Going cold turkey as a solopreneur
A bold move that worked
You can find David on LinkedIn, Twitter or check out his website if you are interested in his services.
Let’s get started!
Bullshit in the creator economy
Kenny: As a solopreneur, you have limited time. Assuming you want to maximize freedom and the amount of income you get based on time spent, you’ll try to find ways to accomplish just that. The problem is there is information of various quality on how to achieve just that. Lots of high-quality information and lots of bullshit. I know you write a lot about bullshit. So, how do you determine what’s bullshit or not?
David: Essentially, bullshit is almost worse than lying because bullshit is putting content out there with no intention of it being true, false or otherwise. It’s just pumping it out. We're all sometimes prone to doing it, and I've seen quite a bit of that in the digital space, in the creator economy.
I really appreciate some folks who have become successful now and reflect on their early successes. For example, Amy Porterfield is highly successful. She put out her book “Two Weeks Notice” recently, and she talks about her first online courses being essentially bullshit. Because she was trying to create a course about something she'd never done before: making content in the creator economy. So there's that kind of bullshit that's out there, and it becomes this balancing act. Is this person actually speaking from their own experience? Is this their area of expertise or experience? Are they making this up as they go along because they've ChatGPTed it or seen big-time creators creating it? That's that whole balancing act.
How to prioritize your efforts as a solopreneur
Kenny: Okay, so, even with the amount of high-quality information, you still get so many different strategies and principles you can use to maximize your income and freedom. Sometimes, those are contradictory, but they all work. Some will tell you to niche down, others to be a generalist. I know people finding success doing either of those. You’ve done a bit of thinking on that. From what’s legit, how do you know what to execute to make sure you're maximizing the outcomes you really want and you’re not wasting your time?
David: You're bang on, Kenny, that there are so many ways to go about this. The creator economy is huge. It's only getting bigger. There are suggestions of a 30% growth a year.
Some people are going to have great success, like Ryan Holiday, just talking about stoic philosophy. Some people are going to be Excel experts, and others are going to be Notion experts. There's going to continue to be these people doing well that are very narrow and niche. They love it, they're passionate about it.
I'm going to guess they're probably going to pivot after a few years. On the other side of the coin, I’ll catch stories of people who say, “I’m out” or “I disappeared for eight months, and I've come back because I burnt myself out. I niched down, and I started to write about this stuff, and I realized I didn't know what was bullshit and what wasn't. And I just got bored, essentially, and fizzled.”
That has been something we've talked a lot about in our households because I jumped and left employment in a way that most people suggest you shouldn't. I just said, “That's it.” Not that we didn't have conversations. It wasn't like one day I was in, and the other day I was out. It was a very purposeful process. And we didn't really have a safety net. We've got three kids in a double-blended family. It's complicated.
As our kids have been getting older - they're all teens now, we always made a commitment in our household to have only one person working full time and the other person not as much. When I decided to jump, that put my wife in that position, and in the past, I've been the one not working full time, and she has. Then we shifted. We're not trying to maximize our profits or our incomes. We talk a lot about enough, “How much is enough?” and about building businesses that support our lifestyles. Not building lifestyles around income generating, whether that's employment, business, or otherwise.
That philosophy has been key in what we're talking about doing and getting into writing and the creator economy. I would say I probably “work” more than I did when I was a busy bureaucratic administrator and senior leader of a team with a multimillion-dollar budget. But my level of satisfaction, enjoyment, and passion is different. That has all been part of the whole package. Yeah, we're spending a lot of time at this, but loving it and being very slow and mindful, not running into it. Let's keep going slowly and steadily.
I've turned 50 this year. My wife's in her 40s. We're in a different position than, say, someone in their 20s saying, “Fuck this, I'm out.” In my situation, if you do that, you’ll think, “Okay, well, what am I going to rely on?” That's where I think many different approaches come from. Some of the creators, like Nicholas Cole and Dicky Bush, with their Ship 30 for 30 course, they're 20-something. There's a different approach going on. Whereas someone like Daniel Vassallo with his Small Bets philosophy, he's had a career, is older, and has a family.
