Thoughts, Stories, Action Newsletter: Ponder new ideas, learn through stories, then walk the walk.

Fulfilling, Lucrative, Low-Risk. Pick two.

October 4, 2020
Jason Gutierrez


“Fulfilling, lucrative, low-risk. Pick two.” — Sahil Lavingia, Gumroad founder


The more I reflect on my life, the decisions I’ve made, and the ventures I’ve embarked on, the more I keep coming back to the conclusion that Sahil Lavingia is 100% correct.

When I worked as an engineer on a nuclear site, the job was steady (low-risk) and paid insanely well (lucrative); however, it didn’t bring me much joy (not very fulfilling).

Starting a coffee business has been insanely fulfilling, and with a near-limitless ceiling on earnings, quite lucrative. But it’s hardly been low-risk, as I’ve contributed a fair amount of my own money into jumpstarting the business.

Playing board games on a Friday night with friends is an extremely fulfilling, low-risk activity, but it certainly doesn’t put much money in the bank.

I believe there’s a time and place for any of the scenarios chosen, however that trade-off almost always exists.

For me, I try to keep a healthy balance in the activities that I choose, making sure that not TOO many of them are fulfilling and lucrative yet loaded with risk. By sprinkling in some low-risk category activities, I actually feel like I lower the overall risk across the board. But for certain, I’ve been focusing much more on the “fulfilling and lucrative” category as of late.

Being fairly young still, I like the idea of satisfying activities that fall in the high-risk, high-reward bucket. I’m sure as I age, that will likely fade. For now though, it seems like the way go.

A good friend of mine followed suit, launching a Kickstarter campaign for a board game he and his brother developed called “Pick’d Off” (which is actually a pretty damn fun game). Very fulfilling, potentially very lucrative, but for sure on the risky (not risque) side.

Life is full of trade-offs. The key, I believe, is to consciously understand the nature of your decisions and correct course whenever necessary.


What do you think?

  • Fulfilling and lucrative?
  • Fulfilling and low-risk?
  • Or lucrative and low-risk?

Pick one and run with it.



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