Office Hour’s Best of Career Advice
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Welcome to the second episode of the PropGPod special series featuring some of our favorite Office Hours moments. In last week's episode, we featured Office Hours best of business and answered your questions surrounding the brand era, big tech companies, and their ethical responsibility, and when a founder CEO should step down.

Advertising is a weird industry. It's always like one and a half percent of GDP. It doesn't go below that. It doesn't go above it. So this is not a growth industry. But you have some companies that are going 20 and 25 percent a year, which means they are sucking the oxygen out of the room for the other folks. Corporate America, these are platforms for making profits. And at the end of the day, they are going to do whatever increases their profits full stop. That's just what they do. You should assume if you're the CEO, you are not Bill Gates. You should assume you are not Steve Jobs.

Today, you'll hear best of career advice, including how to ask for promotion at work, when and if you should ditch your full-time job for your side hustle, and when to quit your job entirely. So with that, first question. Hi, Pravji. Now let me introduce myself. My name is Kareem, and I am from Toronto, Canada. I work in a marketing team at a pharmaceutical company, and I've been enjoying what I do. I've had a very exciting journey since

to get to where I am right now. And I've been in my current role for about a year and I've had something on my mind for the past few months, which brings me to a big question. Is it the right time for me to ask or maybe even bring up the topic of possibly getting a raise or a promotion?

I've been thinking about this for a long time and I can't help but wonder whether it should be me to bring it up or should I just hang in tight until they share with me the good news. Thank you so much for all what you do and I'm looking forward to hearing your thoughts. Karim from Toronto, thanks for the question and congrats on living in such a wonderful city.

It's unusual and not a great indicator or a great reflection on your company that you don't know when they announce promotions and raises. Because most firms, once they get beyond a certain size, say, you know, at the end of the year or in June of every year, we sit people down and we talk about compensation, which is usually bonuses, salary increases, or promotions, and/or none of the above, right?

and do a review all at the same time. This is a big part of what I've done at all my companies. When someone does something especially good or not so great, I do an email or the file about this person at the end of the year. I try to be very thoughtful about their compensation, their role, their title, all that good stuff.

And if anybody comes to me off cycle and asks for a raise or promotion, I say, "We don't do that. There's only one time during the year we consider this, and that is in December." And the fact that you don't know when that time is, is sort of strange. What I would suggest is the following, is that you find out when and where you hear about compensation and salary increases.

And that you establish a relationship with a mentor or your boss such that it's informal enough such you could say, you know, what should my, you can ask very straightforward, what should my expectations be around a bonus or how are bonuses evaluated? What about promotions?

you should just have more insight. I think it's okay to seek your boss or a mentor to launch and say, "I would like to be promoted and I'd love your advice on what I need to do to increase the likelihood I get promoted. I think that people like ambitious people."

Yeah, it depends. You can kind of read the tea leaves. Is the company growing quickly? Are you well-liked there? Are you generating revenue? A manager's job is to manage expectations, and then ideally, if they can, I don't want to say exceed those expectations. I always work for growth firms.

A few of those firms have done really well, so we were in a position to kind of surprise and delight people. Sometimes in a big company, it's not growing that fast. If a company is only growing 2% a year, it's hard for them to give out 4% raises even because that means they're going to have to reduce their profits or if their profits themselves aren't growing faster than 4% a year. What you don't want to do is set up a win-lose situation where they're looking for excuses not to give you a raise or a salary.

So it's be a good citizen, don't bring it up more than once a year, be grateful, don't be bummed out. And if you really think they're screwing you over, start looking for another job. But I find as someone who manages a lot of people's expectations when they're constantly pushing me for raises and promotions, I find that I naturally want to not do it, that I have a gag reflex on it. And there's certain people in my organization that just work really hard.

and I want to surprise and delight them. Some people would argue it's the squeaky wheel that gets the grease. That has not been my experience. But boss, you need a mentor here or a relationship with your boss so she can start having these conversations and find out when is the

When is the compensation window? And get advice on what you should be doing to reach your goals. Thanks for the question. Question number two. Hey, Scott. Ryan from Philadelphia here. Love the podcast. Spotify told me I was in the top 2% of your listeners. So objectively, I'm one of your biggest fans. Here's the question. I've been working at a large consulting firm in cybersecurity for the past 10 plus years.

while also leading and running multiple tech startups, some of them more successful than others, but obviously they're still a side hustle. As I apply to new roles within my organization and even outside, I'm torn whether I highlight those experiences in startups or not. Will it hurt me? Will it make my chances stronger? Ryan from Philadelphia, 2% bitch, commit. Why are you in the top 1%? To resist this feudal, give him to the dog. That's right, be a 1%-er.

