Conform to be free.

As a sometimes awkward, sometimes I’m sure downright frustrating teenager, who just wanted to be, I always remember my mum giving me the advice “sometimes, you have to conform to be free”. As a headstrong thirteen year old, I did two things. I misinterpreted this to mean “you can’t always be yourself”, and I kicked against it with impotent teenage rage. But age and time give something that eventually looks like wisdom, and I now understand what she meant. That in order to free yourself, sometimes you have to work within constraints to ultimately unshackle from them. The whole concept reminds me of my favourite phrase from the Dalai Lama:

“Learn the rules so you know how to break them properly”.

So where does this take us. I want to discuss one of the most pervasive, and yet apparently benign mistakes that we can make in life. We assume in a huge range of contexts that widening our net as much as possible is the best way to collect things. This is often true. I had a conversation yesterday about why we should try to eliminate the effect of school years (that older kids tend to do better academically and in sports because they are more developed than the young kids in the year) on swimming performance. Australian sport have started to control for this effect in searching for the stars of the future, and why not? If you are looking for extreme outliers, like Olympians, then you want to filter as many of the population as possible. But, this doesn’t always hold.

In my mind, there are three places where we make this mistake which can be actively dangerous. Brainstorms, finding customers for startups, and in making our own career choices. I’ll address each in turn.

Brainstorming, done right.

The usual orthodoxy for brainstorming ideas is that we must first go through a process in which “all ideas are valuable, nothing is off the table”. We start with a light touch, a few bits of guidance from a facilitator, some calming music, and a clear sheet (or Miro board) ready for our post-its of genius.

The problem is, we are social animals, we want to be part of the group, so the first couple of ideas tend to guide the rest of the sessions. I have sat through many three+ hour versions of these which result in zero actionable ideas.

So what went wrong? It turns out that, because of the availability heuristic (see Kahnemann), if you give a group of people similar backgrounds the same broadly-defined problem, we tend to reach for the most available solution. The lack of constraints actually leads to a lack of creativity, because we aren’t forced to think, just to reach for ideas in the ether around us.

There is a clear need for guidance. Facilitators are there to provide guard rails, and to keep things on track, but that goes directly against the usually-stated approach to brainstorming, so ultimately they sit back and create an “anything goes” atmosphere. But this doesn’t yield the creativity they hope for.

Give people solvable problems, and they’ll give you solutions.

Who’s my customer?

Startups often struggle with this problem early in their lives. It’s of critical importance to understand early on who you are building for, and how what you are creating addresses a key pain point that they need to deal with. I don’t find it an exaggeration to describe this as a “hair on fire problem” as the EF founders do - why else would you take the risk on an unproven company that might have gone bust in a year? Because you have no choice…

So what’s the issue here? Well, most startup founders realise that they need funding of one form or another, and that means that they have to pitch. If they have to pitch, they want that TAM slide early in their deck to be in the hundreds of billions, such that investors take them seriously. The dialogue in their heads is “Imagine. If they only capture 0.2% of a $200B market, that still gives them a $1B valuation for a 25x earnings multiplier”. At no point does the less available, but arguably more important question “but how many decacorns have been founded this way” come to mind? And what’s a sure fire way to reduce that TAM number on your early slide? Reduce your focus to a segment of the customers out there.

If this all stopped at the slide deck, I would argue that it’s not such a huge problem. The issue is that this attitude bleeds out of pitches to permeate the early strategy of startups too. We all obsess over getting customers on board, not necessarily the right customers on board. With more customers, we’ll figure out where our product market fit comes from more easily, right?

Nope. See the problem is that those early customers will expect to influence your product roadmap, so you’ll end up building and maintaining features for them which might be very specific and particular to their problems. Without a strong product voice to stop this in its tracks, you can end up in a tyranny of the masses situation - a huge plethora of features, which are hard to differentiate, and a user experience that doesn’t promote choice.

Instead, focus. Narrow down to a segment. Find the early users that love your product, like the power sellers on eBay who formed the core of the paypal business model. Be something so some people, rather than the shmoo to everyone.

Careers

I realise I am perhaps being slightly controversial here, but I think we all tend to tunnel when we think about our careers too. I’m not na?ve enough to think that, like our parents generation, we are going to have thirty-year plus careers at a single company (and honestly, I think things are better for us all not to do that, but that’s a story for another day). However, we do still make choices about what we do in the various jobs we have. That’s what I mean by a career.

So, faced with a desire to change our path in our professional lives, what do we do? We dream, and let our minds wander on to whatever we think will be the most amazing, fulfilling career. It makes me think of the New Zealand island caretakers jobs, often dubbed the most fulfilling job in the world, and attracting thousands of applicants. Even I think that they sound amazing, but I also suspect that they are a lot harder and less fulfilling than they appear in our mind’s eye.

The reality is that in deciding to change paths, we are still operating under a lot of unspoken constraints, and that some conformity begets freedom. Take the island caretaker job above. Might there be some way that you can do a job more closely connected to what you’re doing now that would allow you to go to a remote island in NZ for two months a year? Might that actually be more appealing?

I bet that faced with that alternative your first thought was “but that’s an impossible dream”, whereas actually it’s probably more feasible than chasing the island caretaker job. Why so? Because by anchoring to reality, it suddenly feels “real”.

How do we do this kind of thing better? Don’t plan only for the destination, plan the whole journey. Don’t think about just “where would I go?”, but also think of “how do I get there from here?”. Once you start planning for the journey, you can start to make small steps in the right direction - maybe look for projects at work you can become involved in to move you to the next lily pad in the direction of your end goal. Operate under the constraints - you may need to stay close to parents, you may need to maintain a certain income to pay your mortgage, you might not want to pull your kids out of a school they love. Within those constraints, let your mind roam and wander to find creative paths.

There is so much opportunity in today’s employment market, and jobs spring into existence that were not only unlikely, but totally impossible half a decade ago. Know what your red lines are, the constraints you can’t break, and like the Dalai Lama says, know the rest so you can break them with all the creativity you have!