The Maybe Problem

Everyone talks about the importance of saying no, but that’s not where the real challenge sits. Saying no to something clearly misaligned is relatively straightforward. The harder decisions are the ones that aren’t clear. The maybes.

Most opportunities land in three buckets: a clear no, a clear yes, and a middle ground where something is interesting, credible, and just compelling enough to consider. That middle ground is where things start to accumulate. Maybes are rarely bad ideas. They’re often good opportunities, from people you respect, in areas you care about. The upside is easy to see. The cumulative impact is much harder to spot in the moment.

Because not all yeses deserve to be yeses. Some should have stayed as maybes, and a number of them, with a bit more distance, would have been better as nos.

What also becomes apparent over time is that the “yes” bucket doesn’t just fill up with choice. It fills up with responsibility and obligation. Roles, commitments, expectations, things that sit firmly in the category of “this matters and needs to be done”. That part isn’t particularly interesting or energising to talk about, but it’s real. Not every yes is optional, which makes being deliberate about the discretionary ones even more important.

The tension sits in that combination. A natural pull toward variety and new opportunities, layered on top of an already full base of responsibility. Without discipline, the result isn’t failure, it’s dilution.

That dilution shows up in predictable ways. Writing gets pushed out, even when it’s something genuinely enjoyed. A book like Careering gets close to the finish line but stalls. A venture like Holdmine moves forward, but without the focus required to realise its potential. None of it is about capability. It’s about spreading time and energy too thinly.

There’s also a human element that makes this harder. Saying no to a maybe often means saying no to someone who has thought of you specifically and brought you something with genuine intent. Even when nothing has been promised, it can feel like letting someone down, and that’s often enough to tip a maybe into a yes.

One idea that cuts through this comes from Derek Sivers: if it’s not a clear “hell yes”, treat it as a no. It’s deliberately extreme, but it raises the bar for what earns a commitment. Alongside that, the thinking from Essentialism reinforces the same principle: focus on the vital few, not the trivial many.

The shift now is less about understanding these ideas and more about applying them with the focus now on refining down what actually matters and being far more deliberate about where time and energy go. Creating space for reading, thinking, and proper rest doesn’t happen by default. Because the cost of getting this wrong isn’t failure. It’s a lack of space. It’s a lack of connection and purpose with the people and work that matter most. And that’s no longer a trade worth making.

P.S. Knowing and doing are two different things – wish me luck!  

 

 

Quick references

  • Essentialism: Focus on the vital few and eliminate the trivial many. If it’s not essential, it shouldn’t be taking your time or energy.
  • Hell Yeah or No: If something isn’t a clear, full-bodied yes, treat it as a no to protect your time and attention.

Further reading