unaware. And you need some objectivity to be able to craft that message so people who don't have a clue who you are can really get it.

Anita Brick: I like that, I think it's very simple what you're suggesting, and yet if you listen and you write it all down, because sometimes we get messages, adjectives that we don't necessarily like.

Libby Gill: Yeah. So we ignore those.

Anita Brick: So we go, OK, well they're wrong. If you write it down and put it away and then go back to it, I think that's a great idea because it's very simple. And you're asking people for just a small bit of their time.

Libby Gill: Exactly. And it's really simple. And if somebody cares about you even just a little bit, they'd be happy to do that. Most people can do it off the cuff. And I usually have people explain what they're doing: “I'm rebranding myself. I'm really trying to figure out how to present myself in this new situation, and I'd like a little insight.”

I just did this on a course that I lead, and there was one woman who's a realtor who was convinced—you know, realtors are, to the outside world, they're all the same. You're a realtor, you provide a service. And I said, not necessarily, because if what you do—and that's the challenge—if what you do is similar or seemingly identical to someone else, you've got to find that point of differentiation.

So she went out, she did her homework, she asked her five people and came back with a lot. I can't remember her exact words, but they all had to do with how she got to know her clients, her customers on a very personal level and was therefore able to meet their needs. So it was that she's the one who picked up the phone, not a colleague.

She got to know them really well, understood a lot about their family dynamics and what they were looking for, and that came through. Sometimes the language was identical and sometimes it was a little off, but it was very clear it was that personal hands-on touch that set her apart.

Anita Brick: One of the Evening students asked, and I'm just curious if you've had any experience with this. He or she asked, do you have to go into an entry-level position if it's your second career? And if not, how do you manage otherwise?

Libby Gill: That's a great question point. There was no way at 45 I was going into an entry-level position. I couldn't afford it, and many people can't. Now, I don't know how old the student is, but no: if you've been working for any length of time and have some professional skills, it is this process of transferring them. I would absolutely avoid going into an entry-level position, because that makes a statement about you and your understanding of your own value and worth in the marketplace.

Now, if you're a youngster, if you're in your 20s and you've had a short-term …. you spent a couple of years in the workplace, you may go into an entry-level position in another firm, but you can also, even then, make it known that you're one of those responsible on the fast track. Not that “I want your job in six months” kind of mentality that so many boomers complain that the Gen Yers come with.

I don't always find that to be true. It's an understanding of, I know my worth and my value. I also recognize that I am starting over to some degree in this area. Here's what I bring to the table, and maybe you find a way to meet in the middle. You find a way to kind of get that interim step so you're not at an entry level.

Certainly if you're starting your own business, you're not … You're everything. You're from entry level to CEO.

Anita Brick: What if someone is looking for very specific experience? Is there a way to convince them or to really mitigate the risk and say, I don't have this exact experience? Here are the things that I think are highly transferable, and here's why I think you should, you know, make the choice with me. Because even though I may be a little more risky …

Libby Gill: I think smart companies—actually, Southwest is famous for their motto “Hire for attitude, train for skill.” And they have famously hired people—and a number of companies do the same—for people that they think are the right fit with their culture, and they are willing to train them. And that's the case you make. And you date those success stories, and people have to get pretty bold about being able to self-promote.

And there is that fine line of self-promotion and arrogance, and you must practice and find that line. Most people fall under that and don't tell the good success stories about themselves that they need to. So the first step in any interviewing process, you need to do a lot more listening than you do talking. Then it shifts to you talking.

But I think you can make the case for that: that it is about the fit for the company, the attitude, whatever their core values are, and how you can pick up the technical skills and the specialized knowledge; that that for you is the easiest part of the equation because you understand what their mission is, you understand how they deliver it.

I just interviewed Tony Hsieh, who's the CEO of Zappos.com, the online shoe company, which will hit a billion … it will be a billion-dollar company after … before I think they hit their decade mark. So amazing growth. They actually pay people not to take a job there, which I found fascinating. They will take somebody through their … either a one- or two-month training period, and they pay them for that training period.

