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

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

The Prof G Pod with Scott Galloway

August 31, 2026

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.
Speakers: Scott Galloway, Temi Dentonhurst

Topics: Entrepreneurship, Business, Careers

**Scott Galloway** (0:00)
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**SPEAKER_2** (0:39)
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**SPEAKER_3** (1:20)
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**Scott Galloway** (1:56)
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, who cannot yet retire, convince companies to take a chance on us? Yeah. So the way you're feeling is real. There's some data here. The job stability and the disruption is being felt by people, I would say older mid career. A major 2018 study found that more than half of workers in the 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 percent 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 and 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 Prof 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 percent above market, but no one thinks they're overpaid. They just say, oh, okay, I won't leave. 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 percent of the time in your career, you were overpaid and 50 percent, you were underpaid and almost zero percent of the time was 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? 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 going to 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 out and have dinner or not play golf but socialize with ad buyers or brands. I see them as we talk 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. A 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, boss, if you're in your 50s, it doesn't matter if you're 50s or 20s, the advice we would give you 22 year old self, you got to make a bunch of calls, you got to get out a big spoon and eat shit, call people you don't want to call, 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 intent, I go up and I start trying to, I need to do a better job of this, identify 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.

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