Portfolio of initiatives

Secret Weapon #012

28 May 2025

Planning and executing on lots of different activities in parallel can be a big headache. It’s easy to unintentionally end up with too much to manage on some fronts, and simultaneously be underinvested on others (particularly if you are someone with a bias for action!).

A simple technique for anticipating and mitigating this is to map everything out. Even if each individual activity on your to-do list makes sense in isolation, the important thing is that they sit together as a coherent portfolio of work.

To get started, think about each activity on three separate dimensions:

• The time horizon for getting it done
• The level of familiarity or certainty you attach to it
• The anticipated size of the prize

Once you’ve mapped your portfolio you can give it a quick sense check:

• Do you have the right balance of quick wins vs. long-term impact?
• Does the degree of (un)familiarity match your risk tolerance?
• Have you got enough bandwidth to run everything in parallel?

A balanced portfolio will typically include a range of activities that pay off over different time horizons, with greater clarity around near-term deliverables and more uncertainty about how long-term initiatives will play out.

It’s not a hard-and-fast rule though – every situation is different, and sometimes a risky short-term bet or predictable long-term effort will make sense. The point is to be intentional about what you take on, thus maximising your chances of success.