Kenny: All very different approaches for different situations.
Focus on your internal compass
Kenny: Okay, so it sounds like you have a few principles that you discuss in your family, and those seem to be your guardrails in terms of experimentation. When you hear advice or you look at something that somebody else is trying that you’d like to experiment with, you look at it through that lens of freedom and going at it steadily and seeing some results. Is that right?
David: Yeah, that's really a bang-on observation. An example of that is when I took Nicholas Cole and Dicky Bush’s course. I did Ship 30 for 30 last January. I quite enjoyed it, and it really got me thinking. It took me about six months from following them to then taking the course. But I did it with a couple of principles in mind, which was, “How are they doing this?” Because my background is education and I was thoroughly impressed with how they do it. I don't agree with everything they put out. It's not like I disagree and I say it's unethical. It’s just not for me. And that's that lens, like you said, that we approach things with.
Many people reached out and asked, “I see your video review on there. What do you think about it?” And I'll put it in the context, which is I don't do probably 90% of what they recommend. It was the technical build of how they go about it which has really assisted what we're doing with my wife, the free educational emails. I totally agree with them; I think it is a huge area. But I don't use their cold DM 100 people a week, get on a call, send a loom. I don't hold anything against anyone that does that.
It's just not my approach. And that's where I find that some bullshit starts to creep in. And I liked your recent draft where you had the headline “I made $750k in a month.” Those typical headlines. And I have a medium article like that. Right through my career, I've made $500,000 off my writing, which isn't a stretch. It's put it in the context that I've relied on it. So I like how you've put that as putting the guardrails around it.
I'll often argue with myself. So how can I counterfactual think through my own processes, like where are the weaknesses? I'll often tell people if you ever want to build empathy for someone you don't agree with, break down their argument because empathy doesn't mean to agree. It means to try and empathize and put yourself in their shoes.
One of the best ways you can do that is to break down their argument and then realize, “Oh, shit, I've got my own biases.”
Going through that process of breaking those down, that's very much what we'll do in our house. We'll try stuff, see how it feels, see if we're interested in engaging. A couple of times, we've set ourselves deadlines on getting paid courses launched, but something doesn’t feel right. And then we would back that bus up. We would write some more, test some more, and now we're getting to a place where we feel more comfortable. It's an interesting battle we find between impostor syndrome, “Who are we to put these courses out?” and also instinctually, intuitively, something doesn't quite feel right about this yet.
You can always look at those things in hindsight and go, “Okay, I'm really glad I didn't rush out the door and blast that product out.” And yet I can also totally appreciate where people do that and then say, “I learned so much.” Dan Koe, for example, is a big creator. I really appreciate his honesty. He says he’s failed multiple times purposely, and he’s learned what he has to.
Kenny: It’s interesting how you really need to try a bunch of different things. I've been playing the drums and trying to play with different people, but I have no idea about the music scene here in Vancouver. After a stint with a military band and a Brazilian band, I realized I needed to experiment and go to different people, different bands, and different styles of music and learn what in each of those. Because if you start with one thing, I wouldn't say it's a waste, but then you only know that one thing. So you don't really know how it compares to other environments and other values. At least at the beginning, experimentation is very important to at least refine those values or even what feels right before committing to something.
The motivation source changes
Kenny: I want to shift gears a bit and talk about your motivation. You had a few tragic events that led you to take the leap and quit your job. That was your motivation when you quit. Is it still the motivation today? What motivates you now? Because it's been almost two years since you quit!
David: It's a mixed bag. We had a long series of deaths in our family, starting with my older sister in 2016. She had a very aggressive brain cancer. And then my wife lost all four of her grandparents over that time, all quite elderly. We were a little bit more prepared, knowing that was coming. Then, two grandparents on my side. And then, my mom was in her 70s and passed. My sister who passed, her ex-husband, he passed this spring. A friend of mine who was a very avid cyclist was just on his training bike at home and just dropped dead this time last year. Heart attack, very healthy. He'd had a heart murmur or some heart stuff that he was aware of, I learned from his family, but that was a shocker. He was at a national level.
