Many job postings include a required skill for candidates to display “comfort with ambiguity”, a definition that itself can seem ambiguous alongside harder skills such as experience managing people, knowledge of particular technologies and so on. So what is this strange personal trait, and how can we develop it?
Comfort with ambiguity refers to the ability to navigate situations in which there is uncertainty, incomplete information, or no clear answer. It means staying productive, adaptable, and confident even when outcomes are unclear or the path forward isn't fully defined. In fast-changing or unpredictable environments, such as the tech industry, it is a key skill for maintaining productivity, and can often be the dividing line between those who sink or swim when the waters get rough.
For software engineers, one way to frame career progression is to think entirely in terms of comfort with ambiguity:
- Junior engineer - Clear problem, clear solution, clear implementation
- Mid-level engineer - Clear problem, clear solution, ambiguous implementation
- Senior engineer - Clear problem, ambiguous solution, ambiguous implementation
- Staff engineer - Ambiguous problem, ambiguous solution, ambiguous implementation
Your capability to efficiently deliver value in increasingly ambiguous situations - up to the point where even identifying the problem to be solved is unclear - is a primary measure of your career progression, and an important axis of growth.
Finally, if you wish to operate at CTO level, as an entrepreneur, expect to throw all certainty out the window. No longer are you painting by numbers - or even facing a blank canvas. You must choose your medium, your subject - everything!
Thankfully, there are many ways that you can develop this skill over time. Let’s talk about a few of the main ones.
Always be learning
As an engineer (or any technical practitioner), your starting point on this journey is to build the foundation of your craft. This is best done by developing both a breadth and depth of technical expertise, focusing on learning all that you can and never staying still.
How does learning help? It helps you develop pattern recognition, a key skill in responding to ambiguity. By encountering novel situations, but recognising elements of them from your prior experience, you will start to develop the ability to tackle situations that differ from those you have previously seen. This is responding to ambiguity, and it is the muscle that you will strengthen through your entire career journey.
Push your limits
Sitting and waiting for intellectually challenging situations to come to you will work well at the start of your career. But if you want to avoid stagnation, you will need to push yourself outside of your comfort zone. To be comfortable with ambiguous situations, you must regularly expose yourself to them.
How can you do this? Be intentional - find work that stretches you, either by working on systems (or parts of systems) with which you are less familiar, or by taking on tasks that reach beyond your current skill set. This could mean designing a new component from scratch, digging into data on a system you never worked on, trying to fix a bug that someone else has failed at - or a hundred other possible tasks.
The requirement is that the first time you do it, it should be difficult. The benefit is that the first time is as difficult as it will ever be - next time will be easier, and the time after that even easier and so on. And then you will have new limits - and will need to push those too.
Own it
Once you have a good process for identifying ways to grow your ability to operate with increasing uncertainty, you have built the foundation to start talking about yourself as comfortable with ambiguity. Congratulations! Now you have to do the most uncomfortable thing - you need to start telling people that you’re comfortable with it.
Developing the ability to operate comfortably with ambiguity is pointless if you keep it a secret. You now have this great superpower - you can enter situations without clear boundaries, and feel your way through, looking for clues and signals, reasoning about possible solutions, even trying to define the problem by giving shape to the fog.
But get ready for the double edged sword - because once people know you can survive in situations like this, they are going to start throwing you into them. It is at this point that you need to think about how to cope with this new wild, unbounded world without rules that you built for yourself.
Reduce cognitive load from uncertainty
Albert Einstein wore the same suit every day; Steve Jobs always wore a black turtleneck and blue jeans. Removing uncertainty from other parts of our lives means that we reduce the amount of decision fatigue that we feel. And when operating in spaces of great uncertainty, this is vitally important if we want to remain comfortable and effective.
I don’t personally wear the same clothes every day, but there are a bunch of ways that I have developed techniques to reduce my cognitive load and allow me to operate more effectively when dealing with ambiguous situations. These include:
- Mindfulness - regular meditation in which I practice clearing cognitive load by focusing on breathing or other simple things
- Habits - atomic habits, driven from an app, that help me progress on my defined goals without the need for short-term decision making
- Calendar planning - using a tool to map my to-do list out over time, so that I minimise the effort spent on thinking what to do next, and can block out time for deep thinking
- Journaling - the daily practice of unloading my thoughts on diverse subjects, enabling reflection and getting ideas out of my mind and down into writing
- Automation - where I can, I automate activities to save myself time, such as getting an email for each friend’s birthday rather than having to remember to look them up regularly
These are some ones that work for me, but you can build your own by identifying any situation in which you’re tempted to delay something because you’re just too tired to think about it, which is a sure indicator of decision fatigue.
Being comfortable
Putting it all together, we can strengthen the muscle of being comfortable with ambiguity by:
- Focusing on learning
- Operating outside our comfort zone
- Letting others rely on us for difficult tasks
- Eliminating decision fatigue
If you are able to do all of these, then congratulations! You have developed the superpower of comfort with ambiguity, and are now ready to sail across an ocean of new possibilities, undaunted when the shore slips over the horizon, and prepared to brave whatever turbulent waters lie ahead.