Defining your own version of success and pursuing it requires courage and confidence.  There will be obstacles along the way, including criticism and judgment from others if you’re not doing what they expect or want from you; the need for the right kind of support from those around you; acquiring new skills; shifting how you spend your time each day; and finding the right approach and pace that works for you as you make changes in your personal and/or professional life.

But sometimes the biggest obstacles come from a deeper, internal place.  These are the obstacles that touch on our own fears and insecurities. We all have them — yes, even the people who seem to be living fabulous lives.  It’s OK to have fears and insecurities, and sometimes naming and recognizing them actually helps us stop them from getting in the way.  

Here are some of the most common internal obstacles that I have seen get in people’s ways:

Fear of Failure.  

It seems obvious that sometimes we worry about whether or not we’ll succeed as we’re pursuing a new path.  What happens if you don’t get a job in a new industry? What if you don’t finish the marathon? What if you fall flat on your face in whatever new endeavor you’ve decided to pursue? 

These fears can really get your brain freaking out — sometimes so much that you end up deciding that change is too scary and you stick to the status quo. I’ve failed repeatedly in both public and private ways – in stand-up comedy, crying at a professional conference where I was a presenter, desperation in a romantic relationship, pitiful attempts at team sports, almost flunking out of graduate school.  It’s not fun. It hurts. It’s humbling. But at least I know I’m trying. At least I’m participating. At least I’m moving forward.  

Fear of Success. 

As strange as this sounds, fear of success is a thing.  What if you achieve the thing you’ve been working so hard to achieve and you’re still not happy or satisfied?  What if you get the degree and the job and then realize that career path that you’ve pursued for four years isn’t for you?  What if you spend all of this energy and then realize you were focused on the wrong thing?

Even if you don’t get your objective quite right the first time, you can continue evolving and changing and morphing it until it is right for you.  Sometimes we have to go through the steps of pursuing something and then finding out it’s not what we want in order to figure out what we really do want. For me, this has taken many years and continues to evolve!

Fear of Others Laughing at You.  

This is a big one and it definitely triggers feelings of fear and of being unsafe.  I know many people who don’t want to take risks or try something new because they’re afraid others will laugh at them.  And people might. But again, at least you’re doing something with your life. At least you’re participating and trying and growing and blossoming as a human being. The people laughing at you are stuck in the same place, judging others instead of seeing how they can improve themselves. 

If this is your fear, I recommend going slowly, finding people who will support you in the ways you need to be supported, and spend time with them. Take the time to get your support system in place so that your supporters drown out your detractors.

Fear of Something Bad Happening.  

This is my own personal fear.  I inherited it from family members who fear change and immediately imagine the worst and most extreme, awful situations that could possibly occur.  Over time, I have found that by saying the hypothetical bad thing out loud, it immediately becomes smaller and more manageable.

I also sometimes personify the bad things as little cartoon monsters and they become less scary.  If this is your particular fear, perhaps you could spend some time understanding and finding a way to manage this fear as it may be getting in your way.  


Don’t be afraid of naming your bigger, internal obstacles — your fears and insecurities — and dealing with them.  Remember, you don’t have to dive into something before you’re ready, but don’t just stand there. Do the hard work you need to do in order to get yourself ready and then go for it.