Ep 43 - Is Freelancing Worth It in 2025? The AI Impact on Your Career Options

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Ep 43 - Is Freelancing Worth It in 2025? The AI Impact on Your Career Options Podcast and Video Transcript

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Dave Dougherty: Welcome to the latest episode of Enterprising Minds. Dave and Alex are here for you. Alex, you have today's topic, so why don't you

Alex Pokorny: start us off? Yeah, it's something that's been on my mind, but also something I've been hearing from some folks off of LinkedIn is they're thinking about going freelance.

The Pros and Cons of Going Freelance

Alex Pokorny: So, What is your opinion of going freelance in, say, late 2024, early 2025 kind of timeframe? Do you think it's a good idea, especially in the world of like, SEO is kind of unknown with the advent of AI pieces and how that's going to be affecting SEO? Content creation and AI kind of option there or view of it being a really good option?

Is that a smart choice to go right now? Or what angle or spin would you put on it to try to make it into something that would work? Wow. Okay. Yeah.

Dave Dougherty: There's a lot there.

Alex Pokorny: Let's break it down right now. Would you go free?

Dave Dougherty: Would I go freelance? I was just about to caveat what I was going to say by I'm not necessarily in a position to consider this choice for myself right now. God forbid, you know, maybe I'm forced to make the choice. Who knows? Right. Can't do, can't look, do any future looking things.

No, I think. If you would have asked, let me put it this way.

Impact of AI on Freelance Work

Dave Dougherty: If you would have asked me a couple of years ago, I would have been way more bullish on ongoing freelance with how much AI has changed and how much the AI capabilities have increased, you know, holding aside all the debates of like whether or not it's good and hallucinations and whatever else what they are still doing is still amazing.

I would be a little more nervous about it now from a pure financial, like I can sustain myself kind of standpoint. Sure. Unless you have like the really big client that's like already lined up, you know but I don't think the environment is really nice to agencies or freelancers right now. Yeah. How about you?

Where are you sitting on on this before we get stuck in on whatever, you know,

Alex Pokorny: kind of all over the place. To be honest, I don't really have a firm opinion right now. Part of it is. I absolutely agree. AI is putting a giant question mark on projects. So, if you're a marketer, or a small business, or a large business, and you're trying to put together, like, what should we do with this whole SEO thing, because we don't know what we're doing, if you're at that point, and you're trying to put together some budget, you would say, I don't know where it's supposed to go right now.

It feels a little weird. It's not just like in prior years, you'd hire an SEO consultant, they would do the recommendations and whatever else. And said, now I'm a question of, I need more of a guide to help me make that decision. And maybe that becomes a sales opportunity as you become. Kind of a strategy consultant who's giving away time probably for free at the beginning to say here I can help you kind of guide you in this uncertain time right now Which will eventually probably turn into a sale of some sort of services or something that you could probably do for them The other piece about it is, I mean, there's been so many stories of on the development programming side of someone holding down multiple jobs where the companies don't know that this person is actually holding down multiple jobs and they're either offshoring the work to some other country, some other individual who's actually doing the programming development work.

Or they're using AI or whatever other tools that they have at their disposal as heavily as possible to try to basically take a couple different paychecks, make the meetings work in between all the rest of them and just kind of make it work. I can also see some point to that too on AI's ability for scaling and efficiency.

If you really knew SEO well, how quickly could you turn around a project? What's the value there that you could still bring probably reduced, but maybe, I mean, that's what

SEO vs. Digital Marketing Consulting

Dave Dougherty: now are we talking, are we talking specifically about SEO or are we talking like digital marketing consulting kind of as a whole?

Cause that would change my answers.

Alex Pokorny: Sure. I was just thinking SEO, but yeah, let's change it up. Digital marketing overall. What's, what's your reply? So

Dave Dougherty: for me, I knew that as much as I loved SEO well, and still, I still really like it. It's a primary lens that I view the digital landscape with I knew that I would want to step away from it at some time either because the market was going to change or because my interests were going to change.

And I have, for me personally, I have a very hard time seeing myself doing anything for 10, 20, 30 years. Like I just can't imagine that far out. And I think the way that I'm hearing peop non SEOs and people who haven't had the training in SEO, the way that they talk about it, especially post ai I think they just assume that the AI is doing the SEO or like, yeah, the technical side of SEO can just be handled by it now because they do all the technical stuff anyway.