They put them through all the training. And if they find at the end of that training period that they think the person is not the right fit, I think they reimburse them their costs or something. But it comes … it's in the low thousands, but they'll pay them, you know, significant—it's not $100, but it's a couple thousand dollars to leave.

If they've decided that it's not a good fit, they'll compensate them for their time and send them on their way. Because they feel so strongly that culture is the first, that's the primary job. Selling shoes, selling anything is not the primary job. It's creating the right culture so the right people can thrive. If you're on the other side of that, first, seeking out companies with that attitude is critical.

Anita Brick: Yeah. How do you find them? How do you find those kinds of companies?

Libby Gill: There are some benchmarks, like the Forbes list and the 100 Best Companies to Work For. And Working Mother has one for women. You go online and you search it. Although I got to tell you, I've talked to enough employees at those companies who say we don't know how we get on the list. I don’t see it.

Anita Brick: So there’s a PR factor.

Libby Gill: Yeah, exactly. Or, you know, you get on a list and you stay there. I'm not sure, but you need to get to know… You need your spies or your moles. You need to really get into some of those companies. And one way you can do this, if you're going in cold, which, of course, is the hardest way; the best way is to find a referral—but if you have to go in cold, study a company—and some people do this by region, if they've got kids in school or the spouse doesn't want to leave their area. So they look at where the growth market in the big companies are in there. You know, in a … maybe it's an hour radius of where they live.

And that at least narrows down your target for you. And you begin to look at some of those companies and then look at what you think are the points where you can provide something compelling. Find someone you can make a personal connection with. You've got nothing to lose by sending a letter to someone in a position that's a step above where you would want to be.

So if you want to be in the finance side or the marketing side, find that VP, find that senior someone in there. If you can establish a relationship, great. But it certainly doesn't hurt to write a letter saying, I've noticed this has been happening. I've talked to some of your customers in your market or I've known, I've heard, you know, what's out there through my professional organizations and networking.

Here's something I think I might be able to offer you. Now, all you're trying to do is get past the resume step. You're trying to get someone to say, hey, that's interesting. Never quite seen it put like this. This guy's smarter. This lady's got a lot to offer. Let's set up a phone call. And if your phone call turns into a meeting, great.

If they don't have a job opening, not a problem. You've made a connection. You may get them to send you elsewhere. It's trying all these things that you think, well, that's not the normal way you do it. You post a resume online or you call their HR department, and both of those things are fine, too. You know, desperate times call for desperate measures.

You need to try. And I'm not suggesting you act desperate, but that you really try some bold moves and get to know some people that are outside of your sphere, if that's what it takes.

Anita Brick: You know, at Chicago Booth, we have the online directory people can use and even within LinkedIn, which of course is a great social network. Some people like it, some people go—but I think all in all, people have had positive experiences. There's also a Chicago Booth group that you can join to expand things, but what if you are making a radical change?

There were two questions that came in, one from a Weekend student and one from an Executive MBA student. One person seems a little less radical. Someone was head of finance for the North American business unit. Heads up biz dev for the accounting practice of this firm and wants to go into private equity. The other person has been a banker and wants to move to a fast-moving consumer goods firm.

As a marketing manager or a brand manager, these are both pretty radical moves. What would you suggest that someone do when they're really not that much in the ballpark? It's competitive, and it's not a real obvious move.

Libby Gill: Well, clearly these are people who've been in the job market for a while, so they have a network. It is a matter of really leveraging your network. And there was an interesting thing, and I think it was in Malcolm Gladwell's book The Tipping Point, about the lore of close ties. People in your immediate circle generally know what you know.

They know what jobs are open, particularly if you're in the same field. They know what's happening andwho's moving from one company to another and where the ripple effect is. But you get a tier or two outside that, and you open yourself up to people who know things that you don't know, who have connections that you don't have.

So it's almost a “six degrees of separation.” So begin to use the connections you have to get outside your own circle. The finance person who's in the business development world, OK, now this is somebody who's in accounting, who's in finance—must know someone who knows someone at a private equity firm.

Anita Brick: Sure.

