✍️ 01b. Lacking clarity? You need a Creative Offsite
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✍️ 01b. Lacking clarity? You need a Creative Offsite

Simon is a General Partner at Helix Collective, a venture studio + seed stage VC. Previously, co-founder of a telco infrastructure company and junior partner strategy consultant.

This is part two of a three part series.

See part one on my results of the Creative Offsite and what they mean to me, and follow up with part three on the application of this process to business planning.

This episode contains the steps to run your own Creative Offsite and why you might want to.

Creative offsite: The process

If my mind gets too excited, it will go too narrow too fast. So I like to develop processes that encourage breadth. Enough space to engage logic as well as feeling, neutralise as many biases and reactions as possible, and hone in on clarity.

The more I care about the answer, the more excited I get. The more excited I get, the more space I need to find clarity.

But how to structure the right process to give that space? Balance going with a flow vs steeling yourself for a challenge? Invite external reflection vs avoid unhelpful influences?

I started exploring reflection and self-enquiry processes since I was a teenager. I became dissatisfied with the standard priorities handed to us and so began years of notes, scratches, discussions, reflections, mental circles, and at times, new insights.

This is my favourite process by far: The Creative Offsite. Enthusiastically inspired by this podcast @1:28.

It works like this:

  1. Find 1-3 other people who are collectively willing to be honest about their deepest hopes and desires.

Warning: it will be bugged from the start if anyone is holding back or not trusting the group. Think about who you invite carefully. The real value comes from pushing to a new level of self-honesty, beyond what you know about yourself already. This is hard work, and you have no chance of getting there if the group is being filtered, reserved, or not trusting.

  1. Get together for a dedicated 1-3 days, ideally somewhere quiet, spacious and unassociated with existing routines.

We are heavily influenced by our mental and physical environment. You need to completely clear your calendar, commitments and regular routines. Ideally, switch off notifications. Best if you can find a relaxing place to stay together, not your office or home with existing grooves of thinking and behaviour.

  1. Take turns to create a downdraft, where you brainstorm anything and everything you might want this year.

One person takes the stage and gives a stream of consciousness as unfiltered as possible. The attitude you take is key here: nothing you say matters. You don't have to really want it, you certainly don't have to do it. You want to de-filter yourself as much as possible to allow any new creative thoughts to emerge.

The rest of the group has a few really important roles:

  • Encourage free expression of the speaker by being interested, engaged, and actively dissuading any kind of filtering
  • Take notes so the speaker doesn't need to remember what they say, making it easier for them to get in a mindless flow
  • Listen for threads from the speaker that feel bright, animate their spirit, and feel incompletely explored - and ask questions to pull on the thread

The group makes no statements, they only exist to ask questions that help the speaker find rich unexplored veins of desire within themselves.

Move on once the speaker feels that everything they might want this year has been spoken, across all parts of their life, and captured onto messy pages of notes.

  1. Take turns to create an updraft, organising the mess into a few themes and projects that feel the most exciting this quarter.

I'd recommend solo time to reflect and prioritise before starting this step. Solo reflection is valuable but probably less valuable than it will feel. Every time I've run this process, everyone - including myself - has completed their own prioritisation and felt it was "done" and only needed a short round of group discussion. A few hours of discussion later, the updraft was significantly better.

Organising and shaping priorities is more art than science. There are many ways to organise very similar objectives, and the way it is shaped matters. The right way of writing it down will be like getting a click, it will feel right and be logically crisp. If it feels vague, or 'not quite right', it's unlikely to change your life.

My preferred way to organise is to start by looking over your mess of desires and identify themes that feel the most important to you right now. These are often a little more abstract and reflect a part of yourself or your life that you want to develop. For example, be freer, be more creative, grow my business, or improve my relationships.

Once you have some themes, look over the messy list again and find specific projects you could go after this quarter that feel the most exciting and most impactful to progress the theme in your life.

Unlike themes, projects must be specific. The more clarity you can bring to exactly what shape it takes in your life this quarter, the better. You need it defined well enough to know when it is complete. You need to be able to see how you would track progress. Use your crew to bring extra clarity, bouncing a project shape together.

Finally, hunt for things to say no to. The process is like whittling away the deadwood to reveal the perfect shape of your themes and projects. You have everything in the downdraft already. The updraft adds value by saying no, not this quarter, to as much as you can. The fewer things you have to focus on, the more force you can apply.

