Transcript, E212: Nicaila Matthews Okome on maximizing your side hustle

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Network ID:

LinkedIn News.

Jessi Hempel:

From the news team at LinkedIn, I'm Jessi Hempel, and this is Hello Monday. It's our show about the changing nature of work, and how that work is changing us.

I've always had a side hustle, I think it's pretty common. A lot of you do too. For me, it's usually involved writing, I get up early in the mornings to work on writing projects, or when I was at Wired, I used to take vacation days to moderate leadership retreats. Now, there are two big reasons for all this extra work for me at least. First, I kind of think of it as an insurance plan. If I get laid off, I'll have a source of income, and you know, hopefully people to call up. Now keep in mind, I came up in media, where layoffs they happen just about every year.

But there's another reason that's equally as important to me that I do this work on the side. It's critical for me that my work has meaning. Like, I don't think I could motivate myself to get up in the morning and do it without that. And I'm always trying to explore whether there's a different kind of work that might give me more meaning. A side hustle, well, it's a low stakes way to test the waters. Today's guest sums it up this way.

Nicaila Matthews Okome:

I side hustle to figure out if I really want to do something.

Jessi Hempel:

That's Nicaila Matthews Okome. Nicaila hosts the podcast Side Hustle Pro. It's a great show. It features tips, advice and interviews with Black women entrepreneurs who've transformed their own side hustles into impressive gigs. And Nicaila, well, she's a force herself. This show is her full-time gig now. But as you might guess, it didn't start out that way. And I think this is particularly valuable for listeners to note.

Nicaila didn't see herself as a kind of a risk-taker who had become an entrepreneur, though, that is what she has become. After college, she got her start working in PR at Nickelodeon. She got her MBA at the University of Michigan. She interned at Google, and she landed a choice position at a solid name brand company, NPR. These are the kinds of big name brands that suggests stability and radiate success. But all the while the Nicaila was testing out whether there was something more meaningful she could build.

Today's episode is for anyone out there with the side hustle or even thinking about it. Nicaila will talk about the kind of stability that comes from being one's own boss. She'll help us think about what types of projects might make good businesses versus hobbies or passions, and she'll cover how to put in smart hours rather than long hours. Here's Nicaila.

Nicaila Matthews Okome:

I like that you bring that up the allure of the big brand, because I think that's something I've been fighting in my whole life in terms of unlearning the need for validation. And it wasn't until I started to unlearn that I don't think we ever 100% step away from that in the society we live in. But the more I got more comfortable with letting go of that need for validation from having these big brands on my resume, and feeling like that made me who I am, or that made me smart, that made me qualified, the more I was able to embrace the side hustle path and what came from a very non-traditional career path that I now have.

Jessi Hempel:

Well, so your first side hustle, when was it?

Nicaila Matthews Okome:

My very first side hustle was actually when I was first out of college working at MTV Networks. In order to decide whether PR was indeed for me, I started a (laughs) "PR firm." It was called Nicaila KPR (laughs). And I was reaching out to my friends to be their publicists. Like all my friends who wanted to do things like be, uh, entertainer or whatever. I said, "Oh, I'll be your publicist." And that is truly what my goal has always been with side hustling, I side hustle to figure out if I really want to do something.

Jessi Hempel:

Mm.

Nicaila Matthews Okome:

And through doing that, I realized, "You know what? I don't see myself in PR. I don't see myself writing these press releases or doing all of these different type of tests." So that helped me and then I would say my next side hustle really was a blog and then ultimately, the podcast which became my full-time hustle.

Jessi Hempel:

You know, one thing in, in listening to your work, one big aha I had is-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

... I'm gonna tell you, I always thought of a side hustle as hack a lot of work you were doing on top of your job.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

And it is.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

More worse than your job flat out, right?

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

But one thing that you really opened my eyes to is that, um, we can work smartly rather than work hard.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

That it's not the amount of work that you do, but the strategy you apply to that work.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

Is that something you had to learn yourself?

Nicaila Matthews Okome:

Yeah, absolutely. It's something I had to learn. And as matter of fact, I think I am still learning that. But when... as it came... when it came time to side hustle while I was working at NPR, I realized I still wanted to do this blog, I still enjoyed this work. So okay, how was I gonna fit it in? And that's when I started to really look at my time and say, "All right, well, I could do an hour after work at least. And, okay, how can I get smarter about getting everything done? Okay, I'll have specific days when I do each thing."

