The Corporate Escapee: On a Mission to Help 10,000 GenXers Escape the 9-5 Grind!

In this conversation, Jon Younger discusses the future of work and the rise of freelancing and gig work. He explains the difference between freelancers and gigsters, and the growth of the freelance economy. Jon also shares the four phases of early freelancing and the challenges individuals face when transitioning to freelancing. He discusses how enterprises are starting to think about freelancers and the importance of workforce architecture. Jon emphasizes the need for companies to adapt to the changing landscape of work and the opportunities that freelancers bring. He also provides insights on finding opportunities on freelance platforms. In this conversation, Brett Trainor and Jon Younger discuss various aspects of freelancing and entrepreneurship. They explore the importance of reframing sales as problem-solving and how to effectively ask for the business. They also emphasize the value of taking action and building a business, even without prior experience or talent. The conversation concludes with closing remarks and the possibility of future updates on the freelance world.

Jon’s Bio: As the “Godfather of the freelance economy”, Jon has been the leading voice for the freelance revolution through his Forbes column, advising, and research with the University of Toronto. A former Head of HR and Chief Talent, Jon is the go to for every marketplace executive. 

  • The freelance economy is growing rapidly, with millions of people working as freelancers or gigsters.
  • Transitioning to freelancing requires careful planning and consideration of income volatility, benefits, and the potential for loneliness.
  • Enterprises need to rethink how they resource their operations and build a flexible, impermanent workforce.
  • Freelancers should focus on their unique skills and problem-solving abilities to stand out in the market.
  • Freelancers can find opportunities on freelance platforms, but it's important to differentiate oneself and solve specific problems. Sales should be reframed as problem-solving, focusing on the importance of solving the client's problem rather than selling features and benefits.
  • To convert conversations into clients, it is crucial to learn how to ask for the business and confidently state the price.
  • Taking action is key to success in freelancing and entrepreneurship, as many people hesitate or do not take any action at all.
  • Building a successful business does not necessarily require talent or experience, but rather a willingness to try and learn from the process.
00:00 Introduction and Background
03:00 Defining Freelance and Gig Work
07:00 The Growth of Freelancing
10:00 The Shift from Employment to Freelancing
15:00 The Phases of Early Freelancing
18:00 The Future of Work for Enterprises
25:00 The Challenges for Enterprises in Working with Freelancers
32:00 The Rise of Fractional and Interim Work
40:00 The Changing Landscape of Work
45:00 Finding Opportunities on Freelance Platforms
46:01 Reframing Sales as Problem Solving
47:16 Asking for the Business
48:31 Taking Action and Building a Business
49:37 Closing Remarks and Future Updates

Jon Younger LinkedIn: 
The Human Cloud:

What is The Corporate Escapee: On a Mission to Help 10,000 GenXers Escape the 9-5 Grind!?

Welcome to The Corporate Escapee hosted by Brett Trainor,

We are on a mission to help 10,000 GenX professionals escape the corporate confines and find freedom and balance. We focus on helping you replace your corporate income by monetizing your experience and working fewer hours.

GenX was raised without many rules and a lot of independence. We want to show you how to reclaim that freedom

We blend stories from escapees, how to episodes, subject matter experts and authors.

Subscribe to Corporate Escapee Podcast define your legacy in the world of business today.

Join us and transform your expertise into a thriving, fulfilling business outside the traditional corporate confines.

Brett Trainor (00:01.511)
Hi, John, welcome to the podcast.

Jon (00:04.13)
Thank you, Brett. It's a pleasure to be here. Thank you for inviting me.

Brett Trainor (00:07.867)
Now the pleasure is all mine and super excited to talk to you because a lot of the time we talk from the individual side, the escapee side, right? The corporate and hey, how do I get into freelancing, fractional consulting, all this good stuff, but with a lot of the work you've done and a lot of the writing you've done comes from freelance at the enterprise. So I thought perfect time to help maybe educate people on what the future of work looks like, what enterprises are thinking, and you know, we'll see what are the rabbit holes that we can go down.

Jon (00:37.934)
I will do my best.

Brett Trainor (00:40.355)
Awesome. All right, well to get started, why don't you share just a little bit about the human cloud and what you're really focused on right now and then we'll jump into it.

Jon (00:50.702)
Sure, so the Human Cloud is a very small organization. We have a few people who are part of it. Matt Metolo is the CEO of the company, got it started, gave it a name, and has been around for a while. Matt had an early experience in Microsoft and in Gixter, and that led to a venture-backed startup that led eventually to the Human Cloud.

John Younger, that's me. I've got a little more history. I'm 72, he's 30. So together we're about 45 years old as an average. My background is that I'm an old professor. I've taught at places like the University of Michigan, at Wharton, I've taught at the Indian School of Business in Hyderabad, the Copenhagen School of Business in Denmark.

Brett Trainor (01:29.267)

Jon (01:49.054)
and the National University of Singapore. So a fair amount of teaching. I sit on a bunch of boards. Some of them are real boards, some of them are advisory boards. They tend to be primarily for startups or early stage companies. I coach a few CEOs and I've really had a lot of fun writing this Forbes column that I've been writing since 2018.

