5 Reasons You’re Not Following Your Dreams

Since my longtime obsession is trying to follow some semblance of my dreams, I figured this week I’d focus on what seems to be so f*cking difficult about that. Truthfully, it’s my own belief system, filled with fears and limitations that hinder me, regardless of how often I try to convince myself otherwise. I imagine you can relate to this, as almost all of us have that secret dream deep down that we protect and nurture, whether we ever act upon it or not.

I’ve done a lot of reflecting on why it seems so impossible and terrifying to go after what we want and I’ve noticed several recurring themes. Here’s a list of them so you can stop making excuses and become the most amazing human you’re capable of being.

So firstly, what’s your “big dream?” Get clear about that shit because it’s going to be tough to pursue something without a general idea or direction. Now consider what’s actually preventing you from becoming your most desired version of you.


Allowing Ourselves to be Limited by Fear

Ugh. Fear sucks it. I hate feeling scared, but as we know – if everything were easy and never scary, we’d have no need for courage. Fear is one of those things that often lie to us. It plays on our insecurities and convinces us that we will never reach greatness or the secret successes we long for. It tricks us into making excuses and into settling for far less than what we once hoped for ourselves.

We often disguise our fear as pragmatism and choose the path that’s considered safe. It’s a trade-off. We choose more structure, safety, and convention over freedom and individualism but more uncertainty. When we settle into something we don’t want long-term, we risk wasting our potential and slipping into a resignation for a safe, comfortable lifestyle but lose the opportunities for growth that facing challenges presents.


But wait – PSYCH! There is no such thing as “safety.” That’s also a lie we tell ourselves to feel secure in a world full of unpredictability far outside of our control. There is no safe place, it’s all a matter of how you view the world and what you’re willing to exchange in order to make your dreams come true.

I’m not suggesting that you’re life is destined to suck if you settle. In fact, I believe you can have a wonderful, rich life full of meaning. Good enough is often a great goal to strive towards. I just know that you and maybe only you alone, will in some capacity always carry that small, secret longing for a life un-lived.

Comparing Ourselves to Others and What They Think of Us

We care a whole lot about what others think. But respectfully, fuck them.

Your life is yours and no one else has to live with the guilt, regret or self-imposed anger you’ll have to live with because you did what you were “supposed” to do. This life should be by your design and anyone who wants to laugh at you has probably not pursued their own dreams with unrelenting fervor (or they have and they forgot what that’s like).


Your parents, friends, partner, and children don’t have to live with the decisions you’ve made, so release the need to seek other’s approval in this process, you’ll be much happier.

It also doesn’t matter if someone else was 21 when they hit it big or became famous. Whatever, that’s their process and yours may look very different. Some of the greats didn’t make it until they were far past middle-age and many of the most brilliant thinkers weren’t recognized until they were dead! Don’t compare yourself to anyone, ever. You can gain some inspiration or borrow some tricks of the trade, but ultimately your path is unique to you.

Not Feeling Deserving

Many of us have those people in our lives who tell us from the time we’re young that our dreams are unrealistic. They project their life of frustrations and failures or unmet dreams and expectations onto us (usually not purposefully) and we begin to carry the same attitude about our own visions. We assume that they’re right and that it’s time we push our dream to the side in lieu of something seemingly more tangible.


You deserve to have the life of your own choosing. I understand that there are many barriers to this belief. Others treated you with cruelty or didn’t support your dreams, your self-esteem and belief in yourself is lacking or damaged. There could be a million reasons, but ultimately – YOU are the only one who can decide you’re good enough and that your dreams are there for the taking. There has never been and never will be anyone exactly like you, with your perspectives and unique talents. No one will offer the exact things you can and that makes you the perfect candidate for that thing you really want.

Like Marianne Williams said, “Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, Who am I to be brilliant, gorgeous, talented, fabulous? Actually, who are you not to be?”

Giving Up Too Soon

Success often takes a while. We’re often laying the bricks of effort long before our elaborate palace of fantastic accomplishment is completed. I think what gets discouraging is seeing other people’s successes in full bloom, rather than the long list of consistent rejection letters, missteps, failures, and dinner conversations with friends and family urging them to forgo their dream and softly accept defeat. It’s not going to happen overnight and we’ve got to build the resilience to keep going, even when everything seems hopeless.

