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Clubhouse summaries: @shl and @jasonfried discuss deadlines

This is a summary of a Clubhouse conversation between several people, but predominantly @shl from Gumroad and @jasonfried from Basecamp.

⏰ Are deadlines good or bad?

The conversation started as a debate.

  • 🚫 No deadlines: Gumroad has no deadlines; people simply take work that looks fun from a queue.
  • Deadlines: Basecamp uses deadlines not to put pressure on people but to be explicit about what their "appetite" is for any given project.

Conclusion: Both agreed that there's no "One True System". Many systems can work for you – pick one that you like and use it.

Why are deadlines bad? 🙁

Both founders agreed that deadlines are

  • Wrong – People are bad at estimating how long things take.
  • Stressful – People often experience high stress because of deadlines.

Work expands but timelines remain fixed. This means that deadlines are nearly always stressful – you can think of them as a suitcase that a traveller is trying to shove more and more luggage into until the seams start to split.

Why are deadlines good? 😁

Because estimating is hard, you might spend far longer on a project than is worthwhile. It's useful to think of projects as bets – you don't know how much value they will provide or if you will finish them in a reasonable time.

If you go to a casino, you should usually assign yourself a fixed amount of money. If you're using cash, you might draw $1000 and commit to leaving if it runs out to limit your downside risk.

Similarly, deadlines can limit the downside risk that comes from the unknowns in any project. While most companies will try to push harder to get something across the line as a deadline looms, Basecamp rather aggresively cuts scope to fit a given project into an agreed time frame.

If the project isn't completed by the deadline, instead of adding more time by default as many other companies do, the default outcome is to drop the project and regard the best as "lost". In some cases, a new deadline is assigned (e.g. if more information is uncovered during the allocated time that makes it clear exactly how much more time is needed and what value can be gained), but this is an explicit choice, not the default.

How can you stop deadlines causing stress? 🥴

The main reason to avoid deadlines is the stress that they cause. Basecamp doesn't associate projects with a pile of work. A "project" is only the goal or concept, and the team working on the project figures out what can be done in the allocated time – not how to get through all the assigned work by the given deadline.

You can think of this as giving your team a "scope hammer". They can smash things up as necessary to fit tasks into the timeline. Every project has a "two week version" and "one year version" – once you've decided your risk appetite for a specific goal, you can carve up or throw out tasks as necessary to fit.

Deadlines avoid sunken cost fallacy 🌊

If you estimate that something will take you three months, you might find after nine months that you still haven't shipped it. At this point, you've sunk so much time into it that you will default to spending "just one more month" on the project. This is bad and a clear case of the sunken cost fallacy, a strong human bias that is irrational.

By having strict deadlines, you can avoid this. If a project isn't working out, something is wrong. Rather understand what is wrong and go back to the drawing board for a while, instead of pounding your head against a concrete wall that won't budge and will cause you pain.

Does this work for everything? 💊

No. Some things just have to be done. Both founders agreed strongly on this. You can't not file your tax return by the assigned date, even if you underestimated how big a task it was (Basecamp) or it isn't fun (Gumroad).

Similarly, for security incidents, severe incidents that cause data loss, or other crises, you simply can't put off dealing with the task at hand.

Does this also work for larger corporations? 🏙

Maybe. A place like Microsoft is not going to change over night, but some large corporations are adopting similar systems and they seem to be working.

An interesting side note is that startups often try to act more like big companies – adding more process and more formality, emulating what they see at corporations.

In reality, corporations wish they could be more like startups. There is so much value in flexibility, giving your customers what they want and following your gut. Big companies would love to be able to operate like this, but they can't. Enjoy it while it lasts!