So that's when I got into the system of batch processing things, assigning certain tasks to certain days. And my big thing was an hour a day, like, just give it an hour a day, you'll be surprised (laughs) how far you get. I like sleep personally. So I was never staying up till 2:00 AM, every night to work on my side hustle (laughs).

Jessi Hempel:

(laughs).

Nicaila Matthews Okome:

That just wasn't for me.

Jessi Hempel:

You say that, Nicaila, I, um, I... you... Well, you know this, I am a-

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

... podcast host here-

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

... on LinkedIn.

Nicaila Matthews Okome:

(laughs).

Jessi Hempel:

Over the last couple of years, I've had a pretty significant side hustle myself, I wrote a book.

Nicaila Matthews Okome:

Oh, very nice.

Jessi Hempel:

And when I sold the book, uh, I sold it before I wrote it, which meant that I was making a promise that I was going to be able to execute on this side hustle, to work my full-time job and somehow turn in the book. And what you say is what I discovered, which is it doesn't take 2:00 AM, mornings, it takes an hour a day.

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

And i- you would be surprised how much you can accomplish when you give it the consistency of the hour a day.

Nicaila Matthews Okome:

Oh, yeah.

Jessi Hempel:

I wanna go back to NPR a second. You walk into this huge legacy brand.

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

And it's a pretty great job out of business school.

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

Um, and yet you end up pursuing your side hustle, I'd love to understand a little bit about what your trajectory in your time was like there.

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

And where you got the confidence to decide to move beyond it to leave that legacy brand and invest in yourself.

Nicaila Matthews Okome:

So at the time, my mindset was, I will never put all my eggs in one basket again. And the reason I had that mindset is because of the difficulty I had, finding a role. I remember going through six rounds of interviews for Uber for, you know, they were just getting ready to launch Uber Eats. And I went through six rounds of interviews, I really thought I was gonna get it.

And that process left me so dejected, which I'm sure so many people can relate to. That's when I started to realize that I want something that's mine, that's for me, that no one can take away from me or say, "Hey, sorry, there was someone else who's better for the job, or sorry, you're no longer the best for the job. So you have to leave."

And so by the time I, I was fortunate enough to land that role at NPR, I was so invested in what I was doing on the side. That was what was lighted me up, like, "Okay, how can I make sure that I can still find time for this, while I'm working here?" Of course, I was excited to get to learn more about the organization and start my role and show and prove what Nicaila can do. But that's really where my mindset was at the time.

Jessi Hempel:

Yeah, that makes a lot of sense. And I think so many of our listeners will connect to that, and particularly in this climate, you know, we're, we're in the middle of 2023-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

... um, particularly in the tech industry, but actually across every industry there have been so many right-sizings and downsizing and-

Nicaila Matthews Okome:

Right.

Jessi Hempel:

... re-sizings and reorgs. And a lot of our listeners, regardless of whether they have lost their jobs have had to undergo a reorg that they hadn't planned and are feeling a little out of control.

Nicaila Matthews Okome:

Right.

Jessi Hempel:

And I think that the idea that you might be able to create your own opportunity is very appealing.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

I wanna start with everything that you have learned about the what. Some people come to this because they have a passion. I did. I was like, "I... My passion is writing. I just have to do that." A lot of people come to this because they're like, like you, "I wanna make sure that I have something that's mine alone."

PART 1 OF 4 ENDS [00:09:04]

Jessi Hempel:

Like you, I wanna make sure that I have something that's mine alone.

Nicaila Matthews Okome:

Yep.

Jessi Hempel:

Um, how do you identify then what the what is?

Nicaila Matthews Okome:

The what comes from experimentation. The what comes from freeing yourself from this thought that I'm just going to keep chugging along, and one day I'll have an aha moment and the what will come to me. So that's not actually how it works. How it works is testing out a few things, throwing things against the wall.

So I always recommend that people start with just identifying what are some of the things that you enjoy doing. And you're gonna start really broad. I mean, it could be I love cooking, I love baking, I love reading, even. You might not know where that could take you, but you might one day be the host of an amazing book-focused podcast that just attracts all these amazing guests and sponsors. You never know.

