Planning Ahead and why You’re Screwed

Updated to Business, Productivity on January 23, 2023.

It’s that time of year again – the days are shorter, malls are full, power drills are on sale and your year is winding up.

How are you feeling?

Optimistic? Fearful? Regretful? Confused? Exhausted?

I’m feeling all those emotions and then some – I want to turn a fresh slate and start clean next year, but…

The reality is I’m one list away from repeating 80% of the mistakes, bad decisions and procrastinations I made this year.

In short: I’m screwed.

Sure, I can blame it on our wiring—we’re all predisposed to see what we want to see. If I think I’m a shitty planner, or prone to procrastinate, or perennially overwhelmed. Well, that’s what I’m going to see more of.

Psychologists (who have nothing better to do than name things) call it cognitive bias – I call it being screwed.

Confession: In January I wrote the goal: “Publish book about becoming a speaker”. Guess how much I got done.

Nada, squat, zero, zippo – nothing.

I could write a book on speaking over a weekend. It wouldn’t be great, but give me a month for research, interviews, writing, and polishing and I’d have a pretty presentable piece.

I didn’t even create an outline.

What about you? What did you plan on doing, but didn’t even start?

Well, dear reader, as we get ready to put a bow on this year I want to share 5 steps I’ll be taking to break my deja vu time trap and make next year my best yet.

Follow along if you really want change (or go back to playing Tetris).

We start with a review.


This week, I was in a bookstore marveling at shelves full of shrink-wrapped calendars and day planners. I thought of all those goals and plans that get carefully recorded (“I WILL lose 15lbs by March”) only to be replaced in a month or, worse yet, ignored altogether.

I’m not sure what’s the perfect solution, but I know it’s not about new journals and making lists.

It has to start with a review.

Not some analytical, pocket-protector, Excel spreadsheet with weighted-averages – just an honest look at priorities.

A great question to ask is: “Moving forward what do I need to stop, start, or change to get what I want?”

If you want to know more about completing a review for yourself or even teams, read this post.

We also need to celebrate.


I don’t celebrate enough. You?

Celebration is good for the soul, for your troops – it’s also an incentive.

When my brother Dan (I was a minor partner) sold Whitewater Adventures – one of the first whitewater rafting companies in Canada – we celebrated! Not only did we arrive in limos to the oh-so-austere Brock House, in Vancouver, Dan had commissioned silver belt buckles with the company logo for all staff.

That was a celebration.

Was the expense and effort absolutely necessary? Of course not. But that night was invaluable.

We’re all wired for rewards and even a little celebration pre-programs us to want more. It’s the reason why couch potatoes will lace up and train for a charity walk or why we save for a vacation or new car.

This week, take time to celebrate – it could be nothing more than a few minutes going through your calendar and recognizing your hard work and all the wins you created.

Next, forgive.


In most cases I’m my own worst enemy. Okay, in all cases I’m my own worst enemy. This applies to letting go.

I love to put a death-grip on misery and let it suck me down a toilet bowl of lost dreams. Even though I’m the only one in this pity party, I have a hard time shutting it down.

The hard truth is our mistakes are fodder for a better decision. “Good judgment comes from experience,” says American author Rita Mae Brown, “and experience comes from bad judgment.”

Without our screw-ups life would be one sad party.

So, what missteps, failures, or nonstarters are you hanging onto?

  • Business?
  • Relationships?
  • Health?
  • Fitness?
  • Time?
  • Money?

There are 2 types of forgiveness:

Forgiveness with resentment and blame. This is a disaster of raised cortisol levels, chronic stress, depression, weight gain and heart disease. Nasty.

And then there’s forgiveness with release: You choose to move on without baggage.

I need to let it go before I can get real.


Most people over estimate what they can get done in a year and underestimate what they can get done in a day. The trick is to get real.

When I sat down to write Give Me a Break I was nervous as hell.

I’d never written anything longer than 1,000 words and I wanted this to be my magnum opus. On paper I mapped out a huge project with support staff, promotions, an agent and off-the-chart sales.

The only problem was, I still had to write the damn book.

How many times have you made something so big you never get started? Like that house renovation, weight loss plan, business start-up or transforming a moribund relationship?

I do it all the time and it leads to, well, nothing.

So I got real, and just wrote the book. Once I got momentum on just that one goal, it only took 2 months to get a rough draft. It didn’t smell very good, but it was a start.

Only then did I start to seek out editors, get printing quotes and start to think about promotion. Two months more and it was in my hands, in stores and making sales.

Creating a big, detailed list could just be your excuse for not getting started.


In the story of Buridan’s Ass (French philosopher Jean Buridan, 1300-1358), a donkey finds himself halfway between a pile of hay and a bucket of water. The donkey looks left at the delicious hay, then looks right at the thirst-quenching water. Left, right, left, right, left, right.

But no movement.

Because the donkey can’t think about the future, it’s stuck in the present – torn between going for the hay or going for the water. So it does nothing and eventually keels over from thirst and starvation.

Don’t be a donkey.

You’re always better to do something, mess it up, learn and move forward than to be a donkey and do nothing. Irish novelist, James Joyce, put it more poetically: “Mistakes are the portals of discovery.”


You might be reading this and thinking it’s old hat—you’ve nailed the planning process. Or you might be thinking: “Holly crap it’s like he’s in my head!”

Either way, do me a favour.

Tell me in the comments what you’re doing about planning for next year. Are you boycotting lists altogether? Are you trying a new process? Maybe you’re doing nothing.