Some things, we can’t change. We may not be able to go back and become a professional baseball player at 53 or an Olympic figure skater at 70. (Or maybe we can?) but if that’s the case, then we owe it to ourselves the forgiveness for not pursuing those things in the capacity we wanted in order to avoid living a life of regret. We then have the choice of practicing acceptance and get to reimagine the ways in which we can still make that dream a reality. Maybe you can become a coach, an announcer, or even a loyal spectator who spends your free time at the batting cages, in the twilight league, or lazy Sundays on the rink.

Waiting for that “Perfect Timing”

There is no perfect timing, period. I did this for three years with my writing and videos. THREE YEARS! I brainstormed and babbled about creating content. I told me friends, talked about video ideas, but never pursued it. It was always, next week, month, year. “When I leave this job and have more time, when I’m less stressed out, back in New York, when I have more energy…then the perfect time will prevent itself.”

No. No, it won’t. It’s today, or it’s never at all. You will tell yourself you can do something your entire life and then one day you die. Now is the opportunity. If you don’t have the time, MAKE the time. If it’s important enough to you, if you’re unhappy enough with your current situation, you’ll change it. Like Anais Nin said, “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.

Not everyone will live the life of their dreams, but that doesn’t mean we can’t turn our dreams into our hobbies. I’m not suggesting that we are destined to live an unhappy life if we don’t pursue our big dream, and who says a successful life is ONLY one where we’ve attacked every dream we’ve ever had with unyielding abandon? I just think we can work towards creating a new reality for ourselves, one in which we don’t find ourselves regretting the things we never did.

Here’s a sweet video I made on this topic.



The Importance of Listening

Last week, I did a piece on the importance of learning to admit when we’re wrong. Since listening is such an important part of that process, I thought it would be interesting to expand on. Listening is one of those things that separates small-talk from significant and enlightening conversations, good leaders from transformative innovators, and casual relationships from profoundly cherished connections. It allows us to better understand others, making it easier to discover the sense of belonging we all crave.

So where do we start? Let’s talk about why the world needs more listeners, why we each crave to be heard, and how to go about doing it properly.



Why Listening is So Important

Okay, so take a moment to consider whether or not you’ve ever truly listened to someone else. I mean, actively paid attention to what they were saying without waiting to respond. How about resisting the urge to engage in an internal monolog filled with opinions and judgments about what they’re sharing? Did you combat the itch to somehow make it about or relatable to yourself?

It’s difficult, right?

It’s challenging if we find it boring or not relatable to ourselves. So we have to remember that listening to someone else isn’t always for or about us. We can always learn through listening, but a lot of the time people just want to exist in a space where who they are and what they’re saying is valued.  It provides a space for true understanding, and when we can better understand who someone is and where they’re coming from, it’s much easier to practice empathy for their experience.

We begin to take their behaviors less personally because we begin to grasp the underlying emotions and personal history behind them more clearly.


The late David Foster Wallace, author of Infinite Jest, and brilliant human, delivered an eye-opening commencement speech called, This is Water which reminds me of this idea. It essentially points out that we are not the center of the universe, however much we may believe that to be the ultimate truth. He points out that every single person is consistently experiencing their own inner struggle and that we’re all just doing the best we can at any given moment. It’s one of the reasons listening to someone else’s experience is so important.

Why We Crave To Be Heard

It’s pretty simple, actually, and it always seems to boil down to one thing. We want to know that we matter. 

Most of us at some time or another, probably when we were young, weren’t listened to. Maybe we were products of neglect and no one was there to nurture us, or our feelings were dismissed by our parents. Maybe we tried to be vulnerable, only to receive a rejection from our peers or romantic partners. Perhaps we were told that we were too loud, too expressive, to be quiet, or to behave.

Sometimes we close ourselves off, unable to talk about our truth for fear of further pain or rejection and avoid the spotlight entirely, being the “good listener.” Or, if you’re like me, you overcompensate for that absent attention by consistently vying for the spotlight, praying you’ll somehow find the love and acceptance you so desperately longed for all those years ago.

