Reflections: One year of freelancing, experiments & other people's reactions

[01:00] Paul: Welcome to The Boundless Podcast. I'm Paul Millerd, and I created this podcast because I'm passionate about making sense of the future of work and having conversations with the innovators, creators, and thought leaders who are carving their path in today's fast-changing world. You can check out the podcast and more on boundlesspod.com.

[01:21] Reflections: So today's episode is a bit of an experiment. I am just going to be talking to myself today. It's both a challenge and just experimenting with new formats. So wanted to give an update on a few things. One is just one year into freelancing. What is it like?

What are people's reactions? What do you— what have I learned that I haven't expected? So there's a number of things along that. I think one of the biggest surprises for me in the positive direction has been that it has far exceeded some of my expectations. So going into it, I think I was a bit nervous. I was a bit bold.

I was pretty sure it was the right path for me, but I wasn't really sure what to expect in terms of day-to-day spending my time. How would I get projects? How would I get clients? And I've actually found that hasn't been the hardest thing. I'll get to that. But I think one of the positive things has just been the freedom of how I spend my time.

The shift from full-time to working on my own has been much more dramatic than I would have expected. Uh, when you're working for your own, working for clients, working on specific projects, there are really no meetings. And especially if I'm paid on an hourly basis, there isn't really an incentive to have meetings or not be efficient about decision-making or moving forward with working on things. A lot of the reasons freelancers are brought in is because they're timely and are available on Monday as opposed to trying to hire somebody a few months from now. So the upsides have just been the freedom to work on what I've wanted to work on. So one of my first projects was a several-month project and it was working with MIT.

I was working with a professor there helping to launch a nonprofit and build a bunch of different tools. The way we worked out the contract was I was on the hook for up to a certain amount of days. What that didn't mean was I show up for a number of days and basically be in an office, be available. What it was was, here are the problems we need to solve, go do it. Uh, so there was a lot of freedom on how to do it And given that I had so much freedom as an independent contractor, you can bring in other freelancers, you can use other people. You also just have to be resourceful to solve problems that you haven't solved before.

I was given a lot of autonomy over how to do that. So one of the biggest challenges was how do you structure your day? When do you wake up? When do you work out? When are the times when you can be most productive? And I found it's varied.

I'll go through different spurts. Sometimes I will work productive in the morning. Sometimes I'll just get in spurts where I can do a lot of things, be pretty productive at night. But I haven't really found a steady rhythm. In terms of hanging out with other people, I've generally tried to stick to a similar Monday through Friday schedule to do work during the day because most people are on a Monday through Friday schedule. So hanging out with them in the same times is definitely a priority.

Since I'm not working with colleagues, I still need to invest in a social life. So one of the biggest challenges I did not anticipate was the fact that the shift from a full-time paradigm to working on my own is much more dramatic than I anticipated. What does that mean? It basically means I had to rethink my entire definition of success. Or at least define one for the first time in my life. I had to figure out how much money I wanted to make.

So when you're working full-time, you don't decide how much money you want to make. Now, you can— different level of efforts, maybe you vary your bonus at the end of the year, but you can't say, oh, I'm going to take on an extra project now, or ramp up my effort this month to earn more money. You're pretty much on a fixed salary. I know this varies if you're in sales or if there's big upside bonus potential. For the most part, going from full-time to freelance is going from, okay, here's exactly what I know I'll make, to, okay, everything is up to me. The trade-offs are completely different.

So working on my own, it's either work on more projects or have more non-work time. And in freelancing, you can choose to make less money, which is something you can't actually easily do when you have a full-time job. Sure, you can take unpaid leave, You can negotiate part-time work arrangements, but generally it's pretty hard within a full-time paradigm. And this is where I've encountered a lot of interesting feedback and opinions on what I've done. So after I finished that big project in the fall and I had worked on a couple other things in the fall, I basically decided I would create some space, say no to most projects unless it was something that was incredibly interesting. And work on different creative projects.

So from January to the beginning of March, I basically made no money from consulting projects. But I had made a good sum of money to at least support my life and had the opportunity to work on these creative projects. What were they? One, I redesigned a lot of my content. I had writing from all over the web and brought it under one umbrella, which is now Boundless. That's where I came up for the name of the podcast.

