Reinventing Your Career and Life

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career. Today, we're delighted to be speaking with Steve Olsher. Steve is known as the world's foremost reinvention expert. He is the author of What Is Your What? Great book, by the way, Steve. Discover the one amazing thing that you were born to do.

He is an international keynote speaker, chairman and co-founder of liquor.com and an in-demand media guest who has appeared on CNN, Fox business and other national outlets. He has an undergraduate degree in speech communication and an MBA concentrating in real estate. Steve, thank you so much. I know you just made a cross-country move. We already missed you in Chicago, so thank you for making the time.

Steve Olsher: Absolutely. Thanks for having me on either.

Anita Brick: Wonderful. So people have different definitions of what career reinvention means. Tell us how you would define career reinvention.

Steve Olsher: I would define career reinvention in the same way that I would define personal reinvention. It's really just about getting back to the core, back to the essence of who you inherently are. It has nothing to do with changing who you are. It's really more of becoming who you are already born to be and reconnecting with that core. And from an employment standpoint, from a career standpoint, it's a function, then, of making sure that your vocation reflects how you're naturally wired to excel.

Anita Brick: Got it. There are some questions around that, and one in particular from an evening student. He said, I know you talk about different principles, guidelines that you speak about in your book. And this one student said, I have more than one moment of truth which you called. Is it pronounced yano?

Steve Olsher: So, yeah. No moment, because it's just a fancy name.

Anita Brick: Got it. Okay. No experience. I have no idea how to make sense of them for my reinvention. So if someone has some experiences that they feel were really moments of truth for them, how would you advise someone to go about organizing that information and then actually doing something with it?

Steve Olsher: First and foremost, I think people put way too much pressure on themselves to read into what happens in life and try to come up with answers and solutions, and it's really more about looking for clues. I strongly believe that if you look at what transpired during those moments, you begin to find clues. The idea behind the concept of, you know, is really just to stack up as many positive, you know, choices as you can so that you remain as best as you can in alignment with what it is that you truly love to do.

And really, what's in your DNA? I mean, what's already in your blueprint? What makes you unique from the other beings that walk this planet? Ultimately, when you look at the, you know, moments that you've been able to identify, I would just simply ask this person to look at the choices that they made and explore why they made the choices they did and where it led them.

Anita Brick: Okay, it sounds like and we don't have the person sitting here, so we don't know for sure. But it sounds like the person is. And I know Chicago Booth, we are all about algorithms and formulas and frameworks, and there may be a little bit of that behind this question. So when you think about it, are there some things that you should consider? Are there some steps to take to actually sort through things that were important to you and ultimately, I'm not asking you to do this, but ultimately map those on to some potential new career choices.

Steve Olsher: You know, when it comes to career reinvention or, you know, moments as it relates to your career, it's again the same process. It's just making a conscious choice about what to do when you're presented with an opportunity and to make sure that the choice that you make really aligns with who you inherently are.

Anita Brick: I think that sounds easier said than done. Let's get some specific questions that came from students that may help us put a little bit of context around this. So an executive MBA student said, what do I need to do to make a big directional change, such as a different role in a different industry, maybe even in a different country? After working for 20 years to have a successful career, to go back into an MBA program and like the blinders come off and I like, wow, I could do this, I could do that. How do you start making a directional change when you already have 20 years of work experience in one direction?

Steve Olsher: Yeah, absolutely. And it's not the answer that they want to hear and the answer that they want to hear, that they can just jump into a position that reflects their 20 years of experience, to leverage those 20 years of experience in another industry against where you're going now and to say, hey, you know, I should be compensated those levels.

I should be in a certain position. Well, you probably don't have to start at ground zero, but you're probably going to start at floor number one. And that's something that you have to embrace as you look to reinvent who you are and reinvent your career. Because ultimately people don't reward you for what you've done. They reward you for what you're going to do and what you can do. So you got to prove yourself.

Anita Brick: How do you even get the attention of an employer? There was a weekend student who said, how do you convince a potential employer that you can excel in a job when you can't prove it on your resume?

Steve Olsher: There's a lot that goes into that, and I think ultimately what a person needs to think about is proving it without asking to be compensated. And I know that's a harsh way to look at this. You've got to prove that you have the ability to perform in the way that you know you can, but your employer, potential employer, they have no understanding of your ability to perform.

