#Advisorhack: Get In Over Your Head


Sink Or Swim… It’s The Fastest Way To Learn.

The idiom “in over your head” has a very literal translation, that of being in over your head in water. And what happens when you’re in over your head? Ultimately, you sink or swim. But really, it’s not so black and white. What about that fleeting moment of trial and error where you go under, swallow a little water, and flail about before you figure out how to tread? That’s why “sink or swim” is kind of BS, because it equates to “live or die,” which. most of the time, isn’t really the case. I’ve found that in real life–and in business–there’s often a small margin for error before things truly become dire, and it’s that moment of trial and error where you learn super-mega fast, because after that it’s “make or break.”

Lessons From Playing Paintball With Pros

I learned my lesson in going “in over your head,” of truly challenging yourself, while playing paintball last weekend. I rarely play paintball, and on this occasion, we were playing with professionals–four of them–each fully decked-out in camouflage with an array of specialized guns and equipment. These guys had played in tournaments against teams from West Point where there was live fire from M-16’s going on around them, flash bangs being thrown, and generals screaming into their earpieces–serious shit. And there we were, a bunch of rookies who’ve maybe held a (paintball) gun only a few times, going against ’em. How’d we fair? OK. We won some, we lost others. But, for me, the crucial moment happened in between the first and second games.

Game 1 was what they call speedball, which is the most intense game we played: Close quarters combat with lots of places to find cover, but, on the other hand, lots of players and paint flying everywhere, all the time. When the whistle blew I took off and found cover behind a bundle of barrels, and I didn’t leave that position for the entire game. I basically chickened out, peering around the corner, letting off a few shots, and ducking back when the fire was returned. I was never hit. My gun malfunctioned towards the end of the game, and I had to surrender. My team lost.

What I learned after that first game was that it didn’t feel like I was playing when I wasn’t taking risks. I needed to get in over my head (or “out in the open” in this analogy), and see if I could hang with the pros. So what if I got a little bruised up and my team lost? It would be better than sitting in the rest area after that first game, with no bruises to show for my loss like the rest of my team. Needless to say, I was more aggressive the next game. I got hit once (it was double-elimination), advanced upfield quickly, and helped my team win the second game. What I learned was that the faster you can throw yourself in a situation that’s completely over your head, where you have no choice but to sink or swim, you learn mighty quick.


If you want to learn fast, immerse yourself. We know it’s the easiest way to pick up a foreign language, but what about picking up something different, like an iPhone when you’ve been a Blackberry person? Here’s an idea: grab your new iPhone, and take off. Leave the Blackberry at home. Sure you might miss a few calls, a couple emails, but you’ll figure it out soon enough because you have to. There’s no other choice. Especially if those emails are from a client demanding information: the motivation for you to figure out that stupid touchscreen is a client’s business, which is your livelihood.

Or what if you want to write a blog post that people actually read? How about one that goes viral? Start writing every day. Immerse yourself in writing. Without a doubt you will write some terrible posts. You will also write some alright posts. But eventually, after many posts, you’ll nail it. You’ll write a post that tugs on all of the insecurities, anxieties, and questions that financial advisors have, and our little community will read it and share it and you’ll have succeeded.

Congratulations, you’ve learned to swim.

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DJ is a freelance writer, hopeful photographer, and social media has-been. He writes to financial advisors about lifehacks, science, technology, business and marketing for Blueleaf, a software that helps create dramatically simpler, more scalable financial advisory businesses. You can find DJ across the web (about.me/djswitz) or you can just follow him on Twitter (@djswitz)!
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