Perfect Day Upstartist Diaries

Outsight, then Insight

“Outsight, much more than reflection, lets you reshape your image of what you can do and what is worth doing.” – Herminia Ibarra

Have your breakthroughs in identity come from action or reflection?

Most best-selling career books ask you to start with self-reflection.

Strengths Finder

What Color is Your Parachute?

Do What You Are: Discover the Perfect Career for You through the Secrets of Personality Type

(all great books!)

But my new identities – of what I could do or be – were all discovered through trial and error.

I never imagined that I’d be a TV basketball announcer. But my friend needed an emergency replacement. Two years later I had commentated 20 games for the Saigon Heat, Vietnam’s first professional sports team.

I never thought I’d host a podcast. I tried it for fun. Five years later, I’ve hosted over 150 episodes of the Touch MBA Podcast, which has helped thousands of applicants get into top-ranked business schools.

I didn’t think my way into these new roles. I just gave them a shot.

Professor Herminia Ibarra has researched workplace identity for decades, and taught an MBA course “Leadership Transitions” for over 10 years. In 2015 she wrote Act Like a Leader, Think Like a Leader sharing her research that people become leaders by doing leadership work. She calls this outside-in approach to change outsight.

“Our mind-sets are very difficult to change because changing requires experience in what we are least apt to do. Without the benefit of an outside-in approach to change, our self-conceptions and therefore our habitual patterns of thought and action are rigidly fenced in by the past. No one pigeonholes us better than we ourselves do. The paradox of change is that the only way to alter the way we think is by doing the very things our habitual thinking keeps us from doing.

This outsight principle holds that the only way to think like a leader is to first act: to plunge yourself into new projects and activities, interact with very different kinds of people, and experiment with unfamiliar ways of getting things done. Those freshly challenging experiences and their outcomes will transform the habitual actions and thoughts that currently define your limits. In times of transition and uncertainty, thinking and introspection should follow action and experimentation—not vice versa. New experiences not only change how you think—your perspective on what is important and worth doing—but also change who you become.”

Outsight is at the core of living my perfect day.

Why? I have to live my perfect day to test the assumption that it is perfect. There is no other way to know. No amount of thinking, self-reflection and personality tests can match outsight.

If you’re already living your perfect day – being, doing, and having what you want – then outsight is less important. But I’m guessing most of you are like me, and want to transition into something new and different. Then what’s needed is experimentation before introspection.

It’s hard to disagree with Professor Ibarra’s logic:

  • The way you think is a product of your past experience.
  • The only way to change how you think, therefore, is to do different things.
  • Fresh external perspectives – rather than internal reflection – accelerates your understanding of a new role / identity.

I’ve read hundreds of self-help books and confess this is true. It’s easy to hide behind reading and avoid the real work of doing. Evolution demands action, adjustment and iteration. Starting two companies – not reading books – helped me understand entrepreneurship.

That’s why I commit to at least one action per book I read. After I read the Art of Gathering, I implemented a “no paying for your own drinks” rule at my birthday party. After finishing Deep Work, I experimented with “fixed schedule productivity,” not working past 7pm. I observe what works and what can be improved.

Ibarra identifies three sources to gain outsight:

  • New ways of doing your work (your activities)
  • New relationships (your network)
  • New ways of connecting and engaging people (your self)

While intended for workplace transitions, these can also be used for designing your perfect day. If part of my perfect day is to meet with inspiring people over lunch, what new activities, relationships and ways of connecting can I experiment with daily to get there?

She also encourages us to be more playful with ourselves during the process

“As much as transitions require us to move way beyond our comfort zones, they can also trigger a strong countervailing impulse to protect our past identities. We easily retreat to old habits, especially those that have been rewarded in the past.

Making significant changes, not just in what we do but how we do it, requires a playful frame of mind. I recommend that people think of leadership development as “playing with” rather than “working on” themselves (which, let’s face it, is not much fun). When we adopt a playful attitude, we’re more open to a diverse, even divergent, set of possibilities.”

I try to design play into the unfamiliar parts of my perfect day. We’re allowed to play as kids when learning is effortless, why not as adults? Does growth have to always come after a grim slog of sacrifice and determination? How can I make my stretch activities and relationships more fun?

Act your perfect day to know your perfect day

Outsight, much more than reflection, lets you reshape your image of what you can do and what is worth doing.

Herminia Ibarra, Act Like a Leader, Think Like a Leader

Private Email List

Get tools, tips, and resources direct from Darren on surviving and thriving as a solopreneur (plus, thoughts and announcements never posted publicly).

Leave a Reply