How to Be Smart About Big Decisions

It’s normal to fear big decisions after the age of sixty.

We’re more risk-averse. Afraid of unintentional outcomes lurking around corners. With less time ahead of us to correct mistakes.

It’s easier to play it safe. Maintain the status quo.

But big decisions are unavoidable. They don’t decide themselves. And we can do damage by procrastinating or ignoring the inevitable.

Philosopher, Ruth Chang, thinks we’ve misunderstood hard choices.

In her TED talk, How To Make Hard Choices, viewed more than 7 million times, Chang says we often choose the safest option because we don’t feel smart enough to qualitatively know which option is better.

She then assures us that hard choices are hard specifically because there is no best option.

So what steps can we employ to be more fearless when approaching a touch choice?

Jane Fonda, Socrates, and Kierkegaard

This unlikely threesome has advice that can shed light on how to use the past as a guide for making decisions.

Jane Fonda, who publicly vetted her decisions over the course of an extraordinary life, tells us this:

“You don’t learn from successes, awards or celebrity. You learn only from wounds, scars, mistakes, and failures.”

In other words, it’s about how we integrate into our lives, learnings gained from failure.

Centuries earlier, the philosopher, Socrates, recognized the concept of learning from the past.

When the state legally threatened to halt his then controversial quest for insight and knowledge, he famously said: “An unexamined life is not worth living.”

And philosopher, theologian, Soren Kierkegaard, spent a career teaching that, “Life can only be understood backwards, but it must be lived forwards.

It’s recognized as truth that much can be gained by examining our past. And in important ways, entrusting our future to it.

Within Reason, Hinge Big Decisions on Past Experiences

Here’s what comes in the way of making big decisions.

Instead of using the past to support our choices, we use it instead to recall our failures. Which leads to avoidance. Because humans have a propensity to shy away from throwing a spotlight on painful experiences.

Power of Positivity’s article, The Only Five Reasons You Should Look Back on Life, states, “While we don’t want you to get stuck in a past traumatic event, you can actually use the darkness to create the brightest light.”

In business, we take whole-cloth, the idea that lessons learned from the past can increase current effectiveness and efficiency.

Then why run away from past experience to support our personal lives?

A Simple Process That Can Help

Write down a clear assessment of your current issue, then use probing questions like these to gain greater understanding:

  • How have I decided on similar issues in the past?
  • What were the positive and negative impacts of those decisions?
  • Which decisions were rational and productive?
  • Which decisions were emotional and non-productive?

Move through the exercise as quickly as possible.

Try not to relive the actual experience. The job at hand is to recognize the learnings, not judge the outcomes.

Adding Future-State to the Decision Equation

As a checkpoint against failure, ask yourself these questions as an insurance policy.

  • Six months from now I will consider my decision successful if the following is true:
  • One year from now I will consider my decision successful if the following is true:
  • Five years from now I will consider my decision successful if the following is true:

We can improve our chances of success by spreading the focus and control of our plans over a longer period of time. It’s foolhardy to think life-altering issues get resolved in the short-term, or all at once.

Allowing for observation over time can jog us back on track in an unforced way. Course-corrections can be made. But only if we have a strong plan to begin with.

Vote for Well-Being, Not Senseless Action

Keep in mind, not every decision is a decision to move forward! Sometimes NO action is better than positioning action as a default.

Writer/editor, Jory MacKay, has timeless advice for making tough choices in his article for Zapier, How To Make Difficult Decisions. He advises we take a deep breath before taking action. Time can give us space to think before we respond to stimulus in a way that might ultimately prove harmful.

Another rudder to submerge into the often rough waters of decision-making is to hold close to your best-held values.

You’ve spent the better part of your life developing a sense of self and well-being that feels right for you.

As Ruth Chang is fond of saying, “Tough decisions are not made by reasons given to us, but supported by reasons created by us.”

2 thoughts on “How to Be Smart About Big Decisions

  1. Very interesting ideas. It’s so hard to trust your gut in these situations even though it’s our best compass for moving forward.

    1. True. It’s easy to second-guess ourselves. But that’s always spelled trouble for me!

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