And I also decided just to create this as a holding space for a lot of my content and playground for different ideas. Two, I started the podcast. That was, the podcast is not, I didn't start out with the podcast and say, okay, I wanna make X amount of money. I'm gonna get advertisers. I'm going to get this many listeners. Now I've been actually, impressed by how many people have subscribed.

It's actually hard to figure out who's actually listening, but you can see it appears 100 to 200 people are downloading each episode. So maybe you are one of them. Thank you for listening. But the goal really was, as an experiment, two things. One, to basically learn a new medium, right? So everything's evolving, and I just figure it's interesting to experiment with audio, figure out how to do some audio editing.

How do you actually do a podcast? Maybe it could help other people do it down the road. And to figure out if I actually like it. So I had a hunch that I would like it. I love having kind of deep, meaningful conversations with people. And I've been surprised with the upsides of doing the podcast.

A lot of my interviews, I'm going deep with them, getting to really know them, tell their story. I'm excited about it. And a lot of these have turned into good friends and starting to build a network around more people that are designing their their lives in different ways. And it's good to have that community, that connection. So it's been a huge upside. Like I said, I had a hunch that I would like these conversations.

I basically set the mindset of, okay, if I want to quit after 6 episodes, what will I have learned? I stole that from Tim Ferriss. That's how he started his podcast. But I took the same mindset. After a few, I kind of knew, okay, I want to keep getting better at this. This is really fun to try and interview people.

I think I'm still growing and improving. There's so much opportunity. I listen to all my episodes and it's like, "Oh my God, I can do a lot better here." But it's still a challenge. It's fun. I'm still doing it. And it's been great to hear people's feedback.

You generally hear more of the positive feedback. People don't go out of their way to say, "Hey, this sucked." Sometimes I wish I'd get more of that feedback. I do have some friends that are super honest with me. You guys know who you are. Keep it coming. I need that reinforcement.

I don't have a team I work with that's giving me the feedback to grow. So I always look forward to that. And then the second thing I worked on was I created a future of work mindset assessment tool. So in the first 6 months of working on my own, I realized that a lot of what had prepared me to make such a smooth leap was that I had been shifting my mind around the future of work. I had been reading and thinking a lot about this and doing a lot of experiments on the side. There's an article I'll link up in the show notes called "My Awakening" and basically details how I started this journey about 3 or 4 years ago and basically building the mindsets, the behaviors, the practices, and wanted to create a tool just to assess like, what are people's mindsets out there?

What are the differences between full-time employees, people in alternative work arrangements? I'll be publishing some pretty cool results from that survey. Soon. But again, with that, that was an experiment. I wasn't designing that to turn it into something that could be sold or make money off of. I've actually had some interesting conversations with a couple clients, or I would say potential clients, who were thinking about using it as a test in their company just to figure out how do we cultivate these future of work mindsets in our company.

So that's been a really cool experiment. And then I had planned a trip to Asia in April, and that was a 1-month trip and part 2 of an experiment of just extended travel. Would I like it? I've been thinking a lot about could I be a full-time digital nomad? Wanted to just test, do I like longer travel? I did a trip to Europe for 1 month last year and really liked it, but it was at the beginning of my journey, and I think I really had some kind of unwinding to do.

From my full-time work experience. So this was another experiment just to see, okay, would I like traveling to Asia? Would I like doing it for a long time? Before I left, I had a client opportunity emerge, and because I'm working as a self-employed freelancer, I was able to basically dictate my terms and say, I will do this if we can do it this way, otherwise I'm not interested. It was a project where I would help build a consulting skills training program, something I've written a lot about. I worked on the faculty at BCG when I was at Boston Consulting Group and was pretty excited by, made a pretty compelling pitch, but boldly went to the client and said, okay, I will do this project if you let me work from Asia 25% of the time.

Remotely and for this rate. And the crazy thing was they said yes, right? So they're not hiring me to show up and be part of a team, right? They're hiring me to solve a problem, create things for them. Didn't really matter where I was to do that. So that was a successful experiment that's turned into a bigger project over the summer that's really sustaining me.

