From Freelancing to Delightfully Tiny Teams: Embracing Automation, Empowerment, and Emojis with Jenny Blake

What if the traditional models of employment and team building were replaced by a personalized blend of individual contribution and collaboration, which fulfilled and rewarded every stakeholder?
That's exactly what my guest, Jenny Blake, and I, explore in today's epsiode.

As a successful podcaster and author of books including Pivot and Freetime, Jenny brings a wealth of understanding about the changing concepts of scaling and growth, for business leaders who want their work to have meaning and purpose, as well as profit. So she is the perfect person with whom to unpack how embracing automation and individual motivation can lead to delightful team growth and efficient workflow.

From my personal journey of transitioning from the corporate world to freelancing, to Jenny's unique experience of becoming a manager at the age of 24, we dig into the importance of taking that first step from zero to one. How do we best balance team size and individual needs? We unravel this and more. We also peak into Jenny’s use of tools for streamlining processes and keeping her remote team organized, and her innovative use of emojis as a communication tool.

Looking to the future, we muse on how remote work is reshaping the way individuals make career decisions. We touch on the hustle culture and its impacts on entrepreneurs, and discuss the potential effects of external threats like recessions or pandemics on team morale.  Having an emotionally resilent core team that is *just* big enough, might be the key to embracing unknown changes yet to come.

Join us, and let’s explore the future of work together!

Jenny famously does NOT do social media 😎 so check out her wonderful podcasts and three award-winning books, including Pivot (2016) and Free Time (2022);  and the newsletters #PivotList and Time Well Spent.

Transcript

Speaker 1: 0:06

You're listening to the Future is Freelance podcast, the show for solopreneurs, digital nomads and slow-mads, consultants, remote workers, e-residents and people living a life without traditional boundaries. We're here for everyone who defies categorization and makes a living in a life their own way. Every Freelance Friday, we bring you expert tips, inspired insights and stories from the frontiers of freelancing to help you achieve success with your borderless business, whatever success means to you as you live life on your own terms. And today I'm thrilled to share with you an interview with one of my creative business inspirations, jenny Blake. Jenny is the author of books, including Pivot and Freetime, both of which have associated podcasts. In fact, jenny is an amazingly prolific podcaster. Do check out the links in this episode's show notes for all the insights she shares and conversations with a stellar array of guests. In Bodying the Solo Spirit. Jenny accomplishes all this in collaboration with only her delightfully tiny team, and it was that team I really wanted to talk to her about today.

Speaker 1: 1:13

As both this podcast and remote work Europe are growing and my collaborations with other freelancers are deepening and extending, becoming increasingly interdependent, I couldn't get this show out the door without the help of Steph. The remote work Europe newsletter wouldn't happen without Linda, and the level up your LinkedIn challenge is flying along beautifully with the help of Diana. I'm grateful to all three of them, and more so am I still a freelancer. I'm definitely not a manager. My collaborators are all independent professionals, but our work is becoming increasingly intertwined.

Speaker 1: 1:47

So that's where Jenny and I started from in today's core the changing paradigms of scaling and growth, and the human ways to automate our habits, activities and results, even the different ways we measure the success of our collaborations and creations. Of course, we went on from there to lots of different subjects, because we had so much to talk about and it is a slightly longer than usual episode. So do grab that coffee and settle down. I hope you enjoy this conversation as much as I did, and I would love to hear what you think, so do be sure to let us know. Jenny, it's lovely to have you with us here at the Futurist Freelance. Thanks so much for joining us, thank you so much.

Speaker 2: 2:26

I'm super excited to be here. I love the name Well we love your podcasts.

Speaker 1: 2:31

I've been listening to them for a long time. They've inspired my freelance journey. But one of the reasons I really wanted to talk to you today was about your journey from corporate to freelancing to then growing a team once again, what that looks like to you coming from the solo perspective and I love your phrase delightfully tiny teams. So that was something I really wanted to unpack today that zero to one stage that can leave a lot of freelancers Dare, I say it, a little bit anxious. Should I be hiring somebody? Should I keep collaborating with other people? How do we take that bold step?

Speaker 2: 3:10

Yeah well, it's interesting, in looking back, noticed patterns between my ideal team size so the Goldilocks of teams, which is going to be different for everybody, even within corporate. I became a manager very early in my career, when I was 24. And all of a sudden I was managing six people who are older than me and had been at the company longer than me. This was in 2008. And within six months we would need to let half of the team go and they had 90 days to find a new role within the company. And I just started bawling in the director's office when he told me this. Thankfully, my manager was the one that delivered the news, but I was in the room and it felt like such a betrayal of the team members that they had welcomed me to the company and they were my friends and I found it so devastating.

