Start With A Win - John Tarnoff: How to Reinvent Yourself Mid-Career

Episode Date: February 18, 2026

In this episode of Start With a Win, Adam Contos sits down with John Tarnoff whose career story defies conventional wisdom and challenges everything we think we know about success, failure, and leadership in today’s volatile workplace. What unfolds is a candid, thought-provoking conversation about reinvention, identity, and the invisible forces shaping modern careers - from boardrooms to break rooms. With sharp insights, unexpected truths, and moments that may make you rethink how you show up at work, this episode invites you to question old assumptions, confront uncomfortable realities, and imagine a more intentional path forward - both as a leader and as a professional navigating an uncertain future.John Tarnoff is an executive and career transition coach, speaker, and author who helps mid-career professionals build more meaningful, sustainable careers.  After a 35-year career as a film producer, studio executive, and tech entrepreneur—where he was fired 39% of the time—John learned how to turn setbacks into reinvention. At 50, he earned a master’s degree in counseling psychology and built a global career coaching practice.John has led career workshops for MBA programs at UCLA Anderson and Cornell’s SC Johnson College of Business, and coached leaders at companies including Bank of America, Bridgewater Associates, Levi Strauss, SoftBank, and TD Ameritrade.  He is a TEDx speaker, the author of the bestselling Boomer Reinvention, and the creator of the 3 Elements Careerbuilder Framework.00:00 Intro02:05 I’m not the problem?03:42 This process is outdated, do this instead.06:05 You work for them, they don’t work for you!08:36 The more you do this, will build this, because of this!11:01 What are the real responsibilities of a senior leader?13:33 Three Elements Framework.20:31 How to reset?23:01 Closing advice…26:35 Write, write, write!===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook  ➡︎ https://facebook.com/AdamContosCEOTwitter  ➡︎ https://twitter.com/AdamContosCEOInstagram  ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory

We feel so kind of increasingly constrained by all of what we think of as the dings on our background. I believe that unless we reconcile our past, we are doomed to failure in the job market. Welcome to Start with a Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go. Coming to you from Area 15 Ventures and Start With a Win headquarters, it's Adam Contos with Start with a win. Ever been knocked down so many times you start to wonder if you should just stay there or get back up?

It's a tough one. Well, my guest today has been fired almost 40% of his career, and yet he's turned those setbacks into a formula for reinvention. John Tarnoff went from Hollywood producer and tech entrepreneur to career transition coach for top executives and mid-career pros all over the world. He's a TEDx speaker, best-selling author, and trusted advisor to companies like Levi Strauss, Bank of America, and SoftBank. And today, he's here to share how you can bounce back stronger than ever and maybe never

have to go job hunt again. John, welcome to start with a win. It's great to be here. Thanks for having me. Hey, it's my pleasure. You sit in an interesting space of helping people find new careers, get better jobs, whatever might be. And as an adjunct professor in, executive leadership, so basically teaching executive MBAs about things. I hear that a lot. How can I improve my career? How can I get a better job? And it's not as simple as it sounds, which is why you're kind of the career surgeon in this particular space. And I'm glad to have you on today. First of all, you said you've been fired from like 39% of your jobs or something like that. And you've done some

really interesting things. So take us through your history a little bit and how you got to where you're at today. So the 39% figure I came up with for my TEDx talk because I was trying to kind of demonstrate. So what makes me an expert on career transitions and moving through your career? And over the course of my 30 plus years as an entertainment executive in Hollywood, working at studios, through all of the different ups and downs in a very volatile business, I was fired from, I think, six or seven of 18 jobs. And that came out to 39%. I thought it was a fun figure.

I got a laugh, a nervous laugh in the audience. And that's kind of stuck. And I use that really, because who dines out on the fact that they've been fired a lot? It really is, I think, instructive about how the world works today, how the hiring and the firing system works today and how careers are different from what they used to be. So today it's not really about, oh, you got fired. you must have done something wrong. No, it's about fit.