Or AI is doing all the technical stuff because I told it. You know, in my query, SEO optimize this thing. Well, what do you mean by that? Because even if you were talking to a freelancer, there's a lot of different ways that that could go, right? So the nature of the SEO projects have changed just because of that.

You know I know there are certain elements where, you know, if it doesn't work for ranking and it's, but it's something that you need to do in order to you know, have your, your checkbox completeness or whatever yeah, you might use AI for it just to have it done and, and be good meta descriptions come to mind or Like video tags, blog tags, you know, that kind of stuff.

Alex Pokorny: Yeah. And then digital marketing overall, you'd say go for it.

Dave Dougherty: I think you have a better chance of making enough income to support yourself. Right. If you did the digital strategy overall, if you were able to talk about how the company, the client wants to go to market, where the audience is, how the audience interacts, right?

Because those are, those are the things that are actually setting the communication strategy. Those are the things that are setting the channel strategy. More than just SEO, right? Cause SEO assumes that you have an owned media strategy. The website plays an important piece in, in what they're doing. And you want to optimize that, you know, and I think a lot of people.

In certain business models are actually stepping away from the websites as much, which I find fascinating. But yeah, I do think you'd have a much better chance to, to have a broader strategy view than

Alex Pokorny: just SEO. To pull on that thread for a moment. What are they looking toward?

Shifts in Digital Marketing Strategies

Alex Pokorny: They're pulling away from websites.

Dave Dougherty: This is what I've been noticing, and maybe you will disagree with me, which I would welcome the debate on. I think if you look at the way the tools have been going, like with with the AI tools, with Google, you know the other platforms, there, you have, you know, The walled garden thing that's going on with Google and Meta and, you know, Zuckerberg doesn't want anybody in charge of how Meta does anything, right?

Google wants to keep you on a Google platform, but then there's an increased focus on the verticalization of everything. So it's not just. Do some keywords. It's not just you know, I have high quality content for this thing is, are you showing expertise and authoritativeness across the entire vertical or is it a certain section of the vertical that ends up laddering up to the larger thing?

You know, the health and wealth was definitely one of those things, but I think the over the reliance now on the, the eat standards for SEO makes it. Harder for you to be in multiple things, you have to stay in your lane of, you know, the search engines expect this type of content from this type of business.

And if you're not producing that, then you have less of a chance to, to rank for things which makes it harder. But I also think, you know, What's old is new again, and I've been saying this for a little bit, but I think, you know, some of the older techniques of PR end up becoming more important where maybe you're not taking time to create content for your website as much because your audience doesn't necessarily go to the website unless it's looking for product specifications or whatever piece of research you might have done.

Maybe they're hanging out on Reddit or a trade organization website or magazine or, you know, something like that. Right? These places that specific audiences are aggregating towards are the things that are. Easier to target and you might get more, more targeted eyeballs than you would just that, that mass communication strategy that, you know, digital marketing has always been.

Alex Pokorny: Yeah, I could definitely see that. I'm just thinking of like tool and platform adoption and the content changes that would, that requires. So if you're a small restaurant, honestly, as long as your listings are pretty good online, your Uber Eats is filled out. I mean, your other kind of pieces, like you've got decent.

You know, shots of your food as well as the complete menu and a non uploaded PDF kind of wonky version, but actually like a working version. And if your Google Maps listing or Apple Maps listing is set up correctly with hours and address and takeout and delivery options, yeah, you don't really need a website like that's that one's kind of outside of it, depending on where your market is, right?

I can absolutely see that, especially, let me think about even down to the e commerce side. So many searches now are starting on Amazon for e commerce, at least in the U. S. But it's quite a few other countries as well, that still remains true. It's not a Google search, it's an Amazon search. And people have gone down pretty far down that path without always going through that top funnel, high volume, kind of generic query till they find something, they find something, they find something and now they're on Amazon.

A lot of times they have an idea of what they want and they go to Amazon to start and finish and purchase and that's it. Like, so then it's your Amazon listing that really needs to shine, not your website. Right. So. I see that I could definitely see that kind of distributed piece. The other piece I see from the digital strategy kind of overall offering versus an SEO offering.

There's a pro and con there. The pro side of it is you have an individual or company group of individuals who are very focused on the service that they're providing. They are the best at. Whatever. It doesn't necessarily mean they have any expertise at all in marketing. And if they were to need marketing help, they probably need a pretty broad swath of marketing help.

