Navigating a Mid-Career Crisis, And How to Spend Your 20s

This week, we're revisiting our favorite listener questions about work and career. Scott Galloway explains how to get hired again after a layoff in your 50s, what he'd do differently starting his own career, and how to think about stock options in a first job offer. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Plus, you can now call or text Scott a question at our new Office Hours hotline: ‪(201) 472-3656‬. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Scott Galloway?

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• 0:39Speaker 01

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• 1:09Speaker 02

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• 1:44Scott Galloway?

  Welcome to Office Hours with Prop G. Today, we're revisiting some of our favorite questions about work and career from navigating big decisions to building a more fulfilling professional life. Let's bust right into it. Question number one comes from Reddit. Dwin Dolvak asks, "With the average tenure of a job being just about four years, how can those of us in our early to mid 50s who have been impacted by layoffs but cannot yet retire convince companies to take a chance on us?"

• 2:08Speaker 03

  Yeah, so what you're feeling is real. There's some data here. The job stability and the disruption is being felt by people, I'm gonna say older mid-career. A major 2018 study found that more than half of workers in their early 50s who had long-term jobs were laid off after age 50. Many others struggled to find steady work again or saw their pay drop by 50% or more for years. So first off, ask yourself a question. Can you not get a job or can you not get the job that you expect that you should have right now? You might have to take a cut in pay, boss. And just back to the notion that can you get a job or can you just not get a job you want? No one ever thinks they're overpaid. Nobody at Prop G thinks they're overpaid. And let me tell you, they are. I'm on AI. I try to pay people between 30 to 50% above market, but no one thinks they're overpaid. They just say, "Oh, okay, I won't leave."

• 2:50Speaker 03

  But no one, no one sits around and says, "Hey, mom, I'm overpaid." No one ever feels overpaid. And just statistically, and I can prove this to you, 50% of the time in your career, you were overpaid and 50% you were underpaid and almost 0% of the time, whereas it calibrated exactly. And going to the next job, the natural kind of progression or instinct is, "Oh, I should make next, the same amount or more at my next job." Maybe not. I think the workplace has become increasingly ageist as I sit here with a swollen face from my, just having my eyes done. And it's really strange. A lot of times when people like my content, they reference my age as a means of being critical. And I remember at L2, I hired a systems engineer who was, I think in his 40s or 50s. And the vibe was, dude, what happened?

• 3:35Speaker 03

  I think if you're in technology and you're a male and you're in your 40s or 50s and you're not running the place, you're not already a multimillionaire, the general view is like, "Oh, my God, you fucked up." I think you're just gonna see a boom in cosmetic surgery and botox and all that shit amongst men who are feeling the same ages and women have had to endure for a long time. You're in a tough spot. I don't want to sugarcoat it. And I also think that the hard part about looking for a job in your 50s is you're not willing to eat as much shit. My companies right now would be more successful if I were more aggressive and less arrogant. And my arrogance has been a bit of a function of my age. And that is, I think I could go out and get a million dollars in incremental advertising if I was willing to go have dinner or not play golf, but socialize with ad buyers or brands or same.

• 4:20Speaker 03

  Sameos retell to me all the time, "Let's get together." I'm like, "I don't want to hang out with you. I'm gonna hang out with my kids." And I don't feel, I don't do pre-calls. I know I'm boasting right now, but it's true. I don't take advantage of 98% of the opportunities thrown my way because I'm at a point in my life where I'm like, I'm just not willing to hang out with some 35 or 40-year-old that I don't want to hang out with. I find that the key to getting a job is how social you are. Study done at Google, they put out a job opening, 200 CVs within like 60 minutes. They shut it down. They bring in the 20 best candidates and 70% of the time, the person they end up hiring has an internal advocate. So, one, a boss, if you're in your 50s, it doesn't matter if you're in your 50s or your 20s, the advice we would give your 22-year-old self, you gotta make a bunch of calls, you gotta get out a big spoon and eat shit. Call people you don't want to call.