Libby Gill: And I can't imagine that they wouldn't. So that's when you begin to tell everybody, you know, and you have to test this out—if you're trying, if you're testing the waters while you're still employed, there's that fine line where you begin to make it known and OK, and obviously the first conversation is with your immediate supervisor. If you're going to look outside the company, whether you're doing this underground and this is a covert mission or whether you clue in your company, you know, there are all kinds of pitfalls to either suggestion.

But generally, I think people are very safe to do their homework, to start talking outside their company unless they're under some sort of contractual obligation not to talk or look elsewhere. And of course, that becomes a legal issue besides just an ethical issue. But if they're OK to look around—and I get this question all the time—how do I go look for a job without my boss finding out?

You know, because we're in a small world, there's one good answer. And believe me, your boss already knows the answer. And that's always looking at my options down the road, always wondering what I'm going to do in five or 10 years or 15 years from now. I'm always curious about how other people … what their paths to success are. That's one answer, and there's nothing wrong with that.

The other thing is to bring your boss into your confidence. If you're in the kind of relationship where that person is going to help you—and often that's the case even in, you know, great big companies—If you've made it clear, “I want to make the segue within the company” and that's not going to happen, then enlist your supervisors or put them on your team to help you go elsewhere, especially if it's a friendly, noncompetitive company. It's only … and often can be in their interest to have you go elsewhere.

So the first thing to do is leverage your connections by having been a professional to get in front of people based on a good, solid referral from someone. That person who will see you, they're not doing you a favor. They're doing the person they know a favor. So that's what you need to draw on. And then you begin.

Once you get in front of that person, you need to impress them with, of course, your courtesy and your smarts and your thoughtfulness and the fact that you've done your homework. And if they get—you know, here's a live wire here in front of me. Gee, I really want to help this person—people's better instincts often kick in.

I mean, I came from a pretty tough industry in the entertainment world, but there are plenty of good-hearted, generous folks out there. I spent an hour on the phone with a fellow in my profession, but years ahead of me, yesterday. I've never even met him face to face. Out of the goodness of his heart, he just gave me an hour of advice and training that, you know, I'm not sure I could have bought anywhere and was just happy to do it.

So it's really picking up the phone and doing those things. And when you mentioned LinkedIn and all the things that you have available at Booth, I wonder how many people take advantage of them. I’ll bet it's not 90 percent.

Anita Brick: I bet you're right.

Libby Gill: It would be great if it's 50 percent. It's shocking how many resources are available that people either just assume— “I know there's nothing there for me,” or they don't bother to put themselves in the front. You know, you’ve got to be at the front of the class, you've got to be the one who, without being obnoxious, says, well, I'm going to go to that event and I'm going to get to know some people that either teach in that field or have been in that field or whoever I need to know.

I mean, even LinkedIn, as you said, some people like it, some people don't. Even if you don't like it, there's no excuse not to have your resume on it.

Anita Brick: And it's a good point. And again, there is a plus/minus with being visible or being that visible. I know one thing that people can do at the school, whether they're an evening or a weekend or an Executive MBA student or an alum, they can post their resume confidentially on a resume database. And there—and to me, at that point, the confidentiality aspect is taken care of, and at the very least they can move ahead.

So even for this banker. He, he or she didn't really say this person was employed or not. The possibility of moving into brand or marketing management is a possibility, but it sounds like only if this person really digs down and finds out why. And sells him or herself first and then goes out, does the research, and keeps building on that so that there's a parallel … I mean, one obvious parallel, it depends what industry this person covered. If it was consumer goods, there's a parallel already there.

Libby Gill: And even within banking, even if they're in traditional banking, you can create that parallel for what you did as a banker, what portfolios you managed or what you did and why. That translates into being a brand manager. Do the homework for them. Make it readily apparent for the other people. Another good use of social networking, like LinkedIn and even Facebook and Twitter is you can ask questions, you can join groups, you can get on there and join a fast-moving consumer goods group, or a branding, or a brand manager or marketing group and find out you can build connections that way.

It’s odd how this has become …. in the last few years how it's taken off. I have watched how corporate executives, business owners have used those tools really successfully in fairly traditional fields. You don't have to be in the high-tech world. You don't have to be in some kind of snazzy entertainment or online marketing world to use those tools effectively.

