The SMARTASS Secret to Goalsetting & Productivity

Remember the beginning of January, all those seasons ago? Remember how jazzed you were about that new year new you thing? How determined you were to keep your handful of really good New Year’s resolutions?

You and millions just like you. Driven by the idea of self-improvement. Latching on to the tradition and zeitgeist of ritual renewal that takes us by storm every bleak midwinter.

How are your resolutions going? Still keeping them? Do you even remember them?

New Year’s resolutions are stupid!

Yeah, unless you make them SMART…(haha get it?)


Well...for those who’ve been under a rock, I’m making corny puns about SMART goals. SMART of course stands for:

  • Specific

  • Measurable

  • Achievable

  • Relevant

  • Time-based

It’s how you achieve results in an organized fashion. Codifying dreams into strategy. Companies and go-getters have been using the acronym for years. When I was a public middleschool teacher, making and tracking our SMART goals was part of the contract.

So how does SMART relate to NYE?

For some reason when it comes to making New Year’s resolutions, all those smarts go out the window. We imagine ourselves capable of silver-bullet changes, miraculous turnarounds—just because we resolved to do something.

But that’s not enough. That doesn’t even make sense. Just wanting something doesn’t make it happen. So why do we do it the not-SMART way?

Because making a promise is easy. Good intentions are easy. Sticking with a regimen of incremental progress takes some work. Mental work. Our least favorite kind of work.

On top of that, it’s the cool thing to do to make fun of people who make resolutions. Maybe because it sounds like just another damn fool ideological crusade...or maybe because they believe people don’t change. Or maybe they’ve tried before and failed, leading them to denounce New Year’s resolutions as generally stupid.

Which they are.

If they’re not SMART.

But why bother? What does it matter?

Because symbolic reset is a powerful device. That’s why every religion embraces it in some fashion. We go through life accumulating behaviors, thoughts, stances. Some fruitful, some junk. And like any functional system, our behaviors need a periodic tune-up.

The cliche holds true: We are creatures of habit. Grooving and falling into our own ruts. Patterns of behavior (good and bad) get burned into our neuron pathways and we just play on repeat. We can either deny the scientific truth...passively accept it...or we can bend that characteristic to our benefit.

The purpose of making New Year’s resolutions is to start down a 365-day path of self-improvement. Replacing bad habits with good ones. Self-improvement, like any other exploit, is a matter of practicing tactics to support a strategy. When’s the last time you ran a year-long strategy?

Think about it this way: a good New Year’s resolution is a narrative arc that gives structure to your year. It’s a thread around which to weave a tapestry of success.

Why New Year’s resolutions fail

The trouble starts with specificity. Most people promise themselves something hopelessly generic like:

  • Read more

  • Lose weight

  • Eat healthier

  • Quit smoking

  • Get back to writing/painting/music/dancing

  • Build my business and clientele

And they’ve forgotten about it by February. Back to the same old habits. Why? Because they didn’t narrow the focus. The scope was too big.

So let’s break it down:

Let’s say I want to lose weight.

Great, how much weight?

Ohh, 15 pounds should do.

That’s specific and measurable. Is it achievable? Certainly. I probably have 20-25 lbs to spare. Relevant? Of course. I’m a lifelong glutton. The crucial next step (and where most people fail) is breaking the goal into timely increments.

Here’s the process:

  1. Each pound of bodyfat stores about 3500 calories.

  2. So 15 lbs means 52,500 calories stored.

  3. Impossible all at once—that’s a month without food

  4. But across 1 year it breaks down to 1000 calories per week.

Can you cut 1000 calories each week for a year? Of course. Any American can.

Et voila! Lose 15 pounds in 2021.

Great but how?

Once you’ve broken down your goal into manageable terms, now it’s time to craft your resolution to help you nail down those increments week after week—times 52.

To do that I add another couple elements to the SMART equation:

  • Accountability

  • Stakes

  • Second-chances

That’s right, smartass—it’s SMARTASS.