Speaker 2: 3:59

As a highly sensitive person and recovering if even people please are I found the managing aspect of managing people very challenging. I enjoyed the coaching one on one, kind of asking powerful questions, but the admin of managing and the what my friend Charlie Guilkey calls social overhead of managing I've always found draining. So when I was able to pivot internally to back to an individual contributor role. I was relieved and in fact, the one time I've ever been quoted in the New York Times after pivot came out, it was in an article called climbing down the corporate ladder, and it makes me so happy to know that that's the title associated with my name, because sometimes I think we have to grow bigger and bigger, or the right way to be an entrepreneur or a freelancer is to create a team and then a bigger and bigger and bigger team.

Speaker 2: 4:53

And every time my team grew too big I was at peak unhappiness. Even a decade into self employment I had to scale it back down. So I do think that it's important to do what you said, which is go from zero to one, even part time. I say nobody on my team works full time, even me. You need at least one or two people so that your business isn't fragile, so that you don't burn out because you become the bottleneck. It's dangerous to have a business of one and only one, because you can never take a break. If you get sick, there's nobody to pitch in, there's no one who can step in for you, and that becomes exhausting because you're also stuck doing the work you don't enjoy. That's draining that you dread.

Speaker 1: 5:32

Oh yes, I hear you on both fronts there, yeah.

Speaker 2: 5:36

So it is a balance and I think it's going to be different for each person, and I would give you all the permission slip that there's no one right way or one right team size.

Speaker 1: 5:45

Now that makes complete sense.

Speaker 1: 5:47

I suppose I'm at that cusp now where I'm really enjoying the content creation process and starting to outsource more and more little bits of it to people who, where it's outside my zone of excellence, like editing this podcast.

Speaker 1: 6:02

Hello, steph, when you're listening back to this, I know you're going to do a job of making it sound amazing, far better than I could do, far more quickly and professionally than I could do, and I have somebody else helping me with the newsletter. I suppose maybe one of the issues I'm looking at is at what point do those little freelance associations, does it make more sense to have a full time or not? A full time maybe, but as long as you need ops person who's a permanent team member, or can you keep going with people just in their particular role that they do, maybe for a few hours a week? Or what does that do to the social overhead? And even if you don't have to take on that awesome responsibility of their entire income and then being in that position where you might have to let someone go, which you vividly remembered there, it's so difficult. So, yeah, it's a challenging one, isn't it? I'd love to know where the phrase delightfully tiny came to you and at what point it felt that you've got to that point.

Speaker 2: 7:05

That's a reflection of my desire to have a team, but no more than a minimum viable team, as in the absolute tiniest team I could possibly have to do the work that I feel called to do in the world and in my business, but no more. So to me it's delightfully tiny in the sense that it's small on purpose and while I try to create scalable income streams and activities in my business, primarily one to many through my books and my podcast and my private community for small business owners, those are all scalable in the sense that If I have a hundred members or a hundred or a thousand listeners and then I have 10,000 members or 10,000 listeners, there's not that much more work. I'm still doing the same activities. So that's where my idea of a delightfully tiny team comes in. And the podcast is a great example Because I have two shows now pivot and free time.

Speaker 2: 8:02

Pivot I've had for over eight years. In the early days it was all me and I enjoyed that. I love all the nitty-gritty aspects of podcasting. I even enjoy audio editing, but it's incredibly time-consuming 30 minutes of audio to do a close edit might take two hours. So I think people saw me. Now actually, the tools have evolved.

Speaker 1: 8:22

They're much better still takes me two hours.

Speaker 2: 8:26

So when I first started hiring freelancers as part of my podcast team, I still cognitively owned the life of an episode. I was delegating the audio to an audio editor but I needed to give them time stamps, which ultimately still takes a ton of bad bandwidth from me. Then I would delegate show notes to a VA, then I would delegate emailing the guests to someone else and I was still completely the bottleneck because no one owned this process other than me and because of that I have dips and plateaus in the pivot podcast where, for no good reason and unannounced, it just went on hiatus for six months. So it wasn't until I hired, in my case, one stone creative, this full service podcast production team, and I actually Hired them at the highest level I possibly could and I was very nervous because this was the most I had spent on outsourcing on team To that point in my business.

Speaker 2: 9:21

And again, that wasn't till 10 years in. But it ended up being the very best thing I could have done, because they treat the episodes like their own, they are committed to never missing a publishing date and they know that, even if they haven't heard back from me on Listening back to the audio or reviewing the show notes. The show must go live. They publish it anyway. So I'm now not a bottleneck. I'm not in the way the show goes live, with or without me. And if I haven't seen the show notes and it's a cringe for me, well that's my fault.