So what else have I learned? I think other observations from being a freelancer and self-employed are just people's varied reactions to my life. So I'm going at it a bit differently than most. I'm basically combining a lot of different things, experimenting with travel, experimenting with longer periods of non-work, more creative activities interspersed with work, ideally always doing it remotely. And there are a couple of reactions. I think one I get a lot is, "Wow, you're so brave.

I could never do what you do." I am not sure I totally agree with that. I think a lot of people underestimate what they're capable of. My strategy has really worked because one of the key things I did was lower my cost of living. So I often challenge people and say, "Okay, it's actually pretty simple to start. It's basically spend dramatically less. I commit to a certain amount of time of freelancing." and use your savings to sustain you.

And then creating that opportunity, that space, that time, you'll often find that you start putting pressure on yourself to go after opportunities, pursue different things. And I think people often underestimate themselves. We look for employers to give us jobs. We look for managers to tell us what to do. But that's not really the reality. Anyone that's excelled at anything has gone above and beyond on their own personal motivation.

So that's the first reaction. I think the second reaction is more along the lines of, "Okay, this is interesting. This is cute what you're doing, but when are you going to get serious? When are you going to get a full-time job?" I often fight off the urge to kind of get defensive and have them make it feel like they're judging me, right? Obviously, they're looking out for my best interests, and I think this comes from just the mindset that is so deeply embedded. I actually wrote another article about this called "Questioning Work: Why Our Modern Conception of Work Leads to Some Deep Unintended Consequences." And I think it's important to question, how do we think about work, right?

And moving from a full-time paradigm to a freelancer self-employed paradigm has really forced me to question a lot of these beliefs. Our labor economy is not that old of people working in full-time jobs. It's basically 200+ years old and has involved people going to offices or factories, showing up, doing the work, and being taken care of. And I think especially in the last 30 years that there's been a disconnect. The share of wages going to labor is going lower, the share of wages going to corporations is higher, and people are feeling this disconnect. I mean, there's huge anxiety, people losing jobs, but We're still attached to this idea that having a job is the goal, right?

And what does that mean? That means showing up and going somewhere 5 days a week. And we're shifting to an era in which that is no longer the case. But a lot of our policies, our political dialogue, and just our cultural understanding are still aligned with that thinking. So it's been interesting to be on the other side of that. I'm seeing that I'm still able to sustain myself, meet my needs, and perhaps I'm not always pursuing more, more, more, more money or more status.

And my goals have really shifted to kind of thinking, "Oh, you need to progress. You need to have a career. You need to show constant growth," to, "How do I build a good life? How do I spend time I'm proud of? How do I do creative? How do I create value for other people?" It's a big mindset shift.

It's something I'm still figuring out what is the right path down the road, but for me, those things are are so exciting and so motivating and so energizing. So I'm not thinking about, "When are you going to get serious?" If anything, I've gotten more serious about how I spend my time, the things I value, and where I focus my energy than when I was a full-time employee. I think when I was employed, it was easy just to not challenge yourself or not question things. If you just keep showing up, you'll keep getting that paycheck and everything's all right. Nobody ever gives you crap for being employed and showing up and going to work every day, right? You get praised.

You could be miserable and not energized and maybe you're becoming unhealthy, but people are not going to say, "Hey, you're not doing a good thing by working and going to a job every day." So it's definitely pushed back on both views there. It's been interesting just to kind of be experimenting on my own life, hear people's reactions, talk to other people pursuing these paths. Often, the third reaction is the freelancers and other self-employed people I talk to which you talk to people like Steve Worley or Cody Royal, Amma Marfo on the podcast and they can't even imagine a different life. Of course, you would be a freelancer. Of course, you're self-employed. There's so much upside.

I mean, so much energy, so much freedom, so much autonomy. And that's pretty cool to hear from those. But I always try to take people's different perspectives. I don't want to get in a new bubble of being ignorant of what other people are experiencing. But it's been fun. It's been a journey.

So I'll leave it there for now. If you enjoy these smaller bite-sized little updates as opposed to my lengthy long-form writing, And let me know. Appreciate the feedback as always, and have a fantastic week.