The Trouble of Pursuing Your Passion & How to Annihilate Self-Doubt

“There is nothing in this world that can trouble you as much as your own thoughts.” - Unknown

I feel like the queen of self-doubt. Even now as I write this, thoughts like, "who the heck am I to think anyone would be interested in reading my 

Have you ever felt like an imposter? Or that you aren’t an ‘expert’ at anything? Or like it would be so much simpler to just not try to go after the things you are going after… because at times it can be so dang hard!

Last night I was chatting with some of the Live Your Legend Local Hosts, some of whom shared these thoughts… because when you are taking a step in a new direction, trying something new, or getting outside of your comfort zone, the self-doubt is super real!

I know that I personally feel that way all the time when it comes to career! I question what I am doing, where it is going and whether or not I should just go get a normal job with a stable paycheck… where I know the next steps and there is a boss to ask the things that I have no clue how to figure out.

There are many days and nights where I have found myself googling ways out of the uncertainty... looking for jobs or entertaining the thought of saying 'Screw it and going to live in a hut in Bali!' At times, that seems like the right choice!

Because self-doubt is there for a good reason. I mean, you know how to exist as who you are right now (because, duh, you are doing it) but you aren’t exactly sure who you will be, where you will fit in or what it will be like if you suddenly become a person who makes a living from playing music. Can you do it? What will it look like? Where will your next payment come from?

It’s something that we can sort-of imagine but is also hard to truly feel until you are there. It doesn’t mean you can’t, but I would argue that our nature is to rationalize a way to stay where we are, because it feels much safer that wherever we are trying to go—whether that is starting a business, a new project, a hobby, doing something you have never done before, etc.

And in these scenarios, you have a few options:

1. Look Within

2. Reach out

3. Give Up out of Despair

And for any of you who read last week’s article on Manifesting Momentum, I think we know how I feel about option 3... #nogozone.

So, here are a few ways to stop self-doubt on the spot, so that you can clear your mind and get to doing the important work that needs to be done—discovering more of you, so you can give more of that to the world!

Look Within

I generally always tend to look within first, whether I feel a positive or negative emotion because I find self-inquiry to be an incredibly powerful learning tool. So in this case I am classifying the feelings of self-doubt as painful because, well they suck!

If you have been around LYL for any period of time, you know that we are big believers in self-discovery. And one of the reasons is to better understand why we do what we do, so we can better control the things we do.

Pain and pleasure are two incredibly powerful stimuli and it is in our nature to retreat from pain and move towards pleasure... but if the ways in which we choose to respond to those desires aren’t actually in line with who we are and what matters to us, we will find the cheap thrills, quick fixes and temporary solutions. The more we do that, the quicker we develop habits around them (even if they are ways that aren’t actually serving us) and then we begin to think that we are subject to genetic victimhood because that is ‘just how we are’.

Which is why we have to learn how to manage short-term pain in a way that aligns with our long-term values.

The better you know yourself, the better read you will have on when you are just feeling momentary pain and recognize the desire for a quick fix for it. The more intentional decisions you make based on the things and values that really matter to you, rather than reactionary ones that leave you running from one thing to the next, the more you start to understand yourself, your desires, your natural tendencies and how to manage them, versus just giving up or being subject to them thinking there is no way out.

We are never taught to approach life this way but when we do, though it takes work, life becomes a lot more simple! This is why we always suggest our free 7 day self-discovery writing challenge as a starting point for anyone new to LYL. It is a simple way to get you into the habit of thinking about your thoughts!

Looking within is the majority of what I write about at LYL, but I also know that looking within isn’t the only solution. There are times where if you dive too deep into your thoughts, they can be your own worst-enemy, which is why I also think it is important to balance out looking within. Sometimes the only way to get out of your own way is to...

Reach Out

This is word for word an email I wrote on not too long ago. I was having a morning where I was taking things far too seriously and getting way ahead of myself. I know about being present, mindful and playful (and have written a lot here at LYL about it!) but hey, we are all human! I think it is only natural to have times of doubt, so instead of beating myself up for not being some perfectly enlightened creature, I appreciate the humanness of my experience. I am thankful for my feelings (both those that are difficult and joyful) because they act as a guide, however I do like to have practices that cause me not to stay stuck in any one emotion. And when looking within isn’t doing the trick, I have many data points that have shown me that reaching out and getting a greater perspective, will.

So on that morning, here’s the email I wrote to an old boss of mine, whom I totally adore!

Dear person I adore,

… I struggle with 'what I am doing' a lot. Many times I am tempted to go get a normal job where I know what I am 'supposed' to do and there is a guaranteed paycheck. I like the idea of entrepreneurship for a lot of reasons, but the linear path of corporate is tempting as well, especially when you wake up on a Monday and are like.... hmmm, WTH am I supposed to do today, haha!

I know you are always trading something for another but I find it interesting that when you reach your mid-thirties, this is sort of the first time where you don't know what you are supposed to do next, you know? No longer the get a degree, get a job, get married, have kids, raise them thing... But maybe that's just the story I am telling myself... but I am curious your thoughts as you've always been such a wise one to me.

In her response, she shared with me her reflections looking back on her life and her career path. Because we all know the dots only connect looking back...She reflected back on her 35-year-old self, and how her whole life changed at that time too, which set her up for the happy marriage she is in today. She shared how she had made numerous career transitions in her multi-decade career path, and that there were four periods where she was either freelancing or tried her own thing out, but those all lasted a few years before she moved on to something new. Not because she is constantly dissatisfied, rather she seeks out change and variety after a few years because it serves her. And she shared that despite her non-linear path, it has always, always all worked out.

By reflecting back on her journey, she genuinely lifted me up because she had the insight and experience to see things that I cannot see, both in myself and about the life I have ahead of me.

I remember the same thing happening after Scott passed away. I had friends and family who were able to see a life ahead of me that I was legitimately incapable of seeing, because I was shielded by pain and grief. I recall a friend saying to me:

“Chelsea, you have mighty things ahead of you.”

I literally couldn’t believe she believed that, because I absolutely could not. But her belief in me certainly stuck with me.

During the times that we doubt ourselves, we are shielded and unable to see the whole picture which is why... 

We all need people who believe in us when we don’t believe in ourselves.

Because times of self-doubt are bound to happen! And we always have the option to give into that doubt and give up out of despair... but we also always have the option to reach out to those who have eyes when ours are blinded.

When pursuing something new, different, challenging or off the beaten path there will be times that you look over to the well-worn trail and wonder why you are not with all the people walking on it.

It will appear that things seem easier over there because there is safety in numbers. And the right decision, may be to join the pack—only you can make that decision, I just hope whatever decision you make it is an intentional one. But I share this story because if you ever feel like you are alone on that beaten path (or the well-worn one!) there is always a fellow wanderer that can help you see what you are unable to see.

Much more on that next week, so keep your eyes peeled for another email from us soon!

- Chelsea Dinsmore

P.S. You can read more on this topic by checking: Never Fail Again: 13 Ways to Fear and Doubt into Fuel for Brilliance!