And also how often have you come in to see a company and they think they have some idea of doing marketing and they're asking you to do something that makes absolutely no sense because they don't. And they really need to kind of rebuild things from the ground up. Being there at the ground up would be nice.

The other side of it for with SEO specific skills or any kind of subject matter, expert specific offering, you can charge a lot more money for it might not be ongoing though. And that's always something that I've struggled with from SEO freelance work. You get a project, the project's done. You get a project, the project's done.

An ongoing retainer is like, the golden thing that you're always chasing, but honestly that's, that's a pretty hard, hard deal to strike. It's a lot easier to do package or project based deals. You're saying, you know, one time setup, you know, one time recommendations and, you know, implementation thing or something like that.

You don't have this ongoing fee that you have to pay for. A consultant or just a strategy consultant could have,

Dave Dougherty: right? Yeah, I do think with the nice thing about the tools that are out there now, whether it's AI or more of the traditional SAS tools that we're all familiar with the productivity of the individual freelancer can go through the roof.

Right. So you can offer more things and you can offer more things cheaply on the surfaces is a wonderful thing. Like I, the email specialist example that you bring up where it used to take seven people and now it might take maybe, you know, mostly one because of the drag and drop. Things now with, with templates.

So that's wonderful, but that's also true on the client side. They can now subscribe to the same tools and have their in house marketers do the exact same thing. Yeah. And I think the only thing that you're actually going to get a chance on is the one off projects or You're going to get the things that the marketer doesn't want to do themselves for whatever project it is.

So, you know, you can handle that one portion of it, but maybe not necessarily the full. You know, end to end aspect of the, of the project just because of the, the tool availability and, and how cheap they are now.

Alex Pokorny: Yeah, the other side is as ease of use increases, differentiation becomes key. Like if everybody, including competitors can all have a hot spot.

You know, set up or basics of maybe it's Facebook advertising, depending on your market, Google advertising, geo targeted, depending on your audience. I mean, all those different kinds of things. If it's that easy to set up, that means your competitors also are going to be doing something similar to that.

Some won't, some will. So then if you want to rise to the top of those who are, that's back to your differentiation. You're one to. And then you have to have somebody who understands the potential and that they're missing it and that they want an expert. And that's somebody who's been in the weeds or at least has attempted it for a while and gotten frustrated and said, no, I'm willing to pay somebody to help me.

That takes quite a bit to get to that point. Yeah, there's going to be a lot of HubSpot ads out there for those same businesses that might be your. You know, target customer, and they're probably going to have a HubSpot log in before they ever contact you. I mean, their advertising budget's insane, so they're going to be in front of those same people.

Dave Dougherty: Yeah, and I do think there's an opportunity now that everything has gone so digital, I think there's an opportunity to do more of the in person things. If you can put yourself out there and do that, or, you know, all of the tried and true methods, right? Like going and presenting at the chamber of commerce or putting on a free seminar at the library for whatever local businesses show up or, you know, whatever else.

All of those things still are, are necessary. If you're gonna, if you're gonna build things out and, and work that way because over the last 10 years. To circle back on our previous conversation, I, the one thing that I think has changed in a lot of conversations I'm having recently is that allure of the, the, the San Francisco dream, right, where you can be the one person in your bedroom or garage or whatever else, and you can instantly scale globally and that'll be wonderfully, globally.

And I'm hearing so many more people after trying that being completely burned out on that going, Hey, wait a minute, I actually don't need to scale beyond, you know, the five cities surrounding me to make a decent living. Like I could just do a local thing. How does that change where I prioritize my time and my energy?

Because I don't actually want the headaches of being, you know, the number one realtor across five states, because now you're talking interstate commerce and whatever else, right? Sure. Like, what do I actually need, you know?

Alex Pokorny: I definitely see that, like, and also, mostly there's competition there that is like, reasonable, and that you're able to win with, you know, I mean your human presence, your trust signals basically that you're giving off versus the random blog of whatever blog.

com that tells you the 10 ways that you should be doing digital marketing today. Like which one are you going to believe the person in front of you who talks for like five minutes or the random blog and I'd probably say the person because if they sound like they know what they're talking about, they probably have a whole lot more to tell me than a lot more to trust.