It's about external factors. You're not the problem. You're not the problem. I think a lot of people need to hear that because they wake up in the morning and they look in the mirror and they're going, you're the problem. So why do you say you're not the problem and how can people approach career transitioning or really the volatility? Because you never know.

You could be in a great job, doing a great job, you know, creating a, great results for an organization. They come in and they're just riffing that department. So give me your thoughts on how should we look at this, this opportunity out there? The number one problem that I believe we all have in this economy, in this culture, in this business culture, is that we take an outside and approach to it, which is to say, how do I fit in to what the available opportunities are out there? And any traditional coach will say to you, okay, so let's look at your resume. Let's look at what you do. What opportunities out there can you fit yourself into? That is wrong. That is outdated. You need to bring opportunities

to you by deciding on what your niche value proposition is. And then you have to market the hell out of that so that people come to you for what you value and represent, not for what you think they need. I like that. I like that. You're doing inbound marketing for yourself. Absolutely right. It is totally inbound, right? And that goes to not just the way you position yourself as a product, but the way you encourage activity and engagement on your product. Okay. So let me ask you this. A lot of people go and they get into a job or into a space and they're like, I'm just going to fit in and nobody's going to notice me. And that seems like a huge problem now. Yes. Well, you know, I think the work culture today is so intimidating. And corporations, I think are doing a real disservice to themselves by taking this draconian attitude towards their employees and towards, you know, return to office and all. of these issues about how you must work here and we're going, we're going, you know, hard ass on

everyone here. It's like, come on, guys. There are so many productivity studies which say exactly the opposite, that if you really want to encourage productivity in your team, you're not, you don't want to scare the pants off of them every day when they walk in to think, oh, my God, today could be my last day. You want to create a much more welcoming environment. What does that look like? Give me an example. I was looking at some of the questions that you had prepared for me. And I'm not sure which the question, which was the question, but it was kind of like a general question about what characterizes across all businesses, what characterizes good leadership.

Right. And for me, that notion is the first thing you've got to know about when you're a leader is that you work for your team. Your team does not work for you. And I think that distinguishing quality is what separates good leaders from bad leaders. So if you come from the assumption that you work for your team, well, then you want to make sure that your team is taking care of. It's like leading from behind versus leading from the front. And I think increasingly in an era where we need to be much more strategic about the future, we need to lead from behind. We need to make sure, not that people are following us and come on, let's charge over the hill,

you need to make sure that the people, everyone is included, and you're the shepherd. You're moving the flock forward and you're keeping an eye out for the future. But no one gets left out. That's an interesting statement. And I completely agree with you. It's, and I just taught a leadership course to a couple hundred government leaders. So not like, you know, they're a local government, like county government type folks. And a lot of it was a lot of people go.

into these positions, especially, you know, government position and you have this government and leadership role together. A lot of is based on seniority, but more and more now, it's merit-based. And ultimately, it comes down to how good of a leader are you being in your role as opposed to are you in a leadership role. So, you know, it's fascinating. So typically in a riff or when jobs are eliminated or something like that, they start at the bottom and kind of work their way up, unless they're trying to make a larger financial impact across the board easily. But then there's opportunity for those in those mid-level roles. What is your advice to people when it comes to exercising their leadership on this topic?

Because a lot of people are like, I'm not in a manager role or in a leader role. But yes, you are. I mean, how do we convince people of that and that they need to pick up the ball and run with it in order to lead their team, even though they're an informal leader as opposed to a, a sign leader. I mean, I think it's hard to, it's hard to, it's hard to force the light bulb to go off. Right. Right. And so I would say that, that the more you really listen to the people that you work with, and if you're a leader, particularly, the more you listen and just engage, in conversation with the people who report to you about what they do and ask them questions

as opposed to telling them things or instructing them or reprimanding them, but asking them about what they do. That helps build a relationship of trust. And the more people feel trusted, the more they open up. Right. The more they open up, the more you have an opportunity as a leader to encourage them in areas that are of mutual benefit to you and to them. And I believe that that is one way of starting to encourage the kind of leadership behavior from the bottom up that we so sorely lack in our economy. That's awesome. Do you think So, I mean, when you look at that trust and that transparency and presence creates trust, right? When it comes to sitting at the table, if you sit in meetings all day and you say nothing and you contribute nothing,

and really what you're doing is just kind of using up oxygen in the room and taking a paycheck, clearly that's not a good career move. Yeah. You're probably pretty miserable if that's the way you're living your life. But exactly. But so many people do that and they're like, right? I think it's because they don't feel heard. They don't feel listened to, right?