• 5:06Speaker 03

  Follow up, which sucks when you're older, which means you're bothering people that don't want to hear from you. Be willing to ask other people for help. Reach out for copies. Hey, do you know anyone? I'm looking. But also be as social as possible. Because what I have found is that when I hear from a friend that they're looking, that my antenna go up and I start trying to, I need to do a better job of this, of identifying potential opportunities for them. When I see them recently and they call me and say, "Hey, do you know anyone at Salesforce? I'm interested in this position." I'm more inclined to return the email or leverage one of my contacts to try and help them. And, you know, it's like finding a boyfriend or a girlfriend or friends or it's like kind of like finding a job. It's a little bit, it's a lot of it is serendipity and you want to create serendipity by putting yourself in a position around as many other mammals as possible.

• 5:51Speaker 03

  So it sucks to be in the position where you, I'm sure you've been good at what you did. You think at this point, your momentum and your skills would open doors. I've found even the most robust economies, it's never easy to get a job. But I think you have to do whatever it is to make yourself feel, you know, build your self-esteem. Because every day, boss, every night, you gotta write down a list of three or six things you're doing the next day when you grab that spoon to eat shit. Emailing people, going on LinkedIn, going out, networking. I do just think it's a numbers game. I don't think there's a silver bullet here. Also, some of the ageism you might be feeling, some of it's real, but some of it's also probably self-inflicted and that is, it's probably not as bad as you think. You're just, you're just start to get self-conscious about it. Unfortunately, you're in a bad part of the cycle.

• 6:34Speaker 03

  The way you described the labor market right now is no hire, no fire. Companies, the whole AI tsunami of layoffs has not really happened outside of tech where the early adopters here. Does that presage more layoffs? Probably. But also firms aren't hiring because they want to see what happens to the economy. It's like the housing market right now. There's just a lack of transactions. There's very few buyers and very few sellers and the labor market right now is kind of no hire, no fire. So, yeah, it's bad, but it's been worse. I literally, when I was younger, I used to stand in front of a mirror and say, "I know I can make someone happy." You know, because I was constantly single and really wanted a girlfriend. "I know I can add value to a company." I was constantly starting companies, failing. "I know I can add value to a company."

• 7:17Speaker 03

  You know, I was always trying to like manifest and tell myself that I had value. And I think that, I think that's really important. And also, if you're feeling any anxiety, action absorbs anxiety. Write down a list and just start sending out emails and making appointments and calling on people. Sorry for the word salad here.

• 7:35Scott Galloway?

  Question two. Question number two comes from Rachel Sarecki on LinkedIn. Rachel asks, "I'm an upcoming college graduate. What would you do differently when you first started your career? Any advice for navigating early career life?" Huh. What your first job most likely will be is something you hate. And that is, first time jobs are usually shitty jobs, usually doing all the work that people who have some power don't want to do. One of the biggest blessings I, greatest things I got from Morgan Stanley was wanting attention to detail. It was an incredibly abusive environment and I don't, I mean, I quite frankly, think that was good for me. It kind of toughened me up. Lot of guardrails. You had to show up in a tie. You had to be well-prepared. And it was incredibly taxing and stressful, but I kind of needed a swift kick in the ass.

• 8:18Scott Galloway?

  And also the brand itself and the platform, I think, obviously helped me for the rest of my life and helped me get into business school. And I was around really talented people. So what do you want to do in your first job? You want to find a place where you can learn, ideally a good platform or brand. I think the office is a feature, not a bug. I would really, really advise against taking, doing remote work. When you're young, you need to find friends, mentors and mates. One of three relationships begins at work and HR people hate that, but show me an HR person who's putting in all these strict policies around dating. I'll show you someone who, you know, found his wife at work. Get into the office, try and get to a good platform, try and go somewhere that'll let you run flat out. One of the things I did, and this sounds strange and you couldn't do this now or they

