When you have had success, your existence becomes a matter of finding your way to becoming significant and making an impact on the world. For Reinvention Expert Steve Olsher, it is all about identifying the challenge that keeps him motivated, the purpose that he is destined to fulfill in his existence, his “what.” He expounds on this topic as he joins in an insightful conversation with host Jen Du Plessis. An entrepreneur for more than 25 years, Steve is the Chairman and Founder of Liquor.com, author of the New York Times bestseller, What is Your WHAT?, and host of the Reinvention Radio podcast. Through his podcast, books, and speaking engagements, Steve helps people discover the one thing that makes them special and take action to build their legacy through their passion.
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Reinventing Your Way From Success To Significance With Steve Olsher
I am so excited to have a special guest. He is super special to me specifically because he’s also one of my coaches. I would love to take this opportunity to welcome Steve Olsher to our show. Steve, how are you doing?
I am great. Thanks for having me.
Let me give you some context of what Steve does. I love one of the things that you are known as America’s Reinvention Expert, believing that one person has the power to change the world and that’s what we’re going to talk about. Especially with my audience, because a lot of us are either thinking about making that reinvention or that switch and that transition from success in our careers, into making an impact in the world and/or we’re in the middle of it. We are trying to figure it out and reinventing our self every day or we’ve come through it. We’re saying, “This has been a great change for me.” I am excited to talk to you about going from success to significance.
Let me share a little bit about Steve. He’s known as the world’s foremost reinvention expert. He’s famous for helping people or individuals and corporations become exceptionally clear on their “what,” which is what we are going to talk about. It is that one thing that makes you special in the whole world. He is an entrepreneur and was the Chairman and Founder of Liquor.com. He’s a New York Times bestseller and author of What is Your WHAT? Discover the ONE Amazing Thing You Were Born to Do, which all of you are going to have the opportunity to get a copy of. He’s got other books too. He’s also the Founder of the New Media Summit, which is a podcast community that I’m part of and I absolutely love as well. He’s also the host of Reinvention Radio, which is another podcast and Beyond 8 Figures. He’s an international speaker and a coach. He’s been on CNN, ABC, CBS, NBC, Fox Business and TEDx.
We are launching Podcast Magazine.
You’ve had a lot of different successes and have broken through many glass ceilings. Tell us about one in particular that you feel was probably the biggest switch that you made as you went through that transition?
There have been a number of reinventions over the years, but if I had to nail it down to the biggest, it would probably be the transition from real estate development, where I had been doing real estate development for the better part of a decade. I developed over $50 million odd in residential and commercial office retail for sale, for rent types of projects in Chicago. Waking up one day, realizing this is all well and good for me and those closest to me, but no one else. I felt in that moment that I needed to change gears and try to figure out how to leave more of a legacy that I could be proud of. Something that would help others avoid a lot of the trials, tribulations and brain damage that I had to incur over all of those years of trying to figure this out on my own.
That’s when I decided to stop and put the kibosh on doing real estate development and said, “I’m going to start writing and start sharing some of the tips, tools or strategies and shortcuts that had worked well for me in my life in the hopes of potentially helping others.” I didn’t have a clue where to start, but I knew I wanted to get some things out of my head. I knew I wanted to write things down and perhaps, get 1 book or 2 out and maybe do a podcast, maybe do some speaking and those things, but I had never done any of that up until that point. I would say in hindsight, that was probably the biggest shift or reinvention of going from real estate development into this world of personal brand.
[bctt tweet=”Reinvention is all about shedding the shackles that have been cast upon us. It is a process of subtraction, not addition.” username=””]
I know that story behind that too. It’s a very long story. Why is it important for you to be significant and have an impact? How does that feel for you? Where does that stem from? I imagine it’s not just, “I want a legacy for my kids that they could be proud of or someone can be proud of.” It’s leaving your mark on the world.
It’s interesting, now that I’ve been in this world for the better part of a decade or so because on one hand I felt that what I was doing was very ego-driven in terms of chasing that dollar and wanting to have money in the account and doing something strictly for the sake of being able to make money. I felt at that point, that was ego-driven and living from the place of wants as opposed to needs. What I’ll tell you is that, now that I’ve been doing this for as long as I’ve been doing in terms of writing, speaking, podcasting, teaching, coaching and so on, this feels a lot more egocentric than real estate development I ever did. On one hand, I was thinking like, “I want to have a bigger, more meaningful impact and leave a better legacy,” which is why I started down this path.