And they feel like anything they say can and will be held against them. Right. Right. So, you know, it comes down to culture in so many ways. And, you know, I don't know what else to say about that. It is we, look, the fish stinks from the head, right? I mean, you look at all of the ups and downs going on in corporate America and you see that blame is being shifted away from those responsible for making bad decisions towards people who are, you know, on the on the rear end of those decisions. So, you know, it all starts at the top.

And I think we need to, you know, foster a better system of educating senior leaders about what their real responsibilities are. Because, yeah, you put shareholders first. That's going to take your eye off the ball of who is actually delivering the value to your shareholders. And again, it's your team. So, yes, again, you are working for your team to ensure that they make you look good when the quarter comes around. Exactly. And, you know, what's interesting is who's caught in the middle? of this is the hiring manager, right?

Right. And you talk about, I think you've cited a statistic. What is it like every job now has 250 resumes presented to it or something like that? Yeah, that's kind of like the benchmark. And I think with AI, it's now on its way up. I mean, I kind of have predicted that there is going to be this AI apocalypse of job search and job applications where people are using AI more and more to take over the process of not just doing their resumes,

but using agents to submit resumes. So you're going to be able to apply to thousands of jobs by clicking a button, set up a custom GPT to put all your stuff together, submit it wherever there's an opportunity to that might fit you. Well, employers are going to be continually overwhelmed. They're going to have to enlist AI to see. sift through all of these automated applications, and no one's going to be happy. And for me, it all comes back to the fact that in order to get ahead and get a job and build

your career, you need to focus on relationships and focusing on conversations with real people so that they can get to know you, you can get to know them. I think that's the, you hit the nail on the head there, John. The interesting part is, you know, we wait until it's, they've had a job opening in a company. And then we, you know, try and submit a resume or an application or something like that. And then we sit there and wait. And I look at it and I think I would be sending videos to that hiring manager telling them why they need to find my resume. in that stack and have a conversation with me.

I'm going to shortcut you. Okay. And this goes to my three elements framework. Okay. The third element in this framework, which goes to how do you keep the flywheel going, is the idea of thought leadership. So you're on the right track by saying you need to follow up. You need to make yourself top of mind to that hiring manager.

But you actually need to start way earlier. you need to think of yourself in whatever situation you're in, whether you're looking for a job, you're in a job, you want to be a thought leader for whatever the vertical you're in, the niche you're in, you want to stand up for what you stand for as a professional. You want to define one, two, three important issues that are affecting your work, your team, your company, your industry, and find ways to contribute towards solving those issues, whether it is engaging online, whether it is being part of professional organizations, events, mentoring, teaching, the kind of adjunct work you're doing, you want to keep that

set of important ideas flowing so you can engage with people so they'll know who you are, they'll have a footprint to rely on when they're evaluating you for a job. And that's how you bring that presence forward in a way that is persistent, consistent, and serves your interests. So you said there's three parts to this. And that's the third? Yes. Okay.

What are the other two? I'm thinking this backwards. So the first two elements of my framework are, number one, define your superpower and claim your niche. Okay. People don't want special, but they don't want generalists today. They want specialists. Totally.

And part of the problem with being mid-career, and I focus on mid-career, is that you think, oh, I've done all this stuff. I can do anything. You know, here's a job. I can do that. You know, what do you got? Let me, let me help you out. That is confusing to the hiring manager.