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Ultimately, we all want our existence to be validated. We want to know that it’s okay to feel the ways we do and for someone to normalize our particular brand of crazy. We need to be reminded that we aren’t alone in these experiences to escape the more difficult existential truth that we ultimately always are. We seek to be understood and recognized for our contributions to the collective.

We want to know that our stories are relevant and that we matter, that our lives were worth living and are worth remembering when we’re gone. We want to feel less isolated and alone and to find a sense of belonging through connection and intimacy with others.

How to be a Kick-Ass Listener

1. Put Your Phone (and Any Other Piece of Technology) Down

If you want to be a good listener, you’re going to have to be present and attentive. I know, I know, ughhh so annoying that I would have to put down my phone, close my computer screen, and actually give a shit about something.

Baby steps, people.

If you’re distracted, you’re wasting both of your time, and it’s rude to the person you’re trying to connect with.


Look at them, (or in their general direction, prolonged unwavering eye contact can be unnerving) practice using your EQ and body language, and give them time to express their thoughts without interruption. (Intermittent head nods and mhm’s are acceptable…use your discretion and stuff).

2. Stop Making it About Yourself

When you’re listening to someone else – it’s about them. I know that as much as I love being included in everything, this is their time to speak, proclaim, declare, lament, verbalize, vent, have a mini meltdown, make tasteless jokes, have a weird tangent…whatever.

We’re aiming to hold space for someone as a sounding board. Resist the urge to offer unsolcited advice or turn the conversation back to yourself, unless they’re hoping for reassurance and relation. If they want feedback, offer what you’ve got and ask clarifying questions.

  • If they’re offering constructive criticism, HEAR IT. I cannot stress this piece enough. Every piece of feedback you hear is valid because it’s the way someone else is experiencing you from their perspective. Take it in stride and fight the urge to explain yourself or justify it unless they ask you for further clarification about the situation.

3. Be Understanding and Empathetic

Maybe you think what they’re complaining about is bullshit and they sound totally entitled. Maybe it’s a super tough conversation and they’re sharing something vulnerable or embarassing. Put yourself in their shoes and keep any judgements or opinions to yourself. Seek to understand where they’re coming from and why they might be feeling the way they do.

Sometimes we just want someone to validate that the current situation totally sucks or is absolutely awesome – we don’t need anything more or anything less.

For additional resources, my most FAVORITE website on the internets, The School of Life has an AWESOME video on how to be a better listener – check it out here.



Why We Need to Learn How to be Wrong

I’m wrong several times a day and admittedly for me, it’s embarrassing every time. But it isn’t the worst, and as I practice self-love and continuously work on being less of a self-righteous prick, it gets easier.

To be wrong is to be given an opportunity to take personal responsibility for our shortcomings and to reexamine where and why we failed. It means that somewhere along the way, we forgot to take the blinders off and some part of our rigid perception refused to acknowledge differing points of view. It means we may have been too self-focused and out of touch with the bigger picture of another – or many other’s – reality.

So let’s look at why being wrong is so f*cking hard sometimes, why it’s an important skill to learn, and how to do it gracefully.

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Why Being Wrong Sucks It

Why do we feel defensive when someone tells us that we’re wrong? Aside from us wanting to believe we’re perfect human beings and the best at literally everything (we’re not), we also want to feel heard and have our experiences validated. We also tend to do this weird thing where we attach our sense of worth, esteem, and overall lovableness to whether or not we know things about stuff.

When we do this, we begin to view ourselves and the world in a way that we take very seriously, and instead of holding a belief, we end up becoming the belief. That’s why we feel defensive or even freak out if someone challenges or questions our views. We’ve actually built parts of our identity around those views, sometimes unable to be honest even with ourselves. So, when we discover that we’re wrong, it means we may have to change something or face some hard truths.

Change can be scary, so we interpret any challenge to our belief system as a real threat to our comfort zone, an insult to our competence, or a hindrance in our bullsh*t quest to “be good enough” through being right.

Making mistakes can feel vulnerable and anxiety provoking. What if people reject or judge us if we give the wrong answer or ask a specific question? (Well, maybe those people are insecure…or total douchebags in which case, f*ck ’em.). BUT – we feel foolish nonetheless because we were so, so certain that we knew what was going on, which offered us some sense of control in a world where we rarely have any. No one wants to fail, especially in front of others.

