RELEASE DATE: April 15, 2021

Mt. Freelance Podcast - Episode 101

Lisa Prince

Strategist & Founder, School of Ideas

Lisa Prince spent 10 years at Wieden+Kennedy rising to Global Group Strategy Director before she left to “do nothing” for a year and find purpose. She found it creating the School of Ideas and will share how her freelance career took off when she created her own business.

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42 Min

Episode 101 Mt. Freelance Podcast Cover

Episode Recap

In our first full episode hosts Aaron James and Andrew Dickson welcome Strategy Director and School of Ideas founder Lisa Prince to kick off the Mt. Freelance podcast. 
 
Lisa spent a decade working at Wieden+Kennedy, working her way up to Global Group Strategy Director providing guiding insights and ideas on accounts like Old Spice, American Express and Proctor and Gamble
 
She left to spend a year “doing nothing” which led to starting The School of Ideas, her business that helps brands and agencies use strategy and insights to come up with big creative ideas. 
 
Lisa is smart, fun and her interview is a must listen for freelancers considering doing business as a business instead of in their own name, creatives struggling with financial planing, or anyone looking for ideas, insights and solidarity on their freelance path.   
 
The Mt. Freelance podcast is hand-crafted by the producers, mixers and sound designers of Digital One, right here in Portland Oregon, and sponsored by Stumptown Coffee
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Lisa Prince

Episode 101
 
Intro:
This podcast is brought to you by Digital One. Tell your story, connect with your audience and build your brand with an engaging podcast. Learn more at digone.com.
 
Andrew Dickson:
Welcome to the Mt. Freelance Podcast. I'm Andrew Dickson.
 
Aaron James:
And I'm Aaron James.
 
Andrew Dickson:
What's this podcast all about, Aaron?
 
Aaron James:
Well, I was hoping you would answer that.
 
Andrew Dickson:
We are going to bring in a premier creative freelancer, and we are going to interview them so that you, our listener and you, Aaron learn more about freelancing.
 
Aaron James:
I think as we have created Mt. Freelance, which is a course, community, and now a thriving podcast to learn about the craft and business side of freelance, I think one thing we have learned is that there is a lot to learn.
 
Andrew Dickson:
You know what we should do after the interview is we should answer a listener questions so that we can actually offer some of our own freelance advice, because we've been doing this for a while. Haven't we?
 
Aaron James:
Yeah, we have. Over time, I think we've picked up a few tricks of the trade, a few hacks. We're willing to share. The whole idea is that this isn't a secret anymore.
 
Andrew Dickson:
I'm pulling up the Mt. Freelance website, which you designed and I wrote, and it says here, "We have over two decades combined freelance experience working for some of the biggest brands and agencies in the world." Is that true?
 
Aaron James:
That is true. And I will give you a podcast high-five.
 
Andrew Dickson:
Who're we talking to today, Aaron?
 
Aaron James:
I'm going to give you a hint. I'm going to say one word, strategist.
 
Andrew Dickson:
A professional chess player.
 
Aaron James:
No.
 
Andrew Dickson:
A strategist in the advertising arts-
 
Aaron James:
Yes, yes.
 
Andrew Dickson:
... Someone who comes up with the idea, the insight that leads to the new brand, or the new advertising campaign.
 
Aaron James:
Now I'm going to say two more words, British accent.
 
Andrew Dickson:
Lisa Prince.
 
Aaron James:
Bingo.
 
Andrew Dickson:
We got Lisa Prince in the house.
 
Aaron James:
Oh, hey, Lisa. Why are you here?
 
Lisa Prince:
Because I like you.
 
Andrew Dickson:
And you said, "Yes," when we emailed.
 
Lisa Prince:
I have nothing else to do this afternoon guys, and you're nice people to hang out with.
 
Andrew Dickson:
Double win.
 
Andrew Dickson:
So Lisa, when you meet someone for the first time, say at a cocktail party, what do you say that you do for a living?
 
