When I was at a tech event in San Francisco recently, a CEO was asked how they thought about balancing new initiatives with the core business, and their answer was simple but broadly applicable to life.
It struck me as particularly the type of advice one can only learn from experience.
Balancing an organization
All teams across an organization need resources. Most teams don’t have enough people for the goals they set out to achieve, and without these resources, some projects will fail. If your success has stemmed from a unique strategy that continues to win, how can you justify peeling useful resources away from it, and dooming it to a larger probability of failure in the name of new, unvalidated initiatives?
You can imagine there are a bunch of “good” answers: analyzing opportunity-cost, finding new markets with higher growth rates, cultivating higher margin revenue streams, etc.
But the reality was more simple than analytical.
Sometimes, the organization is doing too many things. When this is true, the product will often stagnate, sales people will report more losing deals, and teams will slow down. You will start to lose too many battles. This is obvious when it is starting to happen, and most in the organization — especially leadership — will have the strong, innate urge to focus resources. People don’t like to lose.
On the flip side, sometimes the organization isn’t doing enough things, and the larger, cash-cow teams will grow and grow until you see folks working on things that clearly aren’t critical — they will become the metaphorical “cog in the machine,” spinning because they’re supposed to, but going nowhere. In this scenario, especially in the technology industry, innovators in the company — especially leadership — will have the strong, innate urge to launch more impactful projects.
There is no necessary deeper analysis. Instead, the organization — while it’s growing — is naturally bouncing back and forth between two feelings. And these feelings tend to be obvious, as long as people are honest with themselves and their teammates. Thus, striking a balance is about being aware of your feelings and the feelings of those around you. 
And if no one feels strongly either way, then you’re probably sufficiently balanced.
Now that I’ve been thinking about this idea for a while, I think this approach is applicable to self-management as well.
As we stumble around our life journeys, we often fail over and over again. Eventually, once we find something we’re kinda good at, we cling to it and it becomes a part of our routine & identity. Although continuous practice is a key to success, people often go overboard: they stick to what they find comfortable and close themselves off from new, potentially risky experiences. Discovering new skills, friendships, and responsibilities requires us to sacrifice our successful routines and identities in the face of likely discomfort.
So how can we think about balancing our existing “successful” routines with new experiences?
A common analytical approach in life coaching is to leverage the “Wheel of Life”. With it, you rank your life in several various categories, and then create action plans to try new things in the areas you are weak. This works to an extent, but the method has many gaps . Answering the question “should I try more things?” might be easier with an emotional approach.
When people are trying too many things, they bounce around frantically, lose focus, and rarely make progress on bigger tasks/goals. So ask yourself: How do you feel about your progress as of late, and is that progress meaningful to your desired identity?
Conversely, when people don’t try enough new things, their chances of finding their innate passions, talents, and interests plummet. So ask yourself: How passionate do you feel, and how much have you discovered about yourself lately?
There is no necessary deeper analysis; you just have to be aware of your feelings. If you aren’t passionate (with or without progress), expose yourself to new experiences. If you are passionate, but feel as though you’re not making good progress, try fewer things and focus on that which is most important.
If you’re both passionate and making progress, congratulations, you’ve probably found your balance!
 This has cultural implications. It’s a lot easier to balance an honest organization than one where people either ignore problems, or perceive everything as urgent.
 The Wheel of Life doesn’t account for identity, talents, or interests. The metrics only exist to force you to judge yourself relativistically.