Your work has one. Your boss has one. Here’s why you MUST have one.

You know the story: clumsy Alice tumbling down the rabbit hole. You probably don’t remember it contains one invaluable lessons on life and career.

I grew up with the dodgy TV version where Whoopi Goldberg plays the Cheshire Cat. Where some turn to religion or philosophy for answers, I look to Ms. Goldberg in equal measure. With more sass than Lewis Carroll’s text requires, her conversation with Alice goes like this as Alice asks:

“Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to get to.”

“I don’t much care where –”

“Then it doesn’t matter which way you go.” 

There is great appeal to Alice’s spirit of wonder and wander. Her journey through the dreamscape ranges from idle bliss to nightmarish intensity. It’s fun and outrageous. It’s never boring. It ends safely. It shouldn’t be copied.

I’ve always avoided deep questions about where I’m going in life and career. The gravity of the task is overwhelming. The thought of a personal strategy feels restricting. Clumsy words fall onto a page and are almost immediately erased in frustration. I reassure myself that you can’t plan life. It’s okay to tumble through wonderland.

But no matter the challenge, we must have a plan. Alice is no example. Here’s why:

1- You care deeply about where you’re going.

Imagine wandering through the international terminal. A young man in a smart suit offers you a chance to win a free mystery flight to somewhere exotic and extraordinary. Why not? You spin a novelty-sized wheel, bright lights flash, onlookers cheer, and a beautiful woman hands you a return ticket marked “anywhere but here”. The competition man smiles and wishes you a pleasant flight to “wherever.” After a long night’s journey, you touch down at Al-Tabqa Airbase where a driver meets you with a smile and a sign saying “Welcome to Raqqa! Enjoy Sunny Syria!”

Life doesn’t come with a travel agent. If you don’t know or care where you’re going, you could end up anywhere. You might have heard the expression “failing to plan is planning to fail.” False. Failing to plan is planning for a random result. It’s like throwing darts blindfolded. You might fail miserably, succeed spectacularly or anything in between. It’s a mystery flight to “I don’t much care where”, which is fine as long you’re as happy with Raqqa as you are with Bora Bora.

2 – Plan big, then stay flexible

To be sure, you can’t (and shouldn’t) plan everything. The best illustration of the principle is the Route 66 example. Say you’re driving from Chicago to Santa Monica. You plan. You think: car, gas, map, phone, music… what you need most and a few things that spring to mind. You get in the car. You go.

You don’t know how much time you’ll spend in Amarillo or what you’re having for lunch in Albuquerque. Lookouts and landmarks pause your journey temporarily. But at every truck stop, every bar and every burger place, you tell people the same thing: “I’m on my way to Santa Monica.”

3 – Be part of your plan, or someone else’s.

They say that those who don’t set goals work for those who do. It’s not nefarious or conspiratorial, it’s business. Thousands of people are paid to think about how you can become part of their plan, especially if you don’t have one of your own.

Imagine (obscenely) that Alice’s journey took her through King’s Cross in Sydney. A former entertainment district, all Sydneysiders know the giant Coca-Cola billboard erected over 40 years ago. Upon viewing the sign, she agrees that a refreshing, ice cold Coke is exactly what she needs. Her journey now includes caffeine, sugar, and forking over $3 for little or no nutrients.


The same is true of work. While you’re on autopilot, in the boardroom, there is an agenda with the line item “staff.” This discussion will include promotions, raises, demotions, dismissals, and redundancies. It involves smart, experienced people. Good people who respect their employees, but plan for the business. How many times have you personally sat down with an agenda with “work” written on it? When is the last time you asked yourself What’s working? What’s not? What strategy do I have at work? Why am I working here? Or are we just a sub-set of our boss’s plan with our role delivered in an envelope after the board meeting?

There are no answers here – just questions that follow from an important and indisputable fact: We all need our own plan. So much of life’s extraordinariness is inaccessible without one. Some things just take grit, determination, trial, error, and practice. Planners lock away wonders from wanderers. As Keith Ferrazzi says, nobody becomes an astronaut by accident.

So over the next few weeks, I’ll be finding and listening to people with plans, goals, missions, visions in life and career to see what they know. Be back soon with the secrets.

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