All that was a big part of it. I was also in healthcare administration through COVID and leading a team. It was two years of flat-out emergency planning and response at the same time. Dealing with both of those every day, which was a fascinating exercise in cognitive dissonance.
Before I got married, I've been married for 15 years now. And before that, I worked in different industries. I was more or less a consultant and worked on my own. A solopreneur before that term was popular. And then, when I got married, I needed to be closer to home. My wife and I had been talking about it for several months, so I got out of care admin, and I was headhunted by a recruiting firm that's based there in Vancouver into a role back at a community college I'd worked at before. Slower pace, managing a team, interesting enough work, but I knew in about a month. “I don't think I can do this anymore.”
I've never been wired for an office or a cubicle, but I can do well in there. So it's that whole balancing act. Got paid very well. The deaths hit us hard. Lots of reflection and thinking. It's not to say we aren't aware that death happens. We talk about it all the time. My wife deals with that as well in her line of work as a counsellor.
But after it came in those big bunches, she told me, “You can get paid more for your time. You can always keep going and get paid more as an employee. But you can't buy more time. You've only got so much time. So what do you want to do with that?”
And it was a great line just for thinking. I thought, “Okay, she's fine with this. I'm ready for it. I'm out. I'll figure it out.” I had some confidence in my ability to be able to line up enough work to just constantly keep it going. And if not, I could go back. I've got enough skills and enough contacts that I could go back. That was my safety net, the trust that I could go back.
But going to the heart of your question, I was reading through a book about using intuition from Laura Day. She had a diagram exercise, and basically, it came down to this: I want to be able to write and to speak and to teach and to be able to make a living doing that in a way that supports the way I want to live. That's always sat in my mind over the years as a motivator. The other day, on a walk with my wife, because we've got the freedom to do so, she just said, “Well, look, there you are. There you are! You're doing it, man. You're right in the midst of it”
I don’t want to get into that “follow your passion and the rest will come.” You've probably seen my most recent newsletter, which is that following your passion can be bullshit. It's also a ton of hard work and steadily trying, thinking, failing, not getting wrapped up in your own head about those failures.
There's still a very similar motivation in all of those threads that hold that together. And ultimately in there is being able to use the time and the skills I have to support things I am passionate about.
The last big one is coaching our youngest in volleyball. He's taken a real passion for it at 14. In the past, when I was working and teaching part-time, I didn't have that time. Now it's three practices a week and lots of travel. All of those things come into this wonderful package of doing what I should be doing and what I want to be doing and a real trust that things will come into place. It's not going to be easy, and it's not like some magic bank account gets filled; they're going to be work put in.
Kenny: So, you started out with, “Okay, I need to do something. I don't really like where my life is headed, what I'm doing with my day.” You needed to draw a blank slate. Now it sounds like you're in a much better spot, and you've created something that you really like, and that allows you flexibility and still has a pretty good income. The idea is to do more of that, but at the same time, also protect what you build and make sure you maintain what you have.
David: Totally. The idea is to get ourselves to a place of having those passive income sources. You've got courses going, but not in a way that makes it about us and our income. That's that whole aspect of Humanity Academy, the company with my wife, where our tagline is there's no one right way to live. It's about trying to be part of humanity as well as working with humanity and balancing that out. As I look at the creator economy, I do see some really great stuff that folks are doing out there. Yeah, there is a shady side and an unethical side, no question.
Ideally, I'd like to be in a position where I could support nonprofits without having to say, “Hey, and here's my contract and my rate.” I'm able to do that but I'd like to be able to do more. But also, we’d love to get to a place where we can produce courses, write, speak and engage with folks and be part of their journey.
What inspired you in David’s story? Share a comment below.
Thanks for sharing all of these helpful thoughts, David and Kenny!
Thanks Kenny. Enjoyed our chat. 🙌