What I encourage people to do is to really think about having the opportunity to pay the bills, doing potentially what it is that they don't want to do, but it gets them from point A to point B in terms of their expenses and their overhead is concerned, and in the other hours do whatever they have to do to make sure that they can impress that potential employer, that they can build a name and a brand for themselves.

You know, we expect everyone else to potentially deliver us our future. It's not being proactive. Ultimately, I subscribe to and believe in the law of pro action, and that's really the only way that you're going to get to where you want to go fast, which is to be willing to sacrifice and be willing to do things that others, frankly, aren't.

Anita Brick: In practical terms, what does that mean? So what would that look to mean? Yeah, give me an example.

Steve Olsher: I would think about it from a consultant's type role. In other words, if you really want to work for a particular organization, go talk to that organization. Find out what their biggest problem is, find out what their biggest need is. Find out something specific that they have going on right now. That is a pain point for them and helps them solve it without compensation. That is the most practical advice that I can offer.

Anita Brick: To go along with something you said just a minute ago. You were talking about branding and how you need to build a brand and all of that. One of the existing MBA students, I think, agrees with you. And he said, Hi Steve, I have 15 years of work experience and want to reinvent myself. How do I enhance my visibility as a way to facilitate my career reinvention?

Steve Olsher: Great question. Social media is a double edged sword. I mean, it can either be like this endless black hole that just sucks in and you have no idea where you are or how you got there, but six hours later you're there. Or it can be something that you really use to your advantage. What I have found is that some of the folks out there that have landed positions that they absolutely love, or have landed consultancy roles, have done so by leveraging the power of social media to create that brand, to create a name for themselves.

And so what I would encourage anyone to do, insofar as branding and putting themselves out from a visibility standpoint, is, number one, get yourself a Facebook presence on a business page, not a personal page, but a business page. So something that reflects who you are from a business perspective. Same thing on Twitter, same thing on LinkedIn, same thing on the other social media sites that you choose to use.

And then I would start blogging. I would start writing on your subject immediately. Wherever you believe you have expertise, wherever you believe that you can add value to someone's equation. I would start blogging on that immediately. I would start shooting five six minute YouTube videos. Just talk about a particular problem and you provide the solution in 5 or 6 minutes.

Same thing with podcasting, just like we're doing now. If you can't get a guest to come on, no problem. Just pick a subject, start talking about it, rant and rave about it for ten, 12, 14 minutes and create an episode. But you gotta be proactive, and you have to get to the point where people now associate you with the particular problem that you solve and the expertise that you have.

Anita Brick: How do you balance that? If you are currently working for an employer, do you get their permission? Do you make sure you're not doing something in competition or too controversial? How do you mitigate that risk?

Steve Olsher: Reality is that if you're thinking about moving in a different career direction, then frankly, what your employer thinks now is irrelevant. Will you lose that job if they find out? No. Not necessarily. I mean, it's possible, but if you're performing at your position now and you're filling a need that they have, are they going to fire you because you're blogging on a different subject?

Maybe it's possible that they would. The reality is that if you're working for someone else and you begin building your own personal brand, if you are looking to leave the organization, then you really don't care and you just become polarizing. You do what you have to do anyway. If you're looking to enhance the organization, well, then of course you want to seek their approval.

What I have found is that a lot of organizations will support you in those efforts, because it benefits them. If you are a superstar and you work for Hewlett Packard, you are a superstar who works for Hewlett Packard, right? So it doesn't matter that it's your individual brand that gets the recognition. It's more about the fact that you are an individual brand.

And I'm using my fingers as quotes here who works for an organization. So ultimately you are going to be associated with that company, and your expertise is basically going to be credited to that company. So I know it's counterintuitive here, but you got to think about it two ways. Are you wanting to leave the organization or are you going to stay in the organization? And either way, you just get in the game.

Anita Brick: Understand the risk and take responsibility for those risks, because there is always a possibility that if you do something your company doesn't like, they could fire you.

Steve Olsher: And you have that risk anyway in what you do on a day to day basis.

Anita Brick: Got it. There were a few questions around challenges, and I think we've already sort of moved in that direction, a weekend student said. I've been working on a career change or as you would call it, a career reinvention into more senior roles. I have great initial conversations, but then things stop. How do I create a story that keeps me interested and gets the right type of positive attention for my reinvention? So it sounds like he or she is able to connect with people, but then once those connections are made, it sounds like it fizzles.