Speaker 1: 9:50

Yeah, you can fix it afterwards, can't you? And I really like that idea. I'd love to get to that point where all I have to think about is the creating. It's showing up to the, to the recording and so on. And, yes, I think it's. It's going to be one of those mission creep things where I Hired this wonderful person to help with the editing and she's gradually Because she's a small business owner and a podcast obsessive. She will come back and say well, how about this? Have you thought about doing that? Could I help you with this? And it's actually.

Speaker 1: 10:21

It was interesting thinking about the, the theme of when somebody stops being a contractor and starts being your team. There was a conversation with her last week because, as we were saying before we hit record, I've been traveling a lot and she knew I was getting really exhausted. And I had this email from her that said look, I've been thinking about episode seven and you're gonna be really tired when you get back. And so what we could do is this or we could, we could re-release this thing, or you and I could hop on and do a call about this. And I was so touched when I got this email I thought, because I've been a solopreneur for six years and it was well somebody's looking after me and and really concerned about me and that made me feel like I've got a team. It was. It was a lovely feeling.

Speaker 2: 11:07

And that's such a great pointer for anybody listening who is a freelancer. I've how to serve your clients in a way that is so delightful that they recommend you. In conversations like this one and I found the same thing. It's not just doing the work and doing the minimum, it's looking for ways to improve proactively. It's how can I save someone? Next steps, how can I anticipate what their needs are gonna be? Or be so tuned in and attuned, like this person you just mentioned, to be able to say hey, I can hear you're a little tired. How about I take care of the next three steps?

Speaker 2: 11:41

And that is what makes a freelancer indispensable to the business, even if not full-time that you're. You're so good that the person, the mark of any good system or Exceptional team member, is just that. They make your life easier. You can't live without them. It shouldn't be this kind of draining thing, and that's where I think sometimes delegation goes wrong. You don't have the right person, or they're not trained well, or they don't learn quickly, they don't take feedback and therefore you lose trust almost immediately. You things fall through the cracks, so you start giving them less and less. Things are late, they get missed and all of a sudden, you don't want to give them any work at all. That's not, and I've been there. That's where delegation gets really discouraging, because you feel like you've invested all this time and training in somebody and you don't fully trust that they've got you.

Speaker 1: 12:31

Yes, so that's when you feel like you're back in management again instead of creating and collaborating. The ironic thing was the reason I was exhausted last week was I just finished speaking at a conference about the human side of freelancing and Having to be a freelancer in the age of automation, and this was such a beautiful example of something only a human Would have picked up on. All the best systems in the world wouldn't have seen that bottleneck coming of my energy and said are you okay?

Speaker 2: 13:01

Totally, and I would say you can't always just get it right right out of the gate, even with the best attempts. And what I find is, when I am gonna Delegate to someone, I always tell them right from the start document every single thing that we talk about if it doesn't exist yet, and Anything that, any question you ask me, add it to an FAQ. I want you to imagine that in three months we are both gonna hand this off to somebody we've never met and we don't even get to talk to them on the phone. Could they step in and do the work and that way, if that team member wants to move on to other projects or they move on, something happens in their life and you can't work together anymore. You at least have an artifact of your work together. You're not starting over from scratch with the next person.

Speaker 1: 13:45

So that makes absolute sense and this is this is where I love your content, because we're exactly the same alignment on this Documented once you know, do it, write it down, and then you've got that forever, and then you have that single source of truth in your business, in your life that this is where the Wi-Fi password is, or this is the complex procedure for getting a piece of content out of the door, or whatever it is in your business or your life. I really like that, and I do make a point of only working with people who are like that and either have bring their Own systems to the table or understand that the first Bit of help that I will want to get is going to be from a system, and then the humans will come in for the bits that only they can do between, between the automations.

Speaker 2: 14:33

Yes, I have a podcast episode when I had a breakthrough of my own around this called Brain the System, then the Person. I realized that email is such a gnarly area of the business to get help with because it's everything that happens in the business. There is no one thing someone's handling in email. It's everything. It's every customer across every product or service, it's every pitch. It's everything. I realized that I kept training the person, but then I kept starting from scratch. Now this is over 12 years, but I still found it frustrating. So I started creating automations.

