How I Learned To Live My Best Life Even Though I Was Feeling Lost & Confused

Living your best life doesn't mean that nothing bad ever happens.

Life Advice For How To Be Happy & Live Your Best Life While Feeling Lost & Confused Unsplash 

Happiness can often feel impossible when bad things happen — but in the pursuit of happiness, you're not always going to know how to be happy. If you want to know how to live your best life and pursue authentic happiness, even when you're feeling lost, sometimes you have to learn how to be happy with yourself when times are difficult.

What's best in life for each of us is different dependent on what your version of true happiness is.


If you're asking yourself, "Am I living my best life?" then there are likely things you'd like to change in order to find happiness and discover what your version of your best life is.

RELATED: 20 Easy Ways To Be Good To Yourself Today

The truth is, it's often ugly, frustrating, and devastating on the way to living your best life.


For example, during the last decade, I’ve had to make some difficult decisions that were just mistakes in the making. Arriving at 39 years old with no real estate investment, no husband, a business few people know about and a serious lack of connection sucked.

It doesn’t just suck for me. It sucks because every new person who I tell, “I’m a breakup specialist and a medical medium” says to me, “Where were you months ago when I needed your services?"

I’ve been in gridlock. I’ve been in between the life I’d like to live and the one I’m in. I feel two-faced in my pursuit of happiness.

I’ll use the last guy I dated as an example. He's brilliant at writing, a charismatic speaker, highly intelligent and motivating. He knows how to pattern words to create a powerful impact. And he was dangerous.


The person he was able to present to the world helped many people. He even presented as self-reflective. And all of those attributes often contributed to creating positive outcomes.

But, when everything really hit the fan between us, none of who he was to the world was expressed in how he dealt with our relationship. His very best when he was at his very worst was controlling, manipulative, demeaning, degrading, and cruel.

We all have different sides to who we are. Some of them are more pathological than others. It is difficult to reconcile and for some of us, it’s impossible.

So the truth of my story is that I’ve been attempting to get my social image to match up with how I really am behind the scenes. At the moment of writing this article, I had $7,000 in credit card debt, I was living on one egg and piece of toast a day, but I kept up my $2.50 cent cup of exceptional coffee habit.


I was so worried about money, I stopped working out. In fact, massive parts of my life went into paralysis. I tried to solve my money woes earlier in the year by gathering a “team” of people that could help my business grow.

But what happened is that I hired a marketing company that was bad at communication and ended up having to quit the campaign before it could ever get off the ground, consequently making my money situation worse ... not better.

I’ve been extremely mad at myself for spending the whole of my 30s dating one bad man after the next. One boy after the next. One personality disorder after the next. One spiritual predator after the next.

Where was my happiness?!


In 2016, I had five different hookups with five different men that were all mentally ill. One had major substance abuse issues, one was cheating on his girlfriend with me (I found out after the fact), one was a sex addict, one was hooked on ayahuasca ceremonies, and the last one was a “flat-Earth” idiot.

It’s now 2019, and I’m no better off. I stopped hooking up with randos, but I got messed up by the last guy who wasn’t over his ex, kept her in the picture while telling me he loved me, and as things began to crumble, showed some frightening narcissistic characteristics.

Every year of my 30s has been marked with a major trial. I’ve been through multiple breakups, been fired twice, moved five times, lived in a van for one month (on purpose), lost friends, went through major health scares, and almost ran out of money multiple times.

But that doesn't mean that happiness is impossible to find.


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Trust me, I’ve asked myself the question you're thinking: “What’s wrong with this woman?”

Doesn’t someone with a masters in counseling know better? Especially someone who has a business that is focused on helping people go through a breakup? There is plenty wrong with me when it comes to living the American Dream. Simply, I'm not living it.


I’ve gone a different route. I want to make something perfectly clear, the only thing that has pulled me from the depths of hell and out of this chaos has been my education and creative soul.

So, I understand how my ex can be such an effective force for good in other people’s lives, but be totally destructive in his own.

As the saying goes, “The cobbler's kids have no shoes.”

Giving advice is easy. I don’t have to implement the advice or information I give to my clients. They have to run in through their own process of trial and error.

It takes a massive amount of energy, clear intention, and focus to run your own life. And you all do it by looking to the fools around you for guidance.


For instance, Tony Robbins is credited with changing millions of lives but just recently was accused of harassment and berating rape victims. No man is a deity.

This beckons the question, “So, what is a 'good' life? What is necessary to feel good about your life? Why is life even worth living?

A lot of people just give up when faced with this question. Some kill themselves. Some turn to an addiction to numb the pain. Some seek fame. Some are life-coaches. We are trying to cope, innovate, do better, and rinse and repeat.

We all want to live our best lives.

I can’t count my failures or successes, because I’m not at the end of my life. I’m in the middle of some twisted plot line that has involved the death of my parents, getting a degree, having great sex with bad guys, blowing money, traveling like a gypsy, and feeling totally clueless.


We're not supposed to admit these things.

I’ll go one further. When my parents died and my grandma died, I got a sum total of about 300K. I spent all of that money and didn’t invest one lick of it in real estate, stocks, or commodities.

I didn’t focus on growing that money because I wanted to die. I figured I’d use it until the party was over and then I would be over. I wasn’t invested in life.

In fact, looking back, I wanted to be an entertainer who was on tour ten months out of the year. But that seemed like even more of a long shot than just being a breakup coach in a saturated market.

So, I just kept doing more of the same thing — trying to get out of my comfort zone and find what makes me happy.


Some days trying to be a good person sounds like, “Well at least I’m not a drug mule.”

After a sojourn into the darkness of my thoughts, I reach for my self-development books. I pull tarot cards. I attempt to learn how to be a digital marketer so that I can actually reach “my audience.”

I’m one woman playing 100 different roles. But the really important roles of wife and mother aren’t something I've been cast for at this time — and that's OK. Because I'm still on my way to living my best life.

So, where have I been?

I’ve been screaming into the void. I’ve been fighting the good fight — mostly against myself. I’ve been wrecked by lust and fantasy. I’ve been hiding out in a basement. I’ve been curating a bigger dream.


I’ve been sick of hearing people tell me what to do because I can’t tell the difference between the liars and the true teachers.

Being a counselor is something that I do to make a living and to live my life. And sometimes it feels like a lie. It feels like the qualifications it takes to directly influence someone else come with a code of ethics I won’t ever be able to live up to.

Part of me wants to put a marketing spin on this story with some sort of resurrection flair to it. I’m not going to do that. I just want you to know that you are not alone in this big, intimidating, and frantic world.

So to answer the question I get asked the most, “Where were you those times I needed you?” I’ll give you the answer that I hope you will tell yourself the next time you feel like you are failing, “I’ve been living.”


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Rebekah Freedom is a spiritual advisor & breakup specialist who holds a Masters in Counseling Psychology from Naropa University. She divides her time between living in Colorado and California.