And you have that ability for communication as well. There's actually, there's a funny example. I've seen. Quite a few recently that were all the same, though. It was people who are doing handmade crafts of some sort and they were trying to sell it on Etsy and trying to sell it on Amazon and trying to scale it and trying to hire larger companies or CNC mills, basically to try to like.

Build as many as they possibly can. And they're struggling with shipping prices and seller prices and fees and all the rest of that stuff. And then I'm in thread between all of them was that the majority of their income comes from local businesses, local arts fairs, crafts, fairs, all the rest of that kind of stuff.

And actually the online sales while there's. Basically churn there, a lot of products being created and sold. The margin is so bad or an alternative competitor company quickly duplicates whatever unique feature they had, they lose it. They totally lose it. And then they have to go right back to traditional methods of trying to be in front of people's faces and, you know, try to get out to the local gift shops and whatever else and sell them 10 of them at a time.

Oh, that's funny. I mean, your, your phrase is absolutely true. It's old is new. Yeah.

Dave Dougherty: Because the other thing to think about too is, okay, if you have. Joined us and listened to us talk about AI and digital marketing, or you're listening to other podcasts like that, you're, you're on the tip of the spear because you're actually thinking about the new technologies, how they're impacting your strategies, all of that,

you know, traveling recently for a convention, I was sitting in the airport. Just listening to all these, you know, older business guys talk about the same convention I was at, right? And the way that they were talking was just a really great reminder of this huge population of people that just jump in and out of what's available to get their message out whenever they suddenly need to get something out.

You know, and if you think about that's probably the majority of the workforce, honestly, like, you know, I have this product, how do I get it out? I have X number of dollars for my marketing budget. Sure. I had success with paid ads before. Let's look at, you know, Google search. What happened in Google search recently?

Is it still the way I remember it? Okay. No, it's not, you know, like that's a, that's probably representative of a lot of, a lot of people rather than did you hear about the latest algorithm update? This tiny little minutia is changed. And, you know,

like, okay, I don't have time to think about that because I got, you know, two young kids at home and, and you know, Okay. Right. Mother in law is a pain in my butt. Like, I can't handle this right now.

Alex Pokorny: So yeah. Oh, yeah. It kind of gets back down. It's still about if you have a decent book of business, it's an ongoing. I mentioned retainers before, but even reups on annual contracts. I mean, standard shipments, loyal customers, call it what you like. You start to build that. It takes time. You build it over time.

You get that basically that cycle going and switching costs increases for your customers. They don't want to switch away from you. They got to find somebody else, whatever else. Maybe they had a poor experience last time, but not that bad of an experience. They're probably going to buy again. Like Again, you get back down to the same trust signals, the same sales piece, the same relationships from the 1920s, 30s, 40s, 18, whatever, 1700, whatever, same thing.

Loyal customers make the business work and that word of mouth helps. And those same, same tactics from before, too.

Dave Dougherty: Yeah.

The Role of AI in Marketing

Dave Dougherty: And I think the other thing too, because I listened to the AI podcasts and different things like that, right? Like the, the biggest thing recently was the focus on AI agents.

Alex Pokorny: Right.

Dave Dougherty: Right.

And HubSpot and Salesforce recently had, you know, big discussions on that with their latest expo convention, whatever you want to call it. And if you go, okay, this is going to impact. The knowledge work area that for anybody who's come up through the web 2. 0 or web one, sort of I'm the expert at, you know, email or SEO or whatever else.

Well, okay. So now I can find somebody who has that expertise, take a conversation with them and build a custom AI agent to handle all of that, or take all the research papers I can find online and upload it as training things. And then I just have an AI do the optimization stuff for me. And it's just done.

Is it perfect? Probably not. Is it good enough? Yeah, because then I get to focus on what I like doing, which is not looking at whether or not I have 20 keywords that are the right target of what, you know,

has anybody actually written image alt text in a long time? Not that I know of, you know, like, I mean, you have to now, but nobody likes it, you know, nobody really wants to

Alex Pokorny: That's where definitely AI picks up pretty quickly. I've been using ChatGBT a lot and Copilot a lot lately in the last couple of weeks.

A lot of daily usage basically with either of them. And no matter what, your questions and your requests are complex. The queries get complex. And the more that I play around with either one of those, the more that I understand how much innate knowledge I have to have Right. To really get to the thing that I actually want.