• 9:02Scott Galloway?

  wouldn't let you, every Tuesday morning, I'd go in at 9:00 AM and I would stay till 6:00 PM the following Wednesday. Because I wanted to send a signal that I was here to play. And unfortunately, Morgan Stanley was the kind of abusive behavior where they sort of rewarded that. And I think they used to give us a clean white shirt the next morning. At the end of the year, they'd line up all the analysts and count how many white shirts or how many of them had pulled all nighters. So I got into a good platform. I worked my ass off. I was very focused on work. I took down the alcohol and the pot intake for a couple of years. And I just sort of wanted to show that I was here to here to play. Because the sad truth to your career is that people say, oh, enjoy your 20s and have fun. Anyone who tells you to do that is already fucking rich. Unfortunately, in a capitalist

• 9:42Scott Galloway?

  society, your 20s sort of dictate your trajectory into your 30s and 40s and your ability to kind of get to the right positions in your 30s and 40s to really then aggregate influence and economic security are somewhat a function of the trajectory or the scale or the velocity you establish in your 20s. The metaphor I would use is a projectile or a rocket getting into space. And that is the majority of the fuel expectorated in a launch vehicle, you know, whether it's a Falcon Heavy rocket or Saturn rocket, so whatever, it's in the first few miles. The lower orbit is soupy. It is really hard to get traction right out of school. So you want to burn a lot of fuel. What does that mean? You want to work really fucking hard. You want to try really hard. You want to invest in relationships, be seen

• 10:25Scott Galloway?

  as a good ally, do shit work, have a great attitude, just be curious. The other thing I would suggest is that you do you try and find mentors, ask people out for coffee, develop a kitchen cabinet of people who advise you. When you ask people for help and they say yes, they become emotionally invested in your success. The most loyal or patriotic Americans are veterans. Why? Because they've invested so much in America. And my first boss, this guy Carter Cordner, I used to constantly be in his office asking for advice. And he started taking me to UCLA basketball games. And he took a shine to me. I think it made me one of the few reasons I wasn't fired. I was not very good at that job. And but he really liked me and was invested in my success, wrote my letters of rec. And I really invested in the in the relationship, if you will. So this is a time to work your

• 11:10Scott Galloway?

  ass off. Find a platform where ideally, it's a good brand, where you're going to learn a lot. Absolutely get into the office, try and invest in relationships, and also just realize it's a soupy atmosphere and you're going to burn a lot of fuel. You need to try really hard and work really hard. And also forgive yourself if you don't like what you're doing. That's a gift. I figured out almost right away, I was not cut out to be an investment banker. And that's a gift, too, because I realized what I didn't want to do. But that's fine. Your 20s is for workshopping, not only finding what you like to do, but what you don't like to do. Now, having said that, give everything at least two or three years. Try really hard. Show up, be on time. And the objective in your 20s is not to find your passion. It's to find something you could be good slash great at. And so

• 11:52Scott Galloway?

  every job you're in, think, okay, could I be in the top 10% of whatever it is I'm doing within, say, five years? And could I be in the top 1% in a decade? Because if you're in the top 10% of something, you're going to make a really good living at it. And if you're in the top 1%, you're going to get prestige, relevance, camaraderie that will make you passionate about whatever that thing is. So that's my advice. Oh, my God, that was a word salad. We'll be right back after a quick break.

• 12:27Scott Galloway?

  Support for the show comes from Superhuman. The pace of modern work can be relentless. You're getting a constant influx of messages from a ton of different apps. You haven't closed all your browser tabs in a year. Everything seems urgent and staying on top of it all feels like an impossible task. Superhuman Go is an AI chat that's always there when you need it, already aware of what you're doing and doesn't ask you to start from zero. Superhuman Go, from the makers of Grammarly, help you be the best version of yourself at work. It handles the repetitive stuff so you can focus on the work that only you can do. Whether you need to summarize an endless email thread or prep for a meeting that's happening in five minutes, Superhuman Go works inside the tools and sites you already use, your browser, inbox, docs, and your project tools. And its AI chat is available

• 13:10Scott Galloway?

  on the side of your browser and it's always ready. No new tabs, no switching apps, no losing your place. This is AI that works with you, not on top of you, so that you have the time and brain space to solve the problems that matter. Check it out. Find out more at superhuman.com.