My deal is that I write five articles a month. I get paid $50 an article and I like that because it gives me a goal to shoot for. And I know kind of whether I'm doing okay or not. And it looks like it's had an impact. People seem to think my writing is helpful and people have started to call me the godfather of the freelance economy, which is a lovely thing to say. I don't know that it's particularly true, but it's a wonderful thing and it makes me feel warm.

The work with the human cloud that Matt and I do with our colleague Paul Polo, who runs our podcast activities, is really in three or four areas. We are educators, we're advisors, and we're people that help companies to figure out how they want to position themselves within the freelance economy or how they want to utilize the freelance economy to help them to...

have the resources that they need in order to be successful. So some of them are enterprise, some of them are relatively new and junior. And we hope for a nice mix because the combination is a powerful one. We're profitable, which is a lovely thing, and we have a little fun. So it's those kinds of things best describe us.

Brett Trainor (03:31.023)

Brett Trainor (03:38.003)
That's awesome.

That's perfect. And yeah, I love the mix, right? The, uh, the experience in the youth, right? It's kind of sad that I'm calling 30 something youth now, but it's the reality. And, uh, so when did you, uh, I know you've been writing about the freelance world forever, you know, and well ahead of its time, right? Cause I have had some folks on the podcast that left corporate and like 10 years ago before it was kind of a thing, or it was.

design, right? Design and copies and fiber and those types of things. But it's really kind of exploded. And like I said, one of the, the other, you mentioned the international experience, right? You talk about Latin America, how it's exploding. So maybe let's start with, what is your definition of freelance? Cause people hear freelance and they can go a thousand different directions. So why don't we get grounded with that?

Jon (04:28.418)
Sure. So let me do a little bit of geography and a little bit of categorization. So when you think about the terms freelance, they tend to be different than the term gigster or gig work or stuff like that. The best way to understand it is that a freelancer is an independent professional. Has the certifications, has the experience.

has the background, has the education, has the bona fides to represent himself, herself, or themselves as an expert in a particular area. And of course, the challenge then for the platform that they're working with or as they work alone is demonstrating those bona fides in the way that they're certified and the kinds of experiences they've had, et cetera. Second category, gigsters. And we define gigsters as

as people who are non-professionals trying to cobble together a reasonable living. And so they may have they may have degrees at Harvard or Yale or whatever, but what they're doing for a living, because this is not a statement of intelligence, it's just a statement of occupation, what they're doing is putting together work either driving as an Uber or a Lyft or a

Brett Trainor (05:45.704)

Jon (05:55.65)
maybe working for Amazon and delivering packages part-time, but the term cobbling together a living is probably a very good way to describe it. Clearly, there are more people in the Geekster category than the freelance independent professional categorization, but there are a lot in both. What we'd find right now, for example,

uh, MBO partners and Upwork and some other places estimate we're somewhere around 70 million people that are either working full-time or part-time as freelancers. Of those about 40% are full-time and about 60% are part-time. We kind of call them side giggers. We call them part-times. We call them moonlighters. These are people that have full-time jobs and are

Excuse me, seeking to either continue to learn, continue to make some additional funding, make some additional money, or just to have something else to do on a Saturday or a Sunday that causes them to have, in addition to their full-time job, some kind of freelance activity. So that's a, that's a sort of a general description. How many gigsters are in the world? Well,

Brett Trainor (07:13.777)

Jon (07:20.734)
I will tell you that there are quite a lot of them. And what we know is in Saudi Arabia, as one small example, there are about 1.8 million freelancers and gigsters, of which over a million are gigsters. So if you take that one country, I think there are a million there, now expand it to the 190 countries. And what you've got is a very interesting

Brett Trainor (07:37.679)

Jon (07:50.418)
opportunity for an awful lot of people, either professional or not, to earn a better living than they have been able to through the benefits of technology, either in scheduling or delivering the work that they do. Obviously, the work that they do is scheduled at Uber or Lyft by technology, not necessarily delivered by technology. But we now know that the combination of communication technologies

and the internet in general terms, is really creating massive economic opportunities for people whose only disadvantage was where they were born.

Brett Trainor (08:32.639)
That's a great point. Now it's so true. And yeah, pandemic probably helped accelerate a ton of this, right?

Jon (08:38.442)
Did in fact, what we saw that Brett between 2020 and 2023 is we saw a doubling of full time. From about 15 or 20 to. To to 40, probably 15 to 30Million, I would say. And we're seeing about in the US. These are the data. We're probably seeing. Another 50Million in sorry.

We're probably seeing 30 and then 40 in full time versus part time or moonlight. And those, those numbers are, are general. They're not as precise as I'd like them to be. But the message is that, uh, part timers have gone up by about 130% since 2020. And, and full timers have gone up by about 90% for different reasons. Clearly the reasons why you saw full timers move. Well,

Brett Trainor (09:20.744)

Jon (09:37.418)
Be kind of like guys like you and me that have said for different reasons we think we'll do as well or better and enjoy some greater flexibility. If we're independent professionals, as opposed to working full time for a particular organization and many of those guys are saying, why would we want to work for one company? When we could have the experience of working for three or four, we're mitigating risk. We're learning more. We're creating greater opportunity for ourselves.

