I suspect you’d like to make decisions you won’t regret. Right?

Especially since we make 35,000 decisions each day, according to various estimates, and most are unconscious. Most are trivial, but some are consequential; what to study, which career path to take, who to date or marry. 

The fact is, the quality of our decisions determines the quality of our lives. 

Yet, we receive almost no training in decision making. Most of us learn about decisions the hard way  — when we suffer the painful consequences of bad ones. I have plenty of experience in that!:

Years ago, I made the awful decision to drink and drive. I was drinking heavily at a tailgate and decided to get behind the wheel. You can guess what happened next: flashing lights, a breathalyzer, and handcuffs.

Thankfully, I didn’t hurt anyone, but the DUI was a crushing setback that pained me for years. I could have walked or hailed a ride, but impatience and carelessness got the best of me.

Later in my twenties, I almost got engaged to the wrong person because I ignored many red flags. To make a tough breakup worse, they then tried to steal money and valuables from me.

It took a long time to recover and start trusting people again. 

“Learn from the mistakes of others. You can’t live long enough to make them all yourself.” ― Eleanor Roosevelt

Yep, poor decisions waste your time and exhaust your emotions, causing needless headaches and heartaches.

Sometimes it’s best to learn things the ‘hard way,’ but Eleanor had it right – it’s often better to learn from others.

Or  best of all, follow a proven decision making system to make best possible choices for you. So without further ado, here are proven principles to make decisions that you won’t regret: 


Get to know yourself first if you want to make decisions you won’t regret

If you asked for my advice on whether to start a business or quit your job and travel the world, I couldn’t give you an answer.  First, I’d need to know your values.

How do you prioritize your health, relationships, need for creativity, growth, and contribution? For some, their physical health is #1. For others, it’s their relationships.

What is your minimum expectation in each vital area of your life? Are you willing to sacrifice one for another? Your values are the most crucial filter when making decisions you won’t regret.

Everyone has unique personal values, such as honesty or freedom. They can be anything if they’re consistent and virtuous. First, make a list of all your values, group them, and then rank them by importance

Once you know your values, you have the clarity of purpose to create your goals. Here is a simple system for Personal Development Goals that works. 

Prevent decision fatigue


A study found that justices were much more likely to grant parole before noon. The theory is that our energy levels affect our choices.

I see this often in my own life. I do my best writing and workouts in the mornings. My efforts are much worse at the end of a stressful workday.

Before a consequential decision, ask if you’re in a rested and clear-headed state—Time your most significant decisions during these peak states. Try to reduce the volume of decisions you make each day.

Consider that Steve Jobs, Mark Zuckerberg, and Barack Obama have been known to wear only a couple of outfits. I meal prep a few days in advance and automate as much as possible (bills, investments, re-orders.)

The less mental energy you spent on trivial decisions, the more you’ll have for major ones.  The most important realization is you don’t need to maximize value for every decision.

Your goal in routine decisions should be satisficing; to satisfy and suffice.  Finally, like an athlete before a big race, “taper off” before a big decision. Try to avoid having to make any big decisions back-to-back.

If you really want to make decision you won’t regret- be aware of biases

Several cognitive biases can reduce rationality. Know these subconscious influencing-factors, so they don’t cloud your objectivity.

For example, unconscious bias can occur when making a judgment about others. We are unaware of these implicit stereotypes, but they influence our decisions.

Confirmation bias is when we only seek information that confirms our predetermined perspective. It’s being in love with a solution from the start.  

The Monte Carlo fallacy believes that a random event is more likely if similar ones have occurred. It’s when the roulette player bets on a number because it appeared more than others.

Rosy retrospection is when we recall the past as being better than it was. When someone brings up the “good old days,” they may be neglecting the bad parts.

The point is: we all have cognitive biases, but by being aware of them, we limit their ability to cloud our judgment and help you to make decisions you won’t regret.

Skip past decision traps 

There’s plenty of decision traps. One is ‘overthinking it’ – assuming if the problem is hard, the solution must be complicated.