The reality is I think I started down this path in hindsight, now even more from the standpoint of, “I need to be heard, to be seen, I don’t want to simply be that the person with the checkbook. I want to be that person that will be remembered, not by those who share this lifetime with me, but also by those of lifetimes to come.” On one hand, it’s like, “I’m doing this for everyone else to help them.” In reality it’s, “No, I’m even more so doing it for myself,” which is an interesting conclusion to be able to come to now, after having been doing this for as long as I’ve been doing it now, sitting back and being honest about why I’m doing the work that I’m doing.
I want to bring that back so that you don’t feel so bad about that, but I think there’s an element for anyone who wants to not look at life through dollars and we still do. We all have to make a living, but we’re not looking at life through dollars. We’re looking at life in a way that touches people and that leaves something onto perpetuity in someone’s life. It’s very risky and very bold. It’s a bold thing for someone to want to be on stage, want to share and want to give back to people.
It’s probably one of the most honorable things that people can do. I look at it that way that it takes a lot of risk and you know that people are going to size you up, say good things and bad things about you. It’s much easier to go and do your little job and not be out there like that. I think that you’re may be cutting yourself down a little too much, but that’s just me. One of the things that I’ve always thought and I have this in my book too, is that I think that what we do when we’re younger, we learn and then we spend most of our life earning. We get to this point where we want to return. We learn, we earn and we return.
Most of the people that are reading this show are in that stage. They’re either straddling the earning and they’re at the end of the earning. They’re saying, “I want to give back. I want to return and share with other people.” Let me talk to you about, what motivated you? If someone’s reading and they’ve got a great career, everything’s great and they’re in stability, everything’s wonderful, what motivated you day in and day out after you made that decision that says, “I’m not going to be in someplace where I’m very comfortable. I’m going to go to something that I’m not feeling it. I don’t know. Is this going to work?” What was the motivation that kept you going?
Men and women are wired, in some ways that are very similar and in some ways that are very different. For me, it’s something that I’ve been able to have conversations with other men about not so many women so much. I’d be curious in terms of your take on this. I do think it boils down to the need to have consistent challenge. Once you reach a certain point of comfort of having what it is that you need and being very clear on what it is that you want, as opposed to what you need. For me, I have everything that I need. I’ve got the house and the cars. I don’t need any more.
To that end, I don’t drive a McLaren. That’s not what I need. Once you have everything that you need, and then you don’t have anything else on the list of things that you want, then what? I think ultimately that’s where it becomes difficult and certainly, staying with the theme here of moving and shifting from success to significance. It truly then becomes a matter of identifying that challenge that will keep you motivated. It is truly the challenge of how do I as a mere mortal compete in a game where other people have much bigger platforms, much more notoriety, much more of the recognition factor?
That to me has become the driver and the challenge. It’s saying, I can put myself into any conversation that I want to be put into. That conversation for me is podcasting. How do I put myself into that conversation where when people think of those who are having an impact in the world of podcasting? I’m not Joe Rogan. I don’t have a show that has 30 million downloads a month. I don’t have a huge platform, like Will Ferrell, who can launch The Ron Burgundy Podcast and end up on Colbert, Jimmy Fallon and Jimmy Kimmel on the same night announcing the launch of season two of his podcast. How do I put myself into that conversation? That’s the challenge.
I loved that you’re always looking forward, you’re always trying to find new ways to challenge yourself and especially when there’s someone like you who had a very successful career at a very young age, because there’s so much life left. I think that in the old days and I don’t mean old days in 2000, I’m talking about old days. There were probably a lot of men who gave up on a lot of things that they loved and lost their passion because they were stuck. We have this wonderful world now that allows us to go into that entrepreneurship. It’s okay to reinvent, don’t you think and do it often?
It also then begs the question of what does it mean to reinvent. For me, reinvention isn’t about some drastic change necessarily. In my mind, it is more about shedding the shackles, the characteristics, the traits, the expectations, the agendas, and whatnot of others that have been cast upon our shoulders, including what we cast upon ourselves over the years and shedding as much of that access as we possibly can to get back to the core and to the essence of who we truly are. Reinvention to me is more of a subtraction than it is an addition.
I think that’s going to mean something different for everyone. I’m sure that’s what you found as well as what reinvention means. For everybody, it’s something totally different. We’re also talking about life after breaking through all these glass ceilings. It’s not just financial, but it could be health or family or relationships. Someone might be going through that now saying, “I want to make an impact on the world, but I’ve tried it this way, now I’m trying it that way.” What did you find in your experience and do you feel, in your opinion, is it okay to go down one road and then come back and say, “That road didn’t work and let’s go down the other?” What would you say to someone who’s in that position and feeling very frustrated?