Hell, what's wrong with that? And what we've seen is that part-timers are up about 130%. And why are they doing that? Well, it's good to have the extra money. It's good to have a vehicle to move from one job to another. It's good to see whether we can put something together as an entrepreneur and start to build our own business.

Brett Trainor (10:26.327)
Yeah, I think we're going to see a lot more of that. Again, just from the conversations I have with folks, they don't realize that the opportunity that's out there. And part of me, I go on rants because I spent 30 years in corporate. And if you look at your total contribution, right. And again, I learned a lot. There was a lot of value for me spending time in the corporate. And I got to a certain point and it just, it didn't make sense. And I just think it's become much more inefficient.

Jon (10:47.381)
Of course.

Brett Trainor (10:54.907)
Right. As, as time goes on unnecessary meetings, commute, just things that don't add up. And part of me starts to think, well, from a future of the enterprise, because that again, I've been more focused on small and medium sized enterprise because they haven't had access to resources or talent that they've had in the past. And, you know, one business owner told me I'd rather have, you know, 50% of an eight player than a hundred percent of a B player, but there was never any eight players around now there's more and more eight players starting to circulate.

But what's interesting is, and I'm curious to hear from your standpoint is how are enterprises starting to think about this? Cause they've had trouble just managing employees, let alone a, a network or an ecosystem of, of specialists. So where, where is that going and who's, you know, so I guess where I'm going to that is if somebody's in corporate now looking to go solo, but still likes that the corporate side of it, you know, what are some of the companies or areas that are starting to adopt the.

the more fractional or freelance approach.

Jon (11:55.63)
Good. And let me answer that in a couple three different steps. Step one is let's talk about the shift from employment to freelancing. And the message to an awful lot of folks that are thinking about it is it's harder than it looks. Be thoughtful and planful about it. One of the things that people tend to do is overestimate their contribution to what's happened.

Brett Trainor (12:01.329)

Jon (12:24.662)
corporately forgetting that there were an awful lot of people who are somewhat involved in the stuff that they're doing. It's a difference between having access to resources and being on my own, right? So that's the first thing. Second is it's really important, Brett, for people to figure out whether they've got the up-to-date knowledge to be a player now versus a player when they started 30 years ago or 20 years ago or...

Brett Trainor (12:36.698)

Jon (12:53.25)
15 years ago, an awful lot of people, for example, let's use the example of consulting where both you and I had an experience. I took two companies public or helped to take two companies public in the nineties and then the early two thousands. But the world has changed in the last 20 years. And so one of the things that I grew up being pretty good at was transformation.

I was pretty good at helping companies transform their operations, transform their marketing, transform their talent management, think go from A to B where B is really different. But asked me how much I know about the digital side of transformation and the answer is not much. If I were going to be a full-time person in consulting these days, I'd need to relearn a whole lot of stuff. So first it's...

Not the same. It's not just a move. Second is that there are three things that people thinking about moving to freelancing have a problem with. And I'll give this to your audience and I'm sure they'll relate to some of it. There are three things that caused me to pause about going into freelancing. The first is...

Brett Trainor (13:51.366)

Jon (14:16.642)
that I'm worried about income volatility. You know, when I work full-time, I get the same check every week. I may get a raise once a year, I may get a bonus, but man, at least I know what's coming in and going out. When I'm a freelancer, I don't. It's much more volatile. Second is, I liked getting two weeks off for vacation in four weeks when I was there for 20 years.

I don't get a vacation paid any longer as a freelancer. I don't get a 401 if I'm in the US when I'm a freelancer. And so there's lots of little benefits. Corporately, we counted them around 25% to 30% of a person's salary was on top as benefits. I don't get that anymore. And the third is it's lonely out there if I don't know how to do it right.

Brett Trainor (15:11.43)

Jon (15:16.662)
because I'm working from home and that even though I may choose to work remotely, if I'm in a big company, I've got a community. As an individual freelancer, I've got to create a community. I don't get one for joining. So that's very important. And then I'd add one other thing, Brett, and that is we did a bunch of research a couple of years ago and looked at the early days of freelancing.

Brett Trainor (15:34.904)

Brett Trainor (15:39.582)

Jon (15:45.546)
And here's the message to your listeners. There are four stages of early freelancing over the five to 10 years that you would start. Let me tell you what they are.

Stage one is, can I do it? And what we know about the first year freelancing is that it's frustrating, it's hard, people are not as successful as they thought they would be, et cetera. And it's because they're still learning the ropes. They're learning how to do this. And so when you ask them if this is a good choice, they vote pretty low. They're wondering whether or not it's gonna work out for them, especially if they're full-time. And at the end of the first year, people make a choice.

And that is, can I make it? Am I making it? Is this happening in a successful way? And what we know, Brett, is that a bunch of people, we don't know the exact number, but a bunch of people say this is not working for me. And they go and find a full-time job or something else. Of the people who have stayed a year, something interesting happens. By the end of the first year, if they've chosen to remain in freelancing, the chances are pretty good that they've figured out how to be successful.

And so their numbers go way up. They, they kind of 50% increase from 30% are happy to almost 50% are happy in that second year, which is now I know how to do it and I know, I know I can. And for the next couple of years, people tend to be pretty enthusiastic. And then they hit the three year point and Brett, here's the three year point. I know I can do it, but is this who I am? Is this what I want to be doing?

