At a certain point in your freelance career, the question stops being “How do I get more clients?” and starts being “How do I build a business I actually want to keep running?”

In this episode, Austin sits down with Matthew Fenton, a positioning and strategy consultant with nearly three decades of freelance experience. Matthew has worked with brands you’ve heard of, launched White Mystery Airheads, hired agencies and independents from both sides of the desk, and built a long freelance career around a simple but weighty principle:

Life plan first. Business plan second.

That idea shapes everything.

Austin and Matthew talk about what it means to design your freelance business around the life you want, not the other way around. They get into the challenges that don’t get enough airtime, like isolation, self-management, and the discipline required when nobody else is building structure for you.

Matthew also shares one of the most useful concepts in the episode: your gig floor. That’s the minimum threshold a project has to clear before it earns a yes. Right money. Right people. Right kind of work.

They also dig into what actually makes a freelancer rehirable. Spoiler: it’s not just talent. Matthew makes a strong case for reliability, sound judgment, clear communication, and the ability to be a real partner instead of a prima donna with a nice portfolio.

And yes, they also open a delightful can of worms on why freelancing is not for everybody and why Matthew opted out of the whole personal branding conversation years ago.

This is a grounded, honest conversation about sustainability, selectivity, and building a freelance business with enough structure and sanity to last.

Key Points

• A freelance career can be built for longevity. Matthew has been freelancing since 1997 and has sustained his business by staying focused on strategy, positioning, and meaningful client work.
• Life plan first, business plan second. The business should support your life, not consume it. That principle gets more important, not less, as your opportunities increase.
• Isolation is one of freelancing’s hidden costs. Leaving a full-time role means losing built-in social structure and accountability. You have to rebuild those on purpose.
• Warm reconnection beats cold networking. Matthew doesn’t think in terms of “keeping his network warm.” He reconnects with people he genuinely enjoys, and sometimes work falls out of that.
• Your gig floor matters. Experienced freelancers need a minimum threshold for what counts as a worthwhile opportunity, especially when demand is high.
• Reliability beats raw talent. The freelancers who get rehired are the ones who hit deadlines, communicate well, receive feedback, bring perspective, and don’t make the client regret saying yes.
• Freelancing isn’t for everyone. Some people are better off with a paycheck job, and there’s no shame in that.
• Personal branding is optional. Matthew argues that people are not brands and that many of the ideas lumped under personal branding are better explained elsewhere.

Notable Quotes

• “Life plan first, business plan second.”
• “The primary reason for your business to exist is to meet your needs.”
• “A deadline is a promise and failure to hit that deadline is a broken promise.”
• “Some people are truly better off with a paycheck job, and there’s absolutely no shame in that.”
• “I think pretty much the entire field of personal branding is nonsense.”

Resources Mentioned

• Follow Matthew on LinkedIn: https://www.linkedin.com/in/matthewfenton/ (Let him know you found him through this episode!)
• Check out his website: https://matthew-fenton.com/
• Check out Winning Solo: https://winningsolo.com/
• Join the Freelance Cake Community: https://www.freelancecake.com/community

Watch This Episode

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Transcript

00:00

You can only communicate so much and yes, you have examples that are different. Yes, you have Apple that people engage with daily on a very personal level, but that's not most brands.  That's a 1 % brand we're talking about Apple. uh But I can't say that when I've faced a difficult decision in my life, I've asked myself, what would Apple do?

00:29

Hey there! Welcome to the Freelance Cake Podcast. I'm your host, Austin L. Church, founder of the Freelance Cake Community. The goal of this show is to help full-time committed freelancers get better leverage. As the sworn enemy of busyness and burnout, I have no desire whatsoever to see you work harder. So I reveal the specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and satisfying. So chill out, listen in, because the best is yet to come.

01:07

At a certain point in your freelance career, the questions you ask yourself start to change. You start to think more about building a business and life you don't need a vacation from. My guest in today's episode, Matthew Fenton, has spent nearly three decades  navigating that very question. Matthew is a positioning and strategy consultant who focuses on the upstream decisions that determine whether a company wins or loses things like who to serve, what they stand for, how they are going to compete. Matthew has worked with really big brands you've heard of. He has also worked with smaller companies, and he now works  as the fractional head of strategy and marketing for one of those smaller companies.

02:03

In my conversation with Matthew, he and I talk about what it really looks like to build and sustain a freelance career over the long haul. One of the biggest themes is something that Matthew calls life plan first, business plan second. We dig into how that philosophy shapes everything from the clients he takes on to how he manages his time to when and why he says no,  and even which opportunities look bad or good on paper. We also explore the reality of freelancing beyond the highlight reel. We talked about isolation, loss of structure, the need to intentionally build connections with other people and the need for discipline in your work.