First and foremost, I’ll be honest here. It depends on what age you are. I mean that with all sincerity. I turned 50 and I look at where I am now in my entrepreneurial, my career path. If I’m going to sink my teeth into a project or whatever that project is that I decide I’m going to move forward, maybe that’s a five-year project when we’re all said and done. Maybe between getting it going, moving it forward and getting it to the point where it can flourish. The truth is at this age, we only have so many more of those five-year windows. The reality is that the amount of energy that it takes to bring some initiative to fruition, that doesn’t decrease because you were older, you still have to have as much time and energy, in some cases, resources going into that endeavor, into that initiative.
The energy and strength that you bring as a 20 something, as a 30 something, you’re not going to bring to the table as a 50 something, 60 something, 70 something, you’re not. It’s a combination of, “How many of those windows do I have left? How much energy do I have to expand, to put into bringing something like that to fruition?” As you look backward, obviously you can’t change anything insofar as what you’ve done and how it got you to this point, what you’ve learned from that and how it’s benefited you in terms of what you can now leverage moving forward. You can’t go backward. If you’ve made those mistakes. I’ve made a ridiculous number of mistakes and some of those mistakes have been very expensive too.
I’m working harder than I would like to be working at this stage because of some of those mistakes that I made, but at the same token, where would I be now and what would I be doing if those had come to pass in the way that I envisioned that they would play out? In other words, I do subscribe to the notion that everything does happen for a reason. I wouldn’t be where I am now, doing what I’m doing now if some of those initiatives had taken a different term. Is it a mistake? Should you look back? First of all, you can’t do anything about the past, which is a hard lesson for any of us to learn.
I think that the easiest thing to do is as you grow older, is at least to get yourself out of that state of mind as quickly as you possibly can, where you go, “I’m focusing on the past and I can’t do anything about it. Let me now shift my mindset to what I can do here in the present.” I think it all serves you at the end of the day, but at the same token, a lot of that is painful. We have to acknowledge the pain and forgive ourselves for the mistakes that we’ve made. Unfortunately, some people just cannot get past the point of that pain and can’t forgive themselves and that’s a whole other conversation.
[bctt tweet=”You choose your ‘why.’ Your ‘what’ chooses you.” username=””]
I call it wisdom and I work on it every day to get as much wisdom as I can make. To always be mindful of some of the decisions that I made in the past, “Am I continuing a pattern doing that?” One of the benefits to age in this transition is that you do have those mistakes that you’ve made. Maybe that can offset the energy that someone younger has, is that you’ve made those mistakes. I think that’s extremely important for us to always remember. Especially, like the fact that you said that we need to forgive ourselves for the mistakes that we’ve made and I think that’s really key. This is a little fact. It’s 3,800 days left when you’re 50 for the average person who lives to the average length of time, because my daughter has 21,000 and it’s not good.
That can’t be right because that would be over ten years.
That’s the average person not in life, in working.
What do you do?
I only have 800 days to make a ton of money. I don’t have to work.
What are you going to do?
I’m going to play.
Why can’t you play now?
I do, but I wanted to play more.
I think it’s a little bit of a misnomer in terms of that whole success to significance conversation too, which is, “Why can’t you be significant in this very moment?” Interestingly enough, my TED Talk called You Are Significant. That’s very much aligned in our ways of thinking here. The fact of the matter is I look at my dad, as an example, who has been retired for the better part now of about 10 or 15 years. He hasn’t done all that much in those last 10 or 15 years and he can do whatever he wants, it’s his life.
This goes back to the conversation we were having about the need to be challenged. Who am I to put together Podcast Magazine? First of all, as soon as you start talking about a magazine, about podcasts, the haters come out and they’re like, “Why don’t we do a podcast about Podcast Magazine?” It’s dumb stuff. That’s going to happen but look at the same token, “I need the challenge.” Why shouldn’t Podcast Magazine have the ability to be as influential around podcasting as Billboard Magazine does around music or Wine Spectator does around wind or Cigar Aficionado around cigars? Is that possible? Could we have that influence with the magazine? I don’t know. Time will tell.
