Deeper Weekend 2014

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    Adrian Simmons
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    Scott Kregel

REFM -  Adrian Photo Square - CATOBThere’s a balance line somewhere between having everything planned out and having no idea what’s going on.

And the ideal is not ‘having it all figured out.’ There’s no reason to feel bad or punish yourself for not being fully organized. Chaos is a natural part of the picture — you can’t pull order from chaos without a little chaos. Which is why it’s okay to deliberately mess things up now and then. Or as we say in Thriveal parlance: blow things up.

When asked the question, “What does your firm want to be when it grows up,” it’s okay to say, “I don’t know.” Discovery really best happens from the side rather than head-on. You really can’t plan “a-ha” moments, or else it’s not really a discovery. Discovery is, by nature, unexpected. All you can do is put yourself in different places or situations where it might occur and remain open to it happening, without compulsion. A little trust in Providence doesn’t hurt either.

I was reading a blog post recently about “The Big Lie of Strategic Planning.” It goes into how we like to wrangle with the uncertainty of the future by applying all our sophisticated tools and spreadsheets as a way of making ourselves feel less scared. But the truth is we can’t eliminate all risk, and our attempts to do so are a merely an exercise in futility and self-deception, not to mention a waste of time that could be used for something else. Instead, planning is much more naturally a rough-edged process where we work out the basics and in the end decide whether we’re willing to accept, rather than fight against, the risk that is inherent in making the change. This is what good business is about.

One way I’ve started practicing this in my own planning is to:

(1) Define as best I can the destination of where I think I want our firm to go. What does that space look like in the various ways I can conceive it?

(2) Identify the main pieces needed to get me there. What are the key building components that enable that reality to exist?

(3) Describe as best I can the actions needed to construct those components, realizing my list will be incomplete.

(4) Choose the one or two components to work on next, and take the step I can see, working through the unknown as I go.

(5) Rinse, repeat.

Graphically, it could look a little like this:

Adrian's blog photo

The key is to walk boldly, and humbly, into the question: into the question of who you are, the question of where you’re going, who your customers are and what they can be, who your team is, etc. And don’t expect to see the end from the beginning, it just doesn’t work that way, especially with a landscape that’s in a continual state of flux, and a knowledge bank that’s continually adapting.

Every journey begins with a single step, but it also progresses by single steps too. Take the step you can see, the next one will become apparent from there, and not before.

  • On 05-05-2014 at 8:35 pm, Michael Wall said:

    Glad to be on the journey with you Adrian, thank you.

    • On 05-06-2014 at 6:23 pm, Adrian G. Simmons said:

      Thanks Michael — I’m glad to be sharing this journey with you too!

  • On 05-05-2014 at 9:12 pm, Philip Campbell said:

    Great stuff Adrian. It’s all about baby steps… and your rinse and repeat point. Lots of rinse and repeats!

    • On 05-07-2014 at 8:25 pm, Adrian G. Simmons said:

      Thanks Phillip! Absolutely – and each step helps us build strength for the next.

  • On 05-06-2014 at 5:09 pm, Melinda Guillemette said:

    This is such important thinking, Adrian. The combination of risk-taking and humility is powerful.

    • On 05-06-2014 at 6:26 pm, Adrian G. Simmons said:

      Thanks Melinda, and so true!

  • Jason Blumer

    On 05-07-2014 at 7:10 pm, Jason Blumer said:

    Good stuff dude! It was a revelation to be able to say “I don’t know.” I’m thankful you wrote about the opportunity to say “I don’t know.” So refreshing!

    • On 05-07-2014 at 8:27 pm, Adrian G. Simmons said:

      Thanks Jason! – We do often put undue pressure on ourselves, instead of seeing it as a process of discovery. Maybe instead of “fail forward” we can call it “discover forward”? :)

  • On 05-07-2014 at 9:46 pm, Doug Sleeter said:


    Great post.

    By thinking about what’s wrong with today, it helps us at least think about what could be better. Even if you don’t know exactly where you’re going, you should be really clear that it has to be different from where you are today.

    For example, I may not know exactly what will replace email, but I’m sure it will not be just another email client. For me, email has got to change. But I’m still not exactly sure how.

    Focus on the pain and then look for pain pills. Some work better than others.

    • On 05-08-2014 at 8:23 pm, Adrian G. Simmons said:

      Right on Doug! – and thanks for the comment! :) Absolutely agree that in today’s day and age, good self- and other- awareness, combined with a willingness to experiment, moves us forward one step at a time!

  • On 05-12-2014 at 6:53 pm, Joey said:

    Question: at a practical level how long does it take you to chew through 1-4 before you are ready to “rinse and repeat.” The time element would help me wrap my head around the size and scope of the components you are building. Do you try to articulate components that will take a month to build, a year, longer….? What is your opinion of the most effective time frame (size of building and testing project) to tackle.

    • On 07-09-2014 at 2:57 pm, Adrian G. Simmons said:

      Hi Joey! Great questions. Hmm…as I’m thinking about it, I’m not sure I’d let time determine the component sizes, but the reverse.

      I’m thinking our primary driver is to identify what will make a difference, and then do that; rather than identify the time we have to work with, and figure what can be done in that time.

      Which isn’t to say there isn’t some play between the two: practically speaking, there may be external time limiters like competition, product availability, event deadlines, etc.

      But letting value lead the conversation, and time be it’s second (pun intended), seems to be the order.

      Would love to hear your thoughts on the questions too!


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