What Does Your Picture of Success Look Like?

In his excellent book, ‘Essentialism‘, Greg McKeown recounts how “Jim Collins, the author of the business classic Good to Great, was once told by Peter Drucker that he could either build a great company or build great ideas but not both. Jim chose ideas. As a result of this trade-off there are still only three full-time employees in his company, yet his ideas have reached tens of millions of people through his writing.”

This anecdote remind us of something that is absolutely critical. As we try to live deliberately, we each have a different picture of success that we are aiming for.

Yet for some us, we’ve never stopped to consider what indicators will tell us we are moving forwards in the story of our own success – the success of living a deliberate life of our own design; one that honours what is most important to us.

The indicators that tell me I am succeeding in the life I want to live may not be the indicators that you are living the life you want. They may in fact tell you the opposite.

We can tend to gravitate to ‘the usual suspects’ when it comes to gauging success – both our own and others. Growth in a business, bigger opportunities at work, financial prosperity – more numbers and more dollars. But these are quantitative, not qualitative. And growth for growth’s sake is not always the desired result.

Yet it’s so easy, even without realising it, to start aiming for success indicators that belong to the paths of those around you, instead of indicators that are meaningful for you personally.

So not only do we need to be deliberate about the way we live our lives, but also about the way we orient and measure it.

What are you trying to build, and what kind of path will let you do that?

Do you want to see change in a social injustice?

Share great ideas?

Connect customers with great products that will improve their lives?

Create a healthy, loving home environment for your family to flourish?


Each of these will require different sacrifices, and result in different indicators of success. You probably can’t do them all. So what will you choose?

Asking ourselves 2 simple questions can help us to define the kind of path that will get us to the life we are trying to live:


1. What am I trying to build with my life?

You can certainly try to answer this comprehensively, across the whole of life – to ask yourself what your one big thing is. But you can also choose a particular time-frame (such as 6 months, 2 years, 5 years…) or sphere of life (such as health, career, family…).

Answering a question like this often requires us to distinguish between what we simply can do, and what we are really great at, passionate about, and feel a call to accomplish.

If you really want to develop one aspect of your life or skill set, but keep taking up opportunities that are offered to you around another, you may be building a form of success that is actually preventing you from building the kind you really want. It’s important to articulate what your picture of success looks like, so you know how to forge a path to get there.


2. What kind of signs will tell me I am on the path I want to be on?

If you feel passionately about, for instance, pursuing your art, then you will be looking at indicators like:

– whether your rhythm of life allows you enough margin, and time to practice, that you feel a good flow of ideas and creativity

– whether you are getting enough exposure to other forms of art that stimulate your own thinking

– whether you are completing pieces, or endlessly revising

– whether you are getting your finished pieces in front of other people

If, on the other hand, what you want to build is a community of like-minded business people who can mentor emerging leaders in your field, then your indicators will naturally look very different. In your case, getting along to lots of local art and theatre may not necessarily tell you anything about whether you’re moving in the right direction!


Unless we know what we are really trying to deliberately build with our lives, and what signals will tell us we are moving in that direction, then we can easily get off track. We can interpret any kind of momentum as success, when it may in fact simply be a distraction.


Let’s be deliberate in painting the picture of success we are aiming for!