I think people naturally optimize their lives for stability. Stability equals comfort. If I know what tomorrow looks like, I know that I won't be bothered by tomorrow. I know what I'm supposed to do. I know what I need to earn. I know what the expectations are. I know how the system works.

The problem is that stability can also be boring. Challenges force us to learn. They force us to solve problems, encounter new ideas and develop new abilities. Remove enough of those challenges and your world can start becoming very small and very protected.

There is nothing inherently wrong with that. It’s a beautiful life. It’s simple. Except somewhere along the way you find yourself lying in bed thinking: How did I get here? This is not my beautiful life.

And then you go to work the next morning and keep doing exactly the same thing. Groovy. You’re killing it.

The sidewalk and the dirt path

Imagine a public square with a beautiful flower-lined sidewalk running around its perimeter. Except people don't always use the sidewalk. There's a dirt path worn diagonally through the grass because that's the route people actually need to take. A sign goes up, “keep off the grass”, and yet people keep crossing, so up goes a fence.

There is a version of this in your workplace. I don’t have to know it for a fact to know it’s true. There is a procedure. People aren't following the procedure, so another procedure gets created to enforce the first procedure. Nobody stops to ask the obvious question: Why aren't people following the original procedure?

The sidewalk isn't necessarily wrong. Plenty of people are perfectly happy using it. It gets them exactly where they want to go. But what about the person who can see the dirt path but keeps taking the sidewalk anyway? They know the existing route isn't taking them where they want to go. But this is the route. This is how things are done. They've invested a lot in getting here.

So they keep walking.

When the system becomes the objective

I've spent a lot of my life trying to make it in systems that didn't particularly work for me.

I went to a small private school before going to a large university. I did very well in high school. Looking back, I think part of the reason was that I was encouraged to try things and explore. I was encouraged to grow my mind rather than simply conform to a way of doing things.

University felt different. I studied history and urban geography, and I loved the material. I wasn't bored. I enjoyed the lectures and I still love both subjects today. But I became frustrated because I couldn't seem to do well within the system. Write your essay the right way. Format the bibliography the right way. Express everything the right way. The quality of my argument or the depth of my understanding sometimes seemed less important than whether I had expressed it in the prescribed form. Eventually, I couldn't find a place for myself in that world, so I left it entirely and spent the next 20 years bored in hospitality.

I never lost my love of history or geography. I still read it for fun… yes, it’s true, I do. But I didn’t belong in the academic system, and they never wanted me there. Only now am I really finding a use for it in a podcast about careers.

I was taught to be critical, whether intentionally or not. I was told that people who don’t learn history are bound to repeat it. So I don’t want to repeat history. But all that meant for me was to watch others drag me into negative patterns, only to be called a naysayer. I've probably learned as much from the bad lessons of my peers as I have from the good ones.

Adaptation is about agency

That's what adaptation means to me.

It isn't about constantly changing everything. It isn't rejecting comfort for the sake of discomfort. And it certainly isn't about blowing up a perfectly good life because somebody told you that you're supposed to be growing.

It's about agency. Agency, by the way, is a catchy term us coaches like to throw around because it sounds cool. Ultimately though, agency is about power. The power to make your own decisions. To chart your own path. To dictate your own vision. I'm fighting for my own vision. I'm trying to make that vision work for me. I'm pivoting the systems around me so they produce the outcome I'm after.

For a long time, I've wanted to be paid for my ideas rather than simply for my time. It’s a philosophy I clung to but couldn’t articulate.

That doesn't mean other people are required to value my ideas. It means I have to get better at communicating them. I have to learn how to make them useful. I have to experiment with different ways of putting them into the world. And when something doesn't work, I have to be willing to change my system.

Why do we reject the alternatives?

I don't think most of us suffer from a complete lack of possibilities. They suffer from an inability to see them as possible. Someone will tell you something they'd really like to do and then immediately explain why they can't do it because there are rules, restrictions, responsibilities. They say things like, “that's not what someone like me does” or “I need to be a team player.” Or the worst one of all: “They don’t deserve it, so why bother.” I hear this one way too often.

Throw that way of thinking together with the sunk costs of a comfortable modern life and the expectations of everyone around you, and it's not terribly surprising that people become reluctant to investigate alternatives.