Speaker 2: 15:08

In HelpScout, which is the software I use to work with my team in a shared inbox view where we can write notes and assign messages to each other, I started automatically appending instructions. So, on my podcast, if somebody wants to ask a question, they submit through software called SpeakPipe. Well, instead of just telling my team member what to do when a SpeakPipe memo comes in, I set up an automation that helps Scout scans. If an email is coming from SpeakPipe, it appends a note and the note says here are the five next steps to do with this submission. Listen, is it related to the podcast? If not, thank them and let's move on. If it is, download the file, save it here and I would include the link. And I even included a link to the more in-depth manager manual.

Speaker 1: 15:55

I know that you use Gmail tags and things a lot as well to point people that instruction documents and things I know I've listened. The term of listening to podcasts is I'm usually out or doing something and I think, wow, that's genius. And then I don't remember it until I actually speak to you directly months later. So that's no use at all. It's a system, isn't it?

Speaker 2: 16:16

Well, the way that we use tags that's helpful is we make specific actions in the tags so it's not just labeled podcast pitch. We get a lot of those every day. It might be labeled podcast pitch and then another label says JB to decide. Or maybe I see that and I remove JB to decide and I append a label yes or no, and then I sign it back to my team member. They'll know exactly what to do without me needing to even write a note because the tags are so descriptive.

Speaker 1: 16:45

Right. So that's an actual workflow. Then, when you swap one tag for the other, it moves something along in the process that, yeah, I've had a look at this, yes, I'd really love to talk to that person, or not, and then it goes in a different direction. That's brilliant.

Speaker 2: 17:00

Exactly and there are ways to probably automate even that.

Speaker 2: 17:04

In this case I, just like you said, it's kind of manually moves through.

Speaker 2: 17:08

So I change the label and it means that the next person who sees that message right now I only have one part-time team member, faye, who's not on the podcast production team she'll know exactly what to do and those labels can get really intricate. We have one label called add to notion that's where I keep all the documentation about my business and my whole life for that matter. But it might say add to notion or it might say what section of notion, like if somebody writes a nice message, we call those keepers. So we might label the message keepers and another label says add to notion and then I assign it to Faye. Now Faye can kind of already figure out what to do with that. She knows. Now she saves me next steps because she'll read a message like that and just know oh, this is a keeper, I'm going to save this message in our little keepers database and she lets me see it. She just says FYI, and I've already saved it in notion and then I get to just read it quickly and archive.

Speaker 1: 18:02

That makes a lot of sense. Yeah, I really like that. We haven't got to that stage with remote work Europe yet, as it's sort of one mailing list and I'm mainly dealing with the email, but I know at some point I will want to hand that off, at least in part, and to have what I've. One thing I've really learned from you and through everything in the last few years is to try and get the system in first, before the people, and to try and put that structure on it, and we are already going that way with remote work Europe. Even the way we use emojis in Slack with all the different country flags. But this piece of content has been shared in the UK group or the Portugal group and we can tell an awful lot from the flags that pop up and it's visual and immediate. I've got emoji. You've been.

Speaker 2: 18:45

Yeah.

Speaker 1: 18:46

You can do a lot with a good emoji. So there's so much we can do when we make automation our first collaborator and at least to free up the humans for the interesting stuff. But I thought it was really interesting what you mentioned at the top of our call about that kind of emotional time that it takes to manage a team and to support the people. Did you say it was Charlie Gilkey that you'd been speaking to about that? Yes, I also did my cue. Now I haven't listened to it yet.

Speaker 2: 19:18

It just came out today at the time of this recording and it's I'll call you episode 235, on minimizing the social overhead of managing teams, but it's also related. He has a great book called building team habits. That's so good, all the things that I don't naturally think about because I don't naturally think about teams, because it's just called team habits, no verb Team habits. How small actions lead to extraordinary results.

Speaker 1: 19:45

You see, I need to read that, I need to listen to your podcast and I need to read that because I've read some of his stuff on individual productivity, but I haven't read the team stuff because I spent so long thinking I'm never going to manage a team again, I'm getting over my corporate PTSD, but I'm going to survive by being a freelancer till I die. And now I'm starting to realise there are things I still want to do that I can't do on my own and that I will need help with. So yeah, I'm putting that one on my reading list next.

Speaker 2: 20:14

To turn the tables. What would be one of those things, and how did you know that it's something you for sure can't do on your own?