Right. And it tries to give me, you know, the base response, the basic, you know, answer to the question that I try to give out. And then I say, no, that's not quite it. I need this. And it keeps going back and forth and it just keeps hitting me over and over again. It is all based upon how good are you? At coming up with the right request, asking for the right thing.

And that's the thing that I think that's missed with a lot of these headlines. Is an AI agent will not take over marketing because you don't know what to ask for. You can't just tell this to say, Hey, let's build an email campaign around this specific offer. I want to call to action around this kind of stuff.

I want to have this kind of percentage off on my particular business and that will give me a healthy profit margin on that particular product line. No, you have to know first and then you can go to it and try to figure out, you know, each of those details, or maybe it can give you the call to action.

Great. But it can't say that 11 percent is going to kill you and 10 percent will be fine. All right. There's still so much innate knowledge that has to be present to utilize a tool and utilize it well,

Dave Dougherty: right? That's why I've been really fascinated by these people that have built sort of like strategy partners based on their knowledge just to bounce ideas off of.

Whereas, okay, you can be like my co strategist for whatever I'm doing. I all handle the actual numbers or the actual implementation of things, but help me think through this problem. That's, that's one of the things that I've found AI really useful for, right? Because you know, you wake up certain days, you just, you didn't sleep very well, so your brain's not capable of deep thought on the day you really need it.

So what do you do? You go to your friend typically and say, I need your help with this because I'm exhausted, you know, but now your friend's exhausted too because everything else they're doing. So you go to, you go to the AIs now to be like, just give me a first draft. Let me see if it's close to what I'm thinking.

Right. And then you can move on on from there. And, and make it your own and make it more representative of what you would actually want to promote. You know, it's not necessarily doing the work for you. That's definitely where I've found AI falling flat on its face. But it's getting better and better as it goes on.

Alex Pokorny: That was actually a funny conversation. I was thinking through when I was driving into work this morning was AI has created conversations and deleted conversations. So what I mean by that is at a project I mentioned on a prior episode of remodeling and redoing. renovating my basement and I didn't know much about, you know, proper design.

So I had a million questions and I found a GPT that was good at home decor and I asked it a million things and it was probably fantastic because my wife did not have to hear any of those. We probably made her very happy to be like, no, well, Amy means this. And I was like, what the heck is the difference between a curtain and a blind?

And I mean, I knew nothing, like nothing, nothing. So it was very good at that point to, you know, every once in a while, whenever I had a random thought to be able to just pull up my phone, send a query, learn a little bit, get that little answer or something else a little bit deeper and then keep on going.

The other side of it, and Will Reynolds had talked about this recently about his Excel expert at his agency. And he recently had a problem that he was able to figure out, I can't remember if it was ChatGPT or Copilot, which one he used. But he was able to figure it out with an AI, where he said, normally I would reach out to the person in my team who I know is the Excel expert.

So that person has kind of lost a connection point. I've lost a conversation. I've lost a little bit there too, but I've gained this efficiency, this nice copy and paste, this very quick response and answer that I got out of AI too. So it gives you, but it also kind of removes things, but I just, yeah, it was my drive to work.

I kept thinking about like. It's deleting conversations in a way because I don't reach out to friends to ask these kind of questions. I know I have a friend who's an expert in whatever, but I don't ask him. I don't ask her.

Dave Dougherty: Right.

Alex Pokorny: I try to figure it out myself and whatever I get is good enough.

Dave Dougherty: Yeah, it's, it's ever evolving. And I,

I think of what, February, an episode in February of this year, something like that. I had talked about how I was thinking more and more about like, personal connections and making sure that I set a priority to reach out to people I haven't spoken to in a while. And make that a solid part of my routine.

And as the years gone on and as I've learned more and experimented more with, you know, AI and different work scenarios, I am tripling down on that strategy,

you know, because there's something to be said. To being the person that people go to when they no longer have the connections to the experts to say, who would I go to for this? You seem to know everybody like that connecting

Alex Pokorny: person, the networking person, I

Dave Dougherty: got it right. I mean, there's some, there's some advantages of that, you know?

Yeah. So anyway, quick episode from us today. Thank you for checking it out, hanging out, listening to us. Tell us what you think. Are you thinking of going freelance now? Are you interested in that? Are you seeing the market environments as You know, scary, dark forest. You don't want to go into, tell us what tell us what you're thinking.

The emails in the episode description on the podcast or YouTube. Check us out, let us know, leave a review and we will see you in the next episode of Enterprising Minds.