Here’s the problem – you’re trying to think your way out of this

You are making decisions based on the information that brought you here in the first place. You know your job. You know your industry. You know your responsibilities. You know what you're good at. You know what you've been told is realistic. And you've probably spent years getting very good at explaining to yourself why things have to work this way.

So when some weird alternative appears, what do you evaluate it against? Everything you already know. Of course it loses.

That's the point of the dirt path. Somebody had to walk across the grass before anyone knew whether the diagonal route worked better.

Alright…

Society tells us that people walking across the grass makes an ugly path. Your legs tell you that it saves you two minutes of walking. Does that square exist to maintain order, or does it exist to make our lives better? Maybe you should tell the city they should pave that path.

What are you actually protecting?

This is where risk gets interesting. Because I’m not suggesting you gamble your house or walk out of your job tomorrow to open a beach bar in Mexico… though that is an awesome idea, so go do it.

I'm asking whether all the things you currently regard as untouchable are actually untouchable.

Take money. “I can't take a risk. I have kids. I need my salary.”

Fair enough. But what are you actually trying to protect?

Is it the salary itself? Or is it security for your family? A home? Opportunities for your children? Time with them? Your ability to be present rather than permanently exhausted by work? Those aren't the same thing.

Once you separate what matters from how you're currently providing it, you have something you can work with.

Maybe the salary really is non-negotiable. Fine. Then don't throw it away. Use it. Let the stable job finance the experiment. Let the predictable schedule give you somewhere to explore. Let the experience you've accumulated open doors somewhere else.

This takes some discipline. When you're unhappy at work, it's easy to let the bad parts of the job ruin the good ones. You disengage. You stop trying. You spend all your energy resenting the place you're in while overlooking what that place is still giving you.

If the job gives you money, use some of that money to build your future. If it gives you predictable hours, use the time outside them. If it gives you access to people, knowledge or experience, learn what you can while you're there.

The point isn't to risk everything you've built. It's to stop treating what you've built as something that can only be protected. Use it. Leverage it. Make it pay for what comes next.

Make the possibility real enough to investigate

Suppose there is another path…. Crazy idea, I know. But humour me.

• What would it look like?
• What outcome would it produce?
• What would it take to build it?
• Who would you need to know?
• What would you need to learn?
• What would have to change?
• What wouldn't have to change?

Write about it. Talk about it.

Learn how to use feedback

I've learned to make use of suggestions people have given me that I initially rejected out of frustration. Why don’t you people understand that I don’t want to be a teacher!

Simmer down John. Break it down a bit. “Wait, I don’t have to teach children in a public school.” No, you don’t John (and guess what, no one pointed this out...). “Maybe they are telling me that I have interesting ideas and an ability to tell stories that can help people live better lives.” They like the way I explain ideas – I like explaining ideas – I should ask them if that’s what they mean. “Oh really? You do!” Then I should do it more often. “Hot damn, I can do it my way.”

Alright, I have an idea I can experiment with. Explaining ideas means people will have to think with me. I must make my ideas interesting enough that other people will want to think with me. Key piece of all of this – I start with a title and I get teacher. Bad. I start with an idea and I have the experiment. Good!

That's when interesting things start happening. These abstract weird ideas lead to something real. Why? Because people make suggestions. They introduce you to somebody. They challenge an assumption. They tell you something won't work. They show you something you hadn't considered. You don't have to accept all of their advice. But you sure as hell can use it.

How do you know it's working?

Eventually, you start seeing results. Maybe networking suddenly becomes useful because you have something you want to talk to people about. Maybe people start becoming interested in your ideas. Maybe you find yourself seeking out opportunities without having to force yourself to do it. Maybe the things you know you need to do start feeling possible.

That's when things start getting good. You try something. Something happens. You learn. That gives you a reason to try something else. The more you act, the more information you generate.

The more information you have, the easier it becomes to see possibilities. And the more possibilities you can see, the less dependent you are on the sidewalk someone else built for you.

Start with the weird ideas

So don't start by changing your life. Start with the weird ideas that have been sitting in the back of your mind. Write them down. Especially the ones you normally dismiss immediately.