Football pitch

Last month at SXSW two keynotes changed the way I think about three key things every entrepreneur needs: habits, bravery and vulnerability. The first was an inspiring session by Gretchen Rubin, author of the Happiness Project on ‘The Five Counterintuitive Truths About Habits’. The second was an awe-inspiring session by Brené Brown called ‘Daring Greatly’.

“If we have habits that work for us, we are more likely to be happier, healthier, or more productive,” says Rubin. Habits get us out of the business of using self-control and making decisions – but many of us have trouble forming a habit even when it’s something we love to do.

There are apparently 21 strategies to change a habit but the key is to set one up in a way which works for you. Some of us like to start early and plan, while others like to be up against the deadline – “some are abstainers and some are moderators,” Rubin says. Can you eat one square of chocolate every so often or (if you’re like me) is it unlikely that bar of chocolate will last out the day? For abstainers, it’s easier to have none than a little bit. Now you can start to see the roots of an office conflict or a domestic spat…

Rubin cautions against going for ‘the big goal’ like a marathon or no alcohol or sugar for a month – setting up a finish line instead of creating a habit means people usually return to their old ways. We each have four tendencies of how we as individuals respond to outer or inner expectations. If we understand these and can recognise them in others, we can increase our motivation:

Upholder: they uphold both internal and external expectations and therefore tend to be easy to work with- but often can become so conscientious that they often can’t let go of rules and lose sight of real priorities.

Questioner: they question expectation and only do something if it makes sense – they hate irrationality, or arbitrariness; they make everything an inner expectation – if they don’t’ believe it they won’t do it. Know anyone like this? Questioners can be useful in the office because they keep everyone on track. But set them some firm deadlines or they may suffer from analysis/paralysis.

Obliger: these people strive to achieve all outer expectations, but struggle to meet inner ones. Because they are ‘pleasers’ (and most people are), they get along the best of all the other tendencies. But how can Obligers meet inner expectations? By setting external accountabilities – eg through a coach or mentor.

Rebel: these characters resist all expectations – do what they want in their own way, in their own time (few people are truly rebels) They are exciting to be around – but they can’t even tell themselves what to do, which can also be frustrating or even crippling for the rebels themselves. If you want to get a rebel to do something – tell then it can’t be done. Note, the most stable pairing is a Rebel with an Obliger.

Overwhelmingly people are Ouestioners and Obligers – Upholders and Rebels are on the extreme. These are not related to age, gender, time/place. These are deep parts of our personalities. Which one are you?

Now let’s combine this insight with some wisdom from Brené Brown who started her talk with a quote from Roosevelt: “It’s not the critic who counts. The credit belongs to the [wo]man who is actually in the arena. At least when [s]he fails, [s]he does so daring greatly”.

Brené espouses ‘choosing courage over comfort’ where possible because “there is zero innovation and creativity without failure”. So how do you choose to ‘be in the arena’ – and the vulnerability of trying and failing? Brené calls the process the reckoning, the rumbling, and the revolution:

The Reckoning: “When something difficult happens, our emotions get the first crack at understanding it. We like to think we are rational thinking beings who can flick things away – but we can’t.” However, people who recognise the moment they’re in and recognise the emotional involvement can then choose to act in the way that is consistent with their values. So pay attention for clues.

The Rumbling: This is a conspiracy story with limited data points that you fill in with your own values, fears, and beliefs. “In the absence of data…[our brain] will create a story – it’s how we are wired”. She calls them “Confabulations – lies told honestly.” But we have to challenge the conspiracies and confabulations, because “there is always an ‘SFT’ – shitty first draft” – the first story we tell ourselves about what’s happening when we’re in an emotional or uncomfortable situation. Here’s the rub: “When you own your story, you get to write the ending. When you deny a story, it owns you”.

The Revolution - This is the moment when you own the story, and become unstoppable.

By Diane Perlman, CMO, MassChallenge