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5 Ways to Make Better Decisions in Your 20s

It’s the difference between starting a life in your 30s or having a life in your 30s

Photo: Ben White/Unsplash

In your 20s, you are barraged with an endless number of choices and decisions:

Where should I study?

What should I study?

What career should I have?

Who should I marry?

Where should I live?

That’s a lot of shoulds, and potentially a lot of disappointment.

These are essentially life’s biggest questions you have to attempt to answer before the age of 30. What you decide can shape your life for the next decade or more, often with significant financial and social costs if you get it wrong.

What you do in your 20s and who you do it with will have a disproportionate influence on the adult life you will lead. It can be the difference between starting a life in your 30s or having a life in your 30s.

You can feel like it is impossible to make any sort of decision without feeling some level of buyer’s remorse or Fear of Missing Out (FOMO). The uncertainty is cripplingly sprinkled with feelings of anxiety and a side of constant doubt.

Add in high parental expectations, imposter syndrome and the incessant competition of social media comparison and you’ve got the perfect recipe for poor mental health.

The importance of decision making

Needless to say, making decisions in your 20s can be overwhelming. No generation has had this much freedom of choice. But no generation has also experienced this much uncertainty and anxiety.

At my age (25), my parents were already married, moved to another country and settled down in suburbia with kids. Life was simpler, potentially more boring but at least certain.

You knew your role in society and what you had to do.

This is not a judgment, only an observation from seeing my parent's life unfold before my eyes. I don’t think it was right or wrong. It just is.

Faced with these big decisions, you may decide not to choose. That keeping your options open now will allow you to capitalize on the perfect opportunity later.

But it doesn’t work that way.

Not making choices in your 20s is a choice. And making a choice later also does not automatically make that choice better. Indecision could in fact create fewer choices in the future.

You might be able to kick the can down the road for now. But you might get to a point where there is no more road and the can is gone. You’ve missed the golden opportunity to set the right foundations in your 20s.

Commit to something early. Even if it is volunteering or a crap job. You can always revise and change course. Nothing in life is set in stone.

You might think that this is wasted time or you are starting from scratch again. But what you are really doing is building life capital and starting from experience.

Tools to help, you make better decisions

The quality of your decisions determines the quality of your life. And what determines the quality of your decisions is the quality of your mind.

Here are some tools I’ve used to help me make better decisions. I’ve drawn heavily from Annie Duke’s book, Thinking in Bets: Making Smarter Decisions When You Don’t Have All The Facts.

1. Backcasting: Working backward from a positive future

In your 20s, envisioning the future can be difficult to downright impossible. You are faced with so much uncertainty how are you meant to think beyond where you will live in a couple of months?

But when it comes to advanced thinking, standing at the end and looking backward is much more effective than looking forward from the beginning.

What if you picture yourself at the age of 35? Where do you want to be? What do you want to be doing? How about at 45 or 55?

Write the thoughts that come out. Maybe a family? A stable career? How many countries do you want to have visited?

Imagining a positive and successful future can help you understand the steps you can take today to put you on that path tomorrow. It can help give purpose to your daily actions and provide a north star.

2. Pre-mortems: Working backward from a negative future

We all know what post-mortems are: an examination of the cause of death.

Why not go through this exercise before anything goes wrong? List all the things you think could possibly go wrong. No matter how silly they are.

Once you’ve got a range of possibilities, assign each one with a probability. Each scenario should fall between 0% — 100%. But no one possibility should be either 0% or 100%. Nothing in life is guaranteed, no matter how certain they may seem.

This exercise can help you anticipate what might potentially go wrong and mitigate the impact and temper expectations.

3. Experiments

Conducting small-scale, low-risk experiments are a fantastic way to try new things. You can get the learning from the experience without the fear of failure or commitment.

It is like test-driving a new car or going on a few dates with someone interesting. No hard feelings if it doesn’t work out (most of the time). You can move on to the next experiment until you find something that matches.

You don’t learn about yourself in theory, only in practice. Your level of self-awareness is proportionate to the number of life experiments you run. The more life experiments, the more learning you will have.

Interested in business? Try starting a low-cost e-commerce website. Interested in being a writer? Write every day for 90 days on Medium. Interested in videography? Record and produce 6 videos on your smartphone.

You don’t need anyone’s permission to do any experiment that interests you. Your learning is your own journey.

Tim Ferriss famously experimented by creating 6 podcast episodes as a test of his ability and appetite for audio. The Tim Ferriss Show is now one of the most popular podcasts in the world with more than 600 million downloads

4. Learn from other people’s mistakes

The best type of learning comes from making mistakes. But mistakes can sometimes be costly and hard to recover from. The next best type of learning comes from learning from other people’s mistakes.

I’ve enjoyed this privilege for most of my life. I am one of the youngest of my immediate and extended family. Growing up, I use to think of this as annoying. I wanted to play with the big kids and be treated like an adult.

But being in my teenage years and now in my mid-20s, having people around me who are 3–8 years older provided me a map and a mental model of what I might experience.

I could learn vicariously through their triumphs, successes and failures. Now I am constantly asking them: if you were my age, what would you do differently? What are some of the biggest regrets of your 20s? How would you make the most of your 20s again?

Look around and see who you can learn from.

Chances are you will have older siblings, cousins or more experienced colleagues that you can learn from. Everyone offers something. You’ve just got to look properly and absorb the lessons.

5. Find a tribe of mentors

Every hero’s journey is aided by a mentor. Luke Skywalker had Yoda. Peter Parker had Tony Stark. While fictional, no person in real life is an island. We all need help on this complicated and frustrating journey we call life.

Surrounding yourself with people who have been there and done that is the best investment you can make. Your tribe of mentors is where you can take your challenges and expect some honest and frank advice.

But life is multifaceted. You’ll need to find mentors for specific domains of your life. A mentor you have for your business will be different from a mentor you might have for your health and fitness or relationships.

How do you find a good mentor?

Well, the internet provides a great way to find new mentors. I have mentors that don’t know that they are my mentors. But through their writing, media appearances and podcasts I learned so many life lessons.

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