And of course, then from there, you go, what would you want to do (laughs) outside of work when you're not getting paid for it yet? And that's when you're able to narrow down things, because if you enjoy cooking for yourself, it's a act of just release, and there's no pressure to it. The idea of cooking and catering for others for money on their timeline may not be what you wanna do for a side hustle, because that might suck the joy out of it. Um, even though there're things I didn't turn into my side hustle, I still explored. I took photography classes. I've taken acting classes. I have explored, and that's how I was truly able to narrow down.

Jessi Hempel:

Did you have any sort of practice, like, journaling or morning pages or taking notes or working with a coach?

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

How did you study yourself?

Nicaila Matthews Okome:

I did start to study others. So I identified people who were further along on any path that I was interested in exploring. So when I was interested in exploring blogging again, I took courses from people like Amy Porterfield, who, you know, if you don't know Amy, she has a podcast as well, and taught me about email marketing, social media marketing, and things of that nature. So I consider myself a lifelong learner, and it can be easy, especially when you are educated, to think, oh, I have this degree so I don't wanna look like I don't know anything. After a while, like, everyone's degrees are outdated. Like, we just don't do business the same way. So if I was to walk around like, "Hey, I have this degree, that means I'm a expert at business," I would be doing myself a disservice, because I went to school at a time when TikTok didn't exist, okay? (laughs)

Jessi Hempel:

(laughs)

Nicaila Matthews Okome:

Like, I need to know how to do business on TikTok.

Jessi Hempel:

Yeah.

Nicaila Matthews Okome:

And so that means I need to go out there and take a course. So I'm very big on taking courses. One at a time, though, so you can really focus on the content, implement the homework, test things out. Don't go out and buy a bunch at the same time, because you're less likely to actually complete them.

Jessi Hempel:

I love that you used the TikTok example, because I know I was listening to you in one conversation talking about a recent conversation, talking about how TikTok was not your platform but you decided to learn what you could do with it anyhow.

Nicaila Matthews Okome:

Yes. Yep.

Jessi Hempel:

And what I liked about this conversation is that you talked about what you learned you could do with it anyhow, but you still seem to have a radical focus. You will were very clear, like, you learned how to do this thing, and your platform, you said at the time, was Instagram. How do you figure out how much of your energy goes to the new thing, and how much of your energy goes to what you know works?

Nicaila Matthews Okome:

You use the exact word that... The term is so much. Energy (laughs). We, we only have so much energy in the day, and what I have learned is it's okay to have real estate on different platforms, specifically when it comes to social media marketing because that's who I am at my core, but your audience is not necessarily on all of these platforms. So it starts with really honing in on where is your core audience, who's the core person for your side hustle, and where are you going to reach them most regularly.

And for me, from Side Hustle Pro, I should say, the podcast, it's Instagram. Now, TikTok is creeping up there, and that's why I had to, I had to get going on it, but I will only do so at a pace that works for me.

Jessi Hempel:

So as you were first starting to build the business...

Nicaila Matthews Okome:

Right.

Jessi Hempel:

... what did you land on as your idea for what the mission of the business is?

Nicaila Matthews Okome:

Side Hustle Pro is really, it really focuses and highlights on Black women entrepreneurs who started as side hustlers and scaled to full-time entrepreneurs. Why? Because at the time, I found myself in this place where I didn't yet have a job and I was seriously contemplating starting my own boutique marketing, social media marketing agency, but I was afraid. I just had this false belief that I'm not a entrepreneur. It's not for me. I had this belief that you had to be this risk-taker who doesn't care about money, who doesn't care about anything other than just getting the business off the ground. And I wasn't seeing stories of people whose... liked a safety net (laughs) and wanted to have money, that, you know, so they could have discretionary purchases and still enjoy life while building that business. And it was important to me to see that myself. As cliché as it sounds, that saying of you can't be what you can't see is completely accurate, and I didn't see it out there, so I knew I had to create it.

Jessi Hempel:

So I wanna go back to the point at which you thought, "Well, gosh, I'm not an entrepreneur," because, uh, that, that never crossed my mind, um, and it's important to note that, that as I look back on your career, all I can see is the huge leaps that you took, and I can't see the places where you chose to build up the safety net in order to take that leap...

Nicaila Matthews Okome:

(laughs) Yeah.

Jessi Hempel:

... or mitigate risk in a thousand different ways. And it is reassuring to me to hear that maybe you, like me, want to know that you have a college savings fund for the children-

Nicaila Matthews Okome:

Right, right.