Speaker 1: 20:21

Well, it's the remote work agenda. I have been very happily working remotely as in, not in somebody else's office, for a quarter of a century now and obviously when that started it was very different to what it is today and I've worked mainly from home. During that time and at the end of 2019, I was all set to celebrate my 20 years of working from home with a big book and a Bible and a talk tour and everything, because I thought I knew everything there was to know about remote working. And then, of course, 2020 brought a global upheaval and change and I got thrust into a lot more working one to one with people. Now it feels like we're going through another transition of organisations versus individuals and individual freedom and choice, people being forced back to the office or having to make really difficult decisions about how they want to live their life. We've got record underemployment in the US and the UK and across Europe there are people simply opting out of the workforce and I truly believe the solution to this is choice and flexibility and the ability to work from anywhere. So I want to bring that agenda to the fore and empower people with knowledge and training and information to help make those choices for themselves. So remote work Spain started about a year ago, started to really accelerate that it's a Facebook community, but it's still exploding with growth, and so a few months ago we started to affiliate with other administrators to build remote work.

Speaker 1: 21:54

Europe and the UK group is growing really strongly, and so we're creating content and publications around that. We're in the middle of a LinkedIn challenge, taking a cohort of people through a daily challenge of posting on LinkedIn and engaging with each other's content, because everybody's either a job seeker or a freelancer or somebody who needs to do better building their online visibility because they want to make a change and they're not used to working necessarily in a world where they'll never meet their potential client or boss, and so this is what I want to do, and it's too big. It's too big for me. Jenny, I do need help and I am starting to realise the benefits of that help. Like the UK group is growing. Amazingly, diana, who is leading that group, is also helping me with the LinkedIn challenge, because I suddenly realised well, actually, I do know somebody who's been working in social media for over a decade Diana, can you help me with this? And, of course, it's going brilliantly.

Speaker 2: 22:52

Yay, that's so exciting and that story is a great example of a vision being so powerful that you're willing to lean into a team a little bit and, as you said, even collaborators. It can still be creative how you set that up, but that's the reason. Don't do it, because that's just what a good entrepreneur would do. Don't do it because you're supporting a really powerful vision.

Speaker 1: 23:16

Yes, no, you're absolutely right, and I have spent a lot of that six years in tech journalism and interviewing founders for whom the objective is really scale at all costs, because as soon as you get that funding, you have to start hiring, you have to start getting those user numbers or whatever it is you've been back to do and it just seems I feel so averse to that. I don't want that, I don't know. I hear you. We must reach a point where we can get beyond that. I think it can grow in a different way. I hope it's. I don't know if that's one positive legacy of the whole pandemic time as well, if we can get beyond that hustle culture and that we have to have five, six, seven, eight bigger businesses and we have to keep scaling and we have to keep growing.

Speaker 2: 24:06

Oh, my gosh. I know now there's a podcast called Billion Dollar Creator. Oh, I know I get what they're trying to do, think huge. And yet I just I did a sub-stack article for Rolling Endow of why revenue goals don't work for me and I just kept thinking that a good business owner would have really clear, specific revenue goals. And in fact I also got swept up in trying to earn the elusive seven figures in my business, even just once. And yet the whole process of that just kind of made me miserable and it didn't have me appreciate what I had earned. It was. It just felt so arbitrary.

Speaker 2: 24:48

And I understand that sometimes we do need to hit targets and if you have a team, sometimes that is important. So everyone's rowing in the right direction. But for me personally, as a relatively solo entrepreneur, I don't even call myself an entrepreneur anymore. I don't want to do all those things. I just made a balance sheet post again on Rolling Endow of, filled with emoji. Yeah, you know it was like that's the kind of balance sheet I can deal with. Yeah, just an emoji for each line item. Who cares about the actual math? Just here's a vibe check on every area of the business.

Speaker 1: 25:23

Yes, I love that. Just checking in with the feelings on each line item, right, because?

Speaker 1: 25:27

that's the stuff you can't measure and, yeah, and in terms of the income, I don't. I mean it's it's so. It's such an arbitrary way to measure anything really. I'm at the life stage now where my nest is emptying and, whilst that has lots of complicated emoji stuff, believe me, going on, alongside of it, it's also reshaping. Well, what do I need to earn? What you know?

Speaker 1: 25:50

Could I spend more time giving and putting stuff back now, as opposed to cranking out content that I'm not always completely aligned with, or has it? Does it mean I've truly got to the stage where I only write stuff that I really, really resonate with and for the most part, that's true, and I'm feeling incredibly fortunate that I can do do work that I love and believe in. That it's all aligned around this future of work jigsaw piece puzzle that I'm sort of trying to put together. That will probably be completely unnecessary, I hope, in a decade's time, because we all really will be able to live and work from anywhere and we won't need collaboration or technology or compliance solutions. But right now it's it. There's such an important story to be told there and I don't yeah, I don't want to go back into managing budgets or teams.