Brett Trainor (16:57.381)

Brett Trainor (17:22.875)

Jon (17:24.99)
And the third stage of an early freelancing career is making the decision, the affirmative decision to be in this or not. So again, at around three years, I make the decision that I'm either going to stay with it or I'm going to go back to something else and I hit another trough at that three year point because I got to figure this out and this is a hard thing to figure out. This is my life. This may be our family. This is all sorts of things.

And for those people that decide it's not working out, they're gone, et cetera. For those people that figure it out and decide to stay, they get enthusiastic again, and that enthusiasm continues. So four phases, phase one is can I do it? Phase two is I can do it. Phase three is, but do I wanna do it? And phase four is I wanna do it, and I can do it, and I'm doing great. And that seems to describe the four phases.

Brett, did you go through all four phases? All right.

Brett Trainor (18:28.819)
I did. And when you said that one year, Mark, it was spot on. That's when I finally hit the momentum and got the mojo and saying, yes, this is absolutely what I want to do. And then start to figure it out. But I think it's, it's such a good point. And, um, I had a guest on, um, Bruce Rolls. He's a COO, a fractional COO. And he is my compass that says, remember this isn't for everybody. Cause I'm like, everybody can do this, but is it for everybody? And he likes to remind me that.

Just like you said, here's the stages. Um, can everybody do it? That's got 30 years of experience. Yes. Is it for them? Maybe not. And, um, I think that's, that's absolutely right. When you say can write, I'm reminded of the, the can and will, right? There's a ton of people that says, yeah, I can, I can do it. Will you do it? And if not, and if you don't want to put the effort, if you put the effort in, you can be successful, but you've got to get up every morning like I do and say, this is awesome.

Jon (19:15.486)
That's exactly right. Right.

Brett Trainor (19:27.579)
Maybe not, I don't get up every morning and say, that's awesome, but it's working towards what I want. And this is, it's been, it's been great for me. Um, no, and I love these poor stages. And the, the one thing that I would, what I do tell people is they think that the risk is so high if they do this. I'm like, and they think, you know, that the tight rope between skyscrapers, if I fall off, you know, life ends, it's I'm like, no, you can go get another corporate job, but I say, if you're going to do it, you got to put the effort in.

Jon (19:34.262)
There you go. Now that.

Brett Trainor (19:54.291)
to see if it makes this work. And if you don't wanna put the effort in just to test, you probably aren't gonna put the effort in once you're doing it, go back and get your paycheck and do it, so.

Jon (20:05.65)
I think that's right. And I'll add to that that, you know, one of the things that's tough for people is figuring out is this a lifestyle that they like? Is this a lifestyle that they want to be part of? So let me turn for a second to what it is that they want to see from their clients, especially their enterprise clients, that sort of bulks up their confidence that this is real for them. And we...

We collected some really interesting data about both what people feel about their platform and what they get out of being part of their platform and also what they feel about their clients. And I want to explain a couple of things to your audience, and that is that it varies tremendously by your vertical. So there are four basic verticals in freelancing. One is tech.

And all of those variations of tech, it's everything from data science and AI to full stack software developers, et cetera. Second category is marketing services. Marketing services is bringing in a fractional CMO. It's working with a team of people that include a videographer, a photographer, SEO person, et cetera. And these are folks, there are many, many hundreds of platforms that have

brought that stuff together because they're really, it's a function of disassembling agencies, right? Well, agencies bring them together and now they're disassembling those agencies and creating freelance platforms based on it. Third category is independent management consulting, where you came from, right? So what we know for example is Catalan, the largest of the independent management consultants has over a hundred thousand participants members. I'm a part-time expert

Brett Trainor (21:38.075)
Right, yes.

Jon (22:01.81)
in residence there. And not only do they have 100,000 folks from all over the world, they're doing amazing things, but they have quite a large revenue base because an awful lot of folks have said, well, instead of working for McKinsey, I can work for these guys instead of hiring McKinsey or BCG or Bain, I can work for those guys instead of et cetera, et cetera. Here's what clients are saying. Here's what

Brett Trainor (22:24.359)

Jon (22:29.794)
freelancers are saying about their clients overall. And then we'll go into specifics. Less than 50% of freelancers say that the companies that they're working for as freelancers get it. That they don't know how to work with freelancers. They know how to work with employees. They know how to work with consultants who they treat as employees, but it's hard to know how to work with freelancers.

Brett Trainor (22:44.296)
Now, interesting.

Jon (22:58.486)
where the arrangement is not as much a subordinate as it is, I've made an affirmative decision to be part of your team. That doesn't mean I'm your guy. It's no different than me being part of a, me owning a bodego in Brooklyn and saying, just because you bought a banana from me doesn't, or a candy bar doesn't mean you own me. Doesn't mean I work for you.

We just had a transactional change. So part of it is an awful lot of companies don't understand that it's a different relationship and see the value in that relationship as opposed to the hassle in that relationship. Second, we see an awful lot of companies that say, my project manager doesn't get it. The company may or may not, but the guy or the gal or the person that I'm working for on this project, they want me to...