He's got a very specific job with a very specific set of responsibilities and solutions that he wants managed. You have to be that perfect fit. The pushback, I guess. as well, but I'm leaving opportunities on the table if I just focus on one thing. That's true, but you need to get in the door. You're not going to get in the door by being a generalist, right? So be a specialist. Number two is once you have defined your special superpower, you need to use your network to bring you the opportunities. Now that the network knows exactly

what it is that you do, it's going to be a lot easier for them to help you. Because before, It's like if you're a generous, it's like, yeah, if I hear of anything, he could do any number of things. I don't know. It just kind of like fades into the woodwork. As a specialist, with your superpower, your network can help you. And you know how to pitch yourself. Oh, I'm terrible at networking. I don't know how to talk about myself.

No, now you do. And if you follow the Iiki guy, right, this Japanese concept of life's purpose, you have the answer to these four questions. What do I love to do? What do I do well? What does my world need and what can I get paid for? That's your product market fit. So the flow is define that special value that you represent. It's authentic.

You have no problem talking about it. Your network understands it. It can bring you opportunities and make introductions because the more people you meet, not the more applications you send, but the more people you meet, the closer you are to getting that next job. And what binds it all together is that third element of thought leadership. Have a presence. Have a consistent point of view.

People know what you stand for. They know where you are the expert. You are the SME on this particular matter. There you go. So essentially, we're not looking for jobs. We're getting those jobs to look for us. Exactly right. I love that.

And it flips the whole equation on its head, right? Totally does. But it's fascinating because everybody's afraid to, and John, you know, this has been a battle that we in the thought leadership space go through constantly as people are afraid to turn on their phone and shoot a video and put it on social media about what they're good at and they're passionate about. Right, right. So here's the proviso about that.

Always be constructive, right? Always be constructive, compassionate. it, never be snarky. Don't feed the trolls. Don't get caught, right? Don't find yourself going down this rabbit hole of grievance or, you know, victimization or whatever it might be. Be constructive. Look for ways to bring people together around the issue in a way that is acknowledging and creative and helps move the ball forward. I like that. I mean, let's face it.

You'll never go wrong. The hiring manager wants nothing more than to go on LinkedIn and fire in a search and find somebody who has a great personality shooting a great video that is valuable and sending that over to the person who needs this employee and saying, what do you think of this person? Exactly. That's what the hiring manager wants. They want to deliver something that makes them look good instead of a resume. Here's some advice for people who are looking for a job on LinkedIn.

And I get into a lot of trouble on this. don't use LinkedIn as your pity party. If you've been out of work for two years and you've sent thousands of job applications, don't ask your LinkedIn to take pity on you, to feel sorry for you, to give you the answer to why am I still out here? I get it. I get it.

It's hard. It's hard. But the people that you want to notice you on LinkedIn are the hiring man. And if a hiring manager sees that all of your posts are about complaining that you haven't gotten a job yet, you think they're going to be interested in contacting you? No. So this is fascinating talking about people on LinkedIn because that's the first place I see as people going on there. I agree they should not have a pity party. Nobody wants to hire somebody negative and then throw them into a new role. The reality is there is a proven framework for this that you have coached people on.

And that's what you do. So with respect to building that foundation, you know, people come in and they're just, maybe they did do something dumb and they're going, oh, I can't get a job. Please help me get a job. You know, looking for work, all this other stuff. How do you hit that reset button? And what advice do you have for them moving forward? So this goes to the idea that your job search, your whole career posture has to be an inside out position. Right.

