Life Lately + Book Summary - Decisive: How to make better choices in life and work

"Two roads diverged in a wood and I - I took the one less traveled by, and that has made all the difference." - Robert Frost

While scrolling through LinkedIn during the past week, I saw an update from someone who had made me a fantastic offer for a role in Product Management at an American Industrial Goods company towards the end of my year in business school. For a brief moment, I let my mind wander and explore what could have been if I had taken that offer, or any one of the other offers I received towards the end of that year.

This doesn’t happen often, but from time to time something will trigger retrospection and I’ll wonder for a few moments what those paths may have held. I always come away from these moments thinking the same thing – I followed an exhaustive process to make my decision and I made the best decision I could have made. As icing on the cake, detailed essays spell out the process I followed, the factors I considered, and the conclusions I reached. 

I think it is powerful to be able to move forward knowing I made the best choice I could have made. It means there is no lurking regret, no wishing I had done things differently. When I went through challenging patches in consulting such as a lengthy period on the bench or a poorly-defined project, I could think back to how I had chosen that position and trust the process.

I often speak to people who are facing similarly important choices. I don’t talk about marriage – way above my paygrade, but I often speak about choosing among job offers, whether to relocate from Nigeria, which business school to attend, and other such privileged choices. For these conversations, I reach for what I now think of as the Swiss Army knife of decision making.

The most fundamental part of the process is personal to everyone. There are many names, or questions if you prefer, for this part. This is the “why?”, the “what are you about?”, the “what do you want?”, the “where do you want to go?” My approach so far has been to try to clarify this in advance – before I am faced with any defining choices. This is because the existence of choices can anchor us and frame our options, so it is best to know what we’re all about before we have to make a choice. Note the answers can change over a lifetime and that’s okay too.

The rest of the process is something I figured out over many attempts through the mid 2010s. I then realized in 2019 that Chip Heath and Dan Heath had codified it even more beautifully in their 2013 book Decisive: How to make better choices in life and work. I present a brief summary of their work below but strongly recommend reading the book.

The book is anchored around what Chip and Dan call four villains of decision making. Narrow framing, our tendency to define our choices too narrowly, to see them in binary terms. “Should I work in consulting or not?” Narrow framing often causes us to miss options. Confirmation bias, our tendency to develop a quick belief about a situation and then seek out information that bolsters our belief. “Product management is the best choice for me. Here are ten reasons why.” This often causes us to ignore or discount information that doesn’t support the conclusions we’ve already reached. Short-term emotion, well – emotion is emotion! We replay the same arguments in our head and can sometimes focus on things that don’t fully align with our core priorities. “The industry doesn’t align with my objectives…but the money! All that stock!!!”. Overconfidence, thinking we know more than we actually do about how the future will unfold. Humility about what the future holds is so important!

The brothers then lay out four broad sets of tools for tackling these different villains. To combat narrow framing, widen your options as much as you can. Once you find yourself framing something in binary options (to do A or not) – it’s a sign that your frame is narrow. The question should not be “should I go to college A or not?” It should be “what is the best option to get me where I want to go?”

To combat confirmation bias, reality-test your assumptions. What are the core assumptions underlying the choice you’re making? If you’re about to move to a city because you think it offers the best choice to break into an industry, how many people have broken into your target industry by moving to that city? Actively seek out information that undermines, not bolsters, your belief. Ask questions that can surface contrary information.

To combat short-term emotion, attain distance before deciding. This is what I was getting at when I described figuring out what you’re about before you’re faced with any choices. When you’re clear what you’re about, it’s easier to say “The money is a lot but I’ll take less money for now to do X because it is more likely to get me to Y”. There are still ways to limit the role of emotion if you didn’t do this in advance. For example, assign weights to all the factors that are important to you and then assess your choices against each factor. The emotion will not go away, but you’ll make some room for logic. And don’t discount your gut too – your instincts can sometimes recognize things you can’t explain. We flew somewhere in Europe to check out a potential employer in 2018 and we loved the experience until I walked into the office the morning after we arrived and immediately knew (& texted Busola) “I won’t be happy here”. (This offer still went through my process anyway – but I knew from Day 1).

And lastly – no matter how solid your process is, you have limited control over how things turn out. Don’t be overconfident about the future. There will always be variables you did not model for, things you did not anticipate. Consider that the future may bring many possibilities and prepare to be flexible. Trust that you followed a good process, and then go forward fully prepared to pivot when required.

We don’t need to go to this level of detail when choosing whether to wear a white shirt or a blue one (wear white please) – but I hope this helps to some degree when next you’re faced with an important choice. And again – read the book!

May the road rise to meet you.