It does take a little homework, but I use Twitter, I use Facebook, all those things that I never thought would be quite as relevant to my business. You know, if you're over, I don't know, 40 and you feel like Facebook is for kids, you may be surprised how many professionals are on those sites and a different kind of relationship.

I had … a friend convinced me that I needed to be on Facebook and I thought, OK, I'll give it a try. And I do a lot of public speaking. I found that all the big speakers bureaus that I work with were already there, and I got emails, you know, kind of friendly and funny on Facebook. And it established a different kind of relationship than I had with people, just because I know them through the phone or we've had business dealings in the past.

And I always do tell people it's a little bit like those kinds of social networking sites where people tend to be brief and sloppy and a little snappy and sometimes a little too cute. You have to be careful because it's like going out with your boss or a prospective employer or favorite client after work and going out for a drink, where it's OK to have one beer and be conversational. Don’t down a six pack and spill your guts. You have to be thoughtful.

Anita Brick: Very, very good point. Yeah, I just … a couple final questions if you have a few more minutes. One person, an alum, said, “I have more than 30 years of work experience, and I'm wondering if it's too late for me to have a second career in something that maybe I don't have a lot of experience in, but I have lots of interest.” And I guess that kind of goes along with the question, is there a right or wrong time to pursue a second career?

Libby Gill: I don't think there's ever a right or wrong time. I mean, having watched my father retire and see what a terrible mistake that was for someone who was vital and intelligent, I just think the old … the traditional retirement has just gone away.

The best time, of course, to pursue a second career is when you've got one and you've got a year's income under you, but that doesn't … it's not always the case. And if you can't do that, a great way, especially if you have 30 years of experience—so I'm assuming this person is 50 or more, right? Get into some sort of volunteering capacity. And for people who are out of work, take a very visible, some kind of leadership role in a professional organization. It may be the only time you've got time to do it, but it gets you in front of all kinds of colleagues.

Don't just join and show up. If you're really trying to establish a name, take on leadership so people see you in action. That's how you get hired. And even short-term consulting while you're looking for a next corporate position can be great. But that sort of breaks my heart for this person to think it's too late. It's absolutely … I don't think it's ever too late.

And in fact, AARP and Yahoo just did similar surveys asking people when they thought the best retirement age was or what age they'd be when they retired. And I think more than 70 percent in both surveys said never. Most people think that there is no such thing, so it's finding a way to translate that experience. Ideally, if this person can translate his or her experience in ways that we're talking about. And if not, do the math homework; find out if you can afford to take a pay cut to work in the nonprofit sector, to volunteer to start something on the side, look into all those things.

I would hope that life throws you so much more rich opportunities as you grow old. I mean, I've got my next few careers lined up. People laugh that I've got the next one after this, and then the one after that.

Anita Brick: Oh, you have to tell us. What are they?

Libby Gill: Well, I taught college for a year. I taught out here at Cal State Northridge and taught in the business and the media schools and taught for years, which is why I know firsthand all these kids—and I say kids because I'm in my 50s. And I said, you know, stay in touch. I would say less than 10 percent use me as a resource, even though I knew, you know, at that time, everybody in Hollywood, and these were all mostly people in television, film, media majors.

And so few took advantage of that—it was not surprising, but disheartening. I've written three—I'm on my third nonfiction book right now, which is apropos to what we're talking about. It's called Unstuck: Mastering the New Rules of Risk Taking. So it's very much all of this that we're talking about.

Anita Brick: When does it come out?

Libby Gill: Comes out in the fall.

Anita Brick: Well, you have to keep us posted.

Libby Gill: Oh, I will for sure. And it's all these gutsy moves people are making. And some of them are just little teeny incremental steps that they take that get them to the bold move. After that, I'm going to try my hand at fiction, and I think I would like to teach university again at some point. So it's really a passion.

It ties in all the communication and the, you know, getting up in the front of the room, being able to speak from your soapbox, being able to share ideas and help people plot a course to success. Because I'm just a big believer in shortcuts and taking advantage of the information that's at hand, and you provide so much to people. If they just did what's available to them right there in your business school, I'm guessing people could exponentially up the level of success or shortcut the whole process of looking for that second career.