particularly if you have been working for a while, you're in mid-career, you know, we all pick up baggage over time, right? We have to learn some lessons here. We're not going to be, we're not going have perfect records. There will be bridges that we've burned, mistakes that we've made, deals gone bad, relationships that have fizzled. And part of the problem is that we feel so kind of increasingly constrained by all of what we think of as the dings on our background. I believe, that unless we reconcile our past, we are doomed to failure in the job market. Interesting. Because you're going to encounter all of those difficult questions that you don't want to talk

about when you get into the hiring process and you get into that interview and they say, tell me about what happened at so-and-so company. if you're not prepared to stand up for yourself in that moment and say, look, that was not a great experience for me. And here's what I learned from that. They don't really care that you got fired. They don't really care that you did something wrong. We all make mistakes, right? If they care about that, you don't want to be in that environment anyway, right? They're looking to see how you picked yourself up and how you're moving forward from that. So if you approach this from a place of self-acceptance, vulnerability, resolution on your dodgy past, and you make them feel comfortable

about it, because you feel comfortable about it, you're resolved inside. You know what you did right or what you did wrong or what was done to you, you're in acceptance. And you're prepared to move on and use that hardship, if you will, to your advantage and to their advantage. That's a great approach for that. I love that.

So, John, closing bits of advice for somebody who, you know, maybe they're an entrepreneur, they're going to hire somebody or maybe they're that person looking to join the team in order to carry the ball forward for that team. closing bits of advice for both of those types of people when it comes to finding or being somebody valuable. What do you say before you hang up the phone with them? Oh, as a client, what do I say to them and in my advice for them before I send them out into the world?

Yes. Again, this is an inside out process. If you think that tap dancing and rasmataz and distracts, and distracts, you're, someone by, you know, your stats or your achievements or who you know or what the pedigrees of the companies are that you work for, think again. Because particularly as you get older and you are in positions of hopefully greater authority and influence, they're going to be very, very careful about any decision that they make to bring you in. So you need to be focused not so much on all of the numbers and the, you know, externals, you need to be focused on who you are,

why you do what you do, and where you want to take it. You want to get really down into the weeds with your hiring manager. I was with a client the other day talking about this. He's up for a C-suite role, and he's in marketing. So he's a very kind of marketing focused guy. And I said, don't talk about your record in this meeting with the CEO. Don't talk about yourself at all. If you're in that meeting, you're already the candidate.

It's yours to lose. Right. You need to ask him about him. You need to learn more about how he ticks. And in the process of doing that, share more about what makes you tick as a person. Be vulnerable, right? be engaging and he got the gig. That's awesome.

Because he connected with this guy. At the end of the day, people want to know, can I work with this person? Can I come into the office every day and actually sit down and have a decent conversation? When the chips are down and everything is going to crap, is this person going to be at my back, right? Are they going to have my back? those are the questions that you want to prepare for. And that's the information about yourself that they really want to hear. Great information, John. Everybody, make sure you check out John Tarnoff at John Tarnoff.com. Also, his book, Boomer Reinvention, How to Create Your Dream

Career Over 50. Frankly, I think everybody should read this because it has some incredible information about how to make your career more valuable. It's really anyone over 50. It's now, it's like boomers out of date. It's like now Gen X and millennials very soon, right? So it's really about anyone who is approaching this mid-career crisis, as it were. Exactly. And we all change careers multiple times. So I'll tell you, this is really good information.

Even if you're an entrepreneur, you're going to hire these people. There's some good information in here on what to look for and a great employee because people executing on these principles are the ones that you want in your organization. So check out John online. John's got a lot of great information out there, Twitter, Facebook, LinkedIn, and he's all over YouTube with some really good tips. John, I have a question I ask all the great leaders on Start with a Win, and that's, how do you start your day with a wind? I journal first thing every day. I have a journal by my bedside.

One, just like a little Molescine notebook. Yeah, yeah, right here, buddy. And I write a page every morning. It's like how I prepare for my day. all the reflections, where I'm going. It's an opportunity really to check in with myself and get centered before I get going. Awesome. That's a great way to start today.

I also, again, I've got my great journal right here. And it's a that's it. That is it, my friend. Hey, if you're looking for a way, maybe you're in transition right now and you're looking for a great way to reenter the space. Check out John also. That's his specialty is helping people get there. and providing that advice.

John, we appreciate you being on a start with the Wynn podcast, and thanks for all you do. Thank you, Adam. Take care.