That's a scary thought. Anyways, thanks for your listenership. Let's talk a little bit about Philadelphia. I had never really spent any time in Philadelphia, and then I went on the board of Urban Outfitters, a very interesting two of the top brands, according to millennials, are Urban Outfitters and Free People, both owned by Urban Outfitters. Think about that. One company owns two of the 10 hottest brands.

among millennials. Also, they have the coolest HQ of any company I've ever been to. They took over the Navy Yard or they have their HQ at the Navy Yard in Philadelphia. So you'll be in a conference room talking about quarterly financials and you'll see this old aircraft carrier bobbing up and down. Anyway, smart people will enjoy my four years there. I would not describe Philadelphia as kind of the old Navy of cities, sort of 60 or 80% of New York for 40 to 60% of the price. Seemed like a good quality of life at a lower cost of living. Anyways, Philadelphia, there you go.

Okay, what was your question? Oh, whether or not you, when applying for internal roles, talk about your side hustles. This is situational. I can only tell you how I would respond. And that is, as your boss, I don't think I'd respond well. And I'd be like, Ryan, if you want a promotion, here's an idea. Focus on this fucking job, boss. So I don't...

I can tell you that I get having side hustles. Actually, I don't get having side hustles. Let me cut to the chase, Ryan. I think your side hustle needs to be your main hustle. I think you need to have one hustle. So do the hustle, but do one fucking hustle. And that is, if you want economic security, find something that satisfies you to the extent that you don't feel the need to do a side hustle and go all in on it. I mean, the idea, I think the reason I'm

Well, one of the reasons I'm economically secure, probably the primary reason I'm economically secure is I was born at the right place at the right time. But in terms of my economic security coming from my professional success, it was focus. And that is I went all in, Ryan. I went all in. I was in the office on weekends, returning emails immediately.

If you're at a small organization or a place where people are looking to develop economic security, the way you develop economic security is by garnering an unfair share of that market and getting more economic currency than your peer group, right? I mean, the average wage globally is, I think, about $18,000 a year. So if you want more than that, you got to be in an economy and you got to bring more productivity. And part of that is just pure elbow grease and focus, right?

So I've never understood the idea of a side hustle. I get it if you're at a big company and they're paying you well and you want to stay there, but okay, if you're going to have a side hustle, have it for a while and then it either takes off and you go all in on it or give it up and go all in on your company. Because my guess is the fastest blue line path to economic security at your current job would be to be great at it or specifically greater as in focus more on it. So my advice to anybody who has a side hustle is if

has put a time limit on it. And if the side hustle begins to grow, then quit your current job and go all in on your side hustle. But the way to economic security, the way to success, the way to professional currency, in my view, is 110% focus on one thing. Thanks for the question. We have one quick break before our final question. Stay with us. Your business deploys AI pilots everywhere. But are they going anywhere? Or are they stuck in silos, exhausting resources, unable to scale?

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Welcome back. Question number three. Hey, Scott. Love the show and appreciate all the help and guidance you bestow upon the masses. My name's Robert. I'm 30 and living in Los Angeles, and I've been working in investment banking since leaving grad school, about 10 years. Thus far, I've made a good living with this career, but as of late, gotten to the point of complete disillusionment with where the field ultimately takes you. Among the many red flags, most of the higher-ups of the firm were alcoholics and or divorced, and seemed to just be supporting an expensive, lavish lifestyle without size pay.

While I understand this is a privilege problem, I'm about to cut the cord and quit in the near future. I envision my next chapter being one to two years playing the tourist visa game, working odd jobs around the world, and figuring out what my next chapter in life is going to be. While I have enough saved to support many months on the road, I do plan to look for professional and investment opportunities throughout the Odyssey. Any advice you'd send my way prior to embarking? First off, I feel you.