For me significance, isn’t just clients, helping and going down the entrepreneur path. For me, making that impact and significance is making sure that in 100 years, it matters what I did. I’m 100% German, it’s always about cleaning and making sure the house is spic and span and the kids, yell at them when they were little. My mom would say, “In 100 years, it doesn’t matter that your floor was swept now, but what will matter in 100 years is the impact that you had on your children and your children’s children that they say, ‘Years ago, your great, great, great grandmother loved doing this. She made an impact here.’” It’s not that when you move from success to significance that you start getting in a rocking chair. It’s more that you have the opportunity and the wherewithal to be able to influence anything you choose to influence. Anything you can choose to do.
That’s what I’m aiming for is to do what I’ve always wanted to do. Now, that’s the path to get there. You say this all the time. Stepping over dollars to get to dimes. I used to think and still do that all the loans that I did when I was in lending wasn’t about the money I made doing the loan. I was stepping over that money to get to the legacy I wanted to leave for my kids. It provided me the ability to do that. It’s a conversation that I think a lot of people are having with themselves.
Let’s play that out for a second, because the income generated was fuel to create that legacy. At the same token, it begs the question of, “Why wouldn’t you start on the legacy piece immediately?” For those who are thinking about it, I need an X in the bank in order to then start focusing on, “Why?” in the legacy. It’s this and that. It begs the question of, “If you put that much energy into whatever it is that you would do when you cross that arbitrary line in the sand that you create. If you invested the next ten years into that, as opposed to ten years and putting money in the bank and then move into that legacy piece, where would you be in that same ten-year period? If ultimately the legacy piece is what is most important to you, then why wouldn’t you start on that now?” In other words, if you’re thinking about the stepping over dollars to get to dimes analogy, then what you’re doing is you’re stepping over the legacy piece to get to the money piece, which what’s important to you.
I see a lot of people doing that. When I was younger and it was probably me being surrounded by the family that I was surrounded by and then entrepreneurial spirit that was there is that I knew that I wanted to leave something for my family that was going to be for perpetuity. I wasn’t going to start when I was 70. I was going to start when I was 30 and I did. Now, it’s other things. You learn, you earn and you return. You start learning new things that you want to get back to people and I think it’s cool when people take action on that. I want to talk to you about What Is Your WHAT? What it’s like to be Steve Olsher as it relates to What Is Your WHAT?
As you are well aware of and is clear by your own work and the book that you’re writing and there’s an author land. We do write the book that we most need. That question of what is my what is one of those questions that’s always been there at the forefront for most of my adult life anyway. After having tried the Myers-Briggs and what color is your parachutes and the StrengthsFinder, all of those modalities that left me with more questions than answers. It was like, “There has got to be an easier way here to try to figure out what it is that I’m truly compelled to do, how I am naturally wired to excel and what it is that I can be doing with the years that I have on this planet?”
[bctt tweet=”We all have the ability to get paid extraordinarily well for what comes to us as naturally as breathing.” username=””]
That is the impetus for having created the What is Your WHAT? framework is trying to figure out what really are the most important pieces of the puzzle that we need to have in place in order to hit the ground running and to start having the type of impact that we want to have while earning what we know we deserve. That’s how the What is Your WHAT? framework was born, which is quite simple in terms of the fact that there are three primary pieces of the puzzle. The three pieces that includes your core gift, which is basically how you’re naturally wired to excel. For some, your gift might be something like communicating, teaching or entertaining. Others, it might be enrolling, protecting or healing or whatever that is for you, but having an understanding of what your core gift is.
Once you have that understanding, then it becomes a question of, “How am I going to share that gift? What is the primary vehicle that I will use to share that gift?” Lastly, then it’s a matter of understanding who the people are that you’re most compelled to serve, and you want to share that gift with. As I began wrestling with this equation, what I found is that if you can get clarity around your gift, your vehicle and your people, it does give you the ability to start putting into action, the discoveries that you bring to the surface. It’s a lot like a tripod though.
You can be clear on what your gift is and you can be clear on what your vehicle is, but if you don’t have clarity around who the people are that you’re most compelled to serve that doesn’t work. If you know who your people are and you know what your vehicle is, but you don’t know what your core gift is, how to share that and leverage that, that doesn’t work either. You can run six ways from Sunday, but at the end of the day, most people will spend a lifetime trying to figure out one piece of the puzzle, let alone solving all three. If it’s a question of, “I don’t know what my gift, my bagel or my people, or I don’t know what those answers are,” then know that you’re far from alone.
How is this different from the Why?