Lisa Prince:
God, you're hitting me with the hardest question right off the bat. So, I'm a strategist, which of course means then I have to spend five minutes explaining what I do. So, you've hit the nail on the head. So people go, "What is that? Business strategy? Management strategy?" And I say, "Well, basically if you have a company and you need to tell a story about that company, and figure out what your story is and how you're going to use that story to keep your business afloat, I'm the person that helps you figure that out, and how to turn it into money. And not just turning it into money, I suppose, but turning it into something useful in the world too. And then I take that story, and I translate it for all the people it needs to be translated for. So, internal staff, product designers, creatives in an agency, whoever needs to be clear on what that story is." And I find that personally as a brand strategist, the easiest way to explain it.
 
Aaron James:
So there is a lot of preparation that goes into understanding a brand. Can you tell us what that preparation is?
 
Lisa Prince:
To start that, I think one of them is... Because I work with a lot of people now outside of advertising agencies who're new to this, and I think one of the most misunderstood things about strategy and creativity is that they're considered to be enemies rather than bedfellows. So, the strategy is going to get in the way of creative freedom, and then creative freedom is going to get in the way of being strategic. And actually, I find they're just not often used together in the right way. And I think what people misunderstood is that creativity actually thrives on a little bit of rigor. So, I'm sure as creatives here, the worst brief in the world is just do some cool shit, right? Without any direction, problem to solve sort of parameters in which you're working with, or areas to go explore.
 
Lisa Prince:
So, I think of the strategist almost like a pig who hunts for truffles, and you have to go find the good truffles. So, I think the process always begins for me with strategy, with what is the problem we're all trying to solve here? And we all know the adage, like a problem well-defined is a problem half-solved. And I think we know it, but we don't live it, right. So, if we can spend half the time, even two-thirds of the time on really understanding what the problem is, then the rest of things fall into place really quickly.
 
Andrew Dickson:
So, as far as your career, I'm imagining you started as a junior strategist. When did you kind of get the keys to the car, and really get to run a campaign by yourself?
 
Lisa Prince:
I'm trying to remember that moment. I think five years in, I was just given an opportunity to work on a pitch by myself, and just given a chance to see if I could fly on my own two wings, and I was really ready then. But of course, made all the mistakes that people make when they're kind of going on their own, right? Just not being able to read a room really well, maybe not having the emotional intelligence that goes with the job and all of that good stuff.
 
Andrew Dickson:
And then we, of course know you because we worked together at Wieden + Kennedy, Portland, but you started, obviously at Wieden + Kennedy, London.
 
Lisa Prince:
So, I was at Wieden + Kennedy, London for five years, and we had a kid. We had Edie, who's my oldest. Hi, Edie. And she was one, and we were living in a tiny flat in London, you know how everyone does, like in the big cities. And we were like, "What are we doing? We can't live in this tiny flat with a baby." And it was one of those moments, we were like, "Well, I either get a bigger job and a bigger house than I'm never in, because I'm at my bigger job, or we do something different." So, I asked for a transfer to Wieden + Kennedy, Portland. And in the classic chaos of Wieden, I was interviewed like 15 times at Wieden + Kennedy, Portland when I flew out for the day.
 
Lisa Prince:
And only on my last interview, I think someone realized they actually already worked at Wieden, and they didn't need to interview me so many times. Because everyone just kept showing up to chat with me, and I was like, "This is a really big interview, considering I've worked here for five years." But that's Wieden for you in all its charms. So yeah, I came out to run the strategy on the P&G Thank You Mom campaign for the Olympics, which was turning a... What had been effective, but pretty small campaign into something Olympic worthy.
 
Aaron James:
So, what inspired you to go freelance?
 
Lisa Prince:
In full transparency, it was a total midlife burnout. So, I took six months off, and I decided to... I'm quite an A type personality, so this was a bit of a weird thing to tell myself, but I was like, achieve nothing, just like nothing. I wanted to meet people in six months and they go, "What have you been doing?" And I say, "Nothing." "Anything interesting?" "No, not really." "How are you doing?" "Fine, I think." And I was super grateful for that experience, because I basically spent six months tidying my basement and not talking to anyone apart from my family. And that was wonderful.
 
