The 5 People Who Will Break Your Heart in Your 20s

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Ah, your twenties. A decade of marvelous growth, decadent spending, and quite a few heartbreaks. Just like the 1920s.

That’s when you figure out a lot about life. What your teachers didn’t want to tell you, didn’t like to tell you, or didn’t know enough about to tell you.

That’s when you’ll probably fall in and out of love with life, with your soulmate, with your passion. That’s when you will get your heart broken, and when you should fail at something you were passionate about.

And you will meet a lot of people along the way. Some of them will try to tell you all about life, some will try to sell you “the perfect solution” for your problems, while others will walk out of your life, leaving you to contemplate on what it means to be in love.

Here is a list of the five types of people you will most probably meet in your twenties.

1. A Fake Guru/Mentor

Life is pain. And you kind of figure it out in your twenties. But that doesn’t mean you admit it. Not right away, anyways.

That’s when a fake guru will show up in your life. They will tell you that life doesn’t have to be pain. They will tell you that, yes, you can click here for success, that you can get shredded if only you buy their ten minute routine, that you can become a millionaire by working just four hours every full moon.

In other words, they are trying to sell you something.

They don’t embody their philosophy, they don’t practice what they preach, and because they can’t do it, they tell all about how you can do it.

How can you spot a fake guru?

George J. Ziogas wrote a brilliant piece about this, and while his article is about entrepreneurship mentors, I think most of his advice applies to all sorts of gurus/mentors.

In my opinion, the best mentors are the ones who are reluctant to become your mentors in the first place. They are the ones who are so busy getting stuff done that they don’t have the time or energy or patience to teach you.

Develop a strategy to get close to them. Work for free if you have to. You will learn a lot more just by watching their habits and actions and mindset than you will ever learn from enrolling in some course you found on some fake guru’s Instagram page.

2. A Member of Your Family (Or All of Them)

This doesn’t have to be the norm, but there’s usually some family member who will take issue with you dropping out of college to pursue a dream, or trying to open a business rather than choosing a 9–5 job.

They are trying to protect you from flying to close to the sun and getting your wings burned by clipping them away. There, problem solved.

In my case, everyone was against me. My parents, my grandparents, even my aunts and uncles.

I spent years being the black sheep on the family because I didn’t listen to them and chose to follow my passion.

There’s a lot to be said about following your heart and intuition, as Steve Jobs so famously advised us, and if there’s ever a perfect time to do so, it’s in your twenties.

It can be heartbreaking to realize that those closest to you don’t share your vision, but it’s a tired cliche that planes take off against the wind, not with it.

The thing I told myself all those years, as I struggled to make it as a full-time author and blogger, was that I was the only one who was going to die when the time came, so I might as well live my life the way I wanted to.

It hurt not having my family believe in my dream, but it also made me develop the inner fortitude required to persevere until I became successful.

3. The First Heartbreaker You Fall For

The one that walked away.

The one that you considered your soulmate.

The people who make a lot of mistakes in their first serious relationship are the ones who later develop the qualities required to have strong relationships.

All my friends who wasted most of their twenties by being in dysfunctional relationships, only for their partners to break up with them a month before the wedding, are wasting their thirties as a result.

I know it sounds odd, but I am truly grateful for my first heartbreak. I am grateful that I learned how to be my own person, how to set boundaries, and figured out what was most important to me.

Our first serious heartbreak teaches us that we must create our own happiness, that we shouldn’t be defined by the person who’s sleeping next to us.

The ability to feel complete even when not in a relationship is often the by-product of your first heartbreak. You understand that it didn’t work out because you were relying on them to provide you with what you had to create on your own.

4. The Boss You Hate

Odds are, in your twenties you will work at least a job that you hate, mostly because you’ve just now completed the transition from having your needs taken care of by others to having to assume responsibility for your own life.

In effect, this means that no one’s willing to encourage you for trying, but they are all judging you by your results.

Effort no longer matters.

And your boss couldn’t care less if you gave it your best shot or not. You either got the job done or not.

And you will hate them for it. They will break your heart because they will show you what real life looks like: it’s’all about the results, not the effort, not the intent. Results.

You will hate them because they won’t seem to appreciate your efforts, and because they will always demand more of you.

Consider this your rite of passage as a twenty-something professional.

We are walking down a path towards becoming competent and confident adults, and this means that we must let go of our desire to be comforted for our mistakes.

5. The One Whose Heart You Have To Break

There are few things that will hurt more than closing that door behind you, never to return.

Whether it’s a friend you have to let go because you no longer share the same principles, or whether it’s your partner, you will have to break someone’s heart.

And this, in return, breaks your own heart.

The look of disappointment on their face, the realization that you lost a lot of time and energy trying to make things work between the two of you.

But it’s extremely important that you walk away from a relationship that no longer serves you. It’s not selfish, it’s best for the both of you, for there is nothing more tragic that two people realizing they hate each other in their forties, when they’ve got so much to lose.

Most people don’t let go of the people who are not right for them. They think about all the time they’ve spent and they choose to stay.

Later on, as the differences between them become more noticeable, they often regret not walking away when they had the chance. This is how you ruin your life.

One of the most valuable lessons we can learn during our twenties is that we can care deeply about someone who’s just not right with us. We might lose them along the way, as our priorities change, we might have to walk away because they are not right for us.

It’s going to hurt, but you’ve got to let go of the people who are not a right fit for you.


These are the five types of people who will break your heart in your twenties, forever changing your life, your priorities, and your definition of love, life, and success.

We do learn a lot more from failure than we ever do from success.

There’s a fragile quality that one’s heart has if it has never been broken.

Don’t be afraid to break your heart in your twenties. You will recover. It will make you stronger but also a lot wiser as you develop the inner fortitude and mindset to make the most our of the next decade of your life.

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