Lesson 15: Whatever It Is, You Should Start Trying, Now

A few weeks ago, I had a really great chat with my boss. I don’t want to incriminate anyone by writing this story, but luckily for me I have three different people at work that I would call “my boss” because our structure is a bit free-flow. I also don’t think anyone at my work even knows about the magazine, much less reads it, but just in case, everyone keep your fingers crossed for me that this one goes unnoticed.

I should preface this story: I quit my job.

But let’s rewind a little.

With said boss, I was talking about career progression. I already had an idea that I was going to quit going into this conversation, but it’s always good to keep your options open. (Maybe that needs to be lesson number 15…). Anyway. My boss asked me where I see my career going. The classic question: “Where do you see yourself in five or ten years time?”

I thought about it for a moment, and I considered lying. I thought about giving the usual spiel of what any boss would want to hear, but I realised that: 1) I am a big fan of honesty. So why start lying now? 2) Telling them what they wanted to hear probably wasn’t going to get me anywhere anyway.

So, I decided to be honest.

“Actually, I want to be a writer.” I said. “I probably see myself doing this job for another five or ten years, but there’s no end goal in marketing.”

And, back to being honest: five or ten years was a huge exaggeration.

My boss looked pretty surprised; maybe at the answer, or maybe with my candour, I’m not sure. They gave it some thought before responding, and their answer really surprised me…

The Design Challenge

My boss told me about the Design Challenge. I’d never heard it before, but I came out of that meeting and did some research, and now I’m kind of obsessed.

The Design Challenge was created by Peter Skillman in the early 2000s; in fact, he even gave a short talk on this at a Ted Talk event in 2006 (yes, you guessed it, I’m almost 20 years behind the times).

The fundamentals of the experiment were these:

He gave some spaghetti, masking tape, string and a marshmallow to different groups of 4 people. Each group had 20 minutes to create as tall a tower as possible with the marshmallow at the top. Over several months, he studied over 2000 people in how they approached the task and their final outcome.

He found that, over and over, one group was more successful than the rest. Kindergartners.

In Skillman’s own words: “The Kindergarteners don’t spend 15 minutes deciding who is going to be CEO of Spaghetti Corporation. They immediately start building and learning.

And (more embarrassingly to someone who is a business graduate): “Many of the business school teams in aggregate had zero or near zero scores because they spent way too much time planning rather than diving in and learning by doing.

My boss very eloquently described this experiment to me, and then continued. “You’re in your 20s, right?” they asked, and I nodded. “Why are you not already trying to be a writer? You should be trying and failing as much as you can right now. When you’re older, your life is full of responsibilities, and you don’t have the capacity to risk failing anymore.”

Saying that my boss basically convinced me to quit my job to try and become a writer sounds like something you’d make up for likes on LinkedIn, but I promise you that this is completely true. 

My boss is like this. A bit different. They don’t want to keep you on the team because you have good skills or you know the business inside-out. They want people on their team that are passionate and focussed, and I think they were beginning to sense that my heart wasn’t in it. There are many more lessons I’ll take away from working with this person, but I might need to give it a little more time before I start chatting away about them online…

What Else Does The Design Challenge Tell Us?

This piece that Peter Skillman wrote on the Design Challenge is short, but I’d recommend giving it a read.

It extrapolates a lot of life lessons from an experiment that is based on marshmallows (that is to say, take everything with a pinch of salt), but it does get you thinking.

How many areas of life can we apply this advice to? I’ve had a “plan” for my writing career for a long time, but how much have I executed? Very little, is the answer.

“You learn by doing, discovering problems you can’t predict in advance.”

For example: If I’ve got a plan to become a writer that relies on my ability to enter competitions in the UK, I could spend three years writing as many stories as I could muster, only to find out I can’t apply because I’m not a UK resident anymore. 

Luckily this is a made up example, but unpredictable hurdles can arise in any situation. Why not start by submitting the stories I’ve already written, and work out the kinks that way?

“Team success is about leaving your ego at the door.”

This is something I’ve slowly been learning over the years (my ego is not one that is easy to leave at any kind of door), but it’s one I’ll be taking with me in my career as a writer and at the magazine. 

This experiment is also featured in a book, The Culture Code: The Secrets of Highly Successful Groups. The premise of the book is this: What do Pixar, Google and the San Antonio Spurs basketball team have in common? They all owe their extraordinary success to their team-building skills. (This deviates a little from the topic, but thought it was worth a mention.)

The point is this: you learn by doing, and if you’re not doing anything, you’re not learning. If you’re standing still, you’re not progressing. And why not start? You can plan all you want, but nothing is going to happen until you try.

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