02:55

If you've ever struggled with too much demand, Matthew has some advice for you. He and I explore how he thinks about capacity, including a concept I really liked: "gig floor." Gig floor is how you determine what's worth saying yes to. Another major thread that I'll touch on before we get into the episode is what actually makes freelancers rehirable. From Matthew's perspective, after hiring dozens of agencies and independents over 30 years, what makes someone re-hireable is not just talent, it's also reliability, communication, and the capability of being a true partner who brings perspective, not just execution. The final thing I want to touch on is why freelancing isn't for everyone. Matthew and I discussed that. He also told me why he has opted out of the entire idea of personal branding. I really think you're going to like this episode, especially if you're an experienced freelancer thinking about sustainability, being more selective and designing a business that actually supports your life instead of consuming it. I hope you enjoy my conversation with Matthew Fenton.

04:20

Matthew, I am so glad that you agreed to join me and have this conversation. I have been looking forward to it. I want to talk about Airheads. But first, oh for folks who don't know you or any of your background, give us the synopsis of how you got into fun employment.

04:43

Sure! First, Austin it's great to be here too. I'm looking forward to a casual and wide ranging yet informative and dare I say, entertaining conversation with you today. I have been a freelancer for 29 years, since 1997. So I started my career in brand management. I am, in fact, the guy who launched White Mystery Airheads in 1993. Did not invent White Mystery Airheads, I have to be very clear. But I did develop and launch it. And then I left the candy company, started my own thing. I've been doing that ever since with the exception of one job stop, which I'll get into in a second. And all I do really, Austin, is I focus exclusively on the upstream questions of positioning, strategy, and messaging: What do we stand for? Who are we going to serve? How are we going to do that? How do we win? My default mode is fewer larger projects. So most years I have fewer than 10 clients, and really most years probably fewer than five.

05:43

The past three years, I've been in a fractional head of strategy and marketing role that's counted for most of my bandwidth with a long-term client. That's not the kind of thing I've ever done before. I was even actively seeking, but the conditions were perfect, and here we are. And then the only gap in my 29-year career was in 2010 and 2011 when a client hired me to be their VP of marketing. Another candy company, they no longer exist. They've been merged and subsumed into Ferrero. But at the time I had brands like Brock's, Trolley, Novonator's,  Jujyfruit's, Jujubees, Chuckle's, assembled by acquisition. So island of misfit toys. But that is my work history in a nutshell, the CV in 90 seconds or less.

06:30

That was incredible. And I think one reason I love spending time with you is just hearing some of the names of the candies takes me back to the little concession stand at the baseball field where I played Little League. And I'm like, you just walk up, you you get to request some candy. And I'm like, Matthew was behind the scenes, you know, watching some of these candies.

06:56

So  that's actually how your Airheads grew... was it was 10 or 15 cents. And before it was in  Target or Walmart, concession stands are literally what build that brand or we sell through Sam's club. So it ends up in your concession stand.  But if you're at a ball game with a little money in your pocket, you can get four or five Airheads in your day. It's pretty good.

07:19

I would always have more than four or five. If I could get away with it. Tell me about leaving the candy company and finding your footing as a soloist or consultant or whatever you called yourself at the time.

07:38

The very short answer in 1997 after I the candy company. I actually took a job that I hated. And this is not on the LinkedIn profile for reasons that are about to be abundantly clear. But it was a Fortune200 company. I was a group brand manager. I had just turned 27. I was a few steps down from VP. Life is good, right? And I got in there first day and I was like, wow, it's quiet. This is not the sound of laughter. It's not the sound of things being created, sound of things being analyzed. So already the first couple of hours, I'm like, all right, this is different from the candy company, which was great vibes all around. Really financially driven, I had come from a very consumer-driven company, so that was different. I was being asked at the new company to work on problems like how much quality can we cut from the product before the consumer notices? And that's not life's work kind of territory. That wasn't particularly interesting to me. And then kind of a pivotal moment, about eight weeks into that job, we had a marketing department retreat. Two consultants were brought in to make us smarter about marketing. And they said amazing things like a rational positioning is better than emotional positioning because a rational positioning can be proven. And our VP is like, write that insight down. And I just come from candy, right? So I can't sell you candy on a rational basis, you all crazy?

09:05

Are you all crazy? People don't buy candy because it's good for them.