Speaker 2: 26:39

Yeah, and some people like the game of that and even the competitiveness of they like setting goals. I used to be like that too, where I loved setting goals and creating really specific visions and then trying to reach it and at some point I just realized, you know, my business surprises me and even when things are tough, try to lean into the energy of what's happening. What I like about what you just said is that the future of work is forever and we'll always have a future of work, in a sense. So that's a great example of a topic that can grow with you over time and pretty much endless, because there'll always be what's coming, what's next?

Speaker 1: 27:16

Yes, I hope so, and that you know the opportunities have only got bigger, just as you think things should be converging towards some kind of an optimal solution for it. There are people building new things and finding new solutions from everything from passporting to technology to make it possible in ways we certainly never dreamed. When I got a new job in 1999, thousand and said I'd really like to work from home because I've got a new baby, I didn't imagine I would never go back to somebody else's office from that point onwards. But that did, at the time, involve growing a team, and I suppose that's the one thing that I still keep coming around to.

Speaker 1: 27:58

We didn't have automation, so we didn't have the technology that we have now. Would I feel more comfortable with humans or or machines doing the boring stuff? I used to hire people to do a lot of really boring work, jenny. When I started growing a remote team, I was hiring people to do data entry and things like that, and even my own start as a freelancer. I was doing stuff that nobody would pay a human to do now, like product descriptions, and I don't know if is it good if those jobs go away?

Speaker 2: 28:31

Well, I tend to think so. I don't know that many people that love wrote data entry, for example. I do think it's fascinating how, if you're early to something, you have to solve it on your own first, and then it takes a long time and it's hard and it's messy and it's kind of jury-rigged together, and then in five years, all of a sudden there's software that'll do it, and now the people entering at that moment in time have it so easy. You know where, oh, we walked up hills both ways in the software snow, like.

Speaker 2: 29:01

I remember I hand coded my first website in HTML and CSS. I taught myself how to do front-end web design. I made it in a text file just to prove a point to myself that I could design a website that way. And then, and then WordPress launch, you know, and then Squarespace, and it just became easier and easier. And even when I started my first website in 2005, social media wasn't what it is now.

Speaker 2: 29:28

If you wanted to say something online, you had to have some wherewithal to get that all set up and make it happen. And then it became where, oh, on social media, everybody's a blogger, everybody writes something in their Instagram caption, and so, and then it becomes harder to stand out, because we're also in a global content marketplace now, which is, of course I hate the word content, but it's kind of true, like we're. It just feels like a free for all a little bit now, because even as a podcaster, I saw that Netflix now offers an audio only way to watch a show or speed up the show, and I'm thinking they're coming in and all these brands of podcasts, and so people only have so many hours a week to listen and I don't want to get discouraged by that.

Speaker 2: 30:17

But it's just interesting to see. No space stays the same for very long.

Speaker 1: 30:23

Yes, and that's. And the other thing is, all these spaces are overlapping. Now we knew where to go in 2005. We wanted to read someone's thoughts, we went to their blog, and if we we want to listen to something, we go to the radio. And now, if Netflix are going to be podcasting and you know everything like zoom and slack eating each other's lunch because everybody's offering video and everybody's offering chat and people don't know which way to go. We were even talking off air about platforms for recording podcasts and video and saying, yeah, this one does this, but this one doesn't do that, and I don't know, is the software just going to eat everything? Will we end up with one super app? Please don't let Elon be right about that.

Speaker 2: 31:07

Oh, yeah, I know, oh, I don't know, I found the creepiest settings in. I rarely, I'm not really on social media, but sometimes someone will send me a link and I sign in Instagram and I saw that it was telling me when my friends had recently been on. I just got horrified Like I don't want to know how many minutes ago so and so was on this app. Like they kind of I don't know took that from Tinder or something. But I went to the settings and of course, it was this labyrinth just to get to the right setting.

Speaker 1: 31:37

Oh, to turn that off. I bet they made that yeah.

Speaker 2: 31:40

Yeah, and so these friends probably don't even know that they're broadcasting when they were last signed in.

Speaker 1: 31:46

No, that's really disturbing, especially a mother of teenagers. That really stresses me out, I agree. I think about this world that they have to navigate and it's really frightening. I suppose at least with an app you can turn it off, and that's the other thing that makes me reluctant to go back to the team management thing again is what you would your moment of recollection in the the boardroom of having to let people go, and I remember, as the pandemic lockdown started, thinking thank goodness I'm not managing a team now. You know I can actually get through this because I can figure out what I need to do to support myself and my household and actually people need what I do, which was amazing. But the thought of having to put people on furlough and stand them down and I know that your business was massively affected by that and I suppose, do we all just have to be resilient about these unknown Black Swan events?

