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  • Brendan Stec

Hell Yeah! Or No.

“No one is really going to help you or give you direction. In fact, the odds are against you.”

– Robert Greene


One of the biggest challenges I face is navigating the near inundation of almost too many potential career paths. Articles on LinkedIn tout the latest job trends or best online courses or newest technologies. Friends tell me about their countless investment ideas, from buying rental properties to shorting tech stocks to owning "well-diversified index funds." It seems like everyone has a startup or project idea they'd want help with. It's hard to say no to any one of these ideas, especially since at least one of them is likely highly lucrative.

But I have to say no to most of these interesting opportunities. Because as Ray Dalio reminds us in Principles (1):

"You can have just about anything you want, but not everything you want."

With the help of platforms like AngelList, you can launch your own startup. With free courses on Udemy or Coursera, you can learn how to develop software. With some savings from your job, you can buy a rental property to start building equity in real estate. But can you do all of these at once? Probably not.

Inevitably, it becomes crucial for all of us to prioritize the opportunities that best suit our skills, interests, and values – to focus on a few goals that truly suit us best. While that decision is difficult to make, Derek Sivers (2) has a helpful heuristic to guide us in making that choice between paths:

“Hell yeah! Or no.”

Hell yeah!: This opportunity is incredible. This opportunity may not show up again. This is an opportunity I can’t afford not to do.

No: Any other opportunity. And be honest here. Opportunities that are “pretty cool” or “potentially interesting” don’t make the cut. Opportunities that are attractive merely for the money or status fall here too.

If we’re not honest about what we truly want – in our careers, relationships, or beyond – it can be hard to say no, which can overwhelm us, block us from fulfilling experiences, and even lead us down the wrong paths.

The later life of General Ulysses S. Grant is an excellent example (3). He finished the Civil War as a highly decorated and highly respected American general. But he still felt an urge to prove people wrong and pursue further glory – through opportunities that didn’t necessarily match his true values or talents. He pursued politics and ran a rather disastrous and corrupt Presidency from 1869 to 1877. Then, he lost almost his entire fortune in a fraudulent investment scheme. After so much accomplishment as a military leader, he died nearly penniless, both his spirit and reputation diminished.

What happened? Grant, like many of us, had trouble deciding what mattered to him. Urged on by an inflated ego, he couldn’t say no to bad opportunities, even ones in which he had no expertise or experience. He just couldn’t prioritize.

Hell yeah! Or no.

For when you feel tempted to accept that higher-paying job, for when you feel jealous of what someone else has, and think you might want it too, or for when you just have trouble being honest with yourself: think hell yeah! or no.

Because prioritization is a dilemma we all must eventually confront.



(1) Principles by Ray Dalio

(3) Ego is the Enemy by Ryan Holiday (pp. 114-116)

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