• 13:30Scott Galloway?

  Support for the show comes from Upwork. Trying to scale your business? At some point, you're probably going to hit a point where you need some help. Sometimes the best way to break through that is bringing in the right talent at the right time. Upwork can help. Upwork is a one stop platform where you can find, hire, and pay expert freelancers across more than 125 categories. Whether you need specialized skills for a single project or extra support to keep up with demand, it's easy to connect with experienced professionals, review their work, and find the right fit. You can move faster without taking on the commitment of full time hires. And for businesses that need the very best talent, Upwork Business Plus provides access to the top 1% of freelancers on the platform. AI powered matching connects you with qualified candidates in under six hours, cutting down

• 14:11Scott Galloway?

  the time spent searching. Upwork also takes care of contracts, payments, and other administrative tasks, so you can spend less time managing logistics and more time focused on what's next. Visit upwork.com/profg right now and post your job for free. That's upwork.com/profg to connect with top talent ready to help your business grow. That's U P W O R K dot com slash prof G. Upwork.com slash prof G.

• 14:40Scott Galloway?

  Support for the show comes from Square, the easy way for business owners to take payments, book appointments, manage staff, and keep everything running in one place. Think of your favorite small business. I absolutely love Dig. It's this restaurant that feels like comfort food or homemade food. It's just down the block from me in Soho, and I think they do a great job. Whether they serve, you know, comfort food, teach yoga, or run a landscaping company, Square helps the small businesses you love thrive. And if you run your own business, Square is built to work wherever you do, from single location shops and pop ups to mobile businesses and multi-location franchises. You can take payments at the counter, through a kiosk, online, or right from your phone with everything synced in real time. And built in tools, including Square's loyalty and marketing, help you stay connected with customers and give them more reasons to come back. When

• 15:24Scott Galloway?

  you're behind the counter, or on the go, or running the whole operation itself, Square can help you track sales, manage inventory, and access real time reports from wherever you are. With Square, you get all the tools to run your business with none of the contracts or complexity. And why wait? Right now, you can get up to $200 off Square hardware at square.com/go/profg. That's S Q U A R E dot com slash go slash prof G. Run your business smarter with Square. Get started today.

• 15:59Scott Galloway?

  Welcome back. Question number three.

• 16:00Speaker 04

  Hey, Scott. I'm graduating this upcoming May with a mechanical engineering degree. I have a few job offers lined up, and I feel really fortunate, given the current job market for new college grads. One opportunity I'm particularly excited about is an aerospace startup. And I'm excited about it because the company is well positioned within a rapidly growing sector. When I reviewed the offer, I noticed that a large and meaningful portion of the total compensation comes in the form of incentive stock options. As someone who's been only been paid hourly as an intern, I'm not sure how to value them or what the tax implications are. How should early career professionals think about ISOs? And what advice do you have for young professionals navigating stock options for the first time?

• 16:42Scott Galloway?