Lisa Prince:
And in that time I thought, "Oh, I'm going to be a stay-at-home mum who works a little bit." And it's funny how I've definitely found an incredible amount of balance, but I'm not a stay-at-home mom who works a little bit, and that bit didn't transpire. And I think that was probably just an overreaction, its your burnout, so you're like, "I'm never going to work again." And then you kind of right the ship, and you're like, "Actually, I would quite like to work a little bit in some interesting stuff."
 
Aaron James:
Okay. So you laid yourself off?
 
Lisa Prince:
I laid myself off. I love that.
 
Andrew Dickson:
That's a T-shirt right there. The Mt. Freelance T-shirt. Get those made.
 
Aaron James:
Andrew and I have fun with the fact that our freelance career started by being laid off. And it's actually pretty common. A lot of people, there is a sense of security that comes with a full-time job that's only a sense. And I think when you go freelance, you realize, "Wow, there's a lot more to do here, but I have a little bit more control over where this is headed."
 
Lisa Prince:
Yeah. The next way I talked about this break, and this was really helpful for that cocktail party conversation. So, if someone wants to use this, go right ahead. I said, "I'm having a walkabout period," which is basically how to... So, what I said is, "This industry is changing an awful lot, and I don't know where my place in it is, or where I want to be. So, I'm on a walkabout period where I'm going to explore all the different places I could be, and figure out what I want to do and learn from those experiences," which is just a really clever way of repackaging. "I don't know what the fuck I'm doing, and I'll take any job that comes."
 
Andrew Dickson:
Good branding.
 
Lisa Prince:
And that's what I did for the first year I took. I really said yes to everything. Some experiences were sexy and great, and some were unsexy and not great and some were unsexy and great, all the different permutations.
 
Andrew Dickson:
So, yeah. Tell us about your current project, your business or your consultancy.
 
Lisa Prince:
Yeah. So, before I left Wieden + Kennedy, I'd run a small program called Strategy School where I was doing something quite similar to what I'm doing now. And that was great, because that taught me that this is something I really loved. So, all the skills, obviously you mentioned this earlier of strategy, being able to translate things, make them simple, take complexity out of things are basically the skills of teaching as well. And so, I saw this next generation of strategists coming up, and even creatives, anyone working in this field. And I couldn't help, but feel like, "Oh, if I could just share 10 things I was taught, I could make their jobs a lot easier."
 
Lisa Prince:
And so, during that time, I was approached by an agency who said, "Hey, could you come train our people? You have a training company, right?" And it was one of those moments where you go, "Yes, I do." And then you quickly build a website over a weekend, and register an LLC and all of that stuff, which is exactly what I did.
 
Andrew Dickson:
Wow.
 
Lisa Prince:
So, I said, "Yes, I do have a company, it's called..." Actually, I didn't even have a name, I'll tell you a funny story about the name. But, "I do have a company, and I'll send you a proposal and our website on Monday morning." And we built a website in a weekend, and our company is called School of Ideas, and we work with companies, agencies, anyone who will have us, frankly, to teach the practical tools behind big ideas. And so, when I was trying to work out if it should be a strategy school or a version of that, or School of Ideas, I decided to go to Powell's bookshop. And I said, "If the section on strategy is big, it's Strategy School, if the section on ideas is bigger, it's School of Ideas. And the strategy section was three books, and the idea section was like a whole sort of corridor. So, I was like, "Oh, School of Ideas."
 
Andrew Dickson:
School of Ideas wins.
 
Lisa Prince:
Yeah.
 
Aaron James:
Well, I think strategy had three books, planning had one, so you kind of worked your way into it.
 
Lisa Prince:
That's true. And so, we showed up to that agency and we first started working with agencies.
 
Andrew Dickson:
And who's we? Just so we...
 
Lisa Prince:
Yeah. So, I'm partnered with my wonderful partner and best friend, Hanna Nesper Newell, who we also know from Wieden + Kennedy. She's the managing director. And we've been doing this for four years now.
 
Andrew Dickson:
It's been four years? Wow.
 
Lisa Prince:
It's been four years since we've been doing this. And it's mostly going really well.
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Andrew Dickson:
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Aaron James:
I'm not sure, actually.
 
Andrew Dickson:
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Aaron James:
Oh my gosh. So, it's like a magazine.
 