09:19

Yeah. I was like, excuse me, have you not heard of Coca-Cola? Have you heard of the auto industry or the fashion industry? And I just kind of continued to disagree publicly and enthusiastically with these two consultants. And one of the breaks, the VP pulled me aside and asked me to stop doing that. So as I said at the top, I already knew I hated the job. And then I was confronted by two consultants who couldn't market their way out of a wet paper bag but had managed to be hired repeatedly by a Fortune200 company. So I thought to myself, If these two num nuts can get themselves hired, I can probably make something work. I gave you courage. That's the running from part of, there's a running two part that I was very lucky to have had strong training and brand positioning while working on Airheads Mentos was our other brand strongly positioned, growing like crazy at the time. And I knew I could help companies with that problem. And I just had to figure out how so I called the candy company back and said, I made a mistake. I'm not looking for my job back. But if you have worked for the summer, I'm available. And they said yes. And I had a client. Therefore, I was a consultant, freelancing is a breeze. And from that moment on, I have been a consultant, made the decision in literally 24 hours, turned in my two weeks notice during my ninth week on the job. They told me not to come back for the 10th week. But I was asked to stay on the rec league soccer team. So I had that going for me.

10:37

Listen, we want you for your legs, but we don't want you for your contrarian point of view. Exactly.

10:47

We need your defense, but not in the board room.

10:49

So two things I want to zoom in on. One, you called them and you said, I made a mistake. And do you remember enough about that to pass on like what that was like, because it seems like that requires some humility, but also I can't help but think that type of humility is very attractive.

11:16

Yeah, it's a great question, Austin. It was helped by the fact that I did not burn bridges on the way out when they had the little going away party at the first scanning company, I cried real tears. They were good people. And I had a really good relationship with my VP at that company. He's actually the guy who was my CEO at the second company and hired me to be that VP of marketing. So we always had good vibes. I knew I wouldn't have a problem saying I had made a mistake that they would be okay with that and they would understand that. And it wasn't, I don't recall it being a particularly difficult phone call to place. It might've been a 10-minute call.  

11:59

Yeah. What you said about not burning bridges really resonates with me. My first freelance client was my last full-time employer. I think there's something to be said for thinking about what story you want to be able to tell yourself afterward and trying to live out that story before it's happened and preserve relationships as much as you can. Second thing you said, yeah, I basically made that decision in 24 hours and then put in my notice. Are you a fast decision maker often? Are you very gut driven? Is that normal for you to make decisions that quickly?

12:47

This is a fun question. I am not purely gut driven. I did... I've always been, I guess what you'd call fiscally conservative. I had some money in the bank at the time and that helped. But I also like to ask the question, what's the worst that can happen? And in that specific case, literally the worst outcome I could possibly conceive of was I would be a total bust as a consultant. And if that happened, I would just go find a job. And I knew how to do that. It wasn't, it's not life ending. It's not career ending. It's that I tried something uh and it didn't work and we could have learned from that. And as it turned out, it did work and I learned from that too. What I do believe though, Austin, is life is short and don't stay in any condition where you don't see a better future, and that's frankly where I was with the in-between job, with the eight-week job.  There was no way I was going to change corporate culture. There was no way I was going to change the questions I was being asked to work on. And some people did advise me to stay the year just to have a year on the resume, but I wasn't about to sacrifice my 27th year of life. I physically could not get out of bed and go into that place by about the fifth week.

14:11

Something you said I think is so profound. I wasn't going to change the culture. And if that culture is causing you to not want to get out of bed, who cares about your resume, so to speak. So now you're consulting, you've got one client. Did you go straight into the things that you mentioned, positioning,  messaging? Have you played around with other focal points or types of work?

14:51

Another good question. Because when I started out in 1997, there were fewer people like me than there are now. There are fewer freelancers in general by a  wide, wide margin. It took me while to find my footing in terms of what do I believe the client needs and what are they actually going to buy and what do I do when those two things are not perfectly aligned. So I was, I started the business as a firm believer that everybody needs better positioning. I still believe that sitting here today. I didn't know that would be so hard to sell. I didn't know that a client who knows less about positioning, which is exactly the kind of client I can help. I didn't know that person doesn't know that they need positioning. They barely know it exists in 1997. So it took me a while to find my feet that way. And I'd also say I grew into the strategic end of things. So if I look at the work I did at the start of my career, more of your pure marketing silo type of stuff, more vertical, if you will. And the stuff that I'm doing lately is still some of that, but also as a healthy, top level strategic, horizontal type of element to it.

16:14

Did you always have a taste for strategy or is that something that you discovered later?

16:22

No, I always loved it. I am a secret nerd, I think like a lot of good strategists grew up playing chess, played a lot of poker about 20 years ago. A lot of strategists do the, you know, the magic, the gathering thing, role playing games, all the rest. I've always been really fascinated by the question of How do we win? And I didn't have words for that until I bumped into the writings of Roger Martin. But that is really what it's all about. And again, the first candy company where it's just our two brands, Mentos and Airheads, we're going up against Skittles and Starburst and then Twizzlers and brands that are literally outspending us 20 to one. They'd spent as much every two weeks as I spent all year. How do we win? How do we crack that nut? How do we get to where we want to be against that kind of opposition? So I was really, really lucky actually to start with a small and growing company, a company with a lot of upside. And it's just a lesson that's served me well for my entire career is doing more with limited resources. And part of that is just defining what does winning look like to me? Winning for Airheads is not the same as winning for Skittles. We have two different finish lines. We have two different starting points, two different sets of strengths. So what do I do that gets me to where I want to go respecting that I have to work within this environment that they've kind of created? So it was a great first experience and I've been doing some version that ever since.

