How To Set Goals That Stretch

Traditional goal-setting isn't for everyone... here's an alternative.

You’ve heard of setting stretch goals, right? A stretch goal, usually used in the world of corporate goal-setting, is a goal that’s so big, it’s nearly impossible – if you reeeeally stretch, you might just get there.

Stretch goals are supposed to be this great carrot, urging you on to ever more and more productivity. That might be cool for a certain kind of “go team” personality. But for lots of people (including me), stretch goals set the bar so high that it doesn’t seem worthwhile even trying to get over it.

So for your realists out there, let’s forget all about stretch goals.

Instead, I want to teach you how to set goals that stretch.

A Few Examples of Goals That Stretch

A traditional stretch goal might look something like this:

I will travel the world for the next 10 years, earning money from my website as I go.


Maybe in the back of my mind, I do want to travel for the next 10 years, making money from my website. But when I put it in black and white like that, it’s terrifying. It seems completely unrealistic; laughable almost.

It makes me want to quit without even trying.

That gnawing fear is what keeps most of us dreaming of becoming a surfing teacher in Costa Rica or opening a B&B in Sicily, while we continue to live our same old same old lives in the country where we were born.

Here’s another example of a scary stretch goal:

I will ride my bike for 18 months, cycling more than 10,000 miles through 22 countries.

What?!? How the hell will I ever do that? That’s just impossible.

But wait. That’s exactly what Stephen and I did in 2013 and 2014. Only, we never set that stretch goal. Instead, we were able to do it because we set a goal that stretched.

How to Set Goals That Stretch

Start small. Sure, you might have huge dreams, but instead of jumping right in with both feet, try a “see how it goes” approach.

When we left on our cycling trip, I told everyone we would do a couple of months to see if we liked it. After all, we’d never cycle toured before. There was no way to know if we’d enjoy it, so why set a massive goal to achieve something we might hate? When we realized the first few months had flown by, we let our goal stretch, to Russia, to Berlin, to China, and beyond.

Allow for failure. Although our business cards said “Rome to Russia by bike” I was totally open to the idea of changing our plans. And in fact, we did have to take a ferry to Russia, instead of biking. In traditional goal setting, you would label that a failure, and hey, failure is OK. Personally, I like to call it a wise decision.

If you start out on a path and realize you hate that path, is it really a failure to go in a different direction?

Reassess and Course Correct. Once you’ve started out on a goal that stretches, it’s important to reassess frequently. Keep asking yourself: Is this working for me? Am I enjoying it? Is this what I want to be doing right now?

If you’re not happy with what you’re doing today, chances are you still won’t be happy with it in 2, 5, or 10 years, no matter what you have achieved.

Right now, my goal is something like this:

Put in place best practices for building an audience and making money from My Five Acres.

Right now, I am loving it. I am creating, learning, and making progress. Once all the steps I know how to do are nearly “done”, I’ll look at my goal again, and set up the next stage.

That next stage might take me in another direction altogether, as new opportunities arise from the work I’m doing now. I won’t know until I get to the crossroads, and I don’t know exactly when I’ll get there.

That’s the fun of goals that stretch, there are always surprises on the road ahead.

How To Set Goals That Stretch

A Caveat

In my mind, goals that stretch work well for people who want to be happy on a day-to-day basis; people who are not so worried about the traditional trappings of “success” like a big house, a fortune in the bank, a high-status job, and absolutely no time to enjoy it.

Setting goals that stretch have allowed me to move to new countries, learn new skills, explore different sides of my creativity, and create a life that is satisfying, every day.

That’s the only kind of success that matters to me.

Go top