Andrew Dickson:
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Aaron James:
Do they grind it?
 
Andrew Dickson:
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Aaron James:
Oh my gosh. Could you bump that up to half off that first order?
 
Andrew Dickson:
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Aaron James:
Okay.
 
Andrew Dickson:
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Aaron James:
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[End Advertisement]
 
Aaron James:
So, what is your process for keeping the work, the projects, the engagements coming in?
 
Lisa Prince:
Feeding the pipeline, right?
 
Aaron James:
Yes.
 
Lisa Prince:
Yeah. Our situation is somewhat unique, because it takes a long time to sell our program, right? Because it's not... It falls into the bucket of training, which is unfortunate for us, and we need to work on that. And that is seen as a luxury, when actually it's not a luxury. This is really important. And so, we have long lead times, but then once we sell our program, it's profitable for our business. The best way I can describe it, is its kind of like a real estate model, work, work, work, work, and then sell a house and get a commission. So, I bought a book on how to feed the pipeline as a realtor.
 
Andrew Dickson:
Smart.
 
Lisa Prince:
Because there's lots of books on that. And one of the things that really came out to me from that book, but it's a bit of a no-brainer is just fostering your relationships. And I don't want everyone to be a sales person, but I think if I can just nurture relationships with people I like, and just talk very passionately, because I am passionate about what we do, the Venn diagram of their needs and what we offer will crossover at some point. So, I just tried to stay in contact with all the people that I am in contact with, and I just really try to nurture a proper relationship, not a salesy relationship, but  like a human-to-human relationship like, "How are you? How are your kids? I care about you, and let's go out for dinner. You're a good person, I'm a good person. Let's stay on top of what each other need."
 
Lisa Prince:
And then I nurture that, even knowing that that may never translate to business, or it might translate to business in a year or two years time, but just consistently plugging away at it, because they'll always come a point where someone's like, "Oh, I have a need." And then you want to be present when they have a need, right? And it's all about having a ton of integrity. So, I nurture my relationships, because you never know where a lead comes from. I've even looking, Andrew here, because I think I got a lead from you standing in a swimming pool, the summer pool, Creston summer pool, you're like, "Hey, you should check out this agency. They're looking for someone." We were both ankle deep in water.
 
Andrew Dickson:
I'm remembering that. Yeah, yeah.
 
Lisa Prince:
By the kiddie slide, right? So, that's like, you never know where leads going to come, so just be a good person and maintain your relationships. And I'm really big on that for life as well as business. And then also I think it's as much about what you don't do as what you should do. So, I'm very clear on who we may not be right for, and I focus on the people I think we're going to be right for and I'm very upfront with that, with people. So, sometimes people call me and I go, "Look, you shouldn't work with us. We're way more than you need, or we're going to be too expensive for you, or your problem is not actually what we solve." And so, I've said as many no's, as I've said, yes.
 
Andrew Dickson:
When you say no, do you have people you refer them to?
 
Lisa Prince:
Yes. Always, always. And that's a great... So glad you brought that up.
 
Andrew Dickson:
That's Mt. Freelance 101, yeah?
 
Lisa Prince:
Yeah, because that's also fostering relationships, right? So, it's a win-win for everyone, because I always do that. I have a handful of people who I know who're really good at all the things that I get asked for a lot that I'm not best served to do, and I'm always recommending. And then they recommend back, but even if they don't recommend back, you still are providing a service, you're being helpful to that contact. So, they're like, "Great. You're not the right person, but I still think of you as a really useful person, because you connected me." And so, then you get stuck in their brain as being a useful person, and they come back to you again for other stuff. So, I think that's a huge part of this.
 
Lisa Prince:
And then the other thing is just plugging away at it, like feed the pipeline. I think the biggest mistake we made, and I'm sure a lot of freelancers feel this, is not feeding the pipeline when you're busy, and then suddenly coming out and realizing you didn't feed it, so there's no jobs and it's going to take three months to get it up and running. And so, I've got much better at the high of a project, always thinking about what the next project's going to be.
 
Andrew Dickson:
Aaron often suggests, when you are super busy, that's the best time to reach out to other clients like, "Hey, I'm really busy now, but I'm just saying."
 
