What if I Never Risk it All?

Question: I’m thinking about what I don’t want to regret in life and there’s one thing that keeps popping up. I’ve always been cautious. I’ve never risked it all. Should I give myself permission to just go for it? Or is that really being selfish or childish?

Paul Sutherland: Such an interesting question you ask. It seems anchored in not wanting to “experience regret,” that silly phrase that pops up on talk shows where the pop psychologists advise you to give yourself permission to not answer the phone, not do the laundry, or not bother with a friend’s greedy/needy nature. But let’s first talk about risk, which is an area I know well because my job as an investment manager is really about risk management.

Risk exists in the future and risk is about chance. When you say, “risk it all,” it sounds like you want to do something life threatening, like fighting off gorilla poachers. That’s an ultimate kind of choice that I won’t talk about directly. But If you are thinking of risking your financial health, then it is just a cost/benefit analysis: looking at the worst that could happen and “kissing it.”

What do you wish to get for your risk? Happiness seems the only real thing worth risking it all for. If you’re not already happy, then I suspect you will not find happiness by taking a loan out on your home for some wild investment scheme. If you ended up homeless and in debt, but felt satisfied that you went for it, would that benefit be worth more than the pain of doing nothing and regretting not acting on your risk-it-all scheme? That’s the question I would contemplate. Notice that I did not use the word “fail.” Not going for something because you fear failure is letting your ego rule you. If your ego rules you, no matter what you risk, you will never fill your “hungry ghost.”

I think perhaps you really have a larger question to ask yourself. First, I think you should learn to meditate and acquire friends who are happy. Then you should ask yourself what you really want in life. My straight answer to that question would be “To start living a spiritual life!”

Now let’s play with what that means.

I am currently living in Uganda, a place where people introduce themselves and then typically ask, “Are you a Christian?” or “Are you a Believer?”

“What does that mean?” I answer.

“That means you believe in Jesus!”

So I ask, “If I followed you around all day and watched how you spend your time and your shillings, would I be able to tell what a Christian is?” Sometimes the conversation stops right there. Or we may talk about something safer. But occasionally the conversation turns to spirituality.

To me, spirituality is about responsibility. Spirituality is about being intentional about our behaviors to do no harm and to help. It is about knowing that life is interconnected and being one with everything—especially with this moment and the situation you and those around you are in. Being rooted in the moment allows us to get beyond professed beliefs and opinions— which are mostly worthless—and to accept the reality and truth of that moment.

As the Bible tells us, “The truth will set you free.”

To touch reality is painful. It is to “kiss the ugly” in ourselves and others without judgment about whether it is good or bad. In Buddhism it is about what is the right behavior based on the current situation without attachment to the outcome. So if a kid is sick, help! Don’t say there are another 1,000,000 such AIDS children. Help the one you’re with.

I think the biggest risk one can take in life is declaring to ourselves that we will live a spiritual life. Living a spiritual life allows us to live unencumbered by our opinions and our desire to be accepted by others. We lose the safety net of friends, books, beliefs, and mental habits that allow us to avoid real “risks.”

The real risk is in accepting the fact that we control our actions and responses to events. We are 100 percent responsible for our response or nonresponse to each moment. As you sow, so shall you reap. So give yourself permission to go for it. Go for a spiritual life. And if you’re living a spiritual life, anyone who follows you around will know what that is.