Steve Olsher: So there's two answers from an outside perspective. Here's what I can say. There's probably one of two things that's going on. Number one, either you're shooting too high and you know, I'm not saying that in a condescending way or I'm trying to be mean, but perhaps you're trying for a position that you're not truly qualified for.

That could be, of course, for a number of different reasons. So initially, on paper you look great. And maybe they're like, yeah, this is absolutely someone that we should come in and talk to. But ultimately when they compare apples to apples, which is you against another candidate, if that candidate has more experience, unfortunately you're going to lose that battle.

So perhaps you're shooting too high in terms of the position that you want to land. Now, I'm not saying that you wouldn't end up in that position, but you may have to start at a different level and work your way into that position. The second thing that I can offer is if you know that you can add benefit to an organization in a particular role, prove it.

And when I say prove it, what I mean is come up with case studies, work with people to solve problems that are similar to the role that you would have in that organization. Ultimately, you're doing the same work, but you're getting the results that are not reflective of doing it under the umbrella of that organization. You're doing it under your own name, under your own brand.

And what ends up happening, I have found, is that people who do that, if they take on the role and they do what it is that they believe they're going to be doing in that organization, and they start actually getting out there and take some risks and take some challenges and say, hey, organization, hey, this is something that I can help you with. They often don't go back to the organization where they wanted the job. They end up doing this as a consultant for their own business or for a different organization altogether, where they have an opportunity to work with more than one client.

Anita Brick: I like what you're saying, and I see people do that sometimes the way you're talking about it, sometimes they go into a nonprofit and help out, create a case study. More and more, though, I see people going to places where they can be an advisor, where they have strengths to early stage companies, to startups, to great ideas.

Steve Olsher: And so what ends up happening in that position? Yeah, they are able to demonstrate their expertise and add value to that organization. And oftentimes because the startup is really trying to figure out where they're going and what it is that they need. If you can prove that you have the solution to one of their problems, you may very well end up in a position in that startup because they're growing so fast. They need talent.

Anita Brick: Yeah, it certainly could be. And they would like to hire people where they trust them. And if you're there with them, yeah. And people have fun doing it too. I mean, not that we have tons of time to do all this stuff, but I've seen people do it very effectively, and sometimes they do end up inside the job.

I mean, inside the company. There is another question, another challenge from an alum who said, what are the first steps for someone who took off five years? I was in investment management for ten years, but they've been out for five years. I don't want to go back to 60 hours a week anymore. I know there are things I can do, but what are some initial steps to make my way back into the workplace?

Steve Olsher: That you probably know the answer that I'm going to give you to this question, which is you've got to do some self-exploration. You've got to grant yourself the time and permission to understand what it is that you truly want to do and how you're naturally wired to excel. So, of course, I would recommend that you do some introspection in terms of using the tools that are available to you.

Now that could be like my book, what is your what? It could be other tools like Strengthsfinder and, you know, Myers-Briggs, etc., etc. and you know, all of those tools are great. But, you know, I think that you're in a really fortunate position now, and I think most people who have had the opportunity to take some time off and now are looking to reenter the workplace, are in a really fortunate position because they can design their lives, they can design their careers.

They're not in a position where they, you know, they kind of sunk into all of these expenses where they have, you know, they have these obligations. Right? And so they have to keep a day job in order to meet those obligations. But when you're in a position where you're just getting back into the employment world, the workforce, the corporate world, whatever you want to call it, you can design your life.

And that's what I really encourage people to do, is design it, see it, make it happen. But if you can't see it, it's not going to happen. You're just going to end up basically living out the dreams and the agendas of others. You know, the reality is you're either living your own dream or you're fulfilling the dream of someone else.

Anita Brick: You're right. The other thing is today versus 5 or 10 years ago, there's a lot more flexibility in terms of designing it. It used to be you plugged into a slot and you just kept marching along. You went from 8 to 6 or whatever. The hours were in a lot of dimensions. There's much more flexibility to design. You're still right though. If you don't know what you want to design, someone will fill in those gaps for you.

Steve Olsher: Yeah, absolutely. And if all you care about is money and a paycheck. So I'm going to tell you you'll find someone to pay you. And it may not be even remotely close to what it is that you're truly compelled to do, but you know, someone will pay you because you have skill. You have talent. Have you been through the University of Chicago? I mean, undergraduate, graduate, doctorate or whatever it is? You've got talent and someone will pay you for it, right?

Anita Brick: So it sounds like the person who has taken five years off maybe takes a little bit of time to zero in on what she wants. And of course she can come and work with us in career services to do that too.