Jessi Hempel:

... before you go off and do a big thing.

Nicaila Matthews Okome:

Yep.

Jessi Hempel:

Is there a reason that that is perhaps more specific to Black women entrepreneurs?

Nicaila Matthews Okome:

It's funny that you say that, because you're not the only one who thinks that. And that's why it's important to also sometimes just take inventory, reach out to your friends, and ask them how they see you, because I learned (laughs) through one of those kind of surveys that I sent to my friends that people saw me as someone who did take risks. And I didn't see that myself. I take calculated risks, so everything, despite what it may look like on the outside, was always kind of thought through and planned out.

I absolutely think that this idea of mitigating risk and needing to have some sense of security is an experience that many other Black women go through as well. I can only speak to what I've experienced, but I absolutely think that there's this sense that you want to be perceived a certain way. You feel that you need to have all your ducks in a row, and you need to be able to know where your next cheque is coming from. So the idea of just leaping out there, moving to Silicon Valley, living with a bunch of bros, and, you know, wearing a black t-shirt every day, first of all, it, it just does not apply to us (laughs).

Jessi Hempel:

Yeah.

Nicaila Matthews Okome:

We're not doing that.

Jessi Hempel:

So true.

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

Yeah, I remember having, um, a wonderful, uh, founder on the show, a women named Aicha Evans, who-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

... uh, is a Black woman who, in the middle of her career, um, had become the CEO of this incredible autonomous vehicle company-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

... and she walked me through the early part of her career. And it was so inspiring, but it was so straightforward and corporate.

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

And she said, "Oh, this was by design."

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

"Because now it lays me the foundation to be able to take this bigger risk."

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

And that made a lot of sense, um, and, yes, it runs counter to the trend of, um, white young man moves to Silicon Valley-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

... starts Facebook-

Nicaila Matthews Okome:

Right.

Jessi Hempel:

... that became so popular to emulate over the last 15 years or so.

Nicaila Matthews Okome:

Yes. And, and I should also mention, you know, I think a lot of our businesses are going to be self-funded. We need to be our first investor. You know the numbers. I don't have to put them all out there, but you know how harder it is for Black women to get investors. It's a long road. In addition, if you choose to just go a family-and-friends round, the funds that may come from our network will be different than what will come from another network. So there's a huge emphasis on, how much of this can I pay for myself until it gets going?

Jessi Hempel:

We're gonna take a quick break. When we come back, more on side hustles with Nicaila Matthews Okome.

And we're back.

PART 2 OF 4 ENDS [00:18:04]

Jessi Hempel:

And we're back. Nicaila has walked us through managing her side hustles against her day jobs, but often there comes a point when a side hustle gets big enough that you really just have to make some decisions. Are you gonna keep takings the kinda of risks we touched on before the break? Do you wanna hire someone to help you forge ahead? Where does it go from here? Here's the story of Nicaila's turning point.

Nicaila Matthews Okome:

One of the pivotal moments for me was when I decided to start monetizing, meaning I needed to learn as much as possible about what went into the podcast monetization side of the business. And of course I had a peek into it at MPR, but these are podcasts that are at a completely different scale than I was. You know, they're doing millions of dollars per month, I'm doing thousands. So, I sought out resources to help me, and I found a class... Um, it was a two-day, sponsorship intensive about events. So it wasn't podcast specific, but I thought, "okay, if I at least learn how to pitch sponsors, I'm sure I can tweak and apply, and learn as I go about how they do it in th- the podcast world."

So that's what I did, and it was my first... It was my largest investment at the time. It was $1097, and I just remember talking it over with my husband like, "ugh, do you think this is gonna be worth it?" (laughs). And I do what I... I now tell people my w... Will it be worth it if equation and, to me I was like, "okay, it will be worth it if I book a sponsor for the same amount, then I'll make my money back." So that was my initial goal. I was like, "I- I... I really think I can do that" okay?

So I ended up doing that course. From there, starting to cold pitch sponsors, and landed my first $4,000 about six months into podcasting, so-

Jessi Hempel:

So you got your money back in about 3X-

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

On the first five.

Nicaila Matthews Okome:

3X times my... My money, and that's when I decided to make my first hire. So I... My first hire was an editor to take the editing off my plate. So my investments in my business have been slower, and I've always tried to have an asset that can pay for it. So I'm not going into debt for the business. So I am able to still reap a profit (laughs) from the business, and also pay my team.