Lisa Prince:
So true.
 
Aaron James:
But, I'm just saying hi, because even if you had work, I couldn't possibly take it.
 
Lisa Prince:
I would say that one thing I've learned is a no is a very attractive thing to people as is, "I'm too busy right now." Because I think it's just human nature that they go, "Oh, I don't want to be turned down. This person must be really good." Or, "I want the person who's busy, because that means they're really good."
 
Andrew Dickson:
Right. Versus, "I'm absolutely free. I can come at you however you want."
 
Lisa Prince:
Yes. Yes.
 
Aaron James:
I'm actually at your front door right now.
 
Lisa Prince:
Yeah, yeah. Yeah.
 
Andrew Dickson:
So, one of the things that often gets discussed in our member group is whether to go by your own name or create a business that you can work behind, and you've gone the business route. Talk a little bit about what that has afforded you or opportunities that that's opened up.
 
Lisa Prince:
This is a world where perception and reality are sometimes two different things, right? So, you have to be very confident of your value. And I think especially as women, we hugely underestimate our value. So, first is that putting your big girl pants on and being like, "I'm going to stay on this phone. I'm going to throw my rate out. I'm going to let the silence hang there. I'm not going to quiver. I'm just going to go 'Mhmm. Yep, that's what I'm worth." And that takes a lot of training. I think putting a company behind it allows you to abstract it a little bit from yourself, so you kind of feel like you can be more confident, because rather than saying, "Lisa Prince is very expensive, but very fast," which sounds horrible. You can say, "School of Ideas is not the cheapest thing on the market, but also we're incredibly fast and efficient and you're going to get your value back in a multitude of ways."
 
Lisa Prince:
And so, I think it allows you to have quite tough conversations in an easier way. I also think there's a perception that you're bigger, which... So, I've been in a few situations where a managing director has been standing up talking about what School of Ideas has done, or what they're going to do. And I sit there smiling, because I'm like, "You're really just talking about two people or three people." And I include my wonderful husband who does all our design, and three people around the kitchen table. But when you stand up and say, "School of Ideas delivered an incredible-"
 
Andrew Dickson:
50 people nodding their head.
 
Lisa Prince:
Yeah, it sounds like 50.
 
Aaron James:
"Gosh did that come from Floor Four or Floor Five."
 
Lisa Prince:
Yes, yes. So, I definitely think that that helps hugely. And also as we've grown, it's been really nice to step back and let other people have a voice in this. I don't have to be on top of all of these decisions, and it gives us flexibility to bring in other people in the future. And we already do that, sometimes we're five versus three. So, that's given us that option.
 
Aaron James:
Okay. Fast forward, in five years, do you see this as a 30-person company?
 
Lisa Prince:
Absolutely not. So, my aim in life which is actually surprisingly difficult is to be moderately success. It's easy to fail, and I think in some ways, it's easy to go big. And what I mean by that is to scale up and grow, and chase that and go after it, and I say that, because if you come into a company and you're effective and you're good, they want to give you more work. And some of these projects will be really big. And I hear that monkey in my ear who's like, "Well, staff up, and take on the really big project." But then what I'm always trying to balance this with is the life that I actually really want to lead, and that's the whole reason I wanted to work for myself so that I could live the life I wanted to lead. And the life I want to lead is not working all the time.
 
Andrew Dickson:
What are some of the challenges? You mentioned the pipeline, but what have you found anything else challenging about freelance?
 
Lisa Prince:
Oh my God, so much. I had this great quote, which I'm sure you guys have heard several times that, "Anxiety is the price you pay for freedom." And I think that sums up this life so much, right? so, I worry all the time. So my number one challenge with all of this is I'm constantly worried about money. I'm constantly worried when the next job's going to happen. And even if I have three months booked out, you're always then, "Well, what's the next three months going to look like?" And even if this year is starting to look good, you're like, "Well, what does the next year look like?" And I've realized after five years of doing this, I don't think that goes away. I don't think you ever get to put a stamp and go, "Oh, I've made it now. It's all coming through smoothly." Certainly not when you're trying to be moderately successful.
 