Brett Trainor (23:28.549)

Jon (23:57.378)
to act like I'm employed. They wanna call me at nine o'clock at night. They wanna ask me to come in Saturday. They're uncomfortable with me being remote, you know, all that crap. So we now have two factors that are areas where companies need to figure it out. Third is, am I working on interesting projects? And here what we see is, yeah, I like these projects.

Brett Trainor (23:59.827)

Brett Trainor (24:20.263)
Yeah, interesting.

Jon (24:23.882)
Am I working with interesting people for the most part? Yeah, I like the people. Or am I paid fairly? And the answer depends on what my category is. So if I used to be a consultant, well, Brett used to be a consultant, right? Used to make big money. Used to get in a, get in a black car and drive to the airport, get in business class, fly to your client. They were glad to see you. Not so much when you're a freelance management consultant.

And so part of the challenge for an awful lot of those guys and maybe for you part time, and maybe for me sometimes is I used to be a big shot. Now I'm just another guy. That's hard to let go of. In general, companies that hire technical people understand more are better partners with freelancers because there's greater history around tech being the freelance category.

Brett Trainor (24:52.567)

Brett Trainor (25:20.476)
Right, right, right.

Jon (25:21.206)
Marketing services, not as much. Independent management consulting, not as much again. So we're also seeing differences by vertical or category around whether clients, big companies, enterprises know how to work with freelancers. There is no question in my mind, to your point earlier, that we're gonna see more companies depending more on

freelancers, it just makes sense. And what I'd say to you is imagine a matrix. Just imagine a matrix. And you've got some skill sets that are really strategic. I mean, you need to know this stuff. And there are some skill sets that aren't really strategic. You may have to do it because the law requires it. But at the end of the day, in the first case where it's strategic,

Brett Trainor (25:54.62)
It does.

Brett Trainor (26:15.379)

Jon (26:20.866)
you're looking for super special people because it makes a difference. When you're looking for freelancers, are you really getting the best of the bunch in this area? In other areas, we don't need the best of the bunch. In other areas, we just need somebody that can get it done. And so what we're learning and what we're teaching our enterprise clients is that you need to build a skill.

that an HR has never really been built, Brett, and that is the skill of workforce architecture. Thinking ahead, thinking five years ahead to the skill sets that we're gonna need in our company, what is it that's crucial and strategic? What is it that's gonna become less and less important or more and more common over time? And how do we start to think about those roles where

Brett Trainor (26:55.707)

Jon (27:16.682)
We don't need a full-time person. We only need a person for these periods or these kinds of projects. When they come up, why not find the best in the world and bring them over to us for those moments, as opposed to having kind of an average person, a B player. If I may put it that way, who's full-time when in fact, we don't need them full-time.

Brett Trainor (27:31.023)

Brett Trainor (27:42.235)

Jon (27:42.614)
That's the big challenge facing an awful lot of companies. They're going to have to rethink how they resource their operations, given the opportunities they have to bring people in on a fractional basis, on an interim basis, or on a project basis.

Brett Trainor (28:02.295)
Yeah, I'm a hundred percent with you. And I do want to go down that path on my, I'll share my theory of the future of work. But you know, the one thing I'd go back, I think was, which is interesting because again, through my journey over the last, call it the last two years where I got deeper into the, the client side of this. It's, uh, if you slice it, right. So you've got the verticals, but if you slice it by company size, what I found is when I tried to bring my management consulting hat into small and mid sized companies.

Jon (28:07.438)

Brett Trainor (28:29.859)
It, they didn't, that's not where the value is. The value is in level one type self foundational stuff. How do I start to build these foundations where again, if you've got the 20 years of experience, you can come in and help them build foundations, a hundred percent agree with you on this specialty. And, you know, and again, there's folks that are AI where it's that going to go. Who would I hire right now? I don't even know just because it's emerging, but I think there's a time and place in levels that you can slice it vertical, you can slice it by size and figure out where your skill set.

fits best and where I think too, where I found at least moving from the consulting to the fractional, it moved to more of a partnership. So the way I, my super simplistic mind thinks about it is the employee employer relationship, it's, it's control. You mentioned it earlier. It said, Hey, you're an employee. Uh, when we moved to what I would call freelance or, um, more traditional, it's more transactional, right? Hey, I'm going to provide a service. You paid me for it.

we move on. And then when you get into the fractional or interim, I actually become a part of your team on a part-time basis or a full-time for a short amount of time. That's when you truly get that partnership and you got to be on the same side of the table because if you don't, it's not going to work. And the advantage, at least coming from this side, the individual side is you can leave, right? Unlike as an employee, it's much harder to change jobs and go find it. And so...

I think it's fascinating where the enterprise side of this is going in a hundred percent agree with it's a super specialized into those, those bigger companies, um, cause they've already got the foundation, maybe they have too much of a foundation in some of the areas. So.

Jon (30:07.822)
they have the foundation. And your point, which I like very much, is let me differentiate for a moment between interim and fractional, because they're really very different. So in any way, I mean, just definitionally, an interim job is a period of time. A fractional job is, I have an ongoing relationship, but I'm defined in terms of the stuff that I'm working on or the amount of time I'm providing. You know, what we've seen is that

Brett Trainor (30:18.707)

Jon (30:37.558)
The interim has become very popular in Europe. It's become popular in Europe for obvious reasons. And that is it's really hard to fire people in Europe. I mean, outside of the UK, if you're starting to think about the EU, I mean, we're talking about paying a guy or a gal or a person as much as two to three years of salary in order to buy their contract out. Well, that's just not that. That is.

