You watch these 15-second Tik Tok clips and influencers give you some shallow advice. Some say to double-down and focus on your strengths only; some say you should diversify and ‘taste’ as much as you can.

Black and white advice is bad because everyone’s situation is different.

  • Should an 18-year old decide what he’ll do for the rest of his life and “specialize”? I don’t think so.
  • Should a 58-year old man who’s suffered Shiny Object Syndrome keep looking to find his ‘passion’ for the next 20 years? I don’t think so.

Both types of advice is wrong. And they’re both right. I propose a hybrid solution.

Optimal Stopping Point

The secretary problem maps to life decisions. You’re trying to hire the best secretary. Once you fail them in your interview, you can’t hire them. Thus, from a stream of n candidates, how do you know when to stop? The algorithm to stop optimally is as follows:

  1. Always reject the first ne opportunities. e≈2.71828.
  2. Accept the first candidate you see thereafter that’s better than all the previous candidates. If no such candidate is found, accept the final candidate.

This yields the single best candidate about 37% of the time, regardless of n.

In practice: say there’s 100 different opportunities you want to try out (shiny object syndrome).

  1. Try out and “taste” the first 36-37 opportunities. (AKA going wide)
  2. Reject all of them.
  3. Accept the first opportunity that’s better than all previously seen opportunities. (AKA going deep).

Doing Even Better

One restriction of this problem is you can’t go back and hire a previously rejected secretary. In life, you’re free and no such restriction exists. So if you try out 100 things and nothing was better than opportunity #12, you don’t have to stick with the last opportunity. Just go with opportunity #12.

Caveat: you may not be able to try out, say, 100 business opportunities or strategies before going broke or running out of time. Thus, you may want to keep your list of n opportunities small enough to be practical.

For Multitaskers

Nothing restricts you from multi-tasking. The below method can work for those who want to try 2 things at the same time:

  1. Work on opportunity #1 and opportunity #2 (50% time on each) in parallel.
  2. Stick with the better of the two. (i.e. opportunity #1).
  3. Start work on the next opportunity. (i.e. 50% time opportunity #1 and 50% time opportunity #3).
  4. Repeat steps 1-3 until you’ve exhausted all n opportunities.

Downsides:

  • Each evaluation of an opportunity is twice as slow. This wastes time.
  • You must do all n opportunities. Stopping at the first best past ne will do better than single-tasking only 37% of the time. The other 63% of the time, you’ll reach the same conclusion but take twice as long.
  • n needs to be small enough such that you’re not spending a significant amount of your life exploring what to do.

Upsides:

  • When you’re done testing n opportunities, you’re doing the best opportunity.
  • It’s likely you’d have invested significant time in the best opportunity already. This saves time compared to the single tasking method about 63% of the time.

Thus, this method may work best for those who don’t have that many things they want to try out.

Life’s Not As Rigorous As A Math Equation

In reality, if you “taste” and try out different opportunities, you’ll discover your likes/dislikes and strengths/weaknesses very quickly.

Thus, a lot of opportunities can be skipped in practice and you don’t have to rigorously run through all n opportunities for your worst case.