Time planning is a paradox. We want to be ambitious, yet we know that delays will occur. Even if we try to do things on time, we usually fail. Why?

Whenever people jump into a new mission or start working on a new task, analyzing the time plan is often skipped, citing a lack of time. What an irony.

During execution, people are often surprised that everything takes longer than anticipated or that the environment changes faster than they assumed. Yet another irony.

And sometimes, you’re just unlucky with the timing. You have the best product in the market, but the market is not ready for your product yet. You have that new feature on the product roadmap, but it’s shipped too late to avoid an unhappy customer from churning. You’re in the middle of negotiating a game-changing distribution partnership, but it tanks on the last mile because your partner undergoes an M&A transaction.

I have real-life experience with each of those cases from my 10 years at the helm of Yonder, a B2B SaaS company I co-founded. Even if you try, you can’t fully control the timing of how things unfold in entrepreneurial life.

Why? Let’s look into some conceptual aspects.

1. Everything Takes Longer Than Expected

Farmers know you can’t grow a tree in a year. Farmers also know that developing a tree takes many setbacks — dry years, thunderstorms, pests.

For some reason, many entrepreneurs, inspired by all those unicorn stories on social media forgot the logic of down-to-earth farmers.

Starting and growing a company is like starting a fire with green wood in pouring rain. No matter how ambitious you are, it will take time before you have a nice fire in the pouring rain.

More conceptually, success and failure often depend on correctly or incorrectly assessing your own speed and capabilities versus the speed and capabilities of your business partners and competitors.

The best examples of this phenomenon I can think of are project delays or botched M&A transactions.

2. The Situation Changes Quicker Than Anticipated

Funny enough, although everything takes longer than expected, the situation can change more quickly and abruptly than anticipated.

No matter how many project briefs you prepared, if the situation or the environment has changed, they’re worthless. And you can’t produce new project briefs at the same speed as the situation or the environment changes.

The best examples of this phenomenon are climate change or the rise of artificial intelligence. Both of them started slowly and then suddenly accelerated. That’s when people get sweaty palms and start hyperventilating, because they realize that their plans were overtaken by the new reality.

3. Dependencies Derail Progress

Humans tend to come up with overly complicated solutions. Especially in tech, people still think they need to prove their skills by designing an extra complex solution — even though everybody knows this will end in dependency hell. Simple is beautiful, but people often forget that.

Now that you have started your super complex project, everything looks great in the beginning. Problems and dependencies only surface at the end of the project. And the more complex a project, the higher the number of problems and dependencies popping up seemingly out of nowhere shortly before touchdown.

What can you do? Stick with an old, boring principle: A good solution now is better than a perfect solution too late.

If you stick with this principle, your solutions will automatically become less complex and thus less vulnerable to dependencies.

4. The Schedule Fallacy

Even though people love complex solutions, they always start with the simplest task. This creates the illusion of being on schedule, but it hides the fact that the complex tasks will take longer to complete than the simple tasks. If you spend time on the simple tasks at the beginning of a project, you won’t have time to synchronize and discuss the complex tasks with your colleagues, leading to a suboptimal solution, a delay, or even a botched project. That’s why you should always start with the hardest task to stay on schedule.

Another fallacy is that we tend to overestimate our abilities and underestimate our tasks. This often leads us to announce a very ambitious schedule, only to be surprised by (self-inflicted) delays.

Conclusion

Time planning is a paradox. We want to be ambitious, yet we know that delays will occur.

We think we can fix delays by planning time reserves, but that’s often an illusion: We kill the time reserves by starting on irrelevant, simple tasks rather than tackling the complex tasks first.

Why is time planning so difficult when the concepts would be so simple? It’s because imperfect human beings do it rather than a machine.