Lisa Prince:
And so, that constant anxiety haunts me, but I know that's the price I have to pay for this life. I get to control my schedule. I get to be a good friend. I get to see my kids. I get to rest. So, I try and build in genuine periods of rest and reflection. And you know what? I've made my numbers for a few years now, and so this doesn't come from a place of rationality. It comes from just pure fear.
 
Andrew Dickson:
So, you have numbers? Do you set goals on how much you all want to make?
 
Lisa Prince:
Oh my God. Do I have numbers? I have an Excel spreadsheet for everything. I'm the daughter of a financial planner, so I bought that, The Freelancer's Bible. I'm sure you guys talk about it, and it has the calculation of your day rate, include benefits, include sick days, include... Yeah, I always calculate, I'm a strategist. I calculate the financial goal I want to make for the year, my plan for getting to that goal, like what type of balance of work of consultancy and training, and then also, because I like to build in a couple of months off, it's not really off, a couple of months thoughtfulness over the summer. I have to budget for that, right? So, from a cash flow perspective, I have to get that money in ahead of time, so my year is quite front-loaded with work so that I can take that time in the summer. And so that takes a lot of planning.
 
Lisa Prince:
So, yeah, I have one of those girl scout, countdown things where I have a figure for the year. This is very satisfying by the way, I recommend this. I have an Excel spreadsheet. I write the figure for the year I need to make, and then every time I get paid, I dock that figure, right?
 
Andrew Dickson:
Ohh that's cool.
 
Lisa Prince:
And so, I can see a financial goal. Maybe I should do it the other way. I prefer it going down to zero, because the minute it goes down to zero, I know I can play, right?
 
Andrew Dickson:
And everything else is just gravy.
 
Lisa Prince:
And everything else is going to be good.
 
Andrew Dickson:
Yeah.
 
Lisa Prince:
So, I find that very satisfying.
 
Andrew Dickson:
Very cool.
 
[Begin advertisement]
 
Aaron James:
Andrew.
 
Andrew Dickson:
Yeah.
 
Aaron James:
Do you need to spice things up in the kitchen?
 
Andrew Dickson:
Not anymore, because I have several bottles of Bobbie's Boat Sauce.
 
Aaron James:
Oh, Bobbie's Boat Sauce. Isn't that the sauce that's like Ketchup Sriracha fish sauce, and they all got together, and started a full rock band in your mouth?
 
Andrew Dickson:
Yes.
 
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[End advertisement]
 
Andrew Dickson:
What's next for School of Ideas. Are you guys going to do your own podcast or what's?
 
Lisa Prince:
This is a really, once again a really interesting question. So, I talk about the three Ps in our business. I talk about pipeline, projects and platform. And the platform piece of it is building a platform, because I realized no shit Sherlock that you have to be out doing stuff to make people aware of you. And probably the biggest mistake I've made in my career is a typical female, which is like, "Well, I don't need to be the name. You go out in front, and I'll just do the thinking and the work, and you talk and do the stuff, and I'll be behind." And I've kind of reached a point in my career where I'm like, "I have lots of things to say, so I should start saying them."
 
Lisa Prince:
And also this is a win-win, because it's going to draw attention to our business, and then it's going to get us in front of more people we can teach and their jobs are going to become easier, and they're going to be sending me notes saying, "Thank you. You made my job easier," which is what I love. So, what I'm going to be doing at School of Ideas is working on the three Ps, right? But also the platform piece of it's really hard, okay? Because it's a lot of work, right? Giving away stuff for free, like doing a podcast, writing an article, keeping up a newsletter, I struggle with a lot of it, because I'm kind of like, that is a lot of work that you aren't paid for, and do you really see it come back?
 
Lisa Prince:
I do think a lot of us in advertising especially, are so excited by creative concepts, we don't always think about the value to a business behind it. So, we have a motto, work smarter and not harder. And it's because of what we teach, we want people to work smarter, not just harder, and we try to live that too. So, there's a lot of things we don't do. I don't have a Twitter account, because I actually think that's quite time consuming for me. I would get sucked into it, and it would take me away from being able to concentrate on other things. So, that's a decision I've made for good or bad. And I very cautiously use Instagram. I'm trying to write more articles, and trying to do more podcasts and things like this, but they are... Let's say, this has been a lovely use of time... Writing articles is quite time-consuming, because I want to do them really well, and that takes time.
 