Why You’ve Gotta Learn How to Do it

When we think we already know everything, we lose our ability to really learn anything. We also lose our ability to think critically and creatively. We stop using logic and function solely from our emotions, erupting unexpectantly and rationalizing our rigid and sometimes hypocritical beliefs. We wall ourselves off from taking in new and transformative information.

If we can’t handle being uncomfortable, we miss the opportunity to expand and gain a more holistic understanding of the world. We’ve gotta learn to listen (and I mean really listen), not just wait for our turn to talk) to the experience and feedback of others. If we can’t consider the potential truth in someone else’s perception of us and instead take it as a personal attack on our character, how are we able improve? It takes courage and humility to own mistakes, especially when others are depending on us.

So, why bother learning? Costa Rica Travel Study Abroad Rainforest Adventure

Well, being wrong is usually relatively harmless. Maybe I was wrong about which exit we needed to take on the thru-way or that eating a 3-day-old burrito wouldn’t make me sh*t my pants. Annoying yes, but they aren’t necessarily hurting anyone. Sometimes though, these moments of “wrongdom” become more serious, creating problematic situations.

Let’s look at a quick example.

Maybe you’ve chosen to label yourself as a liberal or conservative and deeply identify with either. However, they obviously have many contrasting views. It’s easy to see how someone could perceive the other side’s opinions as offensive or attacking even if they aren’t objectively offensive, especially if they’ve already made assumptions about the people – not the ideas. Both sides become defensive, and feel unheard and powerless, triggering emotional or aggressive responses. This ends any chance of having a true discussion and seeking real understanding.

Now you’ve got two sets of people who identify so strongly with their respective belief systems, they are unable to step back, think critically about, or attack the ideas they disagree with because they have somehow become the ideas themselves, determinately censoring and protecting those ideas – and subsequential personal identities – from unwanted criticism or question.

On a larger scale, we then cast our ballots without challenging our own opinions, surrounding ourselves with echo chambers that only serve to validate the beliefs we already have, sometimes to the point of extremism.

When we believe our viewpoints to be the “right” way with such staunch and blind conviction, we are unable to see the intellectual flaws or hypocrisy that may exist in our own arguments. We’ve gotten so far into the argument or belief that to abandon it now would be embarrassing, make us feel even more powerless and ashamed, or worse – feel like a failure.

How to Be Wrong and Not Look Like a Total As*hole

Through being wrong, we (hopefully) learn something valuable and become more empathetic and compassionate to the experiences of others.  we recognize that our view of the world was more narrow than we wanted to admit – and that’s a good thing.

Be Passionate, Not Obstinate

Passion is an incredible attribute. To believe in something with enough conviction and tenacity to bring a vision to life is rare and extremely admirable. It’s also one of the main ingredients of success. Although a fundamental component of achievement, passion can sometimes become misdirected. Good or even great intentions can become muddled or tunnel-visioned and what was once a passionate pursuit, becomes an obstinate inability to look at things differently.

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Luckily, passion is one of those wonderful things that can be channeled and redirected. When we’re able to cultivate the ability to self-regulate in moments of passion, we can then project our energy and enthusiasm in a more balanced way.

Stay Open to New Ideas

It’s easy to become set in our ways, especially when we surround ourselves with people who view the world in a very similar way that we do. One of the biggest catalysts for open-mindedness and receptivity to foreign places, people, and ideas comes from exposure. When we are willing to approach new and strange experiences with courage, we are more likely to walk away with a broader perspective and clearer sense of understanding and tolerance.

I’m not suggesting that you stop spending time with the people who inspire and invigorate you, I’m simply encouraging you to do something new. Then, take a moment to examine when, where, and why you may have encountered difficulty and discomfort because that’s where you’ve got work to do.

Always Challenge Your Own Beliefs

We’ve got to be able to question our own truths and continually examine what we hold to be the “right way” otherwise, we are in danger of stagnation and extremism. It’s easy for us to become prisoners of our own fear of the unknown, inadequacy, and judgment. That’s why it’s important to always see it from both sides.

Being wrong can be difficult, but it’s necessary if we want to grow. The next time you’re challenged with a tough idea, think of it as an opportunity, rather than an attack and you’ll begin to reimagine the way you view the world.