Whenever possible, favor simplicity over complexity. In the same vein, I prefer speed over perfection, especially if there is a first-mover advantage.

If failure isn’t fatal, it’s better to fail fast, so you gain the feedback you need to succeed.Another important point is don’t confuse relative value with absolute value.

Let’s say you are buying a new car, and the salesperson quotes some enormous savings from MSRP. She is inflating the relative cost to sway your decision. But your concern should be whether the car is worth the discounted price to you (the absolute value).

 Another trap is loss avoidance. This is when you focus on not losing something, resulting in missing a more significant gain.

An example is not investing in stocks because they could lose value, though they are likely to appreciate eventually. Focus on the net profit instead of avoiding losses.

Don’t get derailed by details

Ever seek out every piece of info available on the entire planet before deciding? This tendency is known as analysis paralysis. It’s when you get “derailed by details.”

It’s helpful to analyze the data and drill into historical, comparable decisions. But once you hit diminishing returns, you’re stalling. Admit that you can’t know everything beforehand.

So, don’t over analyze every possible scenario; focus on a couple of likely outcomes. Remove elements of the choice that are irrelevant or add noise.

Set boundaries, limits, deal-breakers, and requirements that cull the options. If the fear of failure paralyzes you, remember that sometimes you don’t even need to go all-in.

Often you can walk down a path to the point that it’s reversible. If you haven’t taken the first step because you think you still “don’t know enough,” the 40-70 rule can help.

Used by Colin Powell, this is the practice of deciding when you have at least 40% of the useful info.

Decision making tools 

Finally, let’s discuss a few tools for evaluating a decision.

There are tons of methods, so the critical question is: what is the simplest one for this use case?  Pros/Cons lists are popular, but it’s better to weigh each item by importance based on your values.

A helpful system goes by the pneumonic WRAP. Start by Widening your choices.

That is, don’t settle for the options you’re given; push for new and better ones. See how you can expand your set of choices. Then, Reality-test your assumptions.

Exit your head and reason some counter-arguments to your line of thinking. Next, Attain some distance before deciding.

Step back and distance from your emotions. Ask a caring friend or an impartial expert for advice. Finally, Prepare to be wrong. Think about what insurance or plan-b you have if things go south. 

Another useful technique to make decisions you won’t regret is called Six Hats. Pretend to put on each of the colored hats and act out its perspective. The white hat is the detective that scours all the evidence/data. T

he Red Hat uses intuition and emotions. Tap into your gut and ask: what do I feel I should do?

The black hat is the naysayer, the pessimist. Ask what could go wrong in the worst-case scenario?

The yellow hat looks at things as an optimist. How would the most favorable outcome look?

The green hat is the right-brained creative that imagines outside of the box.

Finally, the blue hat sums up everything you’ve learned from the other five hats.

Of course, there are many other decision methods.

What’s most important is that you find one that works best for you and be consistent with it. If nothing else works, reflect on your values from earlier. Which options align with your world view? Which ones help you get to where you want to go in life?

Ask yourself: if I made this decision, how might it affect me in the future, whether it’s ten months or ten years from now?  

Most importantly, commit to your decision. If you go back-and-forth and waiver, you didn’t decide at all, and the burden is still there. Settle on a decision, be proud of your made one, and don’t ever have any regrets. 


Chris is an accomplished sales and business development leader with experience at companies like Microsoft, Salesforce, and Dropbox. He went from being kicked out of high school twice to earning an MBA at UC Berkeley, and from being a pack-a-day smoker and aquaphobe to marathoner and triathlete. He writes about self improvement for knowyourbest.com


  1. Very helpful tools for decision making. I’m definitely guilty of rosy retrospection. I’ve actually in the middle of reflecting on that and why I don’t see certain things through a more realistic lens. Just knowing that rosy retrospection is a thing, helps me step away from it a bit more.

    • I have to say I rather like rosy introspection. I think there’s two sides to everything…and maybe being a bit in the middle works too.

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