Anita Brick: I think it could certainly help a great deal. And so, I mean, you mentioned success … a couple of things. At the very beginning of our conversation, you talked about avocation. And then I'd like to add on how do you measure success and how does avocation fit into that.

Libby Gill: That is the most personal. You're asking me a very personal question. That is the most personal question of all. And I think the first thing anybody has to ask themselves is how they will measure success. I just got off the phone with a client who I'm coaching, and this is a new small-business owner, and she's got a trade show next week.

And that was my first question: How will you measure your success at that show? For some people, it's in dollars and cents. For her, because she's new, it's in learning and networking. But what's the most important thing to you is it. And it changes with stages of life. I mean, sometimes it's pure and simple: to make money and to make a name for yourself.

And that's OK. Nothing wrong with that. It could be being able to have a career that gives back to your community or your family or even something broader for the world at large. It could be a balance of those things. It could be in an environment that you find creatively stimulating, exciting. It can be a mix. It could be a variety of all those things.

But you need to sit down and ask yourself those questions. I always put a lot of tools on my website that are self-assessments. I have people go through a 10-step, very simple. What's the most important to you? And I think that's what you begin to measure against. You've got to know, is it more important for you to be a leader?

Is it more important for you to be a team member? Is it important for you to be creative? Is it important for you to be strategic and financial? There are analytical people that are creative people. That's also the way you figure out what kind of team you need around you, because people tend to hire who they are and what you want is exactly the opposite, of course.

Anita Brick: So where does avocation fit in?

Libby Gill: Oh, avocation. How can people live without avocations? I see the burnout from so many different sectors of people who, you know, they've got to put in either their billable hours or they believe it's the facetime, that they've just got to be in their desk chair from, you know, it's not 9 to 5, it's 7 a.m. to midnight because they go home and they're on their BlackBerry or their laptops or whatever.

Anita Brick: Right?

Libby Gill: Avocations you put your stake in the ground and you say, no. I sing in the choir. I coach Little League. I do … whatever it is you do that makes you who you are. Play music. I'm an activist in my local community. I'm working on this. You decide how to fill it in and how to fit it in with your work and your community.

And I'm not a big advocate of hiding things. I mean, for me, I always felt like I had three or four other things going on the side. I was either, you know, writing a screenplay or taking a college course or doing something while I was working full time. And those were things that were not, not necessarily welcome in my old career where they felt they pretty much owned you 24/7.

And that wasn't for me any longer. And I think that was one of the reasons I wanted to be my own boss. But I think it's really important to create those richer—that kind of context where you've got a deeply layered life, where your relationships, your health, your spiritual life, the things that give you fun and pleasure and learning and growth—I think those all have to be factored in.

And I truly think they make you a better professional. You bring much more to the table when you can bring your cultural heritage, your ethnicity, where you came from geographically, your interests, your skills, all these special learning and knowledge that you have. It makes you a well-rounded and interesting person that has much more to share.

So I'm a big advocate of people saying, no, gotta go do this. And we're learning that lesson from the Gen Y, the millennials who are coming into the workplace because they're staggered at their parents and employers that they see working in service of these companies. And of course, there's no longer, you know, the 30 years and the gold watch.

And a lot of people are coming in and saying, look, I'm going to work, but I need to, you know, I need to knock off at four because the surf is good today. But I'll be back online at six and I'll stay until two if you need me. And you know, when they find the right employer that recognizes it's really about the results and not the hours in the chair, right?

Then it's a total win-win. And that's a lesson the boomers and a lot of the traditionalists, the older than the boomers, are beginning to learn. And I think it's a great lesson.

Anita Brick: And it sounds like those are all really important things to factor in as one pursues a second or third or fourth or 10th career.

Libby Gill: Exactly right.

Anita Brick: Thank you so much. This was really terrific.

Libby Gill: My pleasure.

Anita Brick: I know you referenced your website and there are lots of really good things there. So Libby's website is actually her name. It's www.LibbyGill.com. And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.