18:05

So is that still the focus of your business? Messaging, positioning strategy.

18:11

Yeah. Positioning for me is a, how do we win question through the marketing silo. Messaging... I do not, I'm not a copywriter to be very clear on that. I do messaging frameworks, but I don't write the actual copy. So that's a question of how do we win through our communications? But that question just kind of permeates literally everything I've ever done.

18:32

I like that as  the lens through which you see everything else. I think because it can be simplifying. I love those questions  that when you put them in front of a client, the client has an immediate answer. And those are often the deepest questions too. But before I go down that rabbit trail, let's talk about your perspective over the last 30 plus years. What has been most challenging and what has been most fulfilling? And if you want to talk about that through the lens of what you think has changed and is like most relevant right now, even better.

19:19

Yeah. All right. I'll take those in that order. So most challenging over the years and especially early on, I think I struggled most with the isolation. I just, I really like people. I especially like people who will battle ideas around with me and challenge me and make me laugh. And there's like undeniably a social aspect to an office environment that's really difficult to replicate on your own. The solution to some of that is a social answer, making sure that my non-working hours help me to recharge that battery and get that need for connection. The other part of my solution has been to more deliberately reconnect with others that have crossed paths with us. So it's not a, it's not cold networking, it is warm networking. And I'm not a natural networker. I'd give myself like a B plus in my best years and probably a C minus in my worst. But I found it helps to not think of it as networking. Like keeping my network warm feels kind of icky. Reconnecting with humans I enjoy feels great. So I try to be the person who just reaches out to say hello, just to connect, just to see how things are going. If a gig falls out of that, and sometimes it does, then I'm very much in the bonus round. Otherwise, in and of itself, that half hour Zoom is going to be good for my soul. So that was my toughest thing, and I completely underestimated that, and I think a lot of new freelancers do, especially if they leave an office environment and go solo. They kind of don't realize they have to create that for themselves. They have to, they have to make those connections because they're not just happening every day.

21:08

So true. And same goes for time management as well. You have all this social and structural scaffolding around you in a full-time role. As soon as you leave that full-time role. Yeah, it's  hard to  find connection with people and self-manage, but you were about to answer the next question, fulfilling.

21:33

Yeah, the following question. Really it's that I get to execute a dive, my own selection. I can retain a certain amount of freedom, not complete freedom and don't let anybody sell you that gallon of Kool-Aid. But I do have significant freedom in terms of how I design my business all the way down to how I design my days. So I can and do take a break every day to take a walk or hop on the bell time. Very importantly, when my mother was dying in 2015, I could immediately ratchet the business down and go spend more time with her in Ohio. Those few moments in life where you're like, I have just one top priority right now, this mom and the business is a different, you know, kind of just a distant number two. So let's go do that. When my wife and I decided in 2022 that we wanted to leave Chicago for the generally rolling hills of Oregon wine country, we could just make that happen too. So it's really not an exaggeration to say freelancing is responsible for all the good things in my life. There's also a feedback loop to it that I find fulfilling. The market will let you know if you're hitting the mark or not. Freelancing will show you exactly who you are. It'll reveal your discipline and your skill set and your character and your attention to detail and your ability to learn and so many other things. So I'm approaching the three decade mark now. I've never stopped growing. I've never been remotely bored. So that is wildly fulfilling.

22:59

Amen to that. It's a rather unforgiving mirror. Freelancing is.

23:08

That is a great term.

23:09

So you mentioned earlier that you have, I'll call them an "anchor client" now. And you use the word fractional. At which point did you graduate from being a consultant to a fractional leader? And was that even a meaningful distinction for you or was it just sort of putting a label on something that had always been true?