Jessi Hempel:

Can you talk to me about a mistake that you feel that you have made, and how you've addressed it?

Nicaila Matthews Okome:

Hm, it's one that I'm still working through. It's really being so slow to outsource, and it's having that "I can do it the best" mentality, which only slows down your business. Ultimately, no business owner should put themselves in a situation where they are the bottleneck, or they are... Their business can't run without them. And so that's something that I am constantly trying to figure out. How do I get better at that? How do I get better at hiring? And so that I can completely let go of this. And it's... Each year I get better. Just the other day there was something so simple, like looking over the show notes. I've always done that, even though I don't need to anymore, you know?

A- and just the other day, I just said, "I- I don't need to look at it." That little thing, I feel so free. So it's just finding those ways to just let go of more, and-

Jessi Hempel:

A- and you... You don't need to anymore, Nicaila-

Nicaila Matthews Okome:

(laughs).

Jessi Hempel:

Because now you have somebody as part of the team who would do that, right?

Nicaila Matthews Okome:

Right, right, right.

Jessi Hempel:

Yeah. I mean, I've gotta say, I'm nodding. I know that somewhere behind the scenes, our producer is nodding.

Nicaila Matthews Okome:

(laughs).

Jessi Hempel:

Nodding for everybody that takes pride in work well done-

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

And takes pride in their own work in particular.

Nicaila Matthews Okome:

Right.

Jessi Hempel:

This idea of letting others do the parts that you don't need to uniquely do is a powerful idea. So as you started the show and as you've grown the show-

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

You've ended up talking to so many entrepreneurs.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

Would you say that there's a- a characteristic that defines successful entrepreneurs?

Nicaila Matthews Okome:

When I think about everyone that I've spoken to, the key trait is confidence. The key trait is confidence. You have to have this level of belief in yourself, and also willingness to fail, or fall on your face and have people see it, and understand that it doesn't matter, because you're braver than them because you are willing to do that, and they're not. The people who are laughing at you are not brave enough to do what you're doing. So the first step is confidence, and I understand there is always the concern of, "what will my job say?" Right? That's one of the key things that people will say to me, and try to use it as an excuse.

But, you can't be the one to tell yourself "no". That's actually a piece of advice that someone gave me when I was a little nervous about starting the podcast, working at MPR. I thought, "oh, uh, how are they gonna look at that?" And she told me, "don't tell yourself 'no', wait for them to tell you 'no'." And so I pass on that advice as well. Um, so a lot of us are masking a lack of confidence with these fears that we let hold us back, and when no one has told us "no" yet, we just are telling ourselves "no".

Jessi Hempel:

So what happens when you don't do that, I think about my own career, and early on in my career I wanted to write a book. And I asked permission of my... My magazine that I was employed for. I said, "could I have book leave?" And they said, "no. We're really busy in the fall. No." Okay, end of that. And I remember talking to a colleague, um, who was a white guy, and I think this was part of it. And he said, "well how did you ask?"

Nicaila Matthews Okome:

(laughs).

Jessi Hempel:

I said-

Nicaila Matthews Okome:

What do you mean?

Jessi Hempel:

"Well, can I... Can I take book leave?"

Nicaila Matthews Okome:

Yeah.

Jessi Hempel:

And he said, "oh no, no, no, no. That's not how you do it." He said, "you've already told yourself 'no' in your head and you're just waiting for them to say 'no' to you."

Nicaila Matthews Okome:

Wow.

Jessi Hempel:

He said, "when I go and ask for book leave, I say 'hey I've sold a book, I'll need September and October. I'll probably be back for November. Does that work?'"

Nicaila Matthews Okome:

Wow.

Jessi Hempel:

And they don't say no to him, Nicaila.

Nicaila Matthews Okome:

Wow, I love that. That's so true.

Jessi Hempel:

And it's subtle. It's a subtle shift in language that reflects the expectation that he has versus the one that I have.

Nicaila Matthews Okome:

I absolutely agree with that. I did make that shift later on in my career in terms of how I ask for paid time off. I, too would say, "hey, I'm going here, and I'm going to need these days." Or, "I'm going to be going here the first week of August," rather than, "can I go?" That shift in language completely does change the conversation.