We actually had Simon Sinek on Reinvention Radio and that was a fun little conversation around the Why versus the What. I believe that at the end of the day, you can choose what your Why is. Simon and I have a difference of opinion on this. He’ll tell you a semantical question. I think it’s a very different question in terms of answering, “What is your Why versus what is your What?” To me, you can choose what your Why is. Most of the time, why you do what you do is a reflection of a desired result in terms of, “I want to provide clean drinking water for children in India,” “I want to feed starving people of Africa,” “I want to do X, Y, and Z.”
Whatever it is, if you choose why you do and what you do, “I want to take care of my family,” whatever it is for you versus your what, which if you look at the cover of the book, What is Your WHAT? you’ll see that the only graphic element on there, is the DNA strand. That is because I believe that your why is external versus your what, which is very much internal. When you come right down to it, your what has chosen you as opposed to that being something which you have chosen. I believe that you can choose your why. I don’t believe that you can choose your what.
I love it because it mirrors so well with my coaching programs for loan officers and realtors, which is the lifestyle business mastery, and it’s keeping things in alignment. I would say to anyone who’s reading, if it feels like there’s a rub in what you’re trying to do and where you’re heading, it could be because it’s counterintuitive to who you are, someone’s planted a seed for you that says, “You’re good at accounting,” because you’ve been an accountant all your life, “You should do more accounting or teach other people how to do accounting.” If it was a job and it wasn’t your passion and it’s become something that’s different. I think passions change too. What’s passionate for a 21-year-old is definitely not passionate for someone who now has children, their passion has changed and their values change. It’s digging in and finding that and making sure it’s in alignment.
I don’t recommend pursuing your passion as a career. That almost never works out.
That would be dancing. That’s what I would be doing.
You may have been very good as a dancer, but it doesn’t mean that you would have made a living as a dancer. What you’ve got to do is look at the number of cupcake shops that are closed. Just because you grow awesome tomatoes in your backyard doesn’t mean you’re going to be a commercial farmer.
I do think there’s an alignment in there that you know. You know what gets you going and sparks and you know it’s a gift for you as well. It’s a gift that you can give to other people. Steve, I know that we’ve only touched the surface of all of this and I want to say, thank you so much for sharing what you have shared with us. I encourage everyone to get the book and we’ll have the link here as well so you can get the eBook of What Is Your What? What else would you like to leave with everybody? What’s one is your favorite quotes?
I’ll share one of my own which is, “I wholeheartedly believe that you are the solution to someone else’s problem. The reality is that there are people who are literally waiting and praying for you to show up in their lives. You’re not only doing a huge disservice to yourself when you lack clarity on your what and you’re not out there sharing it with strategic abandon, but of course you’re doing a huge disservice to those who need you and are literally waiting and praying for you to show up in their lives.” I’m a firm believer that we all have the ability to get paid extraordinarily well for what comes to us as naturally as breathing.
It doesn’t take a lot of people, but there are people out there right now who need what you have, whatever it is, whether it’s a product, a program, a service, it’s knowledge, it’s time, it’s energy or whatever it might be. When it comes to public speaking, because a lot of people always ask me, “How do you get these stages, this, that and the other?” Big stages start out as small stages and big bank accounts start out with a small bank account. You’ve got to start down the path and ultimately, it’s the reward that is waiting for you for gaining clarity on what your what is and sharing that as best you can, is something like anything you’ll ever know.
It’s taking the risk to put yourself out there because you have a message that you feel people are looking for. One of the things that I say, “Lord, please help me find that one person who’s out there looking for me.” It’s along the same lines of that there are people out there looking for what you have to offer, for what you as a reader have to offer. It’s about getting, going, get moving and get learning about yourself so that you can share it with the rest of the world.
For those of you who are reading, I want to say thank you so much for joining us. If this was your first time, welcome. We’re glad to have you in our community. If this is your 100th time reading, I want to say thank you so much for paying this forward and sharing it with as many friends as possible. Please don’t forget to give us a great five-star rating and write us a review. If ever you need anything or want anything from me on this show, please be sure to reach out to me at JenDuPlessis.com. I would be happy to find that perfect person to share their message with you so that you can continue to move forward. Steve, thank you. What a blessing it has been to have you on our show.
I appreciate you having me.
- Steve Olsher
- What is Your WHAT? Discover the ONE Amazing Thing You Were Born to Do
- Reinvention Radio
- Beyond 8 Figures
- Podcast Magazine
- Simon Sinek – Reinvention Radio previous episode