In Favor of Doing the Unexpected

Two girls lie on their backs in front of a sunny window

Whether it’s thinking about quitting a full-time job or deciding not to have kids, many of us have debated between following a traditional path versus following our heart.

Why we follow the expected path 

If we know in our hearts of hearts that we’d love to pursue an unconventional path, why do we stick with the tried and true? 

It’s not easy being the “first” to do something. 

Maybe you grew up in a home or a community where everyone you knew pursued a traditional path: getting married, owning a home, becoming a manager, etc.  So it was only natural that you, too, grew up thinking: this is the only way to have a good life.

It’s never easy trying to become the first person in your group to break away and do the unexpected. The non-traditional path is scary and unknown. What if I fail? What if I go broke? What if I’ll be alone for the rest of my life?

But you also have to consider the other possible outcome.  

By embracing the unexpected, you could discover a world of wonderful possibilities. You could meet incredible people who feel the same way as you. You could live a life that was one hundred percent authentic to you and your values. 

Just because it’s unexpected doesn't necessarily mean that it’s the wrong move.

Why you might be better off doing the unexpected

Given all the risks and potential pitfalls involved, why would you even consider doing the unexpected? 

Well, to paraphrase George Burns, sometimes it’s better to be a failure at something you love than to be a success at something you hate.

It doesn’t hurt to at least try and do the unexpected. Sure, it might be scary, and you might encounter several bumps along the way, but at least you went out and tried.

That’s not to say that you should just quit your stable job and ditch your friends and family at this very moment. Doing the unexpected doesn’t mean you have to be foolish about it. 

If anything, you’ll want to plan and prepare as much as possible. Get all your ducks in a row to ensure the best possible outcome for yourself. When carving out an unexpected path, it’s all about taking smart and measured risks. 

Define your unexpected path 

First, it’s important to clearly define what it is that you want to do and why. Knowing your “why” will help you be at peace with your decision. It will help you figure out what you want to do in your life and motivate you to find a way to do it. 


  • I want to freelance because I like working independently. 
  • I want to work for a small business instead of a big corporation because I like the flexibility and the opportunity to wear a lot of different hats. 
  • I want to live in a cabin in the woods because I’m happiest in nature. 

If you’re having a hard time figuring out your “why,” it will help to take out your journal and reflect on this topic. Take a moment to examine your emotions and the big feelings that are coming up for you.

For example, you might be feeling guilty for not wanting a family or a corporate job with cushy benefits. Try not to judge your feelings around this topic. Do talk to yourself the way a trusted friend would. 

Example: I know you feel pressured to take that manager job but don’t force yourself to take it if you don’t want to work in a big team. Whatever decision you make will be a good one. If you change your mind, you can always go for the job later.  

Journaling will help you better understand your emotions. You will come out of this exercise feeling a lot more confident and clear-headed about your unexpected path.

Do your homework 

If you’re going for an unexpected career path, then you’ll want to do plenty of research and background work beforehand. 

Gather the right tools, meet the right people, and plot out your goals so that you can create a solid foundation for yourself. 

For example, let’s say you want to leave your full-time job and pursue a freelancing career. Doing your homework can look like…

  • Meeting with freelancers and gathering advice on how to create a successful freelancing career.
  • Creating a timeline for transitioning into freelancing. 
  • Preparing a budget and financial safety net.
  • Transitioning to part-time work first before diving into freelancing. 
  • Meeting with potential clients so that you can already have business lined up by the time you leave your job. 

Find your people 

Just because you’re doing the unexpected doesn’t mean you have to do it alone. 

Now, more than ever, you need a sense of community. Meeting like minded people will help you feel more secure as you navigate your unexpected path.

When you find your people, you can…

  • Get advice from people who’ve been there and done that
  • Vent to others who understand what you’re going through
  • Share your wins and achievements 
  • Build a sense of camaraderie and community

So how do you find your people? 

Tell your friends and loved ones. Start with your innermost circle. Tell the people you love and trust that you are thinking of exploring the unexpected path. They might even be able to connect you with someone who’s doing the same thing as you. 

Go online. You can find just about every single type of niche or community on social media these days. Follow people you admire online and build a rapport. Like and share their posts. Congratulate them when they share good news. And offer advice when they seek it. Before you know it, your online peers will become your real life support system. 

Build your own community. From hosting a weekly open mic at a coffee shop to starting a Reddit thread, you can create your own community to meet your people.

Building a strong support system won’t happen overnight. But with time, effort, and patience you will feel a sense of belonging. You’ll discover that you’re not alone and there are so many others out there who are also doing the unexpected.

Written by JiJi Lee

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