Jessi Hempel:

Yeah. Nicaila, what are the other things that come up from your listeners? So many of your listeners are listening because they have side hustles they wanna get off the ground. What are the questions they bring to you?

Nicaila Matthews Okome:

There's sometimes controversy around, "you don't need to monetize every gift," and no one's telling you to monetize every gift, however, if there's something you like to do on the side and you find yourself getting customers, getting inquiries, you absolutely should start to charge for your time, and charge for your work. Monetization gets a bad rep. There is a lot of guilt around asking people for money for your work and your time, and that goes back to corporate as well, and asking for raises and asking for what we deserve. And this is an exercise that we all need to do. This is something that we all need to learn.

Jessi Hempel:

I think you hit at the heart of something, which is, we've got a lot of baggage when we think about this thing that I have uniquely that is so valuable, that I may not even ascribe value to it. It's okay to ascribe value to it, and to profit off of it.

Nicaila Matthews Okome:

Yes.

Jessi Hempel:

I mean, it makes me uncomfortable to even say it.

Nicaila Matthews Okome:

Mm-hmm.

Jessi Hempel:

Wh- where is the discomfort there?

Nicaila Matthews Okome:

I think it goes back to gender roles and this idea that I... Women should just enjoy doing a lot of work for free (laughs).

Jessi Hempel:

(laughs).

Nicaila Matthews Okome:

That because we are so nurturing and giving, this should just be something that we love to do, and how dare us want to get paid for our time and our services and our worth? I hope everyone listening will take some time to really ask yourself those questions. "Why do I feel icky around making money off of this thing that people always want from me?" Or, "why do I feel weird putting myself out there, and why do I have a feeling of, who am I to do this? I see other people doing it, but when I envision myself doing that, I think oh, everyone's gonna say, 'who does she think she is?'"...

PART 3 OF 4 ENDS [00:27:04]

Nicaila Matthews Okome:

... envision myself doing that, I think, oh, everyone's gonna say, "Who does she think she is? Oh, she's an influencer now?" You know, like, these are thoughts that creep into your mind and you allow them to sit there and you don't challenge them. So if there's anything I want you to do after this episode is to challenge the automatic thoughts that pop into your mind when you consider side hustles.

Jessi Hempel:

Well put. And of course now your side hustle is your full-time gig, Nicaila.

Nicaila Matthews Okome:

Oh, yeah. Yeah, yeah.

Jessi Hempel:

Wonderful. Well thank you Nicaila for coming on the show. We really appreciated your perspective.

Nicaila Matthews Okome:

Thank you so much for having me.

Jessi Hempel:

And our listeners, particularly our listeners who are interested in side hustles, need to be listening to your show.

Nicaila Matthews Okome:

Yes. Come on over, side hustle pro.

Jessi Hempel:

That was Nicaila Matthews Okome, the host of Side Hustle Pro. Her show has some great advice. This week on Office Hours we're gonna talk about our own side hustles. What is it for you? How do you make it work with your day job and what's your big plan with it? What are you gonna do? Join us for Hello, Monday Office Hours this Wednesday at 3:00 PM Eastern, live at the LinkedIn news page. If you have trouble finding us, send us an email to [email protected] and we'll send you a direct link. We're gonna talk all about it. You can also continue the conversation in our Hello Monday group on LinkedIn. To join, click right from the show notes.

And now it's time for another book recommendation. This week, we're bringing back Scott Ulster. Hey, Scott. Great to have you in the studio. How you doing?

Scott Olster:

Hey, Jessie. Good to be here. How are you?

Jessi Hempel:

Uh, I've been doing well. I've been getting more time for reading lately, I'm reading some great stuff.

Scott Olster:

You have. What have you been reading?

Jessi Hempel:

I just got last night the copy of Maggie Smith's new memoir.

Scott Olster:

Nice.

Jessi Hempel:

Yeah, she's a poet that I have always loved and here's why I like this memoir, Scott, I know it's you recommending books, not me, but let me tell you.

Scott Olster:

No, please.

Jessi Hempel:

Here's why, because it does appear to me that all the chapters are one page long.

Scott Olster:

(laughs)

Jessi Hempel:

And I can always read one page.

Scott Olster:

Yeah, that's, like, my favorite kind of book.

Jessi Hempel:

I know. Well listen, so what is at the top of your pile right now?

