Every time I watch the final scene of the movie La La Land, a quiet ache lingers in a corner of my heart.
Mia and Sebastian meet unexpectedly at a jazz club. As Sebastian begins pressing the keys, a dreamlike five-minute world of “what ifs” unfolds in both of their minds.
A perfect, happy parallel universe built on assumptions like “What if I had followed him instead of going to the audition back then?” or “What if we had stayed in Paris together?” Yet, when the song finishes and the lights of reality switch on, the two look at each other calmly from their respective places, share a slight smile, a gentle nod, and walk away.
In that gaze lay the poignant sadness and affection for the untaken path, along with a warm, genuine cheer for each other for living their lives to the fullest in their own places.
The Stoppage Created by the Illusion of a “Perfect Choice”
In life, and on project sites, we stand at the crossroads of choices big and small every single day.
From technical decisions framing the architecture, to validating new features, to prioritizing where to allocate limited resources first—faced with countless forks in the road, people strive to find the “safest and most perfect answer.”
However, as discussed in previous posts, a perfect environment where all variables are controlled does not exist in reality. No project can walk down every path in advance and inspect the outcome before taking action.
When analysis and meetings drag on in pursuit of the perfect choice, execution timing is missed, and team momentum weakens. The most dangerous moment on a project site is not when a “wrong decision” is made, but when fear of regret freezes everyone in place, unable to decide anything.
What Matters Is Not “Past Assumptions,” But “Present Response”
During retrospectives after a release or sprint, statements like these often arise:
“We shouldn’t have taken on all those requirements back then; we should have cut down to the core and deployed first.”
“When the schedule got tight, we should have discussed adjusting deadlines earlier.”
Clinging to assumptions like “If only we had made a different choice back then” in front of past events only exhausts the team.
If a decision was made based on the data and constraints available at that moment, it was likely the best judgment at the time. Just because unexpected issues arise or market reactions differ from expectations, there is no reason to blame past teammates or fall into self-reproach.
The truly vital question is not “Why did we do that then?” but “Based on the reality we face right now, how will we adjust our direction and move forward?”
The Power of Pivoting and Adapting
The world constantly changes, and no matter how meticulously we plan, unexpected events will inevitably occur.
Therefore, the strength of a high-performing team lies not in perfectly foreseeing the future from the start, but in the execution power to quickly pivot and flexibly adapt, letting go of unnecessary stubbornness or lingering regrets when plans collide with reality.
Even if things didn’t go as planned along our journey, if the lessons learned remain as the team’s core muscle, it is not a failure. We have gained the sturdiest asset to make better choices in the next sprint.
So That We May Smile Back at the Path We’ve Traveled
Just as Mia and Sebastian buried regrets about the untaken path, acknowledged each other’s choices, and smiled toward their respective journeys, we too cannot always pick flawless correct answers at the countless forks of work and life.
Since we cannot walk every road, all we can do is make the best decision given today’s conditions, calmly embrace the regrets and lessons met on that path, and take another step forward.
Are your feet currently tied, searching for a perfect answer at the crossroads of choice?
Rather than striving not to regret, focus on the choices before us today with a mindset to learn by doing. When looking back someday, that is the most genuine attitude to give ourselves a gentle smile despite any lingering regrets.