Jobs typically bifurcate into one of two things. They're either very stressful, but very interesting and rewarding, or they're very, very non-stressful, but boring and not that intellectually stimulating. I found investment banking to be this unique combination of an incredibly boring subject matter with a shit ton of pressure placed on it. And I spent a lot of my life at the printer. We actually printed a

prospectuses or S1s for public offerings. And my job was to go through this fucking prospectus, this 80-page prospectus, read it frontwards and backwards to find errors, to make sure the base rental payment on page 33 wasn't base rental payments on page 81. And if I missed anything and there was a typo, I could no joke, there was a good chance I'd be fired the next day. So I'd be up till four in the goddamn morning proofing a prospectus. It was just...

I thought I was gonna be doing deals on the Concorde and hanging out with interesting people. Instead, I worked with a bunch of abusive assholes and they were assholes. And it was just incredibly boring work. Now, having said that,

It was a fantastic training because work is hard, taught me attention to detail, taught me how to manage people with big egos. But everyone in my firm, not everyone, the majority of the senior people, not happy, would rather be doing something else, but had gotten to the point where they built a lifestyle where they needed to clock their half a million, million, two million dollars a year in investment banking,

and could either go be the CFO of a company and take a 60% pay cut or go try and start a business, and none of them were really entrepreneurs at heart. So they were kind of all trapped, if you will. Now, there's some, a small subset of them that really enjoyed it, but I literally think for most of them, the term work was the appropriate term. Anyway, the fact you're getting out and you're pulling the ripcord, good for you. Having said that, I wouldn't take too much time on the road. As a matter of fact, and it may be too late for this,

You know, Bas, it's so much easier to find a job with a job. Is there any way you could find a job or try and figure out what you want to do next, whether it's a startup and then...

And then take your three-month sojourn. I know I'm sounding like your dad right now, but you're just a used car. You're not as attractive when you're interviewing and you don't have a job. There's no sense of urgency. In addition, my experience with people who kind of go to touch Indians and, you know, practice yoga or whatever it is you're going to do or hang out with llamas in Argentina. Do people do that? Is that a thing?

I don't think you're going to have this epiphany of what you were meant to do. Maybe, maybe. I think most people who do that kind of stuff, when they have an epiphany, it's that they should return to the religious roots or get more involved in nonprofit, but they usually don't. They usually don't think, oh, I should really be in healthcare maintenance software or something. I don't know if that's going to happen on the road.

So look, I don't know enough about what your skill set is. If you're at an investment bank and you've done well, you're good in services, so that lends itself really well to consulting. You have an understanding of finance, so that lends itself to operations or to be the CFO or in finance. But my suggestion is at your age, I would go where you think you have some interest, where you think you can leverage your investment banking skills.

and an industry that's growing. Having said that, it means I don't know. I would need to know more about you, my brother. What I would suggest though, is that you begin to make those inquiries sooner rather than later. And just so I can play dad for a moment, time's gonna go really fast. And what you don't wanna be is wake up a year, two years later, and you let perfect be the enemy of good, and you didn't take any offers, you didn't chase anything down.

and you start to smell. What do I mean by that? Once you're out of the job market for longer than a year, you begin to smell. And I know how terrible that sounds now, as people are like, "What is wrong?" And your skills begin to atrophy. So I would be making as many contacts as possible, having coffees, following up with people, get an idea of what you want to do, have a plan maybe, and then take off. But anyways, you're obviously a very talented guy. Investment banking, I found, paid off for the rest of my life in terms of the skills and the discipline.

and attention to detail. It taught me, even if you don't like it. And I also think if you don't love it or you don't have to have the money, I think you're smart to get out. It is, in my opinion, a fairly soul-crushing, non-redeeming way to make a living. Too much? Too much? Thanks for the question. That's all for this episode. If you'd like to submit a question, please email a voice recording to officehoursatpropertymedia.com. Again, that's officehoursatpropertymedia.com.

And we're back with Canva Presents Secret Sounds, Work Edition. Caller, guess this sound. Mouse click. So close. That's actually publishing a website with Canva Docs. Next caller.

Definitely a mouse click. Nice try. It was sorting 100 sticky notes with a Canva whiteboard. We also would have accepted resizing a Canva video into 10 different sizes. What? No way. Yes way. One click can go a long way. Love your work at Canva.com.