Lisa Prince:
So, trying to figure out the platform piece in the most efficient way, and also the most enjoyable way is really a huge nut to crack. I was given a great piece of advice where I was like, "Fuck, I don't have a content calendar. Do I need a content calendar?" And it just filled me with dread. It just felt like it was hanging around my neck. And then someone said to me, "Fuck the content calendar, just write when you want to." And I was like, "You know what? That's really good advice." So, I'm trying to live that. But unfortunately we're really busy right now, and so it's really hard to write articles or Medium posts or whatever, so I struggle with that. I haven't cracked that at all. So, hopefully this podcast counts for like a month's worth of content calendar, right?
 
Aaron James:
Oh, yeah. This is your spring content.
 
Lisa Prince:
So, that's a really hard piece, and I'm sure that's something that freelancers and consultants struggle with too. I do see the benefits of it. Of course, I see the benefits, but I think what I'm trying to work out is the sweet spot where the benefits have worn off, and the work is too much, right? You've got just the right amount of work for the benefits and the enjoyment, but not a bit more.
 
Andrew Dickson:
So, you are going to all these different companies all over the place and you're a strategist, what are you noticing going on right now in the workplace?
 
Lisa Prince:
What I've become obsessed with is less about what everyone's latching on to in culture or like what brands should chase and what they should talk about, and more about the work habits that are challenging creativity. And the number one challenge I see to creativity on the agency side and the client side, and in terms of quality of life and quality of thinking is been completely encapsulated in Cal Newport's book, Deep Work. And I love this phrase so, "The death of deep work is the number one trend I'm seeing." And what that basically means is deep work is classified as concentrating at your highest level on something that really matters and without distraction. So, for me, that looks like a five-hour day where I'm writing a presentation and really thinking hard about it, or digging into research and really thinking hard about it.
 
Lisa Prince:
That doesn't happen in companies anymore. So, people are booked solid and meetings back-to-back, or when they come together to solve a big problem, it's like a 45 minutes, right? We got to crack this in 45 minutes, and during that time, they're responding to email, they're responding to text messages, they're updating a Slack channel, and it's like all these distractions. And so, the big strategic thinking that needs to get done, the go slow to go fast, if you like thinking isn't getting done, because no one has time for deep work, and it's not rewarded either, so we're all rewarded on our reactiveness and productivity is now judged on how quickly we respond to things.
 
Andrew Dickson:
Yeah. "I saw you're off Slack for five hours. What was going on?"
 
Lisa Prince:
Yeah. So, that I see in virtually every place I go into, and that is why people aren't able to come up with really good big ideas anymore, because they just don't have any time to think.
 
Andrew Dickson:
To me, that's really been the gift of freelance. When I was at Wieden + Kennedy, there was never time... You always had to be partnered with someone and with multiple people. And yeah, I love that I get these times to think, and really it's fun. It's fun when you have that time.
 
Lisa Prince:
It's a gift. So, I couldn't agree with you more, and I'm late to realizing this, right? So, that rest period I was talking about in life, you've read the books. You've thought about stuff, I have a chance to look at culture overall. And you come into a company, and what I've realized now is the superpower is being rested and undistracted. So, you're like, "Hi, I'm fresh, and I'm going to think about your problem for the next week, and I don't need to be on the Slack channel. And no, I don't want the company email address, and you'll know where to find me." And that is such a gift, but I would say it makes you fast, and so, once again, I'm so hot on making sure that we're getting paid our value, that the value you're delivering in a situation like that is not just the week that you're spending there, but the three weeks you've had off doing all the thinking and research.
 
Andrew Dickson:
Or the 20 years that you've spent.
 
Lisa Prince:
Or the 20-year career building it. So, it's making sure that that comes through too, right? Because also, people are working harder. They're actually working harder to achieve less.
 
Andrew Dickson:
When there's an arms race with all the tech companies trying to solve it, but I think they're almost making it more difficult. That's every tech client I work with is like, "We're solving work."
 