23:39

Good question. It was a, I don't think it in terms of graduation because I don't think it's a step-wise type of thing. I think of it in terms of the conditions presented themselves and they were right. So I was never looking for fractional roles. I didn't have that as one of my offerings. It wasn't on my LinkedIn. It is now, but it wasn't then. The reason this worked was it was a client I've been working with since 2012. They're called Bob Rogers Travel. They are in the business of student performance travel, which is taking the high school band to Disney World, for instance, or to New York City to perform in the Macy's Parade or to Paris. So that's what they do. I've been working with them as a strategic marketing advisor from 2012 to 2023, January of, at which point their head of marketing resigned. And they called me in a bit of a panic. They actually called me on vacation, which is how I knew something was up because they were very much the kind of people who would not bother you on vacation. And they called and  said, hey, we just lost our guy. We need some of your bandwidth. We need it immediately. We need it indefinitely. And for most businesses, 99% of businesses that would have called me with that pitch, fast no. I don't know you. I don't know what I'm stepping into. I don't care what the money is. I need to know more before I can decide that we're going to hook up on that kind of level. With BRT, because they had been such a fantastic client over the years, it was really a snap yes. It was, hey, I'll be back in Chicago on Monday. We'll get this worked out. Don't worry about it over the weekend. We'll get this solved. And we did. And the form it's taken is now 25 to 30 hours in my week as their head of strategy and marketing. It's a company I believe in. They're fantastic executors. They really make me look good as a strategist kind of thing. I can put any words on paper. They're really, really good at getting things done. Their clients love them. High rate of repeat business. I've got a direct report and she's terrific and I'm really enjoying that. So it's really grown me in ways I wasn't expecting when I stepped into the role and it's been  entirely rewarding on its own. But it was, I will say, nothing that I set in motion and something that came to me. But it was also earned over a decade plus of trust with this client that cannot be understated.

26:21

I want to keep going down that track, but I want to make an observation first, which is you had the job, didn't want to get out of bed. Your point of view wasn't valued. And you put in your notice ultimately. Contrast that with the client who makes you look good because they sound like do value your point of view, will execute on the strategy, therefore we'll get results. All I want to say is I think that's one reason we freelance is because those of us who care about results, who actually care about making a positive dent, we want to see that our work matters.  And it doesn't sound like you had to take a pay cut, but sometimes we'll even work for less money if we can see that the work we're doing truly matters, like it's making the world a better place. And so just wanted to set up that contrast because it is a pretty vivid one sounds like.

27:34

Yeah, I love that you called that out. It is, and some of it's about some people being system quarterbacks, and I'm probably one of those. I wasn't in the right system at the Fortune200, and I am in the right system at Bob Rogers Travel. And some of it is exactly what you said, Austin, that if we're working with good people who are doing good things and are making you feel rewarded and valued, yeah, that's no longer a money conversation. That is a How do we do more of this conversation? And I'd much rather have that conversation.

28:09

Yes. Okay. So  I want to do down that track still, but a slight turn. And the turn is this. You're now, it sounds like the one doing some of the hiring. So what do you look for in  freelancers or fractionals or agencies? What has that experience been like for you to be on the other side? And I just tell me everything.

28:40

Yeah. How much time do you have? Cause this was all the way back. Even on Airheads, hired great big agencies, like GSDNM. That was the first agency of record for Airheads. They're based in Austin, Texas. Had just a fantastic team and learned so much about what a good agency relationship is and can be. But we also worked with a one-person design shop that did a lot of the, you know, your basic design, your sell sheets, your company meeting type of design. So I had kind of that whole range of experience. And that was also the case at the second candy company  where we hired a big firm, LPK, to do the Brocks redesign, but then we also had smaller shops on some of the other brands and we brought in a young woman of, I want to say, 24 years old to help us with, again, some of the lighter lift kind of graphic and design. Across the board, it made me a better freelancer because I do have that experience. And I think the one primary thing I'm looking for is reliability. Can I trust  this person's work product? Can I trust that they're going to hit deadlines? Can I trust their mood? Can I trust their ability to show up with the right tone in emails? And all those other things, it's not just about the work. And a lot of beginning freelancers really want to think it is. They think it's, you know, that I'm an objectively outstanding designer, and therefore I will get a ton of work. And there's so much involved in the client relationship that is not that... I want a partner who's going to  challenge my thinking. I want a partner who's going to speak truth to power, if you will. I want them to tell me if I'm on the wrong track. I want them to tell me if I'm asking for something and they think there's a better way to do that. I want them to manage their work proactively to keep me on track, to let me know if something's going off track. All those different things, that client service aspect is massive because I simply can't rehire or refer somebody who is unreliable. Can't do it. And that, if I had to boil it down to just one word, Austin, I guess it would be "reliability" that I'm looking for people I can trust to not just do the work, but to do the things that surround the work. And the bar is not that high. And sometimes it is missed by miles. So if you're thinking, you know, that's not something I can do, that's you know, I just, do design or I do copywriting or I do strategy and this other stuff is not something I can learn. You can learn it. And you've probably seen examples of it. Don't do the terrible examples  and try to emulate the good examples. And generally it'd be just fine. But again, you know what that's like when you're looking for a contractor. And you call three places and one of them gets back to you in 20 minutes. And one of them gets back to you in 48 hours. And one of them doesn't get back to you at all. It becomes a no bid closing. You're going with number one because they act like they want your business. And that tends to set the tone for the rest of the relationship. All those kinds of things are not that difficult to do. And the freelancers who do them, I have found ways to work with throughout my career. It's like when there's an opportunity for just about everything. Now I have one, maybe two names I'm going to call based on past experience cause I know these people are going to get the job done and they're not going to make me look bad in the process.