Steve Olsher: For those that aren't familiar with the basic framework insight created in what is your what, it boils down to three specific pieces to be able to answer the question of what is your what? You have to be clear first on what your gifts are. And when I say gifts as an overarching theme, it ties basically what it is that you love to do together.

So a gift, an example of a gift could be like any of it. Your gift is probably communication. I mean, that would be the overarching theme that ties everything that you love to do together. I mean, that's my hunch. The second piece of the puzzle, then, is the vehicle that you will use to share those gifts with the world and the third piece, which perhaps is even the most important piece, is being able to clarify and gain clarity on the people that you are most compelled to serve.

Look, if you're going back to the workplace, you've had this time off. If you don't understand what your gifts are and how you want to express and share those gifts with the world, and perhaps most importantly, as I said, the people that you're most compelled to serve, you're going to end up in a direction that you didn't intend to go. So at least figure out one of those three, let alone all three, before you jump into something.

Anita Brick: Absolutely no question about it, because otherwise you'll end up somewhere, but not where you want to go.

Steve Olsher: Yeah.

Anita Brick: You always center somewhere for sure. There was another question from an alum. How do you reinvent yourself when you're over 50? That is a group that not only has to reinvent, but has no choice but to do so. Clearly, there are different aspects, but your approach to looking at the gifts. How do you want to serve? Where do you have the greatest affinity? Does that change if you're over 50?

Steve Olsher: I think it changes only because of the sense of urgency that is in place. I've worked with thousands of people now over the years, and what I sense in those that are older, especially those that are over 60 more specifically, is that sense of urgency about what does the legacy that I want to leave from a career reinvention standpoint?

You've probably done some amazing things. I mean, anyone who has gotten to the age of 50 has obviously gone through some serious trials and tribulations, and you've survived 50 years of life, and not everyone can see that. And, you know, I don't mean that to sound morbid, but, you know, that's the reality is if you reached age 50, you've done some pretty good things to get to that point.

Now, the question is, how do you shift from prominence to relevance? That's the struggle that most people that I see have as they look to reinvent their lives. There's so many different ways that you can meet so many different directions that you can go. It almost becomes overwhelming because there's so many choices. But where are you going to apply your talents?

How are you going to impact not only those who share this lifetime with you, but also those of lifetimes to come? Because truth be told, you're not a 20 year old. I mean, you don't have 70 years left. You've got a shortened time frame to do what it is that you're truly compelled to do and have that type of impact.

Anita Brick: And the story comes to mind. There was an alum who was actually on the East Coast, and he was struggling because his company had been downsizing, and he knew that it was just a matter of time where his position was probably going to get cut, and he didn't know what he wanted to do. And at the back of his mind, he knew that he had strength in math and science, and he thought about teaching, but he didn't want to just get thrown into the classroom.

He's close to 60. He needed some framework, but he got really clear that he wanted to do something where there was a lasting legacy. Just like you talked about. And he opened up The New York Times a couple of days later, I think, on that Sunday, and there was an application with a looming deadline, actually, for the Woodrow Wilson Fellows program for educators.

And they were looking for people who have, you know, Stem, who have the science and math stuff. And he applied and he got in and he came to Chicago because they were having a conference with all of the current and alumni fellows, and I have never seen this person be more excited and happy. It was just amazing. And I think that what he did was exactly what you said.

He looked at his guests and he found a way to express them where a very clear group was going to care about it, and that it wasn't just his teaching, it was the lives of the people he is and will be teaching and what they go on to do there is that the legacy component.

Steve Olsher: If I may, real quick and you know what? What ends up happening is when you become clear on what your what is, you literally get a player in your soul. I mean, you will jump out of bed every morning just like I've got work to do, you know? I mean, there won't be enough hours in the day to get done what you've got to get done. And, you know, things that used to bother you will carry a lot.

Less weight. That's the beauty of being able to answer that call question of what is your what? Because the end result is that fire, that desire, that knowledge that you're here to do something amazing and you are the solution to someone else's problem. You got to think about it from the standpoint of if you don't discover your what, and you don't share your gift with as many people as you possibly can, you're not only doing a huge disservice to yourself, but you truly are doing a huge disservice to those who are waiting for you and those who are waiting for that.

Anita Brick: Beautifully put. I love that evening student whose family may disagree with you. So let's see how we can help it.

