Comfort In The Discomfort
Exploring the essential balance of humility and confidence needed in the world of innovation and design strategy. Drawing from a conversation with a Fortune 50 company's experience strategist, this post delves into the concept of being 'comfortable with the discomfort' – a crucial mindset for tackling complex, 'sticky' problems. Embracing both the unknown and one's ability to learn and adapt is key to transforming from a questioning student to a confident strategist. This post is a must-read for anyone looking to thrive in challenging professional landscapes, demonstrating that the true art of strategy lies in balancing knowledge with the eagerness to discover.

Author : Dwayne King
10 November 2023
Mastery Culture
Leadership
Knowledge Leverage
Recently, a former colleague, Johnny Servin, forwarded an email he had saved that I had sent the team after a meeting. He said he still refers to it, and it's 5 years old. I hope some of the thoughts in it may be helpful to others as well.
First, some context: I had an interesting exchange with a customer that's an experience strategist at a Fortune 50 company. I'll spare you the details, but I was working on a complex digital experience strategy for them...and the request was vague at best.
As we were nearing the end of a call, the client asked, “What more do you need from us to get started on all this?” I told him nothing, and that I’d like to get started to get stuff in front of them to see how it’s resonating and adjust from there. He was excited and said that he knew I was the right guy for this project when he called me about it. I came clean and said up until about 4 days prior to that call I really had a fuzzy idea of what they were trying to do and no idea what I was going to deliver. But, I said that I’ve also worked on enough of these to know—even when I was scratching my head—that I’d figure it out and come up with a solution. His response was (in his wonderful German accent), “Ah yes, you are comfortable with the discomfort, yes?”
I thought that was an interesting way to put it and thought it worth sharing. I tell people in sales calls, when they talk about their problem being sticky and complex, that people don’t call people like us if it’s easy. We solve the hard problems that freak other people out. And I think it’s because we're comfortable with the discomfort. I think to be successful in innovation and design strategy, you have to be comfortable with the discomfort. This ties back to how I think you should approach every professional problem you encounter, “transforming yourself from questioning students into confident strategists on every engagement.” (thank you to another colleague, Eva Miller, for articulating that so well originally). Ultimately, I think there’s a yin and yang thing that you need to balance when we get into some of this deeper design strategy:
- You have to be humble enough to walk into engagements knowing and accepting that you don’t know squat. What you think you do know…it’s wrong (and if you hold on to those things you think you know, you’re going to fail).
- You have to be confident enough to know that if you ask questions and really listen to the answers…I mean really listen, to not only what they’re saying, but also what they’re trying to say and what they’re not saying, you’ll start to gain a deeper understanding of the issue than even the people telling you about it.
That understanding of the issue is critical, as the person that is best able to truly articulate a problem is the one most likely to solve it.
Tying back to the student-to-strategist transformation, think about your first calculus class, you probably didn’t know what a derivative was, let alone how to find one. But when the instructor started talking derivatives, hopefully you didn’t get up and run because you didn’t understand (lacking confidence to know that you will one day understand). Hopefully you also didn’t try to use your knowledge of geometry to understand the change in slope (lacking the humility to understand it’s fundamentally a different kind of question, though may seem similar in some ways).
To wrap this all up, if you think you have, or can develop, the dichotomous need to be humble and confident…to get comfortable with the discomfort, I have no doubt you’ll be successful at innovation and design strategy work. Where people will struggle, is if they can’t let go of thinking they know the answer, or cannot trust that they will know the answer.
Update From Blog
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