32:36

There's so much I want to say to relate to what you just said because it resonates. I think me relating hard would be less interesting to people than maybe just stating the opposite. You're saying that you will not rehire talented people if they're difficult to work with. And I know that we kind of, that seems obvious as soon as I say it out loud, but can you, before we move on, maybe just from different angles, explain based on your experience, what being difficult to work with looks like so that maybe some of the folks listening to our conversation can self-diagnose perhaps.

33:30

You You bet. Would love to. Some of it is, let's go with like the classic creative prima donna archetype. You know what mean? There are some people who are undeniably talented, but they can't receive feedback. They can't imagine that you, the client, are stupid enough to not see their self-evident geniuses as as presented to you. Those kind of things, you know, looks great on TV, kind of works in Mad Men, but it doesn't really work in the real world. And especially when you've got now literally thousands of other people who do some version of what you do. That's what the market is nowadays. And the prima donnas don't get invited back twice. So some of it is that receiving feedback and again, I want to be told if you think my feedback is off base, but I also want to feel like you're hearing my feedback and I'm to do my best to say, is where this is coming from. This is the principle that this sits on or the business issue that this points to or that maybe... Just simply hitting deadlines is massive with me. A deadline is a promise and get a failure to hit that deadline is a broken promise. Quality control. Just minding the details of one's work, cross-checking that people's names are spelled correctly before that document crosses my desk. That's a massive one. I want people who are going to bring me ideas. So there's kind of that perfect middle. I'm not looking for a bag carrier. I'm not looking for somebody who just does what I tell them to do because that doesn't have a ton of value. Nor am I looking for somebody who's going to argue with everything I tell them to do.

35:22

There's kind of a broad middle there for somebody who says, I hear what you're asking for. And also, let me add a layer to that based on my experience. Let me turn you 35 degrees on this, and maybe there's a different way to go. Or let me suggest, Matthew, that you're entirely off base.  And  I think there's a better way to make you happier to get done what needs doing. So it really is a combination of basic  lessons from mom when you're six years old, keep your promises type of stuff. And also show me the best of you. That's what I'm paying for. And that's what makes you rehirable and referable. That's what will make me tell my friends to hire you. You're not just going to get solid design, solid copywriting. You're going to get a point of view. You're going to get somebody who challenges you respectfully, but with the objective in mind. And of course, you're to get somebody who gets the job done on time and on budget. So I don't look bad to whoever I'm accountable to on my side of the desk. So it's a combination of a lot of things, big and little. But again, I'd underscore that we all have examples of those roles being violated in our own lives. We've all tried to find a good landscaper, tried to find a good financial advisor or accountant. And when those things go badly, do your damnedest to do the opposite of what you just had to endure. And when you start the relationship, you know, a quick callback, some enthusiasm for the business, some good questions, that sets a tone. And if you show up every time with the best of yourself, repeat business is going to take care of itself.

37:18

That has been my experience and everything you just said is a perfect segue to another question I wanted to ask you, which is looking back on nearly three decades worth of experience. What do you wish everyone, especially more advanced established freelancers knew about freelancing, about this path that they've chosen?

37:47

That is a really good question. If we want to isolate on advanced freelancers, and I think that we do, because so much of the literature is designed for just those that are starting out, and that's one thing I appreciate about what you're doing, Austin, with Freelance Cake. It's for the people who have been at it for a while, which is an ever-increasing number. I think my big number one would be six words: life plan first, business plan second. I'm assuming an advanced freelancer has largely solved the problem of hard seen demand. They might have a new and unexpected problem, which is like the phone is ringing too much. That's a luxury problem, but it's still a problem. And no matter how much business I have, no matter what kind of year I'm projecting, there's always that weird feeling when you refuse business where you're like, what are the long-term consequences of this? What if my phone, which has been ringing reliable, just never stops ringing again? So I found that it helps to revisit what I'll call my gig floor regularly and my gig floor is the absolute minimum parameters for a new gig to make its way into my bandwidth. That definition for me and for you may be very different three months or a month or a week from now than it is today, which is why we want to keep revisiting that. So a gig floor says this is my absolute minimum. I can say no for other reasons, but this is where it starts. And then once you tug on that string, you're kind of tugging on the larger question of What do I want my work to be? What role do I want to play in the overall fabric of my life? What boundaries am I placing on my work so that I can live a better life, a richer life? And I'll forget where I picked up this next little nugget, but it's come in extraordinarily handy over the years. Somebody said to me very early on, the primary reason for your business to exist is to meet your needs. The primary reason for your business to exist is to meet your needs.

