Man, it’s hard to change your mind.
I think this is a universal truth. It’s certainly hard for me, and I see how it challenges a lot of the leaders that I work with, too.
Conviction and vision are great things. But, when we hold too tightly to them, there’s a cost. We pursue strategies for too long. We don’t see new information. And we don’t let ourselves be influenced by others.
I see one of the central challenges of business—whether we’re talking about my small-but-mighty consulting firm or one of my Fortune 100 clients—as dealing with uncertainty.
Some problems are execution problems. You know how to do something, you just need to do it. You may need to do it faster, cheaper, or differently, but these are differences in degree, not in kind.
But others, like culture change, entering a new market, or creating innovative practices, require the capacity to sit with uncertainty.
That’s because these are “impossible problems.” Problems where we have a vision (but don’t know the exact answer), where we don’t control the people we need to implement things, and where we don’t control the broader system—the technology, organizational structure, incentives, and regulations.
Bets and Doors
When you don’t know the answer, every decision is a bet. Everything is an experiment. There are lots of ways of thinking in bets, but I like how Jeff Bezos talks about bets in terms of one-way and two-way doors.
Going through a one-way door is a big deal. If you don’t like what’s on the other side of it, you can’t go back through. You’ve already made the big acquisition, launched the new product, or expanded into the new market. These kinds of bets require analysis, sensitivity to the effects of complexity, and a high-functioning, creative team.
In contrast, two-way doors are easy to go back through. There may be a cost, sure, but the cost is small relative to the upside that you’re trying to capture. Reversible decisions can (and should) be made in a nimble way and, if things don’t work out, we should change course and try the next thing.
It’s a great philosophy. But the biggest challenge is admitting that you want to turn around and go back. Amazon has carefully cultivated a culture of experimentation that celebrates failure. That approach is hard for people and rare in corporate cultures.
Going Back Through My Door
The newsletter list has been growing a lot lately, but long-time readers will know that, from time to time, I turn the lens around to myself and my own business. So, I’ll share my own recent struggle with a two-way door and how I eventually turned back.
At the end of 2020, I saw an opportunity in the market to work with lawyers at small law firms. I decided to move into that market—launching a side business, setting up infrastructure, a mailing list, and even creating a product to help attorneys set better goals.
It’s an important market and work that I deeply believe in. And I had some good success cultivating new clients. Attorneys at small firms often need help. They’re deep experts in the practice of law, but they don’t always get training in the business of law. They also have a lot of upside potential: by improving their businesses and systematizing their processes, they can often increase their revenue and profitability, allowing them to serve more clients better.
But, a few months later, I realized that even though it was a great business, it wasn’t the business I wanted to pursue. I still love working with those clients; it’s just not where I’m putting my efforts going forward.
My energy lies in guiding leaders to solve their impossible problems by helping them learn to influence at scale. Particularly at big organizations, a small change in a leader’s perspective and practices can positively affect tens of thousands of people.
So, here’s how I went back through this particular door:
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I ignored the numbers and tuned into my feelings. This work with attorneys was a great business, both on the spreadsheet and in practice. But it didn’t capture my energy as I had hoped. When a task to draft a marketing email came to the top of my to-do list, I found myself dreading it instead of diving into it. That gave me pause and helped me realize that I needed to keep engaging with the decision to launch this side business.
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I stayed with the ambiguity. As I struggled with the commitment to market to attorneys at small firms, I knew something was up. But I didn’t reverse course right away. I didn’t want to have a knee-jerk reaction.
I also noticed what had my energy (helping leaders solve impossible problems, it turned out). All of this helped me deepen my sense of what wasn’t working and get to the point where I could commit to going back.
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I got a lot of input. I chatted about this decision with my team, guests on my podcast, my coach, and my mentors. One of my mentors, a master in his field, told me that our job as leaders is to “deliver ideas boldly—but hold them lightly.” We need to have a vision that drives us and be influenced by the feedback we’re getting from the world.
I tuned in to both sides of the spectrum.
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I made the big decision to stop pursuing this niche and used that to guide the many small decisions that followed. Even though I had invested time, money, and effort in setting up the business, I decided to pull the plug. And I used that decision to manage the work that had already been done.
The question my team and I asked ourselves was this: “If we were new leaders put in charge today, would we make the decision to…”. That allowed us to “forget” about why we had invested in a new platform to host our website, for example, and cancel the service.
It sounds so simple on paper (or when Jeff Bezos says it), but, in practice, it’s hard to go back through any kind of door. But, now that I have, I’m excited to have turned back to focus on something that has my passion and attention.
Are you dealing with an impossible problem? I can help. It’s simple!
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Book a free 15-minute strategy call here: https://chrisclearfield.com/impossible-chat
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I’ll call you at the scheduled time
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You’ll go away with a plan for how you can move forward.
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