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How to start making big life decisions without regret in 3 simple steps

How to start making big life decisions without regret in 3 simple steps
Renee Osaigbovo
April 15, 2020
“You could do everything wrong for the next 10 years of your life and be young as f*ck.” - Gary Vaynerchuk

When was the last time you regretted a decision that you were once really excited about? Or made a decision and thought of all the things you could do when it doesn’t work, instead of what you will do once it does?

Our society is built on restrictive guidelines. Guidelines that tell us to make lifelong decisions before we hit our 20s.That create stigma around changing your major.That tell us that the best life experiences are linear and predictable. 

For example, you graduate high school, then go to university. You graduate and then start working. You find someone, get married, trade in your bachelor pad and hot rod for a white picket fence and a minivan. 

If you’re a woman, you should ideally stop working and raise the family for a few years, if not the rest of your life. 

If you’re a man, nothing really changes, you continue to work like normal. 

You work a 9-5, you hate your job, but you know you have to work long enough to make it to retirement age. 

You retire, start doing the things you want to do, and then you die.

This is the American dream.

And it’s not a bad dream. It’s just that. A dream. 

There are so many other possibilities that are out there for us to explore, but for the majority of people who dare to explore, they let this cloud of regret stain every choice.

Say you’ve graduated university, and one day you’re at a stop light. You get a text inviting you to go on a commune. You’ve always wanted to go on a commune, but never got the chance to. You decide to click the link, and register. You leave in 30 days. You wrap up your open bills, say your goodbyes, and head off.

While there, you meet the love of your life and move to a farm in Bulgaria to raise goats with them. You always have enough to live comfortably and save, you visit your family for all major holidays, and you have children that love you. You live until you’re 83 and die happy.

All of this happened because you took that random chance, deviated from the set path, and clicked on a link. You made a life decision without regret and got to live a full and happy existence. 

Let’s try a different reality.

Say you’ve graduated university, and one day you’re at a stop light. You get a text inviting you to go on a commune. You’ve always wanted to go on a commune, but never got the chance to. You think about what people would say about you: “Wow, they just graduated with a computer science degree and decide to do that? What a freak.” You think about the look on your mother’s face when she blames herself for your choices. You think about the 20 jobs you just applied to last week that could call you with a job, you never know.

You delete the text and walk into the street. You’re hit by a car and die. You were only 22.

Every choice is a 50/50. Things could go amazing, and life could open up to you. But things could also go really wrong, and cut your time on this earth short. You could have easily flipped the endings on those two scenarios if you wanted. Anything could have happened.

What’s the real difference between the 2 scenarios? On one hand, you saw an opportunity to do something you really wanted to do, and with a joy filled heart, went forward and made a decision that made you happy.

On the other hand, you saw an opportunity to do something you really wanted to do, and talked yourself down immediately. But hey, at least you didn’t disappoint anyone.

Why do we do this to ourselves? 

Because we spend too much time thinking about how others want us to live instead of us making choices that make us happy.

There are some decisions that are hard to make, and make us feel bad when we make them. But this doesn’t have to be the story with every decision. Here are 3 simple steps you can take to start making decisions that are free from regret:

1. Spend maximum 1 hour when deliberating on a choice: 

We make roughly 35,000 decisions a day, 227 of them on food alone1 according to researchers at Cornell University. Our brains make decisions up to 10 seconds2 before we consciously realize it. Whenever we pose a question to ourselves, we know what we think is right before it is even formulated as a thought in our minds.

But what do we normally do? We pose a question, have the answer, then we sit on it for weeks, months, and sometimes even years. Sometimes the answer is an immediate no, but we try to find a reason to say yes because we feel we’re letting people down. Or the answer is a yes, but it’s a yes that scares you, so you spend years thinking of everything that could go wrong even though you know deep down that you’re ready for the challenge.

The next time you have an important decision to make, give yourself a time cap of 1 hour. Make this your new decision making process. 1 hour to do all of the research you feel needs to be done in order to make the decision confidently. With the world at our fingertips, it’s so much easier to learn what we think we need to know to make the right choice. Once the hour is done, commit to something consciously, and stop thinking about it.

2. Stop focusing on your plan B,C,D, etc:

Whenever we create a plan B, it’s normally because we think the plan A is going to fail in some capacity. Then when it fails, we are regret free and say things like “Oh well, I knew that was going to go wrong anyway”. It’s a self fulfilling prophecy. Compare the way you act when you think there is only one way out of a burning house. We know that we can’t just accept failure, and fight until the end to get out of that one exit. We exceed our expectations. 

Whatever your next decision is, make only one. Don’t create a fail safe. If you fail, so what. You are more than capable of creating a new Plan A and devoting yourself 100% to making that work. Try this at first with smaller decisions, and start working your way up to those decisions that you’ve been sitting on for years. Treat this as a muscle that can be strengthened.

3. Write your hero story:

A hero story is a future forecast. It’s what you want to feel, what you want people to say about you once your idea pays off. Most importantly, it puts you in the driver seat of all of your choices. 

For some, it’s scary to be 100% accountable for the decisions you make. But once you’re accountable, you’re responsible. The failure/success of your decision is your own. And when you decide to control your destiny, you can start making decisions with confidence more often, because you are in control of the future narrative.

You can write a 10 page manifesto, or make a tough decision and think to yourself “This is going to work, I am successful, and I am more than happy with the choices I’ve made”. 

Becoming your own cheerleader instead of waiting for other people to affirm your decisions instills confidence in yourself that you can, and will, come out on the other side successful.

In summary, go and take that course that’s outside of your degree plan. Date that guy who your friends don’t think is “cute enough” but makes you feel special. Take that trip. Save for that smart watch that you think will elevate your day to day routine. 

At the end of the day, you are a capable adult who can make decisions on your own. If you don’t feel you are, start learning more and pursue knowledge every day to become someone you trust more than anyone else.

Or, don’t.

The choice is always yours.

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