Lisa Prince:
And you know what's the horrible bit about this is that I say to myself now, "Oh, I'm unhirable now," because it's not just a lifestyle thing, I'm just not convinced work works anymore. So, I can now see it's a system that's broken, and therefore I don't want to take part in it, because I don't actually think it creates the best output. But that's probably a conversation for another day, because that's a whole other subject.
 
Aaron James:
That's like the dark Mt. Freelance. The dark side of freelance.
 
Lisa Prince:
It's all broken.
 
Andrew Dickson:
Well, Lisa, thank you so much for coming on the Mt. Freelance Podcast.
 
Lisa Prince:
Thank you guys. I've loved this. Thank you.
 
Aaron James:
Yeah. Thank you.
 
Aaron James:
All right. We have the exciting part of the show where we get some questions from some of the great folks that listen to this podcast.
 
Andrew Dickson:
I can't wait.
 
Maggie Peng:
Hi, Aaron, Andrew and guest on the show. My name is Maggie Peng. I'm currently an advertising senior at Syracuse University, interested in doing strategy after graduation. And I'm curious, what do you think are the on obvious pros and cons of freelancing? Something I wonder is, do you ever struggle with finding a sense of belonging, because you don't work at one company? Thank you so much.
 
Andrew Dickson:
Ooh, good question, Maggie. What do you think, Aaron? What are some of the unforeseen pros or cons of being freelance?
 
Aaron James:
Well, maybe this is obvious, so maybe it's seen, but there's no cap on what you can earn if you freelance, other than your own abilities and time, but you aren't stuck with a set amount that you're making.
 
Andrew Dickson:
You can also, you can work... I think what I love about freelance is you can literally work for anyone and for any brand, any small business, any person, any non-profit. So, that sort of freedom is pretty incredible. What about a con?
 
Aaron James:
There's a little less infrastructure around, or way less infrastructure around your business. Obviously, we advocate creating a little bit of infrastructure yourself as it is your business, but a lot of the things that are taken care of in a larger business or an agency or design shop or that type of thing aren't there. So, you do have to roll up your sleeves and wear many hats.
 
Andrew Dickson:
My IT department is apple.com. Sometimes it takes quite a while for them to get to my ticket.
 
Aaron James:
So, a lot of those things, if you are a tinker, you're adventurous, you want to roll up your sleeves and solve problems, freelance may be a really great avenue for you. I also think being able to control your price of what you charge is really, really big. And as you get better at it and understanding what the market bears, yeah, you can make more, you can charge more, you can demand more, which is great.
 
Andrew Dickson:
For the first couple of years of freelancing, that's when you get really good, that's kind of the fun part.
 
Aaron James:
Yeah, it is. And I think we've always talked about students and before the pandemic kind of discouraging them from going straight into freelance. It's better to kind of build your network, build your experience with other shops, other places that you can work where you can kind of learn from others. But right now, that's not necessarily an option, because of how strange things are right now. So, a lot of students are going straight into freelance.
 
Andrew Dickson:
And then, as far as that second part of the question, I think there's been times where I've felt a little lonely, usually when I'm the only freelancer on a longer-term project, and you are the lone freelancer working with a team that maybe has been working together for a couple of years, but that's what a great lead into why we started Mt. Freelance.
 
Aaron James:
It really is. Maggie, we'll send your prize later. But, one of the things we've always talked about is you need community. You need to be able to bounce things off of people and run ideas, and proposals and things by people. And really, that's what Mt. Freelance is. If you join the membership, it is built around community, and so it's learning, but it's also learning as a team and learning as a group. And that's an incredible network to kind of tap into to make sure that you don't feel alone. Thanks for that question, Maggie.
 
Andrew Dickson:
The Mt. Freelance podcast is hand-crafted by the producers, mixers, and sound designers of Digital One, Portland, Oregon, executive producer, Eric Stolberg, post producer, Kelsey Woods, assistant engineer, Tristan Schmunk, who also created the theme song and instrumental music. To learn more about Aaron, Andrew, and Mt. Freelance, visit mtfreelance.com. Thanks for listening, and may your day rate be high and your vacations long. 
 
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