39:45

And if you have middle child tendencies or you just believe in improving the client's condition, like obviously that's high on the list. You want to make things better for the people who have paid you to do that. But if you're making the client happy while you're miserable, kind of like, what's the point? And I know Austin, you're a fan of dedicated planning days where you kind of treat yourself like your most important client. You set aside time to work on what you want your business to be. I'm a fan too, I call those strategic retreats, you even if I'm just shutting out all my distractions for an afternoon in my own living room, I do that once a quarter just to make sure that the business I've designed is still serving me. And then when I do that, I like to start with the question of what do I want my life to be like, then how can I design my business to fit within that? And I found that approach to be more successful than treating my business like it's an isolated thing over here and life is over here. I think the proper hierarchy is that life is up here and business is down here. Business is a subset of life. Why I think work-life balance is a false proposition. There is no work-life balance. There's a life balance and work is one aspect of life. So that would be my biggie. And it becomes more important I find that the more successful, the more advanced you become as a freelancer, just because you have that constant crush of people who want to work with you and you've got to keep front and center: Is this what I signed up for? Is this what I want to design for myself? I did what I wanted to do on the business front. Am I doing what I want to do on the life front? And how does that fit for the season of life that I'm in right now? So again, in six short words: life plan first, business plan second.

41:37

Those  strategic reset or planning days... about how often do you put those in your calendar?  

41:48

They're on my calendar right now for the last full week of every quarter. So end of March, end of June, end of September, end of December.

42:00

I think what you said is so true. It's certainly been true for me. The more opportunities you have, the more important it is to reconnect or like reorient yourself toward the picture of the life you want. I think in part because it's just so easy to go after an opportunity that takes you away from that. But  another follow up question, gig floor, love that phrase. Would you mind sharing some of the criteria that help you give an enthusiastic yes versus hard no, hard pass?

42:43

Sure, because it just happened to me. I'm at pretty close to full bandwidth with BRT, as I said. That's 25 to 30 hours a week. I've come to learn over years that give or take 32 hours a week is where I want to be in terms of working hours. And of course, you have peaks and valleys. As the year goes on, you have periods of high intensity and lower. But that's been about my average is 32. So to  be the next layer on the cake that already includes BRT, there's a certain financial number we have to hit. There's a certain dollars per hour, we'll call it. I have to believe in the work. So I have to believe I'm doing something meaningful. And I have to, at this point, I know you or know something very positive about you. It's really tough to get on my calendar right now if you're a complete stranger with nobody in between. If you Austin came to me and said, I have this opportunity, I would take that phone call because I know and trust you. And of course there are now people I've worked with in the past who have gone on to different kinds of career opportunities themselves and might have a need for my services. So those are easy calls to take. But those are really the big three for me. Right money, right people, and right environment, I guess, right value that we're creating. Some meaning behind what we're doing.

44:27

I think we have time for one more question before I ask where people can learn more about you. Again, drawing from nearly three decades of freelancing and consulting... Talk to me about unpopular opinion you have, you mentioned earlier that a lot of the literature, to speak is for like, like new or early freelancers. Give me the 30-year perspective that might be unpopular.

45:09

So you really want to open a can of worms here? I'll give you two. The first would be that some people are truly better off with a paycheck job, and there's absolutely no shame in that. I love freelancing. It's been great to me. It's made my entire life possible. It's not for everybody,  so I kind of push against those people who, you know, like freelancing is the only way to go. If you don't freelance, there's something wrong with you. Not at all. And sometimes it's right for you again in different seasons and not in others. And I've seen people... go back and forth between both sides of the desk, that's fine. It's not for everybody. And it's important to remember that it's a crowded market. It's more difficult to do this now than when I started out. This I know. More difficult to get started now than when I started out. And there's kind of that, are you familiar with the Charlie Munger quote? The idea rule of life is that only 20% of the people can be in the top fifth. That definitely applies here in the sense that when you have more competition, you need to do more to make yourself stand out. You need to do more to be in that top 20%. So freelancing is hard, and as much as I believe in it, I've probably dissuaded more people from entering freelancing than I've encouraged them. I've met some talented designers, really talented designers. I lived in Cincinnati for a long time, and there's a whole design community that pops up around Procter & Gamble, just insanely talented people. But in a few cases, like, I'm not sure you have the appetite for the sales and marketing. I'm not, I think you want to be a designer. I don't think you want to be a salesperson. So those kinds of things. So that'd be the first one. Some people are better off with the paycheck job and that's fine. The second one, the one that's really going to make me some enemies is that I think pretty much the entire field of personal branding is nonsense.

47:15

Oh, yeah. Now we're getting somewhere.

