Escaping From Monkey Island

Becoming your greatest advocate.

A few months ago, I saw a kid dive into a coloring book armed with what looked like eighteen different uncapped markers, hell-bent on a mission bent fueled purely by chaos. I find myself jealous of this disregard for what everyone else thinks. Who cares if the adult wants the dinosaur to be purple: it’s going to be every color of the rainbow.

It’s unsurprising that many of us find ourselves coloring more within the lines after each passing year. Our early years are filled with an extraordinary number of firsts: our first job, our first shitty report-card, even the first time we file taxes on our own. We slowly assimilate as we’re rewarded for following directions. Follow the process at work and hopefully get promoted, drive the speed limit and you’ll avoid tickets, don’t make too much noise and people will generally like you.

There’s something to be said for coloring within the lines. If you play by the rules, you don’t shake things up too much. You’ll probably be fairly happy. You’ll probably progress in life at a steady clip and probably avoid fallout. A whole ‘lotta probably.

When I was younger, I owned this absolutely ridiculous game called Escape From Monkey Island. What made it particularly ridiculous is that there was no probably. The game save would crash about a quarter of the way through it just as I finally was about to start escaping from monkey island! Like clockwork, I would pick it back up again, retrace all of the familiar steps again, and see it crash again.

That same half of a game I played over and over – hell, all video games – are fixed containers. Whether or not you choose to take it, there is a defined path. We don’t get to refine final decisions or retrace our steps over and over through a summer like I would in Escape From Monkey Island.

You’re not in a fixed container. You’re not a shoddily coded group of pixels waiting for your next quest assignment. One of the most toxic mindsets that someone can develop is that things will just simply “work out” with time. That by virtue of waking up every day you are owed something from the world: happiness, a promotion, a house, your own business, etc.

Sounds like a one-way ticket to monkey island to me. Trying the same game over and over and getting the same results. Hoping things will just work out. As cliche as it sounds, the best of life occurs in the space outside of what’s defined. The best of life occurs in the margins. It also occurs when you learn to speak up for yourself.

In my career, and for quite some time, I thought it was the manager’s responsibility to ensure you’re getting promoted and paid more. And that the only avenue where I could bring up my compensation or job satisfaction was in another rushed annual review. Frankly speaking, managers are in place to ensure that the team continues to perform and to either protect (by retaining employees, keeping costs low, and implementing efficiencies for scale) or by growing revenue. This isn’t to say that they do not care, but instead, motivations are misaligned.

Armed with this information: you would think that more people would advocate for themselves in order to grow. But whoever you make an ask of, whether it is personally or professionally, will immediately begin to wonder: “How does this impact me?” In the context of asking for more compensation, your manager might immediately wonder: “How will this impact our bottom line? Can we afford this? Should we afford this?”

Here is a useful framework to apply to anything else you want in life: become your greatest advocate and be prepared to back it up. This requires you to stay disciplined and take your goals very seriously. In the context of asking for more money, you flip that same script from your manager on yourself: “How do I make sure this will impact their bottom line? How do I make them feel like they would be irrational to ask if they can afford this?” Make it easy to say yes.

Becoming your greatest advocate requires you to take an extreme amount of personal responsibility. You are no longer waiting on others to design your future: you are deciding what you want and bulldozing the path to get there. You are asking for what you deserve because you removed any possible reason why someone would want to say no. Again, they don’t really teach you that early on in life.

Learn from me: you don’t escape monkey island by picking up that same game every other weekend in the summer. You escape monkey island by deciding you’re not playing the same dumb broken game ever again.

I have a lot more that I’d love to say or add to this, but hopefully, this helps. In short, become your greatest advocate and get after it.