Steve Olsher: Imagine that someone disagrees with me. I've never had that.

Anita Brick: I know, I know, it's like it's crazy. So this evening students and I'm all excited about my career reinvention. That said, my family isn't really as happy as I am. How do I get them on board? That can be really tricky. When we change, the people who are comfortable will change with us, or they'll help us and those who feel uncomfortable with the change might fight us. How can we help them?

Steve Olsher: First and foremost, stop trying to impress the people you don't really like. Anyway, that may sound harsh, but reality is that if you've got people around you who don't support you in becoming who it is that you were born to be, you may damn well need to cut that road. But their family and sometimes that is the hardest thing to do, is we are comfortable surrounding ourselves with familiar faces, and that is just the nature of being human.

We are so afraid to do what it is that we know needs to be done, that we live our lives based on the whims and agendas of others. The real question is, who are you afraid you're going to disappoint? Ultimately, the only reason not to do something is because you're afraid of a reaction, or you lack confidence in your ability to make that choice.

Yeah, I mean, look, there's only two choices. You can be a critic or you can be a creator, and it's super, super easy to be a critic. I mean, you're being a critic now. You're being a critic of my answers. You're being a critic of Anita's questions, you know? So, I mean, it's super easy to be a critic, but it is so hard to be a creator.

And that's why there are so few craters, because most people don't want to go on that limb. And from my perspective, I don't really care if people like Nerf. They hate me. I just want them to know that I was here. Yeah.

Anita Brick: That is it takes a lot of courage, Steve, to do that, though. How did you get all that courage?

Steve Olsher: You got to make a lot of mistakes. And that's the reality is that so many people are afraid to fail. They're afraid to make a mistake. Failure to me is, well, I define it as success with an unintended ending. I mean, because something didn't go to plan doesn't mean that you are a failure or that you failed. It simply means that things didn't go as well as you hoped.

But reality is, it probably didn't go as bad as you feared it might. We become paralyzed. We become handcuffed. We make assumptions in terms of what we believe is going to happen if we do something and we never do it. The truth of the matter is that there is always something you can go back to.

Anita Brick: So I'm assuming that the people on this call, even if they have that critical voice in them, are listening to this because they either are or want to be someone who creates. What are three things that a person could do beginning today to take the next step in his or her career reinvention?

Steve Olsher: The absolute first step is to get clear on the people you're most compelled to serve. If you can't get clear on your gifts and you can't get clear on the vehicle, get clear on the people you're most compelled to serve. And the only way to do that is to do it. So you gotta get out from behind your desk.

Got to get out from behind your computer. Go volunteer, go intern, go be an apprentice. Go do something other than searching online for what you should be doing, because what you should be doing won't be found on that screen. What you must do is out in the world somewhere. That's what most people won't do. They just won't go out there and try 100 things before they find the one thing, or the one subset of the population that they're most compelled to serve.

I think there's a whole bunch in there, Anita. But ultimately, three things one, become clear on the people that you're most compelled to serve. Of course, I would encourage you to be able to solve the whole what is your what equation? But start there. Number two, get in the game right. Do something. I don't volunteer, work for a nonprofit.

Just meet people, but get out from behind your desk. Get out into the real world. And number three, be willing to fail. Be willing to disappoint people. Be willing to make people angry. Be willing to do something that totally and completely is out of your comfort zone, right? I mean, the first time you probably did a podcast where you interviewed somebody, you were like, oh my God, I don't know if I can do this. Perhaps I'm not going to ask the right questions.

Anita Brick: No, no, you're.

Steve Olsher: Right, you're right, you're right. Its comfort comes with repetition. It's just as simple as that. And if you don't get that first weapon, it never gets started. You've got to build momentum.

Anita Brick: Wonderful way of closing, Steve. This time went by super fast. Thank you so much. I love the fact that you are willing to take a stand, because there are tons of critics out there, and being someone who creates and isn't afraid to not have everybody like them is not only refreshing, it's really great advice. Thanks again. I know that you're very busy. I really, really appreciate your taking the time.

Steve Olsher: Yeah, absolutely. And if I, you know, if I might plug the book for two seconds, I don't even want to sell it. I just want to give it to people for free. So if you go to what is your what.com/free. You know, really this isn't about me. All I can do is give people the framework that I created and hope that they run with it because it's amazing what happens when you gain that clarity.

Anita Brick: Steve. Thanks again. This was great. Thanks, Steve and thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.