  Current income or your salary, generally speaking, 90 to 98% of us will spend everything that comes to our hands, especially as a young person. My first job was at Morgan Stanley, and I was making more money than all of my friends. I don't think I saved it. I saved enough of it to go to Europe, but I didn't really save any of it. Because when you're young, and you have money, and you live in a capitalist economy with millions of AI driven offers every second, everywhere you look, it's very hard to hold on to cash. And you'll always convince yourself that, oh, an upgrade from economy to economy plus is an investment in myself. And I'm going on a date, so I shouldn't, you know, spend more money. It's just really easy to just spend everything. So an ISO is an incentive stock option. Now, essentially, a stock option is, say, your company, this aerospace company

• 17:24Scott Galloway?

  is worth $100 million, and they give you 0.05% of options. That's equivalent to options on stock worth approximately $50,000 at that moment, usually at vests over four years. So they're saying, all right, we're going to pay you 80 or 100 grand in salary, and we're going to give you options that have a notional value of $12,500. Now, if they just gave you the stock right now, it's a taxable event. What that means is you'd have to pay tax on the $12,500. So options are not taxable at the moment they're granted, meaning they're saying, okay, we want you to be motivated. We want you to act like an owner. So the company's worth $100 million now. We're going to issue you options, meaning you have the option to buy our stock at a predetermined price at some point in the

• 18:09Scott Galloway?

  future. Now, the great about common equity, which you'll be getting, is sometimes it's valued at a much lower price than the $100 million that maybe they just took valuation, they took capital in. So say it's valued at 20 or 30 million, because common is less valuable than preferred. I'll go into that at some other point. That means at some point, if the company gets sold for 300 million, if you exercise those options, you have to buy, you have to write a check to exercise those options, but it's at a lower price than the notional value. And then if you hold on to the equity after you've bought those options or exercise those options, if you hold on to it for less, for more than a year, you get long term capital gains, which is taxed at a lower rate than your current income. All of this is a long winded way of saying that equity is how you get

• 18:54Scott Galloway?

  wealthy. And what I would do is I would go to AI, and I would type in the name of the company, the valuation of the last funding round, how many options you've been given on how many shares at what strike price. It's probably going to ask you what is the total number of outstanding shares. And then you're going to say, what are these worth right now? And it'll give you a notional value. The reason I bring this up is, one, it's an absolutely fantastic way to build wealth. And two, if you're going to negotiate anything, when people are saying, I've got an offer I want to negotiate, if you have a second or a third offer, what you may want to say is, love the company, want to start here. Can you see your way clear to increasing my options package as I want to be an owner?

• 19:34Scott Galloway?

  I really believe in this company. That's what I tell people to negotiate around, because your option value grows tax deferred. What do I mean by that? Say your options double in value. Until you exercise them, it doesn't get clipped. In other words, you don't lose 37% of it every year. Whereas the money you get paid in salary, every year, you lose 30 to 40 to 45% of it. So it doesn't grow as fast. It doesn't compound as quickly. Whereas equity just continues to grow, unimpaired by taxation, until you decide to sell it. It grows tax deferred, if you will, and compounds faster. ISOs and options are how, when you meet someone who's really wealthy and they work for a company, typically, they've made

• 20:19Scott Galloway?

  their money through options and exercising those options, getting equity in the company, and then at some point, selling it. Find out how much quote unquote they're worth. Go and type in ISO into AI or into Google and learn about it. Find the value on it as a percentage of your salary. And then if you're going to negotiate, and the best way to negotiate is to be transparent, I really want to work here, and say, and tell them, it sounds like you have three offers. I'd really like to come here. Is there any way we can increase the options package? I have never really saved a lot of money with current income. And I am wealthy because of the equity I have owned in companies. But let me just circle back to the beginning. So it's on you to learn what options are,

• 21:00Scott Galloway?

  the tax advantages, figure out what they're worth. And then if you can, negotiate a little bit more. And also, employers are really receptive to the notion that I don't want more current income. I want more options because I want to be an owner here, a bigger owner here. But this is the mother of all good opportunities. You should feel really good about yourself. You've studied hard. It sounds like you've got great certification. And you've got a good job offer. And this is absolutely, everybody wants to be you, young man. So congratulations and well done. That's all for this episode. If you'd like to submit a question, please email a voice recording to [email protected]. That's [email protected]. Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit, and we might feature it in an upcoming episode.

• 21:45Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Rieck is our social producer. Brad Williams is our editor. And Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.