And this is the fun part. This is where you can get creative. There are lots of ways to deficit 1000 calories from any given week:

  • Consume 200 calories less every weekday (that’s 1 pint of beer)

  • Pick one day each week to fast

  • Burn an extra 250 calories (run 2 miles) 4x per week (without eating more)

Same goes for any resolution. Reading: 100 pages per week. Smoking: use one less cigarette each week, starting at X. Business: pitch 5 new clients per week. Writing: spend 20 minutes 4x per week moving pen on paper.

And whatever SMARTASS thing you come up with, as the song says—don’t neglect the ASS.

Accountability: outsource your willpower

I’m privileged to have a merciless core of friends driven by honor and creative competition and self-improvement. All with different strengths and weaknesses and ambitions. Every year we organize our Enclave Resolutions Pool.

The rules are simple:

  1. Weekly reportable and reasonably challenging.

  2. Wager what you’re unwilling to lose.

  3. Last one standing gets half the pot.

  4. Finishing the year earns the remainder.

We report in via WhatsApp each Sunday and periodically someone declares defeat. And everyone else renews their determination. No one wants to feel that tail-between-the-legs admission of failure.

My friends and our honor system hold me accountable to my resolutions and give structure to my resolve. I’d never even consider breaking my word. So every day I know that if I give in, I’ll have to announce that I’m out.

Involving a community fortifies your willpower. But it’s the stakes that fuel the game.

Stakes: intrinsic vs extrinsic

The key to incremental achievement is separating the goal from the strategy. Which means adding an extrinsic reward to your gameshow of one.

Of course it’ll feel great to lose 15 pounds—but that’s not a tangible process. Healthy weightloss is achieved slowly, methodically. You can’t feel yourself burning fat gram by 9-calorie gram. Weightloss is a result. A goal.

Resolution is the steps you’ve decided upon for getting there. So here’s what a SMARTASS weightloss resolution might look like:

  • Goal: Lose 15 pounds by 2022

  • Resolution: Each week I will exercise 80 minutes total and designate one 1000-calorie day

  • Stakes: $100

Easy peasy, right? Separate the result from the reward, and it becomes a game. And the weekly structure allows for day-to-day flexibility and planning ahead. Miss a few gym days from travel? Jump on a bike for an hour and a half on Sunday. Get back in the groove next week.

As for the stakes, maybe $100 doesn’t seem like a lot of money—but every time you face temptation you’ll have to make that explicit choice. How much relief is $100 worth? How much is $1000?

Second-chances: gamify your habits

I’m only human.

The most brilliant justification of all time. There’s nothing we’re better at than justification, and that’s the best one.

So undercut your own brilliance. Build in a penalty system to give yourself a lifeline out of fuck-it syndrome. Something challenging but achievable; ideally relevant to the goal. Otherwise one slip-up and you’re out for the year.

For example, my 2020 fitness resolution was going to be:

Less than 1000 calories of alcohol per week

(Measured by tally as 6 reasonable drinks—I’m not gonna do math) But within the first week I knew I was going to break it. At some point my $150 wager just wouldn’t be worth it. No amount would be. Holidays, for example. Dinner with my in-laws. Say a friend shows up with a rare scotch. Sometimes I even have to drink for work.

I needed a workaround. So I added a failsafe:

Less than 1000 calories of booze per week (6 reasonable drinks)

Or for each drink over six, I have to run 2 miles the next week.

Daunting enough to enforce moderation...manageable enough to still have fun. Not to mention, running two miles burns more than a drink’s worth of calories—so I’m actually going above and beyond.

Boom! Gamified.

The result? By March I'd lost 15 pounds. Never even picked up the dreaded Covid weight.

What self-improvement are you working on?

A challenge, dear reader, should you choose to accept it

  1. Make or renew three resolutions: fitness, business, personal.

  2. Break them down into weekly components.

  3. Set your stakes and second-chances.

  4. Find your accountabilibuddy.

  5. Let me know how it’s turning out.

Want to know what my 2021 business and personal resolutions are?

Start reading The Write Stuff