Brett Trainor (30:46.907)
interesting. Yeah.

Jon (31:05.354)
in the U.S. so much of our work as it will, that what we find is that the interim, which is a holding pattern, if I may put it that way, just isn't as popular here in the States. What we are seeing is a lot of fractional stuff, particularly for early-stage, later-stage companies where they need a guy like you or a person like you

Brett Trainor (31:08.133)

Jon (31:33.858)
to just take them to the next level. And usually what we find is that interim assignments are far better scripted in terms of expectations, goals, et cetera, et cetera. One of the challenges for folks moving into fractional roles is you gotta show up and start delivering on day two. What's a hard thing for people that are used to taking the first three months to get a sense of the topography of the company?

Brett Trainor (31:36.083)

Brett Trainor (31:55.899)

Jon (32:03.742)
Right. And now the answer is you don't have time to do the map. You just got to get in and start helping and you better be helping from day two. So it's a different kind of each of these roles, whether it's fractional or interim or freelance, they all have their own hair. Right.

Brett Trainor (32:04.499)

Brett Trainor (32:15.132)

Brett Trainor (32:24.404)
Exactly. No, exactly right. And that's one of the things I tell people all the time. Really think about, I didn't do it when I left. I just kind of figured it out. What do you really want? Right? I mean, is it, hey, I want to just replace my income, but I only want to work two days a week, or I want to triple my income because then it can start to slide into what, and is this the type of work that I like to do? And does it make sense? And yeah. So I mean, the good thing is the options are growing and

You know, now, and since you brought it up, I want to go down the path with kind of the future of these organizations. And when I've been thinking about it, it started with the B2B digital transformation, you know, back before I was consulting, so this is seven years ago and just companies that were built before 2000 weren't built to serve as customers today, right? They just, they're thought silos are there. The operating budgets are all tied to handoffs versus the customer experience. And then the deeper I got into it, I'm like,

Why do we need employees at certain pieces? It's more of, you know, like today is hierarchy, but tomorrow, I think it's going to be more ecosystems. If I can plug in specialists in these different areas to help me. And the analogy that I use is, you know, hopefully it's a blockbuster movie, right? But Hollywood's coming in, Hey, we're, we're building star Wars. How many of those people are under the star Wars umbrella? Not many, right? You got hair, makeup, everybody, these small businesses all come together to

build this thing for 12 to 18 months, and then they go their own way and then maybe they come back. And the other analogy I'll use is Ocean's 11, right? When they're robbed the casino and Danny needs a safe cracker, he needs a disguise guy. Everybody has their specialty and I would argue that most of us in corporate for 20 years have some sort of specialty that we can apply. Now, how quickly is enterprise going to get there? I have no idea. But...

Jon (33:58.006)

Brett Trainor (34:11.683)
If these mid-sized companies that have proven, Hey, we've got a good product. We can sell. We just haven't really scaled can adopt some of this. It gives them a lot more flexibility. Right. I mean, it's a different model, but cause they still work with these small companies and they don't want to have, I got a higher salesperson or I got to do. Fit into the old model of doing things. So we're not there. I'm just kind of curious to get your take on this. Uh, where are we heading? Right. I mean, it's, um,

I don't think some of these bigger companies are going to be able to change. Maybe some will, some won't, but.

Jon (34:44.646)
I, you know, one version is who knows, right? Who knows? Second version, second version is we, we can see some of the paths emerging. So one path emerging is, we're going to see a tremendous, within the freelance world, and let me talk about both freelancing and enterprise. Within the freelance world.

We're going to see consolidation. I mean, this is kind of like the airline industry in the seventies, right? I mean, once it started dereg, we went from 90 or so airlines down to 20. And then we rebuilt, right? So there are 70 or 80 back now, but a different kind of airline. So I think we're going to experience consolidation. I think we're going to start to see less of a difference between traditional management consulting and freelance management consulting. I think we're going to see.

agencies and advertising firms merge with marketing services kinds of platform just makes sense. I mean at the end of the day what we know is that there's a tremendous opportunity to provide companies of whatever size through technology with the perfect skill set that they

had no idea existed because we have reach, Brett. We can find out who was that guy or that woman in Hong Kong that did that deal, who was that person in Kazakhstan that built that company, who's that individual in France that reinvented luxury. I mean, we can get to these people in a way that we never could before. One of the great challenges

and great advantages of freelancing is the opportunity to provide companies with the perfect skill set that they didn't know about. Hold on one second. Be right back.

Brett Trainor (36:48.187)
Yeah, yeah, yeah.

Jon (36:59.706)
That's one. Sorry for the intermissions. So that's one. Second is within the enterprises themselves, Brett, it just makes sense for them to combine a category of full-time people with a category of people who are part-time, could be part-time on a regular basis, could be, you know,

Brett Trainor (37:02.961)
No problem.