Scott Olster:

Yeah, right now I am reading a book called Generations by Jean Twenge. She's put together a book that summarizes what has happened, uh, to various generations, uh, throughout the 20th century. Uh, and she basically goes generation by generation using just this incredible wealth of data, exploring how, uh, different sort of historical moments and of course the evolution of different types of technology have changed how different generations experience life in the United States.

Jessi Hempel:

You know, Scott, so many people try to take a big swing at coming up with sweeping pronouncements around a generation but I think the thing that appealed to me about this book when you brought it to us was that Jean's work is so rich in research and history. I mean, she really is the foremost expert on this stuff, right?

Scott Olster:

Exactly. And the way she approaches the book is actually quite different than what you might experience when people talk about generations and the difference between this kind of group and that kind of group. And a lot of it comes down to the sort of data that she digs into. The book is just filled with an incredible amount of research on, uh, different, uh, generations' experiences.

Jessi Hempel:

So what are the major take aways that are relevant to the Hello Monday audience?

Scott Olster:

Yeah, so one of the big things she discussed about how generations have evolved and how their experiences changed, comes down to a few different key forces. And one of those things is just individualism. The idea that as, uh, different kinds of technology becomes available, we as a society and in particular generation after generation has become more, uh, of a fan of this idea of an individualistic life. A life that is defined on our own terms. Individualism on it's own isn't necessarily good or bad but it does come with consequences and one of those consequences is, on a brighter note, is the fact that generation after generation, those that have come after, are much more accepting of people, uh, who come from different backgrounds. And that kind of identity can come in several different forms. So we could talk about being more accepting of folks based on their gender, based on their race, based on their sexual orientation. So that's one side of the spectrum.

Jessi Hempel:

However.

Scott Olster:

Yeah, it's coming. So the other side is, as, as you embrace individualism, the things that bring us together, they can weaken. And there are a lot of forces that are driving this, most notably technology, according to Twenge. But we have seen that more and more people are feeling isolated. And in particular what she notices and what she points out is that we're seeing among millennials, and Gen Z in particular, we're seeing really really profound upticks in depression, in feelings of loneliness, and what she describes as, I- it's a common term now, unfortunately, depths of despair.

Jessi Hempel:

Is her book prescriptive at all? Does she give a, a path forward, a, a thing to do or think about?

Scott Olster:

She thinks it's time that we begin to have a very serious and open conversation about how we embrace technology and whether it's time to renegotiate our relationship with different kinds of tech.

Jessi Hempel:

Hey, so what's one tiny detail from this book that sticks with you, Scott?

Scott Olster:

Yeah, so one of the fun things that Jean does is she talks about how different stereotypes or generalizations we have about generations are just not on point. And I would say she really takes a, a hard swing at this dynamic between millennials and boomers where millennials often lay a lot of the, uh, blame for their perceived economic troubles at the feet of the boomers. That, you know, you, you happen to have a lot of fortune and great opportunity and we don't have that anymore and you, you, speaking to boomers, you could've done better for us.

And what she shows is that, in fact, a lot of the economic factors that millennials, um, are experiencing, 100%, a lot of these, these things that they're experiencing, it didn't begin with the boomers choices. The boomers themselves were dealing with it. The economy began to change, uh, certain kinds of work, let's say work that didn't require a four year degree, those jobs began to disappear well before the boomers reached their full age. So they, they have been dealing with these issues as well and if anything, um, they, they inherited these problems in the same way that millennials did.

Jessi Hempel:

Well thank you Scott. That book, again, is by Jean Twenge and the book is called Generations. It, just from looking at it, it looks like quite a thick read and you have turned down enough pages for us to know that you have done a great deed in reading it for us, thank you.

Scott Olster:

You got it.

Jessi Hempel:

Hello Monday is a production of LinkedIn News. Sarah Storm produces our show. It's engineered and mixed by Assaf Gidron. Our theme music was composed just for us by the mysterious Great Master Cylinder. Rafa Pherrea, Lolia Briggs, Lallas Tuesdale, Kanyah Rogers, and Michaela Greer help us hone our career visions. Enrique Montovo is our executive producer, Dave Pond is head of news production, Courtney Coupe is head of original programming. Dan Roth is the editor and chief of LinkedIn. I'm Jessi Hempel, we'll be back next Monday. Thanks for listening.

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