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By Jon Westenberg

I’ve been making some tough decisions lately  —  so has my partner. We’re both entrepreneurial, we’re both set on careers that focus on startups and technology. We’re both struggling with career choices that will define the next few years of our lives.

When we sat down to talk it out, the first thing we were asking ourselves, was how do we know if we’re making the right decision? How do we know if we’re making the right call?

And of course, the answer comes right back  —  we fucking don’t. We have no idea whether we’re making the right decision, in the long term, or not. Neither of us can see the future, neither of us know how it’s all going to pan out. Neither of us know if it’ll all end in disaster.

But the more we talked about it, the more we started thinking down a different route. We’d been set on trying to divine where our lives would go if we made a call, one way or another, when that really wasn’t the point.

What we should have been asking ourselves, is whether the choice would make us happy. Simple as that.

That’s a much better way to frame the decision. We know what does and doesn’t make us happy, in our careers and our lives. We know that projects and jobs that prevent us from sitting down together for dinner at the end of the day don’t make us happy.

We know that having to work on weekends, when we should be recharging and getting our personal lives and affairs in order, leaves us feeling miserable and drained throughout the week.

We know a lot about what elements of our lives are positive and negative  —  after all, that’s the easiest data you can ever gather about yourself  —  and we know which decision will provide for those elements.

In the end, because it’s impossible to see the future, it’s pointless to worry about whether or not we’ve made the right decision. All we can ask ourselves, is whether we’ve chosen something we’re happy with.

The best decisions in my life have always been the ones where I’ve unconsciously chosen happiness over the so-called “right way.”

I dropped out of law school because it didn’t make me happy. That’s one of the best choices in my life, because it reset where I was going, and it gave me a chance to think clearly about who, where, and what I was going to be.

And the whole reason I’d gone to law school in the first place was because I thought it was the right thing to do, for the right career. Nothing to do with whether or not I wanted to study law.

Albert Schweizer said:

“Success is not the key to happiness. Happiness is the key to success. If you love what you are doing, you will be successful.”

I might not make the right decisions for my career, if I do what makes me happy. I might turn down some big opportunities, with some big money. But those big opportunities aren’t the only measure of success.

When I get where I’m going, when I’m six feet under, a life time of putting up with someone else’s shit in order to reach some metric of success that’s based on purchasing power and a job title isn’t going to matter. A life time of being happy won’t matter either  —  but I’ll have enjoyed it a lot more. 

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