Jon (37:28.27)
project specific, we're going to see more and more employment arrangements being created. Now that we have the following tools. First tool is you don't have to be physically present. Second tool is we're able to communicate 24-7. Third tool is through AI we have increasing access

Brett Trainor (37:43.271)

Jon (37:56.834)
to best practice all over the place. And fourth, we've got a large population of excellent people that are interested in working part-time, interested in working fractionally, interested working on projects, et cetera. So the challenge for these organizations is a different kind of HR challenge. Historically, the HR challenge was, how do we keep the good people in?

And how do we move the not so good people out? That was it, right? Now HR's responsibility is gonna be to build me a flexible, impermanent workforce that's able to deliver what we need to deliver at an effective and efficient level, cost efficient and effective level, and sustainable over time.

Brett Trainor (38:27.056)

Brett Trainor (38:50.591)

Jon (38:51.934)
And you know what? We can do that. We can do that because the combination of tech and the facilities that we've now developed through freelancing, through interim, through the future of work kinds of organizations, I think we've got what we need. And so I am very excited about the future. I think it's going to be fantastic. Listen, we're going to have recessions here. And

great periods there and all sorts of things that the world continues to both appreciate and mourn. But one of the things that we do know is that the future of work has changed forever as a function of technology, as a function of disentangling opportunity from location, and as a

and as an opportunity exists for people to work in one part of the world and live in another part of the world. I mean that is, wow. I have great hopes for both that and for peace. And the reason I have great hopes for peace is that people don't declare war on people that they know well and enjoy being with and working with.

Brett Trainor (39:57.329)

Brett Trainor (40:18.undefined)
Relationships, yeah.

Jon (40:18.538)
And if we can create deeper, broader relationships, boy, that, that trumps greed every time, or at least most of the time.

Brett Trainor (40:29.223)
Yeah, no, I think 100% I've been on this soapbox to slightly you're a little more articulate with it than I am. But, but yeah, I mean, I think even to that the people are discovering. We talked about work life balance. I mean, it's just life and work is one piece of it. And the more we start to figure out what we want in life and how we get certain things, I don't think we're accepting just the commute into the job just

throw out, if people are going to keep arguing about return to office and those types of things, we're going to, if you're going to be successful, you got to move beyond that to the next level discussions here pretty damn quick. Um, interesting, but the one thing I know I've been holding, holding you for a while yet one more question, because a lot of the folks I work with and, you know, talk to is, Hey, finding those, those customers it's through your network, right? It's been changing the conversation. Say, Hey, when you're networking.

I'm also open to contract work or freelance or fractional if they understand that term. And they uncover a lot of different opportunities and a lot of the folks that are looking for fractional interim, we don't need a ton of clients, right? To hit where we want. But doing the research with you and talking to Matthew, you guys work a lot with platforms that are starting to emerge that, you know, like the fibers of the world, but for different specialties. Can you just give us a

Thumbnail that hey, if I'm thinking about, you know, platforms, are there some top or where can I find those resources to say, Hey, who are the, where are some of the areas that I should be looking if I don't want to just rely on networking, but potentially look at a marketplace or a platform to help me match my skills with somebody that's looking for it.

Jon (42:09.242)
You know, a couple of comments. Comment one is that most people are involved in a few platforms. And they're involved in a few platforms for a couple of reasons. One is because they're trying to distribute their risk. But the second thing is that if you think about the purpose of a platform, it's not to give you work. The purpose of a platform is to make

expertise available to clients. And if you're lucky enough to be curated in one of those areas, then you get the opportunity. So here's the implication of that. You got to decide whether you're special or just like everybody else. And if you're just like everybody else, you better hope for a good economic period. Because when business is good, when everybody is happy, when people are

Jon (43:07.542)
But that is not where we are in 2023 and it's not where we're going to be in 2024. And the only people that get a seat at a table are the people that have special seats that bring on demand skills that others don't have and need. So the message for, for folks out there is be honest with yourself. Are you special or just like everyone else? Are you offering unique skills or the same skills that everybody else has got?

Brett Trainor (43:12.442)

Jon (43:38.09)
And if you are, give a little thought to that. Give a little thought to how you can find in your experience the seeds of difference, the seeds of differentiation, the seeds of value, the seeds of special. And sell the heck out of those, man. Because at the end of the day, India has a million more software developers than it can use.

a million more than it can use. So the kids that were told in India a few years ago, learn coding and you're gonna do fine, not so much. But some coding is better than other coding. So what is it that you actually bring to your clients? And are you bringing something that they can't get as easily on other places? And if you are, you'll do well. But if it's just like everyone else,

Brett Trainor (44:20.207)

Jon (44:39.874)
That would be my feedback to them. Don't worry as much about the platform. Worry about what you bring to the market. Because if you bring something special, any platform will help. And if you don't, no platform can help.

Brett Trainor (44:40.177)

Brett Trainor (44:51.475)
It's getting out here. Yeah, it's such a good point. I always like to stress that. Why what's your different? Why are you different is always better than better. You're doing something different. And the other thing I encourage folks to really focus in on is, um, what's the problem that you solve now? Platform may have a little bit different when you're talking to a company. You can, you can, Hey, this is how I solve that problem. Um, but then when you get into a platform, it's more

Jon (45:01.77)

Brett Trainor (45:18.919)
boxed into these different things.