Speaker 2: 32:44

Well, I guess the only option when you're self employed in a way and yeah, we do, and I think these are the moments that we right size our business in a way I tried to keep my whole team even when things were going haywire. I lost 80% of my income in the first two weeks of the pandemic and it still hasn't returned. You know, we're recording this three and a half years later and it's still nowhere near what it was. So it does. I think you know I call it when the financial tides recede. You can either rush out after the tide and try to chase it, and try to chase the old thing, or you take it as a sign to say, ok, well then, what's washing up on shore, what are the gifts that are now visible in the sand or on the shoreline?

Speaker 2: 33:31

I think there's a term for it Muck wracking. I saw there's a book in the UK on muck wracking, this idea of searching for the treasure. Ok, I like that, yeah, and so that's. That's, I think, the opportunity that we have, and some people don't mind having a big team, but it would really freak me out the pressure of that much overhead and having to earn a certain amount yes, just to pay for the team Again. That's one of the reasons I personally my personality does not take well to that level of pressure. I feel like I have enough pressure as it is.

Speaker 1: 34:02

Right. Maybe we just need time to learn that about ourselves. And maybe when you're younger and earlier in your career, it feels like a huge privilege to be given these line management responsibilities and these are your people and and actually you don't realize what you're taking on. And then suddenly there's an external threat, like a recession or a pandemic or something like that, and you realize how little control you've got and these people are looking at you to figure out how they're going to pay next month's mortgage and, yeah, I don't ever want to be in that situation again.

Speaker 1: 34:35

I mean, that's the reason I believe the future is freelance, but also that we just have to maybe somehow get away from this idea of employment and management and the idea that somebody else gives you a list of tasks that fill this random 40 hour week. That is a legacy from the industrial revolution of how we think things should be chunked out. I'd love to see a future where we have a far more blended approach, and I do believe that's what we're heading towards. I know that people on your team don't just work for you. They have other things going on in their own businesses and hustles. I don't know, do you feel like I do that that's the future, that just find different edges, where we collaborate, for the time being, on terms that suit us.

Speaker 2: 35:19

I do. I understand why certain business owners they've described that they experience a very powerful shift when their team is no longer distracted by juggling multiple clients when it can go wrong. Is that okay? Business manager A is ready to do a big launch and the freelancer says, oh sorry, my other client has a big launch then I'm not available.

Speaker 2: 35:42

And so I have heard people say okay, once you get everyone fully, 100% thinking about you and your business, there's a profound change In my mind. I was never convinced that you have 100% of someone's attention. Anyway, I knew when I worked full-time a lot of people had side hustles. And even if I were working full-time for a small business owner, I'd probably have a side hustle, and so I kind of never bought the premise that you ever get 100%. And for me, the reason I don't want anyone full-time is I feel like it incentivizes the amount of time they work that week. Yes, sure, I would rather. Yeah, oh, I have 40 hours to fill, rather than here's the work. How efficiently can I get it done? And you know, there might be still, I guess, if it's a bad actor, an incentive to draw out the work. But we can keep looking for interesting projects, but I don't think anyone wants to work 40 or 40 per week. If I'm being honest, I think a regular work week should be 25 hours.

Speaker 2: 36:45

So we can see our family take care of our health, and so I like working with maybe a contractor who has me and one other client. You know it's nice. You can tell when they get too busy. Oh yeah, and I've made that mistake with a podcast production team Before I found ones. Don't creative. They were recommended by this enormous show and I thought this is the answer to all my problems. I must have hired them right as they were hitting a growth spurt, because you could tell that this is the hard thing about business too. But as a product of their success, they expanded the team, probably too quickly. People weren't trained, they were overwhelmed. Things were falling through the cracks.

Speaker 1: 37:25

So, I've also had some false starts trying to get that balance Is that so interesting Because it's you're observing that at one step away as the client business, but you can see what's going on. They haven't got their team habits ready to scale in that way.

Speaker 2: 37:43

And sometimes I've referred so many clients to a business that they grow. They put me to a new team or something and the work quality just declined so much that we start working together. It's happened more than once.

Speaker 1: 37:57

Business. Yeah, any business can be a victim of its own success in that way. And, yes, I suppose that's the other thing that makes me paranoid about letting go, because most of my freelance work is writing and there's no way I could outsource that.

Speaker 2: 38:10

And then that's a question for business owners Well, okay, how big do you want to get? Do you need to take on every client? Maybe there is a certain sweet spot where you have just enough clients at just the right price and you might have to raise your prices a little bit over time, or maybe a lot bit, but that you just say we don't have any openings, Rather than you know and that's kind of the agency model would just say, well, as many clients as we could take on, we'll hire pods of people to support them. And you can go from having one client to having 100 and then you have 300 team members and I've seen that. But if you the business owner, if that does not spark joy, you don't have to do that. You just cap the number of clients and have a waitlist. And the waitlist is really effective because then you always have a pipeline when spots do open up and the client feels special, Like, ooh, you must be high demand and really good at what you do if you have a waitlist.

