Conscious Bets & Investments – Manage upside, downside, and dividends

Pick a given goal, plan, project, or vision that has uncertain factors outside your control, such that you’re not sure if you’ll succeed even if you try hard.

Then consider these questions:

  • What do you think the odds of success are?
  • What resources are you investing in this goal/plan/project? (time, money, etc)
  • What will be the value if it succeeds?
  • If it doesn’t succeed…
    • is there an additional cost to this, beyond the resources you invested?
    • what are the dividends—what value will have already gotten? (learning, relationships, resources you can leverage into a different project etc)

Then consider:

Can you find someone to make the bet with you?
This is what Venture Capital is for the startup world, someone who bets their money on your company, and shares in both the upside and the downside.

Can you approach the goal in a way that increases the dividends?
This often takes the form of learning & relationship-building. Imagine what value someone might get out of a university degree even if they don’t graduate.

One way to ideate about this is to imagine that you from the future comes and says “you’ll quit this before you reach the end, but it’ll end up being totally worth it, so keep going”. What do you imagine you would do differently in the meantime?

Make sure that you consider ways in which changing your approach will also affect the odds of your success. If you decided to spend college just building relationships and learning about what’s interesting to you, you might not get as good grades. This could be totally worth it, depending on your context and what matters to you.


As usual, the coaches can help you think about all of these questions.