“Estimates are guesses. Deadlines are dreams. Shipping is truth.”
This brutal axiom cuts through the comfortable illusions that plague software development. It’s a wake-up call that forces us to confront the gap between our plans and reality.
The Estimation Game
We’ve all been there. A stakeholder asks, “How long will this take?” and we scramble to provide a number that feels reasonable. But let’s be honest—we’re essentially fortune-telling. We’re trying to predict the unpredictable, accounting for unknown unknowns while pretending we have crystal balls.
The best estimates are educated guesses informed by experience, but they’re still guesses. They crumble the moment we encounter that unexpected API limitation, that edge case nobody thought of, or that “simple” feature that turns into a three-week rabbit hole.
Deadline Fantasies
Deadlines often emerge from business needs rather than technical realities. They’re aspirational dates born from market pressures, conference schedules, or executive wishful thinking. While they serve a purpose in creating urgency and alignment, treating them as immutable laws of physics is a recipe for burnout and disappointment.
The healthiest teams understand that deadlines are targets, not contracts with the universe. They provide direction and motivation, but they shouldn’t dictate the quality of work or the well-being of the people building it.
The Reality of Shipping
When you finally push that deploy button, when real users interact with your creation, when your code runs in production—that’s when the rubber meets the road. Shipping transforms theoretical software into real value. It’s the moment when all the estimates, deadlines, and planning either prove their worth or reveal their flaws.
Shipping is the great teacher. It shows you what actually matters to users, what breaks under real load, and what features nobody actually uses. It’s unforgiving but honest feedback that no amount of planning can replicate.
Embracing the Truth
This doesn’t mean we should abandon estimates or deadlines entirely. Instead, we should hold them lightly. Use estimates as rough guides, not precise promises. Treat deadlines as helpful constraints that encourage focus, not sacred vows.
Most importantly, prioritize shipping regularly. The faster you can get feedback from real users, the faster you can course-correct. A working prototype in users’ hands is worth more than a perfect plan that never ships.
The truth isn’t always comfortable, but it’s liberating. When we stop pretending we can predict the future with precision, we can focus on what actually matters: building something valuable and getting it into the world.
Agile Ways 