47:16

Now we're getting to the meat of the matter. This is what I really hear. It's people like us that it's supposed to apply to, you, me, the people listening to this podcast. I have yet to find anything in the field of personal branding that wasn't previously covered and better covered in the field of professional service and marketing or psychology or philosophy. And I don't think people are brands. I think that's easy enough to prove because people invented brands, people manage brands. In some cases, people manipulate brands. But people and brands are not one and the same. If we think that we are, we're into some really fascinating questions like, Austin, are your children brands? Are babies brands? If your children are brands, should you not be raising them to focus on their brand instead of, for instance, their character? Is it a better world if everyone thinks of themselves as a brand, and acts accordingly? Is that a word you want to live in? So personally, and again, your mileage and the mileage of anyone listening may vary. I don't see how the concept of personal branding either improves my life or makes the world a better place. So  15 years ago, I just opted out.

48:25

You mentioned Roger Martin earlier. And I really like his work. I haven't gotten deep into it,  but the little I've stumbled across, I've really liked, especially this one idea I'm about to share with you, which is if the opposite of your strategy is not also a strategy, then you don't have a strategy. And I really liked how you broke down the idea of would you want to put a personal brand on your child? And you're like, well, probably not. That almost sounds like exploitative,  right?

49:08

Hmmm. Iicky.

49:09

Icky. Then when you also take that to an extreme, you're like, well, if you look at certain kids, like in the Disney universe, who talked about being forced to like professionalize too early and how damaging that was, you're like, Oh, that's interesting. You talk like you hear some kid YouTubers who became a brand and then later on sort of hated all of the notoriety that came with that. It really should make us slow down and be like, okay, maybe there are good business building principles up for discussion here. Maybe there's even some first principles thinking like, Hey, if you are not standing out, you may be hard to see, right?

50:06

But I love what you said. I think it's an important point of view precisely because people who haven't thought about it as much as you have may convince themselves, I really need a personal brand and not realize they have other options. Meaning not having a personal brand and not trying to fit a whole person inside of I don't know, a shoe box.

50:34

Yeah. And that's one thing I know from managing brands is they are by definition pretty narrow and pretty flat. You can only communicate so much. And yes, you have examples that are different. Yes, you have Apple, the people engage with daily on a very personal level. But that's not most brands. That's a 1% brand if we're talking about Apple. But I can't say that when I faced a difficult decision in my life, I've asked myself, what would Apple do? It just, doesn't serve me. I've asked myself what other people would do. I've asked myself what I think is right. But you know, at no point have I been like, wow, what would Google do in this situation? That's great.  Yeah, doesn't help me.

51:26

Yeah. It's like you can have brands that help prop up your identity, but when it comes to

comes to navigating the complexity of life as a person, you're looking to other people that you admire, not to brands. That would be absurd. In fact, some brand leaders or the founders who help bring brands into the world, we can see these people are very imbalanced. And I would never let  like certain people who are famous, I would never look to them as role models for how to like parent or how to be a good spouse or any of that. So thank you for that. I did not know what you were going to say. It was even better than expected. So Matthew... assuming you want people to find you online, where would they go? And if you don't want people to find you online, that's Okay too.

52:24

Sure. A few places to find me online. LinkedIn is always a good call. I love a cover note with connection request. There's, as you know, there's just so much inbound stuff right now. And it's usually somebody trying to sell you lead generation. So I've got kind of a high fence for my inbound, but even something that says, Hey, heard you on the freelance cake podcast and that was pretty cool. And that should be sufficient to get you over the hump. My consulting website is matthew-fenton.com with a hyphen.So Matthew-fenton.com. And then a few years back, I had a project called Winning Solo, which is not dissimilar to, I think, what you're doing, Austin. I think it's probably one reason that you and I get along, is we see a lot of these questions and answers and issues so similarly. But my goal was just to kind of pass along the best of what I've learned in 25, 30 years of freelancing to those who weren't quite as far along in the path. So that's at winningsolo.com. There is a defunct newsletter. So you can ignore that link, but there is also a pretty healthy archive of five minute reads and about a half dozen longer reads that might be of value to the people that also enjoy freelance cake.

53:40

Great. I will make sure all of those links find their way into the show notes. My friend, I knew that our conversation would not disappoint. It's been such a delight. Thank you for sharing your wisdom and until next time.

53:57

Thanks for having me, Austin. Really enjoyed it.

53:59

Hey, before you go, let me invite you to join our community for more established, advanced freelancers. It's called the Freelance Cake Community. One member named Michelle had this to say, "I'm just so impressed by the quality of the conversation that's happening in the group. The in-depth questions, experiments, and thoughts being shared are just so refreshing and the other communities I'm a part of, it's all beginner questions, which is fine, but it's awesome to find a more advanced space where it's okay to ask more advanced questions." Thank you, Michelle. Here's a little more about the community. Each week we do live group coaching and live coworking. You get access to a massive resource library and obviously the community itself, which we host using Circle. Of course, the people are the best part of all this. It really helps to surround yourself with smart, accomplished and optimistic people who are out there taking risks and building the businesses they really want. If that interests you, visit freelancecake.com/community to learn more and apply. You can find that link in the show notes. I hope to see you there.