Speaker 1: 39:03

Yes, because ultimately, it's you that they want to hire, it's you that they want to buy it. Well, it's the results that you create for them, the transformation, the difference, and that's what we should be quantifying, as you're saying. You know good having somebody thinking that they owe you X hours. What really matters is the results and what they deliver, and, yeah, I really believe that a freelance, independent model is the best way to deliver that, in whatever combination, works for any given circumstance. We can do a podcast with two of us here. We I'm doing the LinkedIn group with somebody else. You have your delightfully tiny team, which I think would have been a great book title as well, by the way. So that's in your recent newsletter.

Speaker 2: 39:45

Yes, that was the title in the proposal.

Speaker 1: 39:48

I liked that because it just summed it up. I mean, obviously free time is a great title too, but especially when you can verb it. But I did like delightfully tiny teams that stuck with me and.

Speaker 1: 40:00

I will keep it with me as I figure out how to scale remote work, europe and going forward. And yeah, I'd love to just wrap up by asking you to get the crystal ball out, if you would, and talk to me about the future of work and teams. Maybe over the next five to 10 years, what do you anticipate things might look like or could look like?

Speaker 2: 40:22

Oh, my crystal ball. I have to conjure this and I love it.

Speaker 1: 40:28

Well, we're all about the future of freelancing here, so what might it look like? We won't hold you to it, yeah.

Speaker 2: 40:36

I had a great conversation with Andrew Davis. It's not just out yet at the time of this recording. I do think that each team member will have their own chat GPT and I think that it will be a great way to learn how to use tools like chat GPT to assist them in their work, to get things started, to edit and revise, to help with research. But I do think that learning how to work with it will become a skill and it will make team members even more effective at what they do and it will free them up to do what they do best. But I think that if people use things like that in a sloppy way, that will be obvious. So I can kind of tell when someone writes an article that's, or a podcast episode, that's too.

Speaker 2: 41:30

Chat GPT ish. It's just boring and it's lifeless and it doesn't have that joie de vie and personal storytelling, and so I do think that it will also be obvious if somebody's phoning it in via chat GPT. And so I see the future of work really continuing. We will have these hybrid teams of freelancers who might work with other freelancers, depending on what aspects of their business, and it will be accompanied by tools that are going to make it all super streamlined. And then we'll have to keep getting more and more creative because the tools will do a lot of the wrote stuff, like even I mentioned podcast editing. The software called Descript that I use you can just do a find all of filler words like um, yeah, like, and find all delete in one click. Now you still need someone to go listen, because maybe some of those removals are choppy and you don't want that, but it's like, in one click you can remove every filler word from a conversation. That was never possible before.

Speaker 1: 42:35

Yeah, that's quite, that's almost scary, but it's. It's true that these tools are simply going to get better and better and it's going to move the edge where humans can make a difference, I think, and keep us on our toes, yeah, and I think it will ask of us humans to be more vulnerable and personal, because there's just not going to be the same need for experts.

Speaker 2: 42:58

I mean, of course we're going to have now experts on AI, but it's going to need to be expertise married with the personal, the vulnerable, the storytelling elements that I know. You know that's not I'm not saying anything new there, but I think that that is how we will differentiate ourselves from each other and from the hands no, that's.

Speaker 1: 43:19

That's a beautiful note to end on, just a reminder of the human as we, as we scale, as we collaborate, as we connect and share and as we move towards future. Jenny Blake, it's been absolutely wonderful talking to you today. Thanks so much for joining us Likewise.

Speaker 2: 43:35

Thank you so much for having you, Maya, and big thanks to everybody who's here listening.

Speaker 1: 43:43

Thank you for listening to the Future is Freelance pod. We appreciate your time and attention in a busy world and your busy freelance life. If you enjoyed this episode, please share it with a fellow freelancer and help us grow this movement of independent entrepreneurs. If you rate and review the future is freelance in whichever app you're listening to right now, it really helps spread the word and that means we can reach more people who need to hear this message. Together, we can change the world and make sure the future is freelance. Don't forget you can check out all our back episodes from other seasons and learn more over at future is freelance dot XYZ. We're so grateful, not only for our listeners, but for the contributions of our wonderful guests and for the production and marketing assistance of coffee like media. This is Maya Midlemish, wishing you freelance freedom and happiness until our next show.