“You inspired me to quit my job!”

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Fairly frequently, I get emails similar to this:

“I’ve been following your work for years and you’ve inspired me to quit my job and try to build an online product/freelance!”

The problem is that I’d never want to inspire such an endeavor. Ever. Well, maybe, but with some huge caveats.

First, I don’t think there’s anything wrong with working for a company or for someone else. That’s not a route I ended up taking, but I don’t think there’s one right career path for everyone, otherwise all our LinkedIn profiles would look identical (or at the very least, we’d all have LinkedIn profiles).

Second, those “real jobs” that a lot of folks dismiss to chase green grass come with some pretty handy things, like healthcare, paid vacation, oh, and not having to manage every aspect of the business. I don’t personally think full-time jobs are more or less “stable” than working for yourself, but they definitely come with perks.

Third, if you want to quit your stable job and make a go of it online or making products or doing anything your heart desires, please do. While I wouldn’t ever want to encourage anyone to do that, I’d never want to tell anyone not to. It’s your life, of which you are in control. I’m just a random dude on the internet who shares ideas and notices things. The reason I’m writing this piece is because if you’re interested in pursuing work on your own or for yourself, you should know more than “it’s possible to make 6-figures while you sleep on a beach in Bali beside your laptop.” That is possible, sure, but there’s much more to it. Also, laptops and sand do not mix.

There seems to be an epidemic of online entrepreneurs who get successful through a series of fortunate events (myself included) and then look back and rationalize their achievements as smart and strategic planning on their part.

“Look at me, I made a million dollars selling my online course that teaches your cat to knit cozies for your TV remote! Since I knew what I was doing all along and knew it was a million dollar idea before I even started, I can teach you to do the same! My Lamborghini is fun to drive in the Hollywood Hills, but I’m more proud of my KNOWLEDGE of cat knitted remote cozies.”

Except it doesn’t work like that.

We buy into our own hype when things go well and then tell others about it. At different times, I’ve completely had my head up my own ass about achievements—assuming a lot of luck was the result of careful planning or perceived smarts on my part. What I’ve realized about success, both in the tiny amount I’ve seen in my own work, and in the desire I’ve felt looking at others with far more, is that it’s seen only in one-dimension. We see one thing, like someone working for themselves, and assume all the factors that led them to where they’re at are the same as ours.

For example, I could say: “I dropped out of school, then quit an agency job, and now work for myself making mad cash! All my big risks paid off and yours can too!” When really, the only reason I quit university is because someone offered me a great job in my 2nd year. It felt like less of a risk to take a job than finish a degree and hope to get the same job in 3 years. When I started working for myself, it was completely low risk for me to quit my job as well. I had only worked at an agency for about 14 months, they had no benefits to speak of (it was a different time back then), and I was still living in my parents basement. My parents weren’t well-off by any means, but were squarely middle-class and able to afford to keep a roof over my head and my stomach full, even if I had zero income. Going out on my own was an easy choice because I really had nothing to lose—no mortgage, no kids/dependents, and relatively good health. Worst case scenario, my own business could have flopped completely and nothing else in my life would have changed—I could still walk up the flight of basement stairs and get a home-cooked meal.

I also lucked out by making websites before most other designers. So I had a huge advantage of being “first to market”. While my skill/expertise/whatever played a part, so did luck. I can’t take 100% credit for knowing what the hell I was doing. I made and continue to make so many choices where I don’t know the outcome. Same with making online products: I was only able to do that, and to experiment with them because I had a well-paying job as a freelance web designer.

I had also squirrelled away so much of my earnings in the 15 years prior and lived well below my means to make sure I had zero to no debt (the only debt I ever carry is my mortgage, and I only carry that because it’s a ridiculous 2.26% interest rate—and I bought a place that was half what the bank pre-approved me for). But saving money and being really cheap isn’t as motivational as telling someone to take big risks, because they’ll pay off. Even in saving money, I’d rather not bet on big risks that could pay off, I’d rather put it into index funds that have lower but more consistent returns.

I then rode yet another trend of online products which again, had little to do with skill and a lottle (I just made that word up, but it should exist as a word) to do with trends and help from the clients I had worked with earlier in my career. I just happened to start making courses before a lot of markets were saturated with them, so I was able to get enough students in each to make them more valuable (based on their feedback) and more compelling to buy (with testimonials and success stories). Don’t get me wrong, I love my courses and believe in them, but I’m sure there are other courses out there that are just as good, which don’t have as many paying students.

I’ve definitely worked hard to get to where I’m at and leaned heavily on skills I continue to build, but I’ve also been incredibly lucky that a lot of small bets have payed off. Bets I wouldn’t have made if the stakes were higher or if they were work out or bust. Not to mention, my hard work as a white dude from a middle-class home in a first world country with decent social systems takes me a lot further than others who have different life circumstances who put forth an equal amount of hard work and skill.

Advice is warped by time, hindsight and our own life experiences—which isn’t very scientific. So it’s tough when I hear from folks who see one aspect of my or someone else’s life, the public part—the business success bits—and assume they should make life-changing decisions based on semi-motivational essays or quotes over mountain photos on social media. This isn’t to sound pessimistic or that I believe I can do something someone else can’t—I just want to make sure decisions others make are based in reality and with a bigger, clearer picture in mind. Outside of hype or dreams of grandeur. I don’t want to inspire bad choices or huge risks. I’d rather inspire critical thinking, challenging what I say, and assuming the filter of your own life may cast a completely different light on what you decide you want to do with your own.

This piece was totally inspired by AJ’s tweet storm on the same subject.

Posted in Life lessons