Jon (45:20.246)
Well, but you take that step, Britt, and you say, build yourself around the problem that you solve that you think will be important. So, you know, rather than saying I've had 20 years, blah, it's a whole lot better to say, I'm really good at these three things. And I've had 20 years of experience in these three things. And the other thing I'd say to you is, and one of the things I'd say to most of your folks is we asked.

Brett Trainor (45:28.065)

Brett Trainor (45:39.959)
Yeah, it's...

Jon (45:49.542)
in a recent bit of research, what are you good at and what are you not good at? Right? Guess what? People told us they weren't good at. They're not good at marketing. They're not good at networking. They're not good at asking for business. They're not good at, at those very things that they need to be good at in order to be successful as a, as a freelancer or as an interim or as a fractional.

Brett Trainor (45:54.046)

Brett Trainor (46:01.691)

Brett Trainor (46:16.195)
Yes. Yeah. That's what I, again, I try to get people to reframe that when they say, well, I can't sell them like, well, you don't have to sell again. You, you're a problem solver. You solve this problem and to solve this problem, it's going to cost you X, right? How important is this problem to you to get solved? And then when you start thinking that way, you don't have to sell features and benefits and as my followup and Nicole calling and all that, that.

Jon (46:36.97)
I liked what you just said and I put a little sharpener point on it, which is that.

Jon (46:49.186)
If I am nice to you and I give my stuff away and we have lots of conversations, we really enjoy those conversations, I may have made a friend. Don't kid yourself. You haven't made a client. Made a friend. Friends are nice. But if you want a client, you got to learn how to ask for the business. And we have, we actually, you know, I don't know how many people remember this stuff, but

Brett Trainor (47:07.943)

Jon (47:17.058)
Do you remember when Robert De Niro was young in the movie Taxi Driver, and he was practicing in the mirror, right? Remember that beautiful moment? I mean, what a fabulous actor. We all need to do that. We all need to practice saying, it's been really good talking with you. I think this is a good plan. I'm excited about it, and it'll cost you $40,000.

Brett Trainor (47:22.875)

Jon (47:44.994)
You gotta be able to say it. You gotta be able to name the number. You gotta be able to ask for the business. And if you're not sure you know how to do it, work with a mirror, work with a spouse, work with a friend, but figure out how to do it. Because if you don't know how to ask for the business, you won't get.

Brett Trainor (47:46.697)

Brett Trainor (48:02.547)
Yeah, no, it's true. I mean, it's, it's truly is a life skill. And again, the difference is if you're in corporate, you're not changing jobs that often, but you're doing the same damn, you got to ask for the job when you're interviewing. So it's, you know, I think it's right. I think there's a whole opportunity, which is two backs. There's some really talented people that won't get the chance because one, either they won't go over it. No, the other interesting, I keep taking us down another rabbit hole. Another interesting thing is, you know, the people that just won't do anything. Right. I mean, everybody like.

talks about you because you talked about the can, can I do this and will I do this? I looked on LinkedIn and the people that actually post stuff is, you know, like 3% or 5% and which again, I create it's, it's opportunity for people that actually will take action, right? If you're willing to take action, you have a good chance of success because there's a whole bunch of people that aren't going to do it. And so it puts you.

Jon (48:49.07)
Maybe you're right, you're absolutely right.

Brett Trainor (48:57.691)
You know, the other thing I share with folks is man, there's people building seven figure businesses that have like zero talent and zero experience, but they're out there doing it, whether it's valuable or not, there's the, so it's what I try to get people to just, just do it. If it doesn't work, you don't like it. Go back. But anyway, well, John, thank you. I know I've taken a lot of your time. I appreciate it. I'd love to have you come back maybe on a quarterly basis and update us of what's going on in the freelance world.

Jon (49:15.886)
There you go.

Jon (49:19.726)

Brett Trainor (49:27.091)
Like I said, I encourage folks to check. It's awesome. And so if people do want to find you other than in Forbes, you know, what's the best way for them to track you down and connect?

Jon (49:27.306)
invite me back and I'm glad to do it.

Jon (49:37.674)
I try to hide as much as possible. But I think, you know, if people are interested in the stuff we've talked about, tell them to check out The other thing, Brett, I'll tell you as we're leaving, one of the things that I'd be happy to share with you on a quarterly basis is we've started what we call the trend tracker, where we're asking a large panel of freelance leaders.

Brett Trainor (50:00.798)

Jon (50:04.718)
guys like you to tell us what's happening on a quarterly basis. What's your feeling about a bunch of things? Do you see the business opportunity improving? Are you looking for funding these days? Do you experience a recession on the horizon? Those basic questions. Glad to share the data with you on a quarterly basis. Maybe your folks will find it interesting.

Brett Trainor (50:29.051)
I think so. Yeah. Again, anybody that's listening to this podcast is either thinking about going freelance or already have and trying to figure out how to do it a little bit better. So I think, yeah, absolutely. Well, it's been a pleasure, John. Thank you very much. Uh, we'll look forward to having you back on. And like I said, it's going to take me a while to digest all my notes that I took from this today, but, uh, definitely appreciate it. All right.

Jon (50:36.234)
There you go.

Jon (50:48.818)
God bless. Thank you, sir.