When To Leap


Today I wanted to take some time to answer a question from Valerie, a friend to the channel. Originally this was going to be a short and sweet post, but in truth I'm writing this during my last day of work at the office, so it quickly turned into a pretty long post. I swear that by the time I'm posting from home they won't be as long. 

Valerie asks:

"If you ever feel like putting something out there about how you decided when the right time was to go full time, I'm very much interested in hearing that."

That is a great question, especially because I kind of glossed over that part during the first five posts. I guess I glossed over it because the general idea is one that is considered very scary, and so people are often told they're brave or admirable for doing it. While I believe that is true, I don't believe that applies to me. I don't feel really deserving of the title of "one of the people who risked it all to chase their passion".

Admittedly, I'm making this move in life from a position of privilege. For the four years before this weekend I had a pretty great job in a somewhat lucrative corner of an already lucrative industry, and I was lucky enough to work for a company that treated me well and (apparently) liked me.

This privilege afforded me two important factors that allowed me to make the decision to give YouTube a shot in 2018:

  1. It allowed me to save money.
  2. It set up a fairly easy and reliable Plan B

Truth be told, going right into this month, the channel isn't doing well enough to cover the cost of living completely. At best it's paying my rent and it's putting food in my mouth every month, which is definitely a big chunk of costs. However all of the other various expenses, such as monthly bills, are being paid for by the savings I started to accrue back in July when I decided to do this. 

I had run the numbers about a million times since that decision over the summer, and as it stands, if the channel doesn't grow any further from today onward, I can afford to do YouTube full time for about two years. The goal of course is that in that time I'll be able to grow the channel to the point where it's fully supporting me and I could go on to year three and beyond.

On the flip side of that, if the channel were suddenly deleted tomorrow, the Patreon ended, and everyone stopped visiting my books page, I'd still have enough savings to take about six to nine months off from work to figure out my life and act on it. I obviously hope that doesn't happen, but having that safety net made jumping a lot easier.

Then there's Plan B. Up until now I always described my job as "the boring tech side of advertising" because the actual title is usually unknown outside of the industry. I was an Ad Ops Manager. It's not a very fun job. Ad Ops itself is the department that makes sure that when Pampers buys 1.5 million impressions on our website, they get all 1.5 million impressions. Ad Ops is also the first line of troubleshooting when that ad we're supposed to display 1.5 million times suddenly stops working.

I was trafficking campaigns for the company for three years. In my final year I was promoted to manager which meant I waited for fires to put out. My God, how true all the cliches about middle management are. 

In any case, the fact that most people have never heard of Ad Ops is why my Plan B is my Plan B. Nobody knows about it. Nobody goes to school and majors in Ad Ops. Due to this simple truth, there is almost always a demand for experienced Ad Ops people and the pay is usually decent. Even four years ago when the job market wasn't as good, and I was a rookie with less than a year of experience, I was still getting job offers on a monthly basis at other publishers. 

To that end it's why I suggest Ad Ops to anyone looking for a decent holdover job. It's not glamorous, it's not fun, and it's mostly located in NYC and LA since it's advertising-based, but it's steady, in demand, and pays well. 

So as a result of all this, I knew going into it that if YouTube fell flat I would be able to get up and retreat back into the world of Ad Ops until I figured out my next move. 

As a more practical answer, I finally felt OK to make the jump when I worked out my finances and realized I would have, at the least, three or four months worth of money to look for another job (if I needed it). That number might vary depending on the field you're in or going to, but I do think whatever that number ends up being, it's the number to look for. It's definitely the main factor in why I waited until now to quit rather than doing it back in July or August when the channel was really riding that viral wave. I needed to save that money.

I realize that may not be the best answer, as it's not going to apply to everyone, but for better or for worse it's the one I ended up coming to. I know this will sound incredibly cheesy, but I've been very inspired lately by Walt Disney. Specifically I've been inspired by his words on failure:

I think it’s important to have a good hard failure when you’re young. I learned a lot out of that. Because it makes you kind of aware of what can happen to you. Because of it I’ve never had any fear in my whole life when we’ve been near collapse and all of that. I’ve never been afraid. I’ve never had the feeling I couldn’t walk out and get a job doing something.
— Walt Disney

How often in life do we fear something more than it's worth being afraid over? That doesn't mean we shouldn't be smart about how we approach it, whatever "it" is, and it doesn't mean it'll always be fun, but it also means we shouldn't let that fear stop us.

I've had jobs that weren't fun before, and I got by. I've had jobs that paid far too little, and I got by. I've had periods of my life where I didn't know what I wanted to do with it, and I got by. If I fail at Rob Plays this year and those three truths are the outcome as a result, I'll probably be pretty broken up about it, but I'll get by.

That's when I knew it was worth jumping.