  1. Polish the updraft and make it visible in your daily routine.

For me, this is a solo activity after the offsite is complete. The week following, I reflect on the updraft and normally find a few pieces that still feel vague or need further specification. I take time to work through logistics, timing, and make it practical.

Most important is that you integrate it into your routine. Peak uselessness would be to never look at it again, and go about your quarter in a regular routine. If nothing changes in your day, nothing changes in your life!

I do this in two ways.

First, I take the offsite updraft and I convert it into a google sheet using this template. This sheet is set up like a metrics tracker I would use for a business. The value in this to me is that it forces me to write down how I would measure the project, which brings a whole new level of clarity to what I will do over the quarter.

I think it's less important to actually measure it weekly than it is to do the upfront work clarifying how you would measure it and what specifically you are going to do. Harness the spaciousness and clarity of the offsite to push your thinking into actual changes you're going to make in your week!

Second, I create a list in my to-do app for every project. I allow a few other lists that are unrelated to what I selected for my themes and projects, but I want to look every day at my projects via this app, and reflect on if I'm picking things to do that are pushing the projects I'm excited about forward, or some other (perhaps less exciting) task.

This I find a very powerful step, as it encourages me to reorganise my mental model of 'what I have to do', through the lens of my selected projects and themes.

I take great delight in going through all my to-dos and copying across those that fit within the new projects and deleting everything else I possibly can.

Creative offsite complete. I'd recommend catching up with your crew at least monthly to check-in and help hold each other to the standard you set for yourself. Settle for nothing less!

Criticisms and questions

This is not one size fits all.

Here are my most common criticisms of the process and my personal reflections.

Isn't this just goal setting?

Kind of. But the real value here above what most people would normally do by 'setting goals', is that you a) create an unusual amount of space to let new priorities emerge, b) leverage trusted friends to help pull you deeper than you may have otherwise gone, c) use those friends to bring better shape to those goals, and d) push the goals into an unusual level of specificity and integration with your week.

If this is what you do when you set goals already, well, awesome! I'm just catching on ;)

Setting a plan doesn't work for me, everything good comes from following the flow.

I'm a big believer in following flow. The more you can organise your day to spend time on what feels right, what feels in flow, what animates the spirit, the better. This exercise is not about creating a rigid plan for yourself so you can lock on and cut out spontaneity from your life.

In fact, if you get one month in and something new emerges more bright, exciting, and impactful you should follow it - plan be damned. But I would recommend using some self-awareness to identify if you're the kind of person that gets easily rigid, and so should allow and follow more impulses as they emerge, or something that bounces around rarely getting anywhere, and so should buckle down and drive yourself to completion every now and again.

Rather, this exercise is about creating space, and listening carefully, so you can find the most valuable, subtle, quiet flows inside of yourself and follow them.

I would argue that this process is designed to tap you into the right flow because we live in an over socialised noisy world that drowns out the quiet voice of what we care most about.

This is hard, my brain just doesn't organise things into measurable projects.

Some people will more naturally think in a quantified, logical way. Others will be better at perceiving the subtle feelings in themselves and others that might give clues as to where to probe further in group discussion.

Try to find people to join you on the offsite that have a mix of these talents, and use them to everyone's benefit. Not everyone needs to push the projects into the level of specificity I describe, it may be enough to have a well-described project or process that you intend to follow for the quarter.

But if this is not your natural style of thinking, find someone better at it than you, and learn from them. Everyone can develop both their logic and feeling based processing, regardless of how natural/unnatural you are at one of them.

Of course, the other option is to just not do a Creative Offsite. But.. that sounds boring to me ;)

Unexpected outcomes

Having completed my most recent offsite with my two partners at Helix, I was genuinely surprised at how well it replaced a top down strategic planning process.

I will run this for a few more quarters before concluding how lucky we got vs how truly robust the process is. However, I was shocked to find that our bottom up individual plans naturally led to a very sensible set of projects for Helix itself. Looking at the combined picture after we had finished, I couldn't help but think it was as good if not better to what we would have come up with in a traditional process.

And without a doubt, aligning the internal prioritisation and motivation with the business priorities, by working to those goals internally bottom up, will lead to naturally higher creativity and performance.

If you're curious about the application to business, keep reading in part